It was the boy's first night in prison. At a young age, he had gotten into the habit of stealing; particularly, he stole women's "personal" clothing, underwear, nightwear, and the like. The bars slammed shut, and he found himself in a remote cell, at the end of a block, looking out at nothing but a poorly lit brick wall. Inside the cell was something else entirely.
The boy knew the warden, personally, as he had pilfered from his beautiful young wife on more than one occasion. As it turns out, after one aborted attempt, he had also been stealing from the warden's mistress, whose clothing the young wife did find, left behind by his heist, and promptly filed for divorce. A judge bribe and a rigged jury later, and the boy found himself with three years to serve in the warden's prison for a felony "reckless endangerment" charge on top of burglary. Strangely, though the prison was an all-male prison, as they often are, the tag on the boy's uniform said "Kitty." And what a strange uniform it was. Kitty had always been feminine, soft-spoken, reclusive. People teased her for being short and forgettable. But the outfit was louder than life.
Far from being the usual grey-dismal slacks and sleeved-shirt ensemble, Kitty's dress was just that, lacy and black. From bottom to top: six-inch "fuck me" pumps (as the warden called them), with a small buckle clasp keeping them tight, black fishnet stockings coming up to the thigh, clasped with a garter, topped with white lace and ribbon. Underneath the frilly, poofy maid-like skirt (of course, likewise black with white lace) was what made "Kitty" most uncomfortable: a French-cut, again, black-with-white lace pair of panties, large, to fit Kitty's less than modest assets, which were prominently displayed by the skirt, which covered little. Above that, a white maid's blouse, froofy shoulders and a low-cut, revealing "breasts" that were mostly padding and a push-up bra. A collar, engraved with "Kitty" and a paw as well, that went around the neck and was buckled in the back, like a pet collar, and then, just above that, was the make-up fit for a high-class "escort," complete with pink lipstick, blush, rouge, eye-liner, eye-shadow, and a waxing. That wasn't the only place that Kitty had waxed and shaved of hair. The hair, however, was given the royal treatment, straightened and sprayed and cut medium-length, with heavily prominent bangs and straight, black, sleek hair that came down to the cheek. Staring in the mirror, holding a bouquet of roses, of all things, like the winner of a beauty pageant, Kitty found herself shaking with fear and ripe with bewilderment and surprise. Nobody would confuse "her" for a boy. That is, until they noticed the rather obvious bulge in the front of those panties. Then, certainly, they'd back down. Kitty knew that the things people say about prison are overblown and exaggerated to extreme degrees. Most guys are turned off by "that" kind of sex, Kitty told herself.
The warden liked what he saw. "Perfect," he said, earlier that day, "that collar might say Kitty, but that underwear says 'I don't bite.'"
Kitty stayed silent.
"Now, listen to me. You don't complain. You don't argue. Nobody is going to help you or change your predicament, and, least of all, punish me. I'm the law here. If you step out of line, it'll be worse. Much, much worse."
Kitty nodded, defeated.
"Good. Now, you'll talk like a lady, walk like a lady, and moan like a bitch in heat. Got it? Nobody'll have to wonder whether you're packing or not. In this prison, you're a girl, a slut who does it easy and likes it hard, understood?"
Kitty shook, and nodded. He was just trying to scare her.
"Enjoy your first night. Try to get some sleep before the morning," he said, amused.
And so Kitty marched down the cell block, guards in toe, amidst hoots and whistles and howls from the inmates, and sly looks from the guards. Her hips swayed side to side, which she could have stopped if she walked more awkwardly in the heels, but the warden had forbid it, and she didn't want the guards to anger. Kitty knew they were teasing. It was emasculating, and that was it. "Look at that guy wearing a maid costume," they'd say, and point and laugh. She could endure it.
But then the bars slammed shut, and she saw what the inside of the cell looked like. There was stone, and brick, and grey and dark, and then there was the bed-one bed, heart-shaped, pink, and laced, and much larger than the usual inmates twin-sized bunk. On the bed there were a few items: a card, sitting up on its halves, a bottle of brandy, a large jar of something or other, a few very obviously shaped object with flared ends, ring gag, a jar of extra-strong aspirin, a digital video camera, a pink cell phone, and a letter, also on pink, folded paper, sprawled out and filled with words.
She picked up the card and read it. The actual printed text just had a picture of two circles, one on each half, with a caption for each. The one on the left, a small circle the size of a dime, had the caption "how you are," and the one on the right, a half-dollar sized circle, read "how you will be (think about it)." The written text was addressed from the warden and read "Dear Kitty. Your cellmate is a man known for three things: the size of his frame, the size of his cock (he's got a foot-long! How about that?) and the size of his sexual appetite. He's been sequestered with you away from his usual store of a dozen or so of his usual targets, and he's been alone in that cell now for about two weeks. When he's finished, try not to lose control of your bowels, the janitors will have a fit if they have to clean that up. Do try to enjoy it; he's really good at it.
May you never be constipated again, Warden."
Kitty swallowed hard. She picked up the letter next, in what looked to be the form of a love letter, signed by Tyrone.
"Dear Kitty, the bitch with the fine heart-shaped ass, you are going to be walking funny for days, no doubt. If you don't want me to get too rough, just get up on our little love nest, shake your rear under that skirt and purr for me. I figure since your name is Kitty, and you're a bitch in heat, you can start off purring and end up barking. Try not to make too much noise, it's funny when you try to save face. Bite the pillow and grip the sheets, I'm going all in, bottom out. Try not to cum too fast, it's more fun if I have to work for it. You can call me master, or just grunt and moan, I don't care. When I put my hand up on your shoulders (that's my space now), give my fingers a kiss or I'll slap your ass raw, right? Don't feel too bad, bitches need it, and it sounds like you need it bad. When I tell everyone how I railed you deep all night, you'll feel proud. Which reminds me, try to hold in my load, I wanna see your face, because that is some hilarious shit.
Here it comes, slut, sincerely, Tyrone."
Kitty looked up to see that there was actually a dark man in the corner, who now walked out of the shadows, and revealed himself to be an elephant in the living room, well over six feet tall. He gestured at the bed, and Kitty froze. When he started to walk towards her, she climbed up on the bed and put on her best impression of a real, honest to god whore, complete with lip-smacking and purring, and even making a "kitty has claws" gesture with her hand, but all while wearing a wide-eyed, fearful expression. She shook her rear and waited, eagerly, as the massive man took hold of the jar and opened it, and undid his fly.
He climbed up on the bed behind Kitty, and pulled down the panties, and Kitty started to tear up. He took the open jar, reached his hand inside, and slathered Kitty's butt and thighs with the sticky substance, and even got some on Kitty's mound, and it dripped down onto her package. To her amazement, Kitty had gotten hard, fully erect, and wanted to touch herself, but the idea repulsed her. How could she sexually enjoy this man handling her so roughly, about to do what he was about to do?
He pressed his cock up to Kitty's balloon knot, and, suddenly, the card made sense. He had to be as thick as a half-dollar. Kitty wasn't small, but he was fiercely, terrifyingly larger. He called out, "here I go!" and, as if rehearsed, Kitty could hear the other inmates chanting "fuck Kitty's shitter, poor Kitty litter," over and over again. Some guys yelled out "how does it feel, Kitty?" as Tyrone pushed forward with tremendous strength, and Kitty clenched the sheets, gritted her teeth, and lost her breath, mouthing a nearly-voiceless "ahhhhhhhhh. nghhhhh.." as Tyrone pushed open her sphincter, and started to penetrate Kitty's virgin butt, stretching her colon to untold limits to accomadate his massive rod, making her sweat and shake and cry profusely, making a face in anger and sadness and shame. Tyrone had his massive hands on her girly asscheeks, and was pumping deeper into her shitpipe with his hips, penetrating more and more of her uncharted colon, emasculating her, humiliating her. The chants of "fuck Kitty's shitter, poor Kitty litter," are droned out by Kitty's own panting, grunting and moaning. She shakes her thighs and instinctively tries to pull away from him, and rips at the satin sheets, but Tyrone keeps his hands pulling back on her cheeks, which he strokes and swats at occasionally, and her hips, and, then, finally, her shoulders.
"You're not going anywhere, bitch. Grit those teeth, I'm gonna pump a foot of meat into your kitty, Kitty." Kitty does, indeed, grit her teeth, as he pulls back on her shoulders and thrusts, each thrust laying more and more pipe for him, opening, dilating Kitty's anal rings to a much wider, unnatural circumference, and opening Kitty up to a world of anal servitude and humiliating, a girly nightmare of "pleasing a man" with her waiting holes. She moans "oh my god, oh my god," a few times, but Tyrone seems to enjoy that, so she stops.
Kitty's clothing is becoming damp, and she's drooling, listless and devoid of fight in her, as she takes her "boyfriend" Tyrone from behind, pushing out so it doesn't hurt as much, but allowing her lover deeper and deeper into what should be her tight, boy ass. Tyrone takes a hand off her shoulder for a second, and then spanks her ass hard, so that she yelps out, followed by cheers from the other inmates, and Kitty feels her sphincter clamp down on him, making movement impossible. He uses his hand on her cheek, pulls it to the side so she loosens up a bit, and then thrusts in deeper.
"Almost there, Kitty," he says, and Kitty feels impaled, her ass on fire, her anal muscles in spasms, when, finally, she feels his hips on her ass, his balls on her little package, and she knows he's bottomed out. She scratches at the sheets, like a real cat, and he spanks her again. Her ass clamps down, squeezes him. She feels her own erection stirring. He spanks again, and a drip of precum trails down to the sheets. He starts to thrust in short thrusts, deep and heavy, and Kitty feels like her asspipe is widening more and more and more, and every time he spanks, she grabs onto him and she feels her cock jump.
"That's right, cum all over the sheets, bitch!" said Tyrone, spanking one last time, and thrusting a few times during the ensuing spasm, making Kitty explode all over the bed, squeezing Tyrone with her ass as much as she can against her will, moaning and cryind and whimpering as it shoots out of her while her boyfriend nails her ass, fucks her butt like that's what it's for, pounding her up the ass as punishment for her crimes.
- END Part 1