"More Than Friends" with Bailee Madison

[MiamiLyfe]

More Than Friends
Starring Bailee Madison
Codes: MF, Oral, Creampie
Written by MiamiLyfe
Disclaimer: The following is completely fictional and it is nothing but pure fantasy

  

‘When did Bailee become hot?’ Connor texted his friend while scrolling through Instagram and seeing Bailee Madison’s recent post. 

‘Where have you been the last few years,’ his friend texted back. Connor had been friends with Bailee almost since the actress moved to Los Angeles for her acting career. The Madison’s home was on the same street as Connor’s and his parents and her parents got along right away. Although he was two years older than Bailee, their parents becoming close friends resulted in the two of them hanging out a lot while growing up. As she got older he could not help but notice how cute she was, but that was all he thought of her, just as a cute female friend. 

Now it was the beginning of April in 2020, he was 22 and she was 20. He was working at a job that paid him just enough to live alone in a decent apartment in LA, and her acting career was continuing to blossom. Despite being on different paths, the two of them were still friends and would occasionally see each other at parties, plus a few times a year the two of them would do a movie night or something and hang out one-on-one. Once the global pandemic hit, LA was on lockdown. People were not allowed to go anywhere.  Connor was working from home, and he only communicated with others by text or facetime.  Things were kind of boring and he had a lot of free time to kill. And it was during that free time, he noticed that his friend wasn’t just cute, but actually extremely attractive.  He did not know what it was, but looking at her IG pictures it was like a flip had been switched and he now saw her in a whole new light. 

Over the next few months, LA stayed in lockdown.  During that time he struggled to get Bailee out of his head. Even the few times he did have a former sex buddy come over and hookup, all it took was for him to see Bailee’s latest IG post and she was back in his head. Like a song stuck in your head that just repeats over and over. He found himself masturbating to Dillion Harper (aka Bailee’s pornstar doppelganger) videos at least once a week. Throughout that time, he was still occasionally texting with Bailee just like normal, and as things started to open back up (or people just got tired of following the rules) he knew it was just a matter of time before he saw his new crush in person.  

Connor knew he did not want to date her.  They were friends, but he knew there was no way they would ever work as a couple.  As much as they got along whenever they hung out, there were just some fundamental differences between them that would tank any chance of them working out as a couple. One of the big ones being that Bailee is a good Christian girl whose faith plays a big part in her life, and he was an agnostic with borderline contempt for organized religions. That said, he wanted to fuck her in the worst way possible. He knew there was no way Bailee would just hookup with him out of the blue.  She was not the one-night-stand type, and there was no way he could convince her otherwise that the two of them hooking up was a good idea. So that’s when he came up with another idea, to seduce a bunch of her friends.  As much as guys like to talk about sex, women were even worse and they give up all the details to their close friends.  So he put together the idea of if he can score with a bunch of her friends and they all came back and talked about how good a time they had with him, maybe he’d have a chance with Bailee. 

   

If he were to tell anyone his plan, he knew people would think he was crazy.  But he knew he had a few things going for him.  The First was that he was a good-looking guy, and he’d taken some of his extra free time during the pandemic to work out.  While he was by no means fat when things shut down, he’d lost about 10 lbs and added some definition to his body. The other was that he, and the women he was going after, were all between 18-24, and had all been forced to keep to themselves for months.  Now, he was about to hang out with a bunch of people who are at the age when most sexually free and wild, and who have months of pent-up sexual frustrations in need of release.  One could not ask for a better set of circumstances. 

He turned out to be right about the circumstances being just right, as he went to he ended up bedding Bailee’s friend Tessa Brooks at a Memorial Day weekend party. Bailee was in Canada shooting a movie during the time of the party, so with her not there to distract him he was able to focus on flirting with Tessa. It turned out that he did not need to do much to get her.  Tessa had been in a dry spell during the last few months, and she was all too happy to snap the streak with Connor.  So much so, she had them sneak away to a bedroom for a quickie before heading home with him and spending the rest of the weekend making up for lost time and releasing her sexual frustrations. 

The first time he saw Bailee was in late September when Connor, Bailee, and six other friends rented out a big house by Big Bear Lake for a couple of days.  Connor made sure to take the bedroom right next to Bailee’s, where the headboard of his bed was pressed up against the shared wall.  He had been texting with Peyton List for several weeks before the trip.  She mentioned how she’d been pretty much dry the entire time she was in COVID lockdown. When she sent him a few mirror selfies of herself asking which bikini he thought she should bring, he knew he was in. Connor wanted to make sure he put on a show that Bailee would hear and remember. So he went through a friend of his and scored a few Viagra pills to make sure things lasted.  Sure enough, the first night he popped a little blue pill before taking Peyton back to his bedroom where they went at it for several hours.  He did not have to wonder if Bailee had heard the sounds of Peyton’s moans or the banging of the headboard against the wall, as the next day Bailee could not look him in the eye so embarrassed.  He was glad Peyton snuck back into his room the next night. After a day of hanging out by the lake sneaking glances at Bailee in her bikini, he needed to get off.  With Peyton on all fours on his bed, he was picturing it was the young brunette actress in his bed instead of the blonde and had to bite his tongue as he almost called out Bailee’s name as he emptied his balls into the Cobra Kai actress. 

While he knew Bailee had heard him and Peyton having sex, he could not be positive that either Peyton or Tessa had talked to Bailee about their hookups.  He knew there was one person who for sure would give up all the details about their sexual experience.  Paige Mills was Bailee’s best friend, so he made sure to bring his A-game when she came home with him after the two of them were at the same birthday party a couple of days after New Year’s.  And he sure must have done something right when Paige texted him for a booty call later that week.  While he got with Peyton, Tessa, and a few other women Bailee was friends with, he and Paige became a pretty regular thing with them hooking up at least once every two weeks.

One would think that sleeping with these other gorgeous women might do something to reduce Connor’s desire for Bailee, but they didn’t.  He still had a serious thirst for her.  At no time was that more evident than in mid-April.  It was 90°, so a friend of Connor’s threw a pool party.  Long after the sunset, the only people left at the party were Connor, his friend, Peyton, Paige, and Bailee. Maybe he did it because he had had too much to drink or maybe he did it just to see if he could get the girls to agree to do it, but Connor’s friend Jake suggested that they all go head back into the pool for a late-night skinny dip before calling it a night.  Paige quickly agreed, and Connor right after her. Peyton joined in and also agreed to participate, but Bailee was hesitant.  After some coaxing by her friends and everyone agreeing not to turn on the outdoor or pool lights, Bailee finally agreed to participate as well.  While everyone else stripped off their clothes before jumping into the pool, Bailee got in the pool first and then threw her bathing suit back up onto the deck.  

Connor tried not to be super obvious, but he was desperate to see Bailee’s nude form, and yet despite her being completely naked less than three feet away from him, he could not get a clear view.  He tried to go under the water and look, but all he could see was her silhouette without the lights.  When she would get out of the pool or was in the shallow end, the A Week Away star would keep one arm across her chest at all times.  Despite only getting to see a few glimpses of her side boob, and also getting to see her nude ass as she got out of the pool, that was still enough to make Connor harder than a lead pipe.  While no one commented on him having an erection, it didn’t go unnoticed.  If no one else, Peyton did take notice.  She swam up to him and as they were talking she began giving him a handjob under the water.  After a while, it became too much for him, but rather than head inside to take care of it, the two of them swam over to the far end of the pool where they had sex up against the side.  Peyton muffled her moans, however, all that did was not wake the neighbors as it was clear to the other three in the pool what they were doing.  After he delivered another creampie to the former Bunk’d, Connor found out that he had missed Bailee and Paige leaving while he was making waves in the pool.  Jake also informed Connor that he missed Bailee being completely exposed in the open as she put her bathing suit back on prior to leaving.

That brings us to the current day, where it is a rainy Friday in May in Los Angeles.  Connor got a text from Bailee, she was just looking to catch up and make some friendly small talk. He asked her what she was up to and she just told him how she was enjoying her downtime.  The press for her movie A Week Away had finally stopped, but she only had a couple of weeks before she’d have to do the same thing all over again before A Cinderella Story: Starstruck got its Netflix release.  When he asked her if she was doing anything that night, and Bailee said no, he asked if she wanted to come over to his place for a movie night.  Bailee agreed, and since neither was doing anything at that moment she told him she’d be over in about an hour even though it was only three in the afternoon. 

Bailee had been to his place scores of times to just hang out as just the two of them, but that was before Connor had developed his lust for her.  So he spent the next hour cleaning up his apartment, taking a quick shower, and optimistically putting on a clean set of sheets on the bed. He worked frantically, but when Bailee rang his buzzer, he did his best he could to catch his breath as act casual when he opened the door to let her in.  After she greeted him with a hug, Connor could not help but look her over as she entered his place.  Bailee was dressed casually in a white crop top, black spandex cycling shorts, and some white Chuck Taylors All-Stars. As she walked, he was disappointed that she appeared to be wearing a bra today.  One of the things that he had quite enjoyed the last year on her social media was that quite often she was braless as she danced and bounded around doing whatever. 

  

After some initial chit-chat, the two of them settled on the couch and scrolled around different streaming services trying to decide what to watch.  

“Have you ever watched Cruel Intentions?” Connor asked.

“I know it, but no I haven’t seen it. At least, not all of it.”  Bailee replied.

“It’s been on my list of movies to watch and it’s on HBO Now and leaving at that end of the month, so wanna watch that?”

“Sure.”  

The two of them settled onto the couch and watched the 1999 cult classic. Connor purposely suggested the movie, hoping that all the sexual stuff might loosen things up and break the ice with Bailee later on. Connor paid attention to the movie, but also his eyes kept shifting over to Bailee. He couldn’t help himself from checking out her legs as she kicked off her sneakers and put her feet up on the coffee table. He also noticed how she seemed to shift and squirm in her seat during the sexual parts of the movie.  With about thirty minutes left in the movie, Connor picked up his phone and ordered some pizza and cheesy breadsticks for the two of them.  Minutes after the movie came to an end, their food arrived. Connor got off the couch to get the food from the delivery person and then went to the kitchen to grab plates and more drinks. When he got back to the living room, he saw Bailee sitting there looking at him with a cheeky smile on her face.

“I found the perfect movie to watch next,” she excitedly.

“Oh yeah, what is it?”  He asked, not looking at the screen as he put everything down. 

“It’s a newer movie on Netflix that I’ve been looking forward to.”

“Oh yeah?” He said and then looked at the screen. He then turned back to Bailee. “No.”

“Why not?” she said while laughing. On the tv screen was the info page for Bailee’s Netflix movie A Week Away.

“Your movie was entertaining, but I’m not going to watch it again.”

“Fiiiiinnnnee,” Bailee replied, pretending to be disappointed.  He took a seat and took out a slice of pizza for himself as she scrolled through a bunch of different movies.  “What about…”

“No, not Legally Blonde again,” he stopped her.  “We’ve watched that enough.”

“But it’s so good,” she whined, but she then scrolled over to the next movie. “How about this?”

“Friends with Benefits? Really?”

“Have you seen it?”

“No. Have you?”

“No.”

“Then yeah, sure, play it,” he told her.  Bailee pressed play and got herself a slice of pizza before sitting back on the couch.  They both watched the movie and snacked on the pizza. Connor could not help but smile when the scene with Mila Kunis and Justin Timberlake were hanging out watching a RomCom, just the life imitating art aspect of it. Once again when the sex stuff came up on screen Bailee started shifting in her seat again.

“So is that what it’s like with you and Paige?” Bailee spoke and asked.

“What?”

“The way they are, is that what you and Paige are like?”

“No. They are obviously into each other,” Connor answered.

“And you two aren’t?”

“No. I mean, not in that way. We’re just friends.”

“...who have sex.”

“Yeah. Basically.”

“And Peyton?”

“And her too.”

Bailee was quiet for a few minutes, this time she turned to Connor as she spoke up again. “What’s been going on with you?”

“What are you talking about?” Connor asked as he picked up the remote and paused the movie.

“I mean, I’ve seen you and Peyton flirt before, and I knew Tessa thought you were cute, but like out of nowhere you’ve suddenly slept with seven of my friends.”

“They’re my friends too.”

“Only because they were my friends first,”  Bailee said, growing a little frustrated.

“Look, Bailes, this last year has been nuts.  People can’t go anywhere, people can’t meet new people. But we're all still young and still, have needs. So people turned to people they know and trust to satisfy those needs.”

“And you definitely satisfied their needs,” Bailee said under her breath before reaching for her drink.

“What was that?” Connor asked, having heard what she said but wanting to have her repeat it. 

“Nothing,” she replied shyly.

“Why does it matter?  You can’t tell me you haven’t done anything wild this entire last 14 months.”

“I...I haven’t... look it doesn’t matter.  I just, it’s been weird listening to all these stories about you with my friends. Every time you are with one of them they then tell me about it the next day,” Bailee could no longer look at Connor as she spoke, she was so embarrassed.

“Are they saying good things about me?”

“Well, yeah,” she said while blushing.

“Good.”

“Good?”

“Yeah, good.  I glad that they keep telling you how much they’ve enjoyed having sex with me,” Connor admitted.

“Why?”

“Because, while I did enjoy it, the whole point of me having sex with your friends was because I hoping they would give you all the details about it afterward.”

  

“What? Why? That makes no sense. Why would you…” Bailee was flummoxed by what Connor had just confessed. And she was even more taken off guard when he made his move, cutting her off by planting a kiss on her.  Bailee could not even move when she first felt his lips pressing against hers.  She remained frozen as he moved his hand behind her head and continued to kiss her.  Slowly though, her defenses started to crumble and she started kissing him back.  She did find Connor attractive, and the more she heard friends retell their stories about being with him, then the more titillated she’d been with each story.  Next thing Bailee knew she had her back against the armrest of the couch, her hands wrapped around Connor’s back, and her tongue intertwined with Connor’s as they were making out.  She continued to kiss him, but after a little bit, she started to get into her head again and think about what she was doing. Finally, she pulled her mouth away from Connor, and he just moved on to kissing the side of her face down to her neck.

“Wait, Connor, wait,” she said, “I’m not sure we should be doing this.”

Disappointed, Connor stopped kissing her and asked, “Why not?”

“I just… look, I don’t think us dating or getting in a relationship is a good idea,” She tried to explain.

“Yeah, neither do I.  We’d suck as an actual couple.”

“But then why?”

“Bailee, I can’t explain it.  But like a switch went off in my head at the beginning of the pandemic and I have been lusting for you, hard, ever since.”

“Thanks, I think, but I don’t know if we should be doing this.  We’re friends and I don’t want to ruin that.”

“Neither do I.  I want to still be friends, just with some...well, benefits.  It’s no different than me and Tessa, or Paige, or Peyton.”

“And that’s another thing, I don’t wanna just be another girl on your list.”

“Do you want me to text them right now and say we’re done? Cause I’ll do it,” Connor reached for his phone on the coffee table, “I’ll do it right now, no problem.”

“No,” she said, pulling his arm back. “You don’t need to do that. I just...I just don’t do one-night stands.  That’s just not who I am,” She explained.

Connor just looked at Bailee for a few beats, and then said “Who the fuck said anything about his being a one-night thing?”  He then bent down and kissed Bailee with as much lust and passion as he had in him.  Bailee found herself kissing him right back. Once again Bailee found herself on her back on the couch with her arms wrapped around Connor as they made out.  As they kept going, he slid one of his hands up Bailee’s shirt and cupped her bra encased tit. They both let out a moan as he squeezed it for the first time. Having her breast in his hand was the final thing needed to push Connor from having a chubby to having a full-on hard-on in his pants.  Bailee could also not deny her arousal level.  Even if part of her brain knew this might be a bad idea, her body was betraying her as she wrapped one of her legs around Connor and could now feel what was in his pants pressing against her other thigh. 

As much as he was loving feeling up her soft full breasts, he knew it was time to take things to the next level.  He gave her breast one last final squeeze and ran his thumb over her nipple which he could feel pressing up through her bra. He then moved his hand down her chest and stomach, stopping at the waistband of her shorts.  His fingers traced back and forth along where her waistband met her stomach, and then he pushed his hand down under her shorts and her panties. He could feel a tuft of hair, and then as he moved his hand down further her found the pot of gold he was looking for. He could feel her pussy.  He could feel her smooth lips, which were already nice and moist before he even had done anything. Knowing what he was about to do next, he pulled his lips away from Bailee and moved over to begin kissing her collarbone.  After a few kisses, he made his move.  Pressing his thumb to her clit, he then pushed his middle finger inside her pussy.  As a teen, Connor had been told by several people that he had the hands of a surgeon or a pianist, and while he did not become either of those things he had found a use for his long fingers.  

“Ahhhhh” Bailee moaned as she felt her friend slid his finger inside of her. Connor almost came in his pants at that moment.  After lusting over her for so long, feeling the inside of her pussy and listening to her let out a moan right into his ear was incredible. He continued to finger her and kiss along her collarbone and neck.  Bailee was now just lying back and enjoying the feeling of her pleasuring her.  What defenses she had when he first kissed her were almost completely gone.  But her hesitancy popped one last time and made one last stand as she felt him start to up the pace of his fingering. 

“Stop, stop, stop. Wait,” she said, and Connor did what she asked by stopping his movements, though he did not withdraw his finger.  “Are you sure we should be doing this?”

“I don’t think that there is anything in the world I have ever wanted to do more,” he told her.  “But if you are still not sure, just give me two minutes to do something.”

“Do what?” she said, a little bit nervous.

“You’ll see.  But I promise you I won’t fuck you without your permission, and all my clothes and your shirt will stay completely on,” he promised.

Bailee thought about it for a few seconds, but she did agree to trust him.  He got off of her and climbed to the far end of the couch. Taking his finger that was just inside the Netflix actress, he put it in his mouth and sucked it clean.  When he was done, he then reached out, grabbed her cycling shorts and underwear, and began pulling them down.  

“I thought you said my clothes were going to stay on?” she said both surprised and confused by his actions.  

“I said your shirt would stay on.  Just trust me.” He told her as he continued to pull her shorts down. He could have pulled them all the way off, but he was just too excited. Instead, as soon as they were around her calves, he lunged forward.  He would have liked to have been more seductive, more romantic. Taking his time and slowly working his lips up her well-sculpted legs before finally placing his lips over her honeypot and tasting her sweet nectar straight from the source.  But instead, he just kissed the inside of her upper thighs a few times before plunging his face forward.  Planting his face between her thighs like he was competing in a pie-eating contest. 

   

“Oh! Oh wow!” Bailee moaned as her friend went down on her. She reached behind her head and held onto the armrest. With him between her legs and on top of the shorts that were around her legs, he had basically pinned her legs down. Any time she either voluntarily or involuntarily tried to move her legs, all it did was rub her pussy even more against his face.  Connor used his tongue to give hard long licks along her lips and also to dart in and out, basically fucking her with his tongue, but while driven by pure lust he had enough control to only touch her clit sparingly.  He had dreamed about making Bailee cum so hard while eating her out that it was like he had been hit in the face with a water balloon.  But while he would like to make that dream a reality, right now was not the time.  Right now was the time to tease Bailee, get her edging. Have her moan in pleasure, but only so much pleasure.  He wanted to push her to the edge and keep her there until she couldn’t take it anymore and finally was begging him to…

“Fuck me! UUGGGhhhhh Connor please!!!!” Bailee called out.

“What did you say?” he asked excitedly as he pulled his face out from between her legs and looked her in the eyes.

“I want you to do it.  To do me.  Please, I want it so bad right now,” she pleaded. Connor just pushed his shorts down to his thighs. Once his hard dick was out in the open he moved up and kissed Bailee.  His mouth was covered in her juices, and she could taste herself as he kissed her but that didn’t stop anything. He moved his hand to the side of her face and was looking her right in the eyes as he pushed his hips forward. His cockhead brushed up against her slippery holds, and then he watched her eyes light up as he entered her.

“Oh wow,” She said when he got his full length inside of her. Once he did, he did not move.  He bent down and kissed her and just enjoyed the feeling of having his dick fully encased inside the woman he’d been lusting over for over a year. 

“Holy shit, Bailes,” he said when he started moving his hips.  Her tight pussy continuously squeezing on his cock “You have no idea how many times I’ve thought about this, but fuck, you feel better than I ever could have imagined.”

“You feel so good too,” she moaned.

“Take off your shirt,” he said in between breaths as he started to work faster. “Please, let me see your tits. I gotta see ‘em.”  Bailee just nodded and the two of them worked in tandem to remove her crop top and bra.  Once they were free and in the open, Connor dramatically reduced the speed of his humping.  He was just looking down, taking in the sight of the topless Bailee Madison below him. He salivated at the sight of her dark pinkish brown colored nipples which stood out against the backdrop of her milky white skin. Like magnets, his face drawn down to them.  Taking her nipple into her mouth while his hand worked her other breasts.  As he played with her breasts, his hips now worked at triple speed.  He was no longer thinking about what he was doing. So driven by lust his mind had gone blank and he was just reacting out of primal urges. 

“Oh wow, Connor,” Bailee moaned. With her begging for him to fuck her before, now that he was, she was on sensory overload.  She could feel her whole body start to clench up. Her nails dug into the couch and her toes began to curl. “Connor, Connor, I...I…” He moved off her breast and looked up at Bailee.  He could see her eyes were wide and her mouth was struggling to form whatever words she was trying to say.  Finally, she just opened her mouth and she squeezed her eyes shut as she let out a loud moan. Her body jerked and pussy clamped down on her friend’s dick. Connor had just been barely holding it together himself, and watching and feeling Bailee being driven to climax was just too much for him.  He was able to pull out just in time and began firing off his seed all over her stomach.  It’s only been two weeks since he had sex, but this orgasm felt so good that it was like he hadn’t had sex in years. Just a release of a whole lot of sexual frustrations and lust. They’d probably not even been having intercourse for five minutes, and yet he’d take the last five minutes of any experience he’d had in the last 14 months. 

After they both caught their breaths, Connor got off of the couch and took off his clothes.  As Bailee watched him, she also kicked her shorts and underwear the remaining way off. Now stripped nude and standing next to the couch, Connor got his first full view of Bailee’s whole naked form.  

“So how did that compare to the stories you had been told?” Connor asked, as his eyes kept sweeping back and forth along her body, basically scanning every centimeter of her body into his memory. From her chestnut color hair to her beautiful face down to her lovely breasts with her darkened nipples, which were jiggling as she leaned his see off her stomach.  His eves continued to travel down her flat stomach, to the upside-down triangle patch of dark pubic hair which pointed at her lovely womanhood, and then all the way down her shapely legs, before moving back up. 

“I’m not going to tell you that,” Bailee told him.  Her eyes then drifted downward.  With him standing next to the couch, his cock was not pointing at her at eye level. If it had softened at all when he came, it was only a negligible amount.  “I will admit that they did say you had a nice looking thing, and they weren’t wrong.”

“My thing? Bailee were both naked and just had sex, and you call it my thing?” Connor laughed.

“Fine your cock.  You have a very nice-looking cock,” she said laughing but also obviously embarrassed by the words coming out of her mouth.  Also contributing to her laughter was the fact that hearing Bailee say the word ‘cock’ caused his dick to jump. When she was done laughing, she looked up once again, reached over, and took hold of his dick.  “I can’t believe you’re still this hard.”

“Seriously? Look at you. How can I not be?”

“Blake would usually get soft though after we had sex, and it’d take him a little while to want to go again.” Bailee slowly stroked him as she spoke, but looked him in the eyes the entire time. 

“Well, I can certainly go again whenever you want.  I just hope I’ll be able to go a little bit longer the next time.”

“That does sound good,” Bailee said.  She continued to stroke his dick as the two of them went silent, both of them just looking at each other. Connor watched as her eyes started to flicker back and forth between his face and his dick.  He watched as she moved closer to his dick, and then did it again.  Connor then took a half step forward, leaving his dick an inch from her face.  As much as he wanted it, he was going to make it her decision on whether or not to go the final inch forward.  Bailee looked up, her brown eyes staring directly into his as she scooted forward a bit more and stuck out her tongue.  She licked his tip just barely touching the opening, and then she gave it another lick, swapping her tongue over the full tip, and then she opened her mouth and wrapped her lips around his dick.  

She seemed a little unsure of herself as she slowly began to suck his cock.  But after Connor peppered her with a few words of encouragement on how much he loved what she was doing to him, Bailee began to gain her confidence.  The former Good Witch actress could only take a few inches into her mouth before her gag reflex kicked in.  But using her spit she made his pole nice and slick for her hands to pump it.  While she bobbed her head a bit for what she could fit down her mouth, she paid extra attention to the tip.  Swirling her tongue and also sucking on the head. Bailee laid on her side sucking his cock as Connor stood in front of her enjoying the feeling of her lips and especially loving when her brown eyes looked up at him.  When Bailee took his member out of her mouth so she could catch her breath, Connor thought that that would be the best time to speak up. 

“We should move this to the bedroom,” he suggested. 

“Alright,” Bailee agreed. Connor helped her up and she moved to head down the hallway, but Connor waited a few seconds.  When she realized that he wasn’t right behind her, she looked over her shoulder back to him.  “What are you doing?”

“Just enjoying the view,” he said as he got a chance to see her ass in the light for the first time. Bailee giggled, and continued to walk towards the bedroom.  He watched her ass move as she continued for a few more steps.  He then moved quickly after her, and when he was only a step behind her he reached out and squeezed her ass.  She gave a surprised squeal when he felt her pinched her cheek, and another one when he scooped her up and carried her to his bed. 

Connor plopped her on the bed and jumped on himself. He grabbed hold of her and the two of them rolled around on the bed making out for several minutes.  Their mouths stayed interconnected, but their hands were all over each other.  Rubbing, groping, squeezing, and feeling up each other, touching every part of the other’s body.  When they finally stopped moving around on the bed, Bailee was on her knees bent over the top of Connor’s body, who was laying on his back.  His cock was pointing towards the ceiling but Bailee was so caught up with their kissing that she was not thinking about getting on it.  However, Connor was very aware of where his dick was and where he wanted it to be. He moved his hips around a bit, feeling for his goal.  When he felt his dick swipe against her wet opening, He focused on that spot. Bailee moaned as he rubbed his dick up and down her slit.  When he knew he had his target, he thrust his hips up and pierced her snatch.  Bailee let out a soft moan into his mouth when he first thrust into her. She pulled away and then threw her head back as she let out an even louder moan when he pulled down her hips to completely sheath his sword inside of her.  Bailee kept her head back and arched her back as he began thrusting up into her.  Connor salivated as he was looking up at Bailee arching her back with her soft pillowy breast pushed forward.  

“Bailes, ride me,” he told her.

“What?” she asked looking back down at her friend below her.  

“Take over and ride me,” he repeated himself as he stopped moving his hips upward into her.  When he stopped moving and laid flat on the bed she then understood what he was asking, and she sank her hips down on his cock.  He let Bailee rock her body on his cock and build up a rhythm. Once she seemed to build a comfortable tempo, he attacked.  It took all his willpower to not act before he did, despite how tempted he was with watching her tits sway and bounce just above his face.  Now, with Bailee taking over the heavy lifting, he was able to sit up, and once again he took one of her breasts into one of his hands, while the other he gave a soft teasing bit down on her hard nipple. 

The two of them went at it like that for a while. Connor was happy that even though he wasn’t timing it, it seemed like he’d already lasted longer than he did in the first round and still felt like he had a lot of life left in him.  Bailee continued to bounce on his dick, but she was now hunched over.  Her hand holding onto Connor’s shoulder and her boobs smothering his face. With her naughty pillows pressing against his face, he was no longer feeling them up with his hands.  Now his hands were reaching around her body and was kneading her ass cheeks like a baker with some dough. 

“Let me take over,” he told Bailee as she began to slow things down.  Bailee dismounted him and laid down on her back next to him. “Nuh-uh, rollover,” he told her.  Bailee rolled over and started to get up on her hands and knees when Connor stopped her again and told her to just lay down flat.

“What are you doing?” she turned her head and asked as she followed his instructions. 

“Just trust me,” he replied as he took one of the large pillows and then placed it under Bailee’s waist so that it lifted her hips a bit. She watched as he moved in position behind her, and bit her lip in anticipation of what was about to happen.  She buried her face in the pillows in front of her and let out a cry as Connor thrust his hips down and speared her snatch. He had his hands laid out in front of him on either side of Bailee while he continually dropped his cock down into her.  

“Oh my god, yes!” Bailee moaned as her childhood friend pounded into her prone bone style on the bed.  “Ughhhaaahhhh,”

“Tell me when you're close,” he whispered into her ear before he nibbled a bit on her earlobe.  When she did not acknowledge what he said, he repeated himself, “Bailee, tell me when you’re close to cumming.”  This time she acknowledged him and agreed to do it.  They kept fucking a bit longer, and as they did Bailee let out a few more ‘oh Gods’ and “God yeses’. Connor was loving hearing those words from her.  Causing this good Christian girl to cry out the lord’s name in absolute pleasure was an absolute thrill and turn on for him.

“Oh my God Connor...I’m almost there...I’m so close...keep going,” Bailee moaned, giving him the heads up that he asked for.  As soon as she said it, he pulled out and got off of her.  “What are you doing?” she complained.

“Fulfilling a dream,” he said as he spread her legs a bit wider and went muff diving between them.  Her disappointment in him pulling out was quickly replaced by the pleasure being delivered by her tongue. Connor furiously at her out determined to push her over the edge and get her to pop.  He used his thumb to strum against her clit as his tongue lapped away at her pussy.  He wasn’t quite sure if he had made her squirt or not, but he did know that he was soaking wet with her wetness after she came.  A wave of her juices splashed up against his face just like he had dreamed about.  

After her orgasm had died down, Bailee rolled over onto her back as Connor cleaned off his face a bit. 

“Wow,” she said breathlessly.

“Did you enjoy that?” he asked confidently.

“It wasn’t half bad,” she teased him in reply.

“Well, we’re not quite done yet he said as he spread her legs wide and tapped his still hard-as-steel pole on her twat.  He picked up one of her legs and gave her calf a few kisses before placing it on his shoulder.  Bailee wrapped her other leg around his ass after he wedged his cock back into her tight pissy.  He went back to banging Bailee but he knew he did not have much left in him, at least not for this round.  After everything they had just down and now looking down at her beautiful blissful face looking up at her and seeing her breasts ripple with each bump of his hips, he was only able to go for a few more minutes.  “Please tell me you’re on birth control.”

“Uh-huh, yes Connor,” she answered.  She knew why he was asking and what he wanted to know. “Go ahead,” she said, giving him her approval.

“Say it again,” he told her.  He really could not believe she’d given him the okay she did.  

“It’s okay Connor, cum in me.  I want it,” She told him. “Cum for me Connor.”  And that was all he needed. Hearing the girl he’d been pining over ask for him to cum inside her was enough to push him over the edge.  He pushed hard into her one last time as his cock began exploding like Mount Vesuvius.

“Oh Gawd, ugghhhh,” he groaned as he felt his balls empty out 

“OH WOW! I can feel it, I can feel you,” Bailee cried out as her body shuttered in pleasure while feeling him filling up her insides with his seed. 

While he could not prove that his second load of the night was larger than his first, he could see his jizz start to leak out from between her lower lips as soon as he pulled out. He moved next to her and the two of them cuddled on the moist sheets as they rested. They were both on their backs, but he had his arm wrapped behind her and she moved as close to him as she could. They rested for a bit, Connor though just kept replaying everything that had happened that evening in his head. He could not believe his insane plan had actually worked. He also still was not sure what caused him to suddenly see Bailee in a different light, but he thanked God for whatever the cause was. 

“So did you get whatever lust you had for me out of your system?” She asked me.

“Not even close,” he informed her.  “In fact what are you doing the rest of this weekend?”

“Not sure. I didn’t have anything planned,” she replied as she rolled onto her side.

“Good, because I want you to stay here the rest of the weekend.  The only catch is you are not allowed to put on any clothing at all until you leave.”

Bailee smiled and put her hand on his chest. Her fingers slowly dancing their way down his body. “That sounds like a fun plan,” she said as her hand wrapped around his dick.  “I would ask if you think you can handle that, but after listening to you and Peyton go at it until sunup last summer…” her voice trailed off as she began stroking his shaft.

“I can handle it, but I should confess that I popped a Viagra that night. I wanted to make sure to put on a special show with you listening on the other side of the wall. Though, I don’t see me needing any help from a pill with you around.”

“That’s sweet,” she said as she continued to slowly stroke him back to full mass.  Her eyes moved from his face down to his dick where they lingered for a bit before moving back up.  “Though, a whole weekend is a long time.  Any chance you have any extra pills just in case?”

Connor laughed, “Yeah, I do, actually.” Bailee’s eyes lit up for a moment when he told her that, but before she could say anything else he pressed his lips back against hers and rolled over so that he was once again, but far from the last time that weekend, lying on top of a naked Bailee Madison.