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.
