3/7 Prison Sissy Stories – PRISON WOMAN

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I’m all about.

A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison – and that is true. But I guess it would be more accurate to say that it took prison to bring the woman that has always been inside of me out.

Had I not gone to prison I might have continued to repress my female self and ended up like a lot of wannabe women who dream about expressing their femininity, but who either never do or who do so in a very limited manner, thus enduring a lot of frustration.

I’ve talked before about how when I was 13 and beginning to masturbate several times a day, I rummaged through my Mom’s dresser and felt of her nylon hose and panties.

Before I knew it I had some of her red lipstick, the panties and hose on and was standing in front of her full length mirror in her high heels. I was astonished when I saw myself transformed from a skinny, slightly built adolescent boy, into a pretty, hot looking woman.

I jerked off and after that began wearing her heels and lipstick when she was at work. In those days I tried to rationalize that I wasn’t gay because I always jerked off to the pics of sexy nude women. It was only later that I came to realize that I was actually identifying with the women in the sex magazines.

When I was 18 I joined the navy and was stationed in the Philippines. I began hanging out in the bars there, especially the “Blowjob Bars”. These were basically brothels where you could go and get a bareback blowjob for about 10 bucks in U.S. money. They had their prettiest girls on the floor – wearing nothing but high heels.

If you wanted a blowjob you would give the money to the floor manager and the girl of your choice would be taken to you to the back of the bar by a bouncer. There was a long corridor lined on either side with stalls, kind of like the partitions in between urinals.

And, like a stand up urinal, a man could face into a stall, take out his dick and, instead of pissing, a whore would suck him off. In the stall was a basic bench where the john could sit while the girl sucked his cock.

If you wanted a cheaper blowjob you could take your chances at the glory holes, behind which were supposed to be women. You paid the floor manager, stuck your cock through the hole and would receive a blowjob.

The rumor was that the very old, the very young, the ugly, and even men were on the other side. That’s where I met my wife, Marilisa.

She was only 17 then and one of the most popular girls in the bar. She told me that some of the girls behind the glory holes were just kids. Hey, that’s the Third World for ya, eh? Mari and I got married as soon as she turned 18 and I took her out of the bar.

When I got out of the Navy Marilisa and I settled down and I got a job selling furniture. Mari and I had sex all the time, and I really convinced myself that the crossdressing thing when I was a teenager had been an anomoly.

But sometimes when we were fucking, thoughts of being a woman in a man’s big arms crept into my head. I saw the way men would look at Mari whenever we went out, and I began to get excited by the thought of her fucking another man.

One night Mari and I went to a club. She was dressed really provocatively – at my encouragement – and we both had quite a lot to drink. Mari is a really good dancer, but I have no rythym at all, so when a guy asked her to dance I told her it was ok.

The guy led her out onto the floor. He was a black dude, about 6′-3″. Mari’s only about 5′ tall, but she is built – beautiful legs and nice tits. Anyway, they were dancing and then they began to freak. She was rubbing her ass up against his groin, he was bending down to kiss on her tits.

Everyone was watching and suddenly the black guy reached down and stripped off Mari’s panties, right there on the dance floor! He made a show of holding them up to his nose and inhaling them before stuffing them into his pocket.

I was totally humiliated. When she got back to the table we got into a screaming match and I slapped her. Before I knew it the black guy she had danced with had me by the collar and was slapping the shit out of me. Then he threw me back with such force I hit the table and blacked out.

When I woke up they told me that Mari had left with the black guy, Leon. I found out later That Leon had taken her to his crib and fucked her about 6 times before he kicked her ass out the next morning.

She was hoping she could stay with him, so she was begging him to let her stay. Finally he got pissed off, grabbed her by the arm, walked her naked to the door, and threw her bare ass out on the landing outside his apartment and locked the door.

My wife was completely naked because her clothes were still in his crib. After a few minutes the door opened and he threw her clothes out. That’s the night she got pregnant from him.

After that whenever Leon wanted pussy from my wife he’d call the house and she’d drop everything and run over to his crib to suck his cock or fuck him and his patnahs.

One night Leon had a bachelor party, and my Mari was the whore of 16 black men that night. Leon put her to dance nude in just high heels, and then have party sex with all of those men while he video taped the whole thing.

Part of that tore me up, but another side – a very dark and wild side of me – was thrilled to hear the story, and even watch a copy of the video one night when Mari was out with Leon.

My wife has a gorgeous body, nice jiggly tits, a big ass, beautiful legs, a face like an angel, and long, silky black hair. She looks a lot like the porn star Luci Thai.

Anyway, Mari and I hadn’t been able to have kids, but she got pregnant right away from Leon. And when she gave birth to his baby – a beautiful half black, half filipino boy – it just gave Leon an excuse to come over our house to see his son.

And when he came over, he and Mari always somehow ended up in bed, leaving me to sit in the living room to listen to the sounds of them making love in our bed.

Leon considered Deandre his son and even named him, even though my name was listed on the birth certificate as Deandre’s father. When Deandre was born it was obvious that he was african-american, so it was kind of embarrassing the way the hospital staff looked at me.

But Mari wasn’t embarrassed at all; she told everyone that Deandre was her boyfriend’s baby. She told me that she was proud of it and that I should “get over it”.

About 6 months after Deandre was born I got drunk and drove up on a curb, hitting an old lady. This was my 3rd offense and I was sentenced to 8 years in state prison.

Well, my hidden dream finally came true because I got raped when I went to jail for felony drunk driving. Mari couldn’t come up with the bail, so I was brought upstairs and incarcerated on Tier 3 North. I was 26 but looked more like 16 – slightly built – and obviously very frightened; basically a fish out of water. An old inmate told me that the blacks were going to rape me after evening chow.

That’s when the guard locked the tier and went downstairs to help out in the booking office. The guards were supposed to do rounds every half hour, but the old man told me that once the tier was locked down at 6 pm, it would be very unlikely to see a guard until almost 11 pm. In between that time, he said, “all hell goes on up here.

” He said that I should pc up because I was married and probably wouldn’t be convicted anyway. But another guy said if I pc’d up I could end up getting shanked later. “You’ll be ok,” he said. “Just stick with me and I’ll watch out for you.”

Well that turned out to be exactly the wrong thing to do, because that guy was working for the blacks. As soon as the tier was locked at 6, he delivered me to my rapists. They didn’t beat me up or anything, they told me they were going to knock all my teeth out and kill me if I didn’t do what they said.

They made me strip naked and 2 of then grabbed my upper arms and walked me down to the shower room, which was adjacent to the dayroom. The dayroom was packed with screaming inmates. They were watching a basketball game on the tv. As soon as the blacks brought me into the dayroom everything got quiet – everyone knew what was about to go down.

I was led into the shower by the 2 blacks, followed by 12 other black men. They drew the curtain and one of them turned up the tv. For the next 5 hours I was forced to suck cock and take over 15 cocks up my ass. Because I was cooperative they used grease, but the pain was agonizing anyway. While this was going on my wife was in our apartment, only a few blocks away, with no idea of what was happening to her husband as she watched tv.

The next morning I was informed that I had been sold to a handsome, muscular black inmate named De Shawn, and that I had to request a cell change so that I could be in DeShawn’s cell. That’s when my true hell began. DeShawn was a very big guy – 250 lbs, 6′ -3″, dark black complexion, all muscles and prison tattoos.

When I got to his cell he just glared at me until the guards left. When they were gone he told me to “get nekkid”. I took off all my clothes and he said, “Take my shots down, sissy an suck my dick.”

I did as I was told and gave him a blow job until he ejaculated in my mouth. The taste of cum made me gag and some of DeShawn’s slop spilled onto the floor. He slapped the side of my head so hard I saw stars. “Don’ be wastin’ that shit, bitch!” he yelled, forcing my head to the floor. “Lick it up!”

Frightened out of my wits I lapped the cum up off the filthy floor. When I was done DeShawn said, “You my sissy now. You a woman now – you name Jeannie from now on – you got that?”

I nodded mutely and got another hard slap. “Bitch, you answer me when I aks you somethin! You name Jeannie now – got that?”

“Yes”, I said. Boom, I got hit again. I began to cry, not understanding what I had done wrong. “Yes, Daddy!” he yelled at me. “You calls me Daddy!”

“Yes, Daddy,” I said. “My name is Jeannie.” I could feel my left eye swelling shut from where he hit me. The awful reality began to sink in; I had lost everything – I was a woman, a slave, owned by another man , just like a woman out on the streets.

DeShawn handed me a xx size tank top t-shirt. “Dis what you wear from now on,” he said. “it fit you like a shot dress, want you to show off you arms and bare legs now that you a woman. He handed me a packet of cherry kool-aid. “Mix dis with a little water and cherry up you lips an cheeks. You need to look sexy cause you got to make me some money – startin right now.”

So that’s how it all began for me. Two weeks later DeShawn told me after evening lockdown that I was gonna take a ride in the “Covered Wagon.” That’s when you strip complely nude and get on the bottom bunk facing away from the bars.

Then you scooch up so that your bare buttocks are pressed up against the bars. At that point your thighs are tied tightly against the bars with strips of torn sheet so that you can’t move forward, but you can move enough to wiggle your buttocks.

A towel is placed over the bars so that you’re hidden from view in case a guard makes rounds. Then you basically get gangfucked in the ass until lockdown – some 5 hours later.

The reason I had to ride in the covered wagon was because Daddy said I wasn’t making enough money to pay down my debt to him. After about 5 men had me, I could feel the cum slopping out of my hole. DeShawn to a rag and wiped the cum off my ass.

He did that after every 3 or 4 men. And if I wasn’t giving up enough wiggle DeShawn would touch my bare buttocks with the lighted end of a cigarette. “Shake back, bitch”, he’d yell. “Give the mayn some wiggle!” I was a complete whore now, I was no longer a man. Just a prison bitch – a woman.

After a few weeks I was convicted and sentenced to 8 years in prison. at the prison intake I was given a complete medical exam. The doctor inserted a finger into my rectum and said: “I thought you said you weren’t gay.”

I’m not,” I said. The doctor said that he knew I was lying because I had bruising around my rectum, and also anal warts. I hung my head in shame. He asked me if I had been raped. I nodded my head. Then he asked me if I wanted protective custody. I told him that I didn’t, but what I didn’t tell him was that I had already been sold to an inmate in the prison and that it had all been set up. DeShawn had specifically told me that if I took PC I would be killed.

So I told the doctor that I didn’t need PC. “Do you know what’s going to happen to you in there?” He asked. “Whatever they did to you in county jail was nothing to what’s gonna happen to you in here.’ I hung my head in shame and fear. I knew I was going to become a prostitute, a prison “woman”.

When I arrived at the state prison the inmates were waiting for me. The inmate grapevine is everywhere, and inmates I had been in county jail with had carried the news of my coming, my sissy name, and who I belonged to. DeShawn wouldn’t be coming to the prison until after his trial, so he had sold me to a member of his gang – a black man named Batuco.

When the guards walk a new inmate to his new tier, the inmate is stripped nude, handcuffed, and walked by the arm by a guard to his cell. The inmate carries his jumpsuit and a towel in his hands, and is subjected to the jeering and taunting of the entire tier. As I was walked through the tier the men were screaming “Hey, Jeannie! I can’t wait to get up in that ass, baby!” Or “Jeannie, you mayn’s waitin on you, girl!”

The next night I was in a cell with 8 black men, having bareback sex with all of them! I had to suck cock and get fucked in the ass by all of them. They tattooed my buttocks – the word BARE on my left buttock, and the word BACK on my right buttock.

Afterwards they threw dice and I was informed that I now “belonged” to the winner of the dice game, a guy named Batuco.

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 Mari’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 badly. 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 Batuco, a black Puerto Rican, who was doing 2 consecutive life terms for rape, torture, & murder.

After Batuco fucked me in the cell, he laid down the law, and explained to me how things were going to be from now on. He asked me my name, and when I answered, “Don,”

Batuco shook his head. “You name Jeannie now, ” he said. “One thing you gots to understand,” he said, “is that you a lady from now on, a woman, y’unnerstand?”

All sorts of thought were going through my head. I’m a woman? Ok, he wants me to play the submissive role, I get it. But I didn’t really understand just how much of a woman I was expected to become. Batuco seemed to read my thoughts. He grabbed a punk who was hanging around, eavesdropping, and sent him to get “Baby.”

After about 5 minutes Baby showed up. My eyes almost fell out of my head; this really pretty woman was standing in the cell doorway! She was about 5′, 8″…115 lbs, red hair, green eyes, pale skin covered in lots of jail house tattoos. She was wearing red lipstick and green eye shadow. She had on a tank top t-shirt, and work boots with dark socks rolled down.

I couldn’t believe they had women in with the male inmates. Batuco looked at me and laughed. “Lift up you dress, Baby,” he said. The girl complied and I immediately saw that “she” had a penis and testicles. Baby was a guy! It was then I realized what was in store for me. Batuco told Baby to take me and train me.

Baby took me to her cell and gave me a tank top and told me to get out of my clothes. I would be wearing dresses from now on.

Baby showed me how to make lipstick out of a mix of Kool-Aid and Vaseline. She told me that Batuco would treat me good, but only if I made him a lot of money, and obeyed everything he said.

I asked her how was I going to make money. Baby laughed hard. “Nigga, you a ho now!” she said “Batuco OWN you ass. He you Daddy now. You gots to get out on the stroll and hustle for you man.”

So, I was to be a whore. Baby told me that if I wanted to really make money I was going to have to get really feminine. She showed me how to walk, with lots of sexy wiggle, how to move in a delicate, feminine manner, how to give men sexy looks. She gave me a bandana and told me that it was a “slave bandana.”

“Daddy’s gonna shave you head, prolly tonight, so you wear this.” I was to learn that shaving a punk’s head was standard operating procedure. It was the first outward symbol of an inmate becoming another man’s punk.

Sure enough, that night Batuco had my head shaved skin bald. If I thought that his was outrageous I was in for a lot of surprises. Over the next few weeks Batuco had an 8-ball tattooed on my skull. I was crying and Baby told me, “It aint shit, all Batuco’s bitches got a 8-ball on they haid.” Baby showed me her ass.

Tattooed across the small of her back in big letters was: BATUCO. Underneath that, across both ass cheeks was: PUERTO RICO. “You gone have like that, too,” Baby said

And within a few weeks I was all tatted up, just like Baby. I had SISSY tatted across my upper right arm, and PUTA across my left upper arm. Well, that’s it, I was marked for life. So I became a feminine little whore.

At first I was a slow starter, but I soon learned what makes a man happy, and after a few ass whippings from Batuco for not bringing home enough money, I soon became his best earner.

One thing Baby kept telling me about was not to get Batuco pissed, because if he really got pissed he would take a bitch to the laundry room for an ass whipping, and that the ass whipping administered in there was severe. She pointed to Chrissa. She could hardly walk. There were big black and blue bruises all over her arms and legs. “She got taken to the laundry room,” Baby whispered. “Daddy caught her giving money to another man”.

If I wasn’t scared of Batuco before, I was terrified of him now. All the girls told me that sooner or later Daddy would take me to the laundry room, that no girl had escaped it, even Baby.

One night, after chow, I was talking to a guy and I happened to see Batuco staring at me. He looked really pissed. “Get over here, girl,” he said. I was really scared, but I smiled. “Hi, Daddy, I said loudly. “I gots some money for you ,Daddy.” Batuco stared hard at me. “You givin money to that foo over there?” he said.

“No way, Daddy,” I said. Batuco grabbed me firmly by my upper arm. “You know, you been getting really sassy lately,” he said. “I think you need a lesson.” Still holding me by the upper arm he began pimp walking me down the cellblock. I was babbling, begging him for another chance. Everyone was looking at me, some looked pitying, others were laughing.

We were heading toward the laundry room. Because Batuco was so tall and I was so short, I had to sort of run to keep up with him. When we got to the door of the laundry room a C.O. was there. If I thought he was gonna help me I was mistaken. He looked at me and laughed.

“Uh-oh..looks like someone fucked up,” he said. Batuco laughed. “We just goin in to fold sheets, boss,” he told the guard. The guard laughed. “Yeah, ok, whatever you say,” he said, unlocking the door. Batuco dragged me inside. “How long you gonna be?” the guard asked. “Bout an hour, boss,” Batuco said. The guard closed the door and I heard the lock turn. My heart sank.

“Get you shit off,” Batuco said. I began undressing, all the while babbling and begging him not to hurt me. “I’ll be good, Daddy,” I whimpered. “I’ll do anything you say, Daddy..PLEEEEESE!”

Batuco didn’t answer. When I was nude, except for my work boots and bandanna, Batuco told me to reach under the desk and get what was there. I got down on my knees, eager to obey, feeling around. My hand hit an object. I grabbed it and pulled it out and brought it to him. He was sitting on a stack of mattresses, reading a porno magazine.

While I waited I looked at the object in my hand. It was a bunch of wire coat hangers wrapped in black electrical tape.

After a while Batuco looked up. “You know what that is?” he asked me. I shook my head. “What is it, Daddy?” I asked obsequiously.

“That a pimpstick,” he said. He reached under the mattress stack, and pulled out a bunch of rags. He shook them loose and I could see that it was a bunch of rags tied together to form a crude rope.

He pointed to a foot stool. “Get up on that,” he said. I obeyed him. He tied one end of the rope around my left wrist.. “Raise your arms,” he said. I was crying and shaking in fear.

He threw the loose end of the rope over the water pipes just above my head. He pulled my left arm up and tied my right wrist, so that now both my arms were tied above my head. If you’ve never had that done to you, you can’t even imagine how painful that alone can be.

Batuco reached into a laundry bin and pulled out a dirty sock and stuffed it into my mouth. Then he taped my mouth up with duct tape, and kicked out the footstool and I was hanging, my feet just off the floor. It was around 7 p.m. Right about now Mari & Deandre would be on the sofa, watching TV. I could have been with them, safe and secure in my own home, instead here I was, hanging naked from a pipe in a dirty cold prison, about to get a brutal beating from the man who now owned me.

Then he hit me, across the backs of my thighs. If my mouth hadn’t been taped my screams would have been heard out on the street. I don’t think I have ever felt that much pain. I was screaming through my gag, and writhing in naked agony as Jose administered the brutal beating.

My entire body was beaten, everything but my face and genitals. I don’t know how long the beating lasted, probably no more than a few minutes, but it felt like hours. Finally it was over. Batuco was breathing hard and sweating. He took off his shirt and put the foot stool under my feet, and untied the rope. I was damn near in shock from the pain and I would have fallen if Batuco hadn’t picked me up and carried me to the mattresses.

I notced that his cock was hard. He pulled his pants off and told me to get down between his legs and suck him off. I was in so much pain that the last thing I felt like doing was sucking cock, but fear made me give him a really good blow job until he ejaculated into my mouth.

When we were done we got dressed and Batuco knocked on the door to be let out. I was wearing just an xx large tank top, cut and sewn to fit like a minidress. The guard saw the bruises all over my arms and legs, but when he saw me looking at him he quickly shifted his gaze.

After a couple of days the pain of the ass whipping gradually faded, and the bruises got darker, black, blue, and purple, and I actually began to feel proud because in a preverse way, I guess I felt that the beating showed that my man loved me. I had 8 years to go.