Lucky Bastard Revisited: Still Getting LuckyStarring Hailee Steinfeld, Bailee Madison, Victoria Justice, and Olivia HoltCodes: MF, MFF, Oral, Anal, Creampie
Written by MiamiLyfe
Disclaimer: The following is completely fictional and it is nothing but pure fantasy
NOTE: This is my 100th story (if you include separate chapters), so rather than do just some random story, I knew I had to include one specific celebrity. And I thought it might be a good time, if I was ever going to do it, to dip back into my Lucky Bastard series. And when I was thinking of casting outside of Hailee, I thought it best to bring back 3 regulars who are also my 2-4 celebrity crushes.
“Yes! Yes! Oh wow, I’ve missed this!” Bailee said as she rode my cock in the Toronto hotel room. “I’ve missed your dick. So good,” she continued as she bounced on me. Her soft breasts shook with each movement of her hips. I reached up to squeeze her breasts and she then bent down. Bailee was about to kiss my lips but turned at the last moment and gave a few kisses along my jawline. I kissed her collarbone before moving down to her tit and sucked on her nipple. My hand then slipped down from her other breast and moved down between her legs. As she continued to rock up and down my manhood, my fingers moved to the top of her vagina to her clit. I knew just how to press her little love button as we fucked.
“Oh wow, yes! Keep going…just like that,” she said as she moved her body. She began to move faster and I speed up my finger action on clit. Within two more minutes, her eyes rolled back and her body severed as she was overtaken by her orgasm. I kept brushing against her clit even as she was climaxing, causing it to build into a bigger orgasm. “Aahhhhhh, yes,” she sighed as she came down from her high. Bailee admitted, “It’s been a while since I’ve cum like that.”
“Really? Well, good news then, ‘cause we’re not done yet,” I told her. Bailee smiled broadly at that comment and even let out a small squeal of excitement. She then got off of me and I had her lay down on her stomach across the bed. Her head was facing one of the nightstands while I was getting behind her near the edge of the bed. While most of the time prone was not one of my favorite positions it always had been whenever I got with Bailee in the past. Moving on my knees behind her, I slapped my dick down onto her ass cheek. First slapping it down a few times on the right, and then a few times on the left. Then a rubbed the length of my cock between her ass crack. Bailee even pushed her ass up towards me as I more or less fucked her crack.
“Please stop teasing and put it in me already,” Bailee pleaded.
“You might want to be more specific when saying something like that considering where my dick is right now.”
Bailee then looked back over her shoulder at me and said, “You wouldn’t dare.” Her tone made it sound more like she was challenging me than she was telling me not to. An idea flashed into my mind, but that thought was interrupted.
“Just put it in her already! She’s desperate for it.” said the female voice. Looking up at the nightstand in front of Bailee, there was my wife, Hailee Steinfeld’s face on the laptop, watching what her friend and I were doing on the bed.
Hailee and I had been married for over three years at this point, and I could count on one hand the number of times I had been inside of women who weren’t Hailee since our engagement party, and each of those previous times Hailee had been in the room when it happened. The last time it happened was on the 5th of July the previous summer. Hailee and I threw a Fourth of July party at our place, and we went all out that day and night, and the next morning I woke up in bed sleeping on my back with a naked Hailee on one side of me and a naked Victoria Justice on the other. Through the fog of my hangover, memories of the previous night began to flash in my mind. Late at night, five or six people all jumped into the pool, including Hailee, VJ, and myself. Then It was only the three of us in the hot tub, and we began playing truth or dare. Dares quickly turned to the removal of clothing. Then Hailee dared Victoria to blow me. Victoria dared Hailee to have me creampie her. I dared Tori to eat my load out of Hailee. Then I remembered looking at Victoria, standing straight-legged, bent at the waist eating out my wife who was up on the edge of the hot tub. Tori’s ass was facing me and her legs were separated enough that I could clearly see her pussy lips as well. Before I could remember anything else that happened, my attention was snapped back to the present in the bedroom when I felt the hand on my cock. Looking to the side, I saw a very awake VJ looking back at me. We talked a bit and I asked her how much of the previous night. She told me not much but considering the three of us were in bed naked and how she could practically still feel my cock inside of her, she had a pretty good idea from the context clues. Victoria then ducked under the covers and the next thing I felt was her warm wet mouth go to work on my cock.
As the “Perfect Pairing” actress displayed her oral talents on me, I turned my attention to the other gorgeous brunette in my bed. With her cuddled up with her back towards me, I began kissing her bare shoulder, moving her hair out of the way, I moved towards the back of her neck until Hailee finally spun over. She muttered something unintelligible while still in the haze between being away and being asleep still. As she slowly woke up, I kissed her along the collarbone and lightly played with one of her nipples. I knew she was finally fully awake when she pulled my face to hers and kissed me. We kissed back and forth for a bit, and when we stopped she asked me what happened the previous night. My response was to simply lift the covers so she could see VJ’s eyes looking back up at us while the Victoious had half my cock stuffed into her mouth. Hailee quickly got the idea of what happened. Hailee let Tori continue her work, and the “Coast” singer went back to making out with me. I moved my hand down and began fingering her as we kissed. The three of us continued like that until l was getting close to cumming. I was set to blow my load down Viictoria’s throat and she seemed prepared to have me do it, but Hailee stopped everything. She had VJ get up and move, and Hailee then mounted me. Hailee said while she is willing to share occasionally, my cock was still hers and she then rode me until I painted the insides of her vaginal walls with my cum.
That was about eight months ago back in LA. Now it is March and I am in Toronto where a limited series I am producing is filing. Hailee too was busy with her career as well. The two of us had only been in the same city for five nights out of the last seven weeks, though we spoke daily. Earlier in the day I had been speaking with Hailee on the phone as I got back to the hotel I was staying at. We were talking about our day, and I told her about how I met Bailee Madison for lunch. She was in Toronto filming the last season of Pretty Little Liars, and while Bailee and I had not fooled around since our engagement party, we were still friends. As we talked about my lunch, Hailee became oddly giggly, and as I entered my room I found out why. There, waiting for me on my bed, was Bailee. Dressed in a matching set of black bra and panties, next to her was a freshly open 12-pack box of condoms that she had brought with her. I went silent for a minute on the phone, and Hailee asked if I liked the surprise she had delivered to my room. I questioned her if she had really set it up, and she asked me how else did I think that Bailee got a key to my room. Hailee’s three stipulations for this were that I was not allowed to creampie her pussy, Bailee was not allowed to sleep over afterward, and the final one was that Hailee wanted to watch. So I set up my laptop on the nightstand with a good view of the bed.
So now here I was on a hotel bed, fucking my wife’s friend in a prone position while her face was pointed right at a screen with my wife watching, and who I could tell based on her shoulder movement was playing with herself off camera. Bailee moaned as I held her ass and thrust down into her.
“Ugghhh, I’ve missed this,” Bailee grunted. Had I not been looking up at the laptop screen at Hailee’s face, I might have slipped and said “Me too.” While I would never ditch Hailee for Bailee, I could not deny the fact that I had always found hooking up with Bailee to be quite enjoyable. And despite the years since we’d been together, sex had not become any less enjoyable.
As we did it prone, my hands firmly gripped her ass. As we kept going, and I looked down at what was in front of me, my thoughts began to go back to the last time Bailee and I were together. As my thoughts lingered, I angled my hands differently and found my thumb moving down into her crack.
“What are you doing?” The Pretty Little Liars Original Sin actress asked as she felt my thumb begin to wonder.
“Nothing, don’t worry about it,” I told her. “Let me ask you since our last time together, have you ever tried anal again?”
“Mmmm, yes I have. But Blake didn’t like it so we’ve only done it twice.”
“All that time he’s and you and him have only done it once more time than you and I have, huh?”
“Yes,” Bailee moaned, my thumb was now rubbing up and down her backdoor as we continued to fuck hard.
“Maybe we should even up the score?”
“You won’t,” Bailee said while looking at me over her shoulder.
“Do it,” Hailee said with a devilish smirk through the screen.
With my cock slick from Bailee’s overly wet pussy, I pulled out and placed my cock head up against her rear entrance. I stayed there for a bit. I looked at Bailee, and she looked eyes with me but said nothing. I gave a little bit of pressure and she continued to not say anything. I took the knowing silence as consent. I pushed forward and Baiilee’s legs kicked up in the air as she let out a groan. I tried to go slow and let her get used to it. After it seemed like she was comfortable, I slowly began sliding back and forth.
“God, you’re just as tight as I remember,” I said to Bailee as I fucked her ass.
“Well, you’re thicker than I remember.”
“Want me to stop?”
“I didn’t say that,” Bailee answered. That also let me know that she was starting to feel good and that I could start to go harder. So I did. I started going faster and harder. Baiilee started to moan louder and grip the bed harder.
“Damn, Bailee, you really seem to be liking this. Your boyfriend won’t do it?”
“No, he won’t.”
“Too bad, he doesn’t know what he is missing,” I told her.
“Maybe I’ll ask Hailee if I can borrow you more. My boyfriend can have my pussy, but you can have my ass.” I rechecked what Hailee was up to and if she had any issues with where our dirty talk was heading. She didn’t seem to care too much since her eyes were closed, her head tilted back and her shoulder was moving. With her busy pleasuring herself while listening to us, I continued.
“Ummm, I like the sound of that. Who’s ass it this?” I asked while slapping her butt cheek.
“It’s yours!”
“Who does your ass belong to?” I asked with another spank.
“To you!”
“And I can have it whenever I want, can’t I?”
“Yes! Wherever, whenever, it’s yours!” Bailee cried out. Her voice was strained and desperate, I knew she was close. Slowing down the tempo, I pulled Bailee up to her knees and reached under her. I then began rubbing her clit with my hand as I pumped my cock in and out of her backside. We kept that going for a bit, but it wasn’t until I pushed two fingers inside of her pussy that Bailee finally surrendered to her orgasm and her pussy gushed to the point that she soaked the hand that I was fingering her with. As Bailee’s orgasmic cries began dying down, I could hear some more moans coming from my laptop, and when I looked up I could see Hailee’s eyes were closed and her body seemed to be shuttering. With Bailee cumming as I fucked her ass and then seeing Haiilee have her own orgasm, I was now pushed to the edge myself. I thought about pulling out and taking off the condom and cumming all over Bailee’s butt and back, but with us putting on a show for Hailee and Bailee’s face still right in front of the camera, I had another idea.
Pulling my cock out of Bailee’s ass, I then jumped up and went to the other side of the bed. I shed the condom and threw it to the floor. Taking Baiilee by surprise I flipped her onto her back, and now when the brunette actress opened her eyes she was looking at me upside down as I stood in front of her with my stiff pole pointed right at her.
“Give it to me,” was her only reply to the new situation. I stroked my cock and Bailee’s hand went to her breasts and played with them as she patiently waited for me to glaze her face like a toaster strudel. It did not take me long to deliver what we were both waiting for. With a grunt, my cock erupted. My initial two blasts were so strong they went long and landed on her chest, but after that, I took better aim and began covering Bailee’s pretty face with my hot load. It had been a few days since I had taken care of myself and it showed with the amount of cum that shot out and sprayed Bailee. When I started slowing down, Bailee lurched forward and took my cockhead into her mouth and sucked my cock like a straw, slurping whatever was left out of me. When I was finally done, Bailee let my cock, slip from her lips and she gave me a big huge smile while her face was drenched in my jizz. I thought about going to get my phone to take a picture, but I got beaten to the punch.
“Now, there’s a picture,” Hailee said. That comment was followed up by the sound of a camera shutter.
“Did you just take a screenshot?” Bailee asked her friend.
“Maybe,” Hailee coyly replied, and it quickly followed up by the sound of her taking another screenshot.
“I should go clean up a bit,” Bailee laughed and walked naked to the bathroom.
“Is she walking okay after all of that,” Hailee jokingly asked me.
“Her legs looked a little shaky,” I told her, and we both laughed. Hailee and I talked a bit after that. I thanked her multiple times time for letting me do all of that, and she told me that when I got back to LA I would have to show her how grateful I was. After a few minutes, she said that she had dinner plans for that evening and she had to get ready (It was only 6 PM in LA at the time). She told me that trusted me and knew I’d follow the rules we had for open relationships, and told me to make sure Bailee had a memorable time. We then exchanged ‘I love yous’ before she logged off and I closed the computer. When Bailee came back in the room, I was lying in the middle of the bed and she pounced on me saying that she was ready for round two. Not including oral, the two of us would have sex four more times that night. While I wore a condom each time, it always ended with me pulling it off and finishing on her back, on her breasts, or twice in her mouth. We also did not break the sleepover rule as Bailee did leave at around 4 am after she had me take her ass one more time while we showered. We texted the next day, making sure we were both still cool with what happened and making it clear this was more or less a one-off thing. Though an audible groan did escape my lips as I read a text response. She said she understood but she was on set and she could practically still feel my cock in her ass and it was making her so wet she’d practically soaked through her underwear. She invited me to come and visit the set of her show, but only as friends. I was tempted to take her up on the offer since I had two days left in Toronto, but I ultimately decided against it.
Three days later I flew home to Los Angeles. After multiple delays due to bad weather, I arrived at LAX late at night and had a car service drive me home. Hailee and I had both agreed years ago that it was not that important for one of us to pick the other up from the airport, both because it was a real hassle to get to LAX and also because the last time one of us went to pick the other up, we were almost caught having sex while parked in the parking garage. Ever since then, we’ve left our welcome home greetings to the privacy of our home.
It was a little after midnight when I walked through the front door. The first thing I noticed when I entered and put down my suitcase was the absence of noise. Neither of Hailee’s dogs, Martini and Brando, nor the rescue dog I got because I wanted a dog that wasn’t small enough for me to carry in one arm, Sydney, were running around to greet me. I was tired so I left my bags by the door to deal with later. Walking around a bit, no one seemed to be downstairs, so I went up to the bedroom. The lights in our bedroom were off but the bedroom was illuminated with about a dozen lit candles spread around the room. On the bed was my wife, laid out wearing a shiny but see-through dress over what was essentially a white bikini. Hailee looked incredible and while looking at her my feelings of exhaustion faded and my feelings of desire rose. Unfortunately, she was also asleep. She’d obviously drifted off while waiting for me. I stood there a moment, pondering my next move.
I decided not to wake her up but thought I’d help her put her sheer dress away. Kicking off my sneakers I got on the bed and moved toward her. I slowly pulled down her shoulder straps, and then gave the dress a light tug as I moved it down her body. She stirred a little as I finished pulling the dress down her body and off over her legs. Once it was off, I got off the bed and folded the dress carefully over the back of a chair in the room.
Heading back to the bed, and looking over Hailee’s body, I had a slight change of heart and I decided that maybe I should wake her up and let her know that I was home. Rather than shaking her awake or calling out her name, I started by rubbing my hand up and down and silky smooth thighs. Hailee’s body fidgeted in her sleep as I touched her. Moving further up, a light moan escaped Hailee’s lips as I brushed my hand over her sex. Even with the cloth barrier between us, I could still feel heat begin radiating from her. With a bit more rubbing, I could feel her getting warmer, and when I hooked her bottoms and pulled them aside I could see Hailee had fully shaved in preparation for me coming home. Once expose to me, I did not wait long to bring my lips down to kiss her vaginal lips.
I began with just a few kisses and then a few licks. While I got some reaction from my light teasing, she remained asleep. I quickly changed things and abandoned my teasing. I instead began eating her out as though she was awake and begging me to go down on her. It was when I upped my intensity that she began to respond. Her breathing was getting quicker and her body began to twist and stir more. I could sense that she was close to waking up if she was not already. So I shifted my gaze and looked up towards her face as I continued my oral assault on her snatch.
“Eddie, you’re home,” Hailee moaned, though her eyes were still closed.
“Even with you’re eyes closed, you can still tell it’s me?” I asked
“I know that tongue anywhere,” she replied as she opened her eyes and looked at me with a smile. I moved up her body and kissed her. She moved her hand behind my head and held me in place as she kissed me back. As we kissed each other I used one of my hands to continue my work from before and began fingering. “I was supposed to be the one that surprised you tonight.”
“Is that why the dogs aren’t here?” I asked.
“They’re with my parents. Thought we could use the privacy tonight.”
“Good idea,” I told her. Then I moved back down and finished what I had stated. I kept fingering her while I licked and sucked on her clit. As she got wetter and wetter, I feverously licked her. I knew Hailee was close to not only climaxing but also having a big climax because she moved her hand down to the back of my head. She does not do that move often but when she does, it’s because her body is ready to explode. And so she did. Drenching my face with her pussy juices as she held my mouth in place, while the rest of her body trembled in bliss.
After she came, I moved back up the bed and kissed her again. The two of us lay side by side making out on the bed for quite a while after that. My hand moved all around her body and her’s mind. As we kissed, my hands removed her top and freed her breasts. She in return pushed my shirt and sweatshirt off. She mainly had kept her hand north of the equator as we kissed, but when she finally did move her hands south I was already hard as could be. It felt good having her hand press up against me even through my jeans. So good I even let out a small moan.
“Why are your pants still on?” Hailee asked. Though her words may have been in the form of a question, it was clear that she was giving me an order. I removed my pants as quickly as I could, and Hailee removed her soaking white bikini bottoms. Once my pants were off, Hailee quickly rolled over on top of me. With me on my back, Hailee was now on her knees sitting on my stomach. My hard cock was pointed straight up, and Haillee moved back so my cock was now lined up in the middle of her butt crack. Her two soft yet strong cheeks straddled either side of my shaft. She then moved her hips and began rubbing herself back against my manhood.
“Remember when you and Bailee were together and she said that her ass is yours? That it belonged to you?” She asked me.
“Yeah,” I said, unsure of where this was going. Hailee then raised her hips and moved backward. When she lowered herself back down, my cock was now straining right in front of her. She wrapped both her hands around my shaft.
“Well, I want you to remember that while her ass might belong to you, your cock belongs to me.”
“I had no allusions otherwise,” I told her. “Bailee is fun, but she isn’t you.”
“Good. That’s what I like to hear,” she said as her hands continued to play with my shaft.
“You know what I’d like?” I asked.
“What’s that?”
“For you to prove that that dick is yours,” I told her. Hailee gave a lip-biting smile in response and then raised her hips. With my cock still in her hands, she lined it up and sunk her body down on it. Letting out a bit of a grunt as she took most of my dick with one thrust. Hailee then began riding me hard. At first slamming her pussy down my meat pole, before switching things up and going from bouncing up and down to swiveling her hips and grinding on top of me. As she bent over to kiss me, I took a firm grip on both cheeks of her ass, and just groped her firm booty.
“Ummm, I missed you,” Hailee said as she continued to ride me.
“I missed you too,” I told her before kissing her along her collarbone.
“I missed how good your cock makes me feel.”
“I missed how good your pussy feels.”
“Even after you got with Bailee.”
“Hell yes,” I told her emphatically. I put my hand on her chin to make sure she was looking me right in the eyes as I told her, “If I had a choice between a single bathroom quickie with you or a week-long sexual bacchanalia with Bailee, I’d choose you every time.”
“God, I love you,” she said before mashing her lips against mine. As we made out, I rolled us over so I was on top and she was on her back. Hailee quickly wrapped her legs tightly around my back as I hammered into her. It wasn’t until she had an orgasm that she let up on the grip her legs had around me. Once I was free to move, I sat up and grabbed one of her legs, and lifted it in the air.
“God, your legs are still as perfect as they were the first time I ever saw you,” I told her as I kissed her from her calf to the thigh before resting it on my shoulder. I then did the same to her other leg. I put my hands on her hips and began thrusting my hard rod in and out of her.
“Your cock is mine, right?” Hailee asked while trying to catch her breath.
“Always,” I answered her.
“Then make my pussy yours. Fill me and make me yours,” she pleaded. She repeated herself a few more times until I could not hold back anymore. I pushed her legs off me and bent down. I kissed Hailee while delivering one more hard thrust, and my cock erupted, Feeling me blast inside of her, Hailee once again wrapped her legs around me, and tighten them as much as she could, keeping my cock fully inside of her. As I shot rope after rope of jizz deep inside of her, the two of us remained lip locked. Even as we moaned in pleasure, we moaned into each other’s mouths as we kissed. Hailee came almost at about the same time as me.
Exhaustion and comfort then took over after we both came. The two of us soon drifted off to sleep in each other’s arms. We slept soundly until Hailee’s alarm to get up for her morning workout startled us both awake. After turning off the alarm, I convinced her to skip her usual workout routine and stay in bed with me. While she skipped her time on the treadmill, the two of us still put in serval hours of cardio work in bed that morning.
A week later, Hailee and I were in our bedroom getting ready to go out for dinner. After getting out of the shower, I entered our large shared closet to get my clothes for the night.
“Oh wow, that’s what you’re wearing?” I said when I saw Hailee standing in front of the full-length trifold mirror at the back of the closet. Hailee was wearing a long light-weigh black dress with red beach designs that included palm trees. “Are you sure we need to go out tonight? I think I rather just stay here with you.”
“Na-uh, we can’t cancel on them again,” she replied. We were planning on having dinner with Olivia Holt and her boyfriend. We had already canceled dinner with them the last two times we had planned to get together with them. While we were each still friends with Olivia, neither of us liked her boyfriend. I found him uninteresting, thought he believed he was a lot funnier than he was, and the only thing that he and I seemed to have in common was that we were both men who had had sex with Olivia. Though I am not positive he is aware of the last part. “They’ll start thinking that we don’t like them and are avoiding them.”
“But we don’t like him and would rather avoid him.”
“Yeah, but we don’t want them to know that. Besides I’m sure Liv will break up with him soon.”
“That’s what you said two months ago,” I reminded her, as I continued getting dressed. “I’ve never understood people who drag out the ending to the relationship. They know it’s not going anywhere, some don’t even like the guy anymore, and yet they’ll still drag the thing out for another few months. When I knew the relationship had an expiration date, I ended it.”
“Well, some people are not as comfortable being alone as you. Most people don’t enjoy going to the movies or basketball games by themselves.”
“You’re there to be entertained by what you’re watching in front of you. I don’t get why that’s weird to go alone. Is it just so you’re not sitting next to strangers?” I said defending myself.
“She’ll eventually dump him just like she did the others. Just give her time,” Hailee said as she decided what heels she wearing with her dress.
“Yeah well, one of those exes I had to fuck her in front of him for her to finally end the relationship,” I said, referring to the first time I ever met Olivia at her birthday party. Hailee was not entertained by my comment and shot me a look where she almost seemed to have daggers in her eyes. “I’m not suggesting that as an option this time around. I’m just saying that it can take something big to jolt her into action at times.
“Uh-huh,” Hailee replied, in a way that let me know that she was unconvinced by my defense.
The two of us finished getting ready and drove to the restaurant. After hitting some unexpected traffic we got there about 15 minutes late and were told by the hostess that Liv and her boyfriend were already there. She led us to the table, and as we approached I felt some dread.
“Sitting across from each other at the table? This can’t be good. We can still make a run for it.”
“Be good,” Hailee said quietly and gave me a bit of an elbow to the chest. As we got closer, neither of the two of them looked to be particularly happy to be sitting with the other. It wasn't until Olivia saw us approaching that her facial expression perked up. She was quick to get up and greet us while the boyfriend stayed seated and just said hi as Hailee and I sat down. It did not take long for Hailee and me to feel the obvious tension at the table between the two. I texted Hailee under the table that I was looking forward to telling her ‘I told you so’ when we get home. She replied with a middle finger emoji, which put a smile on my face.
Hailee, Liv, and I had no issue talking and conversing about stuff, but when I tried to make small talk with the boyfriend, it was like pulling teeth. No matter what topic one of us tried to bring up, it seemed like the other person had nothing to say or didn’t enough anything about the topic to keep a conversation going. When he did engage with whatever topic Haile, Olivia, and I were talking about, it always seemed like either he was undercutting something that Olivia was saying or vice versa.
It is amazing that when you have a partner that you really know well and have spent enough time around, the two of you can have almost an entire conversation with just a look. Being someone who naturally has a sarcastic and witty sense of humor, there were times when I wanted to comment while Olivia and her boyfriend bickered. Hailee would just give me a look that says ‘don’t say it’ even before a thought of what to say could form in my head. And she was right to give me that look. Saying something would have only thrown gas onto the fire. So after everything I did to try to keep the peace, it was a surprise that Hailee was the one who finally snapped.
When the check arrived, I went to pick it up and pay for the dinner, but Olivia said that she wanted to split the bill. After some playful back and forth, her boyfriend told her to let me pay. When Liv questioned him, he said I had lucked into my money and that if I wanted to spread the wealth, she should let me. His comment did bother me. It was true. Despite all the hard work I had put in over the past several years, I had won a ton of money from my jackpot winning years ago. However, Hailee could not let that slide.
“Excuse me? May have won some money years ago, but he has worked really hard and been successful at producing. He works harder than most people I know, and he for sure works harder and is better at his job than you are at yours,” Haiee snapped at him.
“Oh please. He won some money and down just makes money off of funding other people’s work,” he replied
“Babe, there is way more to it. I’ve seen him on set, Eddie works very hard,” Olivia spoke up.
“You’re taking their side? Seriously?”
“I am because what’s your side? Eddie works hard. You spend most of the day lounging around my house. And why do you even care who pays for dinner? It’s not like you were going to pay for anything. If we had split the check it was going to be my money we would have spent. Like always.”
After that, Hailee and I bowed out of the fight as the two of them went back and forth for the next five minutes until he got up and stormed out of the restaurant. He just left Olivia sitting there with Hailee and me. Liv did not try to stop him nor did she get up to go after him. After he stormed out, Oliva called the waitress over and ordered dessert for the table. While the first few minutes of us just sitting there were awkward, things were kind of pleasant by the time dessert arrived. Things were pretty normal as we ate and when the updated check arrived at the table, Liv had her credit card out before it even hit the table.
Things started to get tense as the three of us got in my car to drive Olivia back home. The closer we got to her place, the more wound up Olivia got about the things she was going to say to him. By the time we pulled into her driveway, Livv was the maddest I had ever seen her. His car was there and the lights inside were on. As she entered her house I turned to Hailee and asked, “Should we wait a few minutes?”
“We probably should give it five minutes,” she replied. Within three minutes she got a text asking if we were still close by. When Hailee texted back that we were still outside, Holt said she’d be out in five. I then suggested to Hailee that we have some red wine and popcorn delivered to our place because it could be a long night. As Hailee was finishing the order, Olivia came back out wearing the same dress she had worn for dinner but had switched her footwear from heels to sneakers. She also had a large back over one shoulder and in her other hand, she had Roger’s leash, with Roger leading the way as they walked to my car.
“Isn’t this your house?” I asked, pointing out the fact that instead of booting out the boyfriend, she was abandoning her place.
“I told him he had 24 hours to pack up all his shit and get out,” she answered. The entire way back home we could hear Olivia’s phone going off with text notifications. She would reply occasionally with voice notes and other times with her fingers would type away a response.
“Oh, wow. Now he’s begging me to come back so we could talk it out. He’s so full of shit,” Liv said with a mix of disbelief and anger.
“Maybe you should tell him where you keep your vibrator so he can go fuck himself with it,” I sarcastically suggested.
“No don’t…” Hailee said, but her words were cut off by Olivia.
“Yes, that’s perfect!” Liv said excitedly as she began typing away.
When we got home, a Gopuff delivery bag was sitting at the front door. Walking inside our three dogs happily greeted Hailee and me, and they were also excited to see Roger there as well. Olivia had come over to the house with Roger before, so the dogs all knew each other and had gotten along. Oliva went to bring her bag to the guest room as Hailee let the dogs outside.
I took the Go Puff bag to the kitchen. As I opened one of the bottles of red wine, Olvia came walking in dressed in sweatpants and a tight tank top.
“Just opened a bottle, do you want a glass?” I asked her.
“Yes, thanks,” she replied. However she did not wait for me to pour a glass, nor did she take the bottle and pour her own glass. Instead, she took the bottle and drank straight from it. Taking two big chugs, she then grabbed a bag of popcorn with her other hand and walked towards the living room. Hailee and I kept Olivia company for a few hours as she vented everything she did not like about her boyfriend and all the fights they had had. As she vented she kept drinking right from the bottle until it ran empty. Eventually, Haille and I said good night to our short blonde friend and we retired to our bedroom.
“So, I think a I told you so is in order,” I said as we walked into the bedroom. “I told you we should have just canceled on tonight.” I expected some kind of blowback from Hailee, but instead, she surprised me by wrapping her arms around me and giving me a big passionate kiss.
“Thank you,” she said when our lips finally broke apart.
“After a kiss like that, I am pretty sure I should be the one thanking you.”
“No, thank you for not being a total shithead like some other guys,” she explained.
“That’s all because of you,” I told her before kissing her again. We slowly moved towards the bed, with me losing a piece of clothing with each step. Once I was down to my boxers, the back of my legs hit the edge of the bed and I took a seat. Hailee, meanwhile, took two steps back away from me. I looked her over. Still dressed in the same clothing as what she had worn to dinner, minus her heels which she took off downstairs. Hailee reached behind her neck and undid the back of her dress. She then slowly, and teasingly began lowing it down her body. When she had it down around her waist, instead of continuing, she stopped to remove her backless bra. Even after all these years and countless times I had seen her naked, I still began salivating as Hailee exposed her tits. She ran her hands over her breasts before continuing down and finished removing her dress, letting it fall and pool around her feet after pushing it past her hips.
Hailee was now left standing in nothing more than her black tanga-styled underwear. She stepped up close to me and then took my hand and placed them on her hips, right at the edge of her panties. I hooked my fingers into the waistband and removed them. Hailee now stood naked before me and I bent forward and kissed her right above her pussy. My lips brushed up against the hairs of the patch that she was let grow in.
I moved to remove my underwear, but Hailee stopped me. She took a step back and had me stand up as she dropped down to her knees. She pulled down my boxers and my hard cock sprang forward. Hailee pressed her lips against my cock and gave the tip a light kiss. I could barely even feel her lips press against my cock head. Then she did it again, and again. She took the base into her hand and kissed up and down my shaft before returning to the tip. She took it into her mouth and swirled her tongue around the tip before messaging the sensitive spot just under the tip. It all felt unbelievable, but I knew that she was just giving me a little bit of pleasure. And appetizer before moving on to the main course.
She got up and we both move onto the bed. This was not going to be a lot of foreplay action like we often like to do. Instead, Hailee laid down on her back and pulled me on top of her. I gave a hard thrust of my cock into her, causing her to gasp, but after that, the two of us just kissed and made out lovingly. We stayed like that for a while, just making out while basically in the missionary position and my cock resting inside of her. After a while, I did begin to rock my hips as we continued to kiss. While the two of us knew how to fuck each other, this time it was much more lovemaking than anything. Our tempo was much slower and tender. When our lips were not pressed against each other, we were staring directly into each other’s eyes. We told each other how much we loved one another repeatedly. I was surprised with the way that we were going, that when I warned her I was about to cum she asked me to pull out. She had to tell me twice before I finally did pull out and I got up and sat on my knees. Hailee then sat up and bent over, swallowing the first few inched of my cock while her hand pumped my shaft. With my dick slick with Hailee’s own juices, her hand easily slid up and down my shaft, jerking me off while her tongue played with the tip of my cock. It was only a matter of time before I began firing off blasts of cum to than back of Hailee’s mouth which she quickly swallowed.
“Fuck, Hailee you’re so incredible,” I told her after I finished.
“You’re pretty great yourself,” she complimented me.
“That was so hot,” said a third voice away from the bed. We both quickly snapped our heads around to where the voice came from. There in the doorway, we both saw a drunk and horny Olivia Holt leaning against the door frame. Liv still had on her sweatpants and tank top, but her shirt had been rolled up to just under her breasts, and her hard nipples could be seen poking through. And while her pants were on, she had one of her hands shoved inside of them and she had clear wet spots on the crotch of her pants.
“What the fuck?” Hailee yelled when she saw her standing there watching.
“Sorry,” Olivia said with a breathy voice. “I could hear you guys down the hall, and then when I walked by the door was open and… I just couldn’t look away. You two are so hot together.”
“But still, Liv…”
“Sorry, but I started watching, and then I started thinking about the times the three of us got together, and I just got so horny I couldn’t help myself.” As Olivia spoke and drunkenly tried to explain herself, her hand never left her pants.
“Go to bed and sleep it off, you’ll feel better in the morning,” I calmly told her.
“Yeah, you’re right. Sorry,” she said as she finally pulled her hand out of her pants, her fingers glistening with wetness, and she turned to go back down the hall to the guest room.
“I kind of feel bad for her,” Hailee said after letting out a deep sigh and running her hand through her hair. “She looked sad and horny. That’s like the worst combination.”
“Yeah, well, she’ll be fine. Especially after she gets some sleep. You’ll see, she’ll be way better in the morning,” I told her. I then kissed Hailee on the side of the neck.
“You’re probably right,” she said.
“Now, should I close the door or should we keep it open and let her keep listening? Because I am ready to go again.” I told Hailee as I kissed my way down the middle of her chest. I was about to suck on her tit when Hailee pulled my face up to hers and she gave me a big exaggerated kiss on the lips.
“I love you,” she said to me and then she called out to the hallway, “Olivia, are you still there?”
There was a minute of silence before we heard Olivia timidly respond, “No,” from just next to the door frame.
“What are you doing?” I asked Hailee quietly.
“I love you, I trust you, and she really hurting.”
“So?”
“So, I want you to absolutely wreck the bitch,” Hailee quietly answered me. She then called back to the hallway, “Come in here!”
As the short blonde singer crept back into the bedroom, I looked at Hailee for confirmation that was sure about this. She gave me a nod, and then we both turned to Liv. No one said anything or did anything for a moment. Finally, I made a move. I got up off the bed and began walking to Olivia. As I moved toward her, her eyes were not looking at me. Her eyes were locked on my hard-as-steel manhood jutting out in front of me.
“In all your rantings about your ex, you never said anything about your sex life,” I said as I stood inches from her.
“He could get me to climax most of the time, but it’s been a while since I came so hard my leg was still twitching minutes after,” Olivia told me, moving her eyes up to meet mine for the first time.
“What do you say we change that?” I didn’t wait for a response. I picked up the actress and tossed her onto the bed. With her on her back, I grabbed her sweatpants and ripped them down her legs and off her body. Olivia had grown a blonde bush, but she was so wet the hair had been matted down. I grabbed both her legs, spread them wide, and then pushed them up above her head. With her wet snatch now splayed in front of me, I then dove down and attacked it with my mouth.
“Oh yes! Fucking eat my pussy, Eddie! Eat me!” Olivia cried out. If there was any question about how horny Olivia was, that question was answered as she came within two minutes of me starting to go down on her. However, even as she came, I did not relent a all. Outside of Hailee, there was no one else I had ever enjoyed going down more on than Holt, and with being allowed to go down on her again I was not going to stop after only two minutes. Even with a bush, she still had one of the prettiest pussies I’d seen and she also had one of,if not the, best-tasting pussy I’d ever sampled. So given a chance to taste her again, I ate her out like it was the last time I might ever get to do it.
I devoured her pussy until I had her right at the edge again, and then I backed off. I started licking the excess juices that had spilled over onto her upper thighs. When she had calmed down, I went back to her pussy and ate her out some more until she was right on the verge, and then I backed off again. I moved away from her pussy and went to play with her hard dark nipples instead. I would go on to edge her again one more time before Olivia got mad at me.
“What are you doing?” She yelled.
“You know exactly what I’m doing and what I want,” I told her.
“Please just keep going.”
“You going to do it,”
“Uh-huh, yeah,” she cried. So I moved back down her body and went back to sucking on her clit as I fingered her. Sure enough, Olivia did exactly what I wanted. What I loved making her do. When she climaxed again, she also squirted. And not just a small trickle, she shot some juices up in the air as her body erupted. Olivia said that she had not had a real body-shaking orgasm in a while, well based on the way her eyes rolled back as she came it seemed safe to say that that streak had ended.
“Well, looks like you got her off pretty good,” Hailee commented as she looked at Olivia lying there trying to catch her breath.
“Yeah, maybe we should give her a break for a minute,” I said as I moved over to Hailee and the two of us started to make out and grind against one another as Liv laid next to us. Hailee was still nice and wet as she rubbed her pussy up and down against my rod. I was getting ready to thrust into Hailee when all of a sudden Olivia began to stir again. She was on her knees behind me, pressing her tits into my back as she began kissing my shoulder.
“I want your cock,” she whispered in my ear.
“I think you need to wait your turn I told her,” I told her.
“I’ve been waiting for like five years, and you just fucked tonight,” Oliva whined as I continued to pay more attention to Hailee than her, and Liv did her best to tempt me to turn around.
Hailee then moved in close to me, and whispered, “Remember what I said before? Wreck her.” Hailee then pulled away and gave me a quick kiss on the lips before moving her body away. I then spun around, and before I had any time to react Olivia pounced on me knocking me back to the bed. She mashed her lips up against mine and then I felt her grab my cock. She began rotating her hips around the tip of my cock until she had the correct angle. Once she did, she sat down on it.
“Oh fuck me! I’ve missed that feeling,” she said as sat on my cock. She stayed bent over my body as she began bouncing her pussy along my dick. I had to admit she felt incredible.
“You feel good Liv. So freaking tight,” I told her.
“That’s because I haven’t been properly fucked by a cock like yours in a long time,” She told me. She then looked up at Hailee and told her, “You’re so fucking lucky.”
“I know,” Hailee said confidently.
Olivia rode me hard for a good while. But eventually, we switched things up. I knew what Olivia liked so I had us get off the bead and move over to the dresser where we had a large mirror above it. Olvia quickly took to bending over and bracing herself against the edge of the dresser. Sticking her cute ass back toward me. Getting behind her, I grasped her hips and sank my cock into her. Once inside her, I looked up at the mirror, and the former Disney Channel actress and I met eye contact through the mirror. Whatever drunken haze she had in her eyes when Hailee and I first saw her in our doorway was good. Now all that was lust and determination. “Fucking pound me. Hard,” she ordered me. So I went hard. You could hear the sound of my pelvis hitting her ass with each thrust, and you could also hear the sound of her dresser banging against the wall as well.
“Oh god just like that,” she moaned as we went at it. She especially loved when I wrapped my arm around her body and began tweaking her nipples a bit. Olivia looked at my face through the mirror the entire time, and while I did try to focus mostly on her, my eyes would occasionally dart over my shoulder to the brunette openly masturbating on the bed. I didn’t like the idea of just focusing on Liv while Hailee was also left in the room unattended by herself. So I was happy when Liv’s leg buckled and she finally had another orgasm. As she came I withdrew my cock and let her recover a bit. When she was good, I made a suggestion to her.
“You know,” I said, “You should probably thank Hailee for letting this happen.”
“Oh?” Olivia said playfully. “Do you think a thank you note and a bottle of wine will do?”
“It’s a good start, but I was thinking something more immediate.”
Olivia then went over to the bed and got on it right between Hailee’s legs. While she teased my wife for a bit, Olivia did eventually show how thankful she was and began eating her out with the same effort I had given her early in the night. I sat back and waited for a little bit, though I could not help but notice the way Olivia kept her ass up high in the air as she ate out her friend. Eventually, it was all too tempting for me. I could not sit back and watch any longer. In a flash, I was on the bed and slamming my cock back into Olivia as she continued to feast on Hailee’s twat. So now it was the three of us on the bed with Hailee on her back, Olivia on her elbows and knees between her legs, and me on my knees behind Liv.
“I want to taste her,” Hailee announced at one point after Olivia had gotten her off once. I knew right away what she meant. So I withdrew my manhood from Olivia, much to her disappointment, and moved over to where my cock was easily accessible for Hailee’s mouth. “God, she really does still taste fucking amazing,” Hailee said as she sucked some of Holt’s juices off my cock. She continued to suck and lick my cock until it was no longer coated in any of Olivia’s pussy juices, but only in Hailee’s saliva.
At that point, it was time to finish her off. Olivia got flipped over onto her back and Hailee moved to straddle her face while I moved between her legs. I couldn’t help myself from getting another taste of Olivia fresh from the source, so I gave her a few licks before moving into place and reinserting my cock into her. I once again lifted her legs up and spread them wide as I gave it to her hard and fast. Hailee once again came on Olivia’s face, and Liv was not that far behind with an orgasm of her own. I was the last holdout.
Hailee moved off Liv’s face, and she also took her ankles from my hands and bent the Kicking It actress’s legs back. I was getting close, and I was about to give a warning but Hailee spoke up before I could. She must have new from the look on my face what I was about to say.
“Eddie,” she said. “Remember our rules?” she asked.
“Yup,” I responded. Figuring she meant no creampies in or from others, I began to pull back out until Hailee said something else.
“Forget them tonight. Fill her.”
“Seriously?”
“Mmm-hmmm,” she nodded.
“What’s happening?” Olivia said in confusion.
“This is what’s happening,” I told her and 15 seconds later I detonated inside of her.
“Oh my god yes! Give me it all! Fucking Fill Me!” Olivia screamed as she felt me shooting a seemingly never-ending load of jizz inside of her. Even I was surprised by the amount I came.
“Damn, that was a good one,” I said when it was over.
“I think you mean a huge one,” Olivia corrected me. “I didn’t know if you were ever going to stop.” When I pulled out, a river of white cum began flowing out of her.
“If only your boyfriend could see you now,” Hailee joked.
“Ex-boyfriend,” Liv retorted. And I wish he could. Would be no questions about if we were over or not now.”
“My phone is in my pants pocket,” I said half joking.
“Get it,” Olivia said in a serious voice. I got out of bed, found my pants, and took out my phone. Once on the bed, Liv had me take several close-up photos of her wet pussy that was leaking my cum out of it. After about a dozen photos, including one where she used her fingers to open her pussy lips up wide, she took my phone and browsed through the pictures. Commenting on which ones she liked the best and sending those to her phone.
“I’ll send it to him in the morning,” she said. Olivia more or less passed out after that, leaving Hailee and I still wide awake on the bed. We ended up screwing each other's brains out on the bed one more time with Liv sound asleep right next to us. Sleeping through all the shaking of the bed and all the loud sex noises we were making before I shot my third load of the night into Hailee’s womb.
“God that was amazing,” I said to Hailee as we now laid in bed together under the covers. The two of us had our heads on our pillows and were looking at one another as we spoke. Olivia was on the other side of me still sound asleep.
“Yeah, that was fun,” Hailee replied.
“You’re still my number one, you know that right?”
“Of course I do. This was just a little bit of special fun.”
“So, I know my birthday is still a few days away but was this my present? I know you said you had something special planned,” I asked.
“Oh no. I didn’t plan any of this. Your birthday gift is still coming, and I think you’ll like that gift even more than this?”
“More than tonight?” I questioned her.
“Trush me,” Hailee said. “What I have planned is going to blow your mind,” she then gave me a quick peck on the lips before rolling over and going to sleep. I was left with my brain thinking what could she have planned that is even more mind-blowing than an impromptu threesome with Olivia Holt?
Topic: "Lucky Bastard Revisited: Still Getting Lucky" (Read 5718 times)