Meeting Jennifer Aniston

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Title: Meeting Jennifer Aniston

Author: RandyPan

Celebs: Jennifer Aniston

Codes: Ff, oral, anal, mas, ws, cons

Disclaimer: This is fiction, it did NOT happen. Fantasy is legal.

Also, if you like this story, email me at [email protected]

Note: This story was a request.

Caroline was a huge fan of Jennifer Aniston.  She’d seen Horrible Bosses over a dozen times, and even had every season of Friends on DVD.  A friend of hers’ Dad worked at a hotel, where she heard Jennifer was going to be staying, so Caroline became determined to meet her.

“Just…steal me a maid’s uniform, and get me in there.  You know my size.”

Soon, the day came, and, before she knew it, Caroline was on her way to Jennifer’s room with a stack of towels.  Meanwhile, Jennifer was coming out of the shower.  As she walked around the room, naked and still steaming, there was a knock on the door.


“Hi, I’m from housekeeping.  I have your towels.”

“Oh, okay, come in.” The door opened, and Caroline came through.

“Oh, Jesus!” Caroline looked away. “Sorry, I didn’t know you were, uh…”

“Oh, relax!  You have the internet, don’t you?  I’m sure you’ve already seen this.” Caroline had indeed seen it, and even touched herself to it, particularly the scene in Horrible Bosses where she’s naked under her open lab coat.  But seeing it in person?  Caroline looked, and Jennifer was cupping her boobs with her hands.  Jennifer then smiled, and started rubbing her tits. “Hey, what’s your name?”

“Uh, Caroline.”

“Caroline.  You’re kind of cute, you know that, Caroline?”

“Um, thanks?” This…was getting surreal.

“I hope you don’t mind me asking, Caroline, but how old are you?”

“Um, sixteen.” Caroline was a little too dumbstruck by the situation to lie.

“Sixteen…” Jennifer narrowed her eyes at the ceiling. “Is that legal here?” She then looked back down at Caroline. “You know what?  Doesn’t matter.  I’m sure you can keep a secret, right?”

Without waiting for an answer, Jennifer walked over, placed her hand under Caroline’s chin, and gave her a long kiss.  Caroline could feel her heart pounding, her nipples hardening, and her pussy getting wet, as Jennifer’s tongue wrestled with hers.

Eventually, but feeling too soon, Jennifer broke the kiss, and said, “Why don’t you take that uniform off?”

“Um, you want me to…”

Sitting down on the bed, Jennifer said, “Yeah, let’s see ya, honey.”

Caroline’s heart was threatening to burst out of her chest, as she started to unbutton her jacket.  Soon, she was standing in her black bra and panties, while Jennifer looked her up and down, with a weird smile on her face.

“Nice.  Could you…take those off, too?”

“Um, okay…” Caroline felt hot and light-headed, as she reached behind her back, unhooked her bra, and took it off, then grabbed the sides of her panties, and pulled them down.

Jennifer was now licking her lips, and rubbing her thighs.  Finally, she spoke. “Caroline?”


“Can I…Can I lick your pussy?”

Caroline almost passed out right there, at that question. “Um…Okay…”

Before it hit her this was really happening, Caroline was on the bed, with Jennifer’s head bobbing between her legs. “Uhm…Hm…” Caroline had been eaten out by other girls, including the friend who got her in, but, now…Jennifer Aniston…had her tongue buried…in Caroline’s pussy.  Instinctively, Caroline started squeezing her tits, and pinching and pulling her nipples. “Oh, f…Fuck…” Caroline squeaked, as she felt Jennifer’s tongue massaging her clit.  She was within seconds of cumming, when suddenly, Jennifer lifted her head out of Caroline’s snatch.

“Hm…Turn over…”

A little confused, Caroline did so.  She had no idea what Jennifer was about to…Wait…She felt her cheeks being spread, then…Jennifer’s tongue…on her asshole.  Caroline had had her pussy licked by other girls, but never that part of her. “Mmm…” It felt weird, but really good.  Caroline was about to slide one hand under her, when she felt Jennifer’s fingers in her pussy. “Oh, God…” Caroline whimpered, as she felt another orgasm welling up in her.  When it finally hit, it was the most intense she’d ever experienced, causing Caroline to let out a shrill scream, the likes of which had never escaped her lips before.

As Caroline recovered, she felt Jennifer kissing her ass-cheek, then her lower back. “Did you like that, sweetie?”

“Yeah…” Caroline moaned, then rolled onto her back, to find Jennifer kneeling in front of her, smiling.

“I’m glad.”



“Can I…do you now?”

Barely missing a beat, Jennifer fell backwards, and lifted her legs up to her body. “You go right ahead, honey.”

Caroline crawled over to her, and soon found herself face to face with Jennifer’s pussy, her twat smell filling Caroline’s nostrils.  Without another thought, Caroline leaned down, and tucked in.

“Ooh!  Oh, Caroline!  You must do this a lot!” Caroline’s friends, the ones she had eaten out, often told her she was the best pussy-licker in school.  They’d never believe Jennifer freaking Aniston had complimented her cunnilingus skills.  As Caroline’s tongue probed deeper, Jennifer’s juices were all but gushing out of her. “Fuck…” Jennifer gasped, feeling herself up.  Suddenly, remembering how it felt having her asshole eaten out, Caroline extended her middle finger, and inserted it into Jennifer’s butt. “Ooh!  Fuck!  That’s it!” Jennifer started bucking her hips. “Oh, God!  Rub my clit!  Fuck my ass!” Caroline got into a kneeling position, and starting fingering Jennifer’s asshole fast and rough, while, with her other middle finger, she diddled Jen’s clit. “Oh, fuck!” Jennifer groaned, baring her teeth, “Here it comes!” Suddenly, Jennifer’s cunt sprayed all over the bed, and all over Caroline. “Ohhhhhh!” Jennifer sighed hoarsely, as the orgasm subsided.

“Caroline?” Jennifer wheezed, and Caroline came up next to her.  Seeing her, Jennifer smiled. “That…was incredible!  Thank you!”

Caroline just smiled back. “You’re welcome.” Without another word, Jennifer pulled her down, and they shared another long, tongue-heavy kiss.

Later, her friend, the one who got her in, asked her what happened.  Caroline’s only response was to show her the huge tip Jennifer gave her.

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