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 teaching him to submit, and feminizing him into Kitty.

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

Serving Time

by Kris Cherita

Chapter 7

"You said Nova could tell me why Lana doesn't like being humiliated," Kit said to River as she emerged from the toilet. He'd gotten used to hearing women urinating in the toilets, and it barely even turned him on anymore.

River looked at him warily as she washed her hands and he walked over to the dryer. "Did you ask her?"

"I'm not that brave. I thought maybe you could tell me the story."

"Short version? How much have you heard about Eric/Erica?"

"The, uh, one who was here before me? Not much."

"Erica was very good looking, even pretty, and openly bi or pansexual, at least when it was safe. They settled in here very easily, perfectly happy to be seen as just one of the girls. Didn't mind crossdressing or makeovers -- they even wore that gingham abomination you were offered into town, on their first weekend. Not trans or non-binary, just genderqueer." She shook the water off her hands. "Just the kind Lana likes, and they hit it off pretty well. There's even a rumor, that I can neither confirm nor deny, that they were fucking each other -- anally, of course. Lana likes cocks enough that she straps one on sometimes. She might even suck yours if she can spit your come back into your mouth so you swallow it."

Kit decided to ignore that. "What happened?" It was barely two years since SCOTUS had voted 7-6 to repeal the revised Comstock Act and its nationwide ban on contraception and abortion, but even in the states where contraceptives were legal and theoretically available, a lot of people still preferred titfucking, oral and/or anal sex as ways of avoiding pregnancy.

"Nova happened. Hazel, who was Amber and Erica and Serenity's roommate, got probation and a few days later, Nova was admitted here and given her bunk. And Erica was a movie buff, just like Nova. Done some acting, some modelling, some dancing, and seen a lot of the same films Nova had. Erica and Lana stayed fuckbuddies for a while, but Lana realized that Erica was much more interested In Nova, and not just because of her boobs, though I think that was part of it. But no-one dates Lana for her conversation, even if they like asses more than boobs. And that's what Lana has against Nova; she feels she stole her lover and humiliated her, and that's why she makes her eat out her asshole, knowing that that was one part of her that Erica was into. Come on, we don't want to be late for dinner."

Kit nodded. Ximena was being released onto probation the next day and going to stay with her Abuela in San Diego, and this was the last meal she was going to cook before handing her job over to Stacy. Danning had given her money to buy better ingredients than usual, and had also paid for a cake and some bottles of soda for her farewell party. River dried her hands and they walked towards the kitchen.

*

"It's a party," Amber said, as she slithered into her cheongsam. "You can't just wear your scrubs."

"They're all I have," Kit replied, "and it's not like anything of yours is going to fit me."

"Ask Mia," Serenity suggested. "You've borrowed her clothes before, and they suited you."

"That was to go into town."

"Don't be a party pooper! You'll have a lot more fun if you get into the spirit of it," said Nova, searching through her collection of T-shirts. Kit looked at the trio, and headed down the corridor to the dorm Mia shared with Naomi, Hailey and Sky. He knocked on the door, and was told to come in. He was unsurprised to see that while Naomi was almost completely dressed in a high-collared pink blouse, black knee-high socks and a high-waisted black miniskirt barely long enough to cover her white bikini briefs, Mia was wearing nothing but a black thong.

"Hello, Kitty," said Naomi, then covered her mouth as she giggled.

"What's up?" Mia asked, as she donned her Ouija board t-shirt, the nipples visible as nubs behind the Yes and the No.

"I was hoping you could lend me a pair of pants to wear to the party."

"Sorry, no. I don't have any here. A skirt or a dress, yes. Have you asked River? She's about your size."

"She only has one pair of shorts, and she's wearing those."

"Pity. You've got nice legs and a cute butt; they'd suit you. How about this?" She reached into her locker and pulled out a black spaghetti-strap dress. "We don't have to hide how big your feet are, so you don't need the maxi skirt -- besides, I was going to wear that. Try this on."

"You're kidding!"

"Everyone should have a little black dress," said Mia. "Just strip off and put this on, and if it doesn't feel good, I'll try to find you something else -- not that there are many other options."

"How come you have so much stuff, anyway?" Kit asked. "How can you afford it?"

"I have a side hustle. I do website design for a few businesses, and some of them give me staff discount. Mostly goth or geek stuff, but also some Harajuku fashion. Oh, and sex toys. It's still more expensive than the second-hand stuff from Nifty Thrifty or Dollar Domain, but you get more choice. And if you think this is good, you should see my closet at home," she said, more than a little wistfully.

"Do any of those shops sell any men's clothes?" Kit asked.

"Some of them do."

"If I paid for them, could you buy me a pair of men's pants?"

"I could," Mia replied, "but I'd need the money up front. And I'm not supposed to use my discount to buy stuff for other people. I can get away with doing it occasionally and calling it a gift, but a lot of the other girls have already placed orders and there's already a waiting list..." She handed him the dress.

Kit took the hint, and stripped out of his scrubs pants and tie-dyed t-shirt, then pulled the dress on over his head. He adjusted it so that it was straight, then looked at Mia almost defiantly.

"Not bad," she said. "A little baggy up top 'cause you don't have any boobs, but -- turn around? -- yeah, your butt looks good."

"Thanks," he said, awkwardly, as he turned back to face her.

"There's no obvious bulge, and the short skirt shows off your legs, too. You want some stockings? I think you liked the ones with the skulls --"

"On you, yes."

Mia shrugged. "- or I have fishnets or spiderweb patterns, if you prefer. Pity none of my boots will fit you; your legs and butt would look even better if you wore heels."

"I'll pass, thanks."

"We know you here: you don't need to pass." She smiled at her own joke. "I'm sure I could get you a good pair of boots in your size from one of my shops, though they wouldn't be cheap even with my discount, but your sneakers or slippers will have to do for now. You want a bra to pad out that chest? I have one that should fit you and won't show any straps."

"No thanks."

"Some makeup?" Naomi suggested, flashing her panties at him as she pulled on a pair of striped thigh-high socks. "Just eye make-up. A lot of straight guys are wearing it now." When Kit didn't reply, she asked, "How're you going with The Forever War?"

"Finished."

"Did you like it?"

"I hadn't expected the gay stuff, but yeah, it was a good book. And I'm enjoying the anthology, too. I just read that John Varley one about the computer and the Vietnamese woman."

"'Press Enter'," said Naomi, nodded. "If you liked that, there's a Varley collection in the library. The Barbie Murders. And some Theodore Sturgeon that you might like, too."

Kit was about to reply, but Mia reached up under the hem of his short skirt and gently grabbed his erection, stroking it through the satiny fabric of his panties. "One of the great things about short skirts is that make this so much easier. Ooh, it feels like you're enjoying this," she purred.

Kit gasped in surprise, then drew a deep breath. "I'm surrounded by hot young women every day," he said. "Is it any wonder I'm horny all the time?"

"Nice save," said Mia approvingly as she withdrew her hand. "if you don't want anything else, I'll see you at the party. I have to finish my make-up, but I'll join you later. Have fun."

*

Kit hadn't expected Danning to attend the party and propose a toast, but was even more surprised to see June wearing something other than her usual pink scrubs and nurse's shoes: she'd dressed up in tight jeans and a red satin blouse that showed enough cleavage that Kit had to remind himself to look at her face instead of her boobs. Neither of them showed any surprise that he was wearing a dress, not even raising an eyebrow. Instead, Danning complimented him on how much his schoolwork had improved and asked what he hoped to do when his sentence was over. "I don't know," he admitted. "I'm not looking forward to going home. All of my brothers are in jail, now - Chad got drunk after not qualifying for the Sperm Races and assaulted someone - and Dad is talking about moving to Texas, says he's tired of living in what he calls a pink-and-blue state," he absent-mindedly ran a hand through his baby-pink hair, "and go somewhere where men are men and women can't leave. I think he's hoping one of the states will pass a Free Use law."

Danning grimaced. The SCOTUS of the 20s and 30s had frequently come down on the side of "state's rights", and not just on decisions such as Obergefell, Roe and Loving: some states had effectively repealed some of the constitutional amendments that weren't in the state-approved Bibles. "I doubt that will ever happen," she said." It's on the ballot again for a few states, but the propositions always get voted down. Not just because a lot of men who might vote for it have mothers or sisters -- most of them are incels who'd happily fuck their mothers or sisters if they had the chance -- but because in a free use state, they'd still be losers. Other men will still get the more attractive women, and the incels would have to watch while they stand in line. Forget about sloppy seconds; they'd be lucky to get sloppy thirty-seconds."

"Which is longer than most of 'em would last," said Mia, who was standing behind Kit and chatting to Naomi.

Kit nodded. "I might look for a job and find a room near here, instead."

"We can give you some help with both," said Danning. "Some of the girls who're up for probation at about the same time as you are, have been talking about getting a share house near the community college; maybe you could move in with them."

"I wasn't really thinking of going to college."

"You probably could, if you wanted to. Maybe get an engineering degree."

"Yeah," said Mia. "You could say you were an engineer with social skills. That'd look great on a resume, if only for the novelty value."

Danning's mouth quirked slightly. "Anyway, come and talk to me when you decide," she said, and drifted away to talk to Stacy.

Ximena cut the cake a few minutes later, and Danning left as soon as she'd finished eating her slice. June hung around for another twenty minutes before retiring for the night, reminding them that the lights would be going out at midnight and they should all be in their dorms before then. Stacy began clearing the tables and stacking the dishes in the dishwasher, and Kit walked up to River and asked, "So, now that Xi's moving out, what happens to her bunk?"

"Why? Would you like to move in with us?"

Kit glanced at Stacy, and managed not to gulp. "Ahhh... I hadn't thought of that. I mean..."

"Danning usually only takes a few days to pick another woman who she thinks would be better off here than in jail, and you won't be the new kid any longer. If you want to change dorms, you'd better speak to her before that happens. She might say yes, she might not, but she'll ask us first."

"I think I'll stay where I am."

"That's up to you. Stacy's taking over Xi's job here, which means we'll have to reorganize our duties until Xi's replacement arrive. I want to stay in the garden, so someone will have to do our laundry. You want the job?"

Kit blinked. "What?"

"It's not all that difficult. One load for the sheets, another for clothes, and you can read or do other stuff while the machines are running. Unless the idea of handling our underwear worries you."

"Your..." He swallowed. "Is that going to be okay with Stacy and, um, Taylor?"

"I can ask them, if you like."

Before Kit could reply, Maggie stood on a table and announced, "Okay, according to time-honored tradition, everyone has to kiss the graduate goodbye. Xi, do you want us to line up, or should we spin the bottle?"

"No, I'll choose for myself," said Ximena, standing with her back to one of the other tables. She pointed at Regan, then beckoned to her. The redhead hurried over, and kissed Ximena quickly on the mouth. Maggie, Bri, Taylor and Lana were next, then Mia, Nova, Serenity, Naomi and Sky. When it was Freya's turn, though, the kiss went on for much longer, and then she beckoned to Stacy, who kissed her even more passionately until Xi slipped off her crop top, exposing her beautiful breasts. Stacy grabbed them and ran her fingers around Xi's dark brown nipples until they stiffened, then pulled off her own t-shirt and she crouched down to suck on Xi's nubs, making them swell even more. Kit felt his cock harden inside his panties as he watched the two women kiss and fondle each other's big boobs, and then Xi beckoned to Amber and unzipped her daisy dukes. She stepped out of her shorts and thong as she kissed the beautician, then guided her head down to her left breast. As Scott watched, amazed and incredibly aroused, Stacy rubbed her beautiful big brown boobs over Xi's wet and hairy cunt, circling her clit with her nipple while she suckled on Xi's right tit.

"Oh fuck," Xi breathed. "Stop fucking teasing me!"

Stacy chuckled, and kissed her way down Xi's stomach until she reached her cunt. She sucked on her labia, then ran her tongue between them, getting her wet before she slid her fingers inside her and sought out her g-spot. She circled Xi's clit with the tip of her tongue, as Xi beckoned to Jade. Soon, Xi was lying on the table, with Amber and Jade worshipping her boobs and Stacy fingering and licking her cunt. She beckoned Eden over and was kissing her as Stacy made her come. Stacy gave her cunt one more kiss, then walked to a chair as Amber took her place between Xi's thighs and Eden began sucking on Xi's breast, occasionally taking a break and kissing Jade instead. Xi beckoned to River, and kissed her until River peeled off her t-shirt and dangled her tits over Xi's face and Xi began sucking on them as enthusiastically as Eden and Jade were enjoying hers.

Kit was finding it increasingly difficult not to masturbate, despite being extremely disappointed at the idea that he was the only one who Xi wasn't even going to kiss -- and then Amber made Xi come for the second time that night, and after she'd recovered, she reached for River's daisy dukes, unzipped them, and pulled them down. She gently pushed Jade and Eden away, then flipped River onto the table beneath her in a 69. Jade and Eden stripped off and began playing with each other's cunts and tits as they watched the two women feasting on each other, and Amber sashayed over to Stacy, murmured in her ear, and then began kissing her way down her body to her cunt.

Kit was wondering who he should ask for permission to start wanking into his panties, when Xi raised her head for a moment and turned her head to smile at him. Then she pointed at him, crooked two fingers in a beckoning gesture, and then pointed at her ass. Kit, realizing what he was being asked (ordered?) to do, nodded and walked over to the table. He looked down at Xi's butt: he'd admired it before, but it looked even better naked. River, pinned underneath Xi, looked up at him and winked, and he began kissing Xi's spectacular ass, spiralling in on the hot little starburst at its centre. He held her cheeks apart, enjoying the feel of the muscular firmness beneath her silky-smooth skin, and ran his tongue up and down her butt crack until he was French-kissing her inviting pucker. He was disappointed not to be sucking her breasts or licking her clit, but if this was his assigned role in the school, he was going to do it as best he could. He probed her hot sour hole with his tongue-tip until she suddenly came, her sphincter contracting and trapping him. Her asshole relaxed a moment later, allowing for deeper penetration, and soon he was tongue-fucking her eagerly while River fingered her g-spot and sucked on her clit. A few glorious minutes later, he felt Xi began shaking and realized that it was because River was coming, which set Xi off again.

Suddenly, he felt a hand slide up his inner thigh, up under his short skirt, and onto his panty-clad cock, rubbing up and down the thin satiny fabric around his erection. Determined not to be distracted, he continued rimming Xi until she came again, and as he felt her butt shudder and her asshole constrict, he ejaculated into his panties, soaking them with jizz until they stuck to him like a second skin.

"Enough!" Xi gasped, and he kissed her cheeks again before she rolled off River and both women looked up at him, smiling dreamily. He looked around to see who'd been wanking him, and was astonished to see that it wasn't Mia, as he'd thought, but Serenity, who was licking her fingers clean with a grin just as smug as River's.

"Wow," said Nova. "Maybe we should make this a part of everyone's farewell party -- Kitty kissing their asses goodbye."

"Okay for you," said Lana. "She'll probably get parole before some of us."

"Maybe we could persuade her to stay," said Mia. "I think she likes it here."

Xi recovered her breath and sat up, kissing him on the forehead, and Kit found himself wishing he'd made an effort to get to know her better. "I'm going to miss all of you guys," she said, more loudly. "If you're ever in San Diego, call me." She twisted around on the table until she and River were face to face, and hugged and kissed her, each of them tasting her own juices on the other's lips and tongues and faces.

"Hate to be a party-pooper, but it's nine minutes to lights out," said Naomi.

"And don't forget your clothes," said Stacy, picking hers up off the floor. "I've got to get breakfast ready tomorrow, so this room better not look like a brothel."

Kit was heading for the door when Lana came up behind him and swatted him on the butt. "Looks like you're found your calling in life, Kitty-cat," she said in his ear. "Don't forget to brush your teeth. Goodnight."

(To be continued)