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Dating Anna Kendrick
« on: November 27, 2019, 11:05:12 AM »
Title: Dating Anna Kendrick Part 1 - Super Bowl Betting
Celeb: Anna Kendrick
Codes: MF, Oral
Disclaimer: This is an act of fiction. I do not know Anna Kendrick at all and this scenario did not actually occur. I make no money from this story.

Summary: Anna Kendrick attends a Super Bowl party and decides to make some sexual bets with one of the guests as a way to spice up the evening.

Part 1: The Wager

“The bet is simple Og. I win and I get to experience your apparent world-shattering eating out,” the woman proposed.

“And if I win,” I asked the gorgeous actress.

“Simple. I know you’ve heard of my reputation so if your team wins then you get the best blowjob of your life,” Anna Kendrick answered.

*              *              *

3 hours earlier

It was finally here….Super Bowl Sunday. The day only came around once a year and the big day was finally upon us. What made it extra special this year was the fact that my favorite team, the Seattle Seahawks were competing for the Championship. They had done so last year and proceeded to go on and win their first title in their history, I was a big believer that they were going to do it again.

Like most of North America, I was going to be glued in front of the screen, taking in all the action as it went down live in Arizona. I was throwing a party at my modest house in Vancouver in Canada, though modest for Vancouver standards still meant a house worth half a million dollars.

It was three hours before the big game and I thought I had everything taken care of. I was expecting about 15 friends over for the game, but that number usually expanded as a friend would bring their new boyfriend or girlfriend. I was ready for this and made sure that the keg was tapped,and extra pizza and wings were ordered. Hell, I even had a small generator standing by, in case we lost power so that we wouldn’t miss any of the action.

I thought I was prepared for everything until my phone rang and I could never have foreseen this occuring.

“Hello,” I asked into the receiver of my cell phone.

“Og! It’s me Anna, Anna Kendrick.”

I was happy that this wasn’t a video call because at the mention of her name my mouth went slack jawed. Before continuing with my narrative I should give background information on myself. I was named Ogden by my wealthy parents nearly 30 years ago and most of my friends shortened that and simply called me by my nickname Og. Naturally that drove my parents crazy, especially my overbearing mother, but thus I digress.

So how do I know one of the hottest (both in terms of work and looks) actresses in Hollywood right now? Well remember when I mentioned my wealthy parents? Well it turns out they got into the film producing business awhile back and I took advantage of this by getting jobs on some of their productions. I was busier when I lived in Hollywood but when I got an offer to take over one of my parent’s smaller companies in Vancouver I jumped at the chance and headed to the rainy city.

I know, I know, I still haven’t answered how I know Anna. Well, just because I got jobs on movie sets due to nepotism doesn’t mean I’m not good at my job, or even personable for that measure. I’m both of those things in spades, so when I was working on the set of a small indie film called Twilight, I was introduced to the talented actress. She didn’t have a large role in the film series, but that was a good thing, as it meant lots of time waiting around on set between shots, and that is when our 7-year friendship started.

“Anna! Shit, long time. I guess you’ve had an excuse with your occasional film scheduling,” I jested, knowing she’s been shooting films for nearly 4 years straight with little downtime.

“Well I’m kinda a shitty friend too…oh and I don’t like you that much,” she replied, not missing a beat.

“Friendly as always,” I laughed. “So what prompts the call to a guy you are revolted by?”

“Well you see, I’m hoping to use you,” she answered.

If it was anyone but the super cute, super sexy actress I would have probably made a joke about using me for sex. However, I haven’t talked with Anna for over half a year, and even then it was only through text, so I went with a standard reply.

“Well as I’ve told you in the past I’m out of the murdering hobo game but I can probably get you contact with someone still active,” I joked.

“I’m so pleased that you escaped, I was growing concerned that the business would corrupt you,” she laughed. “Actually I was hoping to use you for your big screen TV. I’m totally gonna sound like a stalker but I saw you post a pic of it on Instagram a while ago…and I may or may not have done the same on Facebook and saw you were throwing a Super Bowl party.”

“I didn’t know you were so creepy. So does that mean you are in my neck of the woods,” I asked, my interest very much peaked.

“Yeah, I landed here the night before last to do a week of shooting. So I either watch my Patriots kick ass here in my hotel room alone like a loser or hang at your party and feel like slightly less of a loser,” the actress joked.

“Several problems with that. First of all my party is not for losers so I’d have to make an exception for you. Secondly, I’m a Seahawk fan so you will have to check that attitude at the door,” I replied.

“Well seeing as I’ve already invited myself to your party, me celebrating as the sexiest man in the world crushes your pathetic little birds is something you’ll have to live with,” the talent girl shot back with.

“Haha okay fine, you win.”

“Thought you’d see it my way. Text me the address, when I can show and what I should bring,” Anna said.

We exchanged pleasantries again before you hung up. I stood in utter shock for another few minutes as the realization that the woman I’ve had a crush on since we first met was coming to my party. Despite the fact that I always felt that we had a flirtatious bordering on sexual chemistry when we hung out, nothing actually happened. Whenever I had the courage to ask her out on a date she seemed to have a boyfriend, a while a noted hints of jealousy when l brought up a girlfriend around her.

It felt like it took forever for the game time to finally arrive. I tried to occupy myself with busy work, making sure the keg was on ice and that there was enough food and everything like that, but all I could think of was Anna. He always had a thing for petite woman, and Anna fit that description to a tee.

Of course that wasn’t the only of his sexual preferences that the talented actress checked off for him. He was really into redheads, and though she was a flaming ginger, her light auburn locks was close enough for him. Then there was the matter of him being a boob guy, and boy was that an area that Anna was definitely up to task with.

Despite the fact that she was so short and skinny, Anna was truly blessed with an absolutely jaw-dropping bust. In fact her tits were always assumed to be fake by most who knew her given how perfect they were, however her great boobs were all natural and just hung perfectly in front of her thin body.

Luckily when people started to show up the afternoon seemed to go by quicker, though his thoughts still would drift to the attractive actress/singer. With every new friend that entered my house I would have hope that it was Anna, but with each passing person it was not her.

Finally, with the national anthem being song there was a knock on the door but I was off doing other hosting duties. I didn’t realize that Anna had arrived until she stepped into the living room and the place feel near silent as all my friends observed the celebrity.

“Anna, you made it,” I said probably too excited. “Oh everyone, this is Anna Kendrick. Anna these are the guys.”

“Hi everyone,” she said with a warm smile and awkward wave, both very characteristic of her.

I got up from the sofa that I just had gotten comfy on for the first time since everyone started arriving and crossed the living room towards her. The auburn-haired beauty wore her locks down, cascading down her tiny frame to about her mid-back. Given why we were all there she wore a tight-fitting woman cut New England Patriot jersey and jeans that looked like they were drawn on.

“Find the place okay,” I asked.

As we approached I opened my arms for a hug which she seemed more than happy to reciprocate. I didn’t want to come off as too creepy and hold the lock too long so I broke contact after 3 seconds and looked at her again. She wore minimal make up as usual, always seeming to get by on her natural beauty, but today she wore some black eye liner which made her green eyes pop even more than usual.

“Yeah totally dude, though the cabbie may have taken longer than I’d have thought,” she replied.


“Would love one. I brought tequila,” she said, holding up, which got a cheer from my onlooking friends.

I walked her into the kitchen, at which point she filled a cup up to the brim with beer while I tracked down every shot glass I owned, which seemed to be just enough for everyone at the party. We both made ourselves a small plate of food as we chatted about our lives the last few years. When we had finished we headed to the living room and I made room on the sofa with the best view of the TV for both myself and Anna.

“So are you all Seahawk fans,” Anna asked, looking around and seeing most of the guys and girls in some form of Seattle gear.

“I think you’re the only Pats fan here tonight,” I shared.

“Yeah, you Tom Brady groupie,” one of my friends uttered, drawing laughs from everyone else.

“Firstly, Tom Brady is more than a man, he’s a God. Married to Gisele, going to win his 4th ring and is one of the elite QB’s of all-time. I’m no groupie my friend, just an admirer of greatness. Secondly, I was born just outside Boston…ass,” Anna snapped back, eliciting her own set of laughter.

The game was just about to kick-off then a commercial came on for prop bets again. This brought about fresh chatter from some of the partygoers, ending in a few guys asking to use my computer to make a few last minute bets. I told them where it was and focused back in on kickoff…and talking with Anna of course. We continued to banter back and forth for a little while longer as Seattle won the toss and elected to kick.

“You seem pretty damn cocky,” I finally told the beauty.

“I really am,” she said, taking another sip of her beer.

“Care to make it interesting,” I said.

Part 2: Halftime

“So what happens with a tie,” Anna asked me.

*              *              *

1 hour earlier

Now the bet with sexual implications may have come from left field to most, including myself, but a smaller part of me wasn’t too shocked about the news. When Anna first invited herself to my party a few hours ago, I spent the time researching her by asking some mutual friends we shared. I learnt that she always, sorta had a crush on me and that the time she wanted to hooked up I had a serious girlfriend.

However, I also learnt that Anna was single now, and not only that, but that she hadn’t gotten laid in a while. I hoped that would mean that she was sexually fueled and given how quickly she resorted to a sex bet, turns out I got my wish. Of course she didn’t jump straight into oral sex as the prize, but we had rejected the money bet or the loser having an embarrassment punishment offers in the first place. Her devious mind then went to sex and there was no fucking chance I was turning that down.

We had stayed seated together on the sofa throughout most of the game. Even when one of us would go grab another beer or more food, we seemed to migrate right back to each other. Sure, she was probably doing it because I was the only one at the party that she knew, and I did likewise because I found the petite star to be devilishly attractive, but I’ll take it.

“Another drink,” I offered during the next commercial break, getting to my feet.

“Lead the way good sir,” Anna replied as she followed me into the kitchen.

“So you said I gave world-shattering pussy licking,” I asked her as I filled her cup. “Now correct me if I’m wrong, but we’ve never hooked up.”

“Well that part is definitely true, but let’s just say that Hollywood has no secrets. You’ve worked on a bunch of sets and I guess you’ve hooked up with a number of actresses and well…they talk. You have quite the reputation Og, it’s a good thing.”

I knew of the way Hollywood worked. It was how I knew when Anna mentioned how good her head was that it was the truth. A friend of mine, well more of a work collague had hooked up with Anna once at a party then went and told everyone how great she was in the sack, including how he thought she could deep throat, though that detail was hazy given how drunk he was at the time.

“Works for me,” I said with a grin. “So who gave me the glowing recommendation, if I may ask.”

“The two hot vampires,” Anna said as she accepted the beer.

“Kristen and Ashley,” I guessed, knowing I had fucked both the stars of Twilight years ago.

“And Anna Camp before she got hitched,” she added, referring to her Pitch Perfect co-star. “You kinda are a slut actually.”

“Hey, I take it where I can get it. Besides, I think you were the one who came up with the terms of our wager tonight missy,” I bantered back.

We continued to chat in between plays, though some friends would interrupt us to ask the celebrity questions. Anna was a great sport and answered all their inquiries with honesty and never seemed bothered by the attention. She was actually really cool, not like the impression you get from a lot of other famous people.

The game was going okay. Seattle was struggling offensively like they do on occasion, however their defence had limited damage to only 7 points despite our QB not completing a single first half pass. Finally we pulled our shit together and tied the game, but it was short lived as Brady marched his time down the field and took a 7 point lead once again.

“Shit,” I swore as they went to commercials after the touchdown.

Then something happened that was unforeseen, as if the bet in the first place didn’t come out of left field already. As Anna started to rub in the lead, a commercial for some type of cell phone game came on the TV. The Super Bowl is known for epic commercials and this one was no different, as it cast the gorgeous supermodel Kate Upton.

As transfixed as I was on the TV, so too was Anna. I couldn’t believe it as a subtly looked over at her to see her beautiful eyes glued on Kate, more specifically Kate’s enormous tits as they bounced as though gravity didn’t apply to them within her low cut top.

I kept watching the auburn-haired beauty from the side of my vision and noticed that she all of a sudden began pressing her thighs together…hard. I recognized the maneuver at once, she was turned on and was trying to use the friction from her inner thighs to rub her pussy. I raked my brain and tried desperately to find a way to use this tidbit to my advantage, however it was unneeded.

“So sailer, let’s see how much faith you have in your team,” Anna said to me before the next kickoff.

“What did you have in mind,” I asked, giving her my full attention.

“How about we move up our bet, that way we aren’t bombed at the end of the night and you lacking coordination,” the redhead told me. “I want your A game and this way you can service me at 100% capacity plus drink to forget Seattle losing the Super Bowl.”

“So Kate Upton really did get her all hot and bothered,” I thought to myself. “Well that isn’t the best chance for me now is it? We’re down a touchdown with only half the quarter to go.”

“Hey, if we were reversed I would have enough faith in my team to pull off the bet but if you think your team is so inferior then…”

She was baiting me, I knew it and so did she. But fuck did it ever work. And hell, even if Seattle didn’t pull it out then I could still say that I got to hook up with one of the biggest crushes I’ve ever had. Plis, I was going to try to parlay the bet further.

“Okay, on one condition,” I added.

She smiled, satisfied that New England would hold out Seattle’s sluggish offence from the endzone and thus get to be eaten out to a great and overdue orgasm.

“And that is…”

“If I lose then we have a bet available for the second half as well. New terms but same bet…some type of sex for our own team to win.”

“Hmmm…I guess I can live with that,” she said as we shook hands again to make it official.

The rest of the half went by fairly quickly. Anna was smirking and smack talking twenty people all at once, though seemed to always have time to throw in an extra sting in my direction. Seattle wasn’t faring too well in the game, and with only 31 seconds left in the half they were still down 7 and 80 yards from the goalline.

“Better warm up that jaw of yours,” Anna said so only I could hear her.

I wish I had a snappy comeback for her, but I didn’t. Seattle was resigned to going into halftime losing, which meant I didn’t get to receive Anna Kendrick’s amazing blowjob. Still, being forced to be between her milky white thighs, licking every inch of her twat wasn’t exactly a punishment either.

However, Seattle started to march. A long run by BeastMode followed by 3 passes by the quarterback had my Seahawks only 10 yards out from the goalline. We all watched on as with 2 seconds left on the halftime clock, a receiver who hadn’t caught a pass all year rose high above his marker to make the grab and score the tying touchdown.

We hadn’t thought of the event of a tie game, as when we first conceived the bet we meant for it to stretch for the entire game where there was always a winner. But now that it was all square at the half, we had definitely both won, or loss, but I chose not to think of it like that since I wanted something, anything, to happen between the two of us.

“Would you care for an actual tour of my place,” I suggested to Anna, loudly so everyone could hear.

I didn’t really give a shit about showing off my house to the beautiful girl that I was able to call a friend for the past bunch of years. However, the guise of a tour would be enough to allow us to slip away from the pack of people without them asking too many questions about our hopefully prolonged absence.

“Yeah I guess I was kinda shitty and only showed up right at gametime,” the actress replied.

I helped her to her feet and then we walked around some people as we made our way out of the main room. She’d seen the kitchen already so I showed off the backyard, though didn’t go outside given that there were some smokers out there and I didn’t want to be delayed.

“And is this where the magic happens,” the redhead asked with a grin.

“I would never be so corny as to ever use that line,” I replied, bringing a laugh from her.

“So what’s the verdict Og,” she asked me.

“Well in my opinion, there are no losers out there. I saw we both get what we want,” I proposed.

“Normally I’m not a fan of giving every kid a ribbon even for participation but I like that I’m hearing. Continue.”

“We could 69 I suppose,” I suggested, but my heart wasn’t in it.

There were several problems with that idea. Though it would feel great to have a cock in Anna Kendrick’s mouth regardless of the circumstance, she would be distracted, thus I wouldn’t get the true experience. Based off what word around film sets and Hollywood in general was, Anna could really suck a dick. Not like most girls who were good at it, but Anna had a massive reputation when it came to hummers and I wanted the fully monty, not a half serving.

“Meh,” she replied with a grimace on her face. “Sure it’s probably the act that makes the most sense given the game, but you won’t get my best and I won’t get your best so really, what’s the point?”

“Hmm…I got it,” I said after a few seconds of reflection. “I will graciously go downtown on you first…”

“Such a gentleman,” she joked.

“If you have boobs out during your turn.”

“Interesting,” Anna said as she thought over my offer. “I can except those terms.”

Anna was now seated on my bed, which I was happy that I had the forethought earlier to make when I got out of bed this morning. She extended her hand out to me to seal the deal like we had been doing all evening with bets and deals, but I had something more intimate in mind.

Stepping towards my bed I bypassed her outstretched arm and got right up close to the large-chested woman. Anna’s eyes went wide for a moment in surprise with my sudden action, but she got past the moment and licked her lips in anticipation.

I leaned in and hoped I didn’t push things too quickly with her, but as I neared her, Anna pushed her head forward. I was worried that the moment would have revealed that we lacked chemistry, but we both twisted slightly our heads to opposite sides so our noses didn’t butt against one another. Our  lips pressed against one another and held, allowing us to get a feel for the other. Though I was the first to initiate the kissing, it was Anna who was the first to open her lips and push her tongue into my mouth, which I eagerly accepted.

“Fuck, should have realized you were a good kisser too,” Anna complimented, a good minute after we had started.

“Right back at you sexy,” I quickly added.

We caught our breath for a few moments before I leaned back down and lissed her hard again. This time we were more familiar with one another, not to mention more sexual hormones were flowing now, and we hungrily and passionately kissed each other. My hands immediately went to the side oher head, lacing into her hair as her’s did likewise.

With her sitting low on my bed, I hunched over more to give my hands better access to roam her tight body. As we continued to mingle our tongues in the space created by our lips, I moved the palms of my hands downward only a short distance until arriving at her insanely large tits and gave them a firm squeeze. This seemed to bring a squeal of pleasure from the redhead so I gave them another hearty knead before running them down further over her flat stomach.

We continued to kiss with emotion that I didn’t know two people could experience so strongly. It wasn’t just because she was a celebrity, but because I had wanted this girl for 7 years, whether I was fully aware of that fact or not. And now knowing that anna had felt the same about me made it even better.

Over course I didn’t leave rubbing her tits just to feel her stomach, as my goal was clutching the bottom of her tight football jersey. She knew exactly what I had in mind so as I lifted her shirt upwards, the talented singer rose her arms straight above her head to allow it to be pulled free. I made equally short work of her bra in order to reveal her large tits for the first time since knowing her.

They were even better then she had been imagining for the past 7 years. Huge for her size, perfectly round and suspended firmly in front of her with the cutest pink nipples, I had to remind myself to swallow and not drool. Having stopped making out with her to observe the fine specimens, I leaned back towards her, taking her left tit in my hand and began sucking. Anna wasn’t surprised by his focus being solely on her tits now, most men she had been with did the same, but what did catch her by complete surprise was when I bit down on her now erect nipple.

“Aawwhh,” Anna screamed sharply.

It was a risky move to pull on someone when we just started to hook up, but with Anna I felt like I needed to be different and live up to my apparent lofty expectations. I knew it would hurt her at first, but then I could feel her relax again, allowing me to sigh as now I knew it felt good after the initial shock.

I released my grip after a few more second then slide to the other boob and did the same there. She yelped again then followed it up with a chorus of moans. I could tell that she was upset slightly when I unclamped my lips and teeth from her impressive mounds but it was only so that I could wrap my arms around her petite frame and lift her off my bed.

Out of reflex I imagined, she immediately wrapped her jeans-clad legs around my waist to make sure I didn’t drop her, which would never happen. It helped that she weighed maybe just over 100 pounds, but it had to do with the fact that I was a monster. I stood roughly 6 foot 1 inch, but I was bulky and enjoyed working out, making me look like I played professional football for a living.

I didn’t intend on holding her for very long either as I only planned on laying her at the top of the bed with her head on the pillows. As I got my knees on the bed and lowered her down again, laying her flat on her back, she unhooked her ankles from behind my back and found my mouth with her tongue again.

“My God you’re sexy,” I said, having broke the kiss and looking down on the topless girl.

She reached up and took my head in her dainty hands as she kissed me again, though I didn’t intend to stay in this position for long. Still propped up on my knees and hands, I steadied my weight on one arm while my other went down her body, squeezing her massive tits of course, until my fingers found the bottom of her jeans.

“I’ve wanted to for so long,” she moaned.

Anna knew exactly what I wanted to do as she hiked her hips up, lifting her slender but cute little bum off my bed. I took advantage of her assistance by using both hands to grip the top of her pants and pull them down. They were practically painted on her slim legs but my gym-carved strength was easily enough to overcome that and they were off her altogether.

“Me too,” I breathed.

Now finding myself sitting back on my knees, I realized I had pulled her thong down her legs with the pants. Now completely naked, I looked over and observed the sexy actress. Her legs were slender, making her petite frame look even smaller, matching well with her narrow hips. Her stomach was flat and led into her bright pink snatch, made all the more observable by the fact that her pussy was shaven bald, which made my mouth water.

“Like what you see,” the girl asked.

Though Anna was normally a cocky person, she was well aware that her body was ridiculously amazing. Her legs may not be everyone’s cup of tea, but the combo of a nice round ass, bare cunt and overflowing tits made a lot of men cream themselves early. Looking up at me from the top of her bed, she bit her lower lip with the sexiest look I could ever imagine her making.

“Very much,” I said, leaning back in to kiss her.

While shoving my tongue into her mouth with some finesse, my fingertips brushed down her amazing body, lingering over her large mounds. Begrudgingly I left her best feature, roamed over her flat stomach and bare patch right below until I dropped down and felt wet folds sliding past my fingers. Presumably out of reflex, Anna thrust her hips slowly forward, essentially trying to fuck my hand. Of course I didn’t need the help as the second of my fingers touched her moist heat as I drove a solo digit as deeply as I could inside her.

“Oh God yes,” the beautiful creature screamed.

Anna’s moans became stifled when she grabbed the back of my head and pulled me even harder in for more kissing. The tiny actress linked her arms behind my neck so that she could deepen the kiss. Her tongue flashed inside my mouth but would be needed to frequently groan and moan as I continued to slowly pump inside her twat.

“I’m gonna need you to break your superhuman grip on my head,” I told my dream girl while working a second finger into her unbelievably tight snatch.

“And why on Earth would I do that?”

“My tongue and your pussy getting to know each other better,” I answered bluntly.

Anna couldn’t help but sigh with disappointment when my fingers pulled free from her dripping pussy. I gripped both hands on her inner thighs, widening them as far as possible to allow my massive frame to fit between them. She responded immediately and did as I prompted without fighting, so I slinked down her petite frame, my mouth finding her nipples again as I descended.

“Mhmm…yes,” she groaned again.

Without hesitating any more I leaned my head inwards and felt my stubbly face brushed against the soft skin of Anna’s inner thigh. Her hands immediately reached down to rub through my inch-long sandy blonde hair, not to pull me away but just to have more contact with me. Not waiting any longer I stuck my tongue out and ran it along the entire length of the pretty girl’s slit.

“Ohhh…mhmmm,” Anna screamed.

I was pleased when her fingers tightened in my hair, pulling on the follicles as she already began to thrash above me on the bed. I didn’t want to blow her mind too quickly so I slowed it right down, using my lips to kiss her lower lips. It had the desired effect as the redhead settled back onto the bed, allowing me to continue working over her pussy without restraint.

Of course her wanting to take control reared it’s head again when I crammed my tongue into her snatch with surgical precision. Her hands reached down once again and clutched the back of my head in an attempt to get my tongue to drive even deeper into her very wet snatch.

However, I wasn’t going to let the feisty Pats fan work my like a puppet, albeit one very good at going down on women. My reputation was well earned and was happy to hear that women talked favorably of me as I was quite an accomplished pussy licker, so I wasn’t going to let the talented and sexy actress call the shots tonight.

I was able to reach a hand between her thighs, which Anna was using to squeeze my head in spasmodic episodes when one of my maneuvers filled her with too much pleasure. My fingers spread her pink lips apart to give me clear access to her clit, which was standing in clear view for me. The first time my tongue flicked over the concentrated bundle of highly sensitive nerves, her lithe body went rigid from the intense sensation.

“Awwwhhh…shitttt,” Anna cried out, louder than ever.

“Thought you might like that,” I told her, other hand snaking up to squeeze her large right boob.

I wasn’t just going to talk to her while I did my damnest to give her the best rug munching of her life so I got right back to work. My tongue went back into her slit, licking as deep inside her twat as I physically could. She tasted as good as I could hope, sweet with a touch of acidity, which made me more than happy to linger as long as I could inside her honey pot.

I didn’t forget the response I got from attaching her sensitive bean so after another minute of deep licking I withdrew. Any disappointment from me leaving was soon dispelled as my tongue was replaced with two fingers, easily sliding inside given the amount of wetness she was flooding outwards. Her moaning was increased to a high volume once again when my tongue moved north and found her clit, giving it several lingering licks before I latched my lips around them and assaulted the nub with both suction and my wet muscle.

“Oh sweet baby Jesus!”

Now I knew that I could keep up this technique, constantly alternating between fingers in the snatch with mouth at the clit and vice versa, but I wanted to give her my full arsenal of tricks. With my index and middle digit plunging deep into her twat, sliding along her G-spot before withdrawing and repeating the process, I let my 5th finger hang down. Over the course of a minute it had first landed on her left ass cheek then migrated down until it was resting right over her backdoor with the faintest of contact.

“Living up to my reputation,” I asked.

“Mhmmm big boy,” she replied, body thrashing about.

I noticed that even with the slightest of touch against her asshole, Anna didn’t back away. Instead she continued arching her back and flopping around on my bed as I ate her out superbly. With the waters tested and seeing that she wasn’t repulsed by some anal play, I had my game plan settled on.

“Whoa,” Anna screamed.

The response was a direct consequence of me having grabbed her narrow hips and flipping her 180 degrees over. It pained me that her tits were now covered, being pressed into my bed, leaving me unable to grope them further, but it was all part of the plan.

My fingers, which were withdrawn from her sopping wet pussy to roll her over didn’t go back into her twat, instead that honor went to my tongue. My hands were being used to hold her hips steady, and occasionally to run up along her spine, making her arch back into my mouth further.

My motives for the change in position was so that with my tongue buried deep in her wetness, my nose was pressing directly against her asshole. It could have been a risky move for both of us, but with the water tested I figured she wouldn’t mind plus it wasn’t a direct attack against her booty, able to be played off as accidental contact in case she was super protective of her backdoor like a good amount of women were.

Anna was not one of those girls. My senses were on heightened alert for even the faintest of responses when my nose touched her, but they didn’t need to be as the moan she let out as my tongue buried in her snatch at the same time was almost the loudest of the night.

The adorable redhead was on the ropes right now and I figured now was as good a time to finish her off as there ever would be. I had been going down on her for nearly 15 minutes, she still had to do me and we both wanted to catch the start of the second half of the football game after all.

Even though I had tested the waters progressively, both with a soft finger pad and ‘accidentally’ with my nose, this was the hail mary attempt now. It was a risky move, as I’ve blown a few one night stands with being too rash, but those that liked it tended to cum harder then they ever had.

Having done drums in high school music class I was able to keep beat with three different body parts. For drums it was left hand, right hand and foot, while with eating a girl out it was both hands and tongue. Moving my hands from her hips down to her pussy, Anna was responsible for keeping her face in the pillows and ass in the air so that my left hand could rub her clit while my right hand buried two fingers into her twat.

“Oh fuck….oh fuck…oh fuck,” she swore.

“Getting close,” I asked rhetorically.

“Mhmm,” she moaned in response anyway.

I took one last deep breath, steeled any last remaining nerves and took sight of my target; her cute-as-a-button asshole. Leaning my face in, I could feel my stubbly beard light scratch the bottom of her adorable ass cheeks as I stuck out my tongue and placed the tip of my tongue on her ass. I made the contact as broad as possible to only lap at her hole rather then trying to jam it into her kester, which may have caused a defensive reaction.

“Awwhh….mmhmmm…ugghhh,” she moaned in response.

“Gotcha,” I thought. “Cum for me baby.”

I knew I had her now and she would be cumming in short order. With a triple stimulation going, not to mention her sensitive nipples rubbing against my bed sheets, was easily going to make her orgasm, and my bet was within seconds rather than minutes.

“Keep going…almost there,” she beaconed.

Then it was her turn for the surprises. While I continued to lick her crinkled rosebud, Anna snaked one of her arms backwards so that she could clutch the back of my head. This was unexpected and I was thinking she was going to push me down, back to lap at her clit or in her twat, but instead she pressed my face further into her ass.

Figuring what she wanted I made my tongue pointy, braced it with a strong jaw and did more then lick her. This time I was trying to force my tongue into her backdoor, and I had some success as I felt her sphincter give slightly, just enough to be able to lick around the very entrance to her asshole. This, apparently, was more then sufficient for the talented actress and singer.


With a loud scream that surely everyone in the house, if not the neighborhood had heard, Anna came all over the fingers I had buried deep in her pussy. Apart from feeling her gyrating body go rigid, and the added pressure in her twat, I could also feel her asshole quiver as she came, allowing me to briefly lick all the way into bowels rather than just rimming the hole, however that was short lived.

I knew my time between her thighs was over and that any more effort tonguing her asshole would be potentially negative so I withdrew my mouth and fingers from her holes. Instantly, as though I alone was holding her upright, she flopped down flat on her stomach, her ass jiggling in the process. Still close to her smoldering sex, I really wanted to taste her right from the source so I dipped back down and licked deep in her twat, tasting her lady cum.

“Sorry, couldn’t help myself,” I said with a grin.

Anna flipped herself back over at this point, giving me another long look at her amazing tits. She looked at me with a stunned expression then ran a hand through her long hair, much like I had seen her do countless times in the movies as she played awkward characters.

“What,” I asked after 10 seconds of her just staring at me.

“You…I mean…fuck! That was absolutely fucking amazing,” Anna complimented.

“I’m glad to be of service,” I replied with an exaggerated bow.

“Oh you were,” she said, rocking up to her knees to be at a similar height to me. “How’d I…you know…taste?”

“So good,” I replied, aware that I probably had wetness still around my lips and mouth.

In a move that surprised me, the tiny actress reached down and grabbed my thick wrist in her hand. While her dark lined eyes held my gaze without blinking, Anna lifted my arm so that my hand was level with her face, opened her mouth and proceeded to suck on the fingers that were buried in her cunt while she came seconds before. I could honestly say that my cock physically hurt with the amount of blood currently filling it as she worked her skilled tongue around my fingers.

“I really do taste good, don’t I,” she grinned, licking her lips. “Now get that shirt off.”

I didn’t hesitate listening to the songbird and immediately reached down to the bottom of my jersey to pull it over my head. She too was busy, making short work in her naked state of my belt and jeans, having my pants slack. We had surprisingly good chemistry for a couple hooking up for the first time as she cued me wordlessly to sit on the edge of the bed. As I got into position she skillfully removed my pants, leaving me nearly as naked as she, except my boxers remained.

Anna leaned in to kiss me one last time before she began a trail of kisses down my neck, and over my powerful chest, at which point she slunk herself onto the floor, settling on her knees between my powerful thighs. Her tiny hands found the waistband of my silk briefs and pulled them over the tent that had propped them up, exposing my cock to her for the first time.

“It’s…wow,” Anna exclaimed.

I wasn’t a cocky person, but I was rational and knew that I was well endowed when it came to my dick. Standing a solid 8 inches long, it was also girthy to the point that one ex-girlfriend said it was better than most cocks in porn. Having seen the odd video myself, I was forced to agree with her assessment. Apparently Anna agreed as well, as the look of joy on her face and the way she licked her lips in anticipation told me that she was pleased with what she had to work with.

Despite her reputation, which was glowing when it came to sucking cock, she didn’t dive in and blow my mind right away. Leaning in, the little redhead puckered her lips and kissed me right on top of my tip with softness. To continue her teasing she kept that tactic and moved down my shaft on one side, then kissed her way back up to the top again, which was driving me absolutely insane with lust.

I was on the verge of begging her to suck me with earnest, but she must have read it on my face, and it must have been what she was after. Anna wasted no time in opening her mouth as wide as possible and taking easily half of my good-sized length between her lips.

“Holy fuck,” I exclaimed as her moist heat worked its way over my shaft.

I couldn’t help but look down and observe Anna in what looked to be her natural environment; on her knees with a cock in her mouth. After taking half of me in her mouth she planted her lips completely around me and bobbed her head back towards the tip. Her mouth felt warm then I imagined and the way her lips dragged along my skin made me want to pump her full of cum right then and there.

“If you liked that,” she said with a glint in her eyes. “Then you should really enjoy this.”

I continued to watch her, especially after her cryptic words and felt as my bulbous head touched the back of her throat. It was usually at this point most girls coughed a little bit then rapidly withdrew my dick from their mouth, but Anna was not most girls. The slim redhead kept moving forward until my tip slipped into the tight confines of her throat. She continued to drive more meat into her mouth until her cute nose was buried in my trimmed pubic hair and her lips were wrapped around the very end of my pole.

“Sweet Mother of God,” was all I could groan.

It felt better then any other blowjob I had ever received and it was only the first minute. I’ve had the odd girl that could do what Anna was currently performing but this was different, better. For one those few other girls weren’t Anna Kendrick, the adorable yet sexy actress that I’ve wanted for years. Plus she had more flair and theatrics which really heightened the atmosphere.

It also didn’t hurt that she was stimulating more than just one sense, she was doing three which brought things to a new level as well. Her lips and throat felt great on my shaft as she bobbed on my whole length over and over again, while she was more than fine with letting me look down and watch her talent, some other girls were weird about that. However, hearing the gurgling noises as Anna gave me that great blowjob was truly remarkable. The noises only increased in volume and frequency as the large breasted woman went from slowly and methodically taking my entire cock into her throat to ramping up the speed greatly.

“Fuck yes,” I couldn’t help but groan.

“Grab my head,” she somehow was able to speak before descending back down on my dick.

Anna took her hands from holding up her slim upper body to placing them on my hips so her fingers were pressed against my firm ass. Her small but toned biceps bulged as she held herself up in that position with her mouth still on my cock. Although she was only able to move her lips over me a very short distance, it gave this Seattle fan the ability to have complete control over her.

To say I was impressed with the tactic of the busty girl would be an understatement, and I was more than willing to take advantage of the unique opportunity. Anna had already showed off her gift of being able to take my whole dick in her mouth so I had no problem with face fucking her, which was clearly what she wanted to happen.

I would have jumped at the chance to do this with anyone, but with this particular redhead made it all the better. That was because Anna’s face was how I would describe perfection; cute but still sexy with just a hint in her big bedroomy eyes that she’ll do whatever nasty shit in bed that you’re into.

Grabbing the sides of her head, I began pulling her towards my lap slowly until I could feel her nose touch the lower portion of my abdomen. The feel of her lips gliding around the very base of my dick was beyond words and after I took a moment to marvel in the occasion I retreated her along my length until only the tip remained in her mouth.

“Glluuuggghhhhh,” Anna gasped as air filled her lungs again.

I allowed her a moment to regain her composure and some air while also taking the chance to wrap my monstrous hand in her long red hair with my other hand going to rest on the side of her face. She wanted me to have full control of the blowjob and that is what I planned to do.

With my new grip, I began the same method again but this time I could feel Anna pulling my hips towards her as best she could. When I looked down and saw her flash me with her large eyes, she pleaded for me to go faster. Whether it was her visual cue or the wave of horniness I was getting when looking down on her with half my meat pole in her mouth but I retracted hard on her head and sent her face crashing into my stomach.

“Gggulllllggkkk,” Anna coughed as spit slushed in her throat.

With any other girl, I would have bet dollars to donuts that spit would have been dangling from their mouths and covering their chest. However Anna was different. Probably cognitive of the fact we had to rejoin the party after blowing me, she appeared to be spending a good deal of focus to continuously slurp back her own spit as I pummeled her throat with my pole.

“This…your mouth…is great,” I eventually said after another 5 minutes of face fucking the beautiful girl.

It came at a great cost though. As much as I would have liked Anna to have sucked on my cock all night, I knew that was a pipe dream. The fact was, I needed to cum soon, however I would dare anyone to try to last longer then this if they were working with what I was dealing with.

“I’m cum soon,” Anna asked.

She probably summarized that when she felt my grip of her hair and face slacken. She used that to pull free of my dick and move further down, really sinking onto her knees and getting her face beneath my tool to where my full balls dangled. Opening her mouth, she didn’t beat around the bush at all, taking them within her warm wetness.

“Fucking close,” I groaned with eyes closed, thinking of ways to prolong my orgasm for as long as possible. “Where do you want it?”

“Cum in my mouth,” she stated matter-of-factly.

As soon as the words left her mouth her lips went right back to being wrapped around my sack. It wasn’t like she was neglectful of my cock or anything, her hand was blazing up and down the spit-soaked pole with blinding speed as she beat me off. I did my best to starve off my climax but it was a losing battle so I reached down to guide her head back to the prize.

Anna took the hint immediately, knowing time was of the essence and wrapped her lips back around my meat. I pushed her head down one last time, feeling her constricting throat muscles squeeze my cock for all it was worth before withdrawing so only my head remained in her mouth. She took control of it from there, closing her lips tightly around my crown and sucking for all she was worth.

“FUUCCCKKK,” I swore loudly.

I could my cum exploding out from the tip, streaking on to Anna’s tongue just as she wanted. The first few squirts were pressurized and I could imagine them jetting to the back of her mouth while the rest of my goo poured right out onto her taste buds, coating them in my salty load.

Instead of swallowing or spitting the cum right away, Anna surprised me a final time by pushing her head down into my lap once more. I nearly came again, if I had anything left, when my dick disappeared back into her throat and was hugged on all sides by her vocal cords. After what felt like an eternity, but what was probably only a few seconds, Anna withdrew me completely from her mouth and then in a dramatic fashion, so I knew exactly what she was doing, swallowed my entire load down in one audible gulp.

“Yum,” she said as she smiled up at me from her knees.

We were both exhausted and sexually spent but as we took a few moments to collect ourselves we heard from my open bedroom window someone shouting at the smokers below that the game was about to restart. Anna and I looked at each other one last time then sprang into motion, sorting through the clothing for our own and getting dressed with haste.

We threw the clothes on then Anna gave herself a look in the mirror and noticed her crazy, wild hair. She took a few seconds to pat it down as best she could, but she knew it wouldn’t return down to it’s normal smooth look. I opened the door for her and we rushed down the stairs and entered the living room just in time to see New England kicking off the half.

Of course, at our reappearance we were greeted to a round of applause by the rest of the party, who had clearly heard our theatrically moaning and screaming from up above. We both flushed red in the face, but our embarrassment wasn’t enough to stop us from getting back into our seats and watching the second half unfold.

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Re: Dating Anna Kendrick
« Reply #1 on: November 27, 2019, 11:28:28 AM »
Title: Dating Anna Kendrick Part 2 - Alison Brie’s Repayment
Celeb: Alison Brie
Codes: MF, Oral
Disclaimer: This is an act of fiction. I do not know Alison Brie at all and this scenario did not actually occur. I make no money from this story.

Summary: A continuation of Super Bowl Bet with Anna Kendrick though you don’t have to read that in order to understand this story. Anna calls her kinda-boyfriend Og to help her out by picking up her friend Alison Brie at the airport.


I was laying around at my house when the call came through to my cell phone. I lived just across the Canadian border in a big city, well in Canadian standards, in Vancouver. I was from the States, in particular Los Angeles where my parents were and still are important in the film game. Though most people blamed nepotism, I also work in the industry behind the scenes just like them, but doing more assisting work and production rather than producing shows and movies like my parents.

I looked down at the caller display and saw a name that instantly made my face light up in a big smile. That name was Anna Kendrick, a girl I had been friends with for years, nearly a decade, before we finally hooked up when she came to my Super Bowl party back in January. We’d meet years before when I was working as an assistant on the Twilight movies and had remained in contact. Finally, over a silly sexual bet, we had gotten together, first with only oral sex, then later actually doing the horizontal shuffle. After that, we had hooked up several times a week as she spent 4 weeks in the area filming a movie.

“Hey Anna,” I said as I switched on the video chat option.

“Sup loser, long time no chat,” she replied, wearing shades as she sat in what looked like an outdoor cafe.

“We talked last night after you landed back in Hollywood,” I reminded her. “Man, coke really fries your brain like they say on those PSAs.”

“Screw you Og,” she laughed, calling me by my actual nickname, though she often resorted to using loser as well.

Just to remind everyone (in case you haven’t read/forgot the first story in this universe), I was named Ogden by my wealthy parents nearly 30 years ago and most of my friends shortened that and simply called me by my nickname Og. Naturally that drove my parents crazy, especially my overbearing mother, but thus I digress.

“I’d much rather you screw me actually,” I joked. “Especially since you went back home I have a feeling that I’ll be doing most of that myself though.”

“I know, I’m sad I had to leave too,” Anna said, actually showing disappointment on the portion of her face that was visible. “But we had a lot of fun…and I’m sure I’ll find myself up the coast soon for some reason or another.”

“Likewise,” I replied. “I could always justify a trip to see the parents and maybe sneak over to your place…”

“Mmhmm, maybe break in, tie me up…”

“And make sweet, dirty love to you all night,” I finished, smiles plastered on both of our faces.

“God I miss you…and your giant cock and talented mouth,” Anna huffed in more frustration.

“Right back at you. I know you only just left but I’m so fucking horny,” I told her.

“That’s actually why I’m calling,” the actress said, taking the conversation in a lateral step. “Can I ask a favor of you but I think you’ll end up being more than compensated for your time.”

“Now I like where this is going,” I said, perking up.

“You will, though no guarantees…though with her it’s as close to a slam dunk as you can get,” the Pitch Perfect star rambled.

“Less beating around the bush and get to the point,” I demanded, snapping the adorable girl out of her spiral.

“Right okay. Well the favor/bad news/part you won’t want to do…”

“Anna! Get to it or I swear the next time we get together I’ll fuck you so hard you won’t be able to sit or walk right for a week,” I shouted the threat.

“And that’s suppose to deter me,” she said with a confused look. “Anyway, would you be able to drive to the airport tonight to pick up a friend of mine?”

I was a little taken aback by the question, only because I was expecting something more complicated. I know why she was building it up to be bad, after all no one likes driving to the dreaded airport, even when it was to drop off a loved one. Now she wanted me to do it for a complete stranger, however it was for Anna who was kinda, sorta my girlfriend or regular booty call or whatever the fuck we were.

“Okay I can do that,” I replied, checking my watch. “When?”

“Have I mentioned how gorgeous you are? Oh, and how big your cock is? Yeah men love compliments on that type of thing,” she replied, expertly dodging my question like a seasoned politician.

“Actually yes, you have.”

“Can I tell you who you’ll be picking up first,” Anna asked.

“When Anna,” I demanded.

“Okay this sounds bad Og but it’s at 1…forty-five…am,” she finally revealed.

“Hell that’s early,” I swore, running a hand threw my close cut sandy blonde hair. “Really early.”

“I know I know, but just think about what I’m willing to give up for it,” she replied, sliding her sunglasses down far enough so I could watch her wink.”

“No offence Anna but I’ve fucked your ass already, how much more can I really do,” I told her.

“Oh Og, you are adorable. That’s just the tip of the iceberg,” Anna countered.

I took heed of this comment, actually so did my cock. I could feel my pants begin to tent at the sluttiest sentence that my quasi-girlfriend could have said. While it was very true that we had done a lot of stuff together in bed in our month together, the promise that it was only the tip of the iceberg had me very excited. So much so in fact, that I completely forgot to ask who I was getting.

Anna and I had continued to chat for the next 5 minutes or so about potential bedroom activities that we could do together, and I was surprised to find that the skinny actress had no filter. It seemed like any of the ideas I threw out, including threesomes to orgies to public sex, which was a particular kink of mine, were fair game.

One of the reasons that Anna knew it was a tall ask for me to do was that tonight was Thursday night. For most people this had little effect, but for me it was the night that I went out and grabbed a few drinks with some friends. She knew that and knew that we tended to close down the bars, mainly because Thursdays were my Fridays, I had no work the next day. This meant I couldn’t get drunk and walk home like my normal Thursday entailed, however when it came to do a favor for Anna, I was pretty chill about giving up my drinking night.

By the time I realized my folly was too late. After I hung up with Anna earlier in the evening, I texted my buddies and told them I couldn’t make the bar tonight. I could have gone for a little bit, but I didn’t have great self control so only reserving myself to a few drinks over the hours I would be there was too risky.

Instead, I cancelled on them and told them I’d be good for tomorrow night instead after our pick-up football game. They made me agree to pay for the first round, but that wasn’t too steep of a punishment, besides I made a good living and well, if I ever needed money more parents were more than willing to help out.

I eventually went for a shower to help stay awake, as I always felt shitty when having a nap this late at night. While I was getting refreshed by the warm flowing water, a text came threw to my cell phone from Anna, detailing the flight number, arrival time and gate I should be at. I didn’t get to my cell right afterwards either, as I took my time getting dressed and then even cleaned the bathroom, something I was usually too remiss to do.

Text: Anna Kendrick. Time: 12:01

Thanks again cutie. You’re the best. Even using long form of words for you, not just single letters.

Text: Anna Kendrick. Time 12:31

Hopefully you didn’t fall asleep…or at least set an alarm. I’m gonna be asleep so phone on do not disturb. Talk tomorrow.

“Shit,” I swore, having seen the messages.

It wasn’t a big deal, but it would have been nice to know which of her friends I was picking up. The star power of the girl, or guy potentially, wouldn’t have awed me given my career in the movie and TV industry, but it would have been nice to know there name. There was a good chance that they weren’t even famous, so what would I call them? Anna’s friend? How personal.

I did a little more tidying around the house, nothing major just some general clean up, loading the dishwasher and picking up any loose clothing from around the house. I still had 20 minutes to kill so I considered booting up the game console, but I didn’t want to get into anything too serious so instead I headed out.

At that time of night on Thursday there was hardly any traffic so I made most lights and before I knew it I was pulling into Vancouver’s vast airport. Karma was on my side apparently, as one of the parking meters in the short-term lot was out of order so I was able to snag the spot for free.

“Maybe they will have free coffee inside too,” I mused as I headed into the large building.

It was a simple joke to myself, but before I knew it there was a small paper cup in my hand filled with hot, surprisingly good java. One of the big chain shops in the country had their annual deal of a free small coffee for the entire week. My way to work amazingly never went by one of the cafes so I was unaware, despite their numerous ads.

“Pick up a sexy girl’s friend = good karma all night long,” I thought to myself.

I checked my phone again and noticed that I was ten minutes early so I got up the text message and checked the gate and flight number. My good luck held and I looked on the screen and saw that not only was the plane from Los Angeles on time, but it had already landed roughly 15 minutes ago. The gate wasn’t far so I made haste and before long I was taking a seat with my drinkable coffee and waiting for a woman to come up and identify me as her ride.

“Og? Ogden?”

It had barely been 2 minutes, hell I had only taken a few sips of my coffee before the somewhat familiar voice called my name from 3 feet in front of me.  The reason why I recognized the voice, despite never having met this girl before, was because she was in one of my favorite comedic shows. I started watching Community because I was a Chevy Chase fan but the group dynamic of the younger cast was dynamite and had me coming back for more…and because Annie Edison, played by Alison Brie was adorably sexy. Now that I was staring at her in the flesh, I could definitely confirm that she looked even better then on screen.

“Holy shit,” I couldn’t help but say. “You’re Alison Brie.”

“I think you said the quiet part loud and the loud part quiet,” she assessed before laughing at me.

I flushed in embarrassment in my large gaffe. Having been working in the industry for most of my adult life, I was normally a lot better at containing my excitement. However there was something that made me exclaim my feelings having seen who Anna’s friend was. After all, I had a major crush on the Scream 4 star as the brunette was the complete package in my eyes: short, milky white skin, a stunningly beautiful face and massive tits.

At this point I realized I hadn’t talked in a while so I quickly got to my feet and regained some semblance of composure.

“Sorry about that. Can I take your bags,” I asked, extending an arm.

“No I’m okay,” the much shorter girl answered.

I looked at her and cocked my head at her while giving her a face that let her know how ridiculous of an idea that was. My facial expression was able to portray what I was thinking, specifically that she had 2 bags that were pushing the airline’s limit of 50 pounds each plus a medium-sized carry-on and a purse. Then there was the fact that she had spent 3 hours stuck in a tiny chair and the fact she was a mere 5’2 and maybe 110 pounds while I stood a significantly amount bigger; 6’2 and pushing 200 pounds.

“Come on, pony up the bags,” I insisted. “It’ll make me feel better about gawking a minute ago.”

“Yeah okay,” she relented with a pleasant smile. “Anna did warn me you were a gentleman.”

“Hopefully she only told you good things about me,” I said as I led her on a short walk until we exited the terminal and hit the crisp night air.

“Very good things only,” she said in a tone that was clearly flirty.

As I looked over at her as we waited for a car to pass before crossing the street into the underground parking lot, I noticed goosebump that appeared on her creamy white legs, which were numerous given her choice of wearing a mid-thigh length skirt. Although Vancouver didn’t get stereotypical winters like other parts of Canada, it was only a seasonal 68 degrees tonight and had a bitter wind coming off the ocean to boot.

We continued to walk while I kept stealing glances over at her. I hid them well, turning my head to face her as we talked about how her flight was and what brought her to my adopted country, though every time she broke eye contact with me to see where we were going I lingering on her body for only another second or two.

Of course I’m sure grabbing the attention of men was something Alison Brie was all too familiar with. Puberty may not have given her a big growth spurt height-wise, however it did wonders to endow the comedic actress with heavy assets in the front of her chest that left her well renowned. Hell, the creators of Community even named a monkey after her amazingly healthy rack. The brunette’s body type was a mix between slim and curvy; no one confused her for being a stick figure as she had some healthy meat on her bones yet she still very much had a petite feel about her.

In addition to Alison’s head-turning C-cups and her altogether amazing body, it was her gorgeous face that was the focal point of my gazing. Her big blue eyes could hold men’s attention after they were done scoping out her cleavage while her sweet smile also had a hint that there may be something naughty under her innocent beauty. She may not have initially screamed that she was a highly sexual creature given her cute appearance, but there was very much more lurking beyond her surface, especially after the brief mention Anna Kendrick had given me earlier.

“This is me,” I told the attractive actress as we approached a medium-sized blue pick-up truck.

“Oh…cool,” she replied.

I couldn’t quite place the tone of her voice as she said that, but I brushed over it without much of a care. If it was my luggage then I would have just chucked the bags over the edge of the cab, instead they belonged to a lovely lady so I undid the back and slide them in with care. Alison thanked me for the care and gave me a little peck on the cheek for my trouble before we circled to our respective sides of the truck.

As I opened my door and couldn’t help but notice that Alison had vanished from sight, only to return a second or two later. I didn’t know what that was about, nor did I really care, she probably just had to fix some article of her clothing. Regardless, the tiny actress was able to step up into the large truck as we belted up before the truck roared to life and we peeled out of the parking space.

“So you landed Anna Kendrick,” Alison said after a minute of silence.

“Ha ha. I guess I did,” I chuckled at her straight forward attitude.

“So Anna told me you really know your way around a pussy,” Alison blurted out nonchalantly after a pause of a few minutes.

“Wow. Blunt,” I replied, caught off guard by her comment. “Guess Anna doesn’t mind sharing personal details.”

Of course, from what I knew about Alison Brie, it shouldn’t have surprised me that much. Much like I had a reputation for my oral skills, as now both the Community actress and Anna Kendrick were all too familiar with, so too did Alison. Hers was based on being a dirty bird, a girl who was up for just about anything sexually, and that had me excited even before her last words.

“I have heard those rumors circulating, yes,” I replied, not wanting to be too desperate, though the idea of pleading for her to show me her amazing tits had crossed my mind.

“She’s a pretty cool chick. Also a big sex fiend which tells me you’re working a serious piece of meat,” she said in no uncertain tones.

Now with a comment like that there were several different ways to answer, which is exactly what the talent actress wanted. I could go all cocky since I could back it up, but I really hated that type of guy so I ruled that option out. Another way was to be all bashful but that could be considered childish so I went with the nonchalant choice, one that would put the ball back in her court.

“I do okay, but I’m not one to brag,” I answered.

“Not a bragger, I can respect that,” she replied, turning to face me full on. “What about being a show-er?”

“Hmmm…I guess under certain circumstances I have been known to let others gaze on it,” I countered, very intrigued as to the direction we had gone in.

“Oh come on, whip it out. You show me yours and I’ll show you mine,” Alison practically begged.

“You mean you got a big cock under that skirt,” I bantered back.

“Witty and funny, just my type,” the brunette said while looking me over. “Seriously though, show that thing off for me.”

It was an interesting offer but I had made up my mind as soon as she put the original offer on the table. Though my cock looked healthy while soft, it was in it’s full glory when erect where it stood a solid 8 inches long, it was also girthy to the point that one ex-girlfriend said it was better than most cocks in porn.

I played up a sigh as though I was in resignation to giving in to her. I slipped my left hand onto the steering wheel, freeing up my more coordinated right so that it could make swift work of my jeans’ button and zipper. I lifted my hips off the seat and slid the denim pants down to my knees, a position that didn’t interfere with my driving since it was an automatic transmission truck. However, instead of pulling down my plaid boxers at the same time, I stopped undressing and looked over at the beautiful girl, whose eyes were glued to my package.

“Okay time for you to pony up. You can see the real thing once you get the ladies out,” I demanded.

“Such a tease you naughty boy,” Alison replied, proceeding to bite her bottom lip.

However, the brunette posted no protect at my request and did as I wanted. She was wearing a floral sundress that showed off her healthy cleavage, apparently it was much warmer in LA when she left then it was here in British Columbia in the middle of the night. However, it was to her advantage as rather than have to get completely naked she simply clutched her fingers inside the dress right above her large tits and pulled the material to the sides. I kept an eye on the road as I gandered over at the stripping girl as the top stretched until finally her naked boobs came popping out and into my line of sight.

“My God, those are perfect,” I exclaimed at seeing her bare tits.

As if to accentuate how awesome her lady bits actually were, the talented actress brought her hands up to her collarbone before rubbing down her body. As her small hands ran over her breasts, which had to be an easy D cup by my fairly reliable estimation, the jiggled while still being supported on the outsides by her dress. As she reached the meatiest portion of her boobs, she contracted her hands in order to pinch her pink areola, causing her nipples to harden promptly under the touch.

“Mhmm,” she groaned.

I wanted so desperately to focus all my attention onto her bare tits, but I knew that it would result in a rollover car accident and I didn’t feel like dying tonight…though I would die a happy man. More than that however, I wanted so badly to dip my head towards her, latch my lucky lips around her erect nipple and suck on that beauty for all I was worth. They were like a pair of tractor beams that were doing their utmost to bring my towards them.

“So fucking hot,” I swore loud enough for her to hear me.

I still had to look at the road every now and then. I was done going threw the somewhat chaotic streets of the airport themselves, but at this point I had to turn the wheel and steer onto the street coming up. I made the right turn onto the road we’d be travelling on for the next 10 minutes, but before I could look back over at her I felt Alison’s moist lips on the nape of my neck and her warm hand reach under my shirt to rub the toned abs beneath.

“Whoa Alison…what are you doing,” I asked in shock. I had to act quickly to the right the truck after a brief wandering into the neighboring lane.

“I’m collecting what I’m due…a view of cock that better be big,” she replied in a very sexy voice.

I still felt the hot breath and occasional kissing of the attractive woman as I dared a quick glance over at my kinda-girlfriend’s friend and saw the look of pure desire draped all over her gorgeous face. Knowing that there was nothing I could do to stop, not that I had a God damn intention of doing something so stupid, so I simply re-adjusted myself in the driver’s seat so that my waist was further away from the steering wheel to allow Alison easier access to what she clearly desired.

“Good decision,” she whispered in my ear before flicking her tongue against the lobe.

I couldn’t help but be disappointed when her hand left my stomach but all was forgotten and forgiven when I felt the car air touch the skin of my groin as the horny girl lifted up the waistband of my boxers. To make things easier I shifted my hips up enough so that Alison was able to wiggle shorts down over my ass enough so that my now erect dick freed itself and smacked against the steering wheel with a dull thud.

“Oops. Sorry about that,” Alison giggled before looking down at what I had to work with. “But seriously, nice cock Og.”

“Awh, I bet you say that to all the guys,” I joked as my cock stood in attention.

I could feel her gaze upon my package as though there was substance to it and couldn’t help to feel subconscious. After all, this was Alison Brie staring at my dick, a big star from Hollywood who had a sexual reputation to make most blush, thus she had seen her fair share of meat poles in her time. And now I knew that she was storing me in her memory back and comparing me to the hundreds (potentially thousands) of other men she’d judged.

“Hmm…did it hurt when it hit the wheel,” she asked me, still close.

“Umm…a little I guess,” I replied, not knowing why.

“Let me make it up to you by kissing it better,” she said which had my cock feeling harder then ever. “Plus to show my appreciation for picking me up.”

Alison was putting a lot of stock in the hope that I was a good driver while getting blown because there was no way she could wear a seatbelt and bend that far down. However, she wasn’t wearing the belt, which allowed the actress shoved her thick ass to the edge of the seat so it was pushed against the side of the door. Now that she had maneuvered her body around, she could now bend over enough to have her face in line with my very erect cock.

“Oh God,” I groaned.

My moan of pleasure was as a direct result of Alison reaching down and lightly running her fingertips down the underbelly of my member from the tip down to my full sack. The mere but very real touch made my cock twitch in excitement and felt as though somehow grew harder than before.

With a grin on her face, Alison made a gentle fist around the base of my thick cock and opened her mouth in a big O. Lowering her head even more, the sexy girl clamped her plush lips down on my shaft, much to my appreciation. With his tip in her mouth now, I could feel Alison swirl her tongue around the crown before descending further down.

Now resting her tongue on the underside of my member, Alison bobbed her head slowly but always making progress downwards so more of my shaft entered her. Whatever couldn’t get inside her mouth she was gently yet firmly stroking with her hand in perfect rhythm with her bobbing head.

Luckily I had already driven past the more populated streets in the immediate vicinity of the airport and was on a road that was relatively straight with much less vehicles. Although my attention was regrettable split, which stopped me from taking in every little subtle detail of her blowjob, I couldn’t remember Alison taking any breaks to breath since she began blowing me. Now aware of it, I focused on that fact for the next few minutes and was impressed to find that Alison was using her nose to get oxygen so that she ever had to unwrap her lips from me dick.

“Fuck that’s good,” I groaned, which was slightly drained out by the loud slurping noises the brunette was making.

I suppose my comments inspired the actress as it felt as though she redoubled her efforts. Pulling her head back so only the tip remained in her mouth, Alison used her tongue to work wonders on my crown. Apparently she was waiting to hear me grunt in approval again before she changed course and now slowly descended back down my shaft until my knob poked her in the back of the throat. She relaxed her throat enough so that she was able to get another inch of my impressive dick into her throat at which point she promptly began to gag.

I noticed that it doesn’t faze her in the least, something she must have been expecting to come so she simply pulled me out of her throat just enough to get air into her lungs. In the process Alison had spat up a little bit so that now my dick was completely covered in a thick layer of her saliva.

“Such a nice dick,” she complimented.

The break in blowing me continued as her hand wrapped around the now lubricated cock and her fist speed along my length as incredible speeds. Without her spit coating mem, I would have been covered with blisters, but the spit-up made the handjob feel amazingly blissful. She brought her lips up to be pressed against mine, at which point I returned the tongue-filled kiss though kept my eyes open to see where we were going.

As she continued to kiss me and beat my meat sword, I realized that this was the first time in close to 10 minutes since she started to blow me that she had taken a break. After kissing for awhile, I assume her swift moving arm was getting tired so before it failed on her, Alison leaned back down and moved her lips from against mine to be used to latch around one of my testicles and began using her tongue on it while sucking it with her mouth. She stopped after a minute to switch so that she gave equal love to each of the large nuts before ceasing her ferocious stroking with her hand and taking my dick back into her mouth.

Whether it was luck continuing to be on our side or the fact it was past 2am on a Thursday night, but we caught every green light on the large street we were on. We still had several more miles and about 20 minutes until we got back to my house, and based on the evidence so far, there was no way I’d make it before she made me cum.

“Is this a busy road,” Alison asked as she darted her skilled tongue at my pee slit.

“Umm…kinda yeah,” I replied, trying my best to keep us in our lane.

“Take a detour onto easy streets,” she instructed. “Privacy and straight.”

She made me use my brain now, all while her lips wrapped back around my shaft and plummeted downward. I closed my eyes and just enjoyed Alison’s talented mouth for a few seconds before racking my memory for a road that would suffice the large breasted woman’s demands. Her mouth was almost completely full of my girthy member when I thought of something, so I drove another mile, all while she bobbed in my lap, before turning from the busy street onto a quieter avenue.

“Hold on,” I told her before I made a series of quick turns. “Okay, smaller street with no more turns for awhile.”

I couldn’t help but be disappointed when Alison moved her mouth away from my cock. Though she wasn’t as good to Anna, then again no one I had ever encountered was as good as the redhead, it was still a hell of a blowjob going on. However, out of the corner of my eye I could see Alison moving around in the seat, where she was now perched up on her knees facing me. The more interesting part about that was her dress being bunched up around her hips, showing off her neatly shaven pussy, except for a thin trimmed strip of brown hair.

“No panties, wow Ali,” I commented, using her nickname that I heard Anna refer to her as.

“Took them off before I even got in the damn truck,” the horny girl replied, which is where she disappeared to as I was first getting my door open back in the parking garage.

“Umm…whatta doing,” I asked. I had an idea of course but she surely wasn’t thinking what I was I hoped.

“Gonna fuck you now,” she said, matter-of-factly. “Try not to kill us.”

I had fucked in a car before, hell I think most kids in high school did since they needed somewhere to do it when the parents were home. However, having sex in a moving vehicle was a first for me, and though I knew it was highly moronic and dangerous, there was no fucking way I was turning down the chance to get my dick wet in Alison Brie.

I did a quick scan out of very mirror and window in my truck and couldn’t see any cop cars, or any other vehicle for that matter around me. I slowed down enough that I could make a sudden stop or last second swerve to avoid anything that came into the street as I prepared to fuck in a moving car.

“Watch the wheel,” I warned.

Alison merely gave me a look that portrayed for me to man up, or some other comment along the same lines. She acted so nonchalant as she crawled to me before spreading her bent legs wide as she got into position of straddling my lap. I had pushed my seat back all the way before hand and thanked my rigorous workout routine for not having a gut because we needed every spare inch we could get in order to wedge two bodies between the driver’s seat and the steering wheel.

Our chests were pressed tightly up against one another but we managed to turn our bodies to opposite sides just enough so that our heads were beside each other, allowing me the ability to look out the front windshield. My arms wouldn’t be of much help in this encounter, as they resides on either side of her womanly hips to hold their own side of the wheel to steer.

“Can’t wait to have this big cock inside me,” Alison stated.

She was true to her words and had her hands down between our legs, fingers encircled around my pole. I wished that I could have dipped my head down and sucked on her nipples and lived within her cleavage all night, but that would have resulted in instant death as the car wrapped around a light post.

“Fuck me,” I swore as she sat down on my tip. “You feel like a God damn furnace.”

“Best fucking furnace you’ll ever know stud,” Ali retorted.

Alison was not finding it too hard to slowly work her curvy body up and down my lap despite the tight quarters. She seemed to be enjoying herself immensely as well, having took barely any time at all to have worked all the way down my lengthy shaft, taking the entire thing into her snatch.

The rumors around Hollywood about Alison Brie were aplenty, specifically about how truly slutty of a girl she was. She had been with the same guy for several years now, but that didn’t stop her from fucking her way through many of the men, and if rumors were to be true, women that she worked with or went to the same party as. Now, as she rode me in a car that I was currently driving, I got the distinct impression that this wasn’t the first time she had done something like this.

I continued to somehow keep the car on the road as we kept motoring towards my house. Actually, now that I thought of it, I didn’t really know where I was going. Was Alison under the assumption she was coming home with me in some pre-arrangement she had worked out with Anna? Or was I to take her to a hotel that she likely had waiting for her, set-up by whatever producer had flown her out to Vancouver in the first place.

“Fuck that feels good,” I murmurred.

I continued to drive on the road taking us to my place while Alison slowly yet steadily bounced on my lap. Her snatch was tight, something that made her velvety folds clutch and rub my veiny shaft as it was worked in and out. She was also wetter then any cunt I had been in before, clearly the plane ride and wanting to hook up with me based on Anna’s recommendation had her turned on tremendously.

“I’m getting close stud,” she told me.

I still was wishing to suck on her tits but I knew that was a pipe dream so I was content to use my peripheral vision to see her pillowy breasts jiggle every time she rose up on my shaft. It wasn’t idle but I was able to stare at Alison Brie’s bouncy tits in the flesh so how could I possibly complain, and better yet, who would listen?

“Good…me too,” I huffed.

Normally I pride myself on my ability to last for a good amount of time in the sack, however tonight was shorter than my average by some margin. Ali had only been riding me for maybe 5 minutes, but before that she blew me for close to quarter of an hour. Plus there was the fact that fucking so publicly and in a kinky situation really had my mojo rocking, so much so that I need to cum sooner rather than later, but first was to make sure the brunette actress went first.

“So close…use your finger.”

Now, Ali and I had never hooked up before so I didn’t exactly know what she meant by that. Most girls, especially when you first hook up mean for you to diddle their clit, flick their bean so that they can cum. However, I was feeling a little ricque tonight, probably from the sleep deprivation, extra coffee and crazy fucking so I took a chance.

We were both nearing our orgasm and Alison’s riding on my lap had slowed to a crawl, content to impale herself on my fully to have me as deep as possible then rocking back and forth. It allowed me to raise my knee so the flat of my thigh contacted the bottom of the steering wheel, allowing it to have control and free up both hands. I used my right hand to somehow squeeze between our pressed bodies then extended my finger to reach her exposed clit, at which point I repeatedly flicked her bean.

“Oh fuck! Just like that,” she groaned.

I didn’t stop there though. With the minimally required steering being performed by my leg, I took my left hand off the wheel and placed it on her butt, which was shaped like a firm but well rounded bubble. I squeezed and allowed my fingers to migrate into the crack of her ass cheeks then proceeded to press my middle fingertip firmly against her wrinkled rosebud and rub around the hole’s surface.

“You gonna cum with my dick deep in your pussy and a finger in your ass,” I asked the grinding woman.

“Get that in my ass now,” she said feverishly.

I didn’t hesitate and promptly pushed past her hole’s resistance until my middle digit was wedged right into her keister. No sooner had I worked my lengthy finger into her butt was when I felt the brunette start to quake from on top of me, causing her pillowy tits to jiggle more than usual. As if to confirm the fact she was having a strong orgasm, she screamed aloud, right into my ear while her pussy clamped down on my like a vice grip.

“Fuck,” she swore, clearly exhausted though resumed riding my length.

“I’m about to cum,” I warned, my words going right into her ear which was right next to my lips.

This being our first time having sex, we didn’t have that natural rhythm or chemistry that happened the more often you fucked. Thus, I was understandably upset when I felt her hands pushed off my shoulder in a move that caused her warm, moist pussy to pull off of my dick. Then again, how upset could I be when an impossibly pretty girl just gave me a great blowjob and a good ride.

“Cum in my mouth,” Alison told me.

No further talking was needed as I noticed her ass was back in her own seat and she was facing me. She bent over at the waist and her head was back in my lap where we started in the first place. Rather then descending most of the way down my member, which was slathered in her pussy juice, this time the brunette star had pulled me back enough so that only the head of my cock was between her lips and kept applying suction and making tiny bobs down.

“Fuck…here it comes,” I warned her for a second and final time.

Alison barely had time to comprehend the words before the first spurt of jizz came shooting out of the end of my dick. I could see out of my peripheral vision as she paused a bit as the hot semen plastered the roof of her mouth but noticed her regain her composure quickly to swallow down the initial burst within an audible gulp and returned to sucking my member.

I couldn’t believe her oral skill as she bobbed on my tool while hungrily sucking down all of my sticky seed that I had pumped into her mouth. Eventually my balls emptied completely but Alison continued to slurp up any last remaining trace of jizz that she could find before finally letting the cock slip from her talented mouth.

“Mmhmm Mmhmm mmmm,” the actress moaned. “Can’t decide what tastes better…your sticky cum or my own flavor.”

“Fucking hell,” I swore, getting a grip back on the situation. After a pause of close to a minute I finally remembered what I needed to ask the petite woman. “Where are we going?”

“Oh, I guess Anna didn’t tell you,” Alison said.

“Tell me what?”

“Once she knew I had business here in Vancouver she asked me to fly in a night early and surprise you for her so I didn’t actually set up a hotel stay. I figured we screw at your place all night but then I couldn’t help myself once we were alone,” the actress confessed.

“Damn…that woman is amazing,” I stated out loud.

“You should see how well she munches rug,” Alison shared.

“I would very much like to see that actually,” I said, smiling over at her then lingered my gaze on her tits, which were still out of her dress. “Well the good news is that we’ll be back to my place in another few minutes.”

“Awesome. Could really use a shower,” she replied before finally putting her tits away and doing up her belt again.

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Re: Dating Anna Kendrick
« Reply #2 on: November 27, 2019, 11:47:05 AM »
Title: Dating Anna Kendrick Part 3 - Visiting Los Angeles
Celebs: Anna Kendrick, Kristen Stewart
Codes:  MFF, FF, anal, oral
Disclaimer: I do not know Kristen Stewart or Anna Kendrick. This story is an act of pure fiction, therefore didn’t happen. I make no money from this story.

Summary:  Continuation of Anna Kendrick Super Bowl Bet and Alison Brie’s repayment. Og is in LA and calls up Anna who’s happy to have him but also has a girlfriend in town, Kristen Stewart.

“We have now landed in Los Angeles, thank you for choosing…”

I didn’t normally sleep on flights and this one was no exception. It wasn’t a long journey as Vancouver and LA weren’t too far apart. I was able to get caught up on a few TV shows that I was meaning to so that my friends would stop potentially spoiling future events.

As soon as I was back on solid ground I powered back up my cell. I had a few messages but those would wait for now as I only had thoughts for one particular person. I scrolled through my contacts until my thumb fell onto her name, Anna Kendrick.

Anna and I had been friends with benefits since the Super Bowl last year. We had met while I was working on set at one of her movies years before and we had always stayed in contact. When she text me and said she was alone in Vancouver filming while her team was in the biggest football game of the season I invited her to the party I was throwing.

That went well by the fact that we had sex that night several times and continued our tryst throughout her time in Canada. When she left we stayed in contact every now and then but now I was being sent to complete a certification that was being held in California, specifically in the city Anna lived.

“Anna…it’s me Og,” I said after hearing her pick up her phone.

“Hey stud! Your plane arrive alright,” she asked in her pleasant voice.

“Yeah for sure. Did you want to grab a drink somewhere? Your town, your choice on pub,” I said while hearing chatter on the other end between Anna and someone else.

“Actually I have another friend here so why not just come straight here,” Anna suggested. She paused for a few seconds, listening to her friend before addressing me once more. “Just come right in, don’t bother knocking.”

“Okay…” I replied. “Text me your address in the next few minutes. I’m just waiting on my bag then I’ll grab a cab.”

“See you soon tiger,” she added before hanging up.

Luckily my plane got in at a perfect time so that it was late enough to avoid rush hour traffic and yet too early for the night-time traffic to clog the streets. Anna’s condo wasn’t too far from the airport as the cab was dropping me off on the curb in front of her condo 30 minutes after our phone call ended.

I took the lift and arrived at her door, raising my hand with a balled fist to rasp on the wood before remembering her earlier instructions left for me. Lowering my arm I instead opened my hand, clutched the knob and spun it. I didn’t meet any resistance as the door swung inside to reveal a scene that very much shocked me.

Directly in front of my line of sight, no more then 20 feet inside her condo was Anna lying flat out naked on her sofa. That alone would have been a happy finding but the surprising part was that between her widespread legs was a slender woman with red hair who was eating her out with vigor…and Anna was loving every minute of it.

“Holy mother of God,” I gasped under my breath.

Though I had said it fairly quietly my words were enough to catch the attention of the woman I presumed was the friend Anna mentioned that was visiting this weekend. It caused the redhead girl to sit back on her heels and show off that she was not only naked but a very familiar face. Her beautiful green eyes flashed towards me as she seductively used the back of her hand to wipe away the pussy juices from my sometimes-girlfriend.

“Oh hey Og. Do you know Kristen,” Anna greeted from her back. “And please close the door behind you sweetie.”

The Kristen she referred to was that of Twilight fame, which is when it clicked to me that they had shared the screen in that awful film series based on the even-worse books. Without the media knowing it, the pair remained close friends for nearly a decade since the first movie and knew that I thought about it, I could understand why…Kristen’s tongue buried in her pussy aside.

Though Anna hid it better from pop culture, she was just as big a stoner as Kristen though the Pitch Perfect star hid it better, not to mention didn’t come off as bitchy during interviews. They both had also hooked up with directors with the small distinction being that when Anna did it he was single meanwhile Kristen had public outrage as a man in position above her seduced her while married…yet she was the bad person in the eyes of everyone.

Snapping back to reality I had become aware that I had not replied to Anna. Trying to stop looking like an idiot, I picked up my jaw from the floor, wiped the drool from the corner of my lips and tried to use my words like a normal human being.

“Never met her formally,” was what I came up with. “But I know of her of course.”

“Nice to meet you,” the redhead said, still sitting naked back on her heels.

“So…you guys…do this often,” I asked, trying to hide the excitement while also focusing on stringing two words together.

“A few times, last was with my ex-boyfriend. The one that shimmered,” Kristen joked.

“You had sex with a teen heartthrob,” this time failing to withhold a chuckle.

“Sucked him, fucked him, hell was even sodomized by him. A good lay,” Anna summarized before quickly adding. “He had nothing on you though Og.”

“Appreciate you trying to spare my pride but I’m not that insecure,” I replied, seeing a wave of relief crest her gorgeous face.

“I seem to remember that you also let him pis…”

“…ton his cock between my great tits,” Anna cut her off, though I was extremely interested in having a follow-up conversation with Kristen about the actual ending to that sentence.

Looking at both women, naked in all their glory I couldn’t help but compare and contrast their stunning features. Though they were similar in that they had beautiful but slightly atypical faces and bare pussies (except for Kristen donning a thin strip) they had their differences as well.

When it came to their tits, ass and legs, the pair were opposites. They both had great bodies but Anna’s best asset were her sagless C-cup breasts, made to look bigger given her tiny frame. This was followed by her small but plump ass that was oh so biteable, and finally her legs which were slender and smooth but nothing special.

The inverse was true for Kristen Stewart though. The Twilight star had boobs that fit her slim body well, my guess being a healthy B cup, with small pink nipples but they pailed in comparison to Anna’s, as well as her own other features. She had a great rounded ass that was severely underrated until displayed properly in tight-fitting dresses but her star attribute was her gorgeous legs that were long, lean yet had toned muscles that made them look feminine but sexy.

“Now I was kinda in the middle of something so if you don’t mind getting rid of the clothes and maybe making us some drinks I’d appreciate that,” the suddenly stone-faced Kristen said to me.

I shut up immediately and watched on as a backtracked into the kitchen. A quick glance showed me a bottle of tequila on the counter with two used shot glasses nearby. I opened a few cupboards with haste and found an orange juice glass which would do for me just fine.

Only seconds had elapsed since I left for the kitchen and I had hardly missed a thing. Kristen was just finishing her liplock with her friend as her hands clutched Anna’s wrists, pinning them up over her head. It made her breasts heave upwards, a fact Kristen didn’t miss as she leaned down and took turns taking each of her nipples into her mouth.

“Shit,” Anna cooed as the other woman’s tongue swirled around her tits.

Kristen switched sides a few time before continuing her descent down Anna’s slender body, finally arriving at her destination. Her snatch was shaved smooth without even a hint of hair which made the brightness of her pink pussy look even more radiant. The red-haired star must have thought the same thing as she instantly reacquainted her tongue with Anna’s twat.

As I undid my belt buckle and pulled it free from my waistline, the Twilight actress buried her tongue in Anna’s snatch repeatedly. My pants came down to reveal my erection contained in my briefs as Kristen used her nose to stimulate her friend’s clit expertly. I pulled my polo up over my head and my eyes re-adjusted on the action in front of me, this time with the redhead using her flat tongue to lick up and down her slit.

“You are so God damn tasty,” Kristen commented. “And I think your boyfriend is ready for you slut.”

She was referring to the fact that I had stripped off the last remaining article of clothing and had my cock, standing a proud 8 and a half inches, out on full display. Anna rolled her head to the side and her eyes went wide at the sight of the dick that was now only mere feet from her face.

“There’s my favorite penis,” she said. “Uhh God Kristen that’s good.”

Anna continued to say that she was excited to see it and had been thinking about my dick but that was all drown out the second she reached out and grabbed hold of my member. She gave me a few strokes as she licked her lips, all while Kristen kept licking her. She moaned as I guessed her friend hit another sweet spot in her, all while she tilted my cock skyward to run her tongue up my underside.

The second her tongue touched me I was lost in a blissful moment. Ever since the first time we hooked up I became obsessed with her oral skills and craved them. Every woman since Anna was average or good at blowjobs but Anna was the best. I was reminded of that as soon as she opened her mouth wide and took the head of my cock into her mouth.

“That’s what I’ve been craving.”

I closed my eyes shut and savored the feeling of her talented tongue swirling small concentric circles around my crown. From her position flat on her back with legs spread eagle she wasn’t at her best, but she compensated for that with more effort. Twisting her upper body towards me she wrapped her arms around me, clutched my naked ass and used that to guide more meat into her mouth.

“That is a gorgeous cock,” Kristen said, appearing on top of Anna’s supine body.

I’d completely forgotten about the redhead though that may seem ridiculous since I knew that she was eating out my quasi-girlfriend. However, this was my first threesome and I’d lost track of her the second Anna’s hand then mouth touched my member.

“Want some of this,” Anna said to her friend lying on top of her.

I looked down and noticed that Kristen’s eyes never strayed from my cock whatsoever as the question was posed to her. They began moving together, making me wonder if they had done many threesomes in the past other then at least once with Kristen’s ex. Anna pulled her mouth off my cock and moved south to lick my balls as the redhead leaned in and engulfed my cock, freshly coated in her friend’s spit.

This time I kept my eyes open with determination to not miss a moment of this amazing encounter. It allowed me to spy Anna multitasking, using her tongue and mouth to take turns on each of my nuts while sliding a hand down Kristen’s back. If the Twilight noticed then she didn’t care as the only thing on her mind was sucking my cock and trying to milk me as soon as possible.

Anna caressed her friend’s surprisingly plump naked ass while they still worked in tandem to blow me. Her arms were short so it meant that she could only get a finger between the other girl’s cheeks and I watched as it began to make circles.

“Anna! I didn’t know we were going for anal fun tonight too,” Kristen practically celebrated.

“It’s a special occasion,” the other replied as I kept watching Anna rub Kristen’s asshole.

“You really do like this guy,” the redhead countered, sticking out and licking my pee slit to emphasize who the guy in question was. “But you know what I would much prefer.”

“I’d love to toss that salad,” I jumped in, licking my lips.

“No way. Her tasty booty is mine,” Anna retorted. “Plus this way Kristen can have some more of that cock she’s drooling over.”

I was disappointed when Anna’s mouth left my sack for good as she squirmed herself out from the bottom of the sandwich we had made. Kristen reacted by using her hands and knees to support herself now with the new position able to have her thick ass pointed up for the Pitch Perfect singer to have better access.

“Man this thing is a beauty,” Kristen commented.

The redhead didn’t wait for her friend to start servicing her before she gave me attention. Opening her mouth wide she took me between her lips before creating a seal halfway down my shaft. I could feel my tip poke her in the back of the throat but she checked her gag reflex and didn’t even cough.

She repeated the trick several times, me reaching down and holding her shiny hair out from her face while I watched. Her head moved up and down with good speed and I saw her cheeks hollow as she applied enough suction that I thought she’d succeed in literally sucking the cum straight up from my nuts.

“Fuck you’re good,” I groaned, my fist tightening in her hair.

She really was good, not as good as Anna but in the next tier beneath that God level. It also didn’t hurt that her tongue that was gliding along the underside of my tool was moaning and vibrating as my kinda-girlfriend chose that moment to start eating out her asshole. I looked down Kristen’s pale body to see her with her adorable face buried in her best friend’s thick cheeks.

“Uhhh…I love that tongue in my ass,” Kristen cooed.

I wish I could have watched as Anna’s skilled tongue danced about her puckered opening, probing every crinkle around the center. I felt a bigger grunt from Kristen, some noise escaping from her mouth filled with my cock and imagined that was when Anna made her tongue pointed and pushed inside her anus. Anna’s small hands were gripping her friend’s ass cheeks, pulling them apart to help create a gap within her tightest of holes.

“Your bum is soooo yummy,” Anna told her best friend before adding. “And I’m not just saying that to kiss your ass.”

Anna followed up that statement by literally planting a kiss on each ass cheek before placing her lips directly against the other girl’s backdoor. Kristen deserved heaps of credit because while she was receiving Anna’s best rimjob, she didn’t falter in swallowing my cock or at least the first 5 inches of it.

“Mhmm…so good,” Kristen purred before biting her lower lip.

As if being on the business end of a great blowjob wasn’t enough, I also got to watch the Pitch Perfect star continue to toss Kristen’s salad. Then there was all the gurgling noises coming from the redhead as she continuously took me as deep into her mouth as possible. The throaty sounds and extra spit she coughed up on my rod only added to the great experience.

“Hearing you suck my boyfriend’s cock is making my pussy so wet,” Anna moaned from behind her friend.

“Then how about I take care of that for you,” I proposed with a predatory smile.

“Yes please,” Anna said.

The auburn-haired actress gave Kristen’s asshole one last good lick before slapping her bottom playfully while getting to her feet. The redhead released her lip lock on my cock and allowed me to walk over to Anna, who I immediately embraced in a passionate kiss for the first time that night.

We broke the kiss when I felt her hand close around my very wet cock, courtesy of Anna’s best friend. Her hand slide along my pole with far greater ease then before, helping to keep me hard, not that the circumstances alone wouldn’t have worked. Opening my eyes, I became aware that Kristen had also stood and was now directly beside the fellow actress.

“I can’t wait to watch him fuck you,” Kristen told her, following up her slutty words with a tongue-filled kiss.

“Bedroom,” I blurted out.

“This way,” they replied in unison.

Anna clutched Kristen’s hand as they started off towards Anna’s bedroom. It was only a one room condo so I had a 50-50 chance of picking it but I figured that they could lead. I followed shift on their heels as the auburn-haired singer turned right and opened the door. Her bedroom was nothing special, a large king bed in the middle of the floor but it would fit the bill perfectly.

While I watched Anna crawl onto her plush bed Kristen grabbed the back of my head and pulled me down for a kiss. I realized just how small she was given how low I had to stoop to press my lips against hers, but I banished that thought when our tongues started mingling.

When he separated less than a minute later I found the auburn-haired actress on her back with her knees bent so her calves dangled over the edge. I couldn’t wait any longer but before just slamming into her I squatted down and ran my tongue through her folds and confirmed she was gushing just like she had said earlier.

“God yes,” she moaned as he entered her.

This time I grabbed my cock around the base, climbed on top of the much smaller girl and buried myself inside her in one push. Kristen had done a great job prepping her which allowed me to ramp up to pounding into her tasty snatch with raw power. Anna was powerless to do much other than arching her neck and back while her loud screaming echoed around what I hoped were soundproofed walls.

I didn’t want Kristen to think I forgot about her but she had read my mind. As I looked over at her she jerked my head towards her and our lips met with yet another explosion of passion, which coincided with her pussy getting wetter once again.

I had risen up higher onto my knees to draw level height with the slutty redhead, however it didn’t mean that I neglected my duty with Anna. The slight variation on missionary position still allowed me to penetrate her just as deeply, albeit at a loss of some speed.

“Shhhhhit,” Kristen groaned as two of my fingers entered her snatch.

The fiery redhead began moaning repeatedly into my mouth while Anna’s screams were still ringing out around the room. It seemed like the more passionate I kissed Kristen I would respond by spiking my dick as far as possible into Anna’s mound.

“Oh…mhmmm…feels so…amazing,” Anna cried out as I continued to plow into her from behind.

“Let me taste her from your cock,” Kristen begged, already in position.

Anna ran a hand through her long shining hair and nodded her head to me as if giving me the go ahead to pull out. I wasn’t really looking for permission but I stepped back from her and turned to the side where Kristen pounced on my cock with her mouth once more. I looked down and saw her savoring the juices coating my member, clearly loving every drop of Anna that remained on my cock.

“My turn,” Kristen said after bobbing on my length a few more times.

“Wanna fuck you now,” I huffed in confirmation.

Kristen gave her best friend a look and it seemed like Anna knew exactly what she wanted from her as she pushed up the bed until her head rested in the pillows. Kristen was up next on the mattress as she crawled so her head was in between Anna’s spread legs, a position she seemed to love to be in.

Though my vision of them was being blocked for the moment, I could tell when Kristen started licking my girlfriend when her beautiful face contorted into that of pure pleasure. Standing up tall I was now able to look over the redhead’ body and watch a her mouth sealed around Anna’s pussy and ate her out expertly.

“Yes…mhmmm….ohhh,” Anna moaned. “Such a good carpet muncher.”

I enjoyed the show but looking down Kristen’s skinny but curvy-in-all-the-right places body made me need to snap into action. Not wanting her to feel left out I leaned down to lick her twat to be sure she was prepared for me. After a few swipes of my tongue I realized that the Twilight star was a fountain between the leg and ready for me.

At the risk of sounding cocky, I was concerned with giving into my animalistic side right away and pound her as hard as I did with Anna right away mainly due to the hugeness of my manhood. She was also tiny so I decided it would be best for to start at a lower pace, at least to start with.

It was tough to rein myself back but I accomplished the goal until after a minute I was stroking my entire length into the slender actress. However the second my hips met her surprisingly curvy ass, she flash me a look that portrayed she a ready to go.

While yet to ramp up my speed, I was able to watch the redhead I was fucking eat out my girlfriend. After enjoying the Anna’s impressive oral sex from earlier in the evening, Kristen didn’t hesitate to repay the favor, not that she ever need a reason to eat out her gorgeous best friend. I could watch as she ran her tongue through the Pitch Perfect star’s folds, which made Anna shudder and moan in appreciation.

Kristen used her fingers and pulled apart the other girl’s labia. I could tell that she got such a thrill seeing how pink her hole was especially in contrast to her hairless white skin around the opening simply because it evoked the same sentiment in myself. After taking another moment or two to marvel at the beauty, Kristen dipped her tongue into Anna.

“Mmmppphhh,” Anna mumbled deep into the pillow she pressed against her face.

“I think she said ‘thank you,’” I translated to Kristen.

I also used that moment to crank my rythym up to full speed as to actually start fucking the movie star hard. She moaned sharply, surprised by my new tactic, but settled into it as illustrated by the fact she was rocking her petite body back against my pistoning hips. Her meaty cheeks rippled under our combined force as we both seemed pleased with the faster pace.

I had the urge to reach down and pull the slutty girl’s hair but I noticed how much she had Anna squirming. Since we had been hooking up for over 6 months I knew when my girlfriend was getting close to coming so I didn’t want to slow her pending orgasm. However that didn’t stop me from giving Kristen’s curvy hips a death lock as I slammed her backwards to skewer her gushing cunt on my rod.

“Fuck you’re a good lay,” Kristen complimented, pussy juice slathered around her lips.

As I felt the compliment wash over me and perk up more energy to maintain my current pace, I saw Kristen putting the finishing touches on her friend’s pending orgasm. She moved her mouth back up to Anna’s clit and lashed it with her tongue all while her two slim fingers blasted deep and repeatedly into her snatch,

“Yesssss…..MMMHHHMMMMMM,” Anna screamed into her pillow once again as she climaxed.

Kristen had just made her best friend cum and now she was after another orgasm, this time her own. She removed her fingers from Anna’s twat and brought it between her legs and used the vast amount of cum on them to smear around her clit. The stimulation of her sensitive nub combined with my thick cock pounding her relentlessly was enough to have her orgasm as well.

“Good job babe…Kristen doesn’t cum easy,” Anna congratulated me.

“Ever had that big cock sucked by two girls at the same time,” Kristen asked me, looking back over her shoulder after they had both recovered somewhat after cumming.

“No. Never,” I answered honestly.

“Then it’s your lucky day, big boy,” Anna cut in.

In the blink of an eye both beautiful women had sprung off the bed and onto their knee in front of me. This time, Kristen didn’t let Anna have the first go around with me like she had been doing the rest of the night. Opening her mouth, she picked up where she left off earlier and allowed half my dick in one go.

Much to my pleasure her bobbing on my length was as intense as ever. Though she didn’t take me all the way don like Anna could, she made up for it with pure energy. Her effort burned bright for a minute before she pulled away from me and angled my cock toward the auburn-haired singer.

“Yeah…suck his big dick Anna,” Kristen encouraged.

Anna didn’t need the instruction but it appeared that both of us got excited by the dirty talk from the stoner. The Pitch Perfect star rose to the occasion in being in essentially a head-to-head competition with her best friend by loosening her throat and taking me all the way inside, which I responded by releasing a torrent of grunts.

Yet it didn’t take the Twilight star long to show off her dominance. Shortly after turning me over to Anna, the redhead sent a trail of kisses up along the deep-throating girl’s neck until following along her cheek. By the time she made it to the edge of of her mouth, Anna was returning the kiss.

“Oh my God,” I groaned at both the sensation and show on display.

With her lips still partially around my bulbous head, Anna and Kristen were making out. The two girls each had part of their lips on each other’s mouths but also were both on my penis, making me a very happy person for obvious reasons. Their tongues were wagging wildly as they alternated from wrapping around each other and also dancing along the sensitive tip.

Kristen was more aggressive then her best friend so it didn’t take her long to edge the singer away from the prize. The red-haired stoner was now assertively in control of my long dick and taking a healthy portion of it into her mouth. Not wanting to be left out in the cold, Anna wrapped her lips around the last few inches of me not occupied in the other girl’s mouth.

Kristen wasn’t wasting her chance in the driver’s seat as she energetically sucked on my long cock. She kept alternating between super-fast, shallow strokes using her lips but then would take me deeper into her mouth so that her lips would butt up against Anna’s.

“You like having your fat dick pounding the back of my slutty little mouth,” Kristen seductively asked as she allowed Anna another turn blowing me.

“I think he prefers actually going all the way down my throat more,” Anna cut in, fresh from doing what she had just described.

“It’s normal to have a gag reflex,” the naked redhead spat in response.

“How cute. I remember when I had one of those…in grade 8,” Anna laughed.

“Okay as much as I love the friendly banter I really want to fuck on of you again,” I urged.

“Since my whore of a best friend got you all lubed up well with her spit, how about you fuck my tight little ass,” Kristen offered.

Before I had even agreed the redhead was getting into position on the large bed. I joined Kristen on the mattress with the two of us laying on our sides with her much smaller frame against my powerful chest. My dick was glistening in the dim lighting due to Anna’s spit covering it but to make sure she was prepped the redhead transferred a lot of her own saliva to her fingers before reaching back and smearing it around the outer ring of her anus.

“Come on…it’s not going to fuck itself,” she said with a cocky grin.

I didn’t waste a second of time as I gripped my base, placed the tip against her crinkled entrance and pushed until the first third of my thick cock was planted in her ass.

“Oh God you’re huge,” Kristen groaned as I slowly worked myself in and out.

“Yeah you won’t be sitting comfortably for a few days,” Anna said from the corner of the bed.

I continued to slowly work into Kristen’s rump mainly because I knew that going too fast too soon was asking for trouble. However when I felt the redhead push her ass back towards me so that she was taking half my dick in her booty I figured she was ready for more.

Anna must have been reading our minds or our body language because she was on the same page as well. Leaning herself downward so used her skilled mouth one her best friend, wiggling her tongue up and down her pink slit no more than a few inches away from where my cock was spearing into her bowels.

“Fuckkk…you two know how to treat a lady,” Kristen moaned.

I also let out a groan as I felt my dick bury further in her tight anal walls and once I had a taste (so to speak) of her asshole there was no way my urge could be satisfied. Blocking all other thought from my mind, I relentlessly pounded into the Twilight star’s backdoor. To Anna’s credit, she had selected a high caliber slut for a best friend as Kristen seemed to take the plowing and kept encouraging me to go harder and faster.

“So tight,” I announced while continuing to work more cock into her hole.

“It feels so good,” Kristen cooed, still enjoying mine and Anna’s dual efforts.

“Slut,” the Pitch Perfect actress said to her friend, having taken a brief break from eating her twat.

“I may be a slut but I’m the slut that your boyfriend is fucking right in front of you,” the redhead bantered with Anna.

I was curious what Anna was going to do about that comment but she simply laughed about it. These two clearly had a unique relationship, not that I cared since it allowed me to be balls deep in her best friend’s asshole while she ate her out like a submissive whore.

“I’ll make you pay for that later,” Anna replied to her quip.

“Yes my clit! Lick my clit,” Kristen instructed Anna before turning her head to address me. “And you keep that dick deep in my ass.”

The two of us listened to the bossy star’s orders and carried them out to the tee. I was pleased that the girl was close to cumming, which seemed to re-vitalize my fleeting energy to some degree. As I kept plowing the deeper reaches of her bowels, Anna copied her best friend’s earlier oral work by clamping lips around Kristen’s clit and combining motions of sucking and licking.

Kristen’s fine ass was rippling with the force of my every thrust each time my cock disappeared past her muscular ring. It was such a surreal sight seeing the speed at which I made my cock impale her asshole given how tiny the actress truly was, not to mention that she was loving every minute of the sodomy.

“Make me cum in your girlfriend’s mouth. So close,” Kristen spewed at me. “Go back to my pussy now.”

Anna listened to red-haired girl and quickly moved her lips off of her clit and back down to her hole. By the time she reached her tongue back inside, I felt Kristen start to jerk before she unleashed the loudest scream of the night.

The Twilight actress gasped loudly then seemed to begin chanting some unintelligible babble as she came. Her juices flowed down right into Anna’s mouth, where my auburn-haired beauty seemed to greedily drink down each drop of the other girl’s cum.

“My turn,” Anna exclaimed after finished licking all the cum from Kristen.

I wasn’t going to turn that offer down but I had barely pulled out of Kristen’s ass when Anna had stepped over her exhausted body and rolled me onto my back. I had no problem with her energetic attitude as she swung her slender legs on either side of my muscular body and sat on my lap.

I pulled her head down and kissed her passionately for the first time in what seemed like a long time. As our lips stayed locked together I felt her dainty fingers close around my ass-soaked member as she lined me up with her hole and sank down. To my surprise and delight, it was the second asshole of the night that I had penetrated.

“Always forget how great your cock feels in my ass,” Anna cooed as we got started.

“Ditto,” I grunted as her tighter backdoor squeezed my dick with all its strength.

We didn’t have the added benefit of my dick being wet from a sloppy blowjob like when I first ass-fucked Kristen so Anna and I had to go a little slower. We’d had anal sex before so it wasn’t like she couldn’t handle my thickness in her tiny little ass, but the lack of lube meant I wasn’t thrusting my hips upwards to fast until she loosened up more.

Luckily Anna was relaxing more by each passing short thrust into her booty. Little by little her dirt road opened further, allowing me to get over half my length up into her ass without difficulty. I placed both of my strong hands on her small cheeks and pulled them apart with as much strength as I had, which did the trick.

“Holy God. It’s all in there,” Anna exclaimed as I was buried to the hilt in her backdoor.

“You like my cock in your ass? Want me to fuck you harder,” I asked.

“Yes baby…fuck my ass,” Anna replied.

I took her up on her request and withdrew until only my head remained in her anal canal. This time I thrust into her in one sudden swoop so that I could feel my hips pressed against her plump cheeks. Anna let out a quick gasp but by the time I repeated the action two more times she was now emitting long, low moans.

It had been a long night sexually and I could feel my own orgasm approaching but for now I was doing my utmost to simultaneously hold off my release as long as possible while making Anna cum for a third time tonight. I was gritting my teeth due to how good it was feeling to stroking my entire length into Anna’s tight backdoor. We had built up to a steady penetration rhythm as the slim girl’s asshole repeatedly was impaled by the biggest cock that she’d ever had inside her.

To help distract myself a ran a hand up from her plump ass cheek over her taut stomach to knead one of her bouncing tits. They felt heavy in my hand as my fingers dug into soft flesh before a focus my attention on rolling her nipple between my thumb and fore finger. It served to make Anna moan louder, as well as grind her hips back and forth on my cock next time she sank right down onto my lap.

“Jesus…won’t last much longer,” I admitted.

“Little more…so close,” my favorite sex puppet replied.

My endurance was almost ebbed completely away but I was the determined sort and was going to make it happen. Remembering again what would get her there, my free hand rolled from her hip to between her legs and instantly found her clit. I rubbed her snatch so quickly that I feared it was painful, but Anna only felt pleasure.

“Cream inside her,” Kristen’s voice dictated.

The stars must have aligned because my stubborn endurance was on the verge of maxing out as well. And luckily for Anna, as I edged closer to release my nipple play got harder too and that turned out to be exactly what she needed in tandem with my nearly frictioning off her clit.

“Yes baby…fuck my ass…fuck my ass…fuck my ass,” she screamed in steady encouragement.

To keep up with her demands, which detailed pistoning my cock in and out of her asshole at ridiculous speeds, had finally reached its breaking point. I did a thrust into her one last time then stayed buried inside her vice-like sphincter closed tightly around the base of my cock just as Kristen instructed.

“Awwh….shittttt,” I grunted while cumming deep into her bowels.

As the first streak of cum plastered itself on her rectal walls, Anna came again. With my grip on her small but very hard nipple nearly doubling as I came, the auburn-haired girl was pushed past her point.

“Shhiiittt….I’m CUMMMINNNNGG,” Anna screamed.

I could tell Kristen waited until we had both cum before she sprang back to life, albeit much slower then before. The redhead pulled my cock smoothly from her best friend’s booty and placed it right into her mouth as she bobbed a few times with deliberate motion before taking it out and licking up both sides from base to tip.

“Your dick tastes so good though,” Kristen commented.

“Actually I think that’s my asshole you’re enjoying so much,” Anna chimed in, her exhausted body pressed against me.

Kristen shrugged her shoulders to concede the point to her friend before descending her head back onto my sensitive tip. I shuddered from her wet attack but it didn’t last long as she moved from me onto Anna.

With my cock free from her asshole Kristen twisted her neck so that her lips were pressed around the outside of the Oscar nominee’s rectum and waited patiently with her mouth held open directly underneath the gaping hole. It only took a handful of seconds before Kristen moved out from under the other girl’s ass with the prize she sought.

However, rather than swallow the mouthful of cum she had collected from the deep recesses of Anna’s ass, Kristen held it in her mouth and went in to kiss her gorgeous friend. Anna dipped her head towards the redhead to kiss her back, all this while still laying on top of me.

The Pitch Perfect was surprised, but in a good way, when my cum was spat into her mouth. With a flash of her large eyes to Kristen, I watched as Anna swallowed down the salty load in one big gulp.

“Yum,” my girlfriend purred.

I’m not too sure what happened the rest of the night. I remember getting to my feet at some point and stumbling into the washroom to piss before returning to the bedroom. I barely remembered to set my phone’s alarm for my early wake up call tomorrow before passing out sandwiched between the two gorgeous women.

« Last Edit: November 27, 2019, 02:09:35 PM by thechemist »
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Re: Dating Anna Kendrick
« Reply #3 on: November 27, 2019, 02:10:41 PM »
Title: Dating Anna Kendrick Part 4 - A Little Help From My Friends
Author: The Chemist
Celebs: Cara Delevingne
Codes:  MF, anal, oral, POV, rim
Disclaimer:  This is an act of fiction. I do not know Cara Delevingne, Anna Kendrick or Anna Kendrick at all and this scenario did not actually occur. I make no money from this story.

Summary:  In order to get her lesbian lover Cara Delevingne on board with anal sex, Kristen Stewart brings her to a man she knows is exceptional at it.

I yawned as I rose from bed before stretching my arms high and back. I had another good sleep, albeit lonely with Anna Kendrick, my girlfriend, out of town filming yet another movie. We were getting more and more serious, with me even going to visit with her on her various movie sets, however I had work on my own set this weekend.

Unlike Anna, I work behind the scenes. I like the work, it keeps me connected and in frequent contact with beautiful women and in the field that I love. I’m not an actor as I’ve never been comfortable in front of an audience, but as an assistant learning the trade of a filmographer I completely thrive.


“Who’s texting me at this unGodly hour of…9am,” I said aloud to no one.

Company coming in 15. Be awake and showered. Trust me and play along.

I had thought when I heard my cell buzz that it would be the adorable actress I was dating, instead it was her bitchy but hot friend Kristen Stewart. I hadn’t seen the fiery redhead in months, not since she, Anna and I shared my bed for a steamy threesome. But why she would be coming over to my place when she knew Anna wasn’t here made little to no sense.

“Shower time,” I said, raising from the bed.

Even as I had a quick cleaning I still couldn’t figure out why Kristen was coming over. And why I had to play along with some scheme of hers. She must have company with her was the only thing I could reason.

I had time to shower, get dressed and make a quick breakfast burrito. It was Saturday so I normally would have slept in a bit later after working long hours all week before doing typical weekend chores like tidying the house, grocery shopping and the like. Hell, I wouldn’t even have time to watch Sports Center!


It was good enough timing as I had just finished boiling water and grinding my coffee beans, combining them in my French Press to brew for 10 minutes. I didn’t look through the peep hole knowing who it was already, but instead of just Kristen Stewart, there was a second recognizable girl with her.

“Sup Og. Anna around,” Kristen asked, already showing herself in.

“Hey to you too,” I said to the somewhat pushy redhead before turning to address her friend. “Hi, I’m Og.”

“Cara,” the leggy blonde replied, shaking my hand.

I had just seen Suicide Squad plus hadn’t been living under a rock so I had instantly recognized the model-turned-actress as Cara Delevingne. Just like on screen, the girl had a gorgeous face, fit body and the longest, most perfect legs I’d ever seen on a girl in the flesh. And despite being a model she had curves complete with a more-than-decent rack and a surprisingly bubbly ass.

“Oh right, Cara that’s Anna’s boytoy. Og, this is my girlfriend,” Kristen said, getting around to introducing us.

“And Anna is away…”

“Shit she got called in to set,” Kristen said, interrupting me and adding in a lie.

“Yup. Total last minute thing. I guess she didn’t warn you,” I added, remembering her text message.

“Such a forgetful slut,” the redhead replied. “Shit…I’m getting buzzed. Gonna use your room.”

Kristen was pulling out her cellphone as she disappeared into my bedroom and closed the door behind her. Cara and I shared an awkward look of two people who were just meeting for the first time and suddenly left alone without having a single thing to say. Realizing I should break ice, I cleared my throat.

“Loved you in Suicide Squad,” I said, that being the first thing that came into my mind. “And Paper Towns.”

“Thank you,” she said, her English accent bleeding through. “I was nervous and the CGI was crap…but that’s just between us.”

We talked a little more and I found her in stark contrast to Kristen in some ways, but similar in others. Even after a short time I could tell she was sweet and playful, but she was also self-confident like her girlfriend, as well as direct and unapologetic. It also took all my willpower to not try picturing the two of them together…in bed…with Cara’s long legs wrapped around Kristen’s head.

“You look lost in a thought,” the model observed.

“Suddenly was trying to recall the lineup of the 1994 New Jersey Devils’ Stanley Cup winning team,” I answered truthfully as that tended to stop my growing boner from getting noticeable.

“Fuck fuck fuck,” Kristen swore as she stormed out of the bedroom.

“What’s the matter love,” Cara asked.

“Seems like getting called to set and ruining a perfectly good Saturday is contagious today,” the lesbian answered before sharing she got called into a meeting for her upcoming picture.

“That’s shitty,” I replied, very confused.

“Og, can I ask you a favor? Would you mind entertaining Cara as I run off to this meeting. I shouldn’t be any more than 3 or 4 hours total,” Kristen asked.

“I’m cool with it if you are,” I answered looking over at the Suicide Squad star.

“Better than sitting at the studio, bored to tears,” Cara added. “Thanks Og.”

“Og, can you go pour Cara a coffee that I can smell,” Kristen commanded more than asked. “Two sugars, one milk. Thanks.”

I still had no idea what was happening but I continued to trust the actress for a little while longer. Why was she trying to pass Cara off on me? Was she trying to create distance between them? Not wanting to hang out with the model anymore? These were just some of the questions I thought as I poured to mugs of coffee. But after getting the milk from the fridge, I heard the two lesbians talking.

“Seriously Cara, don’t,” Kristen said in a more authoritative tone. “I know we don’t care about monogamy but he does, and so does Anna. Og is completely hands off.”

“Okay, okay. No need to get all bitchy about love,” the model-turned-actress agreed.

“Alright, my bad,” Kristen replied before I heard a soft kissing sound. “He’s a good guy and cool so I’m leaving you in good hands at least.”

“Your coffee,” I offered the mug to Cara as I re-entered the room.

“Thank you,” the model said, accepting it.

“A word Og,” Kristen said as she picked up her purse and headed towards the door.

“Kristen, what was that about? It’s not like I would actually try to fuck your girlfriend but you didn’t have to lie to her to get her to keep it in her pants for your benefit,” I told the redhead.

“Oh Og, so handsome and yet so dumb,” she said, completing the patronization by patting my cheek. “I did that for your benefit. By telling her that you had off limits, it’s making her so horny that she’s gonna throw herself at you.”

“Okay…but why? I didn’t even get the feeling you liked me…at all,” I followed up, trying to make sense of it.

“I don’t, not really. However, I can appreciate your talents,” Kristen looked over her shoulder to make sure Cara wasn’t around then continued. “We can use each other here in a mutually beneficial way. You get to anally fuck my hot, lesbian girlfriend and in return I get back Cara who is willing to experiment with butt stuff now.”

At this point my head was spinning. Not only did Kristen Stewart want me to plow her girlfriend, but sodomize her as well. She went on to explain that she’s been dying to play with Cara’s asshole, especially with her favorite strap-on, but the leggy model has rebuffed her at every chance.

Then she thought back to how great of an anal lover I was. In fact, with the way she remembered it fondly plus the way Anna gushed about it, Kristen knew I’d be perfect. Anna was a lot of things but she wasn’t known to withstand a hard fucking, but Kristen had vivid memories of me laying wood to her ass fast and deep…and her loving every second of it.

“So just return her loving anal…or else I’ll come back here in the middle of the night and crush your nuts with my bare hands,” the fiery ginger added.

“So let me get this right. I’m to seduce your girlfriend then be her anal trainer,” I replied, still in disbelief.

“Yup, couldn’t have put it better myself,” Kristen replied with a cheery smile. “By the way, I left you some goodies in your sock drawer to help when it’s time.”

Within minutes Kristen was out the door and going God knows where. Maybe she actually did have a meeting that she scheduled behind Cara’s back in order to get me and the model alone. I have no idea how her devious mind worked, but I knew what I had agreed to so I racked my brain as to how to start.

“Cool, you have Smallville. Mind if we watch some,” Cara offered.

“Yeah of course,” I replied, figuring it would be like research for her.

“Is my character Enchantress in any of them?”

I racked my brain as I thought back over the 10 season show before answering in the negative. However season 8 had some Suicide Squad storylines so I suggested that to the leggy actress and she was more than happy to settle for that. She had fallen in love with the character and team during filming and now wanted to absorb all source material.

We both sat on the sofa as I flipped through the episodes until finding Suicide Squad centric episodes of the corny yet genre defining show. IT had some members from the film like Rick Flag and Deadshot, but sadly I was right and there was no Enchantress. Throughout the few episodes we moved closer and chatter easier, getting to know each other better and even flirting some if I detected right.

“Can I use your bedroom for a moment,” Cara asked, already standing up.

“Um…yeah, of course. Right through there,” I said, pointing the way.

I couldn’t help but watch her tight ass as she rose from the sofa, grabbed her purse and swayed her way to the room. Her legs really did go on forever I noted as they emerged from under her short sun dress.

I continued to watch the movie but after a few minutes I began to wonder what happened to the leggy model. She was probably just on the phone, probably with Kristen. Maybe she was pleading with her girlfriend to cancel the meeting and come back. Maybe she was bored. Was I boring her?

“Og. Can you come here,” Cara called from my room.

Wondering what she was up to, I rose from the couch and opened the bedroom door to a sight I most definitely wasn’t expecting. Changed out of her casual dress, Cara was laying on my bed with one of my dress shirt completely unbuttoned but just covering her breasts. Her only other remaining clothing was a pair of long black socks that went to her mid-thigh, meaning I had an unobstructed view of her hairless pussy that looked as pink and inviting as I had ever seen.

“Cara…wow,” I gawked slackjawed.

“Well don’t just stand there silly. Come on in,” the model instructed.

Like a mindless idiot I walked into the bedroom, my eyes never leaving her body. I glanced at everything from her face that wore an expression that begged me to take her right then and there. Then continued down to stare at her naked breastbone, the hint of her inner tits just visible before my shirt covered the rest. And of course that bald cunt!

“What…um…are you doing,” I asked, slowly recovering.

“Seducing you,” she replied matter-of-factly, her hand between her legs and playing with her pussy.

“I can’t” I forced myself to say, putting trust in Kristen.

“Why? Don’t you like me,” Cara replied.

“It’s just that…well I kind of have this girlfriend…and we are, well, together,” I stammered, that not being an act.

“I don’t want you to think about that right now. I just want you to think about this.”

She had sat up straight so that she could reach up and take my chin between her thumb and finger. With being both firm and gentle at the same time, Cara guided my face down towards her. She gave her lips a lick to wet them before she pressed her mouth to mine as we kissed for the first time.

I had never tricked a girl into giving up her anal virginity to me so I was playing everything here by instinct. Therefore, I allowed us to kiss for awhile longer, letting her anticipation build while also giving her the impression my will was all but broken. As our tongues began to dance in the interspace between our lips, I pulled back suddenly.

“I can’t do this Cara. I love Anna,” I acted though meaning the second part.

“She doesn’t have to know,” the leggy model replied, kissing my neck.

“But I would.”

“Og, I’m so horny and want a cock. Please! Fuck me, I’m literally begging,” Cara pleaded, grabbing my wrist and placing my hand between her legs to feel her very wet pussy.

“I…don’t think so.”

Cara seemed out of ideas, I no doubt believed she didn’t think anyone could have withstood this amount of pressure. We both knew she had one last card to play but I wanted her to play it, not for me to prompt her. I realized I was still stroking her velvety folds so I stopped and was starting to pull my hand away when she broke.

“What will it take,” she asked, looking me right in the eyes. “I’m willing to do anything.”

That was the ticket I was waiting for and she finally gave it to me. Instead of pulling my hand away, I left it between her legs but instead of rubbing her snatch once more, I went even lower until the pad of my middle finger could reach out and rub her crinkled starfish. To the model’s credit she didn’t flinch at all as I began making small circles around her asshole, just holding my stare the entire time.

“Is that what’s it gonna take,” Cara questioned, the intensity in her eyes making my dick harder.

“Yes. If I’m going to cheat on Anna…you have to give up your ass,” I replied, hoping (correctly, I found out later) that Kristen had told the girl about my prowess with giving girls pleasure through anal.

She fixed me with a long stare as if weighing if that was worth it. Finally her hand went to my crotch and began rubbing my already hard cock. “Wow. No, no anal. You are way too big for my little ass. And just think how tight my pussy will be, I’m a lesbian after all. It’s practically untouched.”

I couldn’t help but grow even harder between my legs at her last comment. Her snatch would probably be the tightest I would ever experience based on the fact a cock wasn’t a frequent visitor inside her. Plus she was so thin and yet athletic. Plus it looked so tasty! But no, I had a deal with the devil…errr Kristen in place.

“But you said I could do anything I wanted. And that is my condition. You clearly wanna have fun and I can guarantee that not only will you like it, but I’ll make you cum,” I pleaded, hoping that I could back everything up.

“I don’t know. I haven’t done anal before,” she reconfirmed.

“How about just a finger? Look how small it is,” I said as I showed her my thumb.

“You think I’m so foolish? It’ll start with just your thumb then you’ll get caught up in the moment and go too far,” she claimed. “First it’ll be one finger then you’ll add a second then you’ll ask if you can see if the tip fits. So no anal.”

“Just one finger and I’ll stop pressuring you,” I retorted.

I saw that there was a weakening of her will so I pressed on, wanting to break down that wall altogether. Keeping her mind flooded with sex I started to really rub her pussy and kiss the side of her neck. I could hear her moan with this so I upped the ante further by using my free hand to push my shirt from her body and grope her firm, perky tits.

After a bit of thinking, Cara finally answered, “Okay but just a finger.”

I could tell that Cara was concerned, but how could I not be overjoyed that she had actually said yes. Needing to make sure I kept things moving along before she thought twice about the arrangement, I got her quickly set up on hands and knees with me directly behind her plump, rounded ass.

I no doubt believe she could hear me wet my thumb since I could, but I had to be sure to transfer as much spit onto the digit as possible. She couldn’t help but jump a little bit when she felt my palm contact the top of her ass. I slowed down and just rested his hand there until noticing that the model had calmed herself. Slowly lowering my thumb downward, I stopped when it was pressed against her tightly clamped butthole.

“Just be gentle,” she pleaded softly, looking back over her shoulder with her gorgeous eyes.

Nodding in agreement, I started to apply pressure. I knew she was still rather tense, but the combination of my urges and her not backing out made me press on until I saw that the hole was starting to gradually expand until finally the first part of my thumb disappeared inside her backdoor altogether.

“Ugghhh…awww,” Cara moaned as my thumb slowly was worked into her virgin hole.

“See. I told you it wasn’t that bad,” I said to her after a few more moments of pushing the thick digit into her rear and getting very positive groans as a result. “In fact, I knew you’d like it.”

“Mmm…yeah I like it,” she admitted honestly with lust in her eyes as she looked back at me. More than her confirming words and sexy look, it was her wide smile that was so telling.

“How much do you like it,” I asked, burying my thumb all the way into her asshole.

“A lot…ahhh,” she groaned.

“Enough to let me try something…similar,” I proposed.

When Kristen had pulled me aside, she had mentioned she had left a bag behind in the room with all types of toys including something I recognized from when she and Anna fooled around. Pulling the red beads from the bag, I held them up so that the leggy actress could get a good look at them, then I placed my thumb next to it as a size comparable. It was true that the beads were slightly larger, but not by a lot.

“Og! You naughty boy. Beads,” she continued to exclaim. “You want me to put these in my ass?”

I did and I told her as much before handing her the toy that consisted of 4 spheres all connected by a string running through the center of each. I wanted her to hold them and see how non-threatening they were, while also serving a purpose. While it was true I really wanted to see them buried in her tight little ass, it would also loosen up her bowels for when I tried putting my larger dick in her.

“But you said just a finger,” she threw my words back at me from earlier.

“Just put them in your mouth, it’s really no bigger than my thumb,” I retorted.

Even as I was saying the words I was grabbing the end she wasn’t holding and bringing it up to her face. Like the submissive girl she was she parted her lips and let me place the ball onto her tongue before closing up again. Seeing the little grin on her mouth as she spat it out, I asked if she could fit more than one inside.

Cara may not have been an anal-craving slut, but she was sexually confident and very playful. Seeing it as a fun little challenge, she took back control of the toy and surprised me by fitting a ball on the inside of each cheek and a third on her tongue before closing her mouth. She decided to have some fun and slowly pulled them free, going slowly so I could see her plump lips sexily slide over the surface of all three.

“See. It’s no big deal.”

“Yeah well my mouth is a whole lot bigger than my butt,” Cara replied, slapping her ass to make her point. “You saw how tiny it was.”

“But the elasticity…”

“Ugh! Men! Just go get me a bottle of the cheapest liquor you have,” Cara groaned though I doubted she was that upset.

I couldn’t believe my ears. The plan to gradually work her up to allowing me to put my cock in her ass was actually working. I guess it was aided by the fact that the gorgeous model appeared to be a sex-craving whore, but that shouldn’t have surprised me given she was dating Kristen Stewart of all people.

Not wanting to push my luck with the beautiful girl, I got up from the bed and left the bedroom to go into my liquor cabinet. There were a few options, in fact more than a few given how Anna loved getting drunk, but I ended up picking a pint bottle of whiskey. Rye in fact from a visit to Canada but it would easily do the trick.

“How’s this…”

I cut my words off in a hurry when I saw that Cara was now laying on her side, legs pressed together and ass towards me. While the sight of her naked little booty and cute dimples on her low back were enough to make me blush, what made my jaw drop was the red string dangling on one cheek and the rest obviously hidden behind her sealed tight sphincter.

“Still can’t believe I’m doing this,” the slim actress commented as she reached her hand towards me. “Give me that.”

I handed off the bottle of amber-colored fluid and before I settled on the bed behind her she had the cap off and a healthy mouthful swallowed down. With both hands free I grabbed the string that was dangling out of her and held it firmly as my eyes never left her ass…more specifically her insanely tight asshole. How she managed to get all 4 balls in before I got back was a mystery.

“Just go nice and slow,” she told me before choking back another mouthful.

“I’ll be gentle. You just pull your cheek apart,” I urged.

I wasn’t surprised at how much effort it was taking to overcome her muscular ring especially with how slowly I was going. Maintaining steady pressure backwards I switched my gaze between her asshole and face before I saw my efforts rewarded. Cara’s face started to contort with her brows furrowing and her mouth gaping as her asshole did likewise and the faintest hint of a red ball could be seen inside her.

Still pulling in a smooth motion, I kept going and watched as her asshole continued to expand and more red came into view. I think I told her to spread more as I saw the veins in the back of her hand pop but it did the trick. Her sphincter opened to its new limit as a lubed-up red sphere came popping out from her backdoor.

“Hhhh….ahhh,” Cara moaned as the first bead left her ass.

“That’s one,” I celebrated, taking a break from pulling. “Ready for the next part?”

“Wow. Okay, not horrible. Yeah…ughhh…yeah,” she groaned as the next part was slowly withdrawn from inside her rectum.

I hadn’t waited more than a heartbeat after she said yes and had pulled the second ball loose with less effort than the first while still being sure to be gentle. But as it came free of her backdoor, I couldn’t help but smile in surprise since the slutty model was clearly liking it as much as she was.

“Here we go again,” I warned before slowly starting to rear back on the string.

“You like that? You like watching it come back out of my ass you dirty, dirty boy,” the model dirty-talked. “Awhhh…oh my God…ahhhh!”

This time I went even slower, but only once I saw the third red ball start to open her asshole. As she slowly expanded I practically crawled to a stop so that she could really feel me opening her tightest of balls with the lubed-up toy then held it steady as it reached it’s apex, gaping her more than an inch before pulling it out and watching her seal back up but less quickly this time.

“Last one,” I said as I pulled.

This time we were both aware of what I was playing at so as I nearly stopped with the ball holding her ass as far open as it could go, Cara pulled back hard on her ass cheeks. The 4th and final sphere slipped out of her loosened butt and fell to the bed below.

Wanting to show her what she had just accomplished and to be proud of it, I lifted the string of 4 anal beads up towards her face. I was once more shocked by the model as she clutched my wrist and kept guiding my hand towards her face until she was close enough to take the first bead in her mouth. Like before, she ended up with 3 between her lips…3 anal beads…fresh from asshole…seconds before hand!

“Have any more cool toys in your goodie bag down there,” Cara asked after spitting out the beads that had just been down her dirtroad.

As a matter of fact I did spy a toy that would be perfect for the model before graduating her to my cock, which would now definitely be happening. Reaching inside once more this time I revealed a bubbly black dildo for her to see. It was roughly 6 inches long with each inch bigger than the first with it beginning the size of his thumb and bubbling larger as it went back until it was the size of an egg.

“Holy crap! That’s so big,” she gawked, grabbing hold of it. “And heavy! You really think I can fit this?”

The fact that she asked the question instead of outright refusing was the only encouragement I needed to hear. I nodded and smiled wide as she went about comparing the anal beads to the dildo, the first rung of the toy being roughly the size of a sphere before getting larger and larger.

“See, about the same size,” I added.

“Are you blind?” She was right of course, as even the first bubble of the dildo was bigger than the bead…which was bigger than my thumb. “Og, what are you doing to me.”

“Here, I’ll put on the lube,” I suggested, already smearing the toy before rubbing a healthy dollop over her backdoor. “And you try with the dildo. You have complete control.”

“Well I guess I could try at least,” Cara said. “But there is no way I can fit all that in this ass.”

“One way to find out,” I said.

Cara was already set back up on her hands and knees with her chest resting on the bed and her booty way up in the air. I loved the fact that her asshole glistened as the sunlight hit the copious amounts of lube on its surface and she looked so sexy naked except for a pair of thigh-high socks.

“Okay…okay,” she said as she placed the rounded tip against the crinkled surface. “Just gonna go nice and slow.”

She started pushing as I could see her forearm tense before transfixing back on her ass. Sure enough, the anal beads had loosened her up as it was only after seconds before her hole spread and the first bubble of the dildo disappeared inside her ass. To my shock, she didn’t just hold it in but instead slowly fucked her own ass with the initial tip of the toy.

She was a smart girl and understood that momentum meant a lot so she kept the toy sawing slowly in and out. I was so hard and found my hand stroking my cock as her asshole constantly widened and shrank until she got to the tapered end of the first bubble. Without breaking stride she tensed her forearm again and pushed until the second part disappeared in her ass as well.

“God! Uhhhh,” Cara screamed as she had over 2 inches of a thick toy buried in her virgin asshole.

“You’re doing amazing,” I said as my free hand closed over the dildo. “Let me take it from here.”

The model had no issue giving up control as she released the toy into my stead and I immediately continued her good work. Pushing with steady force I didn’t relent until a third bubble pushed into her behind which was met with louder cries, but none were of pain. But as soon as it was in, she reached back and took control, apparently only needing me to get over that last bump.

I didn’t mind as I watch while she fucked herself with the new thicker inch in her ass. The English model was nothing short of a mystery and I was stuck happily in her web, waiting to see what was next. With a firm grip she pulled the third bubble out, then the second before completely removing the toy and I saw her asshole seal as tight as if nothing had ever been permitted inside.

“My bum still pretty,” the model-turned-actress asked with a confident smile.

“Oh yes,” I replied as she thrust the toy back in, easier than ever.

First one bubble then a second went inside without issue before backing out the toy completely once more. Apparently with new found anal confidence, Cara fucked herself with the first two rungs before building speed and thrusting the third level inside next. I was transfixed as I watched the skinny model fuck herself faster and faster while my hand rubbed my own dick with increasing speed.

“Oh my God,” Cara screamed as she pulled the glass dildo from her ass. “How far down did I go?”

“Right here,” I said, pointing to the spot.

Her face was of pure elation as her thumb moved along the groove of the third and fourth bubble. Without hesitation she stuck out her tongue and licked the portion of the toy that had been wedged in her own ass, starting at the third bubble and going to the top. At this point she opened up wide and sucked clean the first portion of the toy for a few bobs before lowering herself further and doing the same to the dirty second and third parts as well.

“I got one more thing for you,” I told the model.

“What’s that,” she asked with a knowing smile.

“Undo my pants and I’ll show you,” I replied as we stared deep into each other’s eyes.

“You gonna be good to me,” Cara asked, that smile never faltering for a moment.

*          *          *

Kristen Stewart actually did have a meeting but it wasn’t for a studio but rather a monthly meeting with her agent. It was a fluid thing that could have been anytime, but the redhead wanted to make herself scarce as Og did his thing with her girlfriend. It irked her that she needed to use the man to get Cara to do something sexually, but if it meant getting to peg the gorgeous model then she was willing to swallow her pride and arrange the deal.

Her meeting with her agent lasted roughly an hour, which meant she had several more to kill before showing back up at Og’s apartment. She didn’t know if the handsome man would call or text when they were all finished up so she planned on just going back around 4pm. Bored, the fiery redhead pulled out her cellphone and dialled a familiar number.

“Hi sugar tits,” Kristen spoke into her phone.

“Back at you sweet ass,” Anna Kendrick replied with a giggle. “What’s up.”

“Nothing, just chillin as the kids say,” the redhead replied.

“Chillin huh? Or freaking out as my boyfriend sodomizes your girlfriend while she screams out his name,” the Pitch Perfect star got to the point.

“Bitch,” Kristen swore. “Maybe we gave him too much credit and Cara will call any second in tears, saying what a jerk Og is.”

“I’d take that bet,” Anna retorted.

“Yeah…I know.”

*          *          *

I decided against jumping straight into pummelling the girl’s virgin asshole. Even though she had exceeded expectation with the toys, I could still sense some nervous energy from the blonde so I went to something she was more comfortable with.

“You yes Og…lick that pussy,” Cara moaned as my tongue swiped up and down her bald cunt.

Of course I didn’t leave her bum alone for very long. Breaking briefly to suck on my middle finger, my mouth immediately went back to her pussy while the digit pushed against her sphincter. After being used for the past 30 minutes, she was relaxed enough to let my finger glide right in and I built on that momentum, fucking her fast as my lips latched to the top of her box and my tongue darted at her clit.

Since Cara’s ass had no trouble eating up my first, I decided it was time to add a second. Her screams died down as I stopped my oral assault on her clit, but her moans took on a new sound as I pressed the new wettened digit with the first and wiggled into her virgin butthole. It was tight and I couldn’t fuck her as freely, but it was still progress.

“Mhmmm…yeah,” the Suicide Squad moaned, her own finger taking over clit-rubbing duties from me.

With Cara laying on her back, I had her use her hands to pull apart her cheeks so that I could get faster in finger-fucking her tiny ass. Of course after a minute or two of this a pulled out and replaced the digits with my tongue, able to reach as far into her dirtroad as I could. Of course the model reacted so loudly I feared my neighbors would complain, but I was rimming a gorgeous Victoria Secret model so I could care less.

I kept munching at her adorable butthole while my hands worked furiously to rid myself of the jeans I wore. When it came time to remove my shirt, which required me to pull my tongue away from her asshole for the first time in minutes, I was pleased to see that the actress was using her own fingers to alternate between rubbing over the rosebud and actually fingering her own ass.

“You want it? You want this small ass,” she asked, dipping inside the tight hole. “Finish losing the clothes and get on your back.”

As Cara moved over on the bed so that I could lie down when naked, I saw her pick her head up when she was sure I was stripped bare. She soaked in my naked form but her eyes came to rest on my thick, 9-inch pole. She was actually bisexual since she’d been with men in the past, but not for awhile so seeing my monster made her eyes bulge in nervous excitement.

I climbed atop of the soft bed and laid down facing the ceiling in the middle with my head nestled in the pillows. Cara didn’t give me a chance to settle as she already had her leg swung over my powerful torso with her hips dangling over my lap. Descending slowly, the second she felt my unsheathed penis brush her folds, she sank down further on her knees and popped me into her pussy.

“Fucking hell you’re tight,” I grunted as she enveloped the first several inches of my cock into her velvet-feeling hole.

I didn’t know how long she and Kristen had been together, or more importantly when the last cock she took was but judging from how tight she was, I was willing to bet it wasn’t for a long time. It was a good thing I went down on her earlier and got her good and wet or else there was no chance I could fuck her this quickly.

“Thanks,” she muttered as she took the rest of his massive dick into her pink hole. “Damn that feels so good.”

Smiling, I sat back and allowed the sexy model to do the work above me. Her pace, which had started slow, had picked up considerably. Raising quickly before slamming herself down into my lap, the horny girl was doing her best to get off quickly so that I could have my way with her anyway I saw fit.

“Oh shit…fuck…yes, yes, yes,” Cara shouted, her orgasm building. “Make me cum and you can put it anywhere.”

“Anywhere,” I asked knowingly.

“Fine! I’ll spell it out for you Og. Give me my orgasm and you can shove that fat cock in my tight, virgin asshole. That clear enough for you,” she asked.

I had my doubts at the onset of Kristen’s challenge to me earlier in the day but hearing the model state that promise so clearly gave me crystal clear focus. All I could now think about was giving Cara the orgasm she so badly wanted so that I could fulfill my own (and Kristen’s) deviant fantasy.

With her still sitting in my lap bouncing along the entire length, Cara freed my hand from clutching her breast and brought it towards her face. Opening her mouth, she isolated one of my fingers and moved it into her mouth, simulating a blowjob in order to get my middle finger coated in her spit. Once sure it was sufficiently wet, the horny actress guided it down and around her body until it was resting on her curvy ass.

I instantly knew what she was playing at but wanted to give her some control, making her essentially beg to get her booty played with. I took over from there and placed the wet digit on her constricted asshole, rubbing it around but never penetrating, not this time.

“Once I cum you can do more then rub your finger,” she whispered into my ear, thudding her ass continuously into my thighs.

“Then I should make that happen,” I replied with a cocky smile.

No longer holding anything back, I pushed my hips forward so that they crashed into Cara as she was descending on my tool. The collision made a loud wet slap as flesh crashed against flesh but it achieved penetration deeper than the model had experienced.

“Fuck…I’m so close,” Cara screamed. “Keep fucking my tight like twat!”

I knew that she was a woman who liked her ass played with so I slid the wet finger into her backdoor the next time she plummeted in my lap. Cara squirmed at first, but she was so lost in her own pleasure that she barely noticed after the initial penetration. Seeing that she hadn’t had her screaming orgasm just yet, I pushed a second digit inside her asshole so that both of her holes were being stretched and probed.

“OHHHH….YESSSSS,” Cara shouted at the top of her lungs as she gushed her juices onto my fat dick.

Losing control of her bodily function for a moment after her intense orgasm, the sexy model collapsed down onto my chest so her perky tits pressed against me. Stroking her hair, I let the leggy star recover rather than push her into more sex, especially when at the beginning of the day she made anal sex a clear no.

“That was hot Cara,” I complimented from beneath her.

“Mmhmm,” she agreed. “So how do you want me?”

“I think you’ll do best with doggy,” I replied.

I felt the model take a few more breaths atop of me before she pressed herself up while swinging her leg off of me in the process. Like the position she was in during feeding her own ass the dildo from earlier, Cara got onto hands and knees with her head up by the head board. In one smooth movement I was on my feet, bottle of lube in hand and smearing both my dick and her virgin asshole.

“Mmmm,” she moaned in response to the cool, wet touch.

“You ready,” I asked, kneeling behind her, tip already brushing her rosebud.

“Just be nice to it,” she pleaded.

I nodded then took a breath to steady myself. Never in my wildest dreams did I ever think that I’d be taking Cara Delevingne’s anal virginity. Then again until last year I didn’t think I’d be dating Anna Kendrick, or have fucked Alison Brie or had a threesome with Kristen Stewart. I was either the luckiest mother fucker in the world or I had a sexual guardian angel looking out for me.

“AAWWWHHH YEESSSSSS,” Cara screamed as my head popped into her.

“It feels so small,” I groaned from above her.

“I can take it,” the model insisted. “Just slide that wet dick in my ass.”

“It’s so fucking tight,” she swore in agreeance.

I would only find out later as we talked about her experience that Cara wasn’t consumed in pain like she expected or like so many girls had during anal sex. We had done a thorough job stretching out her elastic hole so that even though it didn’t feel great, it was only some minor discomfort as I first stretched her asshole around my giant cock.

I normally would have started a lot slower but just from reading her body language I knew the leggy lingerie model was ready for more. Not stopping at the tip, I slid more of my lubed up cock until I sensed her tighten up. I sat still for a moment and looked down to find that more than half my length was in her ass!

“Good girl…taking that cock so well,” I congratulated as I began pulling my hips back.

Now knowing where her limit was, I stayed within it, constantly pushing in and out only half my length. I didn’t go very fast but now wasn’t the time for speed, it was the portion that she got comfortable with anal sex. Deciding she was ready for more, I grabbed her wrist and placed it between her legs and let her instincts take over.

Like I expected, the lesbian began to rub her clit and the rest of her folds and I could feel the shift in her muscles. More relaxed, I opted for pace rather than trying to cram inside deeper and was rewarded for my decision. Even though it was only 5 inches in her butt, I was plowing her just as fast as I had done to her pussy minutes earlier.

“You like fucking my little ass,” she asked him. “Working that fat cock in my ass?”

“You fucking bet I do,” I answered. “And you’re doing so good. I’m already halfway in.”

“I can take more. Give it all to me Og,” Cara demanded greedily. “Stuff your whole cock in my small ass!”

Delighted to hear that she was so into the anal sex, I slowed my pace to about half speed but started probing deeper. After every inch or so I would speed up and stay at that depth for awhile before plunging down again. Finally deciding now was the right time, I gave Cara what she wanted and pushed the rest of my shaft into her until hips slammed against her curvy ass cheeks.

“Oh shit,” she groaned in a combination of pain and pleasure as I stayed balls deep in her tiny hole.

“You okay Cara,” he asked after hearing her sharp yelp.

“I’m good. I can take it,” she told him confidently.

I would have stopped if she wanted, but I was over the moon that she didn’t ask that. Unhurriedly, I pulled most of my shaft from her bowels before slowly working it back in. My hips touched her ass cheeks at a much lower speed then the last time I fully entered her ass, much to her liking.

“You like having a cock worked into your asshole,” I asked, engaging her in the dirty talk she started.

“Yeah I do. I’d like it more if you took the training wheels off and really gave me a ride,” she replied, catching me by surprise.

Pulling out almost completely, I crashed my hips against her ass, causing it to ripple. It drew a sharp scream from her again, but when she looked back at me, her glance told not to stop fucking her. Listening to her silent instructions, I did the same thing and smiled with glee as my dick disappeared within her asshole.

I was finding my stride now and I wasn’t looking back or stopping for anything. I just seemed to tune everything out, including the burning feeling in my balls as it just felt like I could sodomize this skinny model all day and night. I slapped her ass, first the left cheek then the right all while looking down and watching as my entire dick would disappear then reappear every second or less.

“Such a dirty slut. Only sluts take it in the bum,” I told her, demeaning her further.

“Then I guess I’m a filthy anal whore,” she replied. “Now really fuck this big slut in her tight ass!”

“It won’t be this tight ever again, not after I’m done with it tonight,” I told her while slamming into her asshole again at a quicker speed.

“Yes! That’s it! Fuck that ass! You know I fucking love it,” Cara continued her encouragement.

Even with my cock gliding smoothly in and out of her ass, I was content. Giving her cheeks a firm squeeze, I pulled back my right hand and let it come crashing down onto her backside. Instantly her creamy white skin started to turn red and she let out another yelp of pain mixed with pleasure.

“That cock feels so good in my ass,” Cara told me while continuing to rub her sensitive clit with her finger.

“Good…because that’s a lot of dick up your ass,” he replied. “Now I want you to taste it. Suck your own ass Cara. Be a good ass slut.”

Without needing another prompt, Cara spun around when she felt I withdrew from her ass. It felt weird to not have my dick filling up her rectum, and I felt that she was probably feeling empty and missing it as well. Grabbing my cock at the base, Cara shoved the first half into her mouth and started to noisily suck on my offering. It was the third time that night she licked something that had been lodged deep in her bowels, and for a third time, she liked the taste.

“Yes. Taste that dick with your ass all over it,” I demanded. “Suck your own ass!”

She did as I asked by giving me the sloppiest and probably loudest blowjob I could have imagined. She was not in Anna’s league, no one was actually with her ability and preference to deepthroat my cock, but Cara was thorough. Only able to bob on half my length at most, she emitted loud gurgling noise with more spit decorating my dick each time she bobbed downward.

“How about we get this cock back in my ass,” the sexy model said as she pulled her mouth from my manhood.

“Thought you’d never ask,” I replied with a wide grin. “But I want you to ride it this time.”

“You want me to fuck my ass then I’ll ride the shit out of your dick with my tight little ass.”

Crawling upward on the bed, Cara hovered above me for the second time this night. This time, as she lowered herself, she took the cock towards her further back hole rather than her pink one she had done earlier. With me pressing against her puckered bum, she sank down on her knees further until I re-entered her butt.

“Such a tight ass,” I commented as I slid back inside. “Come on Cara. Fuck your own ass.”

“Oh I’m going to fuck it so good you’ll be cumming in no time,” she retorted as she started to rise and descend on my entire length. “Fuck! Right there.”

With each pass into her rectum Cara seemed to gain speed until she was a blur atop of me. I had no idea how she could bounce so quickly, especially since we had been having sex for quite some time already but she showed no hint of fatigue. Her body was covered in a layer of sweat that made her creamy skin glisten in the sunlight.

Normally I wasn’t such an animalistic lover, in fact with Anna I was a lot more tender but for whatever reason Cara Delevingne was bringing out the savage in me. Not content to have her do all the work I was viciously pumping my cock up into the first-time anal lover, driving into her ass deeper and faster than either of us thought possible.

“God you are taking this in your asshole so fucking well,” I commented without skipping a beat.

“Holy shit I think I’m cumming,” Cara screamed as she continuously rode my massive cock.

I was completely flabbergasted and said the first thing that came to my mind. “No. Only huge anal sluts can cum with a cock in their ass,” I teased.

“Then I’m a giant slut because I’m so close,” she warned, not picking up my tone of joking. “Ohhhhhh….yesssss!”

“Would it help if I slapped your ass again,” I asked before smacking her slim yet perfectly  shaped cheek.

“Yeah…Ughhhh….getting close,” she moaned. “It might help if you pulled my hair too.”

Loving the fact that Cara was getting off by being disgraced like a common whore, I kept slamming my dick into her ass. Still slapping her ass, I reached up, twisted my hand in her wild hair and wanked it downward as hard as I could. It was something I never would have even thought to do with the more fragile Anna, but with Cara she was urging me on.

“Ahhhh. Oh my fucking God! Awwwhhh,” she grunted in pure elation. “Ughhhhh. I’m cummingggggg! I’m fucking cumming! Don’t stop fucking my ass!”

I was happy she came when she did because I was in desperate need of release as well. I let her ride out her orgasm, which she did but sitting deep in my lap and grinding against me, my manhood as far into her bowels as it could go. Her screams were ear piercing but thoroughly deserved, surprising herself by cumming from anal sex.

Once I was sure she had cum and was done, I pulled her off of my lap and let her fall onto her back. Climbing atop of her so that I was straddling her small but perky chest, I stroked once or twice until the familiar feeling of cum starting to migrate from my balls overtook me. Knowing that the last act of degradation would be to cum all over the model’s perfect face, I took aim and waited.

“Cover me,” she said through exhaustion but still upbeat. “Cover my fucking nasty face.”

“Oh shit,” I shouted before doing just that.

Like most girls, Anna wasn’t the biggest fan of taking a cumshot to the face so since they were rare I kept my eyes open this time as I climaxed. I watched as the the first rope of cum propelled itself and streaked across Cara’s nose all the way up to the forehead. The second streak hit the same target then I decided to paint another area of her pretty face. This time I splattered into her closed left eye while the fourth jet hit the side of her head and nestled into her dyed blonde hair. The last remaining squirts didn’t have the same quantity as the earlier ones, but there was still enough left to coat the rest of her face.

“Oh my God,” I cursed.

“Glad you enjoyed yourself big boy,” she told him before sucking on his sensitive tip, tasting herself for a final time.

“Tissue or the bathroom and shower are straight through there,” I offered.

“With this much cum I’d better go shower if you don’t mind,” Cara answered before disappearing into the on-suite washroom.

Once I heard the water of the shower turn on, I pulled out my cell phone from my discarded pants and dialed up Kristen’s mobile. I figured it would be on silent if she was still in her meeting but after it rang once it was immediately answered.

“It’s done,” I told the redhead. “And might I add you got a real dirty one on your hands.”

“Yeah? How’d she do,” Kristen asked.

“Well, at one point she demanded I bend her over and fuck my ass like a dirty whore,” I said, giving her girlfriend the direct quote.

“Thanks…I guess. Be there shortly,” Kristen answered before hanging up.

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Re: Dating Anna Kendrick
« Reply #4 on: November 27, 2019, 11:02:24 PM »
Happy to have you here Chemist, I've been a big fan of your stories on Adult Fan Fiction.  I gotta ask though, at one point wasn't there another part to the Super Bowl bet story involving sex after the game.  I swear I have a memory of one, either that or I dreamed one up at some point.
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Re: Dating Anna Kendrick
« Reply #5 on: November 28, 2019, 10:51:08 PM »
Thank you for sharing all of these wonderful stories with us. You are one of the best erotica writers out there  :Y:

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Re: Dating Anna Kendrick
« Reply #6 on: December 06, 2019, 10:40:19 AM »
Title: Dating Anna Kendrick Part 5 - Perks of Dating Anna Kendrick
Author: The Chemist
Celebs: Anna Kendrick
Codes:  MF, anal, oral
Disclaimer: I do not know Anna Kendrick. This story is an act of pure fiction, therefore didn’t happen. I make no money from this story.

Summary:  Anna arrives home early from a shoot and decides to surprise her boyfriend at home for some long-awaited love. PWP essentially.

I was enjoying a hell of a shower when the sound of a knock on my door peaked my interest. Normally, I’d have continued on with showering but the pattern of the knock, the rap-rap-pause-rap indicated that it wasn’t a delivery at the door, but someone special. Rather than finish with standing with my chest and face in cold water for the last minute, I quickly turned the knob on the tap, bringing an end to the cleanse. Grabbing a towel I used it to try to wipe as much water off my skin as possible before wrapping it around my waist. I considered foregoing the towel altogether knowing who was on the other side of my door, but I was still modest at heart and there was always a slim chance I was wrong.

Rushing to the door I opened it and smiled wide when I saw Anna Kendrick on the other side. Though it had been over a year of us dating, it was still sometimes hard to believe that this gorgeous creature was my girlfriend. It was also an especially added bonus seeing her today since she wasn’t expected to be back in town until tomorrow. However, here she was at my apartment wearing a pair of those high waisted jeans that were all the rage these days, though they were more baggy than the form-fitting denim she typically wore. She rounded out the outfit with heeled boots to help add some height to her petite 5’0 frame, as well as a low cut pink top that was simple more than trendy.

“You’re home early, babe.” I said, moving out of the way to allow her inside.

“I wanted to surprise you so I told a little fib and ‘mixed up’ what day I was leaving,” Anna answered, stepping into my apartment before throwing her luggage down.

“Consider me surprised then,” I replied.

Reaching out I grabbed her and pulled her to me. Wrapping my arms around her I pressed my lips to hers and had to restrain myself a little from just picking her up and dragging to my room. After a year of dating the gorgeous actress, I knew her body language enough to know that she had something else on her mind rather than just making out with me. Fortunately, Anna gave me a sign that even a blind man could see in the dark. When her hand went for the spot where my towel was tucked into itself and pulled it loose, I figured maybe she wanted more than just a little kiss in greeting.

“Bedroom?” I asked her, already steering her that way.

“Fuck yes,” Anna said, letting my towel drop to the ground and giving me a once over with her eyes.

“I take it you missed me...or part of me,” I said, picking Anna up and letting her wrap her slender legs around my waist as I carried her into my bedroom.

Reaching my bed I eased her down onto it and slowly kissed my way down to her neck. As I nuzzled her neck my fingers slowly traced their way down over her taut stomach until it was at the hem of her shirt. Kissing my way down past her collarbone I slid one of my hands back up around her back so it was underneath her. Realizing what I was trying to do she lifted up just enough to give me room to unhook her bra, then they moved back down to her shirt to lift it and her undone bra over her head.

“God damn,” I swore as her boobs were exposed.

Despite the fact that she was so short and skinny, Anna was truly blessed with an absolutely jaw-dropping bust. Though they may have only been C-cup, which were still above average, they appeared even larger given her petite frame.

Somehow, they were even better than she had been imagining for the past 3 weeks, not that he could rationally explain that. Huge for her size, perfectly round and suspended firmly in front of her with the cutest pink nipples, I had to remind myself to swallow and not drool. Having stopped making out with her to observe the fine specimens, I leaned back towards her, taking her left tit in my hand and began sucking. Anna wasn’t surprised by his focus being solely on her tits now, after all every guy or girl she’d been with focused on those beauties, including myself.

“Mmmm,” Anna moaned as I took one of her nipples into my mouth.

As I suckled on her nipple I let my hands wander down her flat stomach. Reaching the top of her jeans, I blindly undid the button and slid my hand inside. Finding her belly button I traced a circle around it with the tip of my middle finger before continuing on down until I reached the fabric of her panties.

Letting the nipple slip from between my lips I ignored Anna’s groan and started kissing down her ribcage. Despite her slender build, Anna was far from skin and bones as illustrated by her rather mountainous tits and underrated bubbly ass. As my lips traveled down over her stomach, I pushed on her pants until she lifted her aforementioned booty off the bed enough for me to push them down her thighs.

When I had her jeans down past her knees, Anna did her part by kicking her legs until they were dangling around her ankles and she could kick them off completely. Reaching her waist with my kisses I grabbed hold of her panties and peeled them down to reveal a small patch of neatly trimmed short pubic hairs right above her pussy. This was classic Anna. When home and fucking regularly, she went to the effort of waxing or shaving her snatch bald but while away and presumably not hooking up with others, she tended to go with a neatly trimmed cunt.

Tossing Anna’s panties aside I put my hands on her knees and pushed them apart. Looking up her body I saw a look of excitement on her face overtop her pillowy tits. Not wanting to just dive right in, I preferred to torture her just a little bit. Therefore instead of going right for her glistening pink pussy, I went for her inner thighs, planting several kisses on each and making the think woman shake with built up hormones.

“Please,” Anna moaned in anticipation.

“You know what I want,” I told her. Though I’m not always in the mood for dirty talk, after nearly a month without her, I wanted to make Anna beg for it.

“Lick my pussy, Og, please?” Anna pleaded, proving once again that very little got me harder than hearing her say something naughty.

Keeping eye contact with her I stuck my tongue out and lazily dragged it along the length of her sex starting at the bottom and finishing with a swirl around her clit. When Anna moaned and her eyes narrowed I gave her pussy another swipe, but this time I focused more on the hood surrounding her sensitive nub.

“Oooooh,” Anna moaned, resting one dainty hand on the top of my head.

This time when I flicked my tongue against her clit, Anna grunted and hunched her hips at me. Using my fingers to part her labia I moved my tongue down to twist and turn at her pink opening and collect some of her rapidly gathering moisture before moving back to her sensitive nub. I had fucked Anna Kendrick enough times to know how to really rev her engine and now that I was doing toying with her, I got to business.

“Oh yeah, oh eat me,” Anna hissed, tangling her fingers in my hair.

As she humped her hips at my tongue I grabbed hold of her ass with both hands and lifted it off the bed. Wrapping my lips around her clit I sucked on it hard, knowing the exact reaction I was going to get from the squirrelly woman. Knowing her too well, I managed to move a little to the side just in time as Anna’s body jerked and her leg kicked out.

“Holy fucking fuck,” Anna gasped as I draped her legs harmlessly over my shoulder.

Still sucking on her clit I felt the cheeks of her ass in the palms of my hands and remembered how much she’d liked having her ass played with. This worked out really well considering just how much I loved eating out her adorable butt. With that formly in mind, I crept a finger into the crevice between her cheeks and then moved it down until I felt her tight little asshole under my fingertip. Even though I wanted nothing more than to start fingering her asshole, the digit was far too dry currently so I contented us both with rubbing my finger around the outside of her anus while I continued stimulating her clit.

“Oh god, awhhh,” Anna moaned, using her legs on my shoulders to lift her ass even further off the bed, attempting to fuck my face.

Finally detaching my mouth from her clit I dragged my tongue through the folds of her pussy. Reaching the opening of her pussy I lapped up some of her juices with a couple swipes of my tongue before continuing down over the thin patch of skin separating her tasty pussy from her naughty asshole.

Even though she had to have known where I was headed, Anna still gasped when my tongue made contact with her asshole. Pulling the cheeks of her ass apart with my hands, I lazily worked my tongue around the rim of her backdoor. When she started to move her hips in an effort to push her ass against my tongue, I finally gave in and folded my tongue so I could poke it against the center.

“God, yes! Lick my ass, Og!,” Anna demanded, her grip on my hair tightening as I did exactly what she wanted.

“Whose the only one who gets to eat Anna Kendrick’s tiny little asshole?” I asked Anna between licks.

“Only you,” Anna responded, pushing my head back into position.

“You didn’t let anyone else eat your ass?” I asked her as I eased a finger into her pussy.

“No one else,” Anna said, a shudder of pleasure running through her body as I slipped the finger out of her pussy and moved it down to slide into her ass. “Only you.”

As if the events of the last year hadn’t already inflated my ego to massive proportions, first somehow getting Anna Kendrick but also having her hook me up with several of her insanely hot friends, knowing that Anna’s ass was pretty much my own personal playground pumped a little more air into it. Despite her miniature stature, Anna’s sex drive was practically unquenchable and that extended to butt sex, as she obviously liked it and yet I was still the only one with access to her holiest of holes.

Wiggling the finger in her ass, I went back to flicking her clit with my tongue. Predictably. This caused the tiny woman to moan and as Anna squirmed under my manipulations, I turned up the heat, sliding a finger from my other hand into her pussy. Still flicking her clit with my tongue, I started to saw my fingers in out of her holes so that as I drove into her wet snatch, I was exiting her backdoor then vice versa.

“Oh god, awwhhh, fu-fuck,” Anna panted as I pushed her to the brink.

Of course, I was never content with just the status quo, and neither was Anna. As previously mentioned, her sexual appetite was always yearning for more and more. Therefore, when I added a second finger to her pussy after a few minutes it seemed to be exactly what the slender yet busty actress needed. With a squeal, her grip on my hair tightened and her body went stiff as a board before her holes clamped down on my fingers - all tell-tale signs that the Pitch Perfect star was reaching the pinnacle of her climax. Glancing up her body, I saw her mouth frozen in a wide O before her body began quaking as her orgasm crashed through her.

Knowing that after she cum Anna could be a little thrown off with anal, I slipped my finger from her ass but kept slowly sliding two fingers in and out of her pussy as her orgasm started to wind down. If this was only going to be a quickie like we did while she was on set, then I would have slowed down and delayed her orgasm so we could fuck, but this definitely felt more like a multilpe-climax session for Anna. Therefore, when she finally went completely lax as if every muscle in her body gave up all at once, I slowly pulled out from her.

“Need dick, now,” Anna demanded, reaching down and grabbing hold of my cock as I moved over her.

I wasn’t surprised that Anna was so horny, after all 3 weeks was quite a long time for her to go without sex. Sure, she had brought her full arsenal of sex toys with her to film, but nothing beat that human touch for either of us. And the way she was hungering for my dick only turned me on even more, if that was even possible. Therefore I had a toothy grin plastered to my face as I let her guide my cock towards her pussy. As she lined me up with her opening, I pushed forward, slowly sinking half of my cock into her tight pussy.

“Ohhhhh,” Anna moaned, hooking her legs around my waist and using them to help pull me into her until every one of my 7 inches was filling her tight pussy.

Given her tiny stature, Anna’s sntach was tight on most days despite her massive amount of sexual history, but when Anna went weeks without sex, her pussy lips gripped my cock as fierce as anything. After taking a second to relish the moment I slowly pulled back until only the head of my cock was still inside her. I paused a heartbeat with most of my dick outside her pussy, feeling the cool air against my wet member but Anna was having none of it. Digging her heels into my glutes, she pulled with her slender but strong legs until I gave in and shoved my way back into her.

I was torn between wanting to enjoy Anna’s body a little longer after several weeks without it, but we both also wanted to get to the good fucking. Therefore I sped my thrusts down into her waiting snatch by setting a more measured pace. Extending my arms I slowly slid my cock out but once again Anna tried to speed me up by arching her back to lift hips and meet my thrusts. Though she was tiny, she wanted a hard fuck most times, today included.

“Harder,” Anna said, the need etched on her face.

Just based on the 5 minutes of time Anna had gone from my front door into my bedroom, I knew that today was not about passionate lovemaking. Today was about orgasms, and in Anna’s case, getting off as many as she could. Therefore I knew right away that we weren’t going to be doing any marathon sex sessions, hell, we weren’t even gonna do a 30 minute fuck either. Today was about quickies, and multiples of them.

“Maybe I want to go slow,” I said, dropping down onto my elbows with my face mere inches from Anna’s. “You know, make love with you.”

“Harder, please?” Anna groaned as I continued to move much slower than she wanted. It was actually way slower than I wanted too, but after weeks without sex I needed to start slow instead of going in with guns blazing. “Fuck me harder, Og, harder.”

Being the sucker I was for a slender, sexy woman with big tits using dirty talk, I relented on my resistance and gave her a sharp thrust, drawing a low moan of appreciation. Pressing my chest against her pillowy boobs, I leaned my head down to kiss her. When my tongue darted out to lick her lips she opened her mouth to grant it access.

As I drove my cock down into her, Anna moaned and bucked against me, not meeting my thrust but rather grinding as I pushed in to heighten the pleasure. Her tongue battled with mine and the grip her hands had on my shoulders tightened as her need spurred me on. A series of low, guttural moans were emitted from her throat only to be muffled by my mouth as little spasms of pleasure shot through her body.

“So close, Og,” Anna cooed into my ear. “Oh, fuck me. Awhh, make me cum.”

Wanting nothing more than to watch her orgasm underneath me and for a second time in short order, I gave her short, quick thrusts. I shouldn’t have been surprised that after only a handful of minutes fucking she was ready to reach her climax again, since once Anna earned her first orgasm, the following ones were hot on the initial one’s heels. Plus the good thing was that I was far enough away from cumming that I was able to really give it to her without worrying too much about getting there before she did.

“You want to cum all over my cock, don’t you?” I hissed while I drilled into her with a steady tempo.

“Oh god, ohhhhh, uhhh huhhh,” Anna panted, her blue eyes closed as her body started to shake under me.

“I’m going to make you cum, and then I’m going to flip you over and fuck that tight little ass of yours,” I told Anna as I felt her pussy start to clench up around my still thrusting cock. “Now tell me who's the only one who gets to stick their hard cock up your ass?”

“Ohhhhh, awwhhh, uhhhhh, just youuuuu,” Anna answered, her eyes rolling back in her head. “AAWWHHHH GOOODDDD!” And with one final squeal her orgasm rocked her.

Her arms were already traced under my shoulders and as she prepared to orgasm she slapped her palms against my shoulder blades and squeezed hard while her thighs squeezed my waist tightly. Though tiny, Anna could generate a fair amount of power when she came. Anna’s face and chest flushed a deep pink as every blood vessel in her body filled. Once more I felt her pussy clamped down, only this time it was around my cock and not my fingers but I kept right on pumping in hopes of making her climax last as long as possible.

Reading her body language, I speared  inside her one final time and kept myself buried to the hilt in her wet snatch as I rode out the last of her climax. Within a handful of seconds I felt Anna begin to go limp underneath me so I made the choice to pull out of her completely. If I’d kept going I probably would’ve just gotten her halfway to her next orgasm before I came, and then left her hanging, but by pulling out it gave me a chance to rest a bit before trying to take her ass.

“Uhhh,” Anna groaned at the sudden withdrawal, but the dopey looking eyes and goofy smile on her face told me she was really in no position to complain.

Giving Anna a quick kiss I disengaged from her and shifted on the bed so I could reach out and open the drawer near my headboard. Reaching in I grabbed a small bottle of lube and pulled it out, relieved that it was still half-filled despite how often I reached for it with Anna. After giving her another quick kiss, this time she returned it with more vigor, showing signs she was returning to life. Therefore as we kissed I slipped my hands under her back and rolled her over onto her stomach. Without needing to tell her, Anna lifted her hips and got her knees underneath her before extending her arms so she was facing the headboard on all fours.

Kneeling behind Anna, I squeezed a bit of lube onto my fingers and rubbed them together to warm them up a bit before rubbing the newly slick fingers against Anna’s asshole. I had made the mistake of just putting a big dollop of lube straight from the bottle onto her asshole previously and it caused her rosebud to crinkle tighter than ever. In fact, we weren’t able to do anal that night because she tightened up too much, thus I had forever learned my lesson and warmed up the lube first.

Anna moaned as I rubbed around the perimeter of her asshole before slowly pushing against the center. Naturally, her tiny anus resisted at first but after a moment of insistent pressure, not to mention her calming herself, it gave way and my finger eased into her ass.

“Mmm,” Anna moaned as I reached my other hand forward to idly rub her clit as I worked a finger around in her asshole, stretching it out while simultaneously spreading the lube deeper into her rectum.

“You ready to get your ass fucked, or would you rather I fuck your pussy some more?” I asked Anna, pretty sure about the answer but still giving her an out if she wanted it.

“Fuck my ass, Og, fuck it hard,” Anna hissed, reaching back to pull her butt cheeks apart for me.

For some, hearing this tiny creature who only measured 5’0 tall and tipped the scales at 100lbs on a heavy day beg for hard anal sex may have been something from a teenage boy’s fantasies. But Anna was just a sexual freak who had perfected her art with the proverbial 10,000 hours. As if I hadn’t already demonstrated the power that Anna’s words had over me, I was helpless to do anything but straighten up behind her. Grabbing my cock I took a moment to smear some lube on it before aiming it at Anna’s backdoor.

Pressing the slick tip against her asshole, I felt her resist me initially but after pausing a moment she started to visibly relax. I knew better than to tell her to calm or relax, as that typically only made a woman clam up more, therefore I allowed the well-experienced celebrity to sort herself out. Pushing forward her alan sphincter finally caved and I lunged forward until head was firmly seated inside her ass.

“Oh shit,” Anna gasped, letting go of her ass. “It’s even bigger than I remember.”

“Want me to stop?” I offered, taking hold of her hips.

“Nooo,” Anna hissed, pushing back against me. “Keep going.”

Pulling on her hips, I pushed forward burying more of my cock into Anna’s ass with the paired motions. When Anna gasped again after her sphincter hit the halfway point of my dick, I paused a beat before forging onward once more. We had done this dance a number of times so I knew her limits more or less fairly well. While for some women you had to only use your tip to fuck their ass for awhile until loosened, Anna’s approach was she’d rather stretch her flexible asshole to its limit as soon as possible. Therefore it took a couple of minutes as opposed to the handful of seconds it normally was, but our efforts paid off as I felt my pelvis pressing up against the cheeks of her slender but bubbly ass.

“So big,” Anna grunted, squeezing her anus even tighter around the base of my cock.

“Keep doing that and I’m not going to last long,” I warned her, drawing a small giggle from Anna.

I left my cock to soak in the deepest section of her bowels, allowing the talented actress time to adjust to my size. I wasn’t the thickest in the world, but having anything shoved up your asshole, especially when it was nearly 7 inches deep in your rectum, required a brief spell of recovery. When I was sure she was ready, I slowly pulled back until half of my cock was outside the snug cocoon of her asshole, the mix of cool air on half my cock while the other was buried in the warm confines of Anna Kendrick’s backdoor a unique feeling. Without bothering to stop, I immediately pushed back in, albeit only slightly faster than I’d pulled out.

“More,” Anna hissed, pushing back to meet my thrust.

Pulling half of my cock out once more I paused a moment before slamming forward with enough force to make Anna gasp. The blow caused her entire body to rock forward, the firm, meaty cheeks of her ass rippling from the contact and her heavy tits swaying up towards her face, threatening to deliver a matching set of black eyes. When she didn’t object to the harder thrust, which she had been begging for, I immediately slid out and repeated it, this time causing a moan to escape her mouth.

“Fuck my ass,” Anna moaned, reaching underneath herself to rub her clit.

“You’re my little anal slut, aren’t you?” I grunted as I started to fuck her ass like she wanted.

“Yeah,” Anna answered, nodding her head as her finger stroked her pussy.

“Whose ass is this?” I asked, giving her butt a light smack.

“Ohhhhh, yours, all yours,” Anna replied, pushing back to meet my thrusts with as much, or more, enthusiasm as I was using.

As if to prove the point that this was my ass, I increased my speed, deciding to really fuck Anna Kendrick’s perfect asshole. With each successive thrust I would length my stride so while I started using only half my cock, within a dozen strokes I was plowing her rectum from the tip to the base. My plowing was smooth and even, despite the fact it was getting faster and faster, therefore watching her ass ripple with the blow of my abdomen against her had an oddly hypnotic feel.

At the pace I was sodomizing the Pitch Perfect star, I knew it wasn’t sustainable, especially after going several weeks without sex. While jerking off had helped keep the hormones at bay, nothing could replicate the feel of her velvety wet pussy and now her tight sphincter hugging around my cock. Therefore after roughly 2 minutes of this blistering pace, I slowed down to long, smooth and, most importantly, slow thrusts with the majority of my length, making sure I stayed soaking in her dumper for several heartbeats before pulling out and repeating.

This approach worked well for me, giving me a chance to catch my breath, and more importantly, check how fast my orgasm was building. The problem with Anna being in a fast anf urious fuck mood was that it was super taxing on my endurance so I was using all the tricks at my disposal to slow her down. It didn’t work all the time, but it was always worth trying.

“I’m the only one that gets to fuck your ass, eh?” I asked.

Trying to distract her with dirty talk was usually a successful technique. The slender star may look all cute and innocent, but the 34-year old was as dirty as they came. My question coincided with a change in my thrusting style as well. Where I had been doing long, slow passes into her ass with the majority of my length, this time I stopped with half my cock resting in her ass before slamming into her so hard her butt cheeks rippled from the force.

“Your ass, no one else,” Anna panted, the combination of her finger and the naughtiness of the act obviously pushing her towards climax.

Making Anna cum was always what I sought out to do, and unlike some other girlfriends, she was fairly easy to get over the edge. Much like today already, she was typically able to get off multiple orgasms before I finished. However, I always wore it like a badge of honor when I could make the tiny actress scream while sodomizing her tiny ass. Plus I knew that the more pleasure she derived from anal then the more likely we were to do it next time, which was a huge bonus for me. There was just something about seeing the entirety of my penis entering into Anna’s slender, bubbly booty that turned me on to the point of cumming on entry almost.

Feeling my own orgasm not so far off, not to mention Anna on the verge of a third, I gripped her hips and started driving into her ass even harder. From tip to base I powered into Anna, with each thrust I would use the momentum of my hips bouncing off her small but firm ass to pull back until my cock would actually fly from her asshole. The exit was only for the briefest of moments as I would immediately reverse course and slam forwards once more. Each stroke brought a grunt and a moan from Anna as the power of them pushed her forward and eventually knocked her one arm out from under her, sending her crashing to the bed on her stomach.

“Ohhhh fuck,” Anna hissed, her finger still working overtime on her clit as I put my hands on the bed and shifted my position just enough to keep fucking her with barely a missed beat.

“You’re going to cum with my cock up your ass, aren’t you?” I asked her, leaning down to press my chest against her back and whispering in her ear.

“Uhhh huhhh,” Anna whimpered, lifting her ass to meet my thrusts as best she could with me practically laying on top of her.

“Then cum while I’m fucking your ass and then I’ll pull out and cum wherever you want,” I told her as I felt her body start to tremble under me.

“Oh goooooooddddd,” Anna moaned, the tremors starting to turn into a full blown quake. “I-in muh-my mouuutthhhh. Cum in my mouth.”

No sooner had the 34-year old actress let her intentions be known of where she wanted my cum deposited, Anna screeched and her whole body shook for a third and final time this afternoon. Her asshole clenched up so tightly I had to grit my teeth and exert every last bit of self control I could muster just to pull out without busting my nut in the deepest recesses of her bowels. I had cum many times 7 inches deep in her rectum but with Anna making her demands on where my jizz was to go, I had to withstand. Even as it was I barely managed to survive the death grip, riding out the last thralls of her climax before pulling out.

Sadly, my orgasm was finally here, thus making time of the essence so I didn’t have time to stare for longer at the gaping chiasm I left of her once tight asshole. The sight of the pale round flesh transitioning to a spread red-purple ring before an inch and a half wide of blackness took over was easily enough to push me over the edge to my own orgasm. Quickly, I grabbed a hold of my dick and flew up the bed.

Luckily, though she was still going through the final throes of her massive orgasm, when she felt the bed shift under her and me lifting her chin off the bed, she somewhat came to. Her eyes were somewhat glassy and heavy lidded as she looked at me but she remembered her choice and opened her mouth nonetheless.

Sliding my cock into her mouth I pushed in until I felt the head bump against the back of her throat. Anna wasn’t in the mindset to give me another amazing blowjob, or bob her head from the way her positioning on the bed was, but I knew her limits well. Thus, as I started to fuck Anna’s mouth I felt her begin to stir enough to bob her head along with my thrusts. That was just enough stimulation to finish me over the summit of my climax and I pulled back until only the head of my cock was between her lips.

“Here it comes,” I warned Anna. Her reply was using her tongue to massage the underbelly of my cock expertly, combined with staring her gorgeous blue eyes to hold my gaze just before the first spurt erupted from the end of my cock.

Anna’s eyes widened a bit as my come splattered the roof of her mouth but after the initial shock wore off, she started to suck on my cock, eagerly slurping up my jizz as quick as my balls could pump it out. Even though I had masturbated only yesterday, I was still able to generate 5 healthy splattering of jizz, which Anna captured and swallowed gleefully. In fact, even when my well ran dry, Anna continued to suck for a almost a minute as if wanting to make sure she had indeed gotten every last drop. Though it made me shutter from how sensitive my tip was after an orgasm, who was I to tell Anna fucking Kendrick to stop sucking my cock with her talented mouth.

“Such a naughty girl sucking my cock right out of your ass,” I hissed as I let my cock slip from her mouth and sat back on the bed.

“I did?” Anna asked with a look of confusion on her face. Though a talented actress, I could tell that the Pitch Perfect star was hamming it up. “Oh my goodness, I did, didn’t I?”

“Hot, wasn’t it?” I asked her, loving each and every time the petite girl took me straight from her dirty ass directly into her mouth.

“Oh yeah,” Anna agreed, a dreamy smile crossing her face as she rolled onto her back.

“3 orgasms in 20 minutes. Might be a record for you,” I said as we both laid with heads in the pillows, recovering from the massive energy expenditure.

“Definitely up there,” Anna said before breaking into a laugh as she sat up. “Ohhh, my ass is going to be sore tonight, but it was soooo worth it.”

“Whenever it hurts you can always think about what we just did,” I told her.

“I hate to hit it and quit it, but I have to hustle downtown. Therapy session in 30...make that 20 minutes from now.” Anna stated as she slid out of bed.

“Oh cool. No problem, but maybe we can do dinner tonight? Maybe 8 at our sushi spot?” I ask her as she started to get dressed.

“I don’t know. I’m pretty full,” Anna said with a sly grin, leaning down to kiss me as she buttoned her blouse. “Get it. Because of the massive load of cum I just swallowed.”

“You know, if you have to explain the joke it loses some of its effectiveness,” I said, giving her a second, longer kiss.

“Mmm,” Anna moaned before breaking the kiss. “I really have to go and if I don’t go now I’ll be here for another hour. And while it would be a lot of fun, I should really go unpack some things or else I’ll get even crazier.”

“I have to take another shower anyway, care to join me,” I told her getting out of bed.

“Stop that,” Anna giggled, backing away from me. “I have to go and you keep tempting me into staying.”

“Suit yourself, but tonight you’re all mine,” I said, moving past her so I could grab a pair of boxers to cover my junk for the walk back to the shower.

“All yours,” Anna agreed.

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Re: Dating Anna Kendrick
« Reply #7 on: December 16, 2019, 05:48:35 PM »
You're seriously one of my favorite authors of celeb fiction and it's a blast to see you here and bringing amazing content like this with you. I just love how you write Anna and every story is nothing short of hot perfection.

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Re: Dating Anna Kendrick
« Reply #8 on: December 20, 2019, 04:35:25 PM »
Title: Dating Anna Kendrick Part 6 - Swift Payback
Author: The Chemist
Celebs: Taylor Swift
Codes:  MF, anal, oral
Disclaimer: I do not know Anna Kendrick, Blake Lively, Ryan Reynolds, or Taylor Swift. This story is an act of pure fiction, therefore didn’t happen. I make no money from this story.

Summary: Still feeling guilty about hiding her threesome with Blake Lively from Og, Anna Kendrick makes it up to her boyfriend by hooking him up with Taylor Swift.

“How was therapy, babe?” I asked as Anna Kendrick came into my apartment, giving a brief rap of the door before entering.

“Oh, you know, she didn’t have to use shock therapy yet so I’m not so fucked up that I can’t be helped,” Anna said, offering a weak smile as she threw herself down on the sofa opposite me.

“Seriously though, you okay?” I asked, noting her unusual worn-out body language.

“Can I tell you something? You can get mad if you want, but my therapist says holding it in isn’t helping and…” Anna said, starting to do her typical stammering as she got awkward. Though she continued to spew words, I more or less drowned them out, worried what I was about to hear.

“Anna...it’ll be okay. Just tell me what’s bothering you,” I said when she was done.

“Okay well, you know how early last year I was away in Toronto shooting a movie,” Anna started, continuing after I nodded my head, knowing she was referring to A Simple Favor. “Well, I sort of, kind of, fucked Blake Lively. Like, a lot.”

“Anna, why would I be upset about that?” I asked, sitting up and stroking her leg.

Though Anna looked all cute and cuddly, the girl was a straight up sex demon. It seemed that no matter how much or how regular we fucked, her appetite was just barely quenched. Don’t get me wrong, I’m not complaining. In fact, I think every guy (and probably girl though I’m only going with my personal experience) would love the fact their girlfriend was constantly horny, especially if their girlfriend was Anna fricking Kendrick.

Therefore, when we first started dating almost 2 years ago, it was a casual affair. I had learnt through conversation that she didn’t like being tied down, which I was willing to forego if it meant getting to fuck and be with her as one of her steady partners. However, after 6 months of casually dating, she came to me and more or less asked to be exclusive. Well, her version of exclusive. Which meant we could both still fuck as many girls as we wanted provided we were willing to share and we always came home to each other. It was a deal I was more than happy to make, but in the back of my mind I knew that Anna was unlikely to ever totally be tied down.

“So while most of the time it was only me and Blake fucking, one time it was with her husband as well,” Anna finally shared.

Even as she spoke the words I could see some of the weight that had been on her chest start to lessen. She had her head down but I could see her piercing blue eyes looking out the side, watching me for any reaction. While I wasn’t super happy about her sleeping with another guy, I would have also have been a big hypocrite to be pissed about it. If anything, I was a little peeved that she felt like she had to keep it from me. However, seeing how tormented she was by keeping this from me, as well as fucking another man while we were together albeit not super exclusive, made it so that the last thing I wanted to do was twist the screw.

“Anna...we’re only human. We fuck up, we make mistakes. All we can do is find someone we want to be in the foxhole with.” I explained.

I was going to say more but seeing the wave of relief wash over the normally reserved woman was enough for me. I got up and went to confront, a gesture she was more than happy to have from me. As I held her in my arms, she added a few extra details since I handled the big bombshell so well, the most notable of which was the fact that Ryan and Blake had taped the threesome, with Anna’s consent of course. Off hand she asked if I wanted her to get a copy of it and I found that I did want to see it, so she said she’d contact Blake soon.


“What’s that for?” I asked as Anna went to pull her phone out.

“Alarm. Meeting Aubrey to get ready for tonight.” Anna explained. “You still want to go to the party with me?”

“I want nothing else.”

*   *   *

“Listen, you keep hanging out here and I’m going to go grab us some drinks,” Anna said.

I nodded and watched as my stunning girlfriend in her tight-fitting costume sauntered her way to the bar. I’m happy she offered to go because being an adorable female, not to mention a celebrity, meant she would skyrocket to the front of the line, whereas I’d have waited for half an hour. However, I noticed that her course was taking her to an out-of-the-way part of the counter, closer to the VIP, meaning the tiny actress had to wade through more bodies.

I watched in curiosity now and soon realized that her course was bringing her to a collision course with the tall, radiant blonde that was demanding a lot of attention. I swore under my breath as I realized that Anna had cozied up on the bar to Taylor Swift! I know they weren’t friends, as they ran in different circles, but within seconds the two were exchanging words. In fact, by the sentence it seemed that Anna and the girl dressed as Wonder Woman were becoming more engrossed in the conversation.

After maybe another minute, the barkeep came over and took their orders. Anna and Taylor chatted for the 30 seconds it took for their drinks to be brought, at which point the tiny auburn-haired actress and leggy blonde singer said their good-byes. With a final greeting, Anna scooped up what appeared to be two whiskey sours and headed back my way.

“Why are you smiling so brightly,” I asked as Anna came back towards me, beaming. “Taylor ask you to become one of her girl squad?”

“No you dummy,” Anna said, giggling at my joke. “I’m smiling because tonight you are totally gonna fuck that goddess.”

“Wait!? What!?” I was actually I was able to get out any words.

“Not a guarantee but, I mean, she’s as close to a for sure lay after our convo,” Anna added before recapping their brief but apparently productive conversation.

*   *   *

“Oh my God, I love your costume,” Anna said. She had arrived at the bar and slowly inched her way over until she was right next to Taylor Swift. “I guess it helps having those legs to pull off the tiny booty shorts.”

“Thanks...oh! You’re Anna Kendrick! I loved you in...everything!” Taylor said, reaching down and giving the girl near crushing hug.

“You’re so sweet,” Anna said before using the line that would shift the conversation to where she wanted it to go. “Too bad you can’t use that line on C-Diddy.”

“You know Cara?” Taylor asked, referring to one of her best friends Cara Delevingne.

“Yeah. She dated my bestie Kristen Stewart for awhile. My boyfriend even took her anal v-card,” Anna said with a little laugh.

“Oh my God!” Taylor nearly snorted out her drink. “I remember Cara telling me about how some guy totally turned her into an anal loving whore. Her words.”

“Yup. That’s my guy...well not exactly just my guy,” Anna said, continuing to lay her trap for the 29 year old singer.

“You mean you aren’t dating anymore?” Taylor asked, unable to keep the note of curiosity from her tone.

“You’re dating. In fact he’s here tonight. It’s only that we aren’t exclusive. Great guy and all, and magic cock for sure, but we prefer an open relationship,” Anna described, bending the truth a little.

“Interesting. Very interesting,” Taylor replied, pondering.

“And another crazy thing about him...his cum.” Anna stated, baiting the hook further.

“What do you mean,” Taylor asked.

“Tasty. Not in a way that is unnatural or anything but even for girls with super-sensitive taste buds, his cum is at worst neutral tasting,” Anna shared. This was the truth, which was one of the reasons why Anna had him finish in her mouth so often. Less clean up and a yummy little treat.

“That is wild.” Taylor said, smile plastered on her face.

“Anyway, I should bring him his drink,” Anna said, picking up the two whiskey drinks.

“Why don’t you come join me and the squad in the VIP? I’ll tell the bouncer to admit the tiniest archaeologist and a guy with her that has a magic cock,” Taylor offered, bring a laugh from both women.

“See you soon.”

*   *   *

The rest of the night passed in a blur for me. After Anna had caught me up on everything about her conversation with Taylor, she added the fact that Taylor was currently in between boyfriends. I took that to mean she was available, but Anna went on to explain that when Taylor was dating someone, she was super loyal. However, when single like she was now, Taylor would sleep around, or as Cara Delevingne described, Taylor would totally whore out.

We went up to the VIP and hung out the rest of the night with gorgeous people and A list celebrities. It was surreal, even for someone like myself who was used to rubbing elbows with Anna Kendrick and some of her friends. However, there was just something larger than life about Taylor Swift, so I found myself getting nervous just with the idea that I could fuck her tonight.

“Just remember not to put her on a pedestal,” Anna reminded me as the night was winding down.

“I don’t think that’s a worry. She already left,” I replied, noting the lack of tall, gorgeous, blonde singers around.

“I wouldn’t be so sure about that,” Anna replied, seeing a large man in a suit headed my way.

“You Og?” the man’s deep, booming voice asked.

“Yeah,” I replied nervously.

“Ms. Swift has left a car for you to attend her at her house,” the man said.

“Told ya.” Anna said with a smile. “Now go have fun. And remember, I want every last detail.”

*   *   *

Og wouldn’t have traded Anna in for anyone, therefore he was more than happy with their arrangement for tonight. He loved Anna’s mixture of cuteness, quirkiness, personality, atypical beauty and, of course, her amazing rack. That being said, Taylor Swift was something else entirely.

Part of it had to do with her aura, how she had become larger than life while also picking up a well deserved reputation for having a healthy appreciation for sex. Not to Anna’s hardcore degree, but Taylor was known for hopping to bed to bed for a good reason. Of course, she had an amazing body to back up her sex positive attitude and worldwide reputation.

Taylor’s body had changed a lot in the last couple of years. The constant touring meant she found working out to be more paramount, and you could tell the gym work paid off. The barbell had completely blasted her glutes, added inches to her thighs in all the best ways and flattened her stomach. Combined with that, Anna had shared that her bra size had grow almost a couple to be a full B cup. Those changes were magnified by the fact she also showed a willingness to show off her amazing body more and more, whether it be in super skimpy costumes or bikini pictures on social media.

“I was beginning to wonder if you were coming or not,” Taylor said when she opened the door for me.

“Sorry about that,” I apologized though traffic was out of my control. “Great place though.”

“Thank you,” she replied, though I got the distinct impression she was sizing me up. “Can I get you a drink? You’re a whiskey man if I remember Anna correctly.”

“Good listening. I am indeed. Neat or on the rocks. I’m flexible,” I replied, knowing that if anyone was likely to have good calibre alcohol, it would be Taylor.

Taylor turned and started walking down the hallway to her right. I got the impression I should follow so I did just that. Given the way she was swaying her hips, it was clear to me she was doing that on purpose for my benefit, which I appreciated it. This was more or less confirmed when she turned her head back to look at me and gave me a toothy grin, having caught me looking at her ass.

“See something you liked,” Taylor asked in a soft, seductive tone as we entered her kitchen.

“Sorry. That was not cool of me to be checking you out like that,” I confessed.

“Nothing wrong with looking,” Taylor said as she quickly got down two glasses and filled them rather generously with whiskey.

“Cheers,” I said, raising my glass to clink with hers.

“Cheers,” she replied, touching glasses then both of us took our first sip. “So you’re an ass guy?”

“Tone of surprise?” I shot back with my own question.

“Just surprised is all,” Taylor answered. “You’re seeing Anna Kendrick for a long time now. She’s got a cute butt but her tits are obviously the showstopper on that pint-sized hottie.”

“Totally fair assessment. I think her legs are a little underrated as well,” I added, still in disbelief that I was in Taylor Swift’s kitchen for a nightcap. Remembering Anna’s words from earlier, I took another sip and tried to drown my nerves. “But yes, though Anna has tempted me with her great boobs, especially for a spinner like her, my first love has always been booties.”

“We all have our preferences,” she said with a naughty twinkle in her eye. “So how does mine stack up?”

“Your butt? Well, maybe its the whiskey talking or your straight forward approach but I’d say it receives top marks,” I replied honestly. When I saw the pleased but eager for more look on her face, I continued my assessment. “I remembered it being...smaller before from pictures but seeing it tonight...wow!”

“Oh?” Taylor asked, downing the last of her drink and starting to walk around the counter to be in front of me.

“I mean, it seems like everything on you has filled out in the best way possible. Your hips look wider to give that perfect hourglass figure. Your legs have always been a traffic stopper but now they seem thicker, more muscular and yet so feminine and sexy. Your aforementioned caboose changed from small and cute to big and tight. More muscular like your thighs.” I replied, knowing for sure it was the alcohol making my lips so loose.

“Wow! That was super descriptive.” Taylor laughed as she stood right in front of me. “A girl might get the impression you found her attractive.”

“Good...because that was the exact impression I was trying to give off.” I retorted, matching her playful banter like for like.

I saw my opening so I went for it. Reaching an arm around her tall frame so my hand could land on the back of her head in the soft curls of blonde hair, I simultaneously pulled her towards me while I leaned forward. Our lips touched with a soft smacking sound at first before we both opened our mouths and pressed our tongues against each others. The softness ended their as we greedily pressed our lips together while our tongues battled one another for supremacy.

As much as I wanted to continue the intense makeout session going with the gorgeous leggy singer, after another minute of kissing I broke it off. As good as it felt to tongue wrestle with Taylor, I had much more fun ways of spending the night with her. Standing up I put my hands on Taylor’s waist. Leaning her back against the counter I bent my knees and pressed my body against hers.

“Bedroom,” Taylor said, breaking the kiss to wave her hand in the direction of where another hallway exited the kitchen.

“Sure,” I said, lifting her up and setting her down on the counter instead.

Putting my hands on her knees I pushed them apart so I could slip between them. Leaning in to kiss the pop singer, I slid my hands up her thighs which were soft and unending until they disappeared underneath her dress. As they moved closer to her sex, Taylor spread her legs even wider to grant me more access and pressed her chest against mine.

When my hands reached the tops of Taylor’s thighs I extended my thumbs and rubbed them against the front of her panties, just above her snatch. Hooking my middle fingers in the waistband of her thong, I slowly tugged them down. Wrapping her arms around my neck, Taylor used me to help lift herself up so I could pull her panties down over her ass. If I thought she had long thighs then I was in for a treat as the thong just kept sliding down and down. Finally the tiny undergarments crested her slim calves and went over her feet, still contained in her black high heels.

“God, you’re unbelievable,” I grunted as my hands rubbed up her lengthy and smooth legs.

Standing there with her panties in my hand, I looked at Taylor with what could only be described as an evil grin. She cocked her head to the side in question, wondering what my thought process was. We both knew that from the position of a pantie-less woman sitting on a high counter with legs spread, there were a lot of possibilities. Knowing I couldn’t just stand there and smiling down at her like an idiot, only one option came to me that I knew I had to do first.

Stepping up to Taylor, I gave her a quick kiss before sinking to my knees. She moaned as I put my hands behind the backs of her knees and pulled her forward until her ass was right at the edge of the counter. Draping her flawless legs over my shoulders, I flipped the skirt of her dress up, exposing her bare pussy to my hungry gaze. I didn’t know what to expect I’d find with Taylor Swift’s pussy but I was pleased that it was shaven bald, meanwhile her pussy lips were bright pink, already glistening faintly in arousal and just looking the prettiest little snatch I’d ever seen.

“So fucking hot,” I breathed as I drank in the sight.

Once more, I remembered Anna’s warning to me of not being to awed by the mega pop star and her celebrity fame. Therefore, I decided a little teasing would be perfect and set me apart from her many other suitors. Therefore, reaching under her to grab hold of her thighs, I lightly blew a stream of air across her pussy. Taylor moaned before making a motion to grab the top of my head in response. As she tried to pull my head closer to her wanting sex, I stiffened my neck and refused to budge as I exhaled against her pussy again.

“Please?” Taylor groaned, grabbing a handful of hair to pull me closer.

I don’t know why it felt so good to make such a massive celebrity and known sex fiend like Taylor Swift beg for me to eat her out, but that didn’t change the fact that it felt pretty damn good. Therefore I finally relented by leaning in and ever so lightly ran the tip of my tongue along the length of her slit. I was pretty sure that it wasn’t what she was looking for though because she let an anguished grunt at my teasing.

“Want me to lick you?” I asked, looking up at her.

“Yes please,” Taylor begged, using her powerful legs on my shoulders and her hands in my hair to try to lift herself off the counter and get her pussy a couple inches closer to my tongue.

“Tell me what you want,” I said, using my hands on her thighs to hold her down on the counter.

“I want you to lick my pussyyyyyyyy,” Taylor moaned, her body twitching as I finally let my tongue dart out to flick at her clit.

I decided that actually making Taylor Swift beg me to eat her out was enough for me to stop delaying. Done teasing, I moved a hand between her legs to spread her pink lips with my fingers so my tongue could lightly pummel her clit with rapid but soft bats. When she started to gasp for air and her fingers in my hair threatened to rip it out at the roots, I changed tactics by moving my tongue down to slither through her folds, collecting moisture.

“Ohhhh, fuck me,” Taylor gasped, her grip on my hair tightening as she bucked her hips against my face.

Hearing the notorious good girl Taylor Swift swore kind of spun me for a loop but I quickly recovered. Moving back up to her clit, I wrapped my lips around her sensitive nub. When I gave it a suck, Taylor stiffened like she’d been shot, her hand in my hair twitching hard enough that it felt like she could’ve pulled out a whole chunk of hair.

Keeping one hand on her thigh to keep her from bucking me off, I moved the other one up to where she was trying to scalp me. I groped around until I could find and grab her hand, at which point I was able to pry her fingers loose from my hair. Giving my genetics I was unlikely to keep it all forever so I wanted to maintain it for as long as I could, though if there was a reason to lose some then Taylor Swift ripping it out while I eat out her pretty pussy would be a good reason. As her hand wrapped around mine instead I brought it to her flat stomach where I lightly pushed, urging her to lay back.

“Please keep going,” Taylor begged once more.

As if we reached a compromise, as the popstar leaned back her hands went back to my hair but the grip stayed loose enough for me to deal with. Of course, with her back against the counter it gave her leverage to buck her hips, which made it more difficult to hang on. Rather than continue to suck on her clit, I changed again and flattened my tongue against it. Bringing my right hand down between her legs, I circled the slick opening with my index finger for a few rounds before slowly pushing my digit into Taylor’s tight cunt.

“Ohhhh,” Taylor moaned, her body jerking involuntarily as I kept her on edge.

Sensing that I had megastar Taylor Swift on the ropes, close to having her cum, I went in for the kill. Holding her as still so I could use my tongue to flick at her clit once more, this time in a frenzied, rapid-fire fashion, all while my finger continued plunging the depths of her snatch. However, I figured the slender singer could do with extra thickness filling her so I added a second finger to the one in her pussy and started to pump them in and out of her.

“Oh God! Fuck, fuck,” Taylor hissed, her thighs clamping tightly against my ears as her hips started to buck.

She had strong thighs so I hoped she wouldn’t use them to pop my head like a grape. Blocking that from my mind so I could focus all my attention on keeping track of her sensitive nub in all her bucking, I curled my fingers inside her snatch. Finding her G-spot with expert ease, I stroked it with my fingertips and was rewarded with a loud scream as her whole body tightened up. Knowing I had my range, I kept my fingertips in the same spot and rapidly brought them off and back onto the sensitive spot, tapping them repeatedly.

“JESUS CHRIST! I”M CUMMING,” the singer hollered at the top of her vocal range.

As my twin efforts of finger blasting her G-spot and flicking her clit with my tongue paid massive dividends, Taylor soaked my hand with her cum. Wanting her to stay at this bliss point for as long as possible, I kept flicking my tongue against her clit to prolong her pleasure, but as her orgasm wore on her dance training came to the forefront with her muscular thighs gripping my head tightly and with each twitch it felt like she was going to snap my neck.

Between the neck-breaking thigh squeeze and bucking her hips in tune with every one of my flicks to her clit, I relented my twin assaults on her snatch. Pulling my fingers from her pussy and, after one last flick, I unlatched my lips from the top of her cunt as I put my tongue back into her mouth. After a couple moments without stimulation, Taylor finally started to calm down enough to unlock her legs from around my head so I could regain my feet.

“Oh god,” Taylor gasped as her mental faculties started to return.

“Bedroom now?” I asked. The bedroom would be more comfortable but staying here would mean I could start fucking her as soon as I dropped my pants.

“Bed for sure,” Taylor said, sitting up. As she slid off the counter she had to lean against the edge for a moment until her knees stopped wobbling.

“Bedroom, it is then,” I said, reaching out and pulling the zipper down on her dress as I followed behind her. “That was going to need to go sooner or later, so I figured sooner was better.”

“I bet,” Taylor laughed.

Between her walking and me actively trying to pull it down, Taylor got tired of having to deal with it so stopped to let me pull it down her body and leave her in nothing but her bra. Though her tight-fitting dress left little of her body to the imagination, seeing her legs and ass in the flesh was a sensational sight. Her legs really did seem to go for miles, being a perfect mix of slender in the calves and thicker in the thighs, especially before they gave way to her underrated booty. Though not in the same category as a Jennifer Lopez, Taylor’s hard work in the gym had paid off in providing herself a nice juicy ass that was tight, firm and fairly thick for her thin frame.

“Now the bra,” I said.

Before I could reach out and try to unhook it, Taylor looked over her shoulder and gave me a sultry look that got across her passion level. With a naughty smile, the leggy singer took off down the hall, making me give chase, my eyes locked on her cute ass the whole way. As we reached the door to her bedroom I finally caught up to her by way of wrapping my arms around her, clutching her slender body to me, my cock pressing against her back through my pants. Lifting her off the ground, she screamed playfully as I carried her the rest of the way to massive bed.

Still clutching her to me with my chest pressed against her back, I leaned forward until Taylor was laying on her stomach on the bed with me on top of her. Making sure her arms were pinned underneath her, I moved to straddle her waist so I was sitting on her butt, though I made sure to keep as much weight on my knees as I could instead of on her. I was far from fat, but even still I wasn’t looking to crush her, only playfully dominate the leggy blonde.

“That bra is coming off,” I said, dragging a finger along her spine as she squirmed under me.

Reaching her bra strap I deftly unhooked it with one hand while the other one set about unbuttoning my own shirt. When my shirt was undone I lifted up and rolled off of her. As she started to roll over, I grabbed a hold of her bra and pulled it down her arms, stripping the last stitch of clothing from her body long, curvy body.

“No fair, now I’m naked and you’ve still got all those clothes on,” Taylor observed.

“Then I guess we should do something about that,” I said as I took off my shirt.

“Definitely,” Taylor said, going for my belt.

Between the two of us we made short work of my clothes. When I tried to push her down onto her back though, Taylor merely smiled and slipped off the bed completely. Sinking to her knees she reached out and ran her fingertips along the shaft of my cock from tip to base and down further to my sack before wrapping her hand around the bottom of my manhood. Looking up to stare at me with her pretty green eyes, Taylor flashed me a grin before she lifted my cock until it was straight up and down. Leaning her head in, she blew a stream of air across the shaft, obviously trying to pay me back for teasing her earlier.

“Not funny,” I grunted as she smirked up at me.

“A little,” Taylor smiled before sticking out her tongue and licking the underside of my cock from base to crown.

“Better,” I said, leaning back on my hands as Taylor took the head of my cock into her mouth.

Unbelieving my luck that I could now say I’ve gotten a blowjob from both Anna Kendrick and Taylor Swift, I soaked in as much of this occasion as possible, especially since I knew Anna would want the full blow-by-blow. Swirling her tongue around the crown of my dick, Taylor slowly bobbed her head, taking a little bit more of me into her mouth at a time. When she had about half my cock in her mouth she stopped, took a breath, and reversed course until only the head was still between her lips.

“Much better,” I grunted as her tongue worked wonders on my knob.

Ignoring my comments, or maybe even inspired by them, Taylor started to push her head down but staying at the slow, sensual speed she initially started with. I didn’t mind whatsoever, in fact a slow suck from the popstar was probably preferred since it would mean my staying power would be all the better for it. When she got to the halfway point of my dick where she’d stopped last time, she kept on going, seemingly as if on a mission to take as much of me into her mouth as she could.

Feeling the head of my cock bump against the back of her throat, I thought that was it but instead Taylor kept pushing. Not surprising giving her vocal range, but Taylor tried and succeeded in relaxing her throat, thus allowing me to feel as my cock started to push even further into her mouth. Her adorable nose almost touched my pelvis but she started gagging so she used that as a cue to pull off me completely, a thick strand of saliva running from her lips to the tip of my cock.

“Glllkkk….ggaawwkkk,” Taylor sputtered.

Reaching down I brushed a lock of hair out of her face as her eyes watered, however Taylor was unaffected from her first try at deep throating me. In fact, as I stroked her cheek with my thumb and smiled at her, her hand started to beat my cock faster, using the generous amount of spit now coating it. She then stared back up at me and sucked hard, pulling the thick spit string right from my cock and into her mouth, a twinkle in her eye and a wicked grin on her lips.

Leaning back down, Taylor took me back into her mouth, but not before circling the tip of my cock with her lips and what could only be best described as making out with the head of my manhood with her eager tongue. This last a good few seconds before her face started to descend down into my lap, but this time when I bumped against the back of her throat, Taylor stopped and let her tongue caress the shaft as she worked her way back up.

“So good,” I mumbled as she expertly worked my cock.

The thickness of my dick was proving just a little too difficult for her throat to handle taking me all the way to the root, with her nose buried in my trimmed pubic patch and her chin touching my balls, but Anna had also struggle with that. Fortunately with Anna, she had enough practice at it now that my dick was a regular occupant of her gullet, and given the expert way Taylor was handling my manhood, I no doubt believed that with a little more regular fucking, she too would get to that level in no time flat.

Focusing back on the gorgeous blonde, Taylor was redoubling her efforts on her oral servicing of my manhood. The leggy singer cupped my sack and began to fondled my testicles as she increased the suction she was applying to my cock. The twin motions meant she gave up on her quest of choking down the entirety of my dick, but the attention she was giving my balls and the speed her lips moved up and down the portion of my dick in her mouth more than made up for that fact. Grunting, my head rolled back on my shoulders and my hips bucked as she seemed determined to drive me towards the edge.

“You should probably slow down,” I told the energetic popstar after another handful of minutes of her going down on me.

“You can cum and keep going?” Taylor asked, taking her mouth off me just long enough to speak. “Or are you a one and done guy?”

The question caught me off guard, as most of the time after a guy came they were out of commission. After all, it was the way our anatomy worked. However, there were times, either it be with help from a little blue pill or a cock ring, or if you were able to stay aroused intensely enough after cumming that would allow you to keep fucking. Since I got to fuck Anna whenever we wanted, I never had to try going back-to-back, at least it had been awhile. With Taylor still rhythmically sucking my suck with pleading eyes, I knew the answer she wanted to hear and I felt our combined motivations could make it happen.

“I can go multiple rounds,” I said with as much confidence I could muster.

“Good. Then I want you to cum in my mouth,” Taylor demanded before resuming her intense blowjob.

Eager to confirm Anna Kendrick’s earlier comments about Og having tasty cum, Taylor got comfortable on her knees and got to work. Shortening her bob so her mouth only worked the top two inches, her lightly held fist gripped the remaining half and stroked her hand and mouth pressed tight together and working as one. 10, 20, 30 strokes and I was able to hold out. I felt and watched as Taylor broke her lip contact with me, though her mouth and my dick were still touching via a lengthy rope of spit, as the popstar took a deep breath of air before going back in.

Taylor gave one side of my dick a sloppy lick, catching some of the dripping saliva she generously applied before giving me a full blowjob experience with all her techniques on display. 10 bobs of each technique should do it, she thought. She used her mouth and fist in unison first, then deep throated his small offering for nearly a dozen seconds. Pulling off to capture some air, Taylor beat my shaft furiously for 10 strokes then went and did 10 bobs with only her mouth. As her hand and mouth went back to suck me off together, I had to give Taylor a jittery tap on her head and neck, the international sign I was about to blow my load.

“Cum in my mouth,” she practically begged me.

Taylor went into her finishing posture, with the first thing she did was make holding eye contact with me, though I was soon screwing my eye close as the wave of pleasure washed through me. I still felt as her hand lengthened it’s stroking distance as her mouth only sucked on the tip of my cock in fast bobs, pleading for my cum. With a mighty grunt I felt the orgasm hit me like a powerhouse, before feeling Taylor only use her hand to beat me off after feeling the first blast of my cum squirt into the roof of her mouth. Circling her fist and lightly stroking me still, I emptied a good 6 or 7 streaks of cum into Taylor’s eager mouth, feeling as she used suction o felt speed my seed’s departure from my sack to her tongue. 

Her second hand had dropped between my legs in order to lightly fondling my balls as she  gulped down my cum in two swallows. Rather than pull away from me, Taylor kept her lips around my dick and slowly started to bob her head up and down once more, albeit much slower than moments before. It felt good, but my head was still so sensitive from having cum only seconds ago so it started off almost as torture, but after a minute of her blowjob it felt normal, and more importantly, I was still hard.

“Good boy,” Taylor cooed, reaching to her nightstand and taking a big gulp of some drink she had there.

The leggy singer immediately moved to straddle me, not wanting to give my dick any excuse to wilt after so recently cumming. Throwing her leg over my hips, Taylor sat down on top of me she shifted her hips, dragging her pussy along the underside of my cock and causing me to twitch, seeing as how I was still a little oversensitive from her blowjob.

Smirking at me apparently still getting even with me for the light teasing I performed before eating her out, Taylor finally got to business. Raising up on her knees, she reached down she grabbed a hold of my cock before aiming it at her hole. The leggy blonde rubbed the tip along her slit as if to let me know that she wasn’t quite done teasing me yet before finally lowering herself enough to let the head slide between her labia. She stopped with only my head just pierced inside her, maybe to make sure I wasn’t still too sensitive after my recent orgasm. I answered her by taking a hold of her narrow hips and when she started lowering herself onto me again I pulled her down while lifting my hips to drive myself all the way into her in one smooth thrust.

“Fuck,” the wholesome singer gasped, her head leaning forward and her eyes fluttering shut at the sudden penetration.

I didn’t know the last time Taylor had sex, but as we both took a moment to get used to having my cock inside her tight pussy, I couldn’t believe how snug her lips gripped me. She had a reputation for being, for lack of a better word, a slut, which Anna had confirmed earlier. However, though she was far from feeling like a virgin, she apparently had kept her pussy in excellent condition.

“God, you feel good,” I pointed out as she raised up about halfway off my cock.

Both of us were done speaking as she started to ride up and done the entire length of my shaft having properly stretched herself out. I held back from just pinning her hips steady and thrusting wildly up into her for now, letting the singer have a few minutes to work herself on me first. When she moaned and leaned forward with her hands on my chest, I took it as a good sign that letting her have control was warranted at this time.

Still leaning forward, Taylor slowly lifted up about three quarters of the way before pausing. Biting her lower lip she suddenly dropped, taking me all the way into her cunt in one swoop. Moaning she immediately rose up again, apparently having loved the feeling of taking me balls deep.

With my hands still on her hips I let my eyes rove first to her pussy where my cock was sliding in out before moving up her tight flat tummy to her breasts. Even though they were on the small side, especially compared to Anna’s pillowy large set, they still looked amazing and I made sure to spend an extra moment or two memorizing every little detail before letting my eyes continue their journey.

“So gorgeous,” I groaned, reaching around to squeeze her bubbly ass.

As Taylor started to increase the pace of her bounces on top of me I studied the way her lips quivered and curled in concentration. I let her ride me at this slow speed for a little while before I got to eager and wanted to stretch my legs, so to speak. The best part was, my dick was feeling slightly numb from cumming down Taylor’s throat minutes ago, therefore I knew I could go hard and fast \without fear of spilling my seed in the star’s womb.

Moving my hands to her back I pulled her down until her perky chest was pressed against me. As she leaned down to kiss me, I realized her breath tasted of red wine, the mystery beverage at her bedside table. Holding her ass, I gripped a surprisingly beefy cheek in each hand before pushing my hips skyward, making Taylor take the entire pole but slow...at first anyway. Digging my heels into the bed, this time when I lifted my hips and drilled up into her, I used as much power as I could.

“Ohhhh,” Taylor moaned into my mouth as I pounded into her.

I opened my eyes and made sure she wasn’t in pain from the sudden shift to aggressive thrusting, but when I saw only pleasure on her face I decided to lengthen my thrusts without slowing down. Stroking my cock in and out of her snatch, I set a tempo much faster than I would normally dare due to fear of cumming. Thus, within a handful of upwards thrusts I could both hear and feel my ball sack bouncing up and slapping the underside of Taylor Swift’s ass.

I was preparing to slow down and let the popstar catch her breath, but when she started to moan with more volume and regularity, combined with clutching at the sheets, I realized that she was closer to cumming again than I’d thought. Though I was tiring physically from the less-than-advantageous body position, I continued to give Taylor the best of my thumping thrusts upwards until my tank ran dry.

“Hold on,” I warned.

Putting a hand on her lower back, I used the other to push off the bed so I could roll over. With me now on top of Taylor, I put my hands on the bed on either side of her and straightened my arms. As her thighs gripped my waist and her heels dug into my ass I set about making the final push towards making Taylor fucking Swift cum a second time tonight. Arching my back I drove the length of my cock deep into Taylor. Before she even had a chance to moan I was pulling back. With almost the full length outside of her pussy I lunged forward slamming back in to the hilt once more, drawing a low guttural moan from Taylor.

“Fuck me,” Taylor gasped as my cock slid in and out of the velvety folds with authority.

As I drove into her we locked eyes for a moment and I could see the burning need for release again in her otherwise green eyes. Since this was our first time having sex with one another, I had no idea how Taylor liked to get off. However, when I made her cum when I ate her out earlier, it was from going deep, fast and stimulating multiple regions at the same time.

With a gameplan in place, I continued my thumping rhythm, driving my entire dick into the depth of her pussy. However, I wasn’t just using brute force because while I was balls deep inside Taylor, I tilted my hips upwards and pushed just a little deeper in order to drag the tip of my cock against her G spot, just like I did in the kitchen to make her cum hard.

“Keep going,” Taylor begged.

“Rub your clit,” I ordered in answer.

Once I saw that Taylor was reaching with her right hand to attack her clit, I shifted my weight to her left and lowered onto my elbow. With her right arm having squirmed between our bodies and her fingers eagerly rubbing her sensitive nub, I used my lower position to drive with more power while maintaining the same technique. Thrust, tilt, push, withdraw. Thrust, tilt, push, withdraw. I lived by these 4 actions until Taylor came, which given the noises being emitted by the singer would be quite soon.

“Cum with me,” Taylor encouraged, rocking her own hips now.

I was getting ready to tell the leggy singer that I wasn’t close to cumming again, but she must have been a God damn mind reader because I was practically ready to pop. In fact, with a few last thumping thrusts, not only was I winning the race, I was crossing the fucking finish line. Since she had begged me to cum with her, I assumed that she wanted me to actually unload inside her womb, despite the fact I wasn’t wearing a condom. I thought of pulling out but the thought of disappointing Taylor Swift and possibly denying her an orgasm just seemed wrong. Just as I was reaching the point where I was going to be unable to hold on any longer, Taylor arched her back and grabbed hold of my shoulders. Taking that as a sign that she was close enough for my orgasm to trigger hers, I drove forward one last time.

“Here it comes,” I grunted as I felt the cum erupt from the end of my dick.

“Oh god,” Taylor moaned, the feel of my seed spurting inside her causing her to go off as well.

As her pussy clamped down even tighter on me it squeezed rhythmically, trying to milk every last bit from my balls it could. Of course I was more than happy to let her have anything and everything I had left, which wasn’t nearly as large of a load that I unloaded into her mouth at the beginning of the night. When I’d finally emptied my balls I dropped down onto my elbows, both of us panting and gasping for air as my cock started to shrink and fell out of her.

“Wow,” Taylor said, her skin glistening both from the thin layer of sweat and the afterglow of the sex.

“Wow is right,” I sighed, rolling off of Taylor to lay on my side right next to her.

“Anna wasn’t lying when she said you had a magic cock,” Taylor shared. “And telling a cock addict like me that a guy has a dick like yours, well, I was powerless but to seduce you.”

“You’re only human,” I consoled.

“Thank you for acknowledging,” she giggled. “Anyway, shower is right through there. Your choice to stay with me tonight or I won’t be a lovesick puppy if you decide to leave.”

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