Serving Time

In 2044, 18-year-old Clint chooses to serve out his 3-month sentence as the only man in a girls' reform school rather than a jail. The women set about feminizing him.

All characters are 18 or over. Feedback welcome, as always.

Serving Time

by Kris Cherita

Chapter 5

Kit was dreaming of a picture he'd seen in one of his grandfather's old magazines from the days before commercial porn was mostly CGI: a medium shot of an attractive black woman wearing her panties on her chest with her huge breasts, nearly as big as her thighs, through the leg-holes, and the gusset held between her teeth. The photo had turned him on so much, even more than the pictures of the same woman showing off her tight little asshole and the bubblegum-pink interior of her cunt, that it had stuck in his memory without him really understanding why -- but he woke up with a huge erection, panties sticky with jizz and a burning desire to taste Stacy's cunt and fuck her tits, preferably at the same time.

He looked around the dorm. He couldn't see Nova on the bunk above him and couldn't tell if she was awake, but it was still early in the morning, more than an hour before the first shift for breakfast; Amber was rolled onto her side with her back to him, and Serenity seemed to be fast asleep, so he slipped out of bed and hurried towards his locker. He had pulled his cum-stained Hello Kitty panties down to his knees when Nova sat up and said, "Nice butt."

He froze, then -- taking care not to turn around -- finished undressing and dumped the cum-stained panties in the laundry hamper, then opened his locker. "Thanks," he muttered. "I like yours, too."

"Ooh! I might let you taste it one day," she teased. "Good dream, huh? Or couldn't you wait until Sunday."

"Just a dream," he said, grabbing a clean pair of pink frilly briefs from his locker and pulling them up over his erection.

"Anyone I know?"

"Maybe."

"Anyone in this room?"

"Not this time," he evaded.

"River?"

Kit didn't answer.

"Not even after she went down on you? Wow. Lana?"

"No."

"Okay, now I'm intrigued. Freya? She's hot."

"No."

"Mia?"

"No."

"Maggie?"

"Fuck, no!"

Serenity rolled over in her bed. "I'm guessing it's Stacy. She has the biggest boobs."

Kit didn't reply, and Nova laughed. "Dream on, Kitty-cat! No way on God's green Earth, or any other planet, is she going to let you even touch them. Not with any part of your body."

Serenity nodded. "Of all the things that are never going to happen, that's never going to happen the most. Unless she gets a brain implant installed, and Corrective Services isn't doing that in this state."

Kit shrugged. He knew that the implants, widely known as Stepford chips, were being sold as a "cure" for lesbianism, asexuality or gender dysphoria. Xcorp had not yet produced a male equivalent, and rumor had it that the software had simply been copied from the tradwife option used in their fembots. The vast majority of the chips sold to conservative parents to implant in their daughters before they were legally adult and able to prevent it. In states where this was legal, many young trans men left school on Friday and returned as girls on Monday. "Well, what if we win at volleyball again?"

"Don't even think it, Kitty-cat," said Nova, almost kindly. "Unless you've got some kinks you haven't told us about, you do not want Stacy anywhere near your genitals or your asshole. You know the saying that there's a fine line between pleasure and pain? She'd drag you so far over that line that you'd need GPS to find your way back."

"Stick with River," Serenity advised him. "Her boobs are nearly as big, and she seems to like you."

Kit shrugged. "Thanks for the tip," he said, as he climbed back into bed. His cock was still hard as bone, and he tried to think of something that would get it under control, but the idea of fucking Stacy's big beautiful brown boobs wouldn't go away.

*

It was a Friday, and Kit tried to pay attention during the classes to distract himself from that morning's dream. It wasn't entirely successful, and when classes were over, he tried diverting himself with video games. That worked reasonably well until he saw Stacy return to Pridemore after her shift at work, and he felt his cock stiffen in his panties and lost control of the flight simulator, crashing into the side of Mons Vitruvius.

"Kitty?" Serenity said as she passed by the door a few minutes later. "Dinner time."

"Coming," Kit said absent-mindedly, hoping his erection wouldn't show when he stood up. "Ah... just a minute." He hurried into the bathroom, and checked that it was empty before sitting in one of the cubicles. He realized that he'd already become so accustomed to answering to the name 'Kitty' that he'd almost forgotten that his name was Clint and now thought of himself as Kitty or Kit.

"I'm Clint," he said quietly. Somehow, it sounded wrong. "My name is Clint." That didn't sound much better. It didn't help that he'd never much liked the name. He thought for a moment, then whispered, "My name is Kit."

He blinked. Well, he decided, it's better than being called 'Cunt' every day, which was bound to happen if he maintained that his name was Clint. And he'd sort of chosen the name Kit for himself. "I'm Kit," he said, a little more loudly, then pulled his scrub pants and Hello Kitty bikini panties down, and looked down at his erection. "Not Kitty. I'm a man, not a girl. Wearing women's clothes doesn't make me a girl."

Even if you make cummies in your pretty panties sometimes? said a voice inside his head.

"I'm a man, and I'm straight," he told himself, a little more loudly than he'd intended. "I have a cock, not a clit, and if I get horny and have to ji - jerk off, it's because I'm surrounded by hot women who I want to fuck. Right?"

You're still wearing nail polish, said the voice, and you smell of women's deodorant and perfumed soap and your hair's still pink. That's why you switch the camera off when you call home. I bet if someone called you Clint, you'd wonder who they meant.

Kit glanced at his hands, and realized that he kept forgetting to ask Amber for some nail varnish remover, even when she'd trimmed his pubes and used nanogel to depilate his balls. "I know who I am," he said. He pulled up his pants, adjusted his panties to make his erection less obvious, and walked towards the door.

The voice followed him to the dining room. Are you sure?, it asked.

He grabbed his tray of food and sat down at a table with Mia, Serenity and Naomi. "You coming into town with us tomorrow, Kitty?" asked Mia.

Kit nodded. It would mean borrowing one of Mia's dresses again, but it was better than staying in the school. "Sure," he replied.

*

Naomi was sitting in the library, and looked up from her book when she heard Kit approach. She raised an eyebrow as he sat down at the next desk, and waited for him to speak. "What're you reading?"

"The Gate to Women's Country. Sheri Tepper. Why?"

"I'm getting bored with the computer games they have here, and I thought I might try reading something. Do you think I'd enjoy that book?"

"I don't know. What was the last book you read?"

"Catcher in the Rye, for English class."

"And the last one you enjoyed?" She waited for a reply, hoping he wasn't going to say Atlas Shrugged.

"I'm trying to remember... there was this book by Stephen King. Four short novels, one of them was about a kid who finds a Nazi war criminal living in his suburb... the Good Student, I think. I read the others, too, and they were pretty good, but the one about the kid and the Nazi, I read in one day. Before that, they gave us a bunch of old dystopias, and some of those were okay, so I thought since you're always reading and everyone says you like science fiction and weird shit -"

"I presume that's a polite way of saying 'fanfic'." She placed a bookmark in the novel, shrank it to a small icon, and opened a list. "I'm working my way through the sf masterworks --"

Kit looked over her shoulder. "The Forever War sounds interesting."

"It is. Or you could start with an anthology that has short stories by a lot of different writers, see which ones you like and check out their novels. Try this one: Best of the Best. The editors did a poll of readers to see which award winners and nominees had aged well -- a lot of science fiction really doesn't."

"I'll check it out. What's 'fanfic'?"

"People writing stories using other people's characters which are still under copyright. Mostly it's slash, which is the characters having sex. Sometimes it's straight sex or lesbian sex, but mostly it, uh, isn't."

Kit blinked. "Ah. Probably not my thing, then."

"Probably not, but I enjoy it. Let me know what you think of the book."

*

Sunday night came around, and shortly after the lights went out, Kit pulled a pair of Serenity's used panties out from under his pillow, fantasizing that they were Stacy's. He heard Amber and Nova switch on their vibrators, and then Serenity turned to face him and said, "Instead of sniffing my panties, would you rather go straight to the source?"

"What?"

"Would you like me to sit on your face? And I could play with you. If you come before I do, I'd expect you to keep going, of course."

Kit swallowed. "Your vibrator isn't working?"

"It is, but sometimes I like to be held after I've come. Are you interested?"

"Uh, sure!" He shoved her bikini panties back under his pillow, and she groped her way through the darkness onto his bed. She found Kit's face, kissed it on the cheek, then pushed the quilt down to below his hips and positioned herself above him as if they were 69ing, though she didn't remove his panties. She lowered her naked cunt onto Kit's face until it brushed against his nose, then giggled. "Whenever you're ready," she said softly, then gently nuzzled his panty-clad erection. Kit stuck out his tongue until he found her labia, then began licking up until he reached her clit, which he circled with the tip of his tongue -- then down again, down to her taint, and back, repeating this until her cunt bloomed and he could stick his tongue into her slightly sweet wetness, lubricating it before returning his attention to her swelling clit.

"You can use a finger," said Serenity, "as long as it's clean. No come or pre-cum on it."

"As you wish." He slid his index finger into her wet cunt, and was surprised to find it much tighter than River's or Nova's. He wondered if she was already having an orgasm, but her breathing suggested that she wasn't there yet. He tried to withdraw his finger, but her grip on it was too strong, so he pushed it further in, hoping to find her g-spot. He licked around her clit, and suddenly she began shaking, writhing, on top of him as she came. The sensation of her body rubbing against his was almost enough to make him come in his Hello Kitty panties, and he tried to control his breathing while her dripping cunt ground down on his face, but he knew that he was so close that it would be difficult to stop -- and when Serenity kissed his cock through his panties, he ejaculated as though a pump had been switched on, his jizz spurting through the thin fabric and onto Serenity's lips. She recoiled, startled, then laughed as she wiped her mouth clean with her hand, then wiped her hand clean on Kit's sheet.

"I see you enjoyed that," she said, as she swivelled around on the bed and lay beside him, her mouth near his ear, "but we could have had even more fun if you'd held off coming."

"I thought simultaneous orgasms were supposed to be a good thing," he muttered. He noticed that Nova's and Amber's vibrators were no longer buzzing.

"Some women are satisfied with one orgasm, yes," she said, "and one is a lot better than none. But --"

"- most men can't even manage that," said Amber.

"You've been fucking the wrong men," said Nova.

"Maybe. But I think I'll stick with women. Men don't have enough staying power."

Kit turned to Serenity. "It's because you're so sexy, especially when you come, that I got so turned on and..."

"Uh-huh. Nice try." She smiled crookedly. ""I think the problem is that too many young people learned to masturbate as quickly and quietly as possible so they don't get caught. You need to get past that. Don't concentrate on your own orgasm -- if that was all you wanted, you could do it yourself and you wouldn't need anyone else there at all. Think about how good women's bodies feel, how they taste, how good it feels to turn us on and make us come. Because you're eighteen and you can come, what, five or six times a day, tops?"

Nova laughed. "I can do that in a few minutes. I bet you wish you could."

"Fuck yeah," Kit admitted.

"And it'll get worse when you're older."

"Gee, thanks."

"It's not all bad," said Serenity reassuringly, "not if you learn to get even better with your mouth and your fingers. I can teach you, and you seem to be a pretty quick learner."

"Unless you think you can learn to have multiple orgasms, like a real girl," said Nova.

Serenity fondled Kit's cum-soaked panties and grinned. "I see you like that idea."

"Do you want me to go down on you again?" Kit asked. "I'd be happy to."

"No, I'm good. Don't waste the afterglow. Just hold me for a while, then I'll go back to my own bed. These bunks are too narrow for two of us to sleep in."

"Can we try again on Wednesday?"

"Maybe." They lay there for a few minutes, snuggled together, then she climbed over him and returned to her own bed. "Goodnight, Kitty. Sweet dreams."

"Goodnight."

(To be continued)