Kim Gets Off to Collegebysexykitsu©
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..."
"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."
"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."
"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 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."
"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.