A Sissy Goes To Jail (Gay SPH)

By akinkyboydreams.

It seemed like a great idea. The night, an empty subway station and a camera to take hundreds of photographs and videos of Candy. Adventurous content that, of course, Katy would be in charge of.

Dressed in a sexy PVC maid’s dress, Candy posed sensually and allowed the camera to create content he would undoubtedly show off on internet platforms. He was an OnlyFans star, after all, and he loved it. He never felt as comfortable as he was in his sissy persona, wild and free, free to do whatever he wanted to and show his true self to those who paid to see him.

The camera didn’t stop. Candy looked seductively into the lens as he took off his clothes. The dress ended up on the station floor, just like the lacy bra and little pink panties he was wearing, and then there was only him, dressed in high heels, stockings, and a metal chastity cage around his short, slender dick.

He felt more fun than ever, sexy, as Katy praised him and instructed him how to pose. Just the two of them, no one else there. What could go wrong?

Well, everything.

When he least expected it, the beams of flashlights fell on them, and the sound of male voices and hurried footsteps was heard through the dark place. And then: “Police! Stay where you are! Down on the ground.”

The bellow made Finn come back from his moment as Candy, and not knowing what to do, looking for Katy only to realize that the girl had escaped. Just like that, she was nowhere to be found without saying anything. And he was still there, alone, trapped, and with his nakedness humiliatingly exposed before three police officers.

Thirty minutes later, he found himself held handcuffed inside a prison cell. Scared, confused, intimidated, and wishing he had someone come get him out. Little did he know the adventure was starting.


He had been inside that prison for more days than he thought. It was a dirty place, overcrowded with strong, sometimes violent men accustomed to living in these confined conditions. Worst, or best of all, he was enjoying it! In very little time, he had become everybody’s favorite prison bitch.

From the midnight blowjobs that he was forced to give to other inmates to being gang-raped daily in the showers when no guard seemed to pay attention. He had to admit that he had found an inexplicable delight in being used to arouse the pleasure of other men, those who were lost in the warmth of his smooth thighs and his tight asshole. They were primarily strong, threatening-looking men, and although anyone would be scared to get hurt by them, Finn loved that they wanted to use him.

There wasn’t a day that went by that there wasn’t a cock finding its way into him as he was rammed violently against the wall. It turned him on so much he loved receiving commands in his ear that it made him get hard, as hard as he had ever thought possible, even for his small dick.

Katy had also found a way to play with him and his mind forever. He opened up with her about his preferences and wished to be subdued by her. She had not stopped flitting around his mind with her dirty demands. She wanted more, needed more, of that thing that made her feel so alive, so damn good. She would humiliate Finn, have all the power and control over him, and see how even after all that, he was still willing to do anything for her.

That afternoon, Finn was ushered into the conjugal visiting room, where the purple-haired girl sat waiting for him in the plastic chair, wearing a tight latex dress the same shade as her bubblegum-colored locks.

It had only been enough to see her for him to enter the role, falling on his knees when her index finger had indicated it, kissing the tip of her high-heeled shoes.

“Did you miss me, whore?” she asked, making him moan softly at the anticipation. “I know you did. I bet you’ve been waiting for this moment all week, haven’t you?”

Her teasing smile caught him off guard, making his cheeks burn. He licked his lips.

“What? All of a sudden, you don’t know how to speak? Answer what I asked you!” she demanded, grabbing his chin to force him to look at her.

His voice was shaky when he replied, “Yes.”

“Yes, what?”

His legs were shaking, and his hands itched with ill-restrained desire. He wanted to touch her, run his tongue over the silky skin of her legs and the small perky breasts peeking out from the neckline of her dress, and suck the small nipples pressing against the purple latex.

“Yes, I missed you.”

Katy rewarded him with a deep wet kiss, slipping her tongue between his lips, completely plundering his mouth most exquisitely.

“Good little bitch” she smiled, with that impudent smile she always brought with her, pointing to the chair where he should sit. “Look at you in those prison clothes! It’s so hot seeing you like this. Orange suits you!”

He felt his stiff dick push against his orange prison pants and pink underwear, which he began to display to her. He didn’t know what Katy had in mind for the day, but he desperately needed to find a way to ease the pain in his balls. He needed a release of his own.

“Oh, and pink panties too! They do look after you around here. I bet the other men have boring white pants that show off their nice big cocks! I’m impressed you got those sexy satin ones to wear! Now take them off.”

The blow of a whip hit him directly on the right thigh, making him scream like the sissy he was at that moment.

“I didn’t say you could touch yourself, did I?”

He shook my head, shifting in place, kneeling in front of her, noticing the presence of one of the guards. It was Jack, though most knew him as Officer Hunter. The one who broke into his cell last night and made Finn service him.

The tight hole between his ass cheeks puckered, remembering the feeling of his hot, thick, and veiny cock trying to make its way inside him, the saliva falling from his lips straight to his fat head to lubricate a little and with it, forcing Finn’s body to take it.

The anticipation was killing him.

Katy’s smile widened. She seemed to know exactly what happened between that guard and her husband. Finn could see the ideas forming in her mind just by how she looked at the dark-haired man.

She stood up and took a couple of steps, her heels clicking over the floor severely as she came to stand before him. He kept his eyes on the floor, just like he’s been taught, his teeth buried in his bottom lip as he breathed deep and controlled through his nose. She trailed her eyes over the quivering muscles of his stomach and lowered to his cock. He was hard, blood rushing in his veins as he waited for whatever plan she had in mind.

Finn was a dream, and he was all hers. Always as innocent and cute as no one else could be. No one had ever stirred her passions that way, made her feel all those things, and made her feel so powerful. The way he responded to her every touch, the way he obeyed her, and God, the way he let her do whatever he wanted. It was sublime. He took every bit of violence she dealt him, absorbed it, and returned it all as devotion. She would use that in her favor to turn him into her pet, her toy, her perfect sissy husband.

“Finn, we’re going to play a little game today,” she announced, her voice playful. “And you will do whatever I say,” she said, and it was a little affectionate, a little angry. “Unless… you want me to get angry.”

“No, my queen.”

“Good.” She used the tip of one manicured nail to tip his head up so she could look better into his eyes. “You already know why he’s here, don’t you? He’s going to give us both a good time.”

She could do anything to him right now and loved him for it.

The guard draped himself across Katy’s back and scattered the dark direction of her thoughts, looping his arms around her shoulders so he could fondle her breasts. His breath caressed her skin.

“Already horny for me, little one? Such a naughty wife when your excuse for a man is under my supervision!”

Katy shrugged, bringing her hands up to cup his forearms where they were laced loosely around her neck. “You like girls like me who cause their sissy boys to be locked up here, I know. I planned this. Who do you think tipped off the cops?”

Katy slid her delicious ass over the table, pulling her dress up until it hung on her hips, revealing that she wasn’t wearing any panties. Damn, she was so wet.

Her breath quickened as she showed the wetness of her pussy to the guard and, at the same time, to Finn since it was inches from his face. The scent immediately drew him in and made him slide his tongue over his lips.

“I want to fuck that tight pussy,” the guard murmured, holding his hard cock with his left hand, showing that he had been turned on by seeing Finn half-naked, willing, humiliated, and eager.

Katy looked at her boy, assessing his reactions, she knew him well, and he wanted all of that. Finn had avoided telling her that he had picked fights inside the prison during breaks in the yard, only to extend his sentence. She still knew he enjoyed his time there.

“And you will, but it will be after Finn gives you a blowjob, hmmm?” she asked, but both men knew that she was not asking for permission. It was an explicit order.

Finn nodded obediently, allowing the guard to stand in front of them.

Seconds later, he had the tall man in front of him, unzipping his pants, leaving his thick cock in front of him, and slapping it against his cheeks. Katy shifted so she could look over Jack’s shoulder at the scene, grinning from ear to ear; Finn knew that she took pleasure in taking control of everything, even the people around her outside of the sexual realm. And to be fair, Finn enjoyed it. That look on her face and excitement showed as she leaned against Jack’s shoulder.

“Open your mouth, slut,” said the guard while Katy guided his fat cock between Finn’s lips.

“More, Finn, open your mouth wider. We both know you can take it.”

The boy forced his mouth to open wider, just the same way it did last night. Jack’s eyes rolled back, and he slowly pushed into his mouth. Finn could feel the salty taste brushing against his salivary glands, the drops of pre-cum sliding down his throat.

It was too humiliating, too degrading. And… he had to admit, it was exciting.

He liked it. Katy knew it, her eyes were shining, and she had a big smile as she whispered things in Jack’s ear. Finn used his hands to hold onto the guard’s muscular thighs, settling a rhythm, bobbing his head up and down, only stopping occasionally to lick the entire length. His tongue ran over the hot skin, drenching the hard cock with hot saliva; he then licked a way up to Jack’s balls and kissed, sucked, and licked. He put them in his mouth to massage them with his lips.

Jack began to push his hips up, his hot, veiny cock fucking Finn’s mouth. He held a grip on his hair so the boy wouldn’t stop sucking. “Come on, take it faster, like last night.”

The boy felt a burning in his gut. His hips moved on their own, seeking friction against whatever was within reach.

Katy said, “Are you horny, my bitch? I can see your little dick. It’s very hard. Do you want to fuck me, or do you want him to fuck you?”

Just listening to her made Finn feel so close to cumming. He couldn’t even formulate an answer. Her words were quickly taking him to climax, although he couldn’t cum. His muscles clenched, and he decided to lick Jack’s balls again, making him groan. He was so horny; he could be begging right now.

“Answer me, Finn!” she demanded, and Jack pulled his dick out of his reach.

“I want him to fuck me!” Finn said desperately in response and then heard their cheeky laughter. “I want–”

“A pity that the one who gives orders is me and not you,” she cut him off, pointing to the chair she had been sitting on. “Sit there. You’ll see what a real man can do.”

Finn gritted his teeth, feeling dissatisfied, but the scene made him too horny. He then moved towards the seat, trying as hard as he could not start playing with his cock so he could cum.

Katy made the guard turn around, cradling him between her thighs. Jack pushed the tip of his big cock against her wet pussy repeatedly, rubbing her clit vigorously each time, making her moan loudly and arch her back.

“If you cum, you will pay dearly. You are only here to watch. If you touch yourself, I will know, and then I will ask Jack to send you to the cell alone. Are we clear?” she said in a bossy tone. There was a crazed glint flashing through her eyes.

Finn nodded, placing his hands on the chair’s armrests to hold something.

Jack rubbed his cock against Katy’s pussy lips again, making her gasp with pleasure. Finn let out his own little pleasured moan.

“Do you get this hard because you know Finn is watching us or because you like my wet pussy?” Katy ran her nose through the guard’s neck as she spoke, “Are you going to leave my pussy looking so red and sore? Well, used pussy is my favorite color, after all.” She ran her tongue over his earlobe while looking at Finn.

“You’re so wet,” Jack spoke, running his fingers between her lips, caressing her pussy and clit. “You’re delicious. I wish all the inmates had wives like you!”

Finn’s eyes remained attentive to the act that was taking place in front of him. His hips thrust in time with the guards as he pushed, and when he finally slid inside her pussy, the boy couldn’t help but moan.

“Oh, Jack, your dick is so big. It fills my pussy so well, not like my hubby’s!” Katy murmured, and Jack let out a groan.

He was fucking her real hard. Her body bounced over the table with every thrust of his dick, making her moan and sink her nails into his arms around her waist, calling his name as she kept telling him she was about to cum. Jack held her firmly and took another position, sitting on the table and his lap, her back against his chest.

“Baby, come here,” she called Finn. She was facing him.

Soon he was crawling toward her like a little lost puppy. So dependent on her, to any outsider, it would be pretty pathetic, but to them, it was a sweet combination of love and lust. He let her get her hands on his hair and pulled him until his face was near her pussy, his head right between her thighs.

“Make me come,” she whispered, trying to drown her moans. It was an order, but her voice was so soft at the moment. It’d be cute if not for the sadist, evil smile she had on her face as she looked down at him. He didn’t pay much attention. He was focused on Jack, still fucking her, pushing his dick faster into her. His dick is so big, fucking her in the way he fucked him last night.

And there it was. Her sweet, exposed little pussy, all for him. She was dripping wet. Her clit blushed hard. He could smell her arousal; she smelled so damn good. It was intoxicating. He bent down a little more to her, and his tongue lashed her clit, remembering and repeating the same movements he had done the last time he tasted her. Damn, she tasted sweet, tart, and savory.

“Finn… god, you are good with your tongue! This is so much better than when I used to let you fuck me!!!”

Her orgasm was powerful, caused by the big cock filling her pussy and the mouth eating her so well.

Climax gnawed into her composure with sharp teeth and began to unravel her. She felt so complete at that moment, so powerful, with all the control in the world just as she liked.

Then, her husband’s tongue flirted with the ultrasensitive tip of her clit. Jack fucked her faster and deeper, his dick filling her hard, hitting the spot inside her that made her scream.

“J-Jack! Fuck. Yes, yes, Jack! I’m coming!”

Her back arched as she panted. The climax was big, huge. She squirted hot wet nectar all over Finn’s face as Jack filled her with his cum deep inside. Finn could never explain why, if being a cuckold was so humiliating, it still turned him on too much to the point that he felt aroused and about to cum just as he watched another man fucking his wife. She called another man’s name when she reached her orgasm. Not his, but Jack’s. And he still loved it.

“Touch him, Jack. Make him cum for me.”

Finn’s chest rumbled, and their legs faltered as he felt the guard press himself against his leaning body, seeking to insert his cock between Finn’s buttocks to prolong his pleasure, as he used just two fingers to jerk that little boyclit off.

The act was dirty, sinful, and otherwise decadent.

“Come on, inmate, cum” Jack murmured, stroking his little cock.

Finn felt like he would explode in such a big orgasm as he tasted her pussy. He could feel Jack’s cum flooding out of that wet cunt. He could taste it on his tongue. So damn good.

“Yeah, like that, almost there,” Katy muttered, pinching her pink nipples between her fingers.

Her urgency made Finn increase the pressure of his tongue and push his fingers into her tight hole until she was cumming again, a victim of a second orgasm and her insatiable thirst to humiliate him.

It didn’t take much longer until Finn felt a shiver that finally destroyed him, sending him over the edge. He bucked his hips, pushing his small dick as Jack squeezed it. There was a groan, and a sputtering sound as waves of semen began to erupt directly into Jack’s hand as Jack unloaded into his sissy asshole.

“Feed him,” Katy instructed.

The officer cupped his hand and encouraged Finn to lick every drop. Meanwhile, Jack’s cum proceeded to leak from his butt. Once Jack’s hand was clean, Finn proactively licked up the cum spilled onto the dirty floor. Such a model prisoner.

He was fucking loving this. A cuckolded husband kept as the prison bitch to boot. He needed his wife to visit more, be fucked every night, and be cuckolded because he genuinely loved it! And he would do whatever he needed to stay in that prison longer.

In a few moments, visiting time would be over. Officer Hunter would lead him back to his cell, still leaking cum. Meanwhile, Katy would be collecting the CCTV footage of her cuck’s various cases of abuse in the showers as a souvenir of her visit for the occasional night she chose not to take in a lover. That really wouldn’t be all too often.


The End.


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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