Sex For Drugs Ch. 08

Story Info
Jennifer Aniston has anal sex for Jolie's sex tape.
7.1k words
4.61
89.4k
34

Part 8 of the 11 part series

Updated 11/01/2022
Created 05/10/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

For those of you who clicked on this story just cause you see Jennifer Aniston's name and you don't read the series, than scroll down to the stars. Everything before the stars is building up characters for the series. Jebbifer makes an appearance after the stars. I hope you all enjoy.

_________________________

I pulled up in front of the club, I had spent most of yesterday sleeping after my strange, yet wonderful encounter with Elisha Cuthbert. After she had kicked me out, in the nicest way possible, I went home to find Melissa passed out on the couch, with a needle on the table. So to say, she had managed to stay clean for just about a week. I was now starting to get worried and decided I was gonna do something about it. But first, Melissa needed to be conscious and sober so that everything would actually sink into her head.

I tossed my keys to Earl, the valet. I saw Travis and the new guy, Jeff at the door. It looked like we had a good turn out tonight, the queue to get in was pretty long. I said 'Hi' to Travis and walked in. I walked up to the bar to the one and only spare seat.

"A beer, thanks." I said to the bartender. I couldn't even remember her name, we had a lot of people working for us and a lot were uncomfortable with the 'extra activity' that we had and would leave when they found out. She handed me a bottle of beer with the cap taken off but still at the top. I took a sip and looked at the guy sitting beside me. He looked quite depressed.

"What's troubling you buddy?" I asked, not really bothered about his answer, looking around, scanning the place to see if I could see Stefan anywhere.

"Last summer, when my girlfriend was in New Zealand shooting a movie, I flew out there and proposed to her, she said yes." He said, his words slightly slurred.

"And that's the problem? You have to take her down the aisle?"

"No! On TV, I said I wasn't in a rush to get married and last Christmas, she called it off. Just like that." He attempted to click his fingers a couple of times before he finally managed it. "She said... we were on a break. But I know she's fucking someone else. Some hockey player for the Kings."

"You said, you said something on TV to piss her off. You a singer?" I asked not sure at all on who he was.

"No. I'm Justin Timberlake's PA."

"The guy who dated Elisha Cuthbert?"

"Yeah!" He replied. Elisha's dating a hockey player? I thought we were an item, sort of. It didn't really matter, I cheated on her two days ago and had three women living at my home as live in girlfriends. But it still bugged me. I just walked off, I think he was still talking, but he was too drunk to even notice I wasn't there.

I heard someone yelling as they came into the club. I looked over to see that it was that singer 'Pink.' She annoyed the shit out of me and I made my way to the back. I walked into the office to see Stefan drooling over Pink on one of the monitors.

"Dude!" I said throwing the cap of the beer bottle at him. "Why'd you leave me a message to meet you here?"

"Oh! Shit! Yeah!" He said handing me a disc. "It's done."

"What is it?"

"The Angelina Jolie porno."

"That quick?"

"Yep! I even made chapters for easier navigation." He seemed proud of himself. I walked around the table to him, he stood up as he gave the disc to me.

"Thanks man." I said giving him the half hug, with one hand.

"No worries dogg!" Stefan said. I got my cell phone out and looked up Vince Vaughn's number. I called his home number. I didn't have Jennifer's number and I knew Vince was away filming, so Jennifer would definitely answer if she was in.

"Hello?" I heard Jennifer's voice.

"Hi. It's Kash."

"Did you do it?" She said cutting me off, sounding very excited.

"Yeah. When do you want me to get it to you?"

"Could you bring it over tonight?" She asked. It was kind of a stretch, but I had nothing else to do.

"Sure!" I replied. "I'll be there within a hour." I hung up.

"Dogg? Do you even have the address?" Stefan asked.

"Yep! I've been over to Vince's place a couple of time's." I answered. "Check you tomorrow." I said as I made my way to the door. The intercom buzzed.

"There's a Alecia Moore here to see you guys." Travis said.

"Send her in." Stefan replied.

"Who's Alecia Moore?" I asked.

"Pink."

"I better get out before she gets in." I said going out the door.

"Good luck!" I heard him yell. As I made my way back out to the main part of the club, I saw Pink starting to head back. At least he can drool over her in person now and maybe even get a piece of her, judging by what I've read in tabloid papers about her, I think he's gonna get lucky tonight. She was headed right towards me, I wanted to avoid her at all costs so I decided to take the back door out.

I closed the door behind me. The back door led out to a alley way, which looked dark and the kind that you could get killed in at night. I started to walk forward, down the alley when four guys came out of no where.

"Hey! Rich boy!" the tallest one said. "You work at this stuck up club?"

"Something like that." I replied staying calm.

"You know, we always get kicked out of here and now, we're not even allowed in. And you know what? It's your fault!"

"How you figure that?" I asked.

"He's talking back!" Another guy said, a short, stocky guy. "We ought to teach him some respect!" He said punching the palm of one hand with his other fist.

"So let me get this straight." I started. "You're getting ready to kick the shit out of me for no apparent reason other than I may or may not work here." I said breaking it down. "You have to forgive me for thinking that you guys aren't the brightest bunch I've ever come across." I finished what I was saying and tried to walk past them. One of them pushed me back, not letting me through. The tall guy slugged me one on the face pretty hard. That's when I realised, I was gonna have to fight these guys to get through.

"Yeah! Kick the shit out of him Ed!" another one of the guys shouted to the tall guy, who's obviously named Ed. Ed punched me one on the stomach dropping me to my knees. I was gonna get my ass kicked if I didn't do anything and I decided that seeing as though it was four on one, I was gonna have to fight a little dirty. That's when I used full power to throw an elbow. It wasn't my fault I was on my knees in front of Ed and that my elbow was in range of his balls. Need less to say, he dropped to the floor clutching his nuts.

The other three pounced on me like animals, the first guy kicked me over and then all three of them started to stomp me. I guess I won't be seeing Jennifer within the hour like how I had said. That's when I remembered, I kept a gun on the side of my right calf, another thing I had picked up from the gangster movies. It may be tiny, but when you pull the trigger, it has the same result as any gun when the bullet makes contact.

As I reached down to my ankle, all of a sudden one of the guys went flying across on to the wall. A guy had just flung him across and then he grabbed one of the other guys and gave a thundering punch to the stomach. By now I had pulled my gun out and smashed the fourth and final guy on the back of the head with the back of the gun. Once he was on the floor, I straddled him and continued to smash him across the face repeatedly with the back of the gun.

"Hey ease up buddy." The guy who had helped me said, helping me up to my feet. I looked at the guy and he looked very familiar. He was in a black suit, with a white shirt, top buttons undone and in black jeans. He had very short hair, just enough so he wasn't bold. I was still fuming at the four guys, I wanted to carry on pounding them.

"You OK?" The guy asked. I turned around and shot the guy I was pounding on and the guy that I had elbowed on the nuts.

"Much better now." I said putting the gun away, under my pants at the side of my calf. The guy looked a little shocked. "Thanks for the help. I'm Kash by the way." I said, extending my hand. He was staring at the guys I had just shot.

"Domonic." He said turning his gaze to me. "Why'd they attack you?"

"No reason, except for the fact that they're assholes." I replied.

"Fuckers like them deserve it." He said, now going back to normal.

"Hey!" I said realising how I recognised him. "Aren't you the guy of Prison Break?"

"Yeah."

"What you doing back here?"

"I was trying to get into the club, but they didn't let me in, saying that I was lying and that I wasn't a celebrity. I heard some noise at the back, came around to see you getting your ass kicked. So I did the good Samaritan thing."

"Thanks for that. Don't worry about getting into the club!" I said as we headed out the alleyand around to the front of the club. "Travis!" I called out as we got to the front of the line. "This is Domonic Purcell, from Prison Break, let him in and send out a clean up crew around the back in the alley."

"Thanks for that." Dominic said shaking my hand.

"Don't worry about it, but this doesn't make us even. I still owe you." He headed off into the club and I waited for Earl to bring my car around. I checked around to see if there was any blood on my clothes, luckily there wasn't any. Earl bought the car around, I got in and checked in the rear view mirror to see if there was any bruises or cuts on my face. I didn't seem to have any, probably be feeling the effects in the morning.

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

I took my time to get to Jennifer's, driving just under the speed limit, I didn't want to seem too eager to Jennifer. I pulled up into her drive way and parked. I walked up to the door and when I was about twenty feet away, the door opened and I saw Jennifer urging me to hurry up. She seemed like a excited kid on Christmas morning.

"Come in!" she said closing the door behind me. I checked her out and she was dressed in a white top, faded blue jeans and no shoes, she was barefoot. I took my shoes off, it was the courteous thing to do.

"Lead the way." I said. I followed her into the living room. She had a great ass, the one made famous on the cover of 'Rollingstones' and I couldn't take my eyes off them and those tight fitting jeans made them look incredible..

"Where's the tape?" She said with a huge smile on her face, holding her hands together just under her chin. I pulled the disc out of my pocket. "Ooh! Getting all hi tech on me." She said taking the disc from me. She put the disc into the DVD player, switched the TV on and sat down on the couch, her legs crossed like a yoga position.

"Sit!" Jennifer said patting the spot beside her. I sat down next to her. The DVD menu screen came up. "Very nice!" She said nodding in approval as she searched through the chapters.

"The chapters are named with what happens in them." I said, getting impressed at how much things that Stefan had added on in the short amount of time that he had to actually do it.

"Oh my God!" Jennifer said putting the remote down onto her thigh. "You fucked her up the ass?"

"Yeah." I replied casually. "One time she even had two dicks in her."

"No way!" She said with a shocked look on her face. "She did two guys?" I just nodded. She highlighted the chapter called 'Anal, doggy style.' It was when me and Stefan swapped positions and I jammed my cock up her ass. Jennifer got a shocked, excited look on her face, holding the remote up to her chin as she had her hands over her mouth.

"Oh my God! I almost feel bad for her, it looks like you're tearing her ass apart."

"She seemed to enjoy it."

"Pffft... she's got a dick in her! Of course the slut's going to enjoy it." She insulted Angelina. "This is so much better than I was expecting it to be." She said. "How much you want for it? Let me just go get my check book." She said getting up. I put my hand on her shoulder and pulled her back down.

"I'm not after money. Let's just say you owe me a favour."

"Really? You sure?" She asked. I nodded my head. "Oh! Thank you so much!" She said leaning forward hugging me. I hugged her back, pushing her close to me with one hand and using my other hand to squeeze her ass. "Are you groping my ass?" She asked looking a little confused.

"It's just that you have an incredible ass!" I replied. She smiled.

"You think I have a nice ass?" She said trying to look back at her own ass.

"Ever since I saw that bubble butt on the cover of Rollingstones." I replied.

"Maybe I could show you my bare butt as the favour I owe you." She said laughing.

"You would do that?" I asked.

"Sure!" She said in that high pitched squeal that we've heard a million times on 'Friends.' "You did my one huge favour!" She said stressing the word huge. "And the material is very, very, very, hardcore."

"Take your jeans off." I said. She stood up, turned around, giving me a cheeky smile and pulled her jeans down enough to show her ass. "Let me get a closer look." I said going right up to her and squatting down so her ass was a couple of inches in front of my face. I used my index finger to lower her jeans. Jennifer let go off her jeans, letting me lower them to get a better view of her ass.

"I did only say ass but I'll make an exception." She said. I spread her ass cheeks apart. "What are you doing?" She laughed, looking back.

"Getting a better look." I said as I saw her tiny little ass hole.

"OK!" She said bending over a little. "Better?"

"Yeah!" I replied. You have one tight little ass hole. You still an anal virgin?"

"No!" She squealed again. "I let guys fuck me up the ass on special occasions."

"It looks tight. I guess they must have small dicks." I said.

"Are you trying to say I only attract guys with small penises?"

"It's not your fault." I replied.

"So you're saying that girls ass holes get stretched out when you butt fuck them?"

"Yeah!"

"You must have a big penis." She said. I unzipped and took my cock out. Jennifer was still looking back.

"Look in between your legs." I told her.

"Why?"

"You showed me yours, I'm gonna show you mine."

"Oh my God! Look at the size of that thing!" Jennifer said looking down at my cock. I felt her warm hands on my shaft. She was stroking it and making it harder. "Oh my God! Look how much bigger it's getting!" She said sounding shocked. "If I ever took this up my ass, it would definitely stretch it out."

"It will."

"Don't you mean would?" Jennifer asked.

"No. Will." I said, licking her butt crack.

"Hey!" Jennifer said jumping forward, pulling her jeans up, getting annoyed. "I'm with Vince!"

"Than why were you stroking my cock?"

"I... I..." She thought for a second. "...Just wanted to... see how big it... would get. Hah!" She said, proud of her answer.

"Well..." I said. "You owe me a favour."

"I showed you my ass!" Jennifer said, going on the defensive.

"I got Angelina Jolie to come to my club, have sex with two people and managed to catch it on camera with different camera angles, turn it into a DVD, with chapters." Well, Stefan did most of the work.

"Wow!" She said quietly. "I guess showing my ass doesn't come nowhere near covering it. Does it?" She said with a thoughtful look on her face.

"I got an idea." I said. "Seeing your ass and you stroking my cock has got me a horny. So I need you to do me a favour."

"What's that?" She asked smiling.

"I need you to give me some relief."

"Sexual?" She said, getting serious.

"Well, you are the one who got me horny."

"I'm sorry!" She said biting her lower lip. "So if I help give you sexual relief, than you'll call it even?"

"Yeah." I said. "You give me relief with what got me all hard and you don't owe me anything."

"That should be easy." She said. "You want me to use lube?"

"If it'll help you." I said a little surprised at how she put up no resistance to getting ass fucked.

"I don't give a crap. You'll be the one getting friction." Shit! This was my kind of woman.

"Where do you wanna do it?" I asked.

"Here will be fine. It won't take long. I'll go so fast that you'll cum in seconds!" She laughed.

"I can hold back a lot longer when a woman's riding me than when I'm fucking them."

"Riding?" She said looking confused. "How can you ride a dick with my hand?" She asked. It made sense now! She thought she was gonna give me a hand job!

"I think you're a little confused." I walked up to her. I slapped her on the ass, holding on to her ass, giving it a hard squeeze.

"Oh!" She said realising what I meant, she didn't seem like the brightest of girls. "No! No! No! No!" She said realising what she had to do. "Uh-ah! No way! There's now way I'm taking that big thing up my ass! It won't even fit!" She protested. "And besides, you said you want me to give you relief with what got you hard and that's my hand!" She said showing me the hand she stroked my cock with. I moved her hand down.

"I already was hard when I got a close up of your ass, your hand just made it harder." I said. "But if you're not gonna do this 'favour' for me. Than I don't think you're good for any favours." I said putting my cock away. "I guess I should just take the disc and go."

"Noooooo!" She said holding my arm. "You can't take the disc! Here!" She pulled her jeans and panties down, let it drop to the floor and stepped out of them as she turned around and bent over. "Go on! Knock yourself out! Take as long or be as quick as you want. Just stick it in and bang away!" I don't know if she was being sarcastic or serious, but her ass was right there. I took my cock out and the pushed it in between her thick butt cheeks and squeezed the head in.

"OWWW!" Jennifer screamed jumping forward. "That hurt!" She said rubbing her ass hole. I couldn't help but laugh. "OK! We definitely need lube." She said walking past me. "Oh! Look!" She said picking up a tub of Vaseline. "Here!" She handed it to me. "You have a big cock. So use a lot. OK?" I said nothing. I quickly stripped off to nothing.

"Here!" I said handing the tub back to here. "I want you to strip off and then use the Vaseline on your ass hole." She smiled. I pushed the coffee table that was in front of the leather couch out the way and sat down.

"OK." She said, with that pissed off look that she has. She placed the tub on the coffee table and took her top off, pulling it over her head. She had no bra on underneath. Jennifer let out a little annoyed laugh. She pulled her jeans down and then let it drop to the floor. She had a black thong on which she reached for the waist band.

"Wait!" I said.

"What!" She gave an annoyed smile.

"Come over here." I said. She made her way over to me and stood right in front of me. "I want you to bend over the table, stick your ass out and slowly pull your thong down."

"OK!" She said bending over the coffee table, her knees on the floor, her tits pressing down on to the coffee table. She reached back with both hands, held her thong by the waist band and slowly pulled her thong down, revealing her round ass to me once again.

"You like that? Huh?" Jennifer said smiling at me. She seemed to have lost that temporary pissed off tone that she had the past minute or so. She opened the tub, scooped some Vaseline out with her index finger and rubbed the Vaseline on her ass hole. She slowly pushed her finger into her ass, with a loud squelching sound. She slowly worked her finger in and out of her ass hole, getting the Vaseline all around the inside of her ass hole.

"You like that? Watching me stretch out my ass hole with my finger so you can pound me straight away." She said, looking back at me. I scooped some Vaseline out and started to rub it onto my cock, stroking the Vaseline onto my cock, getting it well lubricated so that it will slip in easily.

Jennifer carried on fingering her ass hole as I stroked my member. I went on to the floor, on my knees, taking position behind her, my back leaning against the couch.

12