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 12

Monday was laundry night for River's dorm, and the thought of having another chance to fuck one of Stacy's bras while fantasizing about her tits kept Kit horny and distracted throughout his classes, even though he'd come twice the night before. At dinnertime, he was relieved that his baggy pink scrubs hid his erection, and he made only a weak token protest when Mia and Nova insisted he change into the French maid's dress again now that Danning had left for the night. "Suits you," said Mia as he finished dressing, having been careful to keep his back to them as he stripped.

"Pity it's not pink," said Nova.

The goth shook her head. "Black's hotter. And it goes with everything."

"Maybe we should ask Kitty what she thinks," said Nova. She slipped her hand up under Kit's skirt and grabbed his erection. "Ooh, I think she likes being our maid. Kitty's pretty itty bitty clitty's all stiff and swollen. What can she be thinking about?"

Kit drew a deep breath. "Walking in on the two of you sixty-nining, and buttfucking whoever's on top," he replied.

"Dream on," said Nova, not unkindly. "But I might let you rim me one night, if you're very good. Ooh, you like that idea, too."

"Better stop," said Mia. "We don't want any accidents. Have fun doing the laundry, Kitty."

*

Kit had loaded the sheets into the washing machine, which was noisy enough that he didn't hear the door open. He had searched through the stack of clothing for one of Stacy's huge black bras and had just grabbed one when he felt someone lift up his short skirt and pull his pink panties halfway down his thighs. He turned around, expecting to see Nova or maybe Serenity, but the woman dropped out of sight, falling to her knees behind him so that her face was level with his ass. "What are --"

"Shh," said River, and kissed one of his butt cheeks. "Do you want anyone to come in and see you like this?"

"Like --"

"You were going to jerk off into Stacy's bra again, weren't you?"

"I --" Kit drew a deep breath, "Well, you never wear one."

"Nice save," River replied, and kissed his other cheek, then grabbed them and spread them.

Kit was torn between asking "What are you doing?" and "Did she notice?", but he swallowed and said, "Does Stacy think I --"

"Oh, I'm sure she suspects it, and but you did a good enough job of cleaning up afterwards that it passed the sniff test, so you've gotten away with it. Besides, I bet she's had come on her boobs before now."

"Uh-huh -- AAH!" He felt the tip of her tongue slide down his butt crack and lightly touch his asshole.

"Did you like that?"

"Yeah, sure, but --"

"I know I should've asked first, but you look so cute in that dress and I wanted to surprise you and I didn't think you'd mind." She flicked her tongue around his asshole again. "Or do you think having a woman lick your ass makes you gay?"

Kit snorted. "If I believed those incels on MRATV who think that having any sex that won't get a woman pregnant means you're gay, I wouldn't be playing volleyball with you all every week and eating you out, would I?"

"That's truer than you realize," said River, taking another lick. "If you fell for that crap, Danning would've known there probably wasn't much hope of reforming you and sent you straight to jail. But I'm glad you're cool with this. I wanted to show you how good it felt to be on the receiving end of a good rimjob rather than giving one." Another lick, this one swirling slowly around the folds of his asshole.

"You mean I'm actually good at --"

"You're pretty good," she replied. "I've had better, mostly from women, but you're learning and you remember what you've learned. And you don't treat it like something you have to do to persuade a woman to fuck you, you don't act like you're bored or impatient --"

"How could I get bored of helping women come? Especially women as hot as you?"

"You'd be amazed how many men do. But I can't rim you and talk at the same time, so which would you prefer?"

"Well, we can talk almost any time... but I haven't showered or anything. Is that okay?"

"You're clean enough, so you taste okay. And you're not hairy, which is good, because hairy butts are harder to keep clean. Yours is as smooth and pretty as a girl's, which is the way I like them."

"Thanks... I think."

"If you want to get your ass licked more often, you should probably keep using nanogel, especially in your crack. And maybe try some perfume -- something subtle, not too girly, but not one of those men's sprays that smell like a sports bar. A nice unisex cologne, maybe. I think Nova has some 4711."

"You're kidding, right?"

"It was issued to U-boat crews, so why not? And do you think girls don't perfume their cunts and their assholes before they go on a date?"

"I wouldn't know. I've never really dated one. Do you?"

"Date girls? I thought you knew that."

"I mean..."

"No, but I'm not into planning ahead. I prefer spontaneity. Like this." She slid the flat of her wet tongue over his asshole as though licking a lollipop.

"Yes."

"Yes what?"

"Yes, I like that. Or, yes, please."

River grinned, and held his cheeks apart to give herself easier access to his asshole. "Tell me what feels best while you jerk off into Stacy's bra," she said, as she peeled her tie-dyed t-shirt up over her head and rubbed her beautiful big breasts over his butt cheeks while untying his apron strings.

"Oh, that feels great!" he moaned as she kissed her way down his spine to his hips, then ran the tip of her tongue down his crack and gently probed his asshole while he whimpered in pleasure. He could feel her hard nipples grazing the backs of his thighs as she planted quick kisses around his asshole, then running the tip of her tongue lightly around the folds.

"That's fantastic! Yeah! That's the best."

She circled his asshole, then the circles became a spiral until her tongue tip was softly probing the tight little opening before spiralling out again. "What are you fantasizing about?" she asked, briefly removing her face from his crack and rubbing her breasts over his smooth cheeks.

"That there are two of you," he said thickly. "One of you doing what you're doing, and the other one is titfucking me and sucking my cock. Hey, you asked."

"I wouldn't have asked if I didn't want to know. My tits, not Stacy's?"

"Hers are so big I could get lost in there. Of course, if they sent a rescue party after me, I'd hide from them. Unless it was you."

"Flatterer."

"It's the truth. And if there were three of you... but then I'd have to decide whether to suck your tits or lick your cunt or your asshole, so I'd have to let you choose."

She went back to licking him for another couple of minutes before asking, "I know you like my boobs, so you could start there, get me wet, then worship my cunt. Do you like that idea?"

"I love it."

"Good. Now that you know how good it feels to have your asshole licked, would you like me to finish you off with my hand?"

"Yes, please!"

River grinned, and spat into her hand to lube it up, then reached around and grabbed his cock. "Spread your cheeks so I can keep rimming you, and you can still come in Stacy's bra."

He obeyed, and she caressed his cock and balls until he realized he was rapidly approaching the point of no return. "Oh, that's fantastic," he moaned. "I think I'm about to --"

"Good. Remember this next time you're lucky enough to lick a woman's asshole."

Kit nodded. "I will. I'd still want to worship your tits and cunt, but any time you want your asshole licked, I will."

"Not just mine, I bet. Imagine if we were all lined up with our asses spread, Stacy and Mia and Nova and Freya and Sky and me, our wet cunts and hot little buttholes on display as we waited for you to lick us and tongue-fuck our butts --"

She flicked her tongue lightly over his sphincter with a little more pressure as he said "I'd do you first -- fuck!" and began ejaculating into Stacy's industrial strength bra. She continued licking for a few more seconds, then kissed his cheeks again and extricated herself from under his skirt.

"Well," she said, as she looked at the puddle of jizz in one of Stacy's F-cups, "that was worth wearing a dress for, wasn't it?"

"oh fuck yeah."

"I bet you'd wear a dress every day if you thought it turned us on and got you more rimjobs."

Kit nodded, realizing that this was true, and turned around to face her.

"Pity the outfit's going back tomorrow," said River, looking him up and down. "You look much better in a dress, and it's not only men who like the idea of having a maid who's also a sex toy."

"I can do your laundry without needing to wear a dress!"

"I know, and I'm happy for you to keep doing it, but make sure you wash Stacy's bra thoroughly. You don't want her pissed at you, especially now that she's cooking the meals." She kissed him on the forehead, picked her t-shirt up from the floor and put it on, and walked out.

Kit pulled his panties up over his cock as he watched her go. "Same time next week?" he said, hopefully.

River laughed. "Not unless you're wearing a skirt. Or... when's your birthday?"

"Next year."

"Hmm. Well, you'll just have to beat our team at volleyball again, won't you? Good night, Kitty."

"Good night," Kit replied, remembering her comment about the women in the school lining up and spreading their cheeks so he could rim them, knowing that he'd still be imagining that when he went to sleep that night.

(To be continued)