Jennifer Aniston Buys Some Cock

Story Info
Jen nails a 'hugely' talented young hustler.
2.1k words
3.45
104k
15
0
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
mef
mef
30 Followers

19 year old Raoul slowly walked along the beach. As usual, many pairs of female eyes, of various ages and levels of boldness, scanned his six feet four frame - sliding over pecs, tracing the shape of the long thick pecker that bounced in its pouch, or guessing the weight of the big balls that hung below. The eyes flipped to the retreating back as they drank in the fabulous, hard cheeks, barely covered by the speedo. By the end of the exercise there were hard nipples and wet vaginas all round. The older ladies planned assignations with husbands or boyfriends or pre-dinner vibrator sessions, while the teenagers wondered whether it would be possible to find somewhere away from Mom and Dad for the second, third or forth pussy-spanking session of the day.

Raoul was used to his physical attributes getting such attention. Even in his senior year of High School he was a mouthwatering prospect for the local ladies who enjoyed the-ahem- younger man. His brains were less impressive, though, and Ds had been all he could hope for from his classes. However more than one female teacher was impressed enough with them [once he turned 18, of course!] to attempt to suck them out through the already hugely fat head of his penis.

It was pretty clear that the penis in question was going to be his salvation, when, after hitting the beach after graduation, he was offered money by middle-aged, wealthy women just to see, touch or suck it. He hadn't been able to afford a new speedo, so had to make do with last summer's; unfortunately (or fortunately) it had a great deal of difficulty coping with his still growing package. He was embarrassed at first by the stares and lewd comments but soon began to enjoy them and the ever-ready money. At the end of the first week a Japanese woman on vacation with her older, tiny husband had offered him two hundred dollars for a ride after having been primed with a few adjacent workouts and sunbathing sessions. Her husband safely at the casino, she took him back to her hotel room and fucked his ass off. He'd never forget the glazed eyes, and tongue lolling from the pale and delicate face as she cursed in Japanese while bouncing up and down on his pole like a maniac, as she got to live out one of her favorite jerk-off fantasies.

It wasn't just older women who propositioned him or who responded positively to his tactful offers. Overweight and plain younger vacationers found out that they could get their hands on some primo dick at the beach providing they were willing to pay. The sort of meat they hadn't a prayer of scoring at home. They gazed in awe at the kind of penis they'd never observed except on a computer screen with their panties round their ankles, proudly taking cell-phone photos to send to their girls back home.

-------

Raoul reached the Beachside coffee house, sauntering inside to buy a soda, ignoring yet more female stares (and a few male ones). As he stood sipping carefully, a girl of about 18 with beautiful, almost blue-black skin came up to him.

"Hey, Raoul. How's it goin' man?"

"Hey Tonisha. What's up?"

"Nothing much, just checking out the pussy. There's some fine pieces of ass on the beach today. My clit's been drillin a hole all morning."

"Go get some, Playa!"

"What about you, man?"

"Yeah. Thought I'd hang loose, see if a lady wants to buy a ride. I'm broke, man."

As Tonisha drifted towards the pool tables Raoul spotted a lady in her mid-thirties who was doing a pretty poor job of pretending she wasn't checking him out. She wore a black wig and a pretty expensive pair of shades and was obviously rich from the way she was dressed. Immediately Raoul went into hustler mode, starting with a slow re-adjustment of his package - not too obvious, but maybe enough to get the lady's clit jumpin'. A few muscle flexes followed, including the most important one which resulted in his slightly engorged cock make an obvious move in its pouch. The lady's tongue peeked out a nervously swept dry lips. Score! Either she'd come over and buy some dick; flirt and leave; or just keep watching - storing away the memory of the fat package and superb musculature for the next time her 'reel-feel' vibrator was pumping between the other lips, already staining her expensive silk panties.

------------

Jennifer Aniston was bored, tired and horny. The brilliant idea of travelling on vacation in disguise had one drawback: she couldn't move about as freely as usual without her entourage to fend off annoying fans and curious bystanders....and most importantly in her current single status, they couldn't provide her with the sexual relief that she required when needed. Her current bodyguard Steve had been selected for his physique in more ways than one. The job was his when she gratefully slid her vaginal lips down the huge piece of meat always visible in the tight jeans he wore to the interview.

Although she had spent the early hours of the morning humping two fingers while watching pay-per-view gay porn in her hotel room [beautiful guys doing nasty things - she'd loved gay porn since she'd discovered a cousin's stash as a teenager], she was still in dire need of relief when she spotted a truly memorable piece of young ass come into the cafe. In fact he looked like one of the 'actors' she had recently spanked off to. After talking to a young girl who she'd earlier caught ogling her famously large nipples as they poked through her top, he gave her a subtle but effective show of his goodies; her clit began to slide from its hood as the flexing began.

It was pretty clear that the kid was a hustler, and her pussy gaped and smacked at the fantasy of making use of his services. She couldn't of course, far too dangerous....but as he turned around, giving her a view of the spectacular ass, she found her pussy was working hard to convince the logical part of her mind otherwise.

Safety or pleasure? Cock or a career? She swallowed and crossed her legs, squeezing tight.

Raoul watched her get up out of the corner of his eye and slowly make her way over. He could see her large nipples were obviously erect and guessed there was quite a commotion going on in her panties as her clit lead her over towards him.

"Hey there. Can I buy you a drink?" She said in a strangely familiar voice.

"Just a diet coke thanks."

"So, what do you do around here?"

Make rich, white ladies scream all night. As if you didn't know.

"Odd jobs, I guess. Anything anyone is willing to pay me for."

Raoul flexed once again and the fat salami in his pants moved just a fraction. The lady's head tilted down, her eyes invisible behind the shades - but he knew where she was looking. His left hand moved slowly down and pulled at the pouch slightly, allowing the cock to lengthen further.

The lady's tongue peeked out and made a quick brush over dry lips.

"How much?"

"Two hundred. You suck me, one hundred; I suck you, one fifty. If you want me to jerk off while you jerk off watching -that's eighty."

They usually went for the full-on fuck. At this point there cunts were doing all their thinking....

"Penthouse at the Royal Empire."

She began to scuttle away before he grabbed her arm.

"Money first, lady."

She pulled out the notes after making sure no-one was watching.

--------

Fuck! The Penthouse. This lady was loaded. Raoul had visions of being a kept dick. Money, clothes and cars in exchange for cock. He'd heard about that sweet deal from other young guys at the beach. He looked at the clock on the wall. 15 minutes to allow her to get settled and get her hands on that bubbling pussy. But not too long or an orgasm might clear her head and give her second thoughts. 10 minutes, maybe.

-------

Raoul sauntered along the corridor to the suite, closely observed by two Puerto Rican maids with their tongues hanging out.

"Maria, Look at the ass on that kid." "What's he doing here?" "What do you think. The rich lady must be sick of the pornos. heh heh!"

29 year old Carmen had enjoyed making use of the remaining rent-time of the pay-per-view porn the lady ordered when she cleaned the suite in the morning - wiping her sticky fingers on the carpet before pulling up her panties. Raoul had noticed their interest and decided to tease them a little. Just as he was about to knock on the door he turned in their direction and dragged out his meat, waiving it at them and wiggling his tongue lewdly.

The maids stared with open mouths as he was let into the suite [after re-adjusting his clothing] through the slightly parted door.

"Shit, what a fucking pervert." "Yeah I think we should call the police."

They stood rooted to the spot in silence - apart from the soft sound of two thickly haired vaginas spraying cheap cotton panties.

---------

Jennifer had tried hard not to masturbate when she returned to the hotel. Thinking about the risky and forbidden thing she was about to do as well as the rock-hard piece of ass on his way up to the room made that difficult. Difficult as finding out that your husband was fucking a slut with weird, deformed lips...well, almost.

Maybe he would just run off with the money....Stupid, stupid, Jen. "Oh fuck, you've done it again," she said to her vagina.

A soft knock on the door. Shit. Oh yeahh!. She grinned, got up and then panicked. If he recognizes me....

Spotting her shades on the vanity she put them on and then...yes! A loosely fitting robe with a hood. Removing her panties...she was ready.

"Hi Ma'am, I'm here to fix your leaking faucet." "Cute. Come in."

She sat down in a white wicker chair near the bed and tried to appear calm and in control.

"Okay, kid. Strip. Show me what I'm paying for."

He slowly peeled off his t-shirt revealing a huge and fabulously muscled frame. He looked as if he had been put together by a committee of sex-starved housewives.

Jennifer groaned softly and felt a small squirt of liquid escape her pussy lips. He teasingly lowered his shorts to reveal a pair of briefs that cupped his huge package lovingly while showing clearly the outline of the huge balls and fat meat.

"Why don't you come over and take these off for me?"

She'd intended to be the one giving the orders, but before her brain clicked into hormone-soaked gear she found herself on her knees in front of him, pulling off the wonderful piece of cloth.

"You can keep those."

Raoul once spied on his auntie sniffing the man smell from a pair of his used jocks with a hand down the front of her jeans, and so wasn't surprised when he noticed his clients surreptitiously slipping his underwear into their pockets.

She spent some time tracing her small, beautifully manicured hand over the abs and delts, probing and squeezing; moving around to feel the back muscles and then....the awesome glutes. Oh fuck, what a pair of cheeks on this kid! High and hard. This must have caused several hundred wide-ons already and he's hardly out of High School.

"Over on the bed. Lie down."

Her commanding tone was undermined by a lustful shaking in her voice. She knelt over his thick thighs rubbing and squeezing the fabulous muscles before moving up to the huge slab of manmeat, already half hard. She took it lovingly in her hands and with a few soft strokes brought it to full erection. Holy fuck! It must be 10 inches! This kid could be a pornstar. She stared down in awe at the fat helmet, scarlet with a large slit already oozing its liquids.

She'd intended to take it slower but her pussy was begging to rap its lips round the awesome thing. She raised her hips and guided the head to the gaping hole.

"Fuuuuahhhhhhhhhh"

She groaned as the head popped inside. Her eyes rolled into the back of her head as she gratefully slid down the enormous length. She quickly got into rhythm.

"Fuuu shhhit fuuuck shhhiiii fuckkkk shiittt ooohhh fuccckkk shiiitttt yeeeaah fuuuu shiiit"

"AAAAhhhhhhhhhhhh"

After only two minutes she shook with the beginnings of a huge orgasm. Her head went forward then back then forward again; her hood fell away and her shades went flying. Raoul looked up into the lust-sweaty face of.....Jennifer Aniston!! Her mouth grimacing as her vaginal muscles squeezed -released-squeezed his meat in furious passion.

mef
mef
30 Followers
Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Jessica Alba: Porn Star Miss Alba stars in a little movie for her private collection.in Celebrities & Fan Fiction
Guarding Jennifer Aniston A wounded bodyguard gets his payment in love.in Celebrities & Fan Fiction
Black Widow Roleplay Scarlet Johansson has some roleplay fun with a lucky hunk.in Celebrities & Fan Fiction
Bang Up Job Big Bang's Melissa Rauch feels naughty after Maxim shoot.in Celebrities & Fan Fiction
Big Bang Birthday Kaley Cuoco, Melissa Rauch both give a special birthday gift.in Celebrities & Fan Fiction
More Stories