The Warden

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.

At the end of the hall Bryan opened another door and pushed me through. I climbed a huge set of stairs and we stopped at the door at the top. The word "Warden" was plastered to the big wooden door, and my heart began to race. This was the moment that Bryan had been preparing me for all night - a preparation that including sodomy, penis pumps, nightsticks, relentless fucking, and not one, but two big loads of cum from his balls. The warden had ordered it all (except that last blowjob, I think Bryan took that for himself), and this was the man I was about to meet. The door swung open and we walked inside.

The office was incredibly lavish compared to the rest of the prison. I suppose it made sense. Clearly this warden ruled with no question to his power. He had me fucked by a guard and prepared for his pleasure the moment I arrived. A fire was roaring in the fire place, an entire wall of books loomed over one side of the room, a beautiful mahogany desk with a gold-plated lamp sat in front of a huge leather chair, and every other cliché addition you could make to a rich man's study decorated the room. The warden even spun around in his desk chair with a cigarette in a long-stem holder. He wore a robe and nothing else. He was muscly and good-looking, but a bit older than Bryan. He had salt and pepper hair, and an incredibly hairy body. I was turned on already, but after seeing that the warden wasn't some fat slob or hideous chud, a lot of my nerves left me, and I relaxed in my heels and garter.

"Thank you, Bryan," the warden said. "You may leave her."

"Her." That was strange, but I liked it. Tonight was going to be one hell of a fetishist's dream, I could tell that already. Bryan turned and left without a word. I stood there looking at the man splitting me open with his eyes. He stood up and put the cigarette out. His big cock fell through the split in his robe. I licked my lips, but I dare not move. I was going to let him instruct me in everything.

"I've heard a lot about you," he said. "I've been paying close attention to your case. I even went out of my way to have you brought to this prison in particular. I'm sure you noticed it happens to be out of the state you were arrested in. That's no coincidence. While you're here, there are rules to follow. I'm sure Bryan already informed you of those." I nodded. "You will address me as Sir, Warden, or Daddy. When I call for you, you will drop everything, including any cocks in your ass or mouth, and come to my office. I don't care who is inside of you; you pull them out and leave. You shouldn't get any trouble in that regard. The guards will take care of your escorts. I had you dressed tonight because I love submissive sluts, and since we can't get female prisoners, this is the next best thing to having a woman to fuck with. I am loyal to my wife, so I don't sleep with women other than her, but she doesn't know a thing about what goes on here at my prison, and she never will."

I nodded again. "Yes, sir."

"Now," he continued, "to start, come lay on the rug in front of the fire. While you're here tonight you will make your voice higher, and make yourself as feminine as possible. Everything you do should be girly. You're my sissy slut, and you will put on the act. Do you understand?"

"Yes, daddy," I said with seductive eyes. The eyelashes and makeup certainly made it more effective. I strolled over to the rug in my most womanly walk, bouncing my butt back and forth while I looked into his eyes. He smiled and bit his lip. I noticed a rush of blood pump into his limp dick, making it bounce once or twice. I giggled and made my way. As I lay down, I poked my ass up at him and wiggled it around. "What's next, daddy?"

"Mmm. You look good. Put on a show for me, Samantha."

"Is that my name tonight, daddy?"

"Yes it is. That will be your sissy name forever, so get used to it. Any time you are dressed, you are Samantha."

"Yes, sir!" He pulled a chair over and put it down, his big robe opening wide with his stride, revealing his hairy, muscular body. I was so horny already, and the vicodin was kicking in, so I had all sorts of feelings rushing through my body. I wanted to please my master as I'd already done once tonight, so I gave it my all. I struck poses, smacked my round booty, spread my cheeks, and talked dirty to him.

"Give me a dance," he ordered. I gladly entertained the idea for him. I had never done a strip tease, but I was happy to try tonight. I assumed I would be pushing all sorts of boundaries today. I walked over to him in my outfit, my now hard dick showing clearly, bouncing around. The image must have been hot to him, because he bit his lip again and stroked his cock a few times. I bent over in front of him and shook my ass like my girlfriend always used to do for me. I danced a little bit with it before pushing it against his face. He took a big bite out of my cheek and smacked the other.

"Oh, daddy," I said in my most girlish voice. I continued my dance as he put his hands all over me. My dick was rock hard now, and he grabbed it and squeezed.

"You have a nice cock. I hope you know I'll be playing with this tonight as well. You may be fully dressed, but you'll find soon that I have my own personal tastes for fetishes. I like my cross-dressers with big cocks, not little embarrassments." Without another word he took my dick in his mouth and squeezed my big ass cheeks. My eyes rolled in the back of my head with ecstasy. He sucked me so well I thought I might burst already, but the vicodin came on in a wave and the sensation was dulled. He kept sucking on me, and I moaned like a girl for him. What an interesting concept that was; having my dick sucked while I moan like a girl.

Once he had his fill, he let my cock fall from his lips and picked up his own big cock. I took the hint and got down on my knees, my big heels sticking out from under my round butt as I squatted like a woman in front of him. I took his hairy dick into my mouth and teased him a bit while I looked at him. I batted my lashes at him with his head in between my lips, my tongue flicking the underside of his meat. He moaned and looked back at me. I started to bob my head up and down on him with my tongue still flicking back and forth. He opened up a small bottle of poppers and stuck it under my nose.

"Take three big deep breaths, and don't you dare stop sucking." I did as I was told, and the rush to my head had me spinning. The vicodin and poppers combined put me in such a state. My head was hot and full of filthy thoughts. The heat washed over my body as I swallowed his meat all the way down my throat. He moaned like a beast and threw his head back as I continued to make the swallowing motion with my throat with him inside my neck. I moaned on his dick too, giving him even more of a rush of sensation. As I pulled my head back, his cock slipped out shiny and plopped onto his hairy stomach.

"Holy fuck. Do that again, now," he commanded me. Of course I did it again. I loved doing it, and I had to make sure my first impression was a good one. This man was going to decide how my time in prison was spent. Satisfying his primal urges was the least I could do. Over and over I took him down my throat and hummed on his cock. The noises he made were enough of a reward for the act.

The poppers soon wore off, but the vicodin was hitting me so hard my eyes were getting heavy. I kept forgetting that I was in total dress, but every time I remembered, my cock twitched with excitement while my asshole puckered. I knew it would be a fetish I would keep up with after I got out of prison.

After I did my slutty duty with my mouth, the warden stood up and dropped his robe. I sucked his cock back in between my lips a few times before he walked across the room. I dare not move without orders from him, so I sat there licking the slobber off my chin and face.

"Now the real fun begins," he said from behind me. I turned to look at what he meant, and he was absolutely right. The real fun was getting started. He unveiled a fucking machine with one of the biggest dildos I had ever seen. It was about the size of Deyron's big cock, or maybe Bryan's pumped up shlong, but it was big nonetheless. "Come over here and position yourself on your hands and knees in front of it."

I stood up without skipping a beat and walked over to the machine. He powered it on to show me the raw power it had. Unlike any man, this thing was capable of delivering the same length and power in every thrust for as long as I (or the warden) desired. I was excited at the prospect. I got my girly ass down on all fours and poked my butt in the air. He turned a knob on the machine and it slowed to a stop. He grabbed a huge tub of anal lube and grabbed a whole handful of it. He lubed up the machine and tore my panties down. The lube was running down my cheeks and legs in no time. He left everything on but the panties and used the rest of the lube from his hands to shine my asshole up nicely. I was reeling from the opiates, and ready for another popper. I figured I would need one if I were going to take that horse cock in my hole. Sure, Bryan loosened me up, but something that size was going to hurt, no matter how warmed up I was. Like he read my mind, the warden came over with the poppers and held them under my nose while he put his fingers inside my hole. I moaned and giggled, like I knew he loved, and pushed my eager butt back against his knuckles. He had four fingers inside me in no time, and I was feeling full again. I figured he would just put his whole hairy fist inside me, but he didn't. He fucked my hole with his fingers for a while and positioned the dildo at my ass. I was ready for that familiar pressure in my abdomen; the feeling of being displaced from the inside out. I wanted it again. It was becoming an addiction. The head of the dildo slipped in as I pushed back. I slid every inch into my rectum and shouted "Oh, fuck, daddy, I love your big cock in my pussy!"

"That's right, you little cunt. Take that huge mast. You better be ready. I'm turning this thing on."

He slowly turned the knob on the machine and it started to slowly go in and out of me. Every inch, slowly slipping between my cheeks, into my sphincter muscles, testing my limits. The power increased, and so did the speed. Faster, deeper, harder. Before long, the machine was running full bore. The feeling was unbelievable. I had never been fucked so hard before, and with such a huge dildo I was full to bursting. The rumbling of the machine drowned out the sloppy noises, but I could hear my asshole singing.