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.