Lucky Bastard 22: Hanging with Hailee
Staring Hailee Steinfeld & Camila Mendes

Codes: MF, Oral, Anal, Facial
Witten by MiamiLyfe

Disclaimer: The following is completely fiction and it is nothing but pure fantasy.




October 2018

For the first time in a while my time was finally freeing up. It had been over a month since the fuckfest that was Olivia’s birthday and then getting roped into the award show with Natalie. Since then except for a few things here in there I had been busy with my movie, but now the movie was in the later stages of post production and for the most part it was out of my hands. I also had nothing new scheduled going forward. I am planning to take some time off once I get distribution for the film, but until it’s ready to show there is nothing much I can do to get that happening either.


Currently is was mid afternoon on a Thursday in Los Angeles. I was behind the wheel of my car with Hailee Steinfeld in the passenger seat. She had called up wanting to hang out while she was still in LA before leaving again. So we met up in Santa Monica to see a movie, have lunch together and catch up. I told her about my film, she told me about her concert tour and about how filming her new show Dickinson was going. Of course with us being who we are and the nature of our friendship being what it was, the conversation eventually turned to sex. She had me go over ever detail about everything that happened at Olivia Holt’s birthday, and then everything I saw and did with Natalie at the Teen Choice Awards. Hailee then told me about her time hooking up with one of her dancers in a locker room shower in Portugal. When I asked her if she and the tour headliner, Charlie Pluth, ever hooked up she said no. Charlie was very obvious in his desire to get with her, but Hailee thought he was kind of creepy, so she just kind of teased him. The last night after the final show she texted Charlie to come down to her room, but if he wanted to see her naked he was going to have to sneak down to her room nude. She then gave him the wrong room number and he ended up naked knocking on so elderly couples door.


Currently Hailee was telling me story about one night in Minneapolis after a not getting any for a few days, and she meet two male fans in the hotel bar.


“So I was on my back with my had hanging off the bed and my legs being held straight up by the taller guy. He was pounding my pussy while the other guy fucked my mouth. All three of us ended up going on like that until it ended with both blowing their loads all over my chest.”


“So were they actually your quote biggest fans, like they said at the bar?”


“No, you’re defiantly a bigger fan than either of them, though they were quite enthusiastic fans,” Hailee then laughed as she kept the euphemisms going. “So, come on. Give me another story, we’re only halfway home.” We were on the way out to Thousand Oaks where she still lived with her parents.


“I really don’t have anything. Things have been kind of boring,” I responded.


“Nah-uh. I call b.s. Are you telling me you haven’t gotten laid in the last couple of weeks?”


“I didn’t say that.”


“Well then? Come on, tell me. I’ve told you everything already.” This was true. Hailee had told me 4 or 5 stories, the lone exception being about her and Nial. Her boyfriend had been the one topic the two of us had skirted around. Other than some basic stuff, there was just an awkwardness that seemed to come over the conversation when he came up.


“Okay, I have one other story and it relates to what happened at the award show.”


“Oh, that sounds intriguing.”


“Okay…”


********************************************

Two weeks after the Teen Choice Awards, I was out on a midmorning walk at Brookside Park getting some exercise and catching up on some podcasts. I had been going for about an hour when I got a text notification on my phone. The message was from a number I didn’t have programed into my phone and didn’t recognize. The message read “Nice cock” and it was quickly followed by another text, this time it was a picture. The picture was an overhead shot clearly looking down at the lower half of my body in a bathroom stall at the Teen Choice Awards, and Natalie Alyn Lind kissing the side of my shaft as she squatted down and held my cock.

“Who is this?” I quickly texted back.


“You don’t have my number in your phone? That’s disappointing” they texted back.


“What do you want?”


“Don’t worry I’m not blackmailing you. The photo is just for me.”


“So? Why are you texting me?”


“To let you know that you have a nice big cock.” The person then sent another message before I could respond again “And that I bet it would look even better sliding into here.” Attached to the message was a closeup picture of a very wet pussy with the labia lips being held open by two fingers. By the color of her skin I had a pretty good idea that whoever I was talking to was either hispanic or white and spends a lot of time sunbathing in the nude.


“Seems like you’re pretty wet, if you let me know who you are maybe I could help you out” I texted back to her.


“I’ve fucking drenched my sheets fingering myself to the picture of you. Meet me at the W Hotel in Hollywood in an hour.”


“Let me know who you are first” I texted back. I was not going to meet some stranger at a hotel. This could be some kind of set up for something, and for all I knew that photo that was sent could have taken from some porn site.


“Come on. I want it to be a surprise. Trust me, you won’t be disappointed.”


“Text me who you are, WITH PROOF, or forget it.” I didn’t get an immediate response this time. It took 2 minutes before I got a new text message, again with a photo attached.


“W Hotel room 647 in 1 hour. Trust, I’ll give you a night you won’t forget.” The picture was a close up of an exposed c-cup tit with dark brown nipple and part of a tattoo under it. If these photos were from the same person, she had a good body, but without knowing who it was I was not going to actually go and meet this person. That said, I did download the pictures to my phone, and I also texted the one of me and Natalie to Nat with the message, “Well, you said you wanted proof for Sklyar & Jamie. Here you go.”
She was a little freaked out at first that we had been caught, but I told her that if they were going to release it or blackmail us for money, they would have already have done so. That seemed to calm her down.


Six hours later I was back at my house when someone started banging on my door. I opened it up and Camila Mendes pushed passed me and walked into my place.


“I can’t believe you just let stood me up at the hotel” she said angrily. She was dressed in a large oversized hoodie that went almost down to her knees, and also had on some black heeled boots that when up to her mid calf, and black stockings.


“Camila? What are you doing here?” She then whipped around and looked at me angrily.


“You stood me up at the hotel. I don’t like being stood up” She spoke slowly and deliberately to emphasize her point and her displeasure. It took a second for it to click what she was talking about.


“You’re the one who texted me?”


“Duh! Who did you think it was?”


“Literally anyone! It literally could have been anyone. That’s why I didn’t go. It could have been you, or it could have been some 56 year old seat filler. I didn’t know. Those pics you sent of you could have been taken off the web. Why didn’t you just say it was you?”


“Because I was trying to be sexy and mysterious. GOD!” She then stormed off deeper into my place.




************************************************************************************************


“Blah, blah, blah,” Hailee interrupted me. “Hurry up and get to the sex.”

“I’m getting there. You wanted to hear the story, so I’m telling you the story,” I told her.


“Well, hurry up and get to the good part.”


“All right, well she tells me how she broke up with her boyfriend and how she technically single while waiting to announce that she is dating another actor on her show. She then takes off her sweatshirt to reveal she is wearing a black lace half cup bra with matching thong and garters. She then went on about how after catching me and Nat she couldn’t get the image of my cock out of her head. So I lead her upstairs to my bedroom.”


“Now we’re talking.”



************************************************************************************************




“Take off your bra and thong, but leave on the garters and heels, then get on the bed,” I told Camila as I stripped off my shirt and pants.

“All right now what?” Cami asked as she laid back on my pillows with one arm behind her head looking at me. I let my eyes move up her body, from her sharply legs to her pussy with a well maintained short cut bush, to he tone stomach, to her breasts with quarter sized brownish nipples, to her smiling face.


“Now,” I say as I climbed up onto the bed dressed in just my boxers, “I make up for leaving you hanging at the hotel.” I then picked up her leg and slowly started to kiss my way up it. Camila laid back with her closed eyes closed and enjoyed the feeling of my lips as they crept closer to her honeypot. Camila moaned and slid her hand to the back of my head as I started kissing around her pussy lips. She started pressing on the back of my head as my lips sucked on her clit and I slid a finger into her. She started moaning louder as a flicked my tongue rapidly against her clit and push another finger into her. She was now pushing her hips up into my face as I ate her out. I thought she was getting close to cumming when all of a sudden she pulled my face away from her.


“What’s wrong?” I asked thinking that something must be wrong.


“Nothing. Get on your back, I want to sit on your face.” Cami got up on her knees as I got down on to the bed. Facing the head board she straddled my head between her knees and then dropped her crotch down onto my face. She said something in Portuguese I did not understand as she began gyrating her hips while I ate her out. I was right about her having been close to cumming as it only took another minute or so before she came all over my face for the first time. She did not stop though. The Riverdale star kept riding my face past her orgasm and did not stop or give my tongue a break until she came a second time.


“Wow.” She said as she finally got off my face and laid down on her back next to me. “You’re pretty good at that.”


“Thanks,” I said confidently.


“Don’t get cocky. I said you were good, not the greatest. I know a few who are better.”


“Oh yeah? Who?” I asked as I reached over and cupped her tit.


“I’m not telling you that.”


“Come on just one name.”


“No.”


“Please.”


“No. Ow, ow, ow” Camila yelled out in a little pain after I gave her hard nipple a bit of a twist. “Fine, Lili. Happy now?”


“Lili? As in Lili Reinhart? Your costar?”


“Yup. Have you watched How I Meet Your Mother?”


“Yeah.”


“You know how in one episode Robin says Lily always tries to makeup with her when she’s drunk?” I nodded somewhat remembering the episode she was talking about. “Well, Lili is like that. She kind of gets really into girls when she is really drunk and once or twice I may have let her go down on me.”


“That’s hot” I said as I slid my boxers off. “But I know one think I can do that she can’t.” I lifted up Camila’s leg and rolled her on her side a bit. Moving my hips forward I brushed my cock along her pussy lips. She moaned as she felt my poll move against her wet taco.


“God I’ve been thinking about this nonstop the last few days,” she said as she took hold of my dick and moved it into position.
Camila bit her lip as I pushed forward and my cocked pierced her pussy. “Fuck that really is a big cock,” she moaned as I slid more into her.


“You like that?”


“I love it!” She turned her head and looked at me over the shoulder and we kissed as we began fucking in the spoon position. I continued to grope her tit as I could feel her use a hand rub her clit as I took her from behind. We were going at it at much slower more methodical pace than I usually do with most of my hookup, letting us really feel each stoke of much cock into her warm velvety pussy.


Soon the Veronica Lodge actress was asking to be back on top. I rolled onto my back again and she eagerly began to ride me reverse cowgirl. I watched as the Brazilian actress’ ass bounced up and down my thick poll until her body shuttered as she came for a third time. When she calmed down she looked at me over her shoulder while still sitting on my cock.


“What do you want to do now?” She asked.


“I want you to suck my cock clean of your pussy juices and then turn around and get on all fours.” Camila didn’t argue or say any thing. She just gave me a sexy smile and climbed off me. I propped my head up and watched as Camila moved her hair back and bent down so her mouth hovered just over my erection. I could feel her breath on my dick as she looked up at me and stuck out her tongue. Moving down, she swirled her tongue around my cock. She opened up taking the head into her mouth, and then stared to suck it clean. She didn’t demonstrate her full oral talents, instead she just did what I asked and used her tongue and mouth to clean my cock of her cum.


When she was satisfied with the job she did, she spun around and went head down ass up on the bed. She even gave her booty a bit of a shake to taunt me as I got up on my knees and moved behind her. This time when I pushed inside her, it was not tender and methodical, it was hard and rough. I had given the Riverdale star 3 orgasms, and it was time for me to get mine. I slammed my whole length into her over and over again. Her ass shook and a gasp escaped her mouth with each thrust.


As I fucked her my hands gripped and held her latin ass. I suddenly realized that one of my thumbs was resting right on top of her hole. When I saw it and idea posed into my head, but before I could act Camila yelled something out.


“What?” I asked.


“You heard me, do it. Stick your finger in my ass!” It was like she had read my mind. With that, I pushed forward and my thumb slipped into her ass. While tight, it was pretty obvious that this was not the first time she had something jammed into her ass. I continued fucking her doggy style and fingering her ass until I could not take it any more. I told her I was going to bust my nut soon.


“Don’t cum inside me” she told me.


“Where do you want it then?”


“I don’t care, literally anywhere else you want,” she said as she panted. With her full Brazilian booty bouncy against me, and my thumb still in her ass, it was too tempting to resist. Pulling my thumb out of her ass I gave her butt check a nice hard slap, then took a firm hold of her hips. I withdrew from her twat, and before she had any time to react I penetrated her backside.


“Mother fucker!” She yelled as she felt her ass suddenly being stretched out.


“You said anywhere” I told her as I started fucking her asshole. “Want me to stop?”


“I didn’t say that” she said not wanting to admit how much she was enjoying getting butt fucked. I kept slamming into her until my cock erupted and I shot my full load into her. Not pulling out until my balls were fully drained.



************************************************************************************************


“Then the next morning I woke up to her sucking me off until I came in her mouth, and we ended up fooling around a little bit more in my kitchen before she left.”


“Fuck that’s hot,” Hailee said. Out of the corner of my eye I could see her rubbing her thighs together and she also gave herself a little tit squeeze. “You’re starting to develop a good sized harem,” she teased.


“Please don’t say harem. That make me feel like some creepy rich asshole or something.”


“Well, you are rich, though I think you're more of a bastard than an asshole,” she joked.


“I don’t know if that’s any better,” I laughed.


“No joke though, you better hope Ariana Grande doesn’t find out about your ‘Big Dick Energy’ or she may just show up at your door one day.”


“Ha!”


“I’m not joking that girl is the biggest size queen I’ve ever meet. I remember accidentally walking in on her getting DP’d by these two big guys at a VMA afterparty a few years ago.”


We talked and joked the rest of the way to Hailee’s house. As we pulled into the driveway I started to say goodbye, but Hailee stopped me.


“What? You can’t seriously be leaving already. Driving me home and around right away driving all the way back to Pasadena is crazy. Come on and hang out for a while. We have the house to ourselves and I want to see your movie.”

It did not take much persuading to make me stay, especially after seeing the gleam in her eyes when she said her parents were out of town visiting her brother. We got inside and Hailee connected her computer to the living room TV so I could go online and bring up the latest version of the movie. It was on secure password protected site so only I and a few others could view it and send in some feedback before the film was finalized. As I did that Haiz said she was going to go upstairs and change into something comfy.




“Oh Hailee” I said as she reentered the living room. She was wearing a long white ‘OH HAILEE’ t-shirt that she had made for her last tour. The best I could tell, the shirt was the only thing she was wearing as she walked towards me with her bare legs and feet.

“You like?”


“Yeah. What made you think of that shirt design?”


“I was in a jacuzzi, and started thinking about that time we were in big hot tub.” She didn’t need to continue, I knew exactly what she was talking about and remembering the experience brought a smile to my face.


“If that’s true, seems like I deserve a cut from the sales.”


“I don’t know about that, but I’m sure I can come up with a way to reward your contribution” she said as she lightly stroked by arm. Though the sexual tension in the air was strong, we didn’t go any further. We instead moved over to the couch. I sat at one end and put my feet up on the coffee table. Hailee threw a pillow down on my thigh and laid down on the couch.


“What’s it called again?”


“Summers in Scottsdale. I don’t like the name. I’m hoping to come up with something better.”


We then just sat and watched. Hailee made an occasional comment or asked a question, but in general we were both pretty quiet for the first hour or so of the movie. We then got to Becky G’s sex scene. She had negotiated out of being nude on screen like the script had originally asked for, but instead wore some very revealing lingerie.


“Damn, and people say I have a nice ass. Wow!” Hailee said as Becky stripped out of her dress revealing her g-string. Hailee was laying on her stomach and as the scene continued Hailee slipped her hand under the pillow and onto my thigh. The camera now showed Becky’s bare back and bouncing ass as she simulated riding a guy. “God, I’m think I’m actually jealous of you getting to fuck her ass.” Hailee’s hand was now on resting on top of my crotch as my dick was quickly hardening. I paused the movie.


“Why’d you pause it?” Hailee asked as she turned and looked up at me with a dirty smirk on her face.


“You know why.”


“Yeah, I do.” Hailee sat up and kissed me. As she slipped her tongue into my mouth, she took the pillow that rested against my lap and flung it across the room. As we made out I kicked off my shoes and Hailee started undoing my pants. Once they were undone I push my pants and boxers down to the ground. Hailee broke off our kiss and wrapped both her hands around my pole. She ran her tongue up and down my shaft before kissing the head.


“I’ll never get tired of this thing,” she said before opening her mouth going down on my cock. Truth be told, I’ll never get tied of feeling her lips wrapped around my cock either. I was still sitting in the same spot on the couch from when I first sat down and Hailee was lying on her stomach, with her legs kicked up in the air as she deep throated me. Her hands now rested on my thigh as she let her talented mouth do all the work.


While she played with my body, I decided to play with hers. Grabbing her white t-shirt by the middle of her back, I tugged it up and slowly I exposed shapely nude ass.


“No underwear? Gosh Hailee, it’s almost like you were planning on this happening” I teased as I gave her ass a playful tap and a squeeze. Hailee pulled her mouth off my cock with a very loud pop.


“I was planning on this even before we met up, but figured if we did it before lunch and the movie that we’d never leave the house.” She then used her tongue to tease my balls. As she did that I leaned over as far as I could, moving my free hand between her legs as she sucked me off. I groaned from the work her talented mouth was doing and she was staring to let out the occasional moan as I finger blasted her. As we continued, on the back of the my hand I could feel a wet spot starting to develop on the couch.


“Good I can’t take it anymore.” I blurted out. Hailee playfully laughed as I pushed her off me. I got up and walked over to the other side of the couch. Taking a hold of her ankles I pulled her towards me until the Bumblebee star had her ass propped up in the air on the couch’s arm rest. My dick not stood straight out looking at both her exposed pussy and asshole. I thought about taking her ass, but instead decided to just slam forward and fuck her pussy. At this point we’d both fucked each other enough that we knew exactly how to get each other off. I knew just what spots to hit and she knew just how to move her body.


“Oh god, I love how your cock feels inside me. I love how you fuck me” she moaned.


“Oh Hailee. I love everything about your body.”


“Mmmmm I like that. Say my name again as you fuck me with that big dick.”


“Hailee!”


“No, like before!” I paused a moment before I understood what she meant.


“Oh Hailee!”


“Yeah, again!”


“Oh Hailee!”


“YES!”


“Oh god HAILEE!”


We went back and forth like that as I slammed my dick into her, until neither of us could hold back anymore. She came first. Her pussy clenching my cock as her pussy leaked all over the couch. I told her I was about to cum but she begged me to hold on just a minute longer. I stepped back as she got off the couch. She flung her shirt off, exposing her perky tits to me with thick hard nipples to me for the first time today. She then dropped to her knees and began pumping my cock which was aimed at her face. She could feel I was about to blast her, so she closed her eyes and puckered her lips before the first jet of semen splashed against her face. I ended releasing one of the largest loads I had in a while on her face. By the ended of it her face looked like a glazed toaster strudel.




“Jesus dude, cum much?” Hailee joked as she used her tongue to clean the cum that landed around her mouth, and then used her discarded t-shirt to clean the rest.

Minutes later we were both sitting back on the couch, this time both of us were naked. Hailee had her head resting on my shoulder, and I had an arm wrapped around her while my other hand tapped on her computer finishing our Postmates order. Turns out we had built up quite an appetite.


“So they’ll be her in 45 minutes. What do you think we should do till then?”


“I don’t know,” Hailee replied. We sat in silence for a few moments. “You know,” she spoke up, “there is one room in this house I’ve never fooled around in before.”


“Oh yeah?” I replied knowing where this was leading.


“What do you say we go up to Griff’s room and I do to you what his friends wished I did to them whenever the slept over?” He hand was now back on my cock slowly stroking me back to life.


“I think we both know I can’t say no to an offer like that.” Hailee giggled happily and gave me a quick forceful kiss before getting off the couch and took off running. I quickly got up after her and chased her naked ass up the stairs.