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Author Topic: Encounter with Jenny (featuring Jenny McCarthy)  (Read 7195 times)


Encounter with Jenny (featuring Jenny McCarthy)
« on: March 05, 2021, 06:27:03 AM »
First posted to c-s-s-a.com in 2002.

Author: Unknown

Encounter with Jenny

Kirk had been working long hours this week at Le Capitan. Over a period of 3 months, Le Capitan had become the hottest restaurant in Hollywood, drawing some the biggest stars around. Just this week Kirk had run into Jim Carrey, Brad Pitt, and Johnny Depp. This is not to say Kirk hadn’t seen his fair share of women. He had waited tables for Sandra Bullock, Angie Everhart, and Claire Danes among others.

It had been hard to manage schoolwork and his job, as any college student would attest to. This is especially true when your major is biology. But Kirk loved to be around anything that had to do with movies, and the restaurant was just a melting pot for movie talent. He would occasionally stumble into conversations about upcoming movies and TV projects. It was a great
thrill to be around the people behind the movies and television shows he loved. As far as Kirk’s personal life went, it was nonexistent. He had broken up with his girlfriend nearly 4 months ago and was still a virgin. All the stories he had heard about college girls were lies – at least at his college. His only satisfaction came from the women who frequented the restaurant. He had made at least 4 trips to the bathroom the night he waited on Salma Hayek. She had worn this extremely low cut dress that night, showing off her perfect cleavage. It took all his willpower to keep from mauling her shapely breasts. The amount of beautiful women coming to the restaurant was extreme torture for a virgin, and Kirk wondered if a person could die from masturbating as frequently as he did.
Tonight looked like another torturous night, but it would turn out to be one of the most pleasurable evenings of young Kirk’s life. Wednesdays were usually busy, and tonight was no exception. Jerry Seinfeld’s party had been running all night, and Kirk was having a hard time meeting the demand of Jerry’s guests. Fumbling with a tray of beer, Kirk walked over to the kitchen and nearly missed the vision sitting at a table in the corner. Luckily, Kirk’s peripheral vision didn’t let him down. There, sitting with her newlywed husband, was Jenny McCarthy.

Jenny had been one of the first girls that Kirk had really gotten into. From her Playboy appearances to Singled Out, Jenny had been a constant image in Kirk’s mind. Never mind the fact that she could be a tad gross from time to time, Jenny was gorgeous. Kirk remembered those first Playboy pictures he had seen of her in a bathtub, rubbing soap all over her naked body. Of course, those magazines had long been disposed of once Kirk had discovered a certain talent common to all teenage boys. Looking at her now had the same effect as those Playboy pictures had had. Jenny, now with black hair, still had an amazing figure. The tight leather suit she had on hugged her large chest and toned legs. Instinctively, Kirk began to walk over to Jenny's table. Just at that moment
the kitchen door swung open and knocked Kirk to the ground, soaking him in beer. The whole restaurant turned and saw the incident and, in classic Hollywood fashion, all rose up out of their chairs and applauded.

Jenny led the cheers with a whistle and hoot. After a few moments of laughter the rustle subsided and Kirk got to his feet and tried to salvage some dignity. He proceeded into the kitchen to clean up and get his next table. When he was assigned to Ms. McCarthy’s table, Kirk begged to get another assignment. The last thing he wanted was to be remembered as a blundering idiot. Of course his compassionate boss declined his request and Kirk grabbed two menus and headed for the table. As he walked out of the kitchen and toward Jenny’s table, he noticed her husband had disappeared. Well, Kirk thought he was about to find out just how much humiliation a person could endure. “Good evening, Ma’am. Would you like to start with some appetizers tonight?”

Jenny snorted as she laughed. “What the hell is all this Ma’am stuff. Did I age like 10 years since Scream 3 came out? Anyways, I enjoyed the show you put on back there sporty. What’s your name?”

Somewhat dazed, he answered

“Umm, Kirk.” “Well, my name’s Jenny,” she responded.

“I know, I’m a big fan,” Kirk said enthusiastically.

“Doesn’t look that way to me,” she said as she moved her eyes down. Kirk then realized the hard-on he had and couldn’t believe the embarrassment. Not only was Jenny making fun of his clear infatuation with her, but she was also making fun of his size (or lack thereof). Kirk was about to run away and escape this situation when Jenny laughed and commented

“Relax cutie, I’m just having a little fun. You’re too jumpy.” She began to stare at him. “Hmmm, I bet you’re a virgin. Yeah….that’s it! Oh, poor baby,” she said as she stroked his cheek. “I bet this dress isn’t helping either,” Jenny remarked as she adjusted the top of her dress. Her breasts jiggled as Jenny tugged at the tight leather.

“Listen,” she said, “how about meeting me later? I’ll slip you my hotel and room number in the bill.”

“What about your husband?” Kirk asked.

“Oh don’t worry about him,” Jenny reassured. “He’s off to some show or something tonight after dinner. Now, about that appetizer…”

It was excruciating to wait. Kirk could only imagine what Jenny had in store for him. This was his fantasy come true. He couldn’t wait to tear off her clothes and lick those hard nipples and rub the treasure between her legs. He stared at Jenny’s table the whole night, and boy did she have fun with that fact. Jenny knew she used quite a bit of hand gestures when talking, and relished the fact
that Kirk was watching her ample chest shake about.

Jenny also squirmed in her seat quite frequently, and the leather of her suit slid freely against the leather seats. But to top it off, Jenny moved her hand below the table away from her husband’s eyes and Kirk lost view of her fingers as they slid into her pants. All Kirk wanted to do was to run to the bathroom, but he knew that waiting would be far better. Their dinner was over and Kirk rushed the bill to Jenny’s table. She slapped her husband’s hand as he reached for the bill, and proceeded to open her purse for a credit card. Kirk went to process the card as Jenny got out some cash for a tip.

“Alright, let’s go,” she said as she and her husband got up and put their coats on. She laid the cash on the table along with a small note that she had written earlier while her husband
was in the bathroom.

Kirk ran over and handed her the credit card. “Thanks for coming to Le Capitan,” said Kirk.

Jenny grabbed the card and smiled, “The food here sucks. Bye!”

Kirk laughed and watched the two leave. He went over to the table and found the piece of paper.

“God,” he whispered as he read the note:

“Hilton Rm 315 12:30. Don’t forget to spill more beer on yourself. I like my men skanky.”

This was too good to be true. Kirk got to the hotel well before 12:30, and waited in the lobby till it was time. He got to Jenny’s door and was about to knock when someone grabbed him from behind.

“BOO!” Jenny shouted. “Hahaha. God, you’re so jumpy. Let’s get you inside.”

She opened the door and Kirk walked in. He admired the lush furniture and view that Jenny’s money could afford. Jenny closed the door behind him and took off her jacket.

“Make yourself comfy on the couch. I’m gonna get some wine.”

Kirk took off his jacket and sat on the couch. Kirk couldn’t believe it. He was about to lose his virginity to one of the sexiest women in the world. He couldn’t wait to see wait Jenny had in store for him. Jenny returned with two glasses of wine. She looked so sexy in that tight black leather. How could she breathe.

“You’re old enough to drink, right?”

“I’m old enough for a lot of things,” Kirk replied.

“Ha! You’re a regular Casanova, aren’t you. Just what do you think is going to happen tonight? Ya think you’re gonna get laid or something?”

Kirk began to tense up. Had he misread the entire situation?

“I…uh….well…you said…”

“No, c’mon, tell me what you thought,” Jenny said.

“Well, I thought you meant…well…the way you, uh…”

“Will you just fuckin’ tell me what you thought was going to happen!!” Jenny demanded.

“I thought we were going to have sex.”

“Oh really,” she said as she made herself more comfortable on the couch. “What would you do to me?”

“What do you mean?”

“Oh, c’mon. What kind of things would you want to do to me?”


“It’s ok,” she smiled as she placed her hand on Kirk’s.

Kirk had to get used to Jenny’s teasing.

“Well, I would start by running my hands through your hair, even though it’s black now.”

“Ouch! Continue.”

“I’d bring my lips to yours and part your mouth open with my tongue, and…”

“Hold on,” Jenny laughed, “I can see you’ve thought this through. Most guys would have said something like ‘well, I’d shove my fist up your pussy’ or something like that.”

She looked into his eyes in a way that almost melted him.

“You’re going to enjoy this Kirk. I promise.”

Jenny led Kirk to the bedroom and shoved him onto the bed.

“What do you find most attractive about me Kirk?” Jenny asked.

“Your tits,” Kirk answered quickly.

Jenny moved her hands up her leather suit and lifted her milky globes for Kirk. “You mean my soft, bouncy, heaving breasts,”

Jenny said in a sultry voice as she juggled her breasts with her hands. Her eyes looked straight at Kirk. Kirk smiled.

This was DEFINTELY not gross-out Jenny; this was the Playboy Jenny he knew and loved. Jenny leaned forward and kissed Kirk. No girl had ever kissed him like this. Her tongue was already deep in his month before her bottom lip even touched his. She fell forward and lay on top of him on the bed. He could feel her warm body even through her clothing. He wrapped his arms around her and pushed his own tongue into her month, eliciting a soft moan from her. He moved his hands down her back with slight reservation. She noticed the hesitation and broke part of the kiss.

She grabbed his right hand and used it slap her right butt cheek hard. “Don’t be nervous!! I’m all yours tonight. Have fun, dammit.”

She then kissed him hard, and pressed her body against his just as hard. After this, Kirk lost all reservation and moved both hands down to her round ass. He squeezed her cheeks through the
leather. Jenny got up and knelt over him. She moved her fingers to the zipper at the top of her dress and slowly moved the zipper down. To Kirk’s surprise she WAS wearing a bra underneath – a leather one at that. Jenny was breathing heavily and the swells of her breasts were aching to be released from their constraints. She again took Kirk’s hand and placed it on her left breast. Kirk rubbed his fingers off the flesh pouring over the top of her bra. He brought his other hand up and proceeded to do the same with her right breast. The were so warm and soft.

Jenny let out a sigh, “That’s right. Be gentle. Enjoy the moment.”

He moved his hands to the sides of her breasts and pushed them up slightly. He could see her nipples pushing against her bra and the tops of her areola peeking out
from the top of the material. Jenny reached behind her and undid the clasp of her bra. Kirk removed the bra himself and gasped as he saw Jenny topless in front of him. She arched her back and her breasts rose up, never sagging the least bit. Her breasts were absolutely perfect, and her nipples were exquisite.

Kirk gently rubbed his fingers over every inch of her breasts, lightly grazing her hard nipples. Jenny was going crazy with the teasing (finally she’s getting a taste of her own medicine, Kirk thought). Kirk couldn’t resist anymore and he grasped her breasts firmly and lifted them up.

“Ohhhh,” Jenny moaned.

He continued to knead and fondle her breasts as he moved in to kiss her. Jenny was now under his control, exhibiting none of the force she previously had. Kirk was the one pushing his tongue deep into her mouth. Jenny finally managed to break the kiss and say,

“Suck my nipples.”

Kirk eagerly complied, but was definitely not going to be satisfied with just her nipples. No, he had imagined exactly how he would do this from the first time he saw Jenny. With Jenny still
kneeling above him, Kirk began to kiss down her neck, and as he reached the top of her breasts he began to lick down the side of her right breast, dragging his tongue around the shapely curve. Jenny again moaned as he did the same with her left side. He pushed her tits together and kissed every inch of her melons. It was an eternity before he finally pushed her nipple with his tongue and then planted his lips squarely on them. He continued to knead and lick her chest.

“You sure do like those, don’t you?” Jenny said.

Kirk laughed and pushed her onto the bed. He buried his face in her cleavage.

“Unnggggh. Yeah, play with my tits.” He again pushed her breasts together, bringing the nipples to close so her could lick them together.

“Ohhhh God, you’re so disciplined. My husband would be in my pussy by now – no foreplay.”

Kirk was loving every minute of this. Jenny rolled over so that she again was on top of Kirk. She tore off his shirt and bit his nipple.

“Ouch! Hey, watch it!” Kirk shouted.

“Big baby,” Jenny laughed. She rolled her tongue down to the top of his pants and grabbed at his belt buckle. She
undid the buckle and opened his fly. Kirk was so hard at this point, but that was to be expected after having his way with Jenny McCarthy’s breasts. Then Kirk suddenly remembered the incident at the restaurant – about Jenny’s joke involving the size of his member. Jenny pulled down his boxers and the nervousness he thought he was rid of returned instantly.

Kirk knew he was not hung; his cock was about 5 inches – not even average.

Jenny spoke up, “I bet you’re thinking about that crack I made at the restaurant. Believe me tiger, a guy who can make a slut like me go crazy by just playing with my breasts is well on his way. Besides, I think it’s cute.”

Kirk’s laugh was cut short by Jenny’s hand on his cock. She was lightly kissing the sides of it, while her hand was nestled under his balls. She kept poking her tongue on his cock head.

“God Jenny.”

She giggled and took his dick into her mouth. Kirk was in heaven as he felt her tongue swirl around his shaft. She continued to suck his dick, and Kirk didn’t know how much longer
he could hold out. She finally removed her lips from his cock as a strand of spit and precum rested on her chin.

She grabbed his dick and began stroking, harder each time she brought her hand down.

“Jenny, I’m going to…….”

“Don’t worry baby, we’ve got all night.” With a final stroke Kirk let out a moan and shot a thick stream that he thought would fall to the bed. Instead Jenny caught it in her mouth, as she continued to pump him. He shot two more thick loads onto her cheek and the side of her eye as the rest of his cum ran along his shaft.

Jenny let out a shout and said,

“Wow, this little guy has some life to him.”

Kirk begged, “Please, enough with the size jokes.”

“Ok, ok.” Jenny rubbed her face on Kirk chest, rubbing off the cum that he had sprayed her with. She licked off the
cum as Kirk looked at her glistening face.

The night was just getting started. After Jenny had thoroughly licked Kirk’s cum off his own chest she stood up on the bed and began to sway and gyrate like a stripper. Her breasts bounced up and down as Jenny rubbed her hands down her leather-clad thighs. Jenny undid her fly and peeled the leather pants off her. Leave it to Jenny to wear a bra but not wear panties. Kirk licked his lips as he looked at her neatly trimmed pussy. Jenny turned to reveal her tight ass, spanking her left cheek twice.

“Come and get it stud.”

Kirk grabbed her by the hips and brought her down so that Jenny was sitting on his face. He licked and kissed her soft butt cheeks, and with a sudden rush of realization, pushed her off to the side.

“Jenny, you’re not going to fart of me, are you?”

She laughed and assured him, “I’ll try not to.”

Kirk rolled Jenny onto her front and moved his head to her ass. He laid his head on the soft cheeks.

“Taking a nap, are we?” Jenny remarked.

With that Kirk grabbed a handful of her flesh had firmly bit down.

“AHHHH, shit!" Screamed Jenny. "You’re sooo bad.”

He laughed and saw the red mark he had left on her cheek. He moved his tongue over the area to cool the sensation. Kirk squeezed Jenny’s left ass cheek as he continued to suck on her right. After a couple minutes of this he knelt up and rubbed his hands down the back of Jenny’s legs. Jenny turned over and he got a close up view of her tight pussy.

“I don’t deserve this,” Kirk thought to himself.

As if reading his mind, Jenny responded, “Like I said, I’m yours tonight.”

Kirk rubbed his hands along Jenny’s thighs, bringing the tip of his fingers up to her pussy. Kirk knew Jenny was extremely horny at this point because her pussy was completely soaked. Kirk rubbed his finger against her clit and drove Jenny past the boiling point. Jenny grabbed Kirk by the hair and shoved his face into her pussy. Kirk was caught off guard, but quickly opened his mouth and licked any area within reach.

“Ohhhhhhh, baby, yeah, suck it.”

Kirk brought Jenny’s legs up to surround him with her scent. Kirk lapped at her pussy with no abandon.

“Ahhhhhhhh, FUCK, FUUUUUUUUCCCCCCKKKK,” she screamed as she orgasmed, driving Kirk’s face into her pussy to the point where he could hardly breathe.

Kirk licked her pussy dry and brought his cum soaked face up from Jenny’s pussy. He climbed up to her face and kissed her. Jenny licked at every corner of his mouth, taking in her own juices. Kirk and Jenny caught their breathe. Jenny finally spoke up,

“Wait right here…” Jenny returned with a condom in her hand, tore it open in a matter of seconds, and started to slip it on Kirk’s dick. It was pretty snug,
and Kirk guessed Jenny’s husband must not be that well hung either. With the condom in place Jenny pushed Kirk down and mounted him. She bounced up and down his shaft, moaning and panting. Every inch of her breasts bounced and quivered with her movements. Kirk shoved Jenny onto the bed and fucked her missionary style. Jenny screamed as another violent orgasm hit her.


Kirk was near the brink too and wasn’t going to waste his cum inside a condom. He quickly removed his cock from her and peeled off the wet condom. He took his dick and placed it in
between Jenny’s soft mounds of titflesh. Jenny caught on and smiled.

“I knew you couldn’t lay off my breasts for that long.”

Kirk titty fucked Jenny, and Jenny made sure Kirk wouldn’t last that long.


Jenny pressed the sides of her breasts tightly around Kirk’s dick and he shot his wad all over her massive chest. Jenny took his softening dick in his mouth and sucked him dry. Jenny then lifted her breasts to her mouth and licked them clean as well. Jenny started

“Well that was fun………..UNNNNNNGGGGGGHHH!!”

Jenny was cut off by three fingers entering her pussy.

“God, I love you!!” Jenny shouted. Kirk finger fucked Jenny until she came twice more and they both lied there exhausted till the next morning.

Kirk awoke the next morning and looked at the woman next to him. Jenny McCarthy, still asleep and quite naked, lied next to him. He hadn’t dreamt last night. He had lost his virginity to the woman of his dreams. He looked at the time and remembered he had an early shift that morning.

He was confident that no other day at the restaurant would equal his night with Jenny McCarthy.
All stories posted from this account were once on C-S-S-A.com and belong to the respective authors we have credited in disclaimers. Our goal is to preserve these stories as part of internet porn history and ensure they are not lost in time.
The following users thanked this post: Nikko, flawed_existence


Re: Encounter with Jenny (featuring Jenny McCarthy)
« Reply #1 on: July 29, 2021, 07:27:30 AM »
Oh yeah Jenny! Awesome. I really liked this story, well done!


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