12 comments/  101873 views/  75 favorites

Kim Gets Off to College

By: sexykitsu



Kimberly Perkins had never especially liked his name. For one thing, as he liked to point to his mother, and his big sister liked to point to him, Kimberly is a girl's name. But it had been a tradition to name boys Kimberly in the family for generations, after some long-ago ancestor. It didn't help that Kim wasn't exactly the most macho guy in school. He even though he was 18, he still hadn't exactly developed a big, manly physique. He had finally gained height, up to about five foot nine, but he was still very thin and even had a sort of girlish body, with hips wider than his little waist and his perfectly flat belly. He'd recently grown his hair long, too, to try to make the androgynous look work for him, like a rock star kind of thing, but he wasn't at all sure it was working. None of the girls at school ever seemed to be able to take him seriously, treating him like he had stayed a little boy forever while the rest of the class had grown into adults -- big, hulking men and curvy, sexy women. Women who would never give Kim the time of day.

Kim hoped it would be different in college. He would be making a fresh start, a fresh go of it. He hadn't been sure where he wanted to go, but his mind was made up for him when he was unexpectedly awarded a full scholarship to Sarah Van Hufferling College. Kim had barely heard of it before he got the letter, but he'd sent out so many scholarship applications that he'd lost track. When he googled it now, he saw that SVH was highly rated across the board, especially in the areas that Kim was most interested in studying. Deciding to trust to fate, Kim accepted the scholarship, and now his freshman year was due to start in mere days.

Kim's sister Diane was five years older, and had just graduated from college a year earlier. She was an actress now, and had already scored a couple of television guest spots playing "hot chick" type roles, although none of them had aired yet and so Kim hadn't seen them. He wasn't surprised that Diane was booking roles, though...she was gorgeous! She was tall (the same height as Kim, actually) and fit, with a long lean shape from both her blessed genetics and a strict yoga regimen. Her breasts were on the smaller side, but were perfectly placed and round -- Kim often found himself having to fight the urge to stare at his own sister! He'd actually thought about her when he masturbated a few times, although he was always ashamed afterwards. But the way she would run around the house in just her underwear during her visits home from college would drive him crazy, until he had no choice but to close the door to his room and help himself.

It's funny, but people often told Kim and Diane that they looked alike, and even Kim had to admit it was true. The high cheekbones, button nose and delicate chin were the same -- the only difference is that it looked good on a woman! Kim just felt decidedly unmacho all the time, even though Diane repeatedly assured him that he looked fantastic and that girls were going to start realizing that any day now. He was beautiful like a doll, she'd say -- and was going to make prime cougar bait as soon as he could start going to bars. That moment couldn't come soon enough for Kim. 18 and still a virgin. Humiliating! So humiliating, in fact, that he usually lied about it if someone asked. A virgin? Me? Don't be ridiculous!

Diane, who had no set work hours because of her actress's life, had decided to help Kim move to college and had driven her car, a 2009 Civic, all the way back home to get him. Kim appreciated it -- otherwise his mother would've insisted on moving him out to college, and he didn't want the other kids, especially the girls, to have their first impression of him be that he's a mama's boy. He'd have a hard enough time seeming cool as it was!

Once they were on the road, it was like old times. Kim drove while Diane sat shotgun, with her perfect tan legs on full display as she curled up in her seat with no seatbelt. Diane was full of stories about Hollywood, and the famous people she had met, and whom she'd seen get drunk, and who was secretly gay. Kim mostly listened and laughed along. Diane was a great storyteller, and had always had a sexy confidence that Kim could never match. She was even more beautiful than she had been when she'd moved out to L.A. a year ago. She just kept getting better with age.

It made Kim a bit uncomfortable, however, when Diane started talking about her sex life.

"So, don't tell anyone this, but I dated a movie star for a little while. A big movie star..."

"Which one?"

"Well, I can't tell you, but I will tell you that you've seen him in the movies. More than one. Actually, he's in what I think is your favorite movie."

"What? Pulp Fiction? Samuel L. Jackson?"

"No! Since when is Pulp Fiction your favorite movie? That movie's like a million years old..."

"So who was it?"

"I promised him I wouldn't tell, so I won't. But he's rich, and he took me on some amazing dates. He took me for a helicopter ride out to a yacht and then we fucked out on the deck under the stars..."

"Whoa, sis," said Kim, blushing. "T.M.I."

"What? You didn't think I'm a virgin, did you?"

"No, I guess not -- its just, you know, you're my sister, I don't want to think about you -- you know..."

"Fucking? Making love? Coitus?"

"Coitus? Was it Jeff Bridges?"

"No! Why do you keep thinking of these super old guys? God! Anyway, it's over."

"What happened?"

"He wanted to me to give him a blowjob for his birthday."

"Oh, and you don't...do that" Kim let his voice trail off, not even wanting to say it.

"Don't give blowjobs? Of course I do! I'm not frigid or something. I actually kind of love sucking cock. It's really satisfying to get a guy to cum in my mouth, like a treat as a reward for a job well done. The problem was he wanted me to do it in front of everybody at his birthday party. He likes to show off, I guess."

"Oh my god," said Kim, shocked. "You didn't do it, did you?"

"No, I didn't do it. There were going to be industry people at that party and I didn't want them to think of me just some cocksucking whore, you know? But the truth is, I really wanted to. The idea of kissing his big dick, licking it up and down, taking it all, while a whole crowd watches me and gets turned on, mmm," Diane started feeling her own breasts while she spoke. 

"But you'd never do anything like that, would you?" asked Kim.

"I didn't think I'd want to do something like that, but now I find myself thinking about it all the time. And who knows, maybe in the right circumstances, with the right people, the right audience....Oh, god, I'm turned on." Diane reached down under her skirt and started feeling her crotch. 

It was all Kim could do to keep his eyes on the road. "Diane, what are you doing? You can't do that here!"

"It's my, mmmm, car..." Diane wasn't stopping. "Don't tell me you're not enjoying this." Diane looked at Kim's pants, where she could see the telltale bulge.

Kim knew it, too. As much as he hated to admit it, he was incredibly horny thanks to his sister's story and her actions now. He could smell her sex in the air and tried to keep his mind of his throbbing erection, which strained against his kakhis. He wanted to close his eyes and be somewhere else. 

Then he felt something. A hand. On his dick. Diane was feeling him up.

"Diane, no, what are you doing?"

"Oh my god, Kim, your cock is so big..." She stroked it up and down through his pants. "I had no idea..." Diane turned herself so her ass was to the door and her head was practically in Kim's lap.

"Diane, stop it," Kim gasped, though he felt himself gyrating his hips with the motion of her hand. Diane unzipped his pants and reached into his shorts with her left hand. "It's incest!"

"We're not even doing anything," said Diane. "I'm not going to get pregnant."

"Diane, no!"

"Please, Kim. Please let me suck your sweet big cock. I want to taste your cum." With that, Diane licked the tip of Kim's penis, causing Kim to jerk his entire body, sending the car swerving across two lanes.

"Shit, Diane, you're going to get us killed!"

"Fine, I'll stop. But I'm too horny to stop on myself."

"You can't do- do that! Right here in the front seat? I'm trying to drive!"

"Ugh, fine," said Diane, rolling her eyes. "I'll do it in the back." With that, Diane started crawling in the back seat, head first, sending her ass brushing up again Kim's shoulder and face.

Once she flopped ungracefully onto the back seat, Diane laid down and started going to work on herself. She pulled her dress up above her waist and took her panties off entirely, and began rubbing her clitoris. She dipped two fingers into her pussy, sopping wet from her excitement from almost seducing her little brother, and used her moist fingers the rub her clit from side to side as she moaned loudly, more loudly than she normally would. She smiled an evil little smile, knowing this was tormenting Kim.

In the driver's seat, Kim grimaced and tried to ignore both his raging hard-on and his hot sister pleasuring herself loudly in the back seat. He turned on the radio and changed the channel until he found some hard rock, and cranked it up to eleven. He tried not to look back, but the smell of Diane's cum gradually filled the car until it became overwhelming to him.

After what seemed like hours, Diane finally crawled back into the front seat, moving lethargically and smiling, with her eyelids drooping shut, like a cat who's just eaten a canary.

"Thanks, little brother," said Diane.

"For what?"

"For being my audience. I think I do like to be watched. I'm going to take a nap. Wake me up when it's my turn to drive." And with that, Diane went to sleep. 

*****

Diane was naked on a big mahogany tables, the centerpiece of a cocktail party. Fashionable people, the rich and powerful, drank cocktails and watched her writhe in the center of the table, lit by flickering candlelight. She moaned with anticipation as the crowd grew nearer, men and women both admiring her flawless skin and her supple form.

A blonde woman, older, probably in her forties, approached Diane's table. "This is your new discovery?" she asked. "Your diamond in the rough?"

A silver-haired man standing beside her laughed gently and placed his hand on Diane's neck, touching her behind her ear, tracing her jawline to her chin. She turned and opened her mouth, showing just a bit of her tongue. He gave her his index finger and she sucked it deep into her mouth, lovingly nibbling on it. How she wished that finger were something else.

"Yes," he said. "As you can see, she's quite agreeable, and, let's say... eager to perform."

"I see that," said the older woman. "But how does she taste?" With that, the older woman, fully dressed in a classy dress and small jacket, put her hands on Diane's thighs and spread her legs apart. Diane moaned as the woman lowered her face to taste Diane's wetness --

"What is going on back there?" asked Kim. Diane woke with a fright. It had only been a dream.

Diane sat up slowly, winking the sleep out of her eyes. Her body was still hot and horny and she tried to tell herself to turn it off.

"You were, like moaning, and moving around like a dog dreaming about chasing a rabbit," said Kim.

"That is not what I was dreaming about," said Diane, smiling devilishly. "I dreamed I was naked at a party, and everyone was watching me and waiting their turn."

"Are you serious?" asked Kim. "You were dreaming about sex after -- what you did before?"

"Sure, why not?" asked Diane. "The more I get the more I want. This dream was different, though -- I think I might be a little bit of a lesbo."

"You're not a lesbian!" shouted Kim. "You love sucking- you know! You just said so -- you tried to do that to me!"

Diane laughed. "I said a little bit of a lesbo, I still love cock, obviously. You take everything so seriously, Kim. You need to lighten up. Hey, where are we, anyway?"

"We just got off the freeway. Thanks for navigating, by the way. Bang up job keeping me company. Instead of listening to music with me and imparting college advice and stuff, you've been over there touching yourself and having sexy dreams."

"Don't get your panties in a bunch," said Diane. "I'm awake now, so let's check out this college of yours."

After finding parking, Diane and Kim decided to take a walk around campus to find some food before heading over to his dorm.

In this small college town, several hours outside the city, it looked like most of the population was students! And an impressive student body it was, too. Everywhere Kim looked he saw beautiful girls, often wearing short skirts and summer dresses in the September heat. Especially after what Diane had done in the car, Kim had sex on the mind and now he felt himself mentally undressing every girl he saw, untying strings and pulling up skirts and pulling panties down -

"Hey," said Diane, interrupting Kim's reverie, "have you noticed anything strange about all these girls?"

"What?" said Kim, pulled out of his sexy daydreams, a bit ashamed. He glanced down to see how obvious his erection was -- somewhat obvious, it turned out. Kim pulled his sweatshirt off and wrapped it around his waist. "I wasn't looking at the girls -"

"Of course you were, idiot. So was I! There are tons of totally gorgeous babes around here, you're gonna have a great time! But what I'm wondering is, where are the guys?"

Now Kim looked around -- she was right! It wasn't that he had just been looking past all the other guys in the crowd, like he normally would, it was that there were virtually no men here at all, only a few older men, here and there, probably fathers of the students.

"Excuse me!" said Diane to a passing young woman, a five foot three Asian with a bob hairdo and a short skirt. Kim tried to look like he wasn't here with Diane.

"Yes?" asked the Asian girl.

"What's up with this campus? Where are all the hot guys?" asked Diane.

"Oh, there are no guys. This is a girls' college!" laughed the girl as she skipped away. Kim's eyes were drawn the backs of her thighs where they showed skin between her knee-high socks and her short skirt, but what she'd just said jumped out at him. 

"Wait, what?" asked Kim. "Sarah Van Hufferling College? It's only for girls?"

"Well, duh," said the Asian girl. "It's, like, only the most prestigious girls college in this whole region of the country! It's a great place and I love it - the only problem is the rules against having boys in the dorms." With a wink, she skipped away.

Kim turned to Diane to see her trying to suppress her laughter, but failing. Kim's face turned a bright red with humiliation. 

"Well, that's it, we're turning around and going home," he said. 

"What?" exclaimed Diane. "I can't let you walk away from a full scholarship. And didn't you hear what she said? It's a prestigious school!"

"Stop teasing me," said Kim. "It's a girls' school. I can't go here -"

"So what's your plan then? Are you going to not go to college? Mom and Dad will love that!"

"No, I'll just - maybe I'll just sit out the first semester, and maybe I can get into another school -"

"Another school that will give you a full scholarship? This really is a once in a lifetime opportunity, Kim. I can't let you just walk away from your future!" Diane looked him up and down his body and smiled that little smile she gets when she's having a tricky idea.

"What are you thinking?" Kim asked, even though he already had a sneaking suspicion he knew just what it was.

Even thirty minutes later, at the drug store, he couldn't believe he was even considering it, even after they'd driven away from the school without moving his stuff into his dorm. No, something like this required preparation, Diane had insisted. Now she was running around the drug store piling her cart high with products.

"You'll need a haircut, obviously, but luckily for you I give fabulous haircuts! I'd still be making great money at the salon even if my acting career hadn't hit it big."

"Would you stop talking about this?" asked Kim, glancing around the mostly barren CVS.

"What? You don't want anyone to know you're going drag?"

"Shut up, Diane! If we do this-"

"Oh, we're doing this -"

"If we do this, then we're going to do it well. We have to be sneaky. I don't want to get busted cause someone who saw us here tonight ends up in one of my classes -"

Diane smiled. "All right. We'll do it right. Really right. I'm going to make you unrecognizable. But you're going to have to trust me. You'll have to walk like a girl, and think like a girl. I'll make you a pretty girl and put you in a good position to be popular-"

Kim found himself imagining himself in a dress, attending classes with the other girls, his hairless legs crossed as he sits in a desk with in a short skirt - then his cheeks turned red and he shook his head, trying to shake off the feelings that were coming to him.

Diane laughed. "You're going to have to get over your embarrassment if you ever want to pull this off, Kim. Now come one, I only have a couple more things to grab, then it's on the motel! Don't worry about the cost, this is all on me. Thank you, Hollywood!"

When they got to the hotel, Kim checked out the room while she was making the arrangements down at the front desk. It was one room, with one bed. The bathroom was big, though, with a full length mirror and a luxurious, oversized tub with water jets and the whole works. That was good, Kim thought. He wasn't looking forward to shaving his legs, but at least he'd have room to do a proper job of it.

Diane walked him through the various products he was to use in his de-hairing of himself. Luckily, he wasn't a particularly hairy guy to begin with. Much of his body was naturally hairless, and he barely had to shave his face once a week! Although he realized he would need to do it more often now. If he was going to, well, commit fraud by attending an all-girls school and living in an all-girls dorm, he was going to do his utmost to not get caught. And in the end, after a mere four years of living as a woman, he would get a degree with his own name on it, "Kimberly Perkins," and no one would ever have to be the wiser. He could move home, or to any other city, and go back to living as a man.

Diane kissed him on the cheek. "Now I'm going to run to the mall real quick before they close to get a couple more things."

"What things?"

"Just a bit of this and bit of that. Clothes for you to wear tomorrow, for one thing -"

"I have clothes!"

"Boy clothes. You can't wear any of that in this town! I'll save them for you to wear when you come home to visit. No, tomorrow, we're going shopping, and you're going as Kim, the girl. It'll be a good practice run before we go to your dorm."

Kim looked despondently on the wax he was about to have to use on himself. "Don't worry, Kim" Diane continued. "You can totally pull this off. You're beautiful, and you're smart, and you've always had a flair for the dramatic. Think about it this way. You're about to be living in a dorm with hundreds of young girls who are probably all going to be running around in their underwear all the time. Won't that be fun?"

"It's not like I'll be able to do anything about it," said Kim glumly.

"Maybe you just need to think a little more creatively," said Diane with a wink. "Now, by the time I get back, I want your whole body hairless and soft as a baby's bottom. I'm talking everything. So you better get moving." And with that Diane, disappeared out the door.

Kim set to work, following Diane's written instructions to the letter. He had to laugh when step three was "Open up that bottle of white wine I left in the fridge and have a tall glass." Soon, Kim, who was not used to drinking, was pleasantly buzzed as he slathered wax onto his legs. It was a good thing he was drunk, too, when it came to following some of the steps Diane's instructions put forth for him, like the removal of all hair from his scrotum and his anus. He didn't understand how he needed a perfectly hairless asshole to dress like a girl, but Diane's note was quite vehement on this point, so he suffered through it. Somehow, over the course of the night, with quite a bit of discomfort, he managed to achieve his mission, removing all the hair from his entire body. 


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."




Kim Gets Off to College Ch. 02



"It's not gross?" asked Kim.

"If it's so gross why would so many girls do it? Maybe I thought it tasted a little nasty the first couple times I blew a guy - Tommy Peterson - " she remembered. "But I also knew I wanted him to enjoy it, and I figured a guy's gonna enjoy a blowjob the most when he thinks it's totally getting you off and you desperately want to eat his jizz. So I guess I acted like I loved it. And you know when I act I go all out." Diane smiled and licked her lips. There was still sticky white semen dripping down her chin.

Kim slid down the counter until he was sitting next to his sister. He was going to put his arm around her - but then she reached out and put her arm around his shoulders, instead. He leaned against her, looking admiringly at his sexy sister.

"Yeah, that's it exactly, I acted like I loved it, just like I was playing a role - auditioning for the role of Cumslut Number One," Diane giggled. "A lady in the streets but a freak in the sheets, right? Total commitment is the key. So I went to town on Tommy's dick like the antidote was in it, and smiled and complimented him afterwards and told him I'd never tasted anything so delicious. And I think I was lying, at first. But now, maybe as a result of the emotions that come along with giving oral - like feeling desired, and in control, and powerful when I get a guy to blow his load - well now I really do love the taste, and I really do crave it. Authenticity comes from total commitment to your character."

"So do you really enjoy the taste? Or not?" Kim wondered.

"I think it's something of acquired taste, like coffee," she said.

"I love coffee," Kim said. 

Diane ran her finger along her own chin, scooping up some of the jizz that had still been on her face, then held it out for Kim.

"Commit to the role," she said.

Kim opened his mouth and took Diane's finger into is, sucking the semen off. He licked his lips, and swallowed. It was salty, and gross, and he felt a little sick, momentarily. But he wanted to stay in character. He smiled and licked his lips. He imagined he'd just had a sip of an ultra-delicious cup of coffee.

"Mmmm," he said. "I love it."

"Good girl," said Diane. "Now get cleaned up. We have a lot to do today."

*****

An hour later, after Diane had claimed the bathroom for a long shower, Kim himself showered, himself, removing yesterday's makeup and washing the heavy product out of his newly styled hair. 

He came out of the shower to realize he hadn't grabbed any clothes out of his bag before he'd gotten into the shower. The panties and bra he'd been wearing last night were sitting on the top of the toilet. 

He shrugged, and after looking at himself in the mirror - a bit confusing, that, with a girl's haircut contrasting sharply with the flaccid, but still impressive, dick, dangling from his thin, athletic, and androgynous body. He dried himself off with the hotel towel, using a second small towel on his hair, which still looked pretty good even without product and somehow made his face look feminine even without makeup, with the way the medium length hair framed his face - Diane really did know how to give a great women's haircut. 

It was lucky he'd started with his hair long! But now his long rock locks were gone, replaced by a chunky modern do similar to Diane's, but a bit longer and younger, better reflecting Kim's college girl status.

Kim wrapped his towel around his waist, as he always had, and walked out into the room. 

"What the fuck?" Diane was dressed in tight blue jeans that really showed off her ass, with red pumps and a sleeveless pink eyelet top. But she looked mad.

"What? What'd I do?"

"What are you doing with your towel wrapped around your waist like that? You're supposed to be a girl."

"What? But it's just the two of us - "

"Re-tie it, Kim." Diane crossed her arms and scowled at him. "If you're going to pull this off, you seriously need to start doing a good job of it. You need to get into character, starting right now, or we'll never get the kinks worked out of your act. It's not like there' s lot of time to waste. Your classes start Monday!"

Kim sighed, untied the towel from his waste, gripping the corner in his right hand as the rest of the towel fell away from his body.

Diane licked her lips, seeing her brother's gorgeous cock again. How did such a skinny guy, with the body of a model (one matching her own drool-provoking actress body perfectly except for the breasts), have such a huge dick? Completely hairless, it dangled majestically over and past the smooth pillow of his scrotum.

Kim brought the towel up to his armpits and laughed. "I've never done it like this before-" but he soon figured it out, and checked himself out in the mirror, while Diane looked on approvingly. 

He wore the towel just above where his breasts would've been, and it just barely managed to cover his ass. He looked in the mirror. His legs were so thin and smooth, and when he angled his hips back a little and arched his back, the illusion was perfect. The towel fit like a little mini-dress. Turned on by his own appearance, his cock started to grow, pushing forward the bottom of his towel.

Diane laughed. "But seriously, you've gotta learn to control that thing. You're in charge of that, though. Right now I've got to teach you some serious shit. Makeup!"

"How hard can it be?" Kim said. "Girls do it."

Diane pinched him. "Ouch! I was just joking!" he exclaimed.

"Makeup is an art form, and every other girl on the planet has a head start on you. We've all been learning how to do this stuff for years - or at least most of us. The hot ones. And we've read tons of magazine articles- by the way, I'm getting you some Cosmos and stuff, and you're gonna study them like you're studying for the damn bar exam- it's equally important for your future.

"But for today," she continued, "I'm going to teach you the basics. And the intermediates. And we're pressed for time, so you're going to learn by doing. You and I have almost the same face, so I'm going to explain what I'm doing as I do it to my face and you're going to try to do the same thing to yourself, okay?"

"All right," said Kim. "I'm actually sort of really intimidated by this. I mean, it's been fun to play make believe with you, but I find it sort of hard to believe anyone will ever actually buy me as a girl once they see me up close."

"They will, Kim," said Diane. "It'll be hard, but I'm sure you can do it. As long as you genuinely give it your best shot. You have to be totally committed to the role or it won't work. If you commit, they'll buy anything."

"All right," he said. "Commit to the role. Now where do we start on this makeup?"

Diane smiled.

*****

When they were done, Kim was amazed to see himself looking just as good as he had the night before - in fact, once again, he looked almost identical to Diane! 

It had been hours, and it was an incredible mass of information, but Kim had been a great student, literally taking notes in the pink Hello Kitty spiral notebook Diane had purchased for him the night before, ever so thoughtfully. "Props are key for an actress," she'd said. 

His head was swimming, but he was a great student at school, having qualified for a full academic college scholarship, after all (even if it was to an all-girls' school), and he applied his well-practiced learning techniques to his sister's interactive lecture.

Now he was made up as a modern young lady with a rocker attitude, with somewhat glamorous dark eye makeup that might be a little much for your average college freshman - but not for the fashionista that "Kim the girl" was going to be in accord with Diane's decree. 

He was worried it was going too far, but now, seeing the end product, he realized for the hundredth time that Diane really knew what she was doing in the hair and makeup department. The dark makeup, creating the illusion of bigger eyes, made his entire face, which was already soft and fine-featured, look feminine - to the point where he doubted anyone would ever guess he was a boy just from his face.

Once his makeup was done, he dropped his towel and put on the pink ruffled panties that Diane had laid out for him, carefully tucking his dick between his legs. Then he put on his pink matching bra and his false breasts, arranging them carefully to pull his pecs together and create a little cleavage. Diane watched the whole time, but Kim was no longer so embarrassed. He was rapidly getting used to being seen nearly naked by his sister. It felt freeing, in a way, to be comfortable with somebody else. 

Diane couldn't help but admire Kim while he looked himself in the mirror, arranging his bra. He had no idea what a gorgeous body he had - just about any girl would kill for legs that long and elegant or an ass so round and pert! Really, the whole package. 

Diane gave him a short yellow summer dress out of her own luggage. It was sleeveless and looked very small and insubstantial in her hands, to Kim.

"A dress? Couldn't I wear, like, jeans and a sweater?" Kim asked. "You're wearing pants!"

"It's a beautiful August day, you're wearing a summer dress," said Diane, who was dressed in form-fitting dark jeans and a pink top. "Besides, we're going shopping today and we want something you'll be able to get in and out of quickly in the changing rooms. Now stop being a pussy and start acting like you have one, and put this dress on, girl!"

Kim sighed and started to pull the dress over his head -

"What are you doing?" Diane asked.

"Putting this dress on - right?" he replied.

"You step into a dress, you big dummy." Diane laughed. "Your shoulders are the widest part of your body."

Kim blushed, then tried again, stepping into the dress and pulling it up over his hips until he was able to pull the straps over his shoulders. 

It left his pink brastraps showing under the yellow spaghetti straps of his dress. "Isn't this a little slutty? To show my brastrap?" Kim asked.

"Sure," said Diane. "But only a little - the right amount of slutty. Now for accessories!" 

Diane adorned Kim with a few chunky bracelets, a couple of tasteful rings, and a thick lace choker. 

"I've always thought a choker is really sexy on a woman," Kim admitted.

"That's because it reminds you of a collar, you sicko," smiled Diane. "That's why it's so sexy. But you're wearing it for a different reason. You're a guy, so you've got an Adam's apple. Luckily, yours is almost invisible, but it's best not to take chances. I'll have to show you some good ways to tie scarves, too, those'll be good for you."

Kim checked out the choker, on himself. Diane was right, he realized. He'd seen a few pornos on the internet with a girl wearing a collar and chain - a slave sexually servicing her master, and it had really turned him on. Now Diane was telling him that he was going to be wearing a collar, of a sort, from now on, almost like he was a slave-girl. 

"Now the shoes. First put these on."

Diane handed Kim a pair of long white socks, which he sat on the bed and pulled on over his smooth, hairless calves. They reached to his knees and he became more aware than ever of his bare thighs - he was flashing a lot of skin between his schoolgirl socks and his short dress.

While he did that, Diane produced from her bag of goodies a pair of black shoes with heels and a bow on each one. She put them on the ground in front of Kim, and he set one foot onto one - the heel was much higher than the toe, and it was hard to hold his balance. "I've never worn high heels before last night. If we're seriously going to the mall, I don't know if I'm gonna be able to get around too well."

"These are Mary Janes," said Diane, as she put her hands on her brother's delicate calf, helping him ease into the shoe and find his balance. He put his hand on her shoulder and stepped into the other one, too. "And these heels are pretty low. They're a little easier to walk in then some of the other heels you'll have to get used to, but they'll get us started. Do they fit?"

"Yeah, perfectly. How did you know?"

"I'm a genius, Kim, never doubt it. The other good thing about these Mary Janes is that they're close-toed. You can't wear sandals or anything open toed until we get you a pedicure and paint those toes."

Diane put her hands on Kim's hips, and used him to stand up, then she walked across the hotel room in her own heels and turned back to look at him, with her hand resting on her jutted-out hip. "Now walk to me."

Kim took one uncertain step, then another, then stumbled before catching his balance with a hand on the bed. 

"You have to shift your weight - " said Diane.

"I'm getting it. Give me a second!" Kim said, before pushing off from the bed and taking a couple of successful steps. "Why do I have to wear heels anyway? I'm already sort of tall for a girl. Couldn't I just wear, like, girls' sneakers?"

"Heels aren't about height," Diane said. "They make our legs look better, and elongate the body, and make you concentrate on your posture. That's why you especially are going to have wear them pretty much all the time, so you don't revert your horrible boyish slouch and blow the scam."

"It's not really a scam," said Kim. "I'm just trying to get an education, like any of the other girls." Kim was now starting to get the hang of it, successfully walking without losing his balance at all. "Hey, I'm not falling anymore!"

"You still look stiff - walk like you're walking on a line, one foot right in front of the other."

"Like this?"

"Don't be afraid to use your hips a little. Watch me." Diane took a walk across the room, really tilting her hips back and forth with each step - almost a strut. "Do that."

"I don't know if I can do that. Aren't there anatomical differences?"

"You've got hips, right? And a spine? You can do it, you're just not used to it. Give it some attitude, girl! Think Beyonce!" Diane stalked back across the room to Kim and stepped behind him. "Like this."

Diane put her hands on Kim's hips - he could feel each finger through the lightweight material of the dress. She stepped closed behind him, so close that her right foot came between his two feet, and her groin was pressed up against his ass.

"You just take one step," she said steering his hips with her hands as he slowly stepped forward. She stepped along with him, gyrating his hips left and right - and Kim was surprised to find it working. He found the natural motion she wanted, and she let go, as he strutted to the other side of the room. He'd found his balance. "How's it look?"

Pretty good, just relax your shoulders and your arms, yeah that's it."

Kim strutted around the room, watching himself in the mirror. He really did have it - a sultry walk. 

"Maybe it's a little too much?" Kim asked. "I feel like I'm exaggerating it, 'vamping it up.'"

"Nah, it's perfect. God, look at you. Look how thin your waist is, and your arms are. What do you eat?"

"I don't know - food, I guess. I've always been skinny."

"Well keep it that way, cause it's really helping your cause. You've got a body most women would kill for."

He looked at himself in the mirror. He could see what Diane was talking about. He struck a couple poses. He raised one foot, and spun on the other. The bottom of his billowy yellow dress blew up with his spin, and he could feel the cool air on his thighs and his back and tummy above his pink panties. He even landed the spin without wiping out! His first twirt, in heels, pulled off successfully. 

"God, wearing just this dress, I feel like I'm practically naked," Kim said. "And this isn't even that especially revealing! But it's like, just this one batch of fabric, and it's almost see-through in places. But seriously, how do girls walk around feeling the air between their legs, and that there's really nothing covering them but some thin panties-"

"And sometimes not even that," winked Diane. 

"Doesn't that make you horny all the time?"

"Sure," said Diane. "A lot of the time. You look incredible, by the way. And I'm not just saying that because I styled you myself."

Kim continued posing at himself in the mirror. He put on fist on a hip, and cocked his head to the side. He turned, looking at himself from every possible angle. He couldn't believe how pretty he was! A clean, fetching young girl, sexy and fresh. The somewhat billowy skirt of the breezy yellow dress concealed the sight of his big cock, even now, while he was ridiculously turned on.

"So are you ready to go out into the world?" Diane asked.

"What?" Kim said. "Leave the room? No! I need more lessons! They'll see through me right away!"

"No they won't," said Diane. "And the best way to learn is by doing."

"What if someone can tell, and they laugh at me?"

"You can fool anybody, Kim, or you will be able to, anyway, when the time comes. I'll prove it to you. All I need from you is to commit to the role."

Diane grabbed Kim's hands and looked deep into his beautiful green eyes. It was like looking in a mirror. "Don't you trust me?"

"Yes, I trust you."

"Then we're going to the mall!" Diane turned and pulled his hand over her shoulder as she walked him to the door. 

"What about my wallet and phone? And the hotel key?"

"Oh," said Diane. "They're in your purse. Here," and she handed over a green, sort of cylindrical mod-ish purse. Kim looked inside, and sure enough, there was his stuff, plus lipstick, a compact, and other girls stuff. Kim pulled a pair of oversized Paris Hilton-type sunglasses out of the purse and put them on, then threw the purse over one shoulder. It felt natural, actually, resting against his breast, just under his arm. 

"I guess I'm ready to go then."

They opened the door and walked out into the sunlight.

Kim practiced his new hip-swinging walk on the way across the parking lot to Diane's Honda. It felt a little different now that he had a purse under his arm, but it felt great to really open up the throttle and hit his stride after practicing in the cramped quarters of the hotel room. He felt his yellow dress brushing against his thighs and it turned him on.

"My hips are going to be sore tomorrow," he said. "I'm not used to using these muscles like this."

"You're doing a great job, though." said Diane. "Hey, take a sly look over there." 

Kim peeked sideways through his sunglasses and saw two men checking them out as they strutted across the parking lot. Both men were around thirty, and one was even doing the classic "Risky Business" pull-down-the-sunglasses-to-look cool-guy thing at them. What a cheeseball! They noticed the girls looking at them.

"Hey girls! Where you going?" called one of the men, a tall blond guy who looked sort of like the movie star Tom Jane, almost cartoonishly masculine.

"Out," said Diane.

"Are you coming back here later? Can we buy you a drink?"

Kim blushed. Not only did these guys believe she was a girl - they were hitting on her!

"I think we might be a little out of your league, guys" said Diane.

"Nobody's out of our league," said the cocky blond man. "How about you, sweet thing?" he directed his question at Kim. "You'd like to have a drink with me, wouldn't you? I'd like to look at you some more - you're gorgeous."

Kim smiled and turned an even deeper shade of red, but shook his head.

"What's the matter? Are you shy?"

"She's just a kid, guys. Leave her alone," Diane said. "You can't buy her a drink, she's only eighteen."

"You going to school around here?" the blond man asked. "Van Hufferling?"

His friend finally spoke. "That's what I love about college girls - I keep getting older, they stay the same age," in some kind of approximation of Matthew McConaughey.

"Sorry, fellas. We've got an appointment," said Diane as she opened the door. Kim pulled his skirt up against the back of his legs as he got into the car. Even something as simple as getting into a car had a high degree of difficulty as he was still figuring out how to move in heels, and in a dress, but he managed to do it without humiliating himself.




Kim Gets Off to College Ch. 02



"Well, we'll be at the hotel bar tonight if you change your mind," the man said, as Diane kicked the car into gear and drove away.

"See?" Diane said as soon as they'd cleared the parking lot. "You're gorgeous."

"Maybe as long as I keep my mouth shut."

"What did you think of those guys? Were they cute?"

"What?" Kim exclaimed. "I don't know. I don't think about guys like that, I'm not gay."

"Stay in character!" Diane shouted. "Of course you're not gay. You're a girl. So- what do you think, Kimmy. Were those guys cute?"

Kim hesitated. In character, he thought. "Sure, they were kind of cute. The blond one - he reminded me of Tom Jane."

"Oh, totally, I can see that," said Diane. "Maybe we should meet up with him later -"

"I can't get into a bar!"

"A pretty girl can get around that little problem pretty easily. I bet he has a big cock too..."

"Diane! I don't want to hook up!"

"Why not? You're a girl, he's a man -"

"Because I'm -" Kim hesitated as he reminded himself to stay in character. "I'm a virgin." And I'm not gay, he said silently, in his mind.

"And you want to save your delicate flower for the right guy?"

"Yeah, exactly," Kim said with a frown.

Diane smiled. He'd stayed in character, basically. He could make that story work at school for a while, probably.

"Okay, time to work on your voice," Diane said. "Say something as a woman. With your feminine voice."

"I'm not an actor, I don't have a feminine voice all ready to pull out whenever I need one."

"Yeah, I know," she laughed. "You're gonna work one up right now. Now say something!"

"Say what?"

"Do I have to think over everything? Improv!"

"Uh- couldn't you feed me a line?"

"Ugh, fine. Say 'Oh, you're my new roommate? What a pleasure to meet you."

Kim repeated the line, in a high squeaky voice. It sounded awful even to him.

"No!" Diane shouted. "Don't do falsetto! Listen to my voice! Do I sound like a chipmunk?"

"No," Kim admitted.

"Look, your voice isn't very low to begin with. The problem is that you talk like a guy. Just raise it a tiny bit, but the important thing is to talk with a little more expression, some lyricism. Let your voice go up to emphasize words, don't talk in that boring, flat, monotone guy-voice you usually use."

"My real voice? You could phrase that less insultingly." Kim said, flatly.

"If you're going to complain, at least do it in your new voice," Diane groused.

"Okay," Kim said, trying to follow Diane's instructions. He raised his voice a bit and tried to let it be breathy and lyrical. "Okay, now I am talking like a girl. Oh my, nice to meet you. I love your hair!" Kim was surprised at how believable it sounded, just by raising his voice a little and trying to act a little Diane. "Hey, you know, this doesn't actually sound that bad."

"No, not at all. You're kind of a natural. Say some more stuff. Practice saying stuff you'll say at the mall."

"Uh, okay. Omigod, look at this cute dress? I wonder if they have it green. Does this make my ass look fat?"

Diane laughed. "Okay, that is pretty insulting to women in general, but you sound pretty good. I'm assigning you homework - listen to women singers and sing along, to get that girly inflection down right. All girl singers from now on."

"I have to read Cosmo, I have to listen to girl singers - how long do these assignment apply? Forever?"

"Just until you've mastered your act. Here, let's get started," and Diane started tapping her thumbs on her iphone, which she had plugged into the dash.

Kim laughed as 'Girls Just Wanna Have Fun' started blasting from the radio. 

Both Kim and Diane sang along, and Kim found himself falling more and more into character. He rolled down his window and threw his hand in the air, letting out a loud, high "woooo!" He shimmied his thin bare shoulders in time to the music, and gleefully shouted the words, experimenting with how loud he could get without losing the feminine quality of his voice. He kept looking over at Diane, and imitating his beautiful, stylish sister. If anyone Kim had ever met knew how to "work it" as a woman, it was his sister. Who better to learn from than the sexiest, sassiest girl he knew?

He couldn't really hit the high notes that Cyndi Lauper hit, but when he sang along in his breathy feminine voice one octave below, he still sounded like a girl, and he could carry the tune just fine.

The whole way to the mall, they listened to Diane's girly playlist. A few times, Kim noticed men or boys in neighboring cars watching the two beautiful girls sing and dance in their seats, checking them out. A few of the men even shouted come-ons at them, but Diane and Kim only laughed and left the boys in their dust. They had bigger fish to fry today.

When they arrived at the mall, Diane parked and opened the door.

"Wait!" Kim said. "What if - what if - "

"Look," Diane said. "I know you're nervous. Rehearsals are over. It's time to show you can do this."

"But if I can't?"

"You can. And this still isn't the real. It's like, before a play opens on Broadway, they do it out of town first to work out the kinks. That's what today is. But I promise you, by the end of the day, you'll have the confidence that you can fool anyone that you're a real girl. As long as you're willing to fully commit to your character and do what I say. Can you do that?"

Kim nodded. "But - what if I get an erection while we're walking around in there? I mean, the skirt'll hopefully hide it but-"

"Tell you what?" Diane closed the door and looked around. "Why don't you let me blow you again, then we'll really tape it down good so we'll be safe."

"What? Where?" Kim gasped. "We're in a parking lot."

Diane put her hand on Kim's thigh, and started to pull his skirt up. "Please, Kim, let me drink some more of your sweet hot jizz, I can't get enough of it and seeing you looking so fucking hot, it's driving me crazy. You're such a sexy girl, and you have such a perfect big dick-"

"We'll get busted!"

"Maybe..."

"Wait - let's do it inside the mall." Diane took her hand off his thigh as Kim continued. "We're both girls. Let's just go into the bathroom - or a dressing room!"

Diane giggled. "Okay, let's do it."

They left the car and walk across the parking lot. Kim had tucked his dick between his legs, but it had grown huge and strained against his panties. Kim tried to walk carefully (he was already getting the hang of his shoes) so as to not let his skirt fly up, and he kept checking his reflection in the windows of the stores they passed, but he was pretty sure nothing looked amiss. They just looked like two hot sisters walking through the mall, even if one of them seemed a little less confident than the other.

They turned heads everywhere they went. Teenage boys, old men - seemingly everyone couldn't resist the chance to sneak a peek at these two hot sisters in heels as they strutted through the mall. Kim started to like the attention, and he swung his hips even more, until he was affecting the same attitude Diane had, and mirrored her walk exactly.

They went into the Macy's and went straight to the women's section. As they walked by the lingerie department, Kim looked up at the mannequins, dressed in silky camisoles and fancy styles of lingerie he didn't even know the names for. Diane started collecting dresses from the racks while Kim just looked around at the clothing in a daze. 

He found himself thinking about what he'd look like in each outfit he saw. He saw the beautiful mannequins, striking their elegant poses, and imagined himself as each one, wearing a pencil skirt, or a cocktail dress, or a long classy evening gown with long gloves.

Kim had the feeling he was being watched, quite suddenly. He glanced out of the corner of his eye and saw an older woman, in her fifties, probably, and carrying about thirty extra pounds, looked at him. The woman sighed wistfully. Kim turned around and started walking away, but he heard the older woman remark to her husband, "I wish I had that body. I bet she can wear anything." Kim smiled. 

"Come on, Kim. Let's go try these on." Diane winked, and the two girls each grabbed three hangers and went to the changing rooms.

Kim walked into his changing room, and then turned as Diane snuck into with him and closed the door. Diane immediately dropped to her knees. "Take off your dress, you slut."

Kim pulled the straps of his dress over his shoulders and slithered out of it, while Diane pulled down his panties and his cock and balls escaped their imprisonment. Diane licked the underside of his thick juicy cock, from base to tip, then took the end of his dick into her mouth while she worked the shaft with her hand.

"Oh god" Kim gasped. Diane, even distracted as she was by her task, noted gladly that Kim had spoken in his girl's voice, even now. Good, his training is going well, she thought. 

Kim was watching in the mirror as his beautiful sister sucked his cock - the cock of a her twin, it looked like. She looked so sexy, the lady with the cock in the mirror. She had pert breasts under that stylish bra, with plump, sexy red lips, and big, dark eyes. It felt like he was watching a stranger, as she ran her hand over her sexy body as her big cock was taken further and further into the throat of her lookalike. 

He was so horny, he came in less than a minute, and Diane greedily took it down, not letting even a drop escape her lips. As Kim leaned against the wall, spent, Diane slowly stood up, running her hands over Kim's lean body until they were face to face. Diane opened her mouth, and Kim saw that it was white inside - still full of his hot jizz

Kim opened his mouth, and Diane kissed him, her mouth open as the hot, salty fluid ran into his mouth. Kim swallowed it down. 

"Isn't it delicious?" Diane asked.

It was a lot more than he'd tasted earlier - but somehow it seemed a little less gross than before. Actually, maybe it wasn't so bad - it certainly didn't nauseate him this time. He remembered what she'd said earlier about acting. He tried to believe it as he was saying it. "Oh my god, so tasty." He smiled what he hoped was a devilish, seductive smile.

"Okay, now resecure yourself and try on those dresses," Diane said. "And fix your lipstick," she added as she snuck out the door.

Diane and Kim both tried on several outfits, and kept meeting in the hallway of the changing area to admire each other, before venturing out into the store to find more things to try on. Ultimately, they bought a few things, all for Kim, that fit him perfectly and were super cute. A couple of outfits for classes, and one for going out on the weekend. Diane paid for everything.

Next Diane took Kim to the nail salon, and they both got their nails and their toes done. Kim had never had a manicure or a pedicure before, but he found the process enjoyable. He could see why women enjoyed it - you simply relaxed while magical things happened to your hands and especially your feet, thanks to these middle-aged Asian woman. His toes had never been so happy, and he had them paint them green with little pink butterflies. When they were done with his toes, they massaged his calves, and it felt wonderful.

After getting a pedicure, they both decided it was a real waste for Kim to walk around in long socks and Mary Janes, so they went to the shoe store and got a pair of steep wedge sandals that tied on with pink ribbons. Diane showed Kim how to tie them, wrapping the ribbons around his sexy things, which were elongated by standing in a wedge. Diane put them on her credit card and shrugged off their price as insignificant, and Kim thanked her profusely.

After that, it was time for lunch, and they went to the food court and got some healthy hummus and veggies.

While they were eating, Kim stayed in character, which he was finding easier and easier to do. He was talking about different kinds of dresses he'd seen already that day that he'd like to try on, when he found himself interrupted by a man's voice.

"Sorry to intrude," he said, "But I just had to say something." He was on a short side, with dark hair, and sort of a lopsided smile. He was wearing skinny jeans and a green zippered hoody with a Green Lantern logo on it. He looked probably about the same age as Kim - 18, or maybe 19.

"What do you have to say?" Diane asked.

"I guess maybe I phrased that wrong. I don't really have anything to say, I just wanted to talk to you."

"You've talked to me." Diane said, shooing him away with her hand.

"Not you. You." The young man turned to Kim. "You're the most beautiful girl I've ever seen and I couldn't just let you eat your lunch here and not come over and introduce myself, cause I was afraid if I did that I'd never see you again, and I'd never forgive myself."

"I'm the most beautiful girl you've ever seen?" Kim asked in his feminine voice, trying to seem incredulous, but in a way, completely excited to have scored such a massive compliment. He wanted to laugh, but managed to mostly contain himself - but he couldn't contain a smile. 

"There you go, look at that gorgeous smile. Hey, what're you eating, carrots? Aren't you hungry for some real food?" The boy sat down without being invited and leaned it, tilting his head conspiratorially towards Kim.

"We're watching our figures," Diane retorted. 

"I just got these. You want one?" the boy asked, holding up his to-go bag from Hot Dog on a Stick.

"Why did you buy them if you didn't want them?" Kim asked. He couldn't believe this guy was so close and was flirting with him and was completely taken in by the disguise.

"Cause I was standing in line already when I saw you sitting over here and I thought I'd better not come over empty-handed. Don't worry, they'll get eaten. I'm Wally, by the way."

"I'm Kim. This is my sister Diane."

"Nice to meet you. So what do you say? Either of you girls want to eat my weiner? Ha ha, I'm just kidding you, you know what I'm saying. You want one?"

Kim couldn't help but laugh. This guy was so brazen, but he had a warm smile and a quirky charm. And he was so brave, to hit on complete strangers like this! Kim couldn't imagine ever being so forward with a girl - back when he was a guy that is. Kim realized that Wally was now holding out a corn dog, seriously offering it.

Diane watched to see what Kim would do. She'd tried to protect him from these guys hitting on him, but it was inevitable that this would happen when she wasn't around anymore. What would Kim do? Could Kim get away from this guy? The weird thing is that he seemed to be enjoying all this male attention. Could he get out of this without freaking out?

Kim smiled and took the corn dog from him. "You want to see me eat this?" he asked, breathily. Then he held the hot dog in front of him and leaned forward, opening his mouth and talking just the tip into his lips. Then he pulled his head back and licked his lips. "Mmm, tasty," he said.

Then he thought back to the night before, and how he'd managed to deep throat the blue dildo. He again opened his throat, and opened his mouth wide, and he briefly deep-throated the corn dog. Diane's eyes went wide. "What is he doing?" she thought. "I've created a monster!" 

Kim looked up to see Wally's mouth agape, watching Kim deep throat his food amazed, then Kim pulled his head back, and bit off the end of the corn dog. "Mmm," he said. "You're right, this is good. It's been too long since I've had a mouthful of meat."

"Can I get your number?" Wally blurted out. 

"I don't think so," Kim laughed. "I'm not really looking to date anyone right now." Kim smiled wickedly. He'd just reduced this confident, cocky boy to pudding, with nothing but his own feminine wiles and a convenient prop.

"But you," Wally gasped. "Here, let me give you my number," he said, pulling out a pen and a scrap of paper. "I'm a sophomore at State. Seriously, call me, I'll take you out for a nice dinner or a movie or whatever you want. I'm a nice guy, really. Ask anybody. Here, follow me on twitter, too, if you're into that."

Kim smirked and took the paper. "Okay, I'll think about it."

"It was, uh, really great to meet you, Kim. You too, Diane." Wally practically tripped over himself as he scurried away.

Kim raised an eyebrow over at Diane, and Diane nodded. "Well, I'm somewhat impressed."

"Maybe I am an actress after all," said Kim.

"You're lucky you pulled that routine on a boy like that, instead of a grown man. Otherwise you would've wound up in a bathroom stall sucking him off for real."

"I'm not going to suck any dicks," said Kim. "I was just messing with him."

"It's not nice to tease boys too much without putting out at all," Diane said. "I mean, I don't mean you need to put out, but if you're not going to, just don't go nuts with the public fake blowjobs. It's not polite. You're gonna give that poor kid blue-balls. Why did you even do that?"

"It was just the first thing that came to mind," Kim said, smirking. "I guess after our, uh, recent activities I've got blowjobs on the brains."

"Yeah," laughed Diane. "You're a little obsessed."

"Me? You're the one who loves giving them so much," Kim looked around, remembering to lower his voice. "Besides, aren't all guys obsessed with blowjobs?"

"I guess, but most guys don't also deepthroat any cock-shaped object they come across."

"You can't possibly be talking about me," Kim said slyly. "I'm a girl."

"Of course you are, you little tease," Diane said as she stood up. "Now come on, finish swallowing that meat. We passed a store earlier where I saw all kinds of good stuff in the window. You still need a ton of clothes."

They navigated back to the boutique Diane was talking about, and Kim concluded that Diane definitely knew her stuff. Soon Kim was trying on outfit after outfit, and Diane kept adding things to the "keep" pile. Kim noticed the guy behind the counter, a cute tall latino guy with short styled hair, wearing a tight black t-shirt, kept checking him out and calling out compliments. 

"That looks beautiful on you," he said as Kim made a twirl in a red and black dress. "You have a beautiful body and that dress shows off your trim waste. It's good." Of course, he was trying to move merchandise, but it was still good to hear it, and Kim felt prettier and prettier.

But soon Kim noticed how big the pile of clothes had gotten, and looked at a few price tags. "Diane! We can't get all this stuff! You don't have this kind of money!"

"I'm a working actress, I can swing it. Besides, I bet I can talk this guy into giving us a discount." 

"Ramon? The cute latino guy?" Kim asked.

"You think he's cute," Diane asked.

"Well, yeah, I guess," Kim answered. Staying in character as a girl, trying to see him like a girl would see him, Kim continued. "He's got nice eyes, and his body is certainly fit. And there's something about him - the way he moves, I guess. He just seems like he'd know what he's doing." He tried to keep his voice down so the guy wouldn't hear him. "How you would you get a discount?"

"With my feminine wiles, obviously," Diane continued, "You'll see when the time comes. In the mean time, maybe there's a way you can pay me back for this stuff."

"Anything," Kim said. 

Diane leaned in and per lips up to Kim's ear, "Follow me into the changing room and eat my pussy."

Kim gasped. "But -"

"But what?" Diane asked. "I can do it for you but you can't return the favor? That doesn't seem very fair, especially considering I'm about to drop over a thousand dollars on your new wardrobe."

Diane put her hand on Kim's hip, on the side the hunky salesman couldn't see. She let her hand slip down onto Kim's ass. "What's the matter, Kim? Never experimented with lesbianism before? You're in college now. Everybody tries it. Don't worry. I'll be gentle."




Kim Gets Off to College



He stood in front of the mirror, naked, glass of white wine in his hand. Diane had left him a pair of shoes in his size, with heels that weren't high, and he stepped into them and tried walking. He looked up and down his body - he was soft, and thin, like a girl. He covered his penis with one hand, and draped his other arm over his nonexistent breasts, and cocked his hip in what he hoped was a girlish way. He arched his back and struck poses, and realized that he really did have a girlish figure - not in the negative way he'd thought about it in the past, but now he was realizing the beauty of the curve of his side, and his tight little stomach. His legs, his thighs - her legs, her thighs. Kim tried thinking about it that way, giggled, and took another swig from his latest glass of wine. He touched his lefts nipple and felt it perk up. He realized he was slowly stroking his swollen dick and looked at himself again in the mirror, when - the door opened.

It was Diane! She was back. Kim had left the door from the hotel room to the bathroom wide open, and Diane immediately saw what he was doing, even as Kim tried to turn his back and hide his erection.

"Oh, don't stop on account of me. I know I always want to have a little bit of fun with myself when I'm all smooth and sexy," she smirked and strode right into the bathroom.

"What are you doing in here! At least let me get dressed!"

"Oh, don't be so embarrassed, it's just us girls. Look, I got you pretty things to wear!" Diane held up several bags from the mall's department stores, including Victoria's Secret. "Here, if you're so embarrassed about your frankly perfect cock, then let's get you into a pair of panties first." With that she pulled out a pair of red lacey panties from the pink bag. She sat down on the toilet seat and grabbed Kim by the hips to pull him over to her, until his erect dick was floating in front of her face. 

"Step into this, please, Kimmy." Kim put a hand on her shoulder and stepped into the red panties with his right foot, then his left. Diane pulled the panties up his smooth legs and over his hips, although his huge dick could not be contained and was left sticking out well past his waistband.

"I think I might have a problem," Kim said. "Like, I'm not gay -"

"No one said you were."

"I mean, I'm really into girls. It's just that, when I look like a girl, well,"

"You sort of turn yourself on? The thought of looking pretty, the feel of the material on your hairless skin?" Diane smiled and licked her lips.

"Well, yeah," said Kim. 

"I know what you mean. I turn myself on all the time, especially when I'm wearing something really sexy. It's a common occurrence amongst the attractive."

"I mean, I guess I'm going to have to tuck it all the time? What am I supposed to do when this happens?" Kim asked, pointing at his huge, swollen dick.

"Well, the first thing, I suppose, is to drain it regularly," smiled Diane.

"You mean jerk off all the time?" Kim gasped.

"Sure," said Diane. "Don't act like you don't already do that anyway. Just, I guess, before every time you go to class or go out, just spank one out real quick. How many times do you do it a day right now?"

"That's none of your business," Kim tried to say, but he felt silly, standing completely naked except for red panties in front of his sister. "But a lot, I guess. It'll always come back!"

"Well, we'll figure that out. I think there's some kind of control undergarments we can get you. I don't know much about outfitting a drag queen, so this is the best I can do, for now. Obviously we can refine our system."

"Our system?"

"Sure, little sis," Diane smiled. "I like this idea of you going undercover and getting a woman's education and I'm going to provide material support. Do you know how many free clothes I get now that I'm a working actress? I think we wear the same size. Actually, let's find out. We need to get you dressed. Athough - maybe we should take care of your little problem," she smiled hungrily at his still-erect penis. "Do you want to handle it yourself or shall I give you a hand?" she asked suggestively as she ran her hand along the bulging front of his panties, just grazing the tip of his cock -

"Oh god," said Kim, for he desperately wanted Diane to touch it further, but his shame won out. "No, get out of here for a minute."

"Okay, I'll back off. I'll just have a seat right here," said Diane, as she hopped up on the counter and crossed her legs, Indian-style, flashing Kim a look at her blue panties beneath her skirt.

"I can't do it with you watching!"

"Well, I can't leave. We're on a schedule! If you're gonna be a prude about it, I guess let's just keep working on Project: Make Kim a girl. Next up? Let's get you dressed, and then I'll show you how to do your makeup."

"But," meekly objected, feeling his aching member straining against the thin lace of the panties, before he relented. "Okay, I guess."

Diane had thought of everything. While she was out, she had purchased gel breast forms that adhered to his perfectly hairless chest and were held in place by a perfectly fit red lacey bra that matched his panties. He looked at himself in the mirror, and realized that the breasts looked completely real. "I figured if I'd let you choose, you would have picked boobs that were unrealistically big," said Diane. "So I got you ones that match mine! Really the perfect size - a nice B+. See, we match!"

Diane walked over next to him and took her shirt off, ripping it off over her head with one motion. She was wearing a black version of the same bra Kim wore. Diane grabbed Kim by his hips and pulled him to her, until they were chest to chest, with their breasts rubbing up against each other. They were the same height, and their breasts were now the same size. Kim looked down at Diane's real breasts, resting on his fake ones. He could feel Diane's breath on his face.

Kim stepped back and looked in the mirror. He reached up and gave his breast a squeeze- it even felt real to his hand! And strangely, the feel of a hand on his prosthetic breast created an interesting sensation on the other side of the gel, as the form rubbed against his erect nipple. Diane reached over and grabbed his other breast, squeezing it. 

"Wow, this really feels real. See, just like mine," Diane said as she grabbed Kim's hand and brought it up to her own breast. "The nipples on these falsies feel just like the real thing? See?" she asked as she put Kim's hand under her bra to run his fingers over her aroused nipple, which responded to Kim's touch.

Kim's dick was rock hard in his panties, with the top three inches sticking right out above his waist band. He tried to will it to relax, but found himself powerless. He started to lean towards Diane, when she broke the spell by speaking. "Let's dress you up!"

Next Diane brought out a dress for him to try on. The skirt was tight and short, but the top half of the dress was flowy and only half there - it left his bra exposed in several spots, as well as a great deal of his back and his perfectly flat belly and tiny waist, while some folds of the flowing fabric fell down over the front of his skirt, concealing the bulge of his cock completely. The back side of his skirt was remarkably tight, revealing a visible panty line showing the tight cut of the red panties. His ass looked fantastic, like a tight little Asian ass. 

"Damn girl, you look fine!" said Diane, as she watched Kim admire himself in the mirror. Diane reached out and squeezed Kim's ass, with most of her hand in the right buttcheek, while one finger sneaked in between his cheeks and ran up under the skirt to just trace across his taint and over his panty-covered asshole. Kim yelped with surprise. 

"What are you doing?" asked Kim.

"Just grabbing me a handful of that gorgeous ass. Welcome to being a woman. Sorry to say, but you better get used to it, if you're going to walk around looking this hot."

"Well maybe I should tone it down a little then. Where, you know, slacks and stuff - "

"No sister of mine is going to look dowdy!" said Diane, loudly. "Your best bet at getting away with this and cashing in on this scholarship is to fool everyone, and the best way to do that is to be incredibly hot. So that's what we're going to do. Haircut time!"

Kim sat down on the toilet while Diane busted out her haircutting kit, which she always kept with her in her trunk. Kim had always worn his hair long, because it grew so straight and shiny. Girls had always complained to him that they were jealous of his naturally gorgeous hair, so he had always just grown it out without giving much thought to it. But he had also always resisted people wanting to cut it, since there was never a shortage of people telling guys to cut their hair short or joking about how he looks like a girl. Maybe they were right, Kim suddenly realized. 

Diane didn't want to hear Kim's protestations, though, nor did she feel that Kim was qualified to choose a haircut. Instead, Diane wanted to just cut it like she liked, then show it to Kim when it was done. "Trust me," she said. Kim finally relented, and Diane began wrapped a garbage bag around Kim's shoulders and started cutting.

Kim wished he could at least see a mirror. As it was, there was nothing for him to look at but Diane's bra-clad tits bouncing in front of his face as she cut his hair. His dick was as rock-hard as ever. He wished he could do something about it, but not with his sister here! If only she would decide she needed a cigarette break or something. But there was no break, only a lengthy and detailed haircut.

"How long is this going to take?" Kim asked.

"It'll be done when it's done. Now let me do my job," Diane said. "Do you want to look like a supermodel or do you want to look like a cheap whore?"

"A supermodel, I guess."

"That's what I thought." Some more moments passed. 

"I didn't want this, though. I'm just a regular guy. I'm not a drag queen."

"You're just a regular guy trying to get an education. And this'll be an education, too. Probably an even more valuable one than what you'll get from your classes. Trust me, Kim. I know this seems crazy, but I have a feeling that soon, you and I are going to laugh about this. I bet this turns out to be the best thing that ever happened to you. Okay, your hair is done."

"Can I see?"

"You know what? Maybe it'll be better - yeah. Let me do your makeup first."

"Shouldn't you be giving me a makeup tutorial?"

"I'll do that tomorrow. First I want to just experiment, and I want you to see the whole package all at once. It'll blow your mind." Diana smiled that devilish smile. "Trust me."

Kim smiled back. "Okay, let's see what you can do."

Diana smiled. She hiked up her skirt so that she could straddlee Kim, and sat down on skirt-clad lap, then reached for the makeup.

While Diana worked away, explaining the theories of what she was doing, Kim couldn't even pay attention. He was too horny, with this hot girl sitting on his lap, in her bra, with her skirt hiked up around her waste. He glanced down. He could see the crotch of her panties! And it was wet?

As she worked, Diana scooted her little bottom further and further up his lap, pulling Kim's body closer. Her ass kept creeping up until she was sitting on the base of his dick - he was sure she could feel it. While her face still seemed focused on her task, expertly applying makeup to his face, she moaned softly and tilted her hips forward. She started riding softly back and forth, rubbing her pussy on his cock. She was practically purring.

"What - we can't do this, I told you," Kim barely managed to say.

"Shhhh," said Diane, as she rubbed herself on his dick. "Lipstick..." she purred. "Make a kissy face at me."

"Oh god, you're going to make me come," he said.

"Not until I tell you. Kissy face."

Kim did as he was told, plumping up his lips to mimic the face that Diane was making it at him, even as she ground her pussy into him. Diane applied the lip gloss lovingly to his lips. 

She put the cap back on the lip gloss and laid it aside, then she leaned in slowly and kissed Kim gently on the lips. He leaned his head back and let himself be kissed - the graceful curve of his neck, like a beautiful girl -

"I'm done," said Diane. "Do you want to look at yourself in the mirror?"

With that, Diane straightened one leg, and with her dancer's gracefulness, pirouetted away. 

Diane reached her hand out to Kim.

Kim reached for her hand - but Diane pulled hers back. "Do it like a girl," she said. Kim, understanding, turned his hand so that it was like he was holding it out to be kissed, and Diane took it and helped Kim to her feat.

Diane put her hands on Kim's shoulders, and turned him towards the mirror. He wouldn't have recognized himself. Diane had given him almost the exact slightly asymmetrical same haircut Diane had. The makeup, too. Those two girls could be twins, he thought. Wait, not those two girls! Diane and me. I'm a boy! But looking at himself in the mirror, there was nothing that would give him away - nothing! He almost felt like a girl - wait, what did that mean? 

"My god," said Diane, "we could be twins!"

Kim laughed. "I was just thinking the same thing."

"You're fucking hot!"

"I think you're right."

"If we got out together, guys are gonna hit on us like crazy, you know that, right? Guys are nuts about twins. Every one of them always thinks he's the guy who's gonna sweet talk these two sisters into lezzing out on each other or co-blowing him."

Kim laughed again.

"You know, I actually have given half of a duel blow job," she continued. "My god, that was hot. He ended up blowing his load on both of our faces, then we made out and licked the come off each other's tits, the whole shebang. He was hard again within two minutes and then fucked both our brains out."

Now Kim said nothing. He was picturing Diane in that scenario with another girl - actually, he realized he was imagining Diane and himself, Kim, or rather herself, Kim as a girl, the two of them with jizz dripping down their chins, licking each other's bodies.

"Oh, that reminds me," Diane said. "I got you one more thing." With that she reached into the tall bag and pulled out a huge blue dildo.

"What?" shouted Kim. "What the hell am I supposed to do with that thing?"

"Put in your top drawer next to this bottle of lube," said Diane. "Look, it's part of the disguise. What if your roommate looks in your top drawer and doesn't find any dildos or vibrators at all?"

"I guess that makes sense," Kim said, as Diane handed the thing over. Kim weighed it in his hands - it felt almost real. He ran his fingers along its underside. "Why did you get one so big?"

"It's the same size as your cock," laughed Diane. "Or at least I think it is, right?"

Kim blushed, then reached down felt his dick with one hand, while he held the dildo with the other. She was right! It somehow felt bigger when he was holding this beast in his two little hands, so close to his face and his mouth - "So I guess I'll just keep this in my drawer."

"Or you could use it. It's a vibrator too. See?" Diane said as she reached to the base of the dildo and clicked a switch, causing the entire thing to vibrate.

"Guys don't use vibrators."

"Don't they?" Diane laughed. "Sorry to laugh, but I think I have a little more experience with what guys do in bed than you do. A lot of guys like to hold a vibrator up tight to the base of the underside of their dick, or their taint. Some guys even love shoving stuff like this in their assholes!"

Kim turned off the vibrator. "Not me," he said, although he wasn't nearly as sure as he sounded.

"Well, you don't have to do any of that stuff," said Diane as she took the dildo and held it up to her face. "Although it never hurts to experiment, you know?" She looked in the mirror and nuzzled the dildo. Kim stepped close to her and watched.

"See?" said Diane. "We definitely look like sisters. I could see how a guy would be really into this, watching two chicks do this" and she licked the tip of the dildo. "Mmm," she said, before opening her mouth wide and accepting the entire head of the huge dildo into her mouth, where she sucked up and down on it several times. Kim watched her in the mirror transfixed by these two beauties, one of them giving oral to this tremendous blue dildo -

Diane released the rubbery cock from her mouth and held it between their two faces. "What are you waiting for, slut?" she said.

Without even thinking, Kim opened his mouth and licked the dildo, while Diane did the same. Kim stuck out his ass, which looked fabulous in his tight skirt, bending down and licked all the thing all the way from balls to tip, while watching himself (or herself?) in the mirror. Then when he reached the tip, he opened his mouth while Diane stuck the cock into it. He put one hand on the dildo's shaft and pumped up and down while he tried to open his mouth wider than ever to accept this huge dick into his mouth.

"Get on your knees while you do that, whore," said Diane.

Kim's lips reached as Diane pulled the dildo away from him, but he obediently dropped to his knees and tilted his head back, his red painted lips parting slightly, hungrily.

Diane held the base of the dildo to her crotch, holding it out like it was her own dick. "Suck it, bitch," she said.

Kim had never been spoken to his life like this before, but he could not resist. He rose up on his knees and took the rubber cock into his mouth eagerly.

"That's a good girl," said Diane, running her fingers through Kim's long, shiny hair. She let her fingers linger behind Kim's ear, where she liked to be touched, and she could feel Kim responding. She smiled. She couldn't believe how easy it had been to turn her little brother into a crossdressing, cocksucking whore. It was turning her on so much, not so much pretending to be a guy herself (she couldn't feel the work Kim was doing on her rubber cock,) but seeing Kim, who might as well be her exact double, with that huge dick in her mouth. God, how she loved to suck a big dick. A big dick like the one on her brother.

"Deep throat it," Diane said. "I know you can do it. I'm great at it, and we're sisters." Kim looked up at her, a bit frightened. "Just relax your throat muscles and accept it." She said, softly, as she put her hands on either side of Kim's head and pulled it towards her, driving the dildo further and further down Kim's throat.

Kim could feel the huge, spongy thing going down his throat. It filled him up completely - he couldn't breath! Yet he reached up with his own hands, grabbed those rubber testicles, and forced the dildo further into his throat until only the balls remained outside his lips. He could feel his own cock, rock hard, straining against his panties, beneath his skirt.

"My god, you're talented. Look at yourself," said Diane, pointing him again towards the mirror. He saw a beautiful girl, her new do now mussed into 'sex hair,' with a huge dildo down her throat, so big that as he moved it in and out, he could see the head of the cock moving up and down his own throat. "Don't you just wish that were a real cock?"

Kim pulled the cock out of his throat, and gasped for breath. "A real cock? No!"

"Well, I do," said Diane. "Give yours to me," and she dove to the floor, pulling Kim's skirt up.

"No, we can't," said Kim, desperately trying to hold his skirt down and keep his legs together against the onslaught of his sister. But he couldn't resist - her hand found his cock, and was already stroking it through his red panties.

"Pull your skirt up," said Diane, and Kim obeyed. Diane pulled down Kim's panties, and his eight inch cock spilled out, hitting her in the chin. "Oh my God, you're so hard. Give it to me," said Diane, as she opened her mouth wide and engulfed his cock in her mouth. Kim had been so turned on for hours, ever since he first saw himself in the mirror standing in high heels, and he had never even gotten a blowjob in his life before, that his balls tightened immediately, getting ready to spew their seed.




Kim Gets Off to College



"Give me...give me..." Kim stuttered. He was in such ecstasy that he could talk straight. "Give me the dildo," he said. Diane, without taking his cock out of her mouth, passed him the big blue dildo, which he slapped into his fake tits, then brought up to his face, to lick it, imagining that he was Diane, sucking a dick -

"Give me that cum" Diane said, letting the cock out of her mouth while she stroked it furiously with both hands, working her elbow to stroke the entire gigantic cock. "Give it to me," she said, "right on my face, I need it," and Kim obliged. 

He thrust his hips and moaned as rope after rope of hot white jizz exploded onto his sister's face. Diane groaned with delight and licked her lips. She immediately went back to licking the tip of Kim's cock while it spewed a bit more, jumping and kicking with every orgasmic touch. 

Then Diane crawled up Kim's body until they were face to face. Kim saw the come dripping from Diane's forehead and nose, and hanging off of her plump lips - it was insanely sexy. She kissed Kim, and he opened his mouth willingly. He could taste his own jizz - salty but sweet, on his lips. It was just as he had fantasized, two beautiful sisters swapping cum after a duel blow job.

"I can't believe we just did that," said Kim, after they made out for a while.

"I can't believe we've never done that before," said Diane. "You've got the best cock I've ever seen. It's a real shame to disguise you as a woman. But you also make such a sexy woman, it'd be shame not to."

"This is all very confusing," Kim said, as he got up and looked at himself in the mirror. He looked just like some club girl, making a walk of shame home the morning after.

"Being a girl is always confusing," said Diane, laughing. "Now let's get some sleep. I've got a lot more to teach you tomorrow before you'll be ready to meet your roommates!"