Kim Gets Off to College Ch. 02

Kim was at the prom, dressed in a black tuxedo with a royal blue bowtie, and Laura Wetherbee was all over him. She was dressed in a pink backless dress, with a short skirt, and her legs were silky smooth, shiny and beautiful. She led him away from the other smokers who stood outside the dance, around the corner.

Once they were out of sight, she leaned against the railing and lolled her hips, slightly spreading her legs as she reclined.

Kim kissed her, passionately, pressing his body against hers as she lifted her bare leg and wrapped it around him.

Kim put his arm around her and her bare back felt hot on his hand. He reached further, until he was reaching inside the dress, just an inch or two, and gently stroked her skin with his fingertips.

"Take off my panties," Laura said.

"But they're right around the corner-" Kim tried to protest, pointing vaguely in the direction of the rest of the prom-goers.

Laura didn't say anything. She just started to pull up her already-short skirt, wriggling her butt back and forth while she looked up at him with her big blue eyes, biting her puffy lip.

She was a classic blonde, the girl he'd been obsessed with since the sixth grade. She'd never given him the time of day! And here she was. How had they gotten here? Something didn't add up.

Kim decided not to question it. He reached under her skirt and pulled down her panties. She spun around, bending over the railing, her panties still caught on her pink high heels, holding her feet together. Kim reached down with his hand and felt her, hot and wet, and ready. His fingertip slipped inside of her easily. "Please, Kim," she said, "Fuck me."

Kim quickly undid his belt and the fly of his black tuxedo pants. He released his rigid cock and rubbed it length-wise along the hot wet cunt perfect teen blonde. "Oh my god, Kim, yes!" she said, with her head dangling over the railing and her perfectly and expensively styled hair falling down over her face. Kim had never felt so turned on in his life, and he almost instantly felt the tingling sensation of an oncoming orgasm as he slowly rubbed his member against her.

"Mmmmm," she said, in a slightly different voice. A familiar one. "Good morning," she said again, as she smiled back at him. But it wasn't Laura. It was his sister, Diane!

It was a dream! A weird twist in the dream, Laura suddenly turning into his sister, but Kim was on the verge of an orgasm so he shrugged the transformation off. He just gripped her tighter and resumed his slow rub against her backside.

"Okay, then, don't stop..." said Diane, and Kim was starting to get confused, even as he was on the verge of cumming.

He suddenly realized that it wasn't only a dream. It was only mostly a dream. He really was in bed - with his sister - in their shared hotel room - and he was really rubbing his huge boner into the groove of her ass. Through her panties. And through the panties that he was still wearing after from their little drag dress up show last night. He was even still wearing a bra!

He stopped moving, mortified. "I'm sorry!"

"Shhh," Diane said as she backed up against him once again, "It's all right." She arched her back and rubbed her ass along his long, hard, dick, held tight to his own body by the soft, smooth panties. The soft skin of the underside of his dick was tickled by the slow caress of her soft ass-cheeks.

He wrapped his arms around her, and started moving his hips in time with hers. His hands grabbed her breasts, feeling her softness as she gasped and panted. Faster and faster they moved, as he got closer and closer and his dick got even harder and his balls tightened, and he came.

She could feel his semen splash against her back, and his arms relaxed from where he'd been tightly gripping her.

"Well," she said. "You'll have to remember not to do that to your new roommates. That might just give away the fact that you're a boy."

Kim rolled away from Diane. What had he just done? He'd just dry humped his sister, without even thinking about it!

"You must have been having a good dream," Diane said.

"Yeah," said Kim. "I guess I was. I was actually dreaming I was at the prom with Laura Whetherbee..."

"That blonde you were always in love with?" Diane asked. Kim winced at the description.

"Yeah," he said. "But she would never give me the time of day."

"Weren't you friends?"

"Well, yeah," he said, "but only friends. She didn't, I guess, take me seriously as a man."

"Then it's stupid for you to say she wouldn't give you the time of day," Diane smirked. "That expression means that somebody wouldn't even respond if you asked what time it was, like they have total contempt for you and pretend you don't exist. Don't you know that? Aren't you supposed to be smart? How'd a lunkhead like you ever get a scholarship to girls' school anyway? Must be affirmative action run amok."

Kim grimaced. Girls' school. How had it ever slipped his mind for a moment? Here he was, his entire future riding on a valuable scholarship he'd won, but at a school that only allowed female students! Only his stupid name, given to him by parents who had no regard for the idea of growing up without being mocked, had allowed this mistake to happen in the first place - and somehow he'd allowed his sister to talk him into the idea of disguising himself as a girl! Every day, for the entire school year!

She had a point. This was the only way he could afford a college education. If he showed up and revealed he was a boy, they wouldn't even let him into the school, probably! He'd have to drop out and get a job, save up money to go to college next year, maybe, at a state school, with lots of loans. He shook his head just thinking about his miserable other options, all so much worse than getting a full ride to the prestigious Sarah Van Hufferling college. And so he'd let her talk him into dressing in drag.

It was completely insane, and yet Kim had to admit that he'd looked incredibly convincing as a girl once Diane had made him over. A sexy girl, almost as beautiful - no, exactly as beautiful as his sister Diane. Diane was a successful rising television actress, pure glamour, with medium-length brown hair in a stylish cut, sexy dark eyes and full, luscious lips.

Somehow, the excitement of getting dressed up had made him horny as hell, and somehow he had wound up - oh god - giving a blowjob to a dildo. And letting Diane, his own sister, suck his cock.

Kim's face turned red and he held his hands to his face as he thought over his actions.

"What's wrong, Kim?"

"What are we doing? What are we going to say at Christmas?"

"Are you fucking serious?" Diane asked. "We're not going to say shit. This our secret, dummy. Good god, you better learn how to keep a secret if you're going to fool anybody at this school for more than two seconds."

"Will it even work for two seconds? That was fun last night, but I feel like anybody who sees me will know..."

"I guarantee you it'll work, because you're going to look fabulous."

Kim sat up in bed and saw himself in the mirrored door of the closet. He looked - he still looked just like a sexy girl, the morning after. His hair was wild, and his eye makeup was smudged and raccooned. His bra was still in place, and his false boobs were still in place and looked real. He looked just like a real girl.

"I did look good."

"You still look good. Makes me hot just thinking about it. Oh, god. Look, I know you just came, but are you ready to go again? Let's fuck before I start you on makeup academy."

With that, Diane reached for his cock, which swelled immediately at her touch. But Kim got up and stepped away.

"We can't - do that."

"What, because I'm your sister? I think most people would already frown on what we did last night, or, you know, five minutes ago. Might as well go all the way, right? Come on, I'm crazy horny. It's not a big deal, really."

"It is, though-" Kim continued. "It's not even that, it's just-" and Kim stopped talking. His big green eyes looked at the floor.

"Are you - you're not - you're a virgin?" Diane asked. She sat up in bed, revealing the top half of her body, covered in a tiny tank top, which was pulled askew, revealing her left nipple. Kim's eyes were drawn up to it.

"Yeah, uh, technically, yeah," he mumbled.

"What do you mean, technically? You've never come inside a girl?"

"Or been inside at all."

"Did you ever get a blowjob even?"

"Not until last night, from you."

"Wow, really? But seriously, why did you say technically? Did you fuck some chick in the ass? One of those Christian bitches?"

"No - is that a thing?"

"You haven't heard of that?" asked Diane, laughing. "Oh yeah. Those stuck up idiots think that Jesus will still think they were good girls, cause all they'd been doing was ass-fucking all over the place but their pussies were nice and clean. Talk about getting off on a technicality!"

Kim laughed. "Getting off on a technicality, that's funny."

"I didn't mean it like that," Diane squealed, punching his arm. "But they're so stupid. Like, I discovered a bonus hole to offer up so I could keep my boyfriend and my 'technical' v-card all that same time!!"

Now Kim laughed. "Like, to circumvent God's salary cap."

"I don't get what that was. Was that sports?"

"Yeah, it's sports."

"Kim, I gotta tell you, you're a smart guy. The smartest guy I know. But you gotta learn to stay in character."

"I'm not an actor, though," Kim protested.

"Actress, you mean," smiled Diane.

"I'm not an actress, either. I'll never be able to pull this off. Not really."

"Well I'm a great actress," said Diane, "Trust me, you don't start booking stuff right when you arrive in Hollywood like I have just by looking hot. And I know you've got acting talent, too, we've got a lot of the same DNA. It's inevitable. You just haven't developed it yet. But I'll teach you. Lesson number one: stay in character. Don't talk about sports."

"Some girls like sports."

"Girls don't talk about sports amongst themselves. I guess if you wanna talk about sports to meet guys, that's a valid tactic some chicks take but I've never been that desperate. You're not gonna have time for sports. What good has knowing all about sports ever done you anyway? If girls like sports so much how come your amazing sports knowledge ever led to you losing your virginity?"

Kim's cheeks reddened. "It wasn't cause I like sports that they don't, like, find me attractive or see me as a sexual object. Is it? No, it can't be that! I don't know what I'm doing wrong."

"Well whatever it is you're not doing it anymore. Now you're doing all new, girly stuff. And honestly, you don't need to be ashamed about being a virgin."

"I am ashamed, though. It feels like this important accomplishment as a man that I've never done."

"Well, we could fuck right now, it'll clear that virginity right up."

Kim shook his head. "I don't want to lose it that way. As a pity fuck? From my sister? No," he said, turning his chin to the floor, afraid to meet his sister's eyes. ""I want to, I don't know, earn it?" Kim looked up again, and saw himself in the mirror - a now distraught young naïf. "But how am I gonna ever get laid now?"

"As the only boy in an all-girls' school?" Diane asked dryly. "I'm not sure how, but I've got a pretty good feeling you'll figure something out. Just don't do like this morning and let your roommates wake up to you humping them and jizzing all over their backs. That just might blow your cover."

"I'm sorry."

"Oh, I don't mind. But if you're not gonna fuck me because of your lack of self-worth or whatever, at least hand me that dildo. I'm still all worked up!"

Kim reached over and gripped the big blue dildo by the shaft, near the spongy-feeling balls that housed the vibrating thing's batteries. The cock wriggled in his hand, and he remembered that they'd realized this dildo was the exact size of his actual cock. And then remembered that he'd had this dildo in his mouth only hours ago, (not just his mouth, deep in his throat!), playacting the role of a cocksucking whore, and his dick swelled again against the soft fabric of his panties.

He handed it over to Diane, who lazily pulled back the sheets, and reached into the front of her panties with her other hand, touching herself as she moved her hips. She pulled her hand out and hooked her thumb into the waistband of her panties as she lightly lifted her butt off of the bed, pulling them down.

"You're really gonna do that in front of me?" Kim asked.

"Look, if it bothers you so much, why don't you get into the bathroom and wash your face so you're ready for today's epic makeup tutorial while I take care of business out here."

"Okay," said Kim as he got up, trying, not very successfully, to his erection with his hands as he skipped away. Walking across the room, he heard the buzz of the dildo, and Diane's moans. Along with the rubbing of his panties on his hard cock as he walked, it was driving him insane.

Once inside the bathroom, Kim looked at himself in the mirror. The illusion of his femininity was somewhat lessened by the huge, hard cock sticking out above the top of his red lacey panties at a rakish angle.

He couldn't help himself. He pulled his cock out of his panties and leaned against the counter with his left hand, while gripping his dick with his right. He soft panties still covered his perfectly smooth scrotum. He looked up at himself in the mirror, - and then he straightened his legs and bent over, sticking out his ass in an exaggeratedly feminine position. The way the panties looked on his hips, the roundness of his butt. He pursed his lips, still smeared with last night's lipstick. Holding his dick in his hand, he slowly started stroking it and swiveling his hips -

Outside, on the bed, the blue, vibrating dildo was slowly working its way into Diane's pussy. She smiled, and put her other hand on her breast, feeling her fingers, one by one gently pass over her nipple which reached out, begging for touch.

She knew Kim was probably jerking off wildly in there - that poor horny bastard. A virgin! This whole time! She knew he'd been unlucky in love - always pining after that horrible Laura Whetherbee, hot though she may be. But she'd always assumed that Kim must have hooked up with her at some point! I mean, Christ, Laura was a well-known whore. She'd hooked up with half of Kim's friends, for God's sake!

And how could Kim never have gotten anywhere with a girl? If not with Laura, then one of the other girls in his class. Weren't more teens than ever having sex earlier? That's what the angry people on TV were always saying! And it had certainly been true in her own experience.

"I bet he's had lots of chances," Diane thought to herself. "The guy is gorgeous - I mean, he's such a pretty guy he makes a pretty girl with only a little makeup. But poor Kim is so inhibited he probably made all kinds of excuses not to do it." Self-sabotage, that's what it was. He'd just blown a chance to lose it just now! Sure, to his sister, but it's not like she wasn't a gorgeous piece of ass - one every producer and actor who'd seen her had taken a pass at. And a few of them had even succeeded!

She wondered what he was doing right now, in that next room - almost certainly jerking off. Using the panties? Looking in the mirror. Thinking about being a girl. Getting into character. The thought of transforming her brother into a sexy college coed was making her so hot, she could feel it coming, as she felt the vibrations deep inside her - her orgasm rolled over her, and she bucked her hips and moaned loudly, over and over again.

Inside the bathroom, Kim felt so close. He took his other hand and ran it down his thigh, so smooth, then back up his inner thigh. While he lovingly stroked his shaft with one hand, the other's fingertips explored his testicles, and then up the little patch of skin behind them. Perfectly hairless after his treatment last night, a place he'd never touched himself before - but now, for some reason, it seemed perfectly natural.

He pressed down hard, and felt his cock harden further. He could feel the delicate little ridges on the underside of his cock -

Just then, the door opened. It was Diane, still wearing only her loose tank top, and no panties at all. She was totally hairless down there - it was good to know she wasn't being a hypocrite when she put him through such a thorough hair-removal process!

Kim let go of his dick, embarrassed, turning away.

"Don't stop cause of me," Diane said. "Seriously." She smiled and looked at that beautiful, hard cock. She'd known perfectly well what she was going to find when she opened that door. And what had he been doing with his other hand?

Kim, hesitantly, put his hand back on his dick and started stroking it. Knowing his sister was standing there, watching, touching herself while she leaned against the bathroom wall, he couldn't take much more - Kim closed his eyes and leaned his head back.

He heard something, then felt Diane's soft hand on his balls. He opened his eyes to realize that Diane had dropped to her knees in front of him.

"You tasted so good last night," Diane said, softly, quietly.

Kim spread his legs apart a little, and Diane reached behind them and started massaging the taint while Kim kept stroking his dick. Diane leaned forward and licked his scrotum, then opened her mouth wide and took his right ball into her mouth, sucking gently while the shaft of Kim's dick rubbed against her nose and face, with Kim gently stroking it, already on the edge of coming.

Diane took her mouth off of his balls, and stuck her finger in her mouth - deep, deep into her throat. Then she took that spit covered finger and reached between Kim's legs as she backed up, opened her mouth again and licked the tip of Kim's dick, tasting the sweet drops of precum that had collected there.

Kim took his hand away from his dick, and Diane took it into her mouth. At the same time, her spit-covered fingertip found Kim's perfectly hairless asshole and pressed into it. Kim groaned and threw his head back, arching his back and running his hands over his own chest, feeling his false breasts like he's seen women in pornos do.

Diane, looking up with Kim's cock deep in her mouth. marveled again at Kim's body - so thin and sleek, like a beautiful girl's in every way. Even the way he arched his back and the curve of his neck. Graceful. Like a girl. And really taking to being ever so slightly diddled by her finger.

Diane would've smiled if her mouth wasn't so full of dick. She drew inch after inch of his huge cock into her throat, working herself open bit bit bit. At the same time, she just applied more pressure with her finger, worming her way into his ass, slowly fucking in and out with her single finger, gently - he was a first-timer after all, and a virgin. She could feel Kim adjusting his hips, opening himself up to her.

Kim's hips bucked, and he grabbed Diane's head with both hands, driving his huge cock into her throat. Diane's eyes watered - she couldn't breathe at all as her brother filled her throat with his huge python - but he wasn't really fucking her anymore, he was just holding it there as she fucked him with her finger. He was in ecstasy - but she couldn't breathe! There was no time to lose.

Diane had done this to a man before, and knew how to find his spot. She worked her finger in, and she felt his cock stiffen even further. Within moments, Kim gasped as he shot his load deep into her throat.

Finally, Diane pulled back and let Kim's dick, now softening but still huge, fall out of her mouth, with little strings of semen and spittle stretching between her pouty lips and his dick.

"Why did you do that?" Kim asked.

"Because I love sucking your cock. It's perfect, and I love the taste of your cum," Diane answered as she rested her head against his hip and gently ran her hand over his balls. "I wanted more."