Becoming a Woman in Prison Ch. 04

Chapter 4

After another week, Devon started letting me wear feminine clothes around the prison. I thought it would be embarrassing but I saw the way the other men looked at me. Like I was a piece of meat. And I liked it. My hair had started to grow out, and it was almost in a cute pixie bob. The hormones were working like a charm and my voice had continued to get higher and my body hair seemed to start thinning out, which I kept trimmed with a razor that Devon gave me. Everytime I looked in the mirror it was as if I was becoming more and more a woman. It was turning me on. Becoming a woman for Devon started to become a thirst that I wanted to quench. I could tell I was getting closer and closer to Devon fucking me by the way he would grab my ass and massage it when I sucked his dick, sometimes with both of his massive hands on each of my ass cheeks. One day, it was around noon and we were hanging in our cell, his boy Lex came over. Lex was not as tall as Devon, but he was very muscly and had big hands. Lex looked at me, his wanting.

"Clarissa this my boy Lex."

"Hi Lex!" I said, trying to sound extra girly. Lex continued looking at me, eying my thick legs which were now shaved and exposed. I could see there was a tent forming in his prison trousers.

"Lex needs to bust a nut, and he been doing extra well with the contraband, so I'm letting him have a taste of you." Devon said. I began to grow excited, but also nervous. Up until this point I had only sucked Devon's dick, and it had become a point of comfort for me. But I knew better than to let it show.

"Yes Daddy, right here?"

"Yeah bitch, right here. Ima watch you do it."

Lex stepped up, lifting up his shirt slightly and leaning his pelvis forward, his tent pitched in his jumpsuit. He looked at me licking his lips. I didn't hesitate, hopping off of the bed and getting on my knees in front of him and grabbing his shaft through his pants. It was long and skinny, not quite as girthy as Devon, who had an absolute trunk of a dick. But it still turned me on, especially seeing how Lex was looking at me. Like I was a piece of meat.

"You want some head handsome?" I asked, taking his cock out of his pants. It swung up and out as soon as I lowered the jumpsuit. Lex's cock stared at me, rock hard. I wrapped my hands around it and kissed the tip, looking at Lex in the eyes.

"Yeah Bitch I do" he said, thrusting the tip forward and into my mouth. I began working on his dick, swallowing it and using both of my hands to stroke it in a circular motion. I spit on both hands and made my workspace nice and wet, easier to begin to deepthroat.

"God damn D... you weren't lying.. This mouth is real nice."

"Hell yeah it is, I'm a man of my word. She comin along nicely."

I turned a little to see Devon on the bed, watching me suck Lex's cock. He was rubbing his crotch, which was growing bigger. Lex began thrusting forward and back, moaning and groaning. I could feel my sissy clit pressed against my short shorts, wanting to orgasm. Suddenly I felt Devon's hand on my ass, he squeezed and spread my cheeks, feeling my boy hole with his fingers. It ran shocks through my body as I continued sucking on Lex.

"Yeah bitch... yeah suck that cock you slut," Lex moaned. "You like that cock?"

I couldn't speak but replied with a "Mnnnff-Hmmm" as I looked up at Lex. Suddenly I felt his cock become rock hard and his thrusts became faster. I tightened my grip with both hands and started going as deep as I could go. Suddenly he tensed up.

"Ahhhh fuckkkkk bitchhhhh!" Lex screamed as he dug his cock fully into my throat and released. I felt ropes of cum repeatedly jetting down my throat as Lex slowed down his thrusts. I swallowed every drop. Lex finally stopped, panting, trying to catch his breath. His dick started to soften as it plopped out of my mouth.

"Did you like that sir?" I asked, looking up at Lex. He looked down at me smiling.

"Hell yeah he liked that bitch, stop asking dumb questions." Devon said as he pulled me back onto the bed. He turned to Lex.

"Now you keep bringing in profit like that and there's more where that came from."

Devon and Lex dapped each other and Lex pulled up his pants, turning and exiting the cell. I lay down, still tasting Lex's cum in my throat, coating it. I could see Devon was hard so I crawled up to him on the bed, putting one of my small hands on his cock. My tiny clit throbbed as I said this, wanting more dick. I got on all fours, ass up in the air.

"You want me to suck you too, Daddy?" I looked up at him, trying to be a feminine as possible.

"Nah bitch." Devon said, and I could feel tears well up in my eyes. The hormones had been making me more emotional lately, like a real woman.

"Why not??" I said, trying to not cry.

"Because tonight I'm gonna fuck you." Devon said, looking into my eyes. My tiny cock sprang back up in my pants as he said this. Devon reached out and grabbed my ass in the air, massaging both cheeks. Even though my ass was thick and fat, it felt tiny in Devon's massive hands.

"Really???" I exclaimed, barely containing my excitement. I swayed my ass as Devon continued feeling me up, I could feel his fingers caressing my boy pussy through my short shorts.

"Yeah. You ready, bitch. Well, almost ready. Dixie is gonna help you shower up and put some make-up on. Make sure you one hundred percent a woman for tonight."

***********

About an hour later, Dixie came by my cell and we went to the showers together. Devon had made sure they were clear so we could have our privacy, he had that sort of power in the prison. Once in the showers, Dixie told me to strip naked, and she did the same. Watching her strip was hot, she took off her short shorts and had a pair of light blue panties underneath. Her ass was way smaller than mine but it was cute and tight, and still had a little jiggle when she took her panties off, revealing her tiny boy-clit, which bounced up when she removed her panties. Her breasts were bigger than mine, probably because mine were still developing with the hormones. She took off her half-shirt and her breasts popped out. Seeing her fully naked reminded me of watching her get pounded by the gang in all of her holes. My sissy clit was hard as a rock, my mind wrapped up in hot memories-

"Clarissa? Clarissa? You with me?" Dixie's voice cut through my thoughts like a hot knife through butter. I snapped out of it.

"Yeah, sorry about that. I was just... er..."

"Don't worry honey, I get it. Thinking about sexy stuff I bet." she said, nodding toward the tiny bulge in my short shorts. "Now get naked, we gotta get you ready to have your cherry popped."

I smiled as I began to strip, my fat ass popping out of my short shorts as I kicked them off. I was surprised at how hairless my legs were, the hormones were really working. My waist had become smaller but my ass had become plump and my hips wide. I caressed my hairless stomach before taking off my torn half-shirt. Holding my small bee-sting breasts I wished they were bigger. However they were still big enough to squeeze.

"Don't worry girl, give it time." Dixie said, winking at me. "Now get over here into the water."

Obeying, I stepped into the hot steamy water with Dixie, my tiny clit dick still hard as a rock. Holding a razor, Dixie began looking around my body for little patches of hair, shaving them as she went.

"Hmmm, you are doing well Clarissa, not too much wild hair anymore. That's great!" she said as I could feel her shave a small patch of hair on my back. I turned to look at her curvy body, no hair in sight. I wanted to be like that.

"You are so sexy Dixie, I want to be like you..." I said, and Dixie could hear the disappointment in my voice. She slapped my ass, turning me around.

"You will be Clarissa! And even better than me... Look at your hair, it's so gorgeous! In no time you will be indistinguishable from a woman, ya know, except your boy clit, but that's okay. The men won't admit it but they like a sissy boy clit hanging from between your legs while you are getting fucked, trust me! Now spread your legs, I am going to shave your sissy pussy."

I spread my legs and Dixie got on her knees and began shaving between my legs, particularly my asshole, or boy pussy as I had come to call it. It felt awkward, I had never had anyone fuck me before. I had tried with my fingers a few times but never gotten too deep.

"Does it hurt?" I asked.

"What, getting fucked?" Dixie replied, still underneath me.

"Yeah..."

"Kind of, at first. Then it feels reeeaaaaallly good. Trust me. And that painful part in the beginning, you come to love that too, getting stretched open. Especially when you hear the guy enjoying the feeling, that's the best part."

I could imagine what she meant, pleasing Devon was almost the best part of sucking his dick. Being his bitch and submitting to him. When he moaned with pleasure, it made my sissy clit stand up. I still hadn't cum this whole time, so I spent most of my time being hot and bothered. Dixie could see this.

"He still hasn't let you orgasm has he?"

"Nope... I don't know how much more I can take... It's driving me crazy."

Dixie finished shaving my ass and gave me another spank.

"Don't worry, you'll cum soon enough Clarissa, gotta be patient. Okay, you're all shaved, and looking good. Now we need to make sure you are extra clean down there."

Dixie grabbed a plastic bottle and filled it up at the shower head and then turned to me.

"Okay, you ever use a douche before?" she asked, holding the filled up water bottle out to me.

"Er, no...?" I answered, confused.

"You have to use this to clean your boy-pussy. Like this-" Dixie motioned with the bottle as if she was putting the tip in her ass-pussy, and gave the water bottle a firm squeeze. I could see the water shoot out of the tip. It began to make sense to me, this would be to make my ass-pussy extra clean for Devon. I took the water bottle and awkwardly tried to put it in my ass. Dixie watched, then laughed.

"Probably better to squat, girl." she said, holding back more laughter.

My cheeks red, I squatted with the water bottle and put the tip into my ass. I had never felt anything enter my asshole, so this was a weird feeling. Once the tip was lodged, I gave the water bottle a firm squeeze, and my eyes rolled back into my head as I felt a gush of warm water surge up into my ass-pussy, then drain out. I couldn't help but let out a high pitched "uuuhhhhnhhhh". Dixie stood there smiling at me.

"Yeah... you're gonna love getting fucked." she said. I looked down and could see her boy-clit getting hard. "Now do it over and over until you are squeaky clean, girl."

She didn't have to tell me twice. I began cleaning myself out over and over, loving the feeling of the warm water gushing up inside of me.

"Okay, that should do it." Dixie said as she turned off the water. I was still squatting, wanting to push this bottle deeper inside me. I stood up, and felt the last of the warm water pouring out of my ass-pussy.

"Now we need to get you dolled up, girl!" Dixie said, grabbing a small make-up bag she had stashed on the shower bench. For the next twenty minutes Dixie used different powders, concealers, and lipstick on my face as I sat there like a good girl naked on the shower bench. Dixie worked like an artist.

"Next I'll teach you how to do all of this yourself, but for now I want to focus on making you look as sexy as possible for Devon." she said as she applied more powder to my cheeks. I began getting nervous, hoping that the make--up looked good. What if I wasn't "womanly" enough for Devon? I don't think I could take the rejection. Dixie then moved on to my hair, brushing it and applying an ointment, she began styling it.

"Godddddddd I wish I had your hair! It's almost long enough for pigtails" she said as she styled it. "And that should do it...." Dixie said, looking at my face and hair, debating if anything else was needed. I was nervous as hell, wanting to see the end result.

"Can I see??" I asked, practically clutching for her tiny mirror.

"Not yet, girl. Let's get you dressed." Dixie said as she grabbed a small backpack and handed me some clothes. As I looked at the clothes they took my breath away, these weren't just simple short shorts and half-shirts. I proceeded to get dressed, squeezing into the outfit. When I was ready, I turned around to Dixie, who looked at me with a wide smile.

"Now you are ready to see... look-" she held up the portable mirror which was enough to see most of my full body and face. I looked and saw.... A woman.