Piper and the College Boys

by Little Bree

Copyright© 2010 by Little Bree

Erotica Sex Story: Fifteen year old Piper is tired of being the ugly duckling in a blended family with two gorgeous stepsisters. After she meets an older guy who appreciates her geekiness but thinks she's 18, she spends a wild night losing her clothes and maybe even her virginity while his horny roommates gawk and applaud!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Consensual   Reluctant   Drunk/Drugged   Heterosexual   First   Petting   Cream Pie   Exhibitionism   Voyeurism   .

Author's Note: As you can probably tell from the story codes, this is a happier story than others I've written. If you're a fan of gang rape and exploitation, I've laid the ground work for sequels that you might like better, but I'm not certain those'll ever get written. I'm fickle that way.

Impatient readers be warned: There's a lot of build up and character development at the start of this one. If you need to cum before the end of a commercial break, look elsewhere fast. The dirty parts don't even start, if you're reading this in MS Word in 10 point Courier New, until page 11 of 19. I enjoy the sex more if the characters are well established, and my goal is make them endearing enough that you have some emotional investment in the naughty parts. Otherwise, I'm writing novelizations of stories that would be better told visually, and that feels like a waste of time.

As always, feedback very appreciated. Other authors tell me that you almost never hear from readers, and I've found that they are correct. If ASSTR's hit tracking is correct, I've heard from fewer than 1 in 1000 readers. Either my stories are terrible, and need improvement (in which case, be charitable and tell me how!) or many people are too lazy to thank a girl for making them cum. ASSTR even gives you an anonymous form to use if you don't want to expose your "real" disposable-webbased-email-address.

Anyway, make love not war. Get help if you are actually considering sex with kids, and if you're not 18 or you're in a country where this sort of thing is illegal don't read it.

Thanks Bree

Piper felt ridiculous. The dress, a "wave bodice dress" according to the tag, was a creamy purple shade ("bright lilac") that Marissa had cleverly dubbed creamed-muppet, and, without straps, it hung over Piper's not-ample chest in defiance of gravity. She couldn't imagine wearing it anywhere outside the store she was standing in, ever. After 3 hours in dressing rooms at J Crew, the Limited and Abercrombie, all she wanted was a pair of sweats.

Of course, she couldn't let on that she was miserable.

Her stepmother, Debbie, was eyeing the purple monstrosity up and down with the sales girl. "It's a bit loose up top," she said, tugging at the material as though to emphasize the location of Piper's inadequate boobs. "Maybe something with a halter neck would look better? Like the cute red one we saw? Why don't you try that one on, Pipes."

Piper screamed inside and slunk back to the dressing room, crossing paths with her stepsister Madison, who emerged looking fantastic in the same creamed-muppet dress. Piper had no idea why her stepsisters even bothered trying clothes on; they could both make burlap sacks look hot. Designers had yet to stumble onto an outfit that would make them look fat or flat chested.

Piper was not so lucky. She wasn't ugly by any means, but people would tend to describe her using words like "mousy", "pale" and "tiny." She was 3 months older than Madison, but a full 7 inches shorter and 2 cup sizes smaller. Because nature liked it when she suffered, she also had virtually unmanageable hair (currently a homemade shade of red because why not?) and requisite ugly-duckling glasses.

"Miserable yet?" asked Marissa as Piper traipsed back to the dressing room with the ugly red dress under her arm.

"No way," said Piper, dryly. "This is ever so much fun."

Marissa laughed. "You're the one who wanted to come." The older girl spun around to get a look at the way the yellow skirt molded to her perfectly shaped butt, then shifted back around as if to be certain it still looked amazing up front.

"I believe I must have been drugged," said Piper. "No way I said that on my own."

She had wanted to come, though. She'd wanted to come badly, mostly because they'd all assumed she wouldn't want to come.

A week ago, for Christmas, Debbie'd stuffed gift cards in each of the girls' stockings. Marissa and Madison had ones for Abercrombie and Victoria's Secret. Piper's were from Amazon and Barnes and Nobel. It was a nice gesture, getting her cards for stores she actually shopped at, but it'd pissed her off just the same. She wasn't some sort of butch-lesbian tom-boy; she was a girl, too! Just because the other two were so much better at it didn't mean Piper didn't like to look pretty, too.

Which is why she'd insisted on coming when the three of them went shopping. Debbie'd been shocked, but once she realized her stepdaughter was serious, she'd eagerly embraced the opportunity to play dress up with a new human-doll.

"Have you found anything you actually like?" Marissa asked, moving on to a short blue dress that looked to Piper more like a cover-up she'd wear to the beach.

"There was one top at J. Crew that didn't make me look flat chested," Piper said. "I can't remember if Debbie liked it."

Marissa giggled. "You obsess like you haven't got boobs at all," she said. "You're still growing, too."

"I'm 15," she said, "I think I'm done growing." Her other point wasn't totally invalid. Piper's 32Bs, in any other family, would look respectable and even chesty. Beneath the top of the red halter dress, though, they disappeared completely.

Marissa turned a head to look at the new outfit. "No way," she said. "That's a train wreck."

Even in the right size, it looked ridiculously big on Piper, like a little kid dressed up in her mommy's clothes. "It'd still look ridiculously hot on you or Madison," she said resignedly as she started tugging it off.

Marissa rolled her eyes and helped her stepsister out of the dress. "I think your first mistake," she said, "is letting mom pick things for you. Wait here and I'll put something together."

For a long several minutes, Piper sat awkwardly alone in her panties and bra. She wondered if there were security cameras in there. They weren't hanging down where she could see them, but they might be hidden in the ceiling. Marissa'd been almost naked in there for 45 minutes, and there was no way male security guards weren't watching that show. Piper waved at the ceiling to say hello, amusing herself greatly.

Madison came back in with a fresh set of dresses to try on but just smiled and rolled her eyes at her sister.

"I'm just being sociable," said Piper, without further explanation.

Marissa returned with a pile of clothes. "Here," she said, "this might be more your style."

Eight outfits later, Piper concluded that "her style" also looked ridiculous.

After lunch, on the realization that the other three intended to spend several more hours trying on clothes, Piper's resolve broke and she agreed to meet them by the Orange Julius at four o'clock. A symbolic point wasn't worth three more hours of torture.

Debbie'd been reluctant to turn her stepdaughter loose in the same cut off skirt and vintage t-shirt she'd previously described as "ratty." She'd waited years for the chance to put the girl in a country-club ready outfit, and she hated to miss the opportunity. Without Madison's suggestion that they could just pick up anything Piper might like and return it if it didn't fit, it might not've been so easy!

There wasn't a bookstore in the Twin Pines Mall, but on the less crowded third floor—where the foot traffic was too low to sustain any of the trendy stores—Piper found enough to keep her amused. The pet store lady let her sit forever with the cutest cocker spaniel, and the bored sales clerk in the billiards store taught her to play darts.

The used CD store, though, was the high point. Charles Mingus' Epitaph concert—complete with his angry rant that the audience should demand a refund—for four bucks! It was a homemade bootleg, of course, but a ridiculous find. It was the sort of thing you couldn't even find on the internet.

The sales clerk cocked an eyebrow at the price tag when she put it on the counter. "We got this for four bucks?" he said.

"I know!" said Piper. It was good to have a fantastic price acknowledged.

"Shit," he said as he rang it up. "You lucked out."

Piper beamed. "Go me," she said.

He smiled up at her. "You're into jazz?" he asked, disbelieving.

"Totally," she said. " I've been looking for this one for forever."

"Wow," he said. "That's a first. Usually pretty girls only buy the jazz for their grandfathers."

Piper blushed. He was easily 5 or 6 years older than her, and it was probably just politeness, but after the traumatic morning it was nice to be called pretty.

"And," he continued, "when they do buy it, it's always Kind-of-fucking-Blue."

They both laughed. It was like a jazz-geek secret handshake, bonding over the sell-out Miles Davis. Real jazz fans didn't dislike Davis, but everyone knew Kind of Blue was the go-to album for neophytes and douchebags trying to look sophisticated.

"I almost want to take your picture and post it on the wall," he said. "Cool-jazz chicks are like Big Foot. No one is ever going to believe me."

Piper giggled more. He was definitely older, but he was cool. For a slightly chubby guy, he was even sort of cute, with a fuzzy beard and big brown eyes. Like a teddy bear, she thought.

"I can come back with witnesses if you want," she said.

"Oh, you better come back," he laughed. "We need more of your kind. I die a little inside every time I sell some poor kid a Miley Cyrus album. It's so hard to watch, you know?"

Piper shook her head solemnly. "When will they ever learn," she sighed.

"But coming back isn't good enough," he said. "The other degenerates here will think I put you up to it."

"You do seem like the sort that'd pull something like that."

"Don't I? I know. I would too, I just didn't think of it earlier." He stroked his beard, pretending to be deep in thought. "No, though, what I think we need to do is, you know, trade phone numbers and that way I can call you and you can verify the story."

Piper smiled wryly at him. "Hmm," she said, "wouldn't they think you put me up to that too?"

"Um, possibly, but then..." he stopped for a moment and reconsidered his plan. "But THEN," he continued, before making a show of stopping and backing up again. "Um, yeah, good point.

Piper giggled and twirled her hair absently, genuinely amused.

"I don't suppose you want to just give me your phone number and let me think of a clever pick up line later, do you?" he asked. "I promise, it'll be like the best line you've ever heard. I just need some time to work on it."

Poor fair-skinned Piper hoped she wasn't visibly blushing. She knew she was, but she hoped she wasn't. He was hitting on her? That never happened! Her brain repeated "ohmygod" on a rapid loop.

"Um, sure," she said with a smile after what she hoped wasn't too long a pause. "But it better be good. I'm holding you to it!"

"I'm George, by the way," he said as he found a scrap of paper and a pen.

Piper was shocked at how nervous he seemed. How the heck was HE nervous?

"I'm Piper," she said. "It's nice to meet you."

"You too," he said. "Haven't seen you around before. You go to Pinecrest?"

Piper froze. The State University at Pinecrest was the liberal arts college that dominated the southern edge of town. It was the only college within even reasonable commuting distance. He somehow thought five-foot-and-flat-fifteen-year-old Piper went there? Obviously, he was a shitty judge of age, but Piper didn't want to ruin this.

"Yeah," she lied. "I do."

"Very cool."

"But I live off campus," she said, maybe too quickly.

"That's awesome," he said.

"Yeah, I rent a room from this family. They're sort of cool."

"Great," he said.

"But yeah, it'd be good cause I haven't really hung around on campus very much," she said. "So I don't know that many people. Because I'm mostly off campus. Which is why you probably haven't seen me there before."

George didn't speak for a long pause, as if he was waiting for the too-long-explanation to keep going.

"So I'm not working Friday," he said at last. "And my buddy just sent a bootleg of the Lester Young jam from the Library of Congress. Wanna hang out and give it a spin?"

"Sure!" she said.

"Great," said George. "I'll call you to work out the details."

"Ok," said Piper. She was smiling dumbly, and thinking that she should say something clever and cute, but her head was swimming and she couldn't come up with anything. If another customer hadn't come to the counter to pay, she may not have remembered to leave.

"And don't drink anything unless you opened it yourself."

Marissa was full of important pointers like that. En route to Pinecrest she'd already instructed Piper on the many ways to incapacitate a would-be-rapist, how to appropriately scream for help (yell "fire" not "rape") and the many ways she should never flirt. "I can't believe you wore a skirt," she said. Skirts were apparently taboo on a first date, but Piper thought she looked good in it.

"Relax," she told her sister. "We're just listening to music. Nothing is going to happen."

Marissa frowned sternly. Debbie or her dad would've been worse, Piper knew, which is precisely why she'd asked Marissa for the ride, but her sister worried way too much.

George was waiting on the porch of a big old house when the girls pulled up. He smiled and waived.

"Remember to call if anything goes wrong," Marissa reiterated.

"Yes, mom," Piper teased as she hopped out.

"Who's the blond?" asked George as they watched her pull away.

Piper's stomach sank. This was supposed to be HER guy. He wasn't supposed to be looking at Marissa. "My roommate," she said.

"Huh," said George. "I didn't think you'd be hanging with the cheerleader type."

Piper would've jumped up and down. He'd seen the gorgeous blonde and still preferred the mousy redhead. It felt like victory!

"She's nice," said Piper. "For that sort, anyway."

He lead her inside and gave her the grand tour. George shared the house with 5 other guys, all of them students. It was a bit run down and they obviously didn't do much to maintain it, but you could tell it used to be a really nice house. "I cleaned up 'cause I knew you were coming over," he said sheepishly. "You should've seen it before."

Piper giggled. She was way too nervous to care.

"Do you want something to drink?" He asked.

"Sure," she said.

"Anything in particular?"

Eager to not be difficult, she'd offered up a noncommittal "whatever you're having," and George returned with a bottle of white wine from the fridge. Piper gulped. It hadn't even occurred to her that he meant alcohol. She'd never actually drank wine before, but she figured she was trying to act like a college student and a little wouldn't hurt.

For an hour, they sat on the couch and listened to Lester Young while they drank the wine. The music wasn't good so much as rare, and Piper had to force herself not to wince when she sipped her wine. Still, she was having fun. George was sweet and funny, and said things about the music that were actually smart.

More importantly, she couldn't get over the way he looked at her. Guys looked at Marissa and Madison like that, but never at her. There was something intangible about it, but it was focused and wanting—like the only thing he wanted to look at in the world was her. Old people and grandparents can call a girl pretty, but a guy who looks at you like that has to mean it. For the first time in her life, Piper felt beautiful.

George refilled her glass again and fetched another bottle. She'd never been drunk, of course, but this felt pretty ok. Better take it slow, she thought.

"Do you like the wine?" he asked.

"Yeah," she said. "It's really good."

"I'm glad you like it," he said. There was an awkward pause as he clearly had no idea what to say next. "You look really pretty," he said.

Piper just blushed and smiled.

"I love your hair," he said as he reached over and brushed a stray lock from her cheek. "I never dated a red head before."

She waited for the joke about the carpet matching the drapes, which she'd heard at least a million times, but he apparently knew better.

His hand drifted over until he'd put an arm around her and tugged her closer on the couch. Up next to his stocky frame, she felt so little. She knew she had to be careful, because she must have been at least a little drunk, but she hugged him and snuggled into his chest.

Then he leaned her back and kissed her.

It was electric. Her whole body tensed at once as she felt his lips parting hers, and his tongue slipping so confidently against her own. His beard tickled her face, and he tasted like wine.

George pulled her up and onto his lap like a little girl without ever breaking the kiss. She felt his hand resting on her knee, and despite Marissa's warnings, she let it stay. She liked it there. She wanted it there, and found herself wanting him to touch her more.

It was hard to say how long they kissed. Piper could've stayed there on his lap for blissful hours or days. At some point, though, she felt his hand on her thigh above the hem of her skirt and sliding higher. He let his finger tips traipse across her bare leg, giving her goose bumps with every touch. When he finally reached her panties, Piper reflexively parted her legs, seemingly inviting him to feel her delicate pussy.

George kissed around the side of her neck and nibbled her earlobe as he tugged aside the cotton panties and stroked her wet lips. Piper knew better than to let him keep going, but she knew she wanted this more than anything in the world right then. On pure lusty instinct she found herself bucking her hips ever so slightly forward, into his hand. With little other prompting he'd found his way into her pussy, and begun to circle two fingers around her clit.

Boys had never played with Piper like that before. The one guy that had ever even touched her down there was too quick and too clumsy. It had been more irritating than sensual. Whatever spot George had found, it was the right one!

He paused for a too-long moment to tug her panties all the way down and off through the bottom of her skirt. Then he turned her around in his lap so that they were facing the same way, and her legs were spread lewdly onto each side of his legs. At the new angle, George could push a finger deep into Piper's snatch while still teasing her clit with his thumb. It was an incredible sensation, unlike anything the teenager had ever felt before!

George kept kissing her neck. "Do you want to go up stairs?" he whispered.

Piper knew better than that. She loved the way he was touching her, loved the way he made her feel, and wanted nothing more than to just let him have his way with her. She wanted it! But she knew she couldn't. Huge sluts will sleep with a guy on the first date, but even they don't lose their virginity like that. "I shouldn't" she whispered back.

Obviously, George was disappointed, but he didn't pressure her. He let up on the fingering and pulled her in close again, snuggling next to her on the couch. He poured them more wine. "Sorry," he said, "I guess I got a little carried away."

She hugged him tight and kissed his neck. "I liked it," she said. "A lot. I'm just not ready for, you know, that yet."

He stroked the small of her back and kissed her forehead. "The curse of dating one of them classy broads," he teased. "I'll wait until your ready, gorgeous."

The music was still going, but Piper wasn't listening. He really liked her! It wasn't even like Marissa said, how guys just wanted sex. She told him no sex, and he was still into her. Maybe it was a trick, because she wanted him more now than ever, but what a trick that'd be.

"Hey George-Ay!" came a voice from the kitchen. "What's going on my man?"

A skinny boy in slacks and a stained tuxedo shirt walked into the room, but stepped back when he saw Piper snuggled up next to George. "Oh jeez," he said, "I didn't know you had company. Sorry about that." He extended a hand to Piper, "I'm Mike," he said.

"Mike, this is Piper," said George, taking care of introductions. "He's my roommate."

"Nice to meet you," she said politely, shaking his outstretched hand.

"You too," he said. "You guys just chilling on some wine?" he asked.

Piper was mortified when she realized that her panties were laying conspicuously on the coffee table, barely blending in with the magazines. She couldn't grab them back without drawing more attention, so she just prayed he didn't notice.

"Yeah, just some jazz and some wine," said George.

"Nice," said Mike. Whatever awkwardness there was in the room, he seemed to be missing it. "You guys doing anything later? I got some sweet stuff from this dude at work. I was thinking 'bout putting on some of that Davis stuff of yours and doing a bowl. You want in?"

"I don't know," said George, "What do you think, Piper, does that sound like fun?"

Piper, of course, had no idea what she was supposed to say. She wanted to hang out with George, but she also wanted to be cool and into the things he wanted to do. If he wanted to be alone, that's what she wanted, but if he'd decided this'd be more fun she wanted to do what he wanted. It was a very tough call and she was hoping for a cop out. She wondered if he'd let her go call Marissa.

"Whatever you want to do is fine with me," she finally said, very proud of herself.

"Great!" said Mike. He apparently inferred that George was game. "Let me get out of the waiter-suit and make some calls. We're gonna party!"

"Sorry about that," said George as his roommate disappeared up the stairs. "You sure this is cool?"

"I want to do whatever you want to do," she said, very coyly.

"You are one cool chick," he said with a smile.

The "Party" wasn't really a party so much as five guys (and Piper) sitting around a living room with a stereo and a bong. Mike had spent an hour trying to round up some "hot chicks" to come hang out, but it was not a fruitful effort. As they pushed play on Miles Davis' Bitches Brew, Piper remained the only girl in the house.

Feeling awkward and out of place, she'd been too shy to turn away the bong when they passed it her way, but she'd been forced to confess, as she fumbled with it, that she'd never smoked pot before. George, thankfully, was happy to teach. The first few efforts ended with gagging and watering eyes, but the guys ultimately clapped and cheered for her successful inhaling. She stood to take a playful bow.

Piper was still feeling the four glasses of wine, which had stealthily but certainly put her tiny body over the legal limit, but the pot mellowed her out and made her feel very surreal. It was very mellow, but not sleepy. No wonder people like this stuff, she thought.

She smiled dopily at George, who smiled back, and then she slid onto his lap. There was room on the couch, they both could see, but she liked sitting on him. She wondered if she was being as cute as she felt like she must be.

"I don't know, man," said one of the guys on the floor, a long haired blonde guy named Pete. "I'm just not digging the music. Its all just sort of horns and shit. Who really likes this, man?"

George seemed to ignore the slights on his music as he dreamily stroked Piper's arm. She regretted ever agreeing to hang out for the party, because he obviously would've preferred to take her somewhere else.

"Chicks, man," said another guy. He was a Hispanic boy who probably had a real name, but they all called him Speedy and that's how they introduced him to Piper. "Chicks get all hot and wet over shit like this man. It's like panty remover."

"For real, yo?" asked Pete.

"For real," said Speedy.

Pete took another hit and sat for a long moment thinking deeply. "What the fuck man, how do you know that? Ain't no chicks getting' down with you."

"Fuck that, man," said Speedy. "I'm getting plenty. It don't matter though, I know it's true. Mike, you tell him."

"It's true," said Mike on the inhale, as he took another hit. He passed the bong to George before he finally exhaled. "Totally true."

"What do any of you pansies know," said Steve. Steve was tall and black, with a deep baritone voice. He was too cool for the floor, so he got the lazy-boy. "You got a cute little thing sitting right there in Big G's lap," he said. "Why don't you ask her?'

"Oh shit, yeah" said Pete, "um, redhead girl ... um ... Piper! Piper, does this shit like make girls horny and shit?"

All eyes turned to Piper, who'd been happy to just blend into the background. She was, predictably, bright red as five college men eagerly awaited an explanation of what turned her on.

"Well," she said, squirming. "Sometimes. I think. I guess it depends on the girl."

George handed her the bong, and she took another hit. Her head was absolutely spinning now, and she knew it was a horrible idea to take more.

Most of the guys were willing to leave the answer well enough alone, but Pete was too far gone for that.

"Well what about you?" he said. "Does it make you horny?"

"Dude," objected George, "I'm sitting right here."

Piper appreciated the way he leapt to her defense.

"What, man? I wasn't hitting on her or nothing, just a simple question." Pete seemed genuinely confused by the bad reaction.

"I thought it was an excellent question," said Mike. "What up, Piper? We need to know this stuff."

Once again, Piper turned red.

"Oh shit," said Mike, "She blushes so cute. Are we embarrassing you?"

"A little," she said.

"You'll have to excuse them," said Steve. "They don't usually get to talk to pretty girls."

Piper could get used to this pervasive belief that she was a pretty girl.

"Of course we don't," said George. "At some point, they meet our friends and run away screaming."

Everyone laughed.

That might've cut the tension, but Pete wasn't having that. "Seriously, though, man, I gotta know this shit, yo. It's like life changing if chicks get all sloppy for gay ass music, you know?"

"You could buy a record and experiment," George said. "I actually know a place where you can buy that sort of thing. Shitty management but excellent staff."

"For serious, yo, I just wanna know yes or no."

"Fine," said Mike. "Speedy, is your pussy wet? Pete needs to know."

"You're hilarious, man. Absolutely hilarious." Speedy was mellowing out and taking another hit.

Pete was determined. "Come on, George. She's your bitch, just reach up there and check so you can tell me yes or no, yo. I can't afford to be buying records and shit if don't work."

"That does seem reasonable," said Mike, "it is for science."

"Yes," said Speedy, "for science!"

Piper was just stuck blushing. The attention was overwhelming, especially on top of the booze and the drugs. The whole thing felt so surreal and silly. She was still plain old short pale Piper, but these guys were treating her like a super hot girl. She wondered if this was what every day was like for Marissa and Madison. She determined stop thinking about the pair of them, because they weren't there and it was her turn to be the sexy girl.

She spun herself around and looked doe-eyed back up at George. A mischievous smile curled across her lips. "Well," she said, "if it's for science."

George's eyes opened wide with surprise, but he smiled too. "For real?" he whispered.

Piper just shook her head yes in giddy agreement. The boys all watched intently as George slid his hand up Piper's skirt to feel her pussy. "Oh my," he said as he too blushed, "this one very wet little girl!"

There was another cheer. Piper was already incredibly turned on, but the attention made her so much hotter. Having gotten away with the public display, George didn't let up. He kept his hand up her skirt and very casually played with her pussy in front of the boys.

"Man, I wish I had a chick that cool," said Pete.

"Hells yeah," said Speedy, "You done good with that one, G-man."

They smoked some more and switched discs, tossing on Lee Morgan. Piper'd never had an orgasm before, but George was achieving things that felt a lot like what she'd always expected. It took all of her will power not to scream at points, and even more to keep from dragging George to his bedroom. She was getting by just squeezing his free hand, tighter and tighter as he drove her wilder and wilder.

"Whoa," said Pete as he looked up at Piper. "Is he still like fingering you and shit?"

Piper was too breathless by that point to speak, but she smiled big and nodded yes.

Speedy, lying on the floor, sat up to look for himself and all the boys were soon openly gawking as George fingered his date.

"Piper, you are like the coolest chick ever," said Mike.

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