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Author Topic: Two Jens & a Guy (Jennifer Aniston & Jennifer Connelly)  (Read 2859 times)

MineCraft040521

Two Jens & a Guy (Jennifer Aniston & Jennifer Connelly)
« on: February 05, 2026, 10:15:11 PM »
Two Jens and a Guy
Starring: Jennifer Aniston & Jennifer Connelly
Tags: MF, MFF, Cons, Oral, Facial
DISCLAIMER: This story did not happen and is complete fiction. Not all facts will be 100% true to real life.




“How about him?” Jennifer Connelly asked her He’s Just Not That Into You co-star and fellow Jen, Jennifer Aniston.

“Ha, yeah right. I’m looking for a college senior, not a senior citizen,” Aniston said with a laugh, taking a sip of her martini.

“Gosh, Jen, when did you turn into such a cougar?” Connelly asked the other Jennifer.

“Ever since I found out how good young cock feels,” Aniston told her, letting out a hearty laugh that caught the attention of the young bartender.

“Can I get you ladies another set of drinks?” Michael, the bartender, asked the two older women, setting his hands on the edge of the counter.

“How about it, Jen, one more for the road?” Aniston asked her pale co-star.

“Sure, I guess so,” Connelly replied, smiling at the young bartender who smiled back.

Catching the eye gaze exchanged between her co-star and the bartender, Aniston cocked a smirk before turning to face the young man.

“Can I ask you a question?” Aniston asked Michael, eyeing up the tall twenty-one-year-old.

“Shoot,” Michael told the famous actress as he poured the ladies another set of drinks.

“Do you think I’m still attractive? I’m only asking since my friend here seems to think there’s a problem with me pursuing younger men,” Aniston told him, keeping her eyes locked firmly on his as she watched him think over what she said.

“Well, I see no reason why an older woman shouldn’t be able to go out with or sleep with a younger man. Plus, I doubt a beautiful woman like yourself, or your friend here, would have a problem finding someone to do that with,” Michael replied, taking an empty glass and polishing it with a rag as both Jennifers looked at each other before turning back toward the young man.

“It won’t be a problem at all as I think we’ve just found our guy, haven’t we, Jen?” Aniston said to her co-star, who seemed to no longer have a problem with older women pursuing younger men, as she was now checking out the barely-old-enough-to-drink bartender.

“I believe we have,” Connelly said, making eye contact with the young man who seemed to pick up on what the two cougars were implying.

“So, kid, where’s the best place for a couple of girls to have some…private time around here?” Aniston asked, taking a sip from her second drink as the young man cocked a grin.

“Well, the best place for that would be the ladies' room,” Michael told the ladies, who both couldn’t hide their grins.

“And where is that?” Aniston asked, taking another sip of her drink.

“Just back there, on the right,” Michael told the Jennifers as Connelly headed toward the restroom, while Aniston grabbed a $50 bill from her wallet and reached out to the young bartender.

“Wait a minute, and then come join us. We’ll be waiting for you,” Aniston purred, whispering in the bartender's ear as she handed him the bill.

Michael just smirked as Aniston slid off her stool and followed her co-star toward the bathroom, her pert ass looking incredible in a tight cocktail dress. He counted to sixty in his head before letting his coworker know he would be back in a bit, quickly heading for the bathrooms at the back of the bar.

Once there, he knocked on the ladies' room door, which was opened in seconds by Jennifer A. The dirty blonde cougar had a wicked grin on her face as she stood across from the younger man, her dress removed, leaving her in just a lacy bra and a matching pair of panties.

“Welcome, handsome,” Jennifer said, giggling as she grabbed Michael by his shirt collar and pulled him inside, shutting the ladies' room door behind her.

“Long time no see,” Jennifer C. said, smiling at the young bartender over her shoulder as she slung her dress over one of the bathroom stalls.

“Guess I should probably start undressing too,” Michael said as he began unbuttoning his shirt, making quick work of removing it as the two cougars admired his young, muscular body.

“Mmmmm, I see we chose a good one,” Jennifer A. told her friend, biting her lip as her co-star similarly admired Michael as he undressed.

“You two ain’t so bad yourselves,” Michael said back, smirking as he unzipped his pants and slid them down his legs, slipping off his shoes quickly so he could get them off.

“Nice to know we still got it,” Jennifer C. said as she reached behind her back and unclasped her bra, as did Jennifer A., both ladies revealing their small, perky breasts.

Once Michael had his socks off as well, leaving him in just his boxers, he took a second to admire the slim figures of the two sexy older women standing before him. Even though some men would’ve preferred they had some more thickness on them, Michael could feel the blood rushing to his dick as he looked at their A-cup breasts and flat stomachs.

“Now, we really know we’ve still got it,” Jennifer A. said, laughing along with her fellow Jen.

As Michael slid his fingers into his boxers, the two sexy cougars did the same with their panties, all three half-naked people in the room sliding down their last garment of clothing in a flash, as if it had been a race to see who could undress first.

“Whoa!”

“That thing is fucking huge!”

Both Jennifers exclaimed in surprise as they took in the sight of Michael’s huge dick, which was hard as a rock and already throbbing. The two older women couldn’t believe just how big the twenty-one-year-old was, so much so that they couldn’t resist stepping forward and grabbing hold of his massive member.

“I can barely wrap my fingers around it!” Jennifer C. said with glee, laughing to herself as she jerked off the bottom half of Michael’s prick.

“I know, this thing is a beast,” Jennifer A. added, similarly unable to wrap her slim fingers around the young man’s cock as she worked the top half of it.

As they both crouched down, Connelly leaned in and wrapped her lips around Michael’s crown while Aniston went for his balls, taking a swinging nut into her mouth and sucking on it.

“Damn, you two ladies done this before?” Michael asked the fine older women, though they seemed to be a bit too busy using their mouths on his cock and balls to respond.

The young man quickly forgot what he’d asked as Connelly slid more of his dick into her mouth, her tight throat feeling incredible on his dong, while Aniston sloppily licked and sucked on his nuts.

Pulling up and off his prick with a *POP* sound, Connelly smiled up at the twenty-one-year-old while Aniston continued her oral assault on his testicles, clearly having not gotten her fix of them yet.

“No, but if you’re good, maybe the three of us can do this again. Somewhere a little nicer, probably,” Connelly said, standing up and stepping over to the wall and leaning back against it, her right hand moving to play with her pussy as she watched Aniston move from sucking Michael’s balls to his cock.

Michael groaned as Aniston slid over half of his dick into her mouth on the first gulp, the sexy cougar seemingly unfazed by the sheer amount of man meat filling her throat. Her hand slid up to work the few inches that her mouth hadn’t engulfed yet, all while Connelly toyed with herself and moaned from across the restroom.

“Fuck, you two are some damn good cocksuckers,” Michael grunted, feeling his dick throb in the back of Aniston’s throat as she sucked him off.

“We older women always are,” Connelly cooed from her place against the wall, clearly getting off on watching her co-star blow the young bartender they’d only just met.

Popping his prick from her mouth, Aniston gave it a few sloppy kisses, smearing saliva all over Michael’s prick before looking up at the young man and grinning.

“You ready to fuck us now?” Aniston bluntly asked, using Michael’s hand to assist her in standing up from the floor.

“Absolutely!” Michael exclaimed, taking the thin cougar’s hips in his hands and lifting her into the air easily, before positioning her cunt just above his thick, throbbing prick.

“Oh my GOD!!” Aniston cried out as Michael slid her down his meatstick, feeling the cougar’s tight cunt grip his cock like a second skin.

Connelly watched with a grin, moaning as they played with herself to the incredible sight of Aniston being bounced on this young guy’s huge cock. Neither woman could believe what Michael was able to do, but they both seemed to be greatly enjoying it.

“Fuck yes! Fuck me with that big dick!” Aniston yelled, not caring whether the people in the bar could hear her or not, as she enjoyed the feeling of this young guy’s dick stretching out her cougar cunt.

As she watched her co-star bounce atop Michael’s thick cock, Connelly bit down on her bottom lip to prevent herself from loudly moaning as she rapidly approached an orgasm. Her body shivered and shook as she played with herself, all while Aniston had her pussy relentlessly pounded by the young man holding her.

“Fill me with that big cock, you goddamn stud!” Aniston shrieked, her perky breasts bouncing against Michael’s muscular chest as she was given the most unbelievable fuck of her life.

“Shit, your pussy is so damn tight,” Michael grunted, his grip on the thin cougar’s waist tightening as his dick pulsed, letting Aniston know that he was enjoying this as much as she was.

“You fucking bet it is!” Aniston purred, looking into the young man’s eyes and smirking before smashing her lips against his while he fucked her.

“Oh my gosh, you guys,” Connelly moaned from across the room, doing her best to keep them muffled.

Breaking away from the twenty-one-year-old bouncing her lithe body on his cock, Aniston turned toward her co-star and grinned as she watched Connelly start to cum.

“I think she could use some time with this cock,” Aniston said, breathing heavily as Michael lifted her off his prick. The young man headed over toward the paler of the two starlets, his hard dick aiming directly at her.

While she continued rubbing herself, Connelly felt Michael grab her waist and spin her around, pushing her thin frame against the cold wall of the restroom. As she did her best to continue playing with herself, Michael aimed his stiff prick at her slit and forced himself in, splitting the MILF’s tight cunt in two.

“OHHHH MY GOODDD!” Connelly cried out, bringing a hand up to cover her mouth as Michael began to furiously fuck her against the bathroom wall.

The coldness of it made her nipples harden as she was mercilessly pounded, the young man slamming himself against Connelly’s pale, pert ass. Her cheeks clapped as she felt her pussy stretch to accept the girthy prick being repeatedly forced inside her.

Next to Connelly and Michael stood Aniston, the tanner of the two cougars, happily playing with herself as she watched her co-star get fucked even harder than she did. The 39-year-old actress pinched one of her hard nipples as she enjoyed the show being put on in front of her.

“Keep on fucking her! Make her cum all over that cock!” Aniston cheered on from the sidelines, moaning as she similarly approached orgasm like her 38-year-old co-star was.

“Almost…there…” Connelly cooed, her previously pale ass slowly becoming red due to the roughness with which Michael was fucking her.

“Make her cum, then make me cum, then we’ll make you cum,” Aniston whispered into Michael’s ear, rubbing her tan, lithe body against the muscular, young man as he continued to abuse Connelly’s cunt with his cock.

“You gonna cum on this dick?” Michael asked Connelly, reaching out and grabbing a handful of the raven-haired beauty’s hair, eliciting a moan from her.

“Yes! Yes! So close!” She answered while continuing to molest her clit with her hand, all while Michael’s cock slammed itself over and over again inside of her.

“Good, cause I wanna cover both of your faces,” Michael grunted, feeling his balls churn as he fucked Connelly, signaling that he may not be able to make them both cum before he did.

While still thrusting his hips, Michael looked to his right and eyed Aniston, who was still watching her co-star receive the rough, relentless pounding from the handsome, young man. An idea popped into his head, and Michael immediately acted on it, removing one of his hands from Connelly’s thin waist and bringing it to Aniston’s slit. With two of his fingers, he invaded the older woman’s cunt and began to furiously finger-fuck her.

“Oooooooh yeeessssss,” Aniston cooed, both of her hands shooting up to toy with her nipples as Michael pleasured her with his fingers.

Meanwhile, Connelly could barely think as she rapidly approached her climax, her cunt feeling like it was on fire due to the harshness with which Michael was fucking her. She couldn’t believe he hadn’t tired himself out yet, and that was without her even knowing that he was simultaneously pleasuring her friend.

“Gonna cum! Gonna cum!” Connelly finally cried out, one of her hands slamming against the wall of the bathroom as she came, her pussy clamping down on Michael’s prick and nearly making him spill his load inside her.

As Connelly went through the motions of her climax, Aniston started to do the same, her cunt squeezing Michael’s pointer and middle fingers while she climaxed. Even though he was close to blowing his own load, Michael didn’t stop moving as both MILFs came, his hips and fingers continuing to move as they finally finished.

“Fuck, both of you, on your knees,” Michael grunted, sliding himself out of Connelly’s cunt and fisting his hard dick, which felt like it would explode any second.

Both older women got down on their knees, neither of them caring about how dirty the floor was as they stuck out their tongues expectantly. They were quickly greeted by the feeling of Michael's hot, sticky load splattering across their faces, each of them getting about half a dozen ropes.

The young man furiously stroked himself as he came, letting out a throaty grunt while he painted both of the MILFs on their knees before him. Once he was finally done drenching them in his seed, he let go of his prick and admired the work he had done on the two A-list actresses.

“Holy shit, kid! You fucking drenched us!” Aniston said with a laugh, one of her eyes glued shut with the young man’s cum.

“Jen, where are you! I can’t see!” Connelly joked, causing both girls to break out into laughter.

Michael just smirked as he watched the two ladies start to clean themselves of his load, with Aniston even leaning in to lick some of it off Connelly’s face.

“Damn, you two are something else,” Michael told them, chuckling to himself as he walked over toward his discarded clothes.

“You were no slouch either, kid. We’ll have to come back here tomorrow night for round two, but I think it’ll be better if we do it at one of our places,” Connelly said, eyeing the half-dressed bartender while sucking one of her fingers clean of jizz.

“Maybe I’ll ask Drew and Scarlett if they want to come join us,” Aniston added, looking up at the young man who quickly looked back at her after hearing what she said.

“Damn, I don’t know if I can handle four of you,” Michael admitted as he finished redressing.

“Don’t worry, kid, I think you’ll do just fine,” Aniston told him as she and Connelly turned toward each other and chuckled.
 
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