Bryan walked away for a moment and left me standing in the shower. I dried off like he told me to and sat down on a three-legged stool. Only a few minutes had gone by when he came back through the door. My massaging had me relaxed and content, but the sudden loud jerking of the door startled me. Bryan carried a box over and put it down on the desk with a thud.
"The warden wants you to wear this," he said. "You won't always have to wear this when he summons you, but tonight he's in a mood." He pulled out a pair of fishnet stockings, a garter belt, a pair of crotchless thong panties, and a long, blonde, full-bodied wig. I'll be honest; I loved where this was going.
"Is that all?" I asked, eager to hear the word "No."
"No, it's not," he said. He pulled out a pair of six-inch heels, black like the outfit, and I could only assume they were my size. The warden didn't seem like a man who would cut corners. He wanted me a certain way, and he was going to have me.
"Try all of these on. We have your measurements, so it should all be the right sizes. You will also be wearing these fake eyelashes, this red lipstick, and some other makeup." He pulled everything out of the box and put it on the table. My eyes lit up at the prospect of dressing up as a woman. I had tried cross-dressing in the past, but never as elaborate as all of this. I was excited to see what I'd look like as a sissy slut.
Before I had gone to prison that very morning, I took it upon myself to shave every inch of my body. I figured that if I was going to run into someone who was interested in me early on, I wanted to be smooth for him. I don't know why I figured my mystery dominator would want a smooth body. For all I knew he could have been interested in beefy, hairy men. In any case, I lucked out. The warden would no doubt be pleased with my smooth, raw ass.
I slipped the stockings on slowly for Bryan. He watched me as he rubbed his cock through his pants. He was already getting hard again, and the pumping he did still hadn't worn off. I loved watching that muscular beast of a man stare at me like a piece of meat. My cock was growing itself, and I bit my lip staring into his eyes from across the room.
"Can I help you while I get dressed, daddy?" I said to him. "You look like you could use a wet mouth."
"Keep getting dressed and I'll think about it," he said. He unzipped his pants and flopped his big red cock out. It was trying to stand strong under its own weight, but that thing was struggling. It bounced around as blood pumped into it, and Bryan just kept staring at me while my mouth watered.
"Yes, daddy. Whatever you say." God, I wanted his cock again so badly. I knew he had another load in his big balls for me. I would just have to wait.
With the stockings already on, I slipped on the panties and the garter belt. I hooked the clasps to the top of my fishnets and slipped my dick through the hole in the front of the panties. It certainly stood out quite a bit, but I figured the warden would probably want it that way. He had all my measurements, I'm sure he knew I was hung as well. I turned around and looked at my ass in the mirror. Goddamn I looked good. My bubble ass, freshly shaved, looked even more defined in that jet-black thong. The stockings came up and framed the bottom of my cheeks perfectly. I wiggled it back and forth, bent over and bit my lip. Bryan let out a grunt. He had begun stroking his cock again, and he was growing as big and strong as ever. I looked over at him and smiled. He just stared with those cold, lustful eyes.
I walked over to the table and picked up the heels. I was so excited to see how these looked. I slipped them on in the most feminine fashion that I could. They were incredibly sexy. I would have bought them for my ex-girlfriend if I had seen them. The warden had good taste, or so it appeared. I sat at the mirror and put on my lashes and lipstick. I was no pro, but I did a pretty good job. Then I moved to the blush and foundation. I did a good job with that too. I looked at myself in the mirror and blew myself a kiss with a wink. I was really looking like a woman from the neck up. When I slid the wig on, I was blown away. I looked damn sexy, and the wig was a perfect cherry on this slut sundae I was making.
Bryan walked over with his now rock hard cock in hand. He was silent, but he didn't have to say a word. I took his steaming hot cock in my mouth. Sitting on that stool while I sucked Bryan's perfect puffed up dick, dressed in a full sissy outfit, I fell to another level of shame and degradation. It excited me, though, so I didn't care. That was all a part of the rush; to see how much of a whore I could be. It wasn't hard to remember that not long ago I was caught covered with piss and cum with the semen of five black convicts dripping from my open asshole. Dressing like a sissy slut in prison certainly couldn't beat that.
Bryan moaned as I worked my tongue around his red-hot head. "Look at me," he said. I listened. "Open your mouth," he continued. I listened. He took two white pills and threw them in my mouth. He handed me a bottle of water and told me to swallow. I listened. "Those are vicodin. The warden wants you drugged and woozy tonight. He thinks you will be a more willing participant in his antics if you can't feel as much pain as you normally would. Don't worry; he won't leave any cuts or anything permanent on you."
"No need to explain. I love vicodin. I can't wait until they kick in." I sucked his meat back into my mouth with a slurp and worked him hard with my hands and mouth. He let out a moan like a bear and threw his head back. I pushed his cock into my throat and held him there for a while. I gagged a few times before pulling him out and slapping my face with his dick. I was going to have to redo my makeup before this was over. My red lipstick was smeared already, and the mascara was going to run soon enough from the tears. I sucked him in again and bobbed up and down on him. He moaned louder and louder until he jerked his hips forward, ramming his beautiful dick down my throat. He filled my esophagus with his second thick load before pulling back and filling my mouth. I coughed a big cum bubble up, sucked it off my lips, and swallowed it all with a smile on my face.
"Thank you so much for your second load, sir," I said. "Is there anything else you need?"
"No," he said. "Just redo your makeup and get ready to go see the warden. I can see you have the sissy act down already. Keep it up. He'll like that."
"Yes, sir." I turned back to the mirror, grabbed a wet towel that Bryan handed me, and got my makeup back in order. It looked even better the second time. I was finally ready to see the warden.
Bryan stood me up and smacked me on my ass. The heels made my legs look even longer. They really brought my femininity out. I got a look at the entire image of my cross-dressed body and giggled with glee. He walked me out of the room and took me down a secluded hallway. The clicking and thudding of my heels echoed off the walls. It took me a few hundred feet to get used to the shoes, but soon I had it down. He opened up a door at the end of the hallway and instructed me through it. Suddenly I was standing in a huge room surrounded by prison cells and prisoners. I stopped for a moment, horrified and embarrassed. All of these men were about to see me in full dress, makeup and all. This may not have been the best way for me to show up to prison, but I was in it for the long haul, so I bit the bullet and walked on.
The room erupted in laughter, hoots and hollers, and the sound of hands, books and all sorts of things hitting the heavy steel bars holding back these savage men. I was happy for the bars. These men would have probably stormed out of their cells and raped me a hundred times before anybody could stop them. Some of them were big, burly men; some of them were smaller and less so. I looked at the wall of cell doors and noticed that plenty of them had their cocks in their hands. They swung them around with vigor as they shouted about my ass and what they wanted to do to me. My mouth was watering at some of them. I couldn't help it. Plenty of them were good-looking men with big cocks. The slut in me wanted their meat, but tonight I was the warden's, so I kept my mouth shut and walked on.
"Look at this little sissy faggot! I can't wait to catch you in the shower," one man yelled. I giggled at the prospect. The showers were something I looked forward to a great deal.
"Come suck the cum outta my balls, whore," another man shouted. "I got a ten-day load for you!" Little did he know, I already had a belly full of cum. Or maybe he did know, and that's why he yelled it. Surely I wasn't the first person to be fucked so relentlessly by my escort, Bryan. The rumors were probably already circulating.
"The warden's got a new toy, boys! Keep your cocks ready, it's gonna be a fun week," a third man yelled. He held his huge cock in his hand and stroked it while he yelled. I wasn't sure what he meant by "fun week," but I relished the thought. I hope he gets a piece of me soon. He had that big, bald, monster-of-a-man look to him. My mouth was watering more now, and my cock had begun to stand tall through the crotchless panties. The prisoners noticed and made sure to announce it to each other.
