Lucky Bastard 5: Networking at Night
Starring Mary Elizabeth Winstead

Codes: MF, Oral, Creampie, Cheating
Disclaimer: The following is completely fiction




While I was able to sleep well after hooking up with Chloe Moretz, the next day my nerves were back as I got ready for our screening. Thankfully all those nerves were for nothing, people loved the movie. People gave Ryan an ovation when the film was over and for the rest of the day kept coming up to Ryan & I congratulating us and telling us how much the loved the film. We got a whole bunch of free drinks that night and when I got back to the hotel, instead of going back to my room, I went straight to the gym and sure enough Chloe was in there working out just like she said she would be. I fucked her right there on the bench press.

Things were a total whirlwind over the next few days. Our film was the buzz of the Toronto Film Fest and we even had a second screening of the film get scheduled. We also had distributors contact us about buying the movie. We were not to sure who to go with until Netflix got involved and offered not only gave us the biggest offer, but they also offered to finance Ryan's next project. I had already agreed to produce his next film, but with all the extra money from Netflix we could now go for our dream cast instead of going with unknowns again. We had previously thought that Mary Elizabeth Winstead or Emma Stone would be perfect for the lead and Anna Kendrick or Emmy Rossum would be great for the 2nd lead, now with this Netflix money and the buzz around Ryan, we might be able to get one of them.

The other great part about Toronto was getting to meet all these new people at the parties every night. People immediately flocked to Ryan at each party, but I soon found myself encircled by different people. Some were producers who were giving me advice, some were actors/actresses, and then there were just some other random Hollywood types. It was a lot of fun, but it was also great for networking experience for me. It was on the fourth night that I got a huge surprise as I was as a producer who I was talking to introduced to Mary Elizabeth Winstead. I told her how I was a fan of hers and she said she had heard good things about my movie. I told her that we actually had another film potentially in the works and how she was our top choice for the lead. We continued talking for a while, eventually things got switched from business to personal stuff and I told her my back story.

"So let me see if I got this all; you're young, good looking, you're super rich because you won the freaking lottery, and you happen to now be a producer for the movie that everyone here is buzzing about because you grew up with someone who happened to become a talented director, is that right?"

"Yeah, I guess." I said having a hard time myself believing that all of it was in fact true.

"You lucky bastard. Anything else about you note worthy?"

"Well I got a huge dick," I said under my breath before taking a sip of my drink.

"What was that?"

"Nothing."

"Right." She said looking at me sideways. "Lying about your penis size already, looks like someone is on a fast track to becoming just like the rest of these a-holes" Mary said pointing her glass in the towards the rest of the room indicating she was talking about all the other Hollywood men in the room.

"Hey I am a good guy, and I am also not a liar."

"Oh really?"

"Yes" I said confidently and then the image of me doing my high school teacher's daughter in his classroom entered my mind, followed by having sex with Olivia Holt right in front of her boyfriend, then me texting Aubrey a tip to seduce Oliva which was quickly followed by the image of the group of pictures he had sent me last week (several of Olivia blowing him, a close up of his dick in her pussy, a full body shot of Liv as he was fucking her, and then a close up of Olivia's smiling face with streaks of cum all across it) "Well mostly... mostly good."

"Mostly?" Mary said raising her eyebrow.

"Occasionally I may make some bad choices when I think with the wrong head" I joked.

"Um-hmm" she hummed before taking a sip of her cocktail. Mary let the dick comment go and we actually just kept talking for a while. Turns out she is a petty cool chick. It wasn't until two hours and a couple of drink later things suddenly changed.

"Alright, so how big is it?"

"'scuse me?"

"Couple hours ago you said you had a big dick and you said you were not a liar, so how big is it."

I could tell the alcohol had gotten to her, and she wasn't going to let this go, so I told the truth, "At my best, a little over ten inches."

"Bullshit"

"No bull."

"Prove it."

Looking around the room making sure no one watching , I took MEW's hand and placed it on the crotch of my pants. She bit her lip and arched her eyebrows in surprise as she gave it a few squeezes.

"Nope. Still not convinced." She said as she took her hand away. "I've met guys who've stuffed before."

"Alright well I'm not going to whip it out right here" I said as I again scanned the room before unzipping my fly. "But if you need more proof, reach in and grab it for yourself." And she did just that. Snaking her hand inside my pants she took a full grasp of it.

"Oh wow." She said in surprise "I guess you were being truthful.". She gave me a few strokes before pulling hand back. "Well, today is your lucky day."

"How's that?"

"I just about never cheat on my husband, but…" She downed the rest of her drink "I'm alone, a little drunk, kind of horny, and I haven't had sex in two months, so lets go." She said standing up and pulling me by the arm to follow her. We had almost made it out without interruption when I suddenly heard.

"Eddie!" I turned and looked, it was Hailee Steinfeld coming right towards. "Hey," she said as she gave me a quick hug, "You're not leaving are you?"

"Yeah I am."

"That's too bad I was hoping we could catch up. I hadn't seen you since I left Liv's party early." The way her eyes lit up at the mention of Liv' party it was easy to tell she knew what happened after she left. "Anything I can do to make you stay longer?"

"Sorry, but we really need to be heading out," I said indicating towards Mary Elizabeth who was trying hard to look annoyed.

"Oh okay" Hailee said taking her first glance towards Mary, it then clicked in Hailee's mind what I had meant "OOHHH Okay! Well that's too bad…." she said before leaning in to give me another hug. While embraced in the hug she whispered in my ear "… I was hoping tonight I'd get a taste of what you gave Liv" She then gave my ear lop a quick lick and walked off.

Me and Mary got to a car and headed to my hotel. In the car she said that she had thought for a second I was going to ditch her for Hailee, I reassured her I wouldn't have a pulled her in for a kiss. Had Hailee pushed me harder, however, I probably would have. We continued to make out as we moved from the car to the elevator. Once we got to my room I opened the door and let Mary in. It was a nice room, but still just a standard one queen size bed room.





"I'm little surprise a guy who just got rich overnight like you did didn't go all out for a suite." She said as she walked to the middle of the room.

"Last minute booking." I said as I watched her unzip the back of her dress and easily slip it off, leaving just in heels and a skimpy black lace thong.

"I guess that really was you nude in Fargo"

"I may not be willing to go full frontal on camera, but what's the point of doing all those squats if you can't show off every now and then." She said teasingly as she bent over and slid her thong off. I walked up and bent her over a bit more before dropping to my knees and burying my tongue into her vagina.

"Oh wow!" she gasped "Usually you have to have some serious star power just to get a producer to go down on you without at least giving him a blowjob first."

I replaced my tongue with 2 fingers before replying, "Like I said, I'm not like those other producers." Then I went back to eating her out. While she kept it all closely cut and well maintained Mary Elizabeth Winstead was the first woman in a while that I had gone on that actually had more hair down there than just a landing strip. I soon had her flipped over on her back. She pulled on her breast and nipples as her legs locked around my head, keeping it shoved against her pussy.

"Uuugghhh gawd. I can't remember the last time someone went down on me like this." It took a few more minutes but I did finally get her to orgasm. When her legs finally loosened their grip around my head I stood up and striped out my clothes. When I was down to my pants and boxers MEW sat up and moved my hands out of the way. Undoing the fly and pulling my pants and boxers down simultaneously, my rock hard dick then sprang up, just centimeters away from hitting her in the face.

"You really were not lying about having a big dick." She said while playing with it in her hands and looking at I from all angles. " You deserve a reward for your honesty." And with that she swallowed half of me on her first attempt and then started sucking. She worked half my cock in and out of her mouth while stroking the other half with her two hands. Occasionally popping it out of her mouth to kissing up and down the side of the shaft, or flick her tongue up under the head, and once to drop down to such each ball into her mouth, all the while doing her best to keep eye contact with me.

She pulled me out of her mouth and spat on my dick. "I hate to cut this short, but I gotta feel this thing inside me." She told me as she stroked me,

"That's fine, turn around and bend over." I ordered.

"Two rules before we do this, you can't cum inside me and you can't fuck my ass. Only my husband can do that stuff." I quickly agreed, and she got into doggy position. I rubbed my length along her slit a few times before slowly easing the head into her.

"Oh wow, I feel like I'm back in high school again" As I fed more and more into her she continued to moan. "Jesus you feel huge." Once I bottomed out I pulled back and staretd giving some slow shallow thrust building up the speed. "Oh yeah come on really give it to me." Having been given the ok to turn it up, I gave her ass are hard slap and pulled out to just about the tip before slamming it back in "Fuck Yes! That's It!" She cried out as I pumped the intensity. I reached down to tug on her nipples as she had done to herself earlier and to play with clit. I managed to make her cum twice before I pulled out and shot my load along her ass and back.

"Fuck that was good, I needed that." Mary said as she dropped down to her side in front of me. I was still hard and ready for round two, and with us in the spooning position I lifted her leg and got into place.

"Who said it's over?" I whispered into her ear as I slid back into her. She quickly turned her head to face me.

"Oh wow, really!?!"

"Really." I said as I pulled her head in for a deep passionate kiss as I continued to pump into her.

"Oh wow" she said as I broke off the kiss. "Gawd, if any of those other producers could've fucked like this I would have fuck them for a lot more rolls."

I flung her onto her back and put her legs over my shoulders. She had relatively small breast, but I didn't care as bent over in to take each of her light pinkish nipples into my mouth, not coming back up so until she was close to another orgasm. I watched her face explode in pleasure and her pussy grip my cock harder as she came.

"Fuck Mary, I'm gonna cum. I want you to swallow my load. She simply nodded and when I pulled out she sat up and stuffed my cock down her throat. "Look up at me." Seeing Mary Elizabeth Winstead look up at me with those big brown eyes and by cock buried down her throat was just what I needed to set me off. I quickly exploded in her mouth and she swallowed most of my load and sucked me for a few minutes afterwards as if to make sure there was nothing left.


We both passed out not too long after that. I got up an hour or so later to go the bathroom and get a sip of water. Walking back to the bed I looked over Mary's nude body on top of the sheet. It was then that the devil on my shoulder got the best of me and I snapped off a few nude pics of the actress with my phone before getting back in bed and going to sleep. My phone was starting to turn into a gold mine for hackers if they ever wanted another sequel to "The Fappening."

I was having a great dream where Hailee Steinfeld was riding my dick, but I slowly began being sucked out of the dream. I could feel the bed rocking. My morning wood felt hot and wet. I could hear moaning. I could feel something sliding up and down my dick. Finally I opened my eyes to see a happy and naked Mary Elizabeth Winstaed looking back at me as she rode my dick. "Sorry to wake you" she apologized "have an interview during breakfast today, and I couldn't leave before feeling this thing in me one more time."

"Trust me," I said as I gripped her hips and stared matching her stroke for stroke, "I don't care if you have to break into my house, if you ever feel like waking me up in this way again you're more than welcome." Mary smiled at my comment and soon she was really picking up the tempo. "Mary … I'm… gonna…cum soon"

"Just a little bit longer…I swear…I'm almost there…almost there" She was now bouncing on me like a car piston going as fast and as hard as she could.

"If you don't get off now I'm gonna cum!"

"Then do it! …I'm too close…fucking cum in me" With that, I did. I shot my load off into Ramona Flowers and within milliseconds she was having an orgasm of her own. Once it was over and she had caught her breath, Mary was quick to gather her things. She scribbled her number on a pad of paper next to the bed so I could contact her about the movie when I got back to LA. She said she'd love to work with a talented director like Ryan and a honest producer like myself. Then, before heading out the door, saying that if it all works out, maybe I can be there to keep her occupied while waiting between scenes.