A Sissy's New Daddy Ch. 08

By the time I was pulled from the trunk, my face looked like a day old glazed donut. George pushed me into the hands of two waiting guards. One of them, Kenneth, held me at arms length "Jesus, he smells like a whore house."

"That's because it is a whore house, a walking talking, fuck toy." Mitchell said as he curled his fingers into my hair and pulled it. "George I gotta say I owe you one. You really came through this time."

"I told you I could get you the cunt from the video." George said as he closed his trunk and started towards the front.

"We are even George, 5 hours with this little tart will settle what you owe." Mitchell said as he started to push me towards the gate.

"Check your paperwork Mitch, it isn't five hours. Its five days." George called out as he climbed into the car and fired it up.

Mitchell stopped moving and looked back to George with the biggest smile the man had ever shown outside of his private dungeon. Kenneth kept pulling not realizing that Mitchell had stopped. "Come on Mitch, let's get this whore washed up."

"Not yet, she's got an appointment with Harrold first." Mitchell said as he pulled me by my hair.

"Hell no, I don't care how much that freak is worth. I ain't going near that cell." Kenneth said as he released Billie and started for the gate.

Mitchell didn't say anything as he drug me to a small cinderblock building far from the main entrance. "Do you want to die tonight?" Mitchell asked as he pressed me into the buildings steel door.

I shook my head no and squeezed my eyes shut tight. "Good we are going to get in here and I am going to tie you to the bars. Harrold has paid me for an hour of your time. You let him do what he wants and don't fight him and I will make the next week of your life a little easier. Embarrass me and I will rent you out to the sickest perverts I can find in this place. And when I have run out of time. Well then I am going to turn you over to the gangs. Honestly you are going to spend your time here someones bitch no matter what. How you spend the next hour decides how brutal your owner is."

I nodded quickly mumbling I would do as I was told. Mitchell pulled me back from the door and opened it up. I had not yet been in prison but I was pretty sure that Harrold's cell block was not the norm. The walls were painted a deep red and the bars to the cells were polished to a shine. There were six cells in the building and only one of them was being used. There was a desk by the door with an older guard dozing quietly behind it. The cell furthest from the door. Had a sheet hanging on the outside of it.

Death metal was playing from a radio somewhere but it was low enough that it was barely audible. Mitchell stood next to the desk looking Billie up and down. The longer he looked the larger the bulge in his pants grew. "I can't wait till I get to bury my cock in your slutty little hole."

"I believe I am first in line. My demonic keeper." A voice called out from the back of the cell block

Mitchell bent me over the desk and started towards the back. The building, which was really just one room, wasn't large so I could hear them easily. Mitchel spoke first "Don't forget where you are. Your money buys comfort it doesn't buy freedom. You still do as I say."

I looked over my shoulder trying to get a look Mitchell and the elusive Harrold. "Now Lets be honest, Mitch. The only reason you are here is I want you here. I make a phone call and you get transferred back to that boring woman's prison down south. I got you transferred here. I got you a promotion. I can take all of that away from you."

Harrold slid his hands through the bars and patted Mitchell on the cheek. "Now where is my prize for today?"

Mitchell pulled his cheek away and walked back to the desk. I didn't want to risk standing up until I was told to do it. Mitchell ran his hand down my back until he cupped my ass through my panties. He pushed the panties into the crack of my ass and started to push them into my boipussy. I sucked in a breath and closed my eyes. Taking ahold of the waistband of the cotton panties and pulled them into a painful wedgie. With his hands holding my panties and my hair Mitchell walked me over to Harrold's cell.

I expected a decrepit hunched back man, but instead I found a young man that was the picture of health. I went to a zoo once when I was a kid and they had just gotten a new lion from Africa. It had been captured in the wild. When you looked at it you saw a monster ready to devour you whole and pick its teeth with your relatives. Harrold had that same look. Mitchell unlocked one of the cuffs and attached it to the bars of Harrold's cell. He produced three more pairs of handcuffs and did the same to my other hand and both ankles. Harrold looked annoyed. "How am I supposed to play with my toy, when it is out there and I am in here?"

"After last time, I am not leaving you alone in there. You will get to come out here and then the timer starts. You go to far and I taze you and you lose the toy." Mitchell said as he walked back to the desk and woke the sleeping guard.

"I haven't had a sissy boy in some time. How broken are you?" Harrold asked as he moved right up next to the bars. Slipping his hands through the bars Harrold smiled as he slid his hands into the front of my panties, "I wonder how broken are you. All Sissy boys are broken. Some got broken by their mommies, some by their daddies and some by their first master."

I must have flinched because Harrold seized the unspoken answer. "Master. Ohh when a master breaks a sissy they are a very sad creature. When a Mommy or a Daddy breaks a sissy they will do anything to feel love. But when a master breaks a sissy..."

The cell door popped open and Harrold shuffled out. "A master breaks a sissy and all a sissy knows how to do is survive. I knew a man once hated broken sissy's he said you couldn't hurt them."

"He was a fool. So I ate his brain." Harrold unzipped his prison issued pants and positioned his cock at the entrance of my boipussy. "I was afraid at first that his stupidity would infect me, but I got over it."

With a smooth motion Harrold pushed his cock deep inside me. I buried my face in the bars hoping not to look at him. Of course he wouldn't allow that. Taking a firm grip of my hair Harrold turned my face so that I could see him. "Your face is quite lovely. I love your whore makeup. I haven't gotten to play with a cumdump since they locked me up in here. I will say though it was an even trade. They supply me with young little playthings and I kept their guards well paid."

Harrold leaned in and opening his mouth started to suck the cum from my face. As he sucked and licked the cum from my face Harrold's hands found their way into my bra and began to play with my nipples. Between his cock, his hands, and his tongue I was very stiff and desperate to feel him plowing in and out of my backside. "Please fuck me. Please Harrold I want to feel your cock pump a load into my boipussy."

With a quick jerk Harrold pulled his hands and mouth away from me. "Don't you dare speak that name to me. That sad pathetic name. Maybe I should turn you over to the dogs you disrespectful little trollop."

I was starting to panic, I didn't know if he was an elitist, a racist or he if meant actual dogs. "Please, please sir I am begging you. Please forgive me."

"Shiva, you will call me by my true name. Beg Shiva to fuck you." Harrold said as he sucked my ear into his mouth. He pushed the lobe around with his tongue while bitting down with his teeth

"Please Shiva, Please fuck me. Use my body for your pleasure." I whispered through clinched teeth. "I am yours to play with."

A shiver ran down Harrold's body just before he started pounding away at my backside. The harder he pushed into me the harder I became. I couldn't stop myself from cumming as I felt his cock twitch and spill his seed inside of me. As the last spasm seized his body Harrold fell against me hanging onto my body, he hung there not speaking until he softened and slipped out of me.

"Mitch, an hour isn't enough, I want to fuck him again and I want to fill his mouth with my piss." Harrold said as he reached around and began to fondle my boipenis. "Also how much would it cost to castrate him. I want to put his little sissy cock in a jar her in my cell."

"If you can piss right now then I can let you do that right now for free. All the rest of off limits. I am pretty sure the prison doc would notice if his cock was missing. No matter how small it is." Mitch said as he approached with a tazer in his hand. "Now don't make this difficult Harrold. Climb off of him and get back in his cell."

"I think your next payment will be short Mitch." Harrold said as he uncurled his body from mine and walked back into his cell "I think you are forgetting who is your superior."

"I'll give you a hundred for his panties." Harrold said as he began to message his cock through his pants. He wasn't wearing any underwear and it was wet enough that it was starting to soak through his thin prison issue pants. Mitchell closed the gate to Harrold's cell and clipped the tazer back onto his belt. First he released my ankles and then my hands. I held onto the bars after he released me, I wasn't sure if I could stand on my own.

"I cant sell you his panties. You know the rest of the guys here are a bunch of pansies. I show up with this little tart in just a bra, they will say he isn't girly enough and start bitching." Mitchell took a hold of my panties, giving me a wedgie once again and started to walk me out of the small bulding.

"Oh please with that much cum on him, of course he is a girly whore. He is wearing enough to repopulate a small island." Harrold called out immediately laughing at his own joke.

Mitchell mumbled under his breath as pushed me out into the cold night. I was marched around the outside of the building until we reached a small side door. Mitchell knocked three times, then four times, and then after a long pause he knocked seven times. Kenneth opened the door and let out an audible sigh. Kenneth took my arm and pulled me inside. We passed through a couple of gates and man traps until we got to the showers.

The showers were empty even though the sun was starting to come up. Mitchell pushed me into the showers and using a key turned on the water. "Strip."

I pulled my bra off and rolled my panties down as quickly as I could. Handing them over to Mitchell "Kenny, Make sure this twatboi is nice and clean, I am going to take his clothes"

Mitchell laughed as he waved my bra and panties in the air "and get them cleaned. I gotta meet with the warden over breakfast so I will be a bit. Lock the door when I leave. No inmates get to touch him until we have had our fun."

I didn't wait for any further instruction, I moved under the water and started to wash the day off. A liquid soap dispenser was attached to the wall and I used almost half the bottle. Once I was covered from head to toe I used three fingers to clean my boipussy. The motion brought back pleasant memories, memories that were shattered when Kenneth cleared his throat.

Turning I expected to find him leering at me looking for any excuse to abuse me. Instead I found an embarrsed young man bulging out of his pants. "Do you um, do you need any help?"

Nodding I watched as Kenneth quickly stripped off his uniform and almost bounced into the shower. He took a step and then a wave of hesitation washed over him, pausing he looked back towards the rooms entrance.

"I could use that help." I said drawing his attention back to me. Kenneth smiled and feeling confident again stepped up behind me. My resolve was thrown when he didn't ram his cock right into me. I knew he was hard I could feel it pressing against my thigh. But Kenneth, slipped three fingers inside of me and finished what I had started.

With his free hand Kenneth turned my head so I was facing him and leaned in and kissed me. Men didn't usually kiss me, they fucked me but I wasn't usually good enough to kiss. Kenneth's tongue was warm as it slipped into my mouth and thick. I could only imagine what his cock would feel like inside of me. Reaching my arms back I rubbed my hands over his slick skin and wanted desperately to see Junior again.

As he pulled his fingers out of my backside Kenneth slipped his cock into me, and it felt like his tongue only better. I moaned as he slow pushed himself completely inside of me. He continued to kiss me, and I was ready for him to start pounding into me but he never did. Kenneth slowly pulled out of me and just as his head was about to pop out he slowly pushed back in. I felt every inch of his cock as he slipped back in. I went limp with pleasure and would have fallen over if he hadn't held me against the wall.

With our mouths coupled and his cock inside of me Kenneth used his free hands to fondle my boipenis. On his third thrust inside of me I started to twitch and Kenneth slowed his hands down. On his fifth thrust I felt a twitch form his cock and on the seventh I felt another. Speeding his hands up Kenneth brought me within a breath of cumming and then he speed his pace up and felt him cum pumping his seed into me. I exploded a moment later. Kenneth thrust into me two more times and each time his entire body spasmed.

As Kenneth pulled out of me he gently spun me around and pressed my back into the wall. He pulled me close and we continued to kiss under the warm shower. His cock and my boipenis rubbed together stiffening both of them just a touch. Finally Kenneth pulled away and with an embarrassed smile spoke "We need to get dried off and I need to get dressed."

I toweled off quickly and a need came over me. I stepped to Kenneth and taking the towel from him I dried his body off. The feeling of my terrycloth clad hands stiffened him nicely and my warm mouth did the rest. He tasted clean and smelled clean. I moaned as rubbed my tongue along his shaft. Kenneth put both of his hands on my head and whispered his desire to cum. I bobbed my head up and down until I felt his warm salty cum splash across my tongue. With just his head in my mouth I sucked and stroked until every ounce of his nectar was mine.

Cum swirled around my mouth until Mitchell arrived again. I just couldn't swallow it, the taste was so heavenly. Mitchell tossed me my now clean bra and panties. I had already put the heels back on so I was ready to move pretty quick. Kenneth couldn't look Mitchell in the eye so I did my best to distract him. I bent at the waist as I pulled on my panties. Swallowing the cum in my mouth I asked for his help clasping my bra, and then while he did it I pushed my butt back and rubbed it against his crotch. "Hey Kenneth, why don't you get out of here I think I can handle this one myself."

Kenneth didn't argue or wait he fled from the room as quick as he could. Mitchell slipped a finger into my panties and pressed it against the opening of my boipussy. "Mmm, dry as a desert. Too bad I need to keep you nice and clean or I would break you in right now."

Mitchell walked me through a series of back hallways until we reached a broom closet that was in the process of being cleaned out. A guard was standing outside the closet with his thumbs hooked into his utility belt. Even though we were indoors and far from even the smallest window he was wearing a pair of mirrored sunglasses. Clipped to a heavy ring hanging just to the left of his crotch were two chains that lead into the closet. Mitchell and the man shared a nod as we approached.

A moment after we arrived the chains went slack as two inmates exited the. Both men had their prison issue shirts tied around their midriffs and were naked otherwise. The chains went first to their cocks where slide through a loop that appeared to be a piercing and then up to the dog collars around their necks. Both men also had a night stick in their backsides that were being used as a butt plug. The night sticks were the older style with a perpendicular handle a few inches from the base. They were inserted so that it gave the impression that each inmate had a tail sticking in the air.

"'So tell me Rodgers have these two cock whores learned their place yet." Mitchell boomed. Both inmates flinched and almost dropped the boxes they were carrying.

"I think so but I am not sure if another night with the dogs won't make them a little more open and accepting of their place in the food chain." Rodgers said as he took a hold of the chair and shook it like a whip sending a ripple towards the two men's bodies.

"I didn't complain." One of them meekly said.

Mitchell walked up behind the man and took a hold of the night stick pulling up on it firmly. "That you didn't, but your girlfriend here did. And you two are a pair together you keep cell block F from getting out of hand. All you have to do is suck cock. You don't even have to leave your cell. No work duty just keep the boys on your block nice and happy."

Tears began to flow down the man's face. "I want you two to remember that next time you get uppity. I also want you to remember that we have a tape of you getting fucked by that dog and then licking each other's asses clean when it was done. Next time you give me lip you fuck the dog And we send a tape to your wives. I bet they will love that."

Both men started crying now. Mitchell gave each man a hard slap on the ass and sent them back to work. It took them about an hour to clean out the closet and then set up the saw horse. Once they were done I was tied to the apparatus and left in the dark.

I wasn't alone for very long. The door opened and a light was flipped on flooding the room with light. It took almost five minutes once everyone was in the room the door was closed and Mitchell put a hand on my ass and leaned on me. Ok boys, here is the deal we got this little cum slut for four days."

Kenneth piped in then, I hadn't realized he was in the room. I tried not to smile. "You cop friend said we had five days."

Mitchells sighed and continued, "And if that idiot could do math we would but he can't so we get four days. Today he is ours, tomorrow he is the female staffs plaything. Day three is going to be open, last day, well everyone knows how that goes."

The room fell quite as the men all grumbled. Then another voice pipped in a voice I hadn't heard yet, mousey but still full for bravado "All right everyone draw a number and let's start this train."

Numbers were drawn and I spent the rest of the day moaning like a whore as cock after cock masturbated in my boipussy. It didn't take long for the many loads of cum inside my boipussy to start to over flow. Soon my panties, which had been pulled down to my thighs, and my thighs themselves were coated in a layer a thick layer of cum. After lunch the guards stopped cumming in my boipussy and just used it to prime their cocks. Then they came around the other side and shot their load all over my back.

A bowl of food was brought in that had been cut up so it could be eaten without any hands. The bowl was raised to my mouth and I did my best to eat it upside down. After dinner I wasn't used as much and was surprised when the door opened one more time and I felt my hands and feet being released. I looked up and smiled at Kenneth. "Sorry about this. I didn't fuck you today. I mean after this morning."

I smiled and started to close my eyes, but Kenneth gentle shook me awake. "Hey you can go to sleep if you want but Mitchell wants you cleaned up before tomorrow. I can take you into the showers and get you cleaned up if you would like."

"Can we do it in the morning?" Kenneth nodded as I drifted to sleep.

Mitchells voice boomed in the closed closet and woke me up just before a bucket of water was dumped on my head. "Rise and shine fuck toy."