Jail House Sissy

by

Nina Ellender

 

Chapter 1, The Grooming

 

Hi, my name is Allan. I spend my evenings hanging out in adult bookstore video arcades, looking for sex with strange men. When I go to these places I am always in my female identity. Then I am not Allan, but Nina. I arrive at the adult bookstore and keep it low key. I'm usually wearing baggy sweats and a baseball cap, a nondescript little guy that no one gives a second look to. I purchase the required amount of tokens to gain admittance to the arcade, and go back and get a booth.

Once in the booth I lock the door and quickly go about my transformation from Allan to Nina. I strip completely nude and step into the high heels that I had tucked into the waistband of my sweats. Then I tie a slave bandana around my head, Aunt Jemima style. I apply some red lipstick, throw a few tokens in to get the porn started on screen, and unlock and crack the door to the booth. At that point I'll proceed to have sex with any man who comes in the booth, often as many as 15 or more men a night. I am a total submissive ho enjoys giving men blowjobs, eating guy's ass holes, and being fucked in my ass. I wasn't always like this. Once I was a straight guy with a wife and kid. But some bad judgment on my part ended me up in the state prison, and turned me in to the cocksucking, lipstick, high heel wearing sissy I am today.

 

I got married to Jen when we were both 17. She was my first girlfriend and I knocked her up 2 months after our first date. Looking back on it, Jen was the aggressor in our relationship from the get go. It was she who initiated sex, and it was she who took my virginity. When she told me she was pregnant I quit school and got a job at a valve factory in the city where we lived. Jen & I moved in to a third floor apartment. It was actually a pretty good life. Jen was pretty, easy to get along with, and hot in bed. We'd spend our evenings cuddled up on the sofa in front of the TV, munching on popcorn. Even after the baby – Kylie – was born, things remained good between us. Then I met Ed Cunningham. Ed worked with me in the valve factory. He was 32, a biker, maybe 6', 2", tattoos, great personality. In short, I hero-worshipped Ed. I began spending time with him and his buddies after work. They had a clubhouse and we would go there to drink beer, shoot pool, etc. These guys operated on the fringes of the law, some were outright criminals. I wasn't really in their league – they were rough, tough biker types, and I was a little guy who couldn't fight his way out of a wet paper bag. They tolerated me, and I did every thing I could to please them, dying for their respect.

One afternoon the guys asked me to go with them to knock off a convenience store. All I had to do was drive. I really didn't want to go, but I felt I couldn't let the guys down. Long story short, the clerk was shot, we were caught, and I ended up with an 8 year sentence in state prison. Jen was devastated, but promised to wait for me.

 

I arrived a Folsom shortly after my 18^th birthday. I looked more like 14. I was 5', 6", 118 lbs, almost no body hair or muscle tone to speak of – I looked like a kid. I had been told ever since I was in County Jail awaiting trial & sentencing that I would be raped when I got to Folsom. In County, the guys I had robbed the store with protected me, but at Folsom I was on my own.

I was raped my first week in. One of the inmates, a black dude named Marcel, told me he could hook me up with some weed. He told me to come to the laundry room after evening chow. Marcel was there with 8 other black dudes. Marcel took me to the back, where a bunch of mattresses were stacked. Suddenly a big dude grabbed me from behind, put me in a headlock, and pushed a shank up to my throat. "You got 2 choices, bitch," he said. "Live, or die." I thought of Jen & Kylie, I wanted to live.

Because I submitted willingly, my rapist were fairly considerate of me. They had me strip nude and give them all head. I had never sucked a cock before, but years of watching porn had taught me the method. Then they anally raped me. After they threw dice and I was informed that I now "belonged" to the winner of the dice game, a guy named Roland.

The next morning the guards told me to "roll it up." This meant I was being moved to a new cell. They put me in a cell with one of the meanest looking guys I have ever seen. He kept staring at me as though I had offended his mother. He looked really pissed off. I was getting really scared now, because I knew the guard was about to leave, and I would be alone with this guy who looked like he wanted to kill me. He was easily 6', 4, well over 200 lbs, and all of it muscle. He was wearing only boxer shorts and his body was covered with scars and tattoos. He was black and his head was shaved. He really looked like a devil. As soon as the C.O. left, my cellmate said, "Take off your shit."

I looked at him. "My what?" I started to say, but was cut off by a slap to the side of the head so fast and hard it made my eyes tear up. "You clothes, bitch! Don' make me tell you again."

I quickly stripped naked. "Now pull my draws down, foo," he said. I reached over to grab the waistband of his shorts. "What the fuck is this!" he yelled. He slapped me again and I could feel my left eye starting to close up. "But you told me –"

"Bitch, when I tells you to take down my draws, you bes' be on you knees." I sank to my knees and pulled down his shorts. His penis was hard, and it was the biggest cock I had ever seen with my own eyes. He didn't have to tell me what was expected of me. I took it in my hands and flicked my tongue around the head, then engulfed as much of his dick as I could. I filled my mouth with saliva and swirled my tongue around and up and down his cock. "My nuts, suck my nuts," he said. His balls smelled sweaty, but I sucked on them anyway. He sat on the edge of the rack and raised his legs. "Eat my ass," he said. I put my face up to his ass but drew back. It smelled like a mixture of the faint smells of sweat & feces mixed. He grabbed my ears roughly and pushed my face into the cleft of his ass. I began to eat his ass the way I used to eat Jen's pussy. Apparently this was good, because I could hear him grunting in pleasure. I continued to eat his ass, suck his balls, and cock.

Finally he said, "Hand me that hair food over there. I looked to the shelf. There was a tub of what looked like Vaseline. It smelled like coconut. He greased up his dick and told me to squat on the bunk on my knees. He got up behind me and mounted me, his hard dick pressing up against my tight anus. He pushed his knee in between my legs so I couldn't close them and lunged his cock into my hole. I screamed in pain. I felt his huge hand clamp over my mouth as he hunched into my unprotected ass. His dick was pressing up to my bladder and I felt like I had to take a piss really bad. Then his entire body tensed and he shouted out with pleasure as he released his semen into my belly. When he was finished, he slowly eased his greasy cock out of my ass. It felt exactly like I was taking a hard, constipated shit.

This was my introduction to the man who would own me body and soul for the next 8 years. His name was Jose, a black Puerto Rican, who was doing 2 consecutive life terms for rape, torture, & murder.

  

  

  

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