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

All characters are 18 or over. Comments welcome.

Serving Time

by Kris Cherita

Chapter 11

"Do you want to make cummies tonight?"

Kit closed the dorm door behind him. It was a Sunday, traditionally masturbation night, and nearly time for lights out: Amber was already in bed, and Serenity was standing with her back to him, wearing a black t-shirt and pastel pink bikini briefs. Before he could answer, she turned around, and he saw the big bulges in the front of her shirt (obviously one of Mia's: the slogan read 'Make America Goth Again'). He stared, and Serenity giggled. "You look so cute in that dress," she said.

Amber peered over her reader to look at him in his hired French maid costume, and smiled. "A bit too femme for my taste," she said, "but definitely an improvement."

"Thanks," Kit muttered as Serenity pulled the t-shirt up over her head, revealing one of Mia's lacy black plunge bralets stuffed with the DD-cup breast forms that Kit had worn the night before. She looked down at them, and shimmied to make them wobble.

"I always wondered what it'd feel like to have big boobs," she said, a little wistfully, as she ran her fingers around the bubblegum-pink silicon nipples. "I thought I'd try these before Hailey takes them back on Tuesday. Do you like them?"

"They look a lot better on you than they did on me," Kit replied, "but you don't need them."

"I know, but... you didn't answer my question."

"What question?"

"Do you want to make cummies tonight?" Amber repeated for her. "It's Sunday, after all."

"Well, yeah..." It had been more than two hours since he'd jerked off into one of Stacy's bras in the laundry room, and he could feel his cock stiffening in his panties as Serenity fondled her fake boobs. "Do you want me to go down on you?"

"Sure," she said -- then, as he reached for his zip, she added, "No, don't get undressed. I like the idea of having a maid service me."

Kit didn't reply.

"You think it's only men who ever fantasize about that?" she asked. "I'll make you a deal. If you make me come once while wearing the dress, before the lights go out, I'll... I'll let you fuck these nice big titties. Your choice."

Kit blinked, and Serenity giggled again. "Come on," she said. "We all know you get off fantasizing about fucking Stacy's tits, and River's, and probably Mia's and Maggie's and June's and Danning's --"

"Not Danning's," he protested as the door opened behind him and Nova walked in. "She's probably got a bear trap down there. Like in that cartoon movie."

"Jessica Rabbit," said Amber dreamily. "I always wondered whether she swings both ways. Did you ever see that short cartoon where she's dressed like a park ranger? A lot hotter than that pink dress."

"Many times," said Nova, patting Kit on the butt, "but she's probably too old for you."

"Cartoons don't age. And a girl can dream, can't she?"

"'The stuff that dreams are made of'," said Nova. "Can you move your cute little tush, Kitty? It's late, I've cleaned my teeth, and I want to get ready for bed. You should, too."

Serenity shook her head. "What's it going to be then, eh?"

Kit hesitated. "What if you don't come before the lights go out?"

"Well... if I'm close I'll let you keep going until I do, and if not, I'll go back to my bunk and use my vibrator and you can make cummies in your panties. Do we have a deal?"

Kit nodded, and Serenity peeled off her bikini briefs and tucked them under Kit's pillow, then sat on his bunk with her legs spread wide as the bell rang, signalling ten minutes to lights out. She beckoned to him, and he knelt between her thighs and began kissing her cunt. She was soon wet enough for him to tease her labia apart with his tongue, wet enough to slowly insert a finger into her depths and seek out her g-spot while his tongue spiralled towards her clit. A bell sounded, signalling five more minutes before lights out, but Kit knew better to hurry; he concentrated on Serenity's reactions, listening to her breathing, feeling her cunt began to tighten around his finger as he licked her. She began to gasp and writhe a few minutes later, and he gently sucked her big clit out of its hood until she came, flailing and wailing and drumming her fists on his bed as she blessed it with her juices.

"Wow!" said Amber softly. "I'm not into femmes, but even I found that hot. Do we really have to return the dress?"

"Talk to Mia," Nova suggested. "She paid for it."

"Okay," said Serenity. "Your turn. You can take the dress off -- unless you'd rather leave it on?"

Kit quickly stripped out of his dress, and the lights went out while he was pulling his panties down. "How do you want to do it?" Serenity asked. "You sitting up with me between your legs seems most comfortable for both of us."

"Okay." He grabbed the bedpost and hauled himself up onto his bunk. When she felt him sit beside her, she grabbed his pillow to kneel on, and groped along his thighs until she found his erection. "Ooh, you're already hard," she crooned. "You like licking my cunt that much?"

"Maybe it was wearing the dress," said Amber. "Being your sissy maid."

"I like making you come," Kit replied, trying not to grit his teeth.

"Let's see if I can return the favour," said Serenity cheerfully. She rubbed her hands over her cunt to wet them, then spat into her hands and used the fluids to lube up his cock. She touched the head with her thumb and found a drop of pre-come, which she added to the mix. "Do you want to grab my boobs, or should I do it? They're nice and squishy, like the real thing." As her eyes adjusted to the near-darkness, she grabbed his hands and placed them on the sides of the silicon breast forms, squeezing them together. She'd kept the bralet to keep the fake boobs on rather than risk having the adhesive fail while she tittyfucked him, but his cock stiffened even more when she sandwiched it between them. "You can be in control, set the pace, if you like. I haven't exactly done this before," she confessed quietly.

"Nothing to it," said Nova, in the bunk above them. "Just rub 'em up and down, like they do in porn. And if you like, you can kiss or lick Kitty's clitty while it's between your titties."

Kit peered into the darkness, wishing he could see what was happening, then tried concentrating on the feeling of the slick silicon enveloping his cock, then tried imagining that he was fucking a real pair of tits -- Stacy's, or River's, or Mia's. After a few minutes, he felt his erection start to soften, and quietly asked, "Is this position good for you?"

"Well, I'm humping your pillow, but it's not like I can feel your cock," she said. She bent her head and stuck out her tongue, licking another drop of pre-come from the tip.

"What if you lay on top of me, like we were sixty-nining?"

"We can try that, sure." She climbed up onto the bunk and handed him the pillow before stretching out on top of him. She spat on her hands again to lube up his cock before sandwiching it between the silicon tits. Though she was nearly as tall as he was, this meant that he had to grab her hips and lean forward to be able to reach her clit with his tongue. Serenity continued rubbing the breast forms up and down his cock, but he buried his face in her cunt and kissed and sucked her clit so that she came before he did. She collapsed on top of him, lying there until she'd stopped shaking with the force of her orgasm, then asked, "Is this working for you, Kitty?"

"Not really," Kit admitted. "I mean, they're not real, they're not part of you, they're just... I don't know, toys."

"What's wrong with toys?" asked Amber.

Kit ignored her. "Are you enjoying it?"

"I enjoyed you going down on me," Serenity replied, "but this..."

"Titty-fucking's mainly a visual thing, anyway," said Nova. "Eye contact helps. And spit's not a good enough lube."

"What do you want to do?" asked Serenity.

"I'd really like to fuck you," Kit replied, "but I guess that's not going to happen."

"Not here, and not without a condom and some lube. And that's whether you mean my cooch or my ass." She was silent for a moment. "Have you ever heard of hot dogging?"

"Is that like rawdogging?"

"No. It's like tit fucking, but it's being sandwiched between the butt cheeks instead of the boobs. But I'd want to be sure you weren't going to stick it in my asshole, so I'd have to be wearing a thong. We can do that sometime, if you'd like."

"Hell yeah!"

"But not tonight. And you'd have to make me come first."

"But..."

"You want to make cummies now?"

"Yes, if..." Kit drew a deep breath. "Look, I wore the maid costume, I made you come twice --"

"Aw, poor Kitty," Nova drawled. "Oh, come on, admit it, you liked it, didn't you? There's no crime in giving yourself over to pleasure."

"Guess you'll just have to jill yourself off in your panties again," said Amber.

Serenity rolled off him and removed her bralet and the breast forms, which she carefully placed on the floor, then turned around so that she could murmur in his ear, "Or I can do it for you, if you prefer, while you fantasize about fucking Stacy's tits... or her ass."

"Or yours."

She felt his cock stiffen. "Maybe one day, after we get out of here. Your cock feels like it's the perfect size for my asshole, long enough but not too fat, not if you use enough lube. Of course, I'd want you to get me ready, first. Go down on me, make me come a few times, then while you're licking my clit, you can start fingering my asshole. Just the outside, get it nice and relaxed, maybe stick your finger in just a little but not too far, not without some lube, pussy juice won't be enough, my asshole is so tight than even licking it won't be enough to get it to open enough to take your cock all the way inside, no matter how long you lick it, but of course I'd love you to lick it for as long as you like while I lube up your cock, maybe I'll go down on you first as long as you don't come in my mouth, that would be a waste when we both want you to fuck my ass instead, so you'd have to put lube on your fingers and rub it in, get your fingers inside me, feel how hot and tight I am, imagine how good it would feel to have that hotness and tightness gripping your cock while you slowly slide inside me until you're all the way in, and then fuck my ass, fill it with cock and then fill it with come... ooh, yeah, like that," she said, as he ejaculated into his panties. "So much come! Just like that."

She kissed him on the cheek. "If you come to the mall on Saturday, we can go and buy me a nice thong or a g-string, a nice pretty one for when you hotdog my buns. I'll even let you choose the color." She hugged him, and they lay in the narrow bunk together for a few minutes, then she kissed him on the mouth, tasting her cunt juice on his lips and tongue. "Good night, Kitty. You looked really cute in that dress, and I loved having a sissy maid. Maybe we can do it again some night. Sweet dreams."

(to be continued)