5/7 Prison Sissy Stories – PRISON SISSY CH. 01

Warning: This is a twisted and dark fantasy about a guy who was turned into a sissy in prison. It contains extreme ideals and is generally insensitive.

Please do not read if you are easily offended by black cock, black men, or gay sex. I warned you, so don’t waste your time. It is for a particular audience, so again, if that’s not you, no shame in turning back now. If it’s not your thing, well, you can’t say I didn’t warn you.

Sorry in advance for the grammar mistakes. I’m neither native nor the best at writing. Please give me constructive criticism if you have any, and I will learn from you. I’ll edit this story’s mistakes in a later version, so if anyone is interested in helping me, then knock me down. [Check out my profile]

All characters are 18 or older. Now enjoy.

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Following a bank heist, I was falsely accused of criminal activity and sentenced to 7 years in jail. According to my attorney, she may shorten it to three years if I do it appropriately. I was just a cashier. My lawyer bailed me out until I faced the trial and informed me of every possible outcome.

A couple of days later, I was taken to prison. The officer instructed me to strip naked after reading my file. I obeyed, laying down my pants and underpants. The officer then performed a thorough body search, and when he started performing the cavity search, my dick became rock hard.

I tried my hardest not to think about anything sexual since I was humiliated. However, he had two huge fingers firmly lodged in my asshole, so it was difficult to accomplish. I didn’t know why exactly, it just happened. I’d heard about cavity searches before, but he appeared to be taking his time on this occasion. He appeared to be digging into my ass with great depth.

“Is there any chance that you are bisexual or gay?” The officer asked. “You’re clean there.”

“It was my lawyer’s idea,” I replied politely.

“He’s clean; take him,” the officer said to the jail guard. “And you, calm your little buddy before going in there. There are plenty more people like me who like drilling deeper with big tools.”

The guard showed me the path and in every cell there I witnessed so many crazy things, just like I said before I came here. Finally, I got into my cell and it was two people’s cells. The guard locked the door and said good luck.

“It’s your first time, boi?” my cellmate asked me politely, but it still felt wrong.

“Yes, it is.” I looked at him and he was lying on the top bed.

“Then, you must have done your homework,” he said. “Tell me now how you intend to survive in this shithole.”

“My lawyer said, make some friends,” I replied nervously.

“Must be a good lawyer. So how many friends did you make after you came here?” he asked sarcastically.

“Including you, one.” I sounded pathetic.

“Hahaha,” he laughed out loud. Suddenly, a few inmates came in front of our cell and threatened me that they would make me their bitch, fuck my virgin ass, and use me like fleshlight. That was horrible. Fear drove me to the far end of the cell.

“They’re looking for food, boi,” he said with no emotion. “Are you food?”

“You’re my friend. You’re going to save me, don’t you?” I sounded like I was begging.

“My friends don’t need my protection, but my bitches do,” he replied with the same tone.

“What do your bitches do for you in exchange for your protection?” I asked her with a broken throat.

“Cut the shit out, boi. It’s my nap time,” he barked. “If you really want my protection, then show me your obedience. Massage my legs, thighs, and shoulders while I’m napping. And don’t speak until I start it.”

Then he stopped talking and I could hear his breath getting deeper. As he said, I did my homework. A boy like me in jail is just a nightmare. I don’t even know his name, but he seems nice. “Get on your knees,” I expected to hear from the first guy I met here. I read some articles about how to suck cock well and take those in the ass. And then I practiced with a big dildo at home. Better safe than sorry.

I climbed two steps up the ladder, and I was shocked. He was lying naked on his belly. I thought a little, then sat between his legs. The first thing I noticed was his soft cock. It was big, and I mean it.

He was lying with his legs apart, revealing a massive black cock and a heavy shaved nut sack covering two egg-sized testicles. His legs were well-muscled. With the dark black python resting on the bed, he was a fucking bull. I was staring because it was so absurdly intoxicating for me to be sitting there like that.

“Holy cow,” I murmured.

I was thinking about how he was going to use my mouth and ass. And he was a fucking giant. I was a little worried about the bed. The bed already seemed small compared to his size. However, I tried my best to do my job. I don’t want him to get angry at me.

A few hours later, the lunch bell rang, and he woke up. I was dying to know his name, but he said I couldn’t say anything until he…

“You already saw some of them eagerly waiting for you to go in there. They’ll feast on you. And you also know the guard won’t even look at what’s happening. They only care about the money we give them,” he said while he was standing naked in front of me.

My face was at his chest level. “I have only a few years to go. I don’t want to beat a boi like you to make my bitch. So here is the fucking deal. You can kiss my cock right now and become my bitch. Then nobody will even try to touch your hair. If not, then be my guest…” He showed me the jail hallway.

I could hear the guards unlocking the door, and in a few seconds, it’d be ours. I wasn’t waiting for the decision, which I made immediately. I saw him in this cell. I was just trying to fool my straight brain. In real life, it wasn’t as simple to perform as the articles indicated. I got on my knees and gave his cock shaft a soft kiss.

“Make it sloppy and this time kiss on the tip,” he replied and he didn’t even look at me. For him, it was nothing more than a regular breakfast.

I tried one more time, and this time on the tip of his cut cock. It wasn’t as bad as I expected. I thought the smell would make me sick to my stomach, but it seemed nice and clean.

“It seems you like it. I thought you’d vomit your first kiss,” he responded. “How’s the smell?”

“It smells good, nothing disgusting,” I replied frankly.

“Nice, now respond to me as a bitch. Make it as slutty as you desire my cock. Show me that you are my bitch,” he growled.

“I really do like your smell down there. There’s something about your scent that I really love. It’s familiar, it’s pleasant, and it’s enticing,” I replied like a slut with a puppy face. I was always good with my words, and now it worked like an atom bomb.

“Wonderful, someone did their homework very seriously,” he replied with a grin. “Okay, get up. Time to launch. Everybody calls me Shaw. You call me Daddy. Understand?”

“Yes, Daddy.”

To be continued…