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 hit 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. It's 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 to. 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.

"I'M 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 bitch. 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.

Chapter 2

That night I could barely sleep, my tiny cock rock hard and aching... I wanted to cum so badly. Devon slept next to me, snoring loudly. I liked being beside him despite my weird internal feelings. Was I gay? At this point I don't think it mattered, I was in prison, and I had just been claimed by the top dog and sucked his dick to completion. All I knew is I had a challenge and accepted it. I would be Devon's woman. I like the feeling of being wanted. For the first time in my life, I felt sexy. I laid next to Devon all night while he slept, smelling his manly body and looking at his rock hard abs and chiseled chest. I stared around the cell, taking in how small it was, missing the outside world a bit. This was it, I was really in prison. I looked at the tiny window on the door, darkness outside of it. Suddenly, Devon's snoring stopped. I felt a large hand grab my ass, making my tiny cock pulse. He was awake.

"Morning bitch," Devon said as he squeezed my plump ass cheek. I blushed, not sure what to say.

"When I say good morning you say good morning Daddy," Devon said.

"G-goodmorning, Daddy," I said as I put a hand on his chest, feeling his chest hair. Using one of his large arms, he pulled me closer to him, his hand squeezing my ass. My sissy cock pulsed rapidly, and I could feel the precum coming out, dripping against Devon's leg.

"Can I cum??" I asked, in a daze.

"Not yet Clarissa, but you can do me a favor," Devon said as I felt his hand grab mine and pull it down to his crotch. His dick was rock hard and throbbing. It felt like a tree trunk in my hand, I could feel the veins clearly defined.

"You can take care of this morning wood before wake-up call."

I didn't hesitate. I crawled down to the end of the bed, straddling Devon's lower legs as I held his cock in front of my face. It was a beautiful sight. Rock hard, veiny, and a large mushroom head that kept pulsing, as if it was breathing.

"Squeeze that cock tight and suck," Devon commanded. I gripped his dick and started licking the shaft, it tasted musty and salty, dried cum from last night still on it. I licked up the shaft as Devon started to moan, making my way to the large mushroom head. I put the tip in my mouth, trying to swirl my tongue around it, but it was so big!

"Ass up while you suck me, bitch," he said as he pushed my head down further on his dick, I felt the head squeeze further into my mouth, touching my throat. I gagged and coughed, and Devon laughed. "I said ass up. You got a lot to learn if you're gonna be my woman."

I stuck my round jiggly ass up and continued sucking, trying to fit Devon's meat into my throat.

"Arch your back," Devon said, and I did just that. I could tell he liked how I looked. He stared at my bubbly ass as it swayed while I went down on his cock. I relaxed my throat and felt his meat slide deeper into my mouth, his cock warm against my lips as he flexed his dick and pulsed in my throat.

"Yeahhhh bitch just like that," he said as I began to involuntarily moan, my sissy cock throbbing like crazy, I felt like even a nudge from his leg would make me squirt. I thought of nothing but cumming. I worked his dick with both hands as it slid deeper and deeper into my mouth. Devon moaned and groaned as I worked his cock into a rhythm with my hands and mouth. His breathing became all over the place, and I knew he was close.

"Yeahhh just like that—fuck fuck fuckkk," Devon cried out as I felt him start to cum. I squeezed his dick as hard as I could as spurts of warm salty cum poured into my throat. I went down as deep as I could, trying to swallow every last drop, cum pouring out of the sides of my mouth. Devon writhed as he thrust his cock into my throat, hand on my head pushing me further. I could feel a fire coming from my crotch as I longed to orgasm, my eyes dilating. I was living out his orgasm vicariously, wishing it was my own. His jerks came to a slow, and I sat there still ass up and back arched.

"Fuck you gonna be an amazing woman Clarissa... You a natural."

I blushed, feeling my cheeks get warm. I felt conflicted, but ultimately good about it. My tiny cock throbbed endlessly.

"Daddy can I come?"

THWAPPP! Devon slapped my face.

"No. Not yet bitch stop asking." It was painful, but at the same time nice to feel something. It took my mind off of the raging fire brewing between my thick juicy thighs.

"You gotta earn it. Today you gonna see how my girl Dixie does it. She gonna take the whole gang in the showers, and you finna watch."

I remembered Dixie, the feminine sissy I saw with Devon when I first walked into the main rec area. She was hot, almost passable.

"Dixie is my main girl, but she ain't like you. You got a natural female body... these legs and ass..." Devon said as he squeezed my thick thighs and spanked my bubble butt. I felt embarrassed but also sexy.

Suddenly the lights came on, and a loud bell rang.

"GOOD MORNING INMATES, BREAKFAST CALL"

The doors sprang open.

"Get some clothes on, we going to breakfast."

*******

At breakfast, the entire prison was eating. I sat with Devon and his gang, about thirty guys, all very tall, black, and muscular. We were clearly the strongest in the prison. I sat on one side of Devon, Dixie on the other. I couldn't stop glancing over at Dixie, admiring how feminine she was. She had short shorts on, cut from the jumpsuit, and tied her top to create a belly shirt. She wore a bandanna covering the back part of her head, with short blonde bangs coming out the front. She had fake eyelashes and makeup on, wearing red lipstick. I wondered how she got makeup in prison, but I guess anything is possible. She was short and petite, and had nice legs, not too thick, but definitely thick enough to appear a woman. Her voice was high pitched like a womans as well. I couldn't believe it. Her ass was what made me gasp; she had a tiny but thick bubble butt, and when she sat on the bench, I could see it flatten out as if a grape was being stepped on. She screamed femininity, visually and also the way she carried herself. She flirted with the other guys in the group, laughing and winking. We ate our breakfasts, which was cold grits, scrambled eggs that were watery, and a single piece of toast. Devon took my toast and ate most of my meal. I looked around and couldn't help but see all eyes were on me, the gang and also everyone around us. They stared at me like a piece of meat, and honestly, I liked it. I looked over and saw the guard that was staring at me during my intake exam. He looked at me like an animal; I could see his crotch bulging. He winked at me and turned, walking away.

After breakfast, everyone was led to the recreation room, where our gang started working out on gym equipment. I could see Devon doing pull-ups, his abs on full display. I thought back to this morning when I was looking at his abs and body in bed. My cock twinged, and I remembered how bad I needed to cum. I looked over to Dixie as she sat on a bench next to me, and continued admiring her femininity. It felt like I could never be that feminine. I felt like a lost cause.

"You should take a picture, it will last longer," Dixie said, catching me staring at her.

"W-what? Sorry..." I said, looking away shamefully.

"Don't worry about it, I like it actually. I've been staring at you too. Can't wait to see the woman you're gonna become here," she said, as I looked away, shameful but excited. "Loosen up, literally. You're gonna need that advice."

I laughed at her joke, but she was dead serious.

"So Clarissa, that's the name Devon gave you right?"

"Y-yeah..."

"What are you in for?"

I told her the story of being in the wrong place at the wrong time.

"Ah, the getaway driver, classic. Well, no changing the past now, you are on a new journey now. Guys like us aren't meant for prison, so when we get here, we become women. I was a guy too when I got here, and slowly got turned out. It's not a bad life, it has its perks," Dixie said, as she took out a little vial of white powder and used her nail to scoop some up and sniff it. She shook her head in slight pain, but then smiled.

"Want a bump?"

"No, that's okay... never was a big drug person."

"Suit yourself. Do you have any questions for me?" Dixie said as she extended her legs, which were perfectly hairless and had a woman's definition.

"How... How do I get better at this?"

"Better? You're just beginning it. It's gonna come with time. Experience. How many times have you sucked off Devon so far?"

"Twice."

"Well damn, he said it was amazing head so you aren't doing so bad. Took me at least four times to get a decent review. I kept using my teeth, I had never sucked a dick before."

"I had some experience in college but I'm not gay."

Dixie laughed. "Yeah. Keep telling yourself that. You ever been fucked?"

"No."

"Well get used to the idea, because that's the fun part. No better feeling than having a thick dick in your ass pumping hot seed into you."

My sissy cock was fully hard by now, throbbing in my jumpsuit. I tried to hide it but I could see Dixie looking at the wet spot of precum.

"He hasn't let you cum yet, has he?"

"No."

"Don't worry, you will. You just have to earn it. Learn to put the gang's pleasure before your own and it will come."

"The gang's pleasure?"

"Oh you don't know? Eventually you will service the entire gang. You belong to everyone, but Devon owns you fully. You'll see in the showers today."

I began to get nervous, but also excited... Taking more than one cock? At once?! I wasn't sure if I could handle that... taking one in the mouth was a lot.

"Don't worry, you will learn, and build stamina. Also sometimes Devon has to lease you out to other gangs and sometimes the guards. You are a product, one to be used."

I sat there in silence, thinking about everything.

"Can I ask you a question?"

"Sure, I'm an open book!"

"Why are you allowed to wear short shorts and low cut shirts? Everyone else in here is in jumpsuits?"

"The sissies are allowed, the women. Warden knows the gangs need their women to stay sane. So they look past the dress code, and the makeup. And not to mention the hormones."

"Hormones?"

"How do you think my voice got so girly? Devon has a connection, I take a pill every day and it feminizes me, makes my tits bigger. He's gonna put you on it soon."

I began getting anxiety, thinking about taking hormones. I hid this to Dixie but she could tell.

"Just relax. You belong to the gang now, you are gonna learn to accept and even want it. I am a woman now, and soon you will be too Clarissa. You're already ahead of me in so many ways."

"How? I can't even hold a candle to you!"

Dixie laughed.

"I appreciate the comment but trust me. You suck Devon's dick twice and he's already raving about you to the gang. Also your body is a ten without any hormones or training. See this?" Dixie motioned to herself. "This was all work. You walked in here looking like a woman with those curves. I have to shave whatever the hormones won't take care of. Also, this-"

Dixie took off her bandanna slightly, but so that no one else could see. Her head was balding at the back. "I am going bald, that's why I wear this bandanna. Your hair is perfect, you'll have a full head in no time."

I thought about how I hadn't had long hair since high school, and when I did, it was perfectly straight and sometimes would get mistaken for a girl from behind due to my wide hips, thick legs, and long straight hair.

A loud bell rang out.

"INMATES RETURN TO YOUR CELLS, WE WILL BEGIN CALLING GROUPS FOR SHOWERS".

Dixie got off the bench, and I got a full look at her bubble butt, her ass hanging out of her short shorts. She turned to me and smiled, she was a woman.

"Now you get to see what we do!"

*******

I made my way to the showers with Devon. He had an arm wrapped around me.

"Now you finna see what you gonna be doing one day."

I gulped, very intimidated. Soon we were walking with the whole gang, everyone carrying a towel. The corridor leading to the showers was dimly lit, and I could start to feel the humidity.

"Now, some rules Clarissa... You can touch your sissy clit but you CANNOT cum. If you do cum you're gonna be in a world of hurt, you understand?"

"Yes."

Devon shoved me against a wall, hand on my throat.

"Yes... Daddy," I muttered out. His strength turned me on but also scared me.

"Good girl..." Devon said, looking into my eyes. I felt so conflicted inside but my sissy cock was on fire. I loved being wanted, being sexy.

"Move along," said a guard, watching the whole thing.

Devon and I continued down the hall until we reached the showers. It was full of about fifteen large black men, members of the gang. Dixie sat on a shower bench naked except for her bandanna, waiting. She has her legs crossed. Her body was amazing! Perfectly smooth. She uncrossed her legs and a tiny cock popped out, already hard. All of the men around began to strip naked as well, big black cocks left and right. I stood in the back with Devon, who also stripped. He turned to me.

"Get naked and sit on this bench." I didn't think twice, I took my oversized jumpsuit off and sat down on the bench. The gang members all looked at me, admiring my body. Some started stroking their long thick cocks. They were hungry.

"Pay Clarissa no mind... today is about Dixie. You ready Dixie?"

Dixie got onto her knees, eyes lit up with excitement.

"Yes daddy, I'm ready to be used!"

"Alright boys.. Let's eat."

The crowd of men moved in on Dixie, all stroking their large cocks. Devon stayed by my side, stroking his large cock. I longed to suck it... my cock was hard and pulsing... I needed to cum.

Four men approached Dixie, who reached out and started stroking any dick she could hold. One large man held his dick out to her mouth. She immediately took it in her mouth and started deep throating it like a pro. I was in shock! She went all the way down, and the cock had to be at least ten inches. She worked it with her lips as she stroked two men on the sides.

"Yeahhh fuck yeahhh," the men moaned as she did her work. She took her hands off the other two cocks and began to focus fully on the one in her mouth. Her tiny dick swung back and forth as she worked the massive black cock with both hands and her mouth.

"I'm gonna cummmm!" the man shouted as he cocked his head back and released into Dixie's throat. On cue, she went deep on it and took the entire load. All of the men stroked in the background as the man who came moved out and another moved in. Dixie immediately grabbed another cock and went to work, almost without missing a beat. The men placed her on the bench and bent her over.

"Yes please I need to be fucked, I need to be fucked," Dixie cried. It was like something had taken her over and her only purpose was to please the cocks around her. On all fours on the bench, she stuck her round perfect ass up and arched her back, and she looked so sexy. I wanted to be her, on the bench surrounded by cocks.

I began to lightly stroke my own tiny dick, but not hard, I was so close to cumming.

Devon saw this and smiled at me.

Dixie took another cock in her mouth while another gang member got behind her and placed both hands on her ass cheeks, spreading them.

"Awww yeah this ass is perfect" he said as he smelled it and then shoved his face in, eating out her boy pussy.

"Yess pleaseee eat it eat it," she exclaimed before another dick went into her mouth.

She deepthroated that one too while the other guy ate her pussy. Suddenly the guy sticking his dick in her mouth came too, I could see his white creamy load pouring out of the sides of her mouth.

"Fuckkk yessss," he shouted as she kept just deepthroating his dick. Two cocks down.

The man eating her ass got up and slapped her ass with his dick.

"Please fuck me please fuck meee," Dixie begged. Her tiny dick was hard, I could see it between her perfect legs. Dixie was a woman, no question about it. The next cock moved into Dixie's mouth and she swallowed it without question. The guy behind her stopped slapping his dick on her ass and moved it to her boy pussy. Dixie moaned with joy as the big black cock entered her boy pussy. It seemed like it slid in so easy. He began fucking her, in and out, in and out. She cried with pleasure, but it was muffled by the cock in her throat. Dixie was a pro! This was so hot to watch, I began squeezing my tiny dick.

"Remember, don't cum," Devon reminded me. He was stroking his own cock next to me.

The man fucking Dixie suddenly came, and went balls deep as he did. I could see his massive balls touching Dixie's tiny nut sack. The man came so hard... it was so fucking hot.

The next set of men moved in, and this repeated for a while. Dixie just kept taking dick over and over in all of her holes. One man would cum, and another big black cock would replace him. Both holes, mouth and ass. Dixie loved every minute of it. She was covered in cum as it began to leak from both holes. The way she sucked dick was amazing, almost methodical. She knew how to make a man cum within minutes. It took every bit of my self control not to cum. I began rubbing my ass on the bench I was sitting on, imagining a cock going deep inside my ass, imagining the feeling of cum exploding inside me and filling me up. I wanted it again and again. I wanted to be feminine like Dixie, to look like a woman and to be fucked like one. Devon could see this.

"It will be your turn soon enough Clarissa..."

"I want it Daddy, I want to be a woman."

"I know you do. Good girl," Devon said as he patted my head.

Soon, every cock had cum except Devon's. Dixie lay in a puddle of cum, panting, fingering her ass and jerking her tiny sissy cock. Devon, rock hard, approached her. She got off the bench and got on her knees, ready for more.

"Please daddy finish me off," she begged. Devon sat on the bench and picked her up, putting him in his lap. His giant cock came up between her legs and she moaned as she stroked it. She stood up slightly and sat right on Devon's cock, her eyes went out of focus as she began moving up and down on Devon's cock.

"MMM YES DADDY," she said over and over as Devon placed his hands on her ass and began moving her up and down off his dick.

"Yeah bitch yeah take that cock," he said. I could see cum gushing out from the other men. Devon's cock was hands down the biggest. I jerked my tiny sissy cock and thought of what it would feel like to be Dixie. All you could hear was Dixie moaning and fwap fwap fwap fwap as Devon fucked her guts.

"Yeah yeah... I'm gonna cum... you ready to cum Dixie?" Devon said as he grabbed Dixie's small dick and started jerking it as he fucked her.

"Yes Daddy please please pleaseee," Dixie said as I watched them. I was jealous of Dixie, I wanted to cum with everything in my soul.

"IM GONNA CUMMMMM," Devon screamed as Dixie moaned high pitched. Her little dick squirted as Devon pulled her all the way down onto his giant cock, releasing inside of her. I imagined what that would feel like, cumming with a cock inside of me. Dixie's eyes rolled back into her head as she started convulsing. Devon moaned loudly. Everyone watched him fill her up. The whole gang. Dixie's dick stopped spurting cum, and Devon's thrusts slowed.

"Yeahhhh bitch... so fucking good."

Dixie fell off of Devon and onto the shower floor. She laid in a puddle of cum, ass up, faced towards me. Her boy pussy was bright pink and loose, having just been fucked by multiple cocks. It was leaking cum. Her mascara ran down her face. She lay there with a smile on her face as Devon got up, smiling at me.

"You gonna do this soon, so be ready."

Everyone in the room turned to me, a bunch of naked black men looking at me, cocks out. Dixie lay on the shower floor, smiling at me.

"Yes Daddy, I want it," I said.

And I meant it.

Chapter 3

I’m back at the glory hole in the video store off I-75 and I’ve already sucked off four cocks. Today is busy, a lot of anonymous Johns coming to get off. I can feel my throat coated in cum, almost a numb feeling that I love and crave. The first came almost instantly. His dick was so small there was no need for me to use my hands, I just took it in my throat and suctioned it. He came moments later, not even a knock. I could hear him moaning as if he himself was surprised he was cumming. The other 3 were alright, medium sized. I’m craving a monster black cock, and I’m hoping the next guy delivers.

I’m wearing a mini skirt and heels, with a half shirt with long sleeves. I chose a red wig today, curly hair. I clear my throat, thinking about how much I love the taste of a hot seed. I’m jerking my sissy clit through the thong I wear, edging myself as I wait for the next cock to arrive. My boy pussy is on fire, its been a while since I’ve been fucked and I am craving it so bad. My mind wanders off to my time in prison and memories begin to rush into my head. I wish I had more courage to be a woman on the outside, in prison it was so much easier, I was accepted as a woman. Here in the real world, things can be different.

I hear the door open and another man has entered the opposite side of the glory hole. My sissy clit pulses as I begin to get excited, I think he is black… Yes! He is! And he’s tall! You know what that means…. I hear the unbuckle of a belt and the sound of a soft cock being flopped out of a zipper. The dick that comes through the hole looks… magnificent. It's long, about 10 inches, and thick as a tree trunk. I stop for a second… Is this cock familiar? I tell myself no and snap out of it. A lot of cocks look the same.

My boy pussy twitches as I reposition myself to get ready to take it in my throat. I slurp it into my mouth as I hear a “Yeahhhh” from the other side. Again, a familiar voice. Am I going crazy? I have an idea of who I am thinking of but there's no way. I begin bobbing up and down on the big black dick like a good girl and can feel it grow hard as a rock instantly. I begin using my hands to stroke the shaft. Thick veins begin breathing around the cock as the man thrusts in and out of the hole, in and out of my throat. All I can keep thinking of is two things: do I know this man? And also: I need to get fucked and this would be the cock to do it.

“Yeahhh gimme that neck,” the man says, moaning. I begin twirling my tongue around the head of his cock as I stroke in my trademarked swirl, you can hear the wet friction of my hands as I work the big black cock. Suddenly, the thrusting stops, and so does his moaning. The next thing he says makes me stop dead and freeze.

“Clarissa? That you?”

*******

After Dixie serviced the gang in the showers I could think of nothing but wanting to be a woman. For Devon, and for the gang. I had always been one to rise to a challenge, and one had presented itself to me. I began waking Devon up with a blowjob every morning, and I could tell I was getting better at it. The time it took for him to cum began getting shorter and shorter. It was like I couldn’t get enough of the taste of his salty cum, and my throat begged for it every morning and throughout the day. I would ask occasionally to cum, but he wouldn’t let me. It made me frustrated but it also kept me in a state of constant horniness, constantly wet. I began wondering what it would be like to get fucked, and I would ask Devon to fuck me. He would tell me: “You not ready, you not a full woman yet. I only fuck women.” He would have me suck his balls for hours on end though, which was really hot. He had gigantic black balls and I would soak them in my mouth while he read or slept. I would walk around our cell trying to bend over near him or stick my ass out, hoping he would catch a glance and want to fuck me. A week passed, and then another. Devon had Dixie begin to give me feminine training sessions at rec time. We would go to the library in the back section and she would give me pointers on how to act, talk, and walk like a woman. My hair began to grow out a bit, but it was still a work in progress. Another week passed. The gang would look at me longingly. I could tell they wanted a taste. Devon also had me start taking hormones, one pill a day. I didn’t feel much different, but my voice definitely started to get a little higher. I was already hairless and curvy but Dixie told me I would start to feel different after a month. I would walk with Devon wherever he went, clad on his arm. I was his property. The rest of the jail, and even some of the guards would look on in jealousy at his prized possession. I think they could tell I was getting feminized even more.

One day in the library, I was practicing how to walk like a woman with Dixie in one of her feminization sessions.

“Okay girl, from the top!” Dixie said, with a cute wink, propping her legs like a stallion and turning, walking in a straight line, feet almost crossing one another, her ass shaking from one side to the other as she walked. It was like watching a goddess, her ass hanging out of the back of her short shorts. She reached the end and turned, one hand on her hips, smiling and winking. I could see her tiny dick poking through the booty shorts.

“Now your turn Clarissa!” she said as I gulped. I had been practicing but I was nowhere near the flow Dixie had, the gracefulness and femininity she exuded. I stood up and started walking, one foot crossing the other. I could feel my ass swaying as I walked.

“Yes girl!” Dixie cheered, clapping her hands lightly. Suddenly, I stumbled and broke my flow.

“Dammnit!” I yelled.

“Clarissa, don’t worry about it, let's try again.”

“I’m wearing this jumpsuit, how am I supposed to feel feminine?” I said as I looked down at my baggy jumpsuit.

“Devon says you aren’t ready to wear booty shorts yet… what he says goes.”

I scoffed, frustrated. Dixie could notice this.

“One second, here-”

Dixie took off her shirt, I could see her tiny bee sting breasts. She looked like a petite woman. She then slid off her booty shorts, wearing a pair of pink panties underneath. Despite the tiny bulge in her crotch, she truly looked like a woman. I was stunned, and jealous. She handed me the booty shorts and cut shirt.

“Let's trade.”

“You sure?”

“Yeah, just while we are here. I want you to feel like the woman I know you will become.”

I took the shorts and shirt and stripped off my baggy jumpsuit, Dixie put it on but left the front open, she still looked like a woman. She looked at me standing there naked.

“Yeah. You're gonna be a better woman than me Clarissa, look at your curves!”

I took a look at myself and was surprised to see what she meant. My hips were wide and my ass fat. I had perky bee stings myself, a little more voluptuous than her. I hid my tiny cock as I put on the booty shorts. They were a little tight on me.

“Damn Clarissa you got a fat ass.. Look at that thing!”

I looked behind me and she wasn’t wrong. My thick white bubble looked so sexy in the shorts! So round and juicy, I wiggled my waist and watched my ass shake in the short shorts. I had been wearing the baggy jumpsuit for so long I didn’t realize how nice of an ass I was getting. The hormones were definitely doing something. I slipped the shirt on and it was also tight.

“OMG Clarissa, your chest looks amazing!” Dixie cried. My breasts were small but perky in the tight shirt. I could see my nipples through it. I turned and caught myself in the reflection and was stunned. Staring back was a curvy sissy, me. Nice thick hairless legs, juicy thighs, a round jiggly ass, tiny waist and two decently sized breasts. Not huge breasts, but big enough to trick my mind into thinking I was staring at a woman. Plus, my hair getting slightly longer helped. I turned slightly and did a stallion stance, one leg lifted slightly and oh my god I looked sexy! It filled me with confidence.

“Girl you look delicious,” Dixie said, and I could see her slightly rubbing between her legs. “Now walk, give me your best.”

Filled with confidence, I turned and tried the walk again. One foot in front of the other, slightly crossing my legs as I walked. This time, I was actually doing it! I could feel my ass and hips sway and jiggle as I walked. I reached the end of the walk and turned, striking a stallion pose, hand on my waist, smiling at Dixie. Dixie looked mesmerized, and I could see she was rubbing her boy clit through the jumpsuit.

“Wow Clarissa… that was hot, even for me…”

I blushed, I could tell Dixie was turned on. I had never thought of her like that but knowing she was turned on turned me on a little bit too. I suddenly thought about sucking a cock on my knees next to her and felt my tiny clit begin to throb. I hoped that one day we could do things together and possibly make out. Lesbians of sorts… My cheeks had become inflamed. Suddenly I noticed through the bookshelf a familiar face… The guard who had been eyeing me my whole time here. He was watching me. I looked down and could see through the lower shelf he was stroking his cock. It had been a while since I had seen a white cock. I stared at it for a second but then looked away, pretending I didn’t notice him watching. I wanted all eyes on me in this sissy outfit. I wanted to be a woman. I turned and did the walk again, and out of the side of my eye could see the guard continue to stroke himself. It was a little creepy, but it turned me on! I was starting to really get horny thinking about the men here wanting me. I finished the walk, but this time, I bent over and popped my ass out, holding it for a second and shaking it before standing back up. I looked back and the guard was gone. I felt a little disappointed. Hmm. Guess he had to go somewhere else.

“One more time for me Clarissa,” Dixie said, still rubbing her crotch. I could tell she was turned on. “I hope they make us have a threesome soon… I want to watch you in action. Me and you could make the entire gang cum easy.”

“That would be hot,” I said. My tiny cock was hard, poking through the short shorts. I did the walk one last time, nailing it perfectly. As I turned and struck a pose, I looked back, Dixie had stopped rubbing her boy clit. Behind her stood Devon, and he was stroking his massive cock looking at me. Dixie spoke quickly.

“Sorry Daddy, Clarissa wanted to try on my clothes-”

“Shut up bitch.” Dixie went silent. Devon kept stroking his cock as he looked at me, and my sissy dick pulsed with pleasure during it.

“Damn Clarissa, you lookin real good. Almost like a woman. You makin good progress.” He turned to Dixie. “Dixie get yo ass back to Shaun’s cell and get some new clothes on, Clarissa keeping these.”

“Yes Daddy!” Dixie said as she got up, gave Devon a kiss, and left the back of the library. She smiled at me and winked on her way out as if to say “Good job”.

Devon, still stroking his dick, smiled at me.

“You like what you see, Daddy?” I said, trying to sound as feminine as I could. I was getting more confident.

“Yeah bitch I do. Now walk towards me,” Devon commanded. I didn’t hesitate. I was ready. I strutted over as best as I could, feeling my ass sway and thighs jiggle as I walked. When I reached Devon, he towered over me, almost seven feet tall. He looked down on me like the Daddy he was, checking out my body in the short shorts and low cut shirt. I was almost breathless, all I could smell was his manliness. I went on my tippy toes and tried to kiss his big lips, but he smacked me across the face suddenly, almost making me spin.

“You looking like a female, but you ain’t there yet. You got some work to do.”

I held my face, almost in tears, feeling horrible about myself. Devon came up and wrapped an arm around me.

“I didn’t say you are doing a bad job, but you ain’t there yet. I only kiss women, and you not a woman… not yet.”

I felt another burst of needing to be Devon’s woman, I wanted him to accept me like he accepted Dixie.

“Should we go back?” I said, looking at Devon.

“Not yet. I wanna cum on that ass.” Devon then lifted me and placed me on one of the reading tables. “On all fours, ass up, back arched,” he commanded, and I did just that. My face on the wood surface of the table, I lifted my ass and arched my back, slightly wiggling my ass. He continued to stroke his meat as he towered over me. I could hear the friction of his hand on his dick.

“Yeah…. This ass baby… So fat… Can’t wait to fuck you,” Devon said as he slapped his cock on my ass and rubbed it all over, on top then between my legs. He was rock hard now. My tiny dick throbbed and my ass pussy ached.

“I want it Daddy, please, I need to cum.”

“I bet you do. And you will soon if you're a good girl.” I could hear Devon stroking over my ass, and the tip of his massive meat pressed firmly against my boy pussy, his cock pulsing. I had never felt so hot before; I could see a little wet spot forming from my precum on the tight short shorts. Everything in my body ached to cum. I wiggled my ass lightly against his cock head as Devon began to moan louder. He grabbed my ass with his other hand and squeezed. Just one hand could grab the entirety of one of my ass cheeks.

“Oh yeahhh,” Devon moaned, and I could feel warm wetness through my booty shorts, right on my ass cheek. Devon was unloading his cock onto my ass. Electricity shot between my legs, and I almost came hands free just from Dixie’s tight shorts. Devon finished and put his cock back inside his jumpsuit. A loud buzz rang out.

“INMATES RETURN TO YOUR CELLS, REC TIME IS OVER”

“Get up bitch. Let's go.”

I got up, Devon’s warm seed all over my ass cheek, forming a huge wet spot on the ass of my shorts. It was so much! I felt slightly sad that it wasn’t in my throat. We began walking out of the library. I looked behind the bookshelf the guard had been peeping from and saw on the floor a puddle of cum. He must have busted a nut and then left. It made me feel super sexy.

When we got to the edge of the library, Devon turned to me. “I want you to walk like you were walking in there.”

“Yes Daddy,” I said without pause. I took a deep breath. We walked out of the library and I realized this would be the first time I was walking through the prison in anything but the baggy jumpsuit. As I walked, one foot crossing in front of the other, I turned heads, literally. My ass swayed side to side as I went. Almost every prisoner we walked by turned and gawked at me as I clung to Devon's arm. I was his property, what he said was law. Even most of the guards did a double take, probably thinking I was a real woman. I also had a large wet stain on my ass cheek, clear to most that it was Devon’s seed.

I couldn’t wait to grow my hair out longer and start wearing makeup, I couldn’t wait to be a woman.

That night I sucked off Devon three times in a row. I could get him to cum in less than three minutes, and could feel my skills getting better. The entire time he would grab at my ass and thighs, and play with my nipples. After, we lay next to each other. Devon, almost asleep, muttered, “Soon you gonna suck off my right hand man, Lex. Ima slowly start letting the gang get a taste of you.”

“Yes Daddy.”

“Goodnight bitch.”

“Goodnight Daddy”

To Be Continued :)

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