Serving Time

Serving Time

by Kris Cherita

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, including dressing him as Janet for his first viewing of The Rocky Horror Picture Show, then as their sissy maid.

Chapter 13

Though he would never have admitted it, Kit felt a slight pang on Tuesday morning when the maid's dress and other Rocky Horror outfits were given to Hailey to return to the costume hire shop. He did his best to distract himself with his studies, and in the evening, having no laundry to do, joined the women playing board games and watching Sick Sad World. He was initially disappointed on Wednesday night when Serenity said she just wanted to use her vibrator for a quick orgasm that would help her get to sleep, but she crept into his bed naked and acted as little spoon as she did it, and holding her as she came and feeling her ass shaking so near to his cock, separated from it by only the thin satiny fabric of his panties, had him coming only an instant later. She rolled over and kissed him quickly on the mouth, then hurried back into her own bunk.

It was raining so heavily on Thursday that the volleyball game was cancelled, so he volunteered to do the laundry for his dorm and waited in the vain hope that River might come in and lick his asshole again, or failing that, ask him to lick hers. When she failed to appear, he masturbated into one of Nova's bras before putting it into the wash, but he was still feeling frustrated and sourly horny when he went to bed that night.

On Saturday morning, Serenity and Mia dressed him in gothic drag again for a bus trip into town, while Amber did his make-up to help him pass. Serenity, Nova and Mia then took him into the mall's lingerie boutique. When Kit asked why it took four of them to buy Serenity one g-string, Mia replied, "Girls like shopping together, especially for clothes, and we might see something we like."

"Don't get your hopes up," said Nova. "They don't let you try on panties, for health reasons. And none of us need a new bra, unless you want to buy me one? Though this one would suit you," as she picked an orchid pink training bra out of the display. She looked from Kit to Serenity, and nodded. "You're both close to the same size, when you're not wearing falsies."

"No thanks. That's not why we're here," Kit replied.

Serenity examined the display of g-strings, then stepped aside and pointed to them. "What colour would you like?"

"You choose," Kit replied.

"It's for you," Nova reminded him. The clerk at the counter, an attractive Asian woman, looked over as though she'd heard. "I mean, it's for your benefit, and you're buying it."

"You may want to borrow it when Serenity's not wearing it," Mia added. "It'd probably fit you."

Kit bit his lip, and turned to Serenity. "Do you have a preference?"

"You choose. If I don't like it, I'll tell you."

Kit walked towards the display. "Something close to your own skin tone. Not beige or white, but a paler pink than this," he said, pointing to a Barbie-pink thong. "More like the colour of that bra."

"You could ask the saleslady for help," suggested Nova, with an unconvincing attempt at sounding innocent.

Serenity picked out a baby-pink thong, a small triangle of mostly see-through lace and narrow elastic ribbons. She checked the size, and asked, "Like this?"

"Yeah, that looks great."

"Okay then," said Nova, as Serenity handed the thong to Kit. "Go and tell the saleslady it's for you."

"What?"

"And tell her you're an ass-licking pantyboy."

"Why the fuck would I do that?" Kit raised his voice just enough that the clerk looked in their direction, her face inscrutable.

"Because if you do," Nova replied, "I'll let you motorboat and suck my boobies next time you play with yourself."

Kit stood there with his mouth open for a moment, then muttered, "You're kidding."

"You have witnesses," Nova said softly. "Say it to her, loudly and clearly, and you can suck my boobies for as long as you like until you make cummies in your panties. I'll even jill you off, if you like."

"But... what if she calls the cops? If I get arrested, I could end up in a real jail!"

"Why would she, as long as you pay for the thong first? She'll just think you're being a smart-ass. And it's not like you're going to be shopping here regularly."

Kit stared at her, then at Mia and Serenity. The goth looked impatient, and Serenity slightly uncertain. "Okay," he said quietly, "if I do this, I get to suck your tits until you make me come. Show me your hands so I know you don't have your fingers crossed."

Nova held her hands up as though surrendering. "You have my word."

"Shake."

Nova smiled, and shimmied so that her unrestrained breasts wobbled enticingly. "Satisfied?"

"Not yet. But remember, I have your word, and I have witnesses."

"Sure," said Mia, and Serenity nodded.

Kit swallowed, accepted the g-string from Serenity, and walked up to the counter. The saleslady scanned the price tag and removed the security device as he waved his phone over the card reader. "Good choice," the woman said neutrally as she placed the thong in a paper bag with the shop's logo and handed it to him.

"It's for me," said Kit, just loudly enough for Nova, Mia and Serenity to hear. "I'm an ass-licking pantyboy."

The woman's smile thinned slightly, and she looked at the trio standing behind him. "Okay," she said. "Out! Now! Or I'll call security."

Nova nodded, Mia curtseyed, and Serenity hurried towards the door. Kit was about to do the same when the clerk grabbed him by the arm and said, "Not you."

"What?"

The saleslady waited until Mia, Nova and Serenity were all standing outside before pressing a button that closed and locked the door. Another button changed the sign on the door from 'OPEN' to 'BACK IN TEN MINUTES'. "Time for my coffee break," she said. "Follow me."

"What?" Kit stared at her. Quite apart from the weird feeling that he'd walked into a porn movie scenario, he'd never been good at estimating the age of Asian women, and this one might have been anywhere from eighteen to her thirties, maybe older.

"You think I don't know where you're from?" she scoffed "Or that you're the first sissy the Pridemore girls have brought in here and set up? Are you going to come with me, or do I call security on the lot of you?"

"Uhh..."

The woman grabbed a suction vibe from a display behind the counter, then led the way into a small alcove with a coffee machine, fridge, microwave, sink and bench. She closed the door before reaching under her skirt and removing her tiny black silk bikini briefs, then flipped up her skirt and bent over the bench, switching the vibrator on. "My husband never rims me," she said. "I'm lucky if he even goes down on me more than once a month, and he's not that good at it. You'd better not be kidding about being an ass-licker, pantyboy, because I'm not kidding about calling security."

Kit stared at her ass as she touched the vibe to her clit. She was in good shape, whatever her age, and when he parted her firm ivory cheeks, her tiny brown asshole seemed to be staring back at him impatiently. He kissed both cheeks before planting a kiss on the folds around her puckered hole.

"You can do better than that," the woman said, switching the vibe to the next level as she reached back and grabbed the back of Kit's head, pushing his face deeper into her ass. "Lick it like you love it! Or do you need me to sit on your face?"

Kit gave her asshole a tentative lick. It tasted fairly clean, better than he'd expected this late in the morning, and he twirled his tongue around her folds as she giggled appreciatively. After listening to her giggles become gasps and then purring with pleasure, he had to admit to himself that he did love it -- not her ass in particular, but that he was pleasing a woman by giving her what she wanted, even though they didn't know each other's names. It was thrilling knowing that women were willing to show him the most secret part of themselves and let him in, even if it was only with his tongue. He licked with more enthusiasm, and when her sphincter dilated in response to his ministrations, he gently pushed the tip of his tongue inside.

"oooooh yeah," she moaned, and then her sphincter tightened around his probing tongue as she came. She remained bent over the bench, not releasing her grip on Kit's head until she'd stopped shaking, then switched the vibrator off and straightened up, pushing him away from her. "Well, that was more fun than my usual coffee break. You must practice a lot."

"At least once a week," Kit muttered. He looked at her expression, and judged that it was safe to stand up.

"What do they call you? Apart from 'ass-licker' or 'pantyboy'?"

"Kit."

"I'm Linh," she said, stepping back into her panties and straightening her clothing until she looked businesslike again. "I'm only here on weekends -- don't try that shit on my boss, the woman who works here any other day. She's not into boys, even if they're wearing dresses."

"Understood. Look, I can do more than --"

Linh snorted. "You're asking for a job, Kitty-cat? Sorry, we're not hiring. Or if you're talking about fucking, forget it." She waved at the door to the shop and followed him out. Serenity, Mia and Nova were visible outside the shop window, and Linh pressed the button unlocking the door. "Don't forget your thong," she said, picking up the paper bag.

"Thanks."

"That cherry blossom shade doesn't really suit you, though. If I were you, I'd either go with something more flamboyant, like a hot pink, or stick with goth black."

"It's not for me. I mean, I'm not the one who's going to be wearing it."

Linh glanced at the women waiting outside, and shrugged slightly. "Uh-huh. Well, if I ever see you and your girlfriends in here again, you'd better either be buying more than one pair of panties --"

"- okay --"

"- or on your knees begging to kiss my ass."

Kit drew a deep breath. "Understood."

"Now get out."

"Yes, ma'am." He hurriedly obeyed, the bag holding the g-string in his hand, and blushed as Mia and Nova laughed at him.

"Okay," Kit said, handing the bag to Serenity. "I did what you asked, so remember what you promised --"

"Oh, I do," said Nova. "The Dragon Lady's not going to let us back in there, but there's a changing booth in Dollar Domain."

"What? You mean, now?"

"Sure. Of course, it'll mean walking around with your panties full of yummy cummies until you catch the bus home, but that's a small price to pay, right?"

"What? No!"

"What's the matter?" asked Nova, her tone teasing. "We can all tell how horny you are right now. Do you really want to wait until tomorrow night?"

Kit stared at her, then at Mia, then at Serenity. "This wasn't part of the deal!"

"I am altering the deal," Nova intoned. "Pray I do not alter it any further."

"Give poor Kitty a break," said Mia. "You gave her your word. You can agree on a time and place when we get home. Kitty, if you're desperate, I hear there's a glory hole in the men's room of the gay bar over on Church Street." She pointed in the general director of Pridemore. "And it won't set off your ankle monitor."

"That wasn't what --," Kit began, then shook his head. "No thanks." He looked at Nova and said, as assertively as he could, "Not tomorrow. If you're in that much of a hurry, make it tonight, in the dorm, before lights out."

They stared at each other, neither willing to flinch, until Mia said, "Let's make this fair. One of you can pick the time, the other picks the place."

Kit thought quickly. He suspected that if he let Mia pick the time, she'd postpone it indefinitely. "Next Thursday night."

Nova looked at Mia, then at Serenity, then back at Kit. "The laundry room."

"Deal," Kit replied.

"Good," said Mia. "Shake on it, and we'll go get lunch. Assuming you're hungry again already, Kitty?"

(To be continued)