Becoming a Woman in Prison Ch. 01

Chapter 1

I hear footsteps enter the room on the opposite side of the wall of the dark room I'm in. I'm on my knees staring at a hole, and my mouth is watering. My heels are anxiously shifting as I adjust my mini skirt, my smooth and chunky ass and thighs popping out of it, my tiny dick starting to pulse. I run my fingers through my long straight wig. Yeah, I'm not a woman, at least not full time. But it's where I feel the most comfortable. However I spend most of my time as a man except for when I come here to this video store off the I-75 exit. Here I am comfortable enough to dress up and take dick through a gloryhole. I've been out of prison for about three years but to be honest I miss it a lot! That's where I became and was accepted as a woman. It wasn't overnight, for the most part I thought I was straight, except for a few dicks I had sucked in college before I dropped out. I liked it but always imagined having a wife and kids. That ship has sailed though.

I can hear a man approach the gloryhole, and my mouth is now dripping as I hear a zipper unzip. Yes! This guy is big, but perfect for me! He inserts his big black cock (my favorite) through the gloryhole, its soft and drooping down far below where the hole ends. That's my cue, and I get to work. I use the suction of my lips to slurp his big tool into my mouth and down my throat like a noodle. I hear a small grunt as the cock twitches, slowly becoming full of life and hardening. I'm a pro, and I start guzzling his cock, using one hand, then two as he becomes fully erect.

"God damn..." I hear through the hole as I bob up and down on his dick like the good sissy I am. I use both hands and my mouth in a circular motion as I slurp his dick up and down. His cock head is big, just how I like it! He thrusts into my hands and throat now and I begin feeling erratic movements, realizing he is getting close. I speed up, not breaking rhythm. Then I hear a knocking on the wall, my favorite part. I shove the entire cock into my throat, my lips to his groin as he cums.

"Oh fuck ohhhhh fuckkkkk" he exclaims as I feel spurts of cum fire in my throat, I drink it straight down, not to be wasted! His groaning becomes quieter as he slows his thrusts. The cock leaves the hole as I swallow my sticky throat. I want more. He leaves the room and after a minute I hear another guy enter. Perfect!

*******

Throughout my life I've always been in the wrong place at the wrong time. And when I was arrested, it was no different. I was in a robbery gone wrong, one that I should have never agreed to. I was the getaway driver and was told the guns they were using were fake. Things went south and I found myself facing 10 years in prison. I was scared shitless, being a short white guy that had always been called 'soft'. My voice was high pitched and I'm pretty sure I had an imbalance of hormones, since I never grew hair on most of my body. My dick was small and for some reason God gave me thick legs, birthing hips, and a nice hairless round booty. I even had little bee-sting man-boobs and was easy on the eyes. I was done for!

I remember when the corrections officer who did my strip down almost laughed when I undressed.

"What's so funny?" I asked.

"Boy you got a woman's body. I give it an hour before you become someone's punk."

"Ain't that the truth." Another voice said, I turned to see a different CO looking at me like I was a piece of meat. I could see a slight bulge in his pants forming.

I blushed, and felt awkward but a little turned on for some reason.

"Easy Mendez, this one's gonna get claimed quickly by the top dog."

"A man can dream can't he?" The other CO said as he shuffled his pants to hide his boner.

"Alright inmate 3962, you are good to go. Put these on." He handed me an orange jumpsuit, one way too big for me.

"This isn't my size." I said.

"Trust me, you're gonna wanna hide those curves," he said. I again blushed and felt oddly turned on. I had never felt 'wanted' in my life, women never liked me, probably because I was so petite and curvy. I had sucked off a couple of jocks in college before dropping out, but never considered myself gay. I didn't necessarily not enjoy it though, but always thought of it as a phase.

"Follow me, we will take you to the floor where you'll be assigned a cell."

Ten minutes later I entered a large communal area filled with other prisoners. From the moment I walked in, all eyes were on me. I heard several comments and barks as I walked to find a seat on a bench.

"God damn!"

"He look like a woman!"

"Wassup mama?"

"Oh shit we got a new lady!"

I felt a lot of anxiety but also was kind of turned on... This is the first time in my life I had all eyes on me, even if they were men. Most were jacked and muscular, shaved heads. Here I was this little smooth white boy. Apparently the oversized jumpsuit didn't hide much, these guys had a sixth sense. I also spotted a few feminine guys, one of which was blonde with short shorts, and wore a bandanna. He, or she, I should say, I couldn't tell, she looked like a woman! She winked at me, almost saying her own welcome. Her legs were thick and ass round, her shirt tied up halfway to emulate a belly shirt. She was next to a large black man working out, surrounded by other men. He looked at me with a smile, like I was a piece of meat. He was hands down the biggest man in here, and the way the others gathered around him I could tell he was top dog. And the femboy with the bandanna next to him was his, guaranteed. A voice came over the intercom.

"Rec time is over, all prisoners make your way to your cells."

"Inmate 3962!" I heard, taking a second to realize it was my name being called. "You've been assigned a cell. Come with me."

The cell was small, with a bunk bed, a shelf, and a toilet/sink. It wasn't much. A man sat on the bottom bunk, and I then realized who it was. It was the top dog from the floor I saw working out. My stomach dropped. He must have been seven feet tall, muscular, and hands that looked like banana bunches. He turned to look at me, smiling in a way that made me uncomfortable but turned me on slightly.

"Home sweet home." said the CO as he slammed the door shut, only a tiny window looking into the outside. The man sat up.

"My name's Devon. What's your name?"

"Chris..." I said, feeling like it was the first time speaking since my intake.

"Damn your voice is light... nah.. Your name Clarissa now."

"Clarissa?"

"Yeah. You my woman now." I could feel my tiny dick harden a little, but I didn't want to show it.

"You can't change my name-" Suddenly, Devon shot up from the bed, towering over me. I looked up, intimidated.

"I can do whatever the fuck I want. Now we can do this the easy way or the hard way. Ima ask you again... what's your name?" He said as I shivered with fear. I paused, not a good idea. THWAP! I saw stars as Devon slapped me, causing me to fall back.

"C-clarissa..."

"Good girl. Now here's how it's gonna be: you belong to me now. And Ima make you a woman. "Got it?"

"But-" THWAPPP. Again he slapped me, nearly making me spin.

"Got it?"

"Y-yes."

"Yes what?"

"Yes, I'm your woman..." I muttered, terrified.

"Good girl. Now come here." He said as he sat on the bed. I knew better than to do anything else. I followed him to the bed.

"On your knees." Immediately I got on my knees. I didn't want another slap.

"You ever suck dick before?"

"Yes, a few times, but I'm not gay."

"Nah you ain't gay, you a woman now. Now suck this dick." he said as he nodded to his bulge. It made me gulp, I could see the outline of a snake in his pants. I ran my hand along it, pulling down his sweatpants. It was the biggest dick I had ever seen, the cock head being so large it looked like a portabella mushroom. It had been years since I sucked a dick, and even then they were smaller white dicks, not this size. I gulped as i held his dick in my hand, weighed down like a giant sausage, and it wasn't even hard. Devon moaned as I started stroking it softly.

"Put it in your mouth." I didn't hesitate. I put the tip in my mouth and sucked, and could feel his dick getting harder as I stroked it and licked the tip.

"Deeper." Devon said, and I began shoving it more into my mouth, it his the back of my throat, making me gag.

"Relax your throat, you got a lot more to take." he said as I awkwardly tried to take the whole thing. I kept gagging. Devon laughed.

"Ima teach you how to suck dick Clarissa. Work it with your hands, both hands."

I began working his cock with both hands while sucking on the tip, feeling him become rock hard. It tasted musky and salty, I could taste precum. It reminded me of sucking dick in college, and I could feel my little dick becoming hard. Despite being slapped, this was turning me on! Devon pushed me off of his dick, looking at my body.

"Strip naked." he said, as he stroked his massive 10 inch dick. I immediately took off my jumpsuit and Devon gasped.

"Fuck you got a body." Devon said as he spun me around. He grabbed my ass. "Bend over" he said, I bent over. I could feel his large hands groping my ass, and it felt good. I have never had someone get turned on by my body and this felt new and exciting. I felt my tiny dick become hard. Devon could see this.

"Yeah I knew youse was a bitch. My bitch." Devon said as he groped my ass and then my tiny dick and balls with one hand, a thumb between my ass cheeks. I got so turned on!

"You ever been fucked?"

"no.."

"Well we gonna change that, but I gotta widen that pussy up." Devon then forcefully stuck a finger right into my hole. I let out a whimper, it honestly hurt, but my dick pulsed too, making it kind of feel good.

"Yeah you tight. I can tell you like it." Devon said as he reached another hand around to feel my tiny dick wet with precum. "Back on your knees."

I got back on my knees and continued sucking Devon's massive cock. I could tell I was bad at it the way Devon kept laughing, but he seemed to enjoy it. Secretly inside I took it as a challenge and wanted to prove Devon wrong. I stroked with both hands and my mouth, finding a decent rhythm, I could hear Devon begin to moan, I was doing something right.

"Yeah suck that dick bitch... yeah like that..." Devon moaned, turning me on even more. I took one hand off his dick and started fondling mine, its so small i just use two fingers to jerk it.

"What you doing?" Devon said, grabbing my hand and putting it back on his cock. "You don't touch it unless I tell you to. You don't cum unless I say you can."

"But it feels good!" I said in protest, Devon grabbed me by my neck and squeezed, jerking my face up at him.

"You don't cum. Unless I tell you too. Got it?"

"Yes.." I managed to get out, feeling no oxygen coming into my lungs.

"Yes Daddy." He corrected me.

"Yes Daddy" I said, as he released his grip on my neck.

I continued working his cock relentlessly, learning to work with my hands and mouth, then with my mouth only, then with my hands, repeat. This seemed to bring Devon pleasure. He was soon moaning loudly and groaning, saying things like "yeah bitch" and "Like that like that". He would lean forward and grab my juicy thick ass and thighs, making me feel really good about my body, which was new to me. Despite his violent tendencies I was turned on by how much he liked my body. It made me feel good, made me feel important, something I had never felt before. Soon Devon was jerking his waist back and forth, and the sounds became louder and louder. He was close, at least I thought, I was still inexperienced. Suddenly, Devon grabbed my head and shoved me completely down on his massive cock, he erupted with a large shout.

"IM FUCKING COMING!" My throat completely opened up as his large cock was shoved into my throat. I couldn't do anything, I had no control. I just took it, feeling rivets of cum shoot into my throat, bypassing my mouth completely and going straight down. Devon jerked erratically, and despite the pain of my throat being torn open, I was loving every minute of it! I loved hearing Devon cry out in pleasure, as much as some parts of me were feeling weird. His orgasm toned down as he panted slowly back to normal. I was left with his dick getting soft in my mouth. My tiny boner was raging, precum dripping out. I wanted to bust.

"Can I cum Daddy?"

"No."

"Please!"

"Nah. You cum when I say you can."

I felt frustrated, but there was nothing I can do.

"Was I good?"

"Yeah, but you can be better, and you will be better. Tomorrow in the showers Ima show you how my other girl Dixie does it, she used to stay in this room but I moved her out to a homies room while I turn you out. Gonna show you how she takes my dick in all her holes" Dixie must have been the one I saw near Devon on the rec floor.

"Turn me out?" I said, confused.

"Yeah. Turn you out into my sissy faggot. I'm gonna make you a woman Clarissa, my woman."

I gulped, realizing that this was now my path. I would become Devon's woman. I felt weird about it, but to be honest, it made my little dick even harder. Devon put me in bed with him, my ass pressed to his groin. I could feel his big dick as he slept. I lay awake, feeling home sick, but excited to be wanted. I never wanted to be a woman, but it was this night I decided I wanted to be Devon's woman.