Note: All characters in the story are 18 or older when referring to anything of a sexual nature, whether past or present.
Trish waited in the hotel room across the hall from Mags, wondering if the recently-deflowered 18 year-old would get up the nerve to not only get dressed in the skimpy outfit Trish had left for her, but also allow herself to be the center of attention of several eager, hungry, and aroused men. Mags had spent the past 24 hours losing her virginity after her prom night, first with her date, then his brother, then both at the same time… and then Mags watched as Trish fucked her husband and a few of her “regulars” on her hotel room bed. Trish knew Mags’ curiosity was certainly elevated. She left Mags the outfit that Trish, herself, was requested to wear, and a note, letting Mags know there was more fun to be had across the hall.
Trish was in one of two rooms across the hall, so she knew there was a fifty-fifty chance Mags would come to this one, instead. If she did, the guys Trish fucked in her room earlier that evening were a text away, and she was sure she’d be able to keep Mags entertained for the 20 minutes it would take for them to show up. She’d walk down the hall to the other party, herself, once Mags was occupied. But if Mags went to the other room…
Trish’s pussy became wet just thinking about it. In the other room were several older gentleman that were looking for “entertainment” for the evening. Trish’s husband actually answered the ad for her, as he knew how to find requests of that nature. But after hearing about the transformation Mags had undergone in the last 24 hours from one of her regulars, she was excited to listen while Mags enjoyed the older gentlemen in what would undoubtedly be her first of hopefully many gangbangs. Even at the higher price, the walls of this particular hotel room weren’t going to be thick enough to stop Trish from hearing at least some of what might go on in the next room.
While she waited for fate to guide Mags, Trish looked in the mirror across from the bed.
Married, no kids, enjoyed sex with multiple lovers at the same time, and a husband that encouraged her. Taller than most 22 year-old women at 5’7″, and in great shape. Thick, dark brown hair kept just below the shoulders. Tanned easily, and alternated between tan lines and an all-over tan. Ears and nipples were pierced, but that was all she felt comfortable with. Modest, but firm 34C breasts, which looked great with or without a bra. Her little sister, Sherry, would eventually be the lucky one to get the bigger boobs and hips, but is about 6″ shorter. Her little brother was completely out of shape, but she hoped he’d start using the weight lifting machine she bought him for Christmas. Trish took ballet as a kid, but mostly stayed in shape these days by swimming, running, and fucking. She used to shave her pussy until her husband paid for laser hair removal. One tattoo on her left foot, but that’s it. Her finger and toenails were impeccably maintained, and the girl that did the maintaining had her tongue in Trish’s pussy at least once a week.
Trish wasn’t sure if she was what someone might call a Hot Wife, or just an all-around slut. She likes a lot of dick. And, she can take a lot of dick. Her sister once asked how she handled two or more guys a the same time. Trish explained, “Ever see those people that can play the piano and sing at the same time? It’s a gift to have that kind of concentration and control. I have that. Except, I can ride a cock in my pussy and ass while giving a mind-blowing blowjob and sensuously stroking a cock in each hand, and never skip a beat.”
She also confided that that kind of skill doesn’t happen overnight, or so she thought before hearing about Mags. For Trish, it started out a little slower.
—
Trish was a late bloomer when it came to her sexual adventures. Everyone knew she had potential to become very pretty, even at a young age. When Trish’s parents finally allowed her to start dating, she still had braces, acne, and a training bra. She was allowed to go to the movies with a boy, and maybe for pizza or ice cream. During the Summer, they’d let her go to the water slides or the beach, but that was about it. She learned about kissing, and appropriate public hugging from her mom, but when it came to dances and proms, there were boys that she liked because they were friends, and boys she liked because they were just so damned cute.
Eventually, the day came when a cute boy asked her to a dance, and then a friend asked her a day later, and she found herself in a bad spot. She liked both of them, but didn’t want to hurt the friend’s feelings… but, she still wanted to kiss the cute boy. To her surprise, they agreed to both take her to the dance – a homecoming dance – her junior year of high school. For the next two years of high school, she found herself going on dates with two guys almost every time she went out. Her mom thought it was because one was the protective friend while the other was the bad boy type she warned Trish about. Little did she know they were both usually the bad boy type.
Not every two boys got along or wanted to share Trish’s time. That was disappointing as she was getting used to the attention. Luckily, for every time that it didn’t work out, there were times when more than two guys wanted to take her out at the same time. It didn’t take long for Trish to develop a reputation. She was never seen with just one boy. When the braces came off and her face cleared up, she went from pretty to sexy, and she found herself going on dates almost ever other night of the week. Luckily, she was as smart as she was pretty, and an hour of homework each day kept her grade-point average high enough to graduate with honors. She was smart, pretty, popular, and discreet.
Trish knew that some of her friend’s moms disapproved of her always being seen with two or more boys, while other moms just took a look at her and said the boys couldn’t help themselves. The years from 16 to 17, and finally 18 were very transformative. She was attractive to both sexes.
The first time she kissed a boy, she kissed two. The first time she rubbed a growing bulge in a pair of jeans WHEN SHE TURNED 18, she rubbed two.
She surprised everyone when she went to her senior prom with just one boy.
Tim was, well, timid.
He was polite, quiet, maintained his boyish charm even at 18 years of age, and respectful to everyone he met. He wasn’t incredibly handsome, and as Trish would later find out, not particularly well-endowed. But he was nice. The kind of boy Trish’s mom thought she should marry.
Maybe. Someday.
When she left the dance, though, several other schoolmates shared the limo to be dropped off at their respective homes. The five couples dropped off the girls first, with Trish being the last girl to be taken home. Her date, Tim, knocked on the privacy window and asked the driver to take the long way, and then settled back in seat next to Trish.
She had asked Tim to get a hotel room for after prom, but he couldn’t think of a reason to be out all night and most of the morning as an alibi for his parents. And honestly, Trish couldn’t seem to come up with one, either. So, the limo was going to be the next best thing. What Trish hadn’t counted on, was four other guys joining them, not that she minded.
When Tim bent down to pull off her garter, she spread her legs seductively, showing the other boys that she wasn’t wearing panties. She hadn’t been, all night. One of the boys fished in his tuxedo jacket and handed someone a $20 bill, apparently losing the bet over whether or not Trish was wearing panties.
Another produced a $20 and handed to someone else. Shaved pussy.
She also opted for no tan lines for prom thanks to the local tanning salon. Another $20 bill exchanged hands.
Tim kissed her deeply, and let his hand slide up her dress to her wet slit.
He was a good kisser.
“You don’t mind making out in front of them?” Trish asked. “I know we’ve made out before with one boy watching, and sometimes with you watching me make out with another boy, but there’s four, now.”
“I don’t mind if you don’t mind.” Tim answered as his fingers glided along her swollen clit.
Tim knew that Trish’s idea of making out was more than French kissing each other’s mouths. She wanted to feel his tongue on her clit. He quickly knelt between her legs as she pulled them back, giving everyone a better view of her hairless sex and pretty butthole. Tim wasn’t nearly as good as some guys that had gone down on her, and not even close to some girls, but he was thorough. And, his jaw never seemed to get tired, so with a few fingers in the right places, he could get her to come, eventually. While she liked a good pussy licking, she was aching for something bigger to be filling her up.
Trish was no stranger to blowjobs, and knew every guy was different in what they liked and how they recovered afterward. She knew Tim needed to be blown quickly, and then he was good for a hard-on for at least 15 minutes afterward. She interrupted Tim’s tonguing and had him sit where she had been sitting. She turned herself so she could bring her face to his lap while keeping his fingers inside her. The four boys sitting opposite her watched and rubbed their groins intently.
She had Tim’s manhood down her throat in seconds. More money exchanged hands.
“What was that for?” Trish asked, letting Tim’s cock pop out of her mouth.
“Whether or not you gave good head.” One of the boys answered.
“Well, I think you lost that bet. I give great head.” Trish answered as she placed Tim’s cock back in her mouth, and slowly took his full length down her throat. She kept her eyes on the other guys as she pulled back up and then sucked him down her throat again.
She didn’t recognize any of them. She wondered why Tim agreed to share the limo with them, as she was fairly certain she hadn’t dated any of them, before. When one of them undid his pants and let his shaved, cut, and unnaturally wide dick flop out, she was definitely certain she hadn’t dated him before.
Tim came, almost on queue, and Trish swallowed easily, never taking her eyes off the four other boys undressing across from her. More money exchanged. Yes, she swallowed.
Tim helped her out of her dress and folded it up neatly on the ledge below the privacy window, leaving her to sit wearing her thigh-high stockings, garter ensemble to hold up the stockings, half-bra that pushed her tits up but didn’t cover her nipples, and her high-heeled sandals. Tim knocked on the window, and asked how much time was left before the driver had to drop them off.
“As much time as you need,” the limo driver winked and smiled.
—
Trish had lost her virginity a few months before prom, on the night of her 18th birthday party. SHE WAS 18. She had promised her mom to wait until she was 18 before going “all the way” with a boy, so she did, more or less. She thought it was funny that she was going to play bus driver and drive a few of her friends home after the party was over, having just received her driver’s license. The last two boys to be dropped off had dated her on and off for a few months and knew about her promise to her mom. She pulled off the main road, down a gravel road leading to one boy’s parent’s house in a wooded area, and turned off the car. She hadn’t dressed particularly sexy, but the pheromones in the SUV let her know it must have been sexy enough. Her usual heavy petting while French kissing quickly turned to stiff cocks in each hand and fingers jack-hammering her recently-shaved wet pussy and saliva-lubricated butthole. They fooled around inside the SUV, outside the SUV, and then back inside the SUV when they started getting too cold. She didn’t have anal sex that night, but they both took several turns in her pussy. First one, then the other, and then both. They weren’t very well-endowed, but – as she would say years later – they got the job done.
They both used condoms, so making the leather seats look presentable when she got home took almost no effort. She felt sore for most of the following day, but she was surprised there wasn’t more blood. She had always heard horror stories of what a mess the first time made. A little Kleenex that her mom kept in the glove compartment took care of things. Intercourse with one boy was good, but she decided, then, that intercourse with two was much better.
She wasn’t sure if she orgasmed during her first time – or times – until a few weeks later when one of the girls at school asked her if she was still a virgin. Trish didn’t mind telling her she wasn’t, and the girl pressed with more questions. She seemed to know a lot about the female orgasm, but nothing about how to handle a throbbing dick. When Trish pressed with her own questions about how this girl knew so much about the clit and G-spot, the girl lifted herself on her toes and kissed Trish full on the mouth. Trish’s shock lasted less than a second and kissed the girl back. The girl knew how to kiss.
When Trish finally pulled away, she looked side to side to see who, if anyone, was watching.
Everyone.
“And that’s how you should kiss a boy,” Trish said confidently. She closed her locker door and walked to her next class, wondering if the other girl’s pussy was as moist as hers.
Two days later, after most people forgot about the hall kiss, the girl approached her again.
“Want to study together, sometime?” she asked quietly.
“You mean make out?” Trish asked.
“More, if you’d like?” she asked sheepishly.
“More? I always like more,” Trish said with a wink and a smile.
That afternoon, Trish found herself in the girl’s bedroom, door locked, parents not home, dog outside, with a tongue on her clit and several fingers massaging her G-spot. The orgasm was intense. No mistaking it, this time. She came, and she loved it. The girl pushed Trish’s legs back and let her saliva drip onto Trish’s anus. The girl used her pinky finger to caress, and then press into Trish’s butthole. She let Trish lower her legs and resumed her mouth magic on Trish’s pussy, gently gliding her pinky further and further up Trish’s butt. She put three fingers in Trish’s increasingly wet sex and let her tongue go wild.
“Oh fuck!” Trish cried out, almost breaking the girl’s fingers as her pussy tightened. She thought her first orgasm was intense. That paled in comparison. The two girls took turns going down on each other for the next two hours, until the dog started barking when the girl’s parents came home.
They quickly got dressed, not paying attention to whose clothes were whose, and resumed their positions cross-legged on the floor with books all around them. The girl forgot to unlock the door, and unlocked it just as her mom was about to open it.
“Studying hard?” the girl’s mom asked.
“I think I’m finally getting it,” Trish nodded.
The girl’s mom smiled and went about her motherly duties while the dad leashed the dog for a walk.
“Ummm, this was fun,” Trish said uncharacteristically softly. “But…”
“But, you still prefer boys,” the girl said, disappointed.
“No, well, yes, but,” Trish continued. “I like you. I like the way you taste. And you seem to obviously like the way I taste. I’ve never come like that before. Maybe I’ve never actually orgasmed before. I must have been close – with boys – but nobody took me over the edge. In that respect, you’re my first.”
“Can we do this again, sometime?” the girl asked, as if admitting she was crushing hard.
“Absolutely!” Trish answered, realizing she was wearing the girl’s underwear backwards. “But, you really need to try dick. Think you can try riding a boys cock the way your rode my face?”
The girl nodded.
They had two more study sessions, but the girl never accepted invitations to “double-date” with any of Trish’s boyfriends. After the third declined invite, Trish decided to stop studying with the girl.
“Missed opportunity,” Trish thought. She didn’t write off the girl completely, though. Years later, the girl ended up working in a nail salon while attending the local community college, and Trish became her most appreciated customer.
—
Trish had been on birth control pills for a few months – for her acne management, she told her mom – and believed the pills were more effective than they actually were. She was flattered when a boy pulled out a condom, but they seemed to forget all about STDs when it came to blowjobs as they always pulled the condom off when it came to oral sex. She knew Tim wanted to fuck her – it was the whole reason for the limo, and she definitely wanted to get fucked by him, even in front of the other four boys. But she hadn’t counted on them wanting to fuck her, too.
“Well, of course they want to fuck me, too,” Trish thought to herself. “What did I think they were going to do while Tim bounced me on his lap? Masturbate?”
Actually, that WAS what she thought they were going to do. Maybe she would give them handjobs, or blow them one at a time while Tim fucked her from behind. Okay, maybe two at a time.
When she watched one of them pass around a belt of condoms, her nipples involuntarily hardened.
Her pussy unexpectedly convulsed and tightened around Tim’s shaft, producing Tim’s usual “oh fuck” mumbling as he filled the condom. He was still new at fucking, and sometimes he could last fifteen minutes, and other times, maybe three. This was one of those other times.
“Damn it,” Trish thought to herself. “I was just getting started…”
As Tim withdrew from her, she sat on the bench seat next to him and kissed him before whispering in his ear, “Are you okay with me having fun with them, too?”
Tim nodded, embarrassed that he had come so quickly.
“Sorry I didn’t last longer,” Tim said in a whisper.
“It’s okay. It felt really good. I was just really close to coming, too,” Trish said, a little louder than a whisper. “Can you just make sure things don’t get too out of control? We don’t know these boys.”
“I know them. They’re okay,” Tim assured her.
Trish looked at Tim hard for a moment, then back at the four boys sitting across from her in varying stages of getting undressed. She leaned over and undid her high-heeled sandals, handing them to Tim, and then unhooked the garters from her stockings. She eased the stockings down her legs, folding them neatly, and handing those to Tim, also. She unhooked her push-up half-bra and let it fall from her arms, catching it before it hit the floor. Finally, she rotated the garter ensemble, unhooked the back which was now in front, and tossed it aside.
“If we’re going to have fun together, shouldn’t I at least know your names?” Trish asked, working her way to the other bench seat on her hands and knees. They made a space in-between the four of them for her to sit, and she winked at Tim as she leaned back and let them fondle her body.
She looked at their bouncing cocks, trying to see which was the smallest. She wasn’t completely sure in the dim light of the limo, but it looked as if all of them had either shaved or very closely trimmed their pubic hair. She knew girls had been doing that for years, especially if they had a pretty pussy. But the absence of pubic hair on the balls and above those bouncing cocks on the boys took her by surprise.
She liked the look.
She pointed at the boy with a long, but not very thick member. “What’s your name?” Trish asked.
“Kyle,” he responded while running his hands over her legs.
“Kyle, may I sit on your lap? This seat isn’t very comfortable,” Trish pouted.
Kyle nodded, and Trish knew he wasn’t going to last long. That was okay. Between the four of them – five if Tim rose to the occasion again – she was sure she’d get off at least once.
Kyle moved toward the center of the bench seat, and Trish brought his legs together causing his stiff dick to point straight up.
“Nice!” Trish accidentally said out loud.
Facing Tim, she stepped back and straddled Kyle, guiding his shaft into her pussy. He slid in easily, but deeper than she expected. The limo hit a pothole, causing Trish to lose her footing. She fell back against Kyle and his full length was inside her in an instant.
“Ooohhh,” Trish cooed. “Easy, okay?”
Kyle nodded, not knowing where to put his hands, or if he was supposed to thrust into her or let her do all the work.
While Kyle was still figuring out the many mysteries of life, Trish noticed the limo driver looking at her in the rearview mirror and smiling. She hadn’t realized he could see any of this, and the thought of him taking in the sight of her turned her on even more. “Dirty old man,” she thought.
“Tim, could you ask the driver to park somewhere? I’m afraid he’s getting distracted,” Trish asked between short breaths.
Tim did, and the driver nodded. A few minutes later, the limo pulled off onto a gravel utility road behind a wooded preserve.
As Trish predicted, Kyle was a short sprinter. She couldn’t blame him, though. He just fucked a girl that wasn’t his girlfriend, and she was also probably the first girl he ever fucked.
“Who’s next?” Trish asked.
“Me,” two of the boys said simultaneously.
“Now, that’s more like it,” Trish said, stepping off of Kyle’s lap, turning, and straddling one of the boys.
“What’s your name?” Trish asked.
Again, they answered simultaneously.
“Okay, one at a time,” Trish said. “We’ll start with you, the boy with my tits in his mouth.”
“Ryan,” he answered, and went back to kissing and lightly biting her nipples.
“And you?” Trish looked behind her at the other boy that had answered at the same time.
“Sean,” he answered, not sure what he should do or where.
“Sean, do you want to try smashing pumpkins with Ryan?” Trish asked. “I’ve never done it before, but I’m willing to try it if you’d like.”
From the look on their faces, she could tell they had no idea what she was talking about.
She raised herself up, reached down and guided Ryan’s average sized dick into her pussy. She eased herself up and down a few times, and then waived Sean closer.
“Now, ease yourself into me, alongside Ryan, okay?” Trish asked.
Ryan was actually feeling pretty good inside her. She had to pause for a moment, as Sean struggled to fit his cock in her already well-occupied pussy, and she grew impatient. She kept humping Ryan as she reached back to guide Sean’s twitching dick inside her.
Trish could feel the sweat on her chest as Ryan breathed deeper on her tits. Sean still couldn’t seem to fit his cock alongside Ryan’s and eventually filled his condom just from the struggle.
“Another virgin?” Trish thought to herself.
“You, quiet one,” Trish said, pleadingly. “You want to try?”
He smiled and moved behind her. She really wanted to fuck him last, as he was the one with the unusually wide manhood. He was built like a football player, and had the dumb boyish look on his face to match.
“What’s your name?” Trish asked over her shoulder.
“Nick,” he answered, squeezing her ass cheeks. “Nick the Dick.”
Trish rolled her eyes.
Ryan started to shake beneath her, and Trish felt as if she could come at any moment.
“Just a little longer, Ryan… come on, just a little longer,” Trish pleaded.
But it was no use.
Ryan let himself slip out of Trish’s very wet pussy.
“Sorry,” Ryan said sheepishly.
Trish stepped off of Ryan and onto Nick’s lap. She kissed him on the lips and then his neck before whispering in his ear, “Please tell me you know how to fuck.”
“Oh yeah,” Nick whispered back. “I’m gonna wear that little cunt out.” Trish wished he had said that while inside her, as it was almost enough to make her come just by those words. “But, I think you should blow Tim for awhile, and maybe the other guys while I fuck you.”
Trish stepped off of Nick’s lap and turned toward the front of the limo where Tim, Kyle, Ryan, and Sean were now sitting. She crawled back over to them, arching her ass in the air toward Nick, invitingly.
She took Tim in her mouth, first, and grunted as Nick mercilessly parted her labia and pushed his meat into her. Her pussy farted as he filled her with his manhood, withdrew, and then slammed into her again.
She reached out and took Ryan in one hand, and Kyle in the other, while her head bobbed up and down on Tim’s shaft. She let Tim’s dick pop out her mouth, moved to the side, taking Kyle in her mouth, and moved her free hand onto Sean. She alternated between each of the boys, sucking, swallowing, and stroking, while Nick fucked her from behind. He had stopped the raw plunging into her swollen sex, and instead, maintained a steady rhythm, filling her with each thrust. He slapped her ass cheeks several times, leaving large handprints, only to reach under her and rub her clit when she started to groan from the pain. The overlap of pain and pleasure was playing tricks with her mind.
Again, she felt the initial waves of orgasm start to take her over, and her pussy tightened around Nick’s shaft.
“Not so fast,” Nick said as he pulled out of her now-gaping pussy.
“Fuck!” Trish blurted out from around Tim’s dick.
“Hey, Tim,” Nick said loud enough for the driver to hear. “Ever fuck her in the ass?”
The truth of the matter was he had – barely. He had fingered her butt while going down on her a few times, and she really got off on it. Eventually, she wanted him to try putting something bigger in her butt. The first time hadn’t gone well, and she felt bad for making Tim feel bad. Neither one really knew what they were doing. She learned that lube made a big difference. So did stretching before a workout. She acquired an assortment of butt plugs from a friend of a friend, and wore one almost every day for two weeks before trying again. With enough lube, it felt good, but she increased the size of the butt plugs and the amount of lube in preparation for tonight. That was preparation with Tim’s average-sized manhood in mind, and anyone else Tim’s size.
She just looked at Tim, knowing Nick’s big dick would surely tear her apart if he tried to fuck her that way. She doubted her anus was prepared for Nick, even with half the tube of her mom’s KY Jelly squeezed up her butt.
Eventually, Tim nodded.
“Good,” Nick continued. “Guess you liked it?”
Tim nodded again.
“Great,” Nick added. “Did she like it?”
Trish was wondering why they were having a conversation as if she wasn’t even there.
“Yes, but not exactly, I…” Trish said.
“Don’t worry, I’m not going to fuck your ass tonight, Trish. Some day, but not tonight,” Nick said, motioning for her to turn around and sit on Tim’s lap. “I think you should put Tim’s dick in your ass, while I really fuck that pretty little cunt of yours. Let’s show these boys what smashing pumpkins really means.”
Trish never actually fantasized about what was about to happen, next. But she certainly thought about it.
Having one boy in her butt, and the other in her pussy. Maybe one in her mouth, and one in each hand.
Before she knew it, though, that is exactly what was happening – and it felt incredible.
Nick had amazing stamina, and was very quick to regain his erection after coming.
The first time he came, he pulled out, pulled off the condom, and pushed the head of his shaft – as that was all that could fit – into Trish’s mouth. She welcomed the gesture, sucking and swallowing eagerly, still riding the waves of her own orgasm. She continued to suck him until he was three quarters erect, and then he resumed his position between her legs. She moved from lap to lap as each boy took turns fucking her ass while Nick managed to reposition and resume steadily fucking her pussy without skipping a beat.
Eventually, they ran out of condoms.
Trish told Tim they could keep fucking and coming in her ass – it was actually getting easier for her to ride their dicks up her butt while Nick thrusted into her pussy, and she really was enjoying it. But the blowjobs would have to stop – with the exception of Nick, who continued to fuck her through three of the most intense orgasms she’d ever had.
After another 30 minutes, the back of the limo completely reeked of sex. Trish was on Tim’s lap, but he was no longer fucking her. A steady stream of come leaked from her anus onto his flacid cock and drained balls. He held her legs back as she squeezed her tits and rubbed her clit while Nick fucked her hard and fast for all he was worth. She tightened her pussy around him, pulled her legs free from Tim’s grip, and locked her ankles behind Nick’s back. Her almost-violent orgasm triggered his. His whole body spasmed. As she held her legs tight, she could feel every spurt pass through his shaft and fill her with his come. He came a lot. She could feel his seed seep from around his shaft and trickle into her asshole.
“I hope you’re on the pill,” Nick said as he let his thick cock drop from her gaping, come-filled pussy.
“I hope you don’t have any STDs!” Trish said back, fingering some of the come from her open cunt and then putting her fingers in her mouth. She licked them clean, and then did it again. “You know, your come tastes really good.” She had gotten used to the unusual taste of male ejaculate, but had no idea it could actually have an appealing flavor.
The other boys cleaned up as best they could with what little Kleenex was available in the back of the limo. All but Tim, Nick and Trish got completely dressed, and one by one, the boys were taken home. Trish sucked Nick to orgasm three more times, swallowing each time, before it was his turn to be dropped off. He dressed, shook Tim’s hand, and gave Trish a kiss on the cheek. He gave the driver a few $20 dollar bills as an extra tip before turning for his parents house.
Tim helped Trish back into her prom clothes, and she did the same for Tim. When they pulled up to Trish’s parent’s house, the driver said something to Tim that put a frown on his face.
“What’s wrong?” Trish asked, still drunk from the amount dick she had taken throughout the evening. She couldn’t remember how many orgasms she swallowed, but knew it must have been a lot. And, she did feel a little drunk, not that she knew, exactly, what that felt like.
“He said the fee went up,” Tim replied.
“What?!?!” Trish panicked. “We already paid him, didn’t we?”
“Yeah,” Tim said. “That was for two hours after prom. We’ve been fooling around for four.”
“How much did it go up?” Trish was trying to think were she could find cash in the house, or her mom’s credit card at 4am.
“He says $400, because now he has to clean the inside of the limo before turning it in,” Tim replied. “Or…”
“Or what?!” Trish said, anger welling over this man ruining her prom night. There was no way she would be able to find that kind of cash in the house, and her mom would have a fit if she put that on her credit card.
“Or… you let him have his way with you for another hour, and he calls it even,” Tim said sheepishly.
“What is he, like forty years old?” Trish smirked.
“Fifty, I think,” Tim replied, surprised she was so quick to even consider it.
“Fifty-four,” the driver injected.
“Three times my age?” Trish said under her breath. “He’ll have a heart attack.”
“Do I need to ask your parents for the balance, or his?” the driver said sharply. “I’m sure they’ll want to know why the price went up.”
“Not here,” Trish said, feeling as if the evening couldn’t get any worse. “Drive.”
The limo driver parked in a new subdivision full of vacant homes and turned off the ignition.
“Don’t leave me alone with him, Tim,” Trish whispered.
“I don’t know what I’m going to be able to do,” Tim replied. “He’s kind of a big guy.”
Trish looked at Tim with disappointed eyes.
“Tim, is it?” the driver spoke as he opened the driver’s door. “Why don’t you go for a walk around the neighborhood or something?”
“I’d rather he stay,” Trish said, getting out of the limo. She had actually done a good job of looking like she just stepped off the prom dance floor. Her dress was perfectly in place, hair fixed, and new make-up applied. She cleaned up well.
“I’d rather he take a walk,” the driver said, gruffly.
“It’s okay, Trish. I’ll be right over there,” Tim said and pointed to a playground still under construction.
A strange feeling came over Trish. She was nervous. She might have actually been afraid. Maybe if she played this right, he’d come before even getting close to her and then just take her home.
“Do you want to help me out of my dress?” she asked.
“Nah, leave it on,” the driver replied with a grin. “You’re not wearing panties, so we’ll just lift it up.”
He pressed against her, pinning her to the side of the limo. She was much shorter than him, so he reached down, cupping her buttcheeks and lifted her so they were looking at each other, eye-to-eye.
“You think you got fucked pretty good tonight?” he asked.
Trish didn’t know how to answer. She was exhausted, but felt a second wind coming. For a moment, she considered kneeing him in the groin and run, but where would she run to? And what would Tim do to help?
“That meathead doesn’t know the first thing about fuckin'” he smiled, and kissed her on her freshly touched-up lips. Trish resisted at first, but gave in as his huge hands squeezed her buttcheeks under her dress.
“That’s it. Go with it,” the driver said, letting her back down.
She knelt in front of him, careful not to let her dress touch the ground, and undid his belt buckle. When she undid his fly, she was greeted with a puff of white pubic hair. She pulled his pants down over his muscular thighs, but the driver’s cock didn’t spring free until his pants were down to his knees.
His tool was almost as thick as her wrist, and almost as long as her forearm. And it was covered in bumpy veins. Worse, he wasn’t even fully erect, yet.
She couldn’t close her hand around his shaft as she guided it to her mouth. She cupped his balls with her other hand and couldn’t believe the size of his sack. Her hand could barely hold one ball, his nuts were so big.
“I thought you said you were great at giving head?” he smiled from above her. “I have to admit, though, you are pretty good.”
She tried. Should could get more than just the head of his shaft in her mouth, but taking him down her throat was almost impossible. Almost. She choked a few times, gagging until snot and tears ruined her face.
“Okay, that’s enough,” he said, pulling her up to her feet. “Let’s see if you’re wet, yet.” He lifted her dress and reached between her legs. “Oh yeah!” he exclaimed. “And I don’t think that’s all meathead’s jizz, either.”
He opened the limo door, cock jutting up and out, and waived for her to step inside. She did, thankful to be out of the cold night again.
Trish positioned herself on all fours, facing the back of the limo, and pulled her dress up to expose her red hand-printed buttcheeks. She looked over her shoulder, waiting.
“In a hurry?” the driver asked.
“Do you have a condom?” Trish asked.
“Nah,” the driver answered as he moved closer. “When I come, it’ll be in your ass or your mouth. For now, though, lets work up to that by letting me give that little pussy of yours a try.”
Before she could protest, he was inside her.
Her pussy farted as she tried to accommodate his length and girth. He gripped her hips tightly and pulled her back onto his shaft. When she started backing up onto his tool on her own, he relaxed his grip, and then eventually let go.
“Now you’re getting it,” he said, running his hands over her thighs and calves.
He reached for one foot, and undid the high-heeled sandal. Without stopping her rearward thrusts onto his pole, Trish brought back her other foot so he could remove the other sandal.
“Talented, and a fast learner,” he said, watching as she fucked herself on his dick.
He licked a thumb and pressed it onto her butthole. She angled her butt upwards on the next rearward thrust, pushing his thumb into her anus.
“Like that, huh?” he said, pushing his thumb in further. Trish responded by slamming her ass harder against his thighs with each rearward thrust. She could have sworn she felt her internal organs readjusting their position just to take all of him inside. Her arms began to shake. At first she thought it was just muscle failure, as she had been in this position for what seemed like 15 minutes. But when the orgasm took over her, she let out a low, “Oh Fuck!” which seemed to surprise them both.
“That’s a good little slut,” he said. “That’s it, keep fucking yourself on my dick. Don’t stop.”
He felt so good inside her, she couldn’t figure out why he wasn’t coming, too. Despite wanting to stop and just go to sleep, she did as he said, and kept slamming against his thighs. His cock remained rigid inside her and she felt the second wave of an orgasm overtake her. “Oh my god!” she cried out.
As she slowed her thrusts, the driver put his hands back on her hips.
“Oh, fuck,” she said, breathing heavy.
“Oh…” she said as he pulled her back onto his shaft as he thrust forward.
“Fuck…” she panted.
“Me…” she whimpered.
Those three words were repeated until they became only two.
“Fuck me…” she said quietly.
“What was that?” he asked.
“Fuck me!” she said louder.
“Not sure I got that,” he said.
“Fuck me!!!” she screamed.
And he did.
He held her hips firmly and pulled her back against him as he thrust forward deeper and deeper. Her knees no longer touched the carpeted floor as he held her hips up, and her body convulsed through another orgasm.
He decided he wanted her dress off after all, but he didn’t bother with the zipper on the back.
She heard the first rip, and then the second before her eyes went wide and realized what he was doing. He had literally torn her dress off of her while he continued to fuck her. Trish pulled forward, sliding off his inhumanly rigid tool, but the driver quickly grabbed a handful of her hair, pulled her off the bench seat, and brought her face to his dripping cock.
He didn’t have to say a word. Trish instinctively took his wet tool in her mouth, permitting him to fuck her face for several seconds without a breath, letting his dick pop out of her mouth for a few gasps of air, and then repeating the process. He reached down between her tits and grabbed the front of her push-up bra. A firm tug tore the clasps free behind her back, and he tossed the garment aside. She undid the clasps of the garter belt, as she wasn’t sure that would break free if he tried to rip it off her.
Still holding a handful of her hair – which was now completely ruined – he led her to the back bench of the limo. He pressed a button in the arm rest and the center cushion moved out from the trunk area, creating more of a bed than a couch. He pushed her onto her back, and grabbed her left foot and pulled the stocking off. She tried to pull the right stocking off, but he swatted her hand away and ripped the nylon off, instead.
She leaned back on her elbows as the driver took off his shirt. He was more muscular than she would have imagined. A lot of gray hair. He moved forward and she prepared for him to take her by the head and face fuck her again. She would not have objected. She was growing accustomed to worshiping his magnificent cock.
Instead, he got on top of her and kissed her. He was practically smothering her with his size, but he went from her mouth, to her ear, to her neck, and Trish couldn’t help but run her fingers through his hair.
He moved from her neck, to her shoulders, and to her perky tits. Her nipples were hard and stood erect on her small breasts. The driver briefly bit and sucked on each one before moving lower down her torso. She knew it must have been cold outside, but she was sweating like she was running a marathon. Her heart rate was high, and her breathing was faster than normal. When his mouth reached her clit, she cried out with moans she didn’t know she was capable of making.
“I take it you’re turned on, now?” the driver said, wiggling out of the rest of his clothes.
Trish couldn’t seem to form words. His body was amazing. She looked at his face, and could have sworn she had seen him before, but quickly forgot as he moved on top of her. She laid back and pulled her legs back for him. She bit her lip as she thought he was about to penetrate her slightly sore, and hopefully still-lubricated asshole. Instead, he gently parted her labia with the head of his shaft before completely filling her pussy. She squeezed her tits hard, and rubbed her clit feverishly.
He let her.
He took one foot in his giant hand and brought it to his mouth. He kissed the soles of Trish’s feet before sucking on each toe. He gently let that leg drop and picked up the other, kissing her calf as he continued his slow, rhythmic thrusts. He placed her ankles on his shoulders, reached down and took a breast in each hand and squeezed gently. She put her hands on his and squeezed harder. He leaned forward, allowing her to lower her legs. She wrapped her legs behind his waist but he was too wide for her to lock her ankles behind him. She put her arms around his neck and kissed him.
“Fuck me again,” she whispered.
“Isn’t that what I’m doing?” the driver asked.
“You’re making love to me,” Trish panted. “Don’t pretend to love me. You ripped my clothes off. You don’t love me. You want to fuck me. You want to fuck my tight, 18 year-old pussy for all it’s worth. And believe me, I want you to. I want to feel you in my tight little ass, too. And when you’re done, I want to lick my shit off your fucking incredible dick.”
He leaned down and kissed her hard and pushed himself deeper inside her. He eased her back and put his large hands back on her small tits, gripping them hard enough to bruise.
“Dirty talk doesn’t make me come, sweetheart,” he whispered. “But it does motivate me.”
He increased his pace, and squeezed Trish’s tits hard enough to hurt. She bit her lower lip and then let out a deep breath.
“Come inside me,” she panted. “I want you to.” She looked down and could see her stomach rise and fall with each of his thrusts. He was big. The likes of Kyle were not going to do it for her, anymore.
He put his left hand around her throat and pushed her head back. He reached under the armrest to the right, bit off the cap to a tube of something, and squeezed the contents into her asshole. Her pussy contractions almost made him come right then. Almost. Trish panted hard as a second and third wave of orgasm left her gasping for air.
“And I thought that ‘wanting it in the ass’ was all talk,” the driver grinned.
She wasn’t sure what he had rubbed into her little rosebud, but whatever soreness she was feeling earlier seemed to have gone away. Trish lowered her legs and motioned for the big man to lay down. She knelt between his legs and rubbed her face along the bottom of his shaft and in his nut sack. She tried to push his legs back, but they were too heavy. He obliged by pulling them back for her. She licked all around his hairy balls, and even tongued his asshole for a few minutes to see if it might produce a reaction. He just smiled at her, patiently, as his majestic cock pointed skyward, as rigid as ever.
She kissed him from his hairy toes to his neck, sometimes sliding over his body and facing in different directions. He seemed to keep himself preoccupied by putting his fingers in whichever orifice of hers was closest. She noticed that he really liked kissing her legs and feet. She did have pretty feet, after all. Small for her height, but pretty – especially in high heels. She wondered why she didn’t wear sandals more often. “The things I think about when I’m about to get the shit fucked out of me,” Trish thought.
She positioned herself over his cock, not just looking at him, but locking eyes with him, as she lowered herself onto his shaft. It seemed a perfect fit for her stretched pussy, now. She bounced several times before repositioning herself in a jockey position. She then rocked back and forth, arching her ass just right for her to achieve the perfect position to come over and over again. She could do this all night. But, she realized she didn’t have all night. She had to get home. Tim needed to get home.
She pulled herself up off his manhood and grabbed as much of his shaft as she could while using her other hand on one of his huge pectorals to steady herself. She pressed the head of his cock against her anus, but couldn’t seem to get it past the sphincter. She changed her position again, back onto her feet, squatting over him. This time, she exhaled deeply as she lowered herself. The head went in with a little less resistance. She breathed deeply again, again locking eyes with the driver who was grinning back at her. She spit in her hands and reached down, trying her best to lube his shaft and try to take more of him inside her. She licked her hand a little more.
“Strawberries?” she thought.
She wasn’t in pain anymore, but it seemed as if easing herself down wasn’t going to do the trick. She made sure he stayed inside her as she once again leaned forward, using her shins for support. Her shins didn’t complete touch the seat, as the driver’s body was too wide. It was more like she was riding a horse bareback, and supporting her weight with her inner thighs. No matter what she did, though, she couldn’t seem to get enough of him inside her to actually be fucking her.
“Mind if I drive?” the driver grinned at her.
Trish lifted herself off his shaft, and her anus instantly stung.
The driver reached for the tube of strawberry-flavored anal lube and rubbed more on his shaft, then sat up, motioning for her to turn her back to him. He spread his legs and she shimmied between them, backward, until this helmet was once again pressed against her anus.
“Put your feet on my knees, and lift your ass up. Lean back against me,” he said like he was talking her through disarming a bomb. She did as he directed.
“Now, reach down and put my dick in your ass,” he said almost impatiently.
She did as he said, and two inches instantly went inside. He reached under her ass cheeks, supporting her weight.
“Holy shit, you’re strong,” Trish said, amazed, and enamored once again with the feeling of his cock inside her.
The driver lifted and lowered, lifted and lowered, easing in a little more of his meat up Trish’s back door each time. She looked down and couldn’t believe how erect her nipples had become. He was easily sliding six inches of his shaft up her ass with every thrust. She relaxed her shoulders against his chest and reached down to rub her clit.
“Better?” he asked as he felt her hips arch back and forth in time with his thrusts. He was still doing most of the work by supporting her weight with his arms and hands, but there was not doubt she was fucking herself in the ass with his dick.
“Oh yeah,” Trish said. “Much. How about you? Does my butt feel good?”
“Oh yeah,” the driver replied in her ear. “I’m getting close.”
She continued easing more and more of his throbbing dick in her ass for another five minutes before realizing he was no longer supporting her weight. It was all her. Her leg and ass muscles swelled as she was in total control of the pace and how much of his dick she took inside her – which was at least seven or eight inches, but not all of him.
His hand reached under her arms to her tits, forcing her to stop rubbing her clit. She reached back and held his neck and head, touching his face, and putting her wet fingers in his mouth.
The driver pinched her nipples hard, then took her breasts in his hands and squeezed as he rammed his cock further up her ass. She didn’t know how she could possibly take much more, feeling like she could faint at any minute.
The rapid twitching of his cock deep in her bowels as he released his seed triggered her own orgasm.
“Fuck, yes!” Trish shouted, loud enough to wake the neighbors, if there were any.
She was still moving her hips up and down, rapidly, determined to make him be the one to say, “Enough.”
But he didn’t.
He had definitely come, as she could see it, smell it, but most of all feel it. She hadn’t stopped impaling herself on him, and he didn’t seem to have lost any of his erection. Instead of struggling, she was practically gliding up and down his shaft.
The second wave of Trish’s orgasm hit, and she almost lost her footing.
Tim was there to catch her leg, though.
“Tim?” Trish panted, but not stopping her downward thrusts on the big dick in her butt. “What are you doing…?”
She could only imagine what she must have looked like to him. She had to have been a complete mess. She was sure her make-up was smeared across her face, along with other bodily fluids. She was pretty sure she had come in her hair, and there was enough come around the pistoning shaft in her butt to cause it to froth.
Tim didn’t say anything as he turned to make sure he closed the limo door, and took off his tuxedo jacket.
The driver squeezed Trish’s tits to let her know he wasn’t finished, and Trish picked up the pace, fighting off another unexplained orgasm.
She thought she had closed her eyes and let her head fall back for only a minute, but when she open her eyes and looked down, Tim was inside her and leaning forward to kiss her. She was still rocking her hips, but now she had Tim in her pussy and the driver deep inside her ass. She then realized it wasn’t her rocking her hips, but Tim, as he held her legs up and back. She didn’t think he was capable of lifting her like that, but more importantly, she didn’t think his average-sized dick could feel so good inside her pussy. He was hitting her in all the right places. The feeling of the two cocks inside her was intoxicating.
“You’re…” Trish stammered, trying to say something between the wet fart noises emanating from below them.
“You’re…” she continued, “Okay with this?”
Tim just smiled and fucked her pussy as hard as he could. He knew he didn’t come close to the length of the driver, or the girth of Nick, but he didn’t care. Her pussy still felt good, and even tighter with a dick in her ass.
A few minutes later, Trish’s legs shook and she wasn’t sure if she was going into shock, coming, or pissing. She felt the cock in her butt once again erupt deep in her bowels, while almost simultaneously feeling the dick in her pussy release it’s own eruption of come inside her.
She leaned forward and kissed Tim hard on the lips. She was definitely cum drunk. She barely knew what she was doing or saying. One moment, she was kissing Tim with cum pouring out of her gaping pussy and asshole. The next, she was on her knees, in puddles of come, licking the driver’s still-hard shaft with her tongue and lips. She completely forgot where it had just been. Moments later, she was swallowing long spurts of come as the driver jerked off in her mouth. He came so much, she just opened her mouth and let her come all over her face, swallowing what she could.
The limo hit a few bumps in the road, and Trish opened her eyes to early morning sunlight.
“Where are we?” Trish asked, trying to sit up. She was still naked except for her high-heeled sandals. No sign of her stockings, garter belt, bra, or dress.
“We’re about a block from your house,” Tim said, fully dressed.
“What time is it?” Trish said, looking at the dried come covering most of her body.
“Early,” Tim said as he took off his jacket. “Put this on, just in case anyone is up.”
“My folks are going to be pissed, if they’re not already calling the police looking for me,” Trish frowned.
“No, they’re not,” Tim smiled. “My mom texted your mom and said we were going to watch the sunrise at our lake house. Spur of the moment thing, and not to worry as my folks were there.”
“And she bought it?” Trish asked.
“Yeah,” Tim said. “They just wanted to make sure you had a ride home, as they were going to run some early errands and let you sleep whenever you got home.”
The limo pulled up to Trish’s parent’s house. The driver politely opened the door for Tim and Trish, and Tim walked her to the side door of the house, spending as little time as possible in the view of the neighbors. Trish checked the garage and could see both cars gone. Nobody was home, as far as she could tell.
“Well, Tim, thank you for a wonderful evening,” Trish smiled.
“Best prom ever?” Tim asked.
“Best prom ever,” Trish agreed. They kissed for longer than their usual good-bye kisses. She felt a tingle in her nether-regions. “Did he just do that with a kiss?” she thought.
She turned to walk through the door, and Tim tapped her on the shoulder.
“Sorry, but I’ll need that back,” Tim pointed at the tuxedo jacket.
Still outside, she took off the jacket and draped it over Tim’s arm. Then, she turned and walked through the door, naked except for her high-heeled sandals and her little handbag holding the house key and her phone.
Once inside, she closed the door, and bent over to take off her sandals.
She walked through the house, naked, upstairs to her bedroom. As she walked down the hall, the door across from hers opened.
“Good prom?” Sherry gawked. Trish’s sister had seen her naked before, but she probably hadn’t seen her naked and covered in dried come.
“You could say that,” Trish smiled. “I’ll tell you all about it after I take a shower.”
“Cool,” Sherry said. “I’ll make some breakfast.”
Tim went back to the limo and sat in the front passenger seat.
“Well, that was fun,” Tim said.
“Yep. Sure was,” the driver said, grinning. He waited a few minutes, and then asked, “So, you think she’s a keeper?”
“I never met anyone like her,” Tim answered.
“Well, I wouldn’t be in too big a hurry with her,” the driver said. “Give it some time, just to be sure this isn’t some phase she’s going through.”
Tim nodded and sat quietly as the limo continued toward his parent’s house. He felt the limo come to a stop and opened his eyes.
Home. As he opened the door, he turned and looked in the back of the limo, and then at the driver.
“Good idea grabbing mom’s old phone before we left,” Tim said. “And thanks for driving us last night.”
“No problem, Tim,” the driver said. “No problem at all. Go get some rest. I have get this thing cleaned up before I turn it in, but I should be back in an hour or so.”
Tim watched as the limo drove away, and looked forward to a hot shower and a very long nap.
Trish felt like a new girl after her shower. She cleaned up well, and a little foundation covered the dark circles under her eyes. She had bruises on her breasts, calves, and butt cheeks. Some light bruising on her neck, but her hair, make-up, and a hoodie covered all of it. She was happy the cold weather was going to last a few more days, as it gave her an excuse to wear baggy clothes. She gave Sherry a run-down of the prom itself, but not much after. She decided to stick with the story of the lake house sunrise, and that she ended up getting mud all over her dress.
Tim was going to have it dry-cleaned, which would ultimately result in the dry cleaner misplacing the dress, and so on.
As for the bruises… she got rough while making out with Tim, and he got rough with her, but they both enjoyed it.
Sherry didn’t believe half of it, but that was okay.
The next day, Trish asked her friend-of-a-friend to find her a bigger butt plug, and some of that strawberry-flavored anal lube.
—
Trish heard the hotel room door across the hall click shut. She quietly stepped off the bed and looked through the peephole.
“Oh my god, she’s wearing the outfit,” Trish whispered.
Trish’s husband said the main contact was named Merv. Merv and his band of dirty old men had interesting tastes, and asked that “the girl” wear a very specific outfit made up of high-heeled sandals, a mesh top that was completely see-through, a matching mesh skirt, nipple clips (if the nipples weren’t already pierced), and satin crotchless panties. And, of course, a fox tail butt plug.
Trish had her husband request that as it was their first time enjoying each other’s company, everyone wear Columbina masks until she was comfortable with them knowing her, and they were comfortable with her knowing them. Trish didn’t charge for these little parties, although donations were welcome. She made sure there were rules, and that everyone involved could be trusted. This was her first time, though, experimenting with the idea of a stand-in for her.
Mags walked toward Trish’s door and then, as fate would have it, she turned and walked toward the other door.
Trish hurried to the wall shared with the next room, pressing her ear to it, and trying not to breath.
There was a knock at their door, some quiet conversation, some rustling of some sort, and then…
“Gentlemen, may I present, Trish,” Merv said. “Trish, we’ve all been checked out and are disease-free. You may begin whenever you’re ready.”