A Sissy's New Daddy Ch. 08

I was allowed a quick meal. After being covered in a sheet, while we waited for the twins meal break. The food wasn't as terrible as I expected prison food to be. Before I had finished eating Jennings got a call and hustled me off to a small storage room. The room had been converted to a private breakroom I imagined by the twins. The lock had been switched out so that the key for storage rooms didn't work.

Jennings was starting to panic until she found the correct key. As the lock clicked open I was shoved me to the middle of the room and told to shut up. She set up a couple of small cameras and did her best to hide them. "Keep to the middle of the room, and try not to mumble. These mics suck."

Looking me over one last time, Jennings shook her head. "You're not going to flip out on me are you?"

"This is what I do." I answered as I hopped up on the table and sat down. I spread my legs wide and leaned back on my elbows. Jennings looked nervous but she left shaking her head unsure if I would ruin this for her or pull it off flawlessly. I would do it flawlessly, I knew I would. The door closed and I closed my eyes and took a deep breath. I was in my element, I was dressed as a girl and waiting to seduce two men. I heard the door creak and I opened my eyes, fluttered my eye lids and put a big smile on my face, "Evening boys, you wouldn't happened to have a couple of hard cocks I could fuck do you?"

"You said, Mitchell told you it would be next week till things went private." The one of the right said.

"Do you want to call and argue with him?" the left one said as he reached back and without looking locked the door. Both men dropped their belts and pants in unison, they were wearing jock straps. It took them a moment to struggle out of the pile of shoes, pants and belts at their feet but once they did they decided on me like wolves. The right one grabbed my hair and pulled me down on my back, pulling his jock strap aside I was happy to see he was rather large. I tried to look down at the other, but my head was jerked back and a cock was shoved into my mouth.

The other one rolled my panties down and burred his face been my cheeks. His tongue reached out and tickled my boipussy and then I felt fingers rubbing along my panty covered bopenis. I reached around and grabbed the one in my mouths ass. His hands went to my nipples and tweaked them both. I came instantly. The one licking me moved to my boipenis and started suck it through the wet panties. I moaned loudly letting the vibration tickle the cock until I felt it twitch. His hands flew from my nipples, he grabbed my head and held it in place as he pulled all but the head of his cock from me. I licked the tip and giggled as he pumped a large load into my mouth.

"Don't swallow, you hear my faggot don't you dare swallow." He grunted. I removed my hand from his body and gave him a thumbs up. Carefully he pulled the tip from my mouth. He walked around the other side of the table just as his brother stepped away from my boipussy. HE walked around me and leaned in to kiss me. His tongue pushed my lips apart just as his brother's cock slid inside of me. He held my lips against his until he sucked all of his brothers cum from my mouth.

The one that was kissing me was wearing a pink jock strap. He didn't pull it aside and fuck my mouth, instead he stood up and pushed his ass into my face. He was sweaty and musky but I loved it. I felt my boipenis stiffen and tent out my satin panties. When I pushed my tongue into his hole the man moaned loudly. I pulled it out again and waited for his brother to thrust into me and when he did I pushed my tongue deep into his backside. I continued that until I felt the cock in my boipussy started to twitch. The feeling of his cum pumping into me was amazing and I moaned my lust at into the ass I was sucking on. Carefully he pulled his cock from me and then barked at his brother. The ass was pulled from my mouth and he scurried around to my boipussy. Feeling his lips against my backside. I came again, which after my day was a bit painful. Once all of his brothers cum was sucked from inside me. HE stood up and I felt his cock at the entrance to my body. I smiled but then his brother told him to stop.

"You know the rules." Without speaking the submissive one climbed on the table and laid down on his back. He then pulled me on top of him so I was laying on him. His brother came over and helped him slip his cock into my well used boipussy.

Just as I was about to giggle and moan I felt the other ones cock start to press into me. Before I could scream no, the submissive's hand clamped over my mouth.

"Don't ruin this hole." The big one said as he pushed his cock into me. The pain was intense at first but then the two cocks sliding in and out of me was electrifying. That is the only time I had ever had two men inside of me. They alternated in and out of me and with each thrust I could feel myself coming closer to cumming. With one final thrust both men buried themselves into me and flooded me with their warm seed. As I felt my boipussy filling up I dribbled a load into my panties. I closed my eyes and let sleep wash over me.

Voices woke me up, Jennings, Mitchell and another man. "We had a deal I agreed to let the lezzie bitch take the boy she was supposed to return him unharmed."

I turned my head as much as I could, that was when I felt the metal collar around my neck and when I realized I was naked. Well not completely naked, my boipenis was now locked in a cage. "I am tied of this misogynistic bullshit. Mitch just because you can only get it up for the little girly boys you rent...

"Fuck you." Mitchell yelled his voice trembling with rage. "I have half a mind to run a train on the precious little Janie of yours. Let ever cock in this place fuck all of her holes. Twi...

A booming voice cut Mitchell off stopping him dead in his tracks. "Stop speaking you petulant children."

Jennings tried to speak but immediately stopped. Then Mitchell tried to speak but he stopped as well. "Mitchell your shift has just started so get to work."

"Hold on a minute." Mitchell said the rage kept in check as he spoke to the other man.

"Have you forgotten your place?" The mans voice was low almost low enough that I couldn't hear it. "Do you want me to dress you up in panties and give you a spanking?"

Mitchell didn't respond I could hear people moving around but nothing more. Then Mitchell spoke again, the rage closer to bursting out, "No daddy."

Fleeing the room quickly Mitchell didn't bother to look at me as he left. "He is not ruined."

"He is for my purposes, Mitchell parades a lot of little twinks through this office. But this one looked like he would make a good house boy." The other man said as he walked over to my cage. He squatted down next to it and slipped two fingers through the bars near my mouth. I sucked his fingers into my mouth and treated them like a little cock, licking and sucking with all my might.

"His boicunt will be back to normal later today. They didn't ruin him." Jennings said as she approached him.

"He is ruined for me. I will never stick my cock in a hole defiled by those incestuous gimps." The man pulled his fingers from my mouth with a pop and stood up. "I have been without a house boy for almost a year now and you ruined this one."

"What happened to Trevor." Jennings asked her voice filled with genuine concern.

"Trevor sentence ended and he wanted to go home. As tempting as it was to keep him I don't have time to completely break him. So I released him." The man was sad speaking in a wistful tone. "Ten years he lived with me, he was trained perfect. I hadn't had to spank him in almost 3 years."

That was when I realized that I had lost a chance to escape. I would have been leaving prison today but Jennings ruined it for me. I was angry and I wasn't thinking so I blurted out all that I knew. I told the man of the tape and her control of Jane.

"Do you think I am a fool?" The man said as he walked back over to me. "You think I would let one of my people have a relationship in this place without my knowing about it?"

I didn't say anything I just focused on his feet. The room fell silent both of them waiting for me to speak. "Answer me."

"No sir." I answered my voice only audible because no other sound came from the room. The man unzipped his pants I don't know what I expected him to do but when the stream of warm piss hit my hair I was not prepared and flinched away from him. He had been holding it for a while because it felt like his piss was washing over me forever. When he finally finished up he shook his cock. I looked up at him as he slipped his cock back into his pants.

"Now as for you." The man started walking back towards Jennings. "Tell me what is on this tape."

Jennings started to talk but was cut off with a raised finger, "I think that you would be better at explaining your mistake without your clothes on."

"Please, Sir." Jennings said. But the man raised another finger. Obediently Jennings started to strip off her clothes. Quickly she was dressed in nothing but her bra and panties. She was wearing a matching black satin bikini and full coverage pushup bra. Jennings kept her hands wrapped around her waist holding her stomach tightly.

"The lingerie as well. Has it really been that long?" The man asked as he walked out of my line of sight. Jennings pulled her bra and panties off and tossed them to the side. Her eyes were down cast and she nervously covered her breasts and crotch. "Hands."

Spreading her legs to shoulder width apart Jennings placed her hands on the back of her head. Once she was in the position Jennings sucked in a breath and started whispering under her breath "You can have the tape please not that, I will give you anything that you want."

"Anything." The man said as he moved around and back into my view. He was holding a cattle prod. I had felt a cattle prod and they were vicious. The man clicked the button and snapped an electric arc across the tips of the prob. "What if I asked you to turn that choice little piece of meat you call a girlfriend."

"She is my slave." Jennings said trying desperately to convince the man that Janie meant little to her. But her arms gave it away she tensed when he said Janes name only relaxing when she thought he believed her lie.

"Then you won't mind if I order Mitchell to take her down to a storage closet and let every guard here fuck her." Jennings flinched but it was so small that I wasn't sure if the man caught it. "And then.

Jennings screamed in pain as the cattle prod lit up arcing into her ass. The man laughed as he started talking again. "And then, once she is covered in layers of guard cum, we will take her down to one of the cell blocks and let them have their way with her for a few hours."

The cattle prod snapped again only this time it wasn't against her skin, but Jennings jumped anyways. Jennings held her breath for a long moment waiting for it the electrified spikes to touch her skin. When he didn't she let out the breath. Just as she was about to suck in her breath again the Man touched between her legs and pulled the trigger. Screaming Jennings collapsed to the ground.

Whimpering she spoke, "Please don't give her to him. She will never come back to me. I can't lose her."

The man looked at me and smiled as he tossed the cattle prod onto his desk. Moving back out of my view I listened as Jennings began to cry. Returning the man was caring two very large vibrators dropping the first one in front of her. "Shove that in your cunt."

Jennings grabbed the dildo and pulled it close to her, slipping a hand between her legs Jennings began to rub her clit. Once she was ready she slipped the dildo inside of her pussy. She pumped it in and out a few times until it was buried inside of her. The man dropped the second one in front of her. "Now I want this in your ass."

Jennings looked up and for a moment I could tell that she wanted to protest but instead she pulled the dildo from her pussy and moved it to her backside. She tried to push it in but her body resisted. She pushed again and tried desperately but she couldn't push it in. "I can't."

"I remember the first time I took your ass. Do you?" The man said as he walked over and crouched beside Jennings taking the dildo from her he started to rub it along the soft outer folds of her pussy. "Beg me to fuck your ass again."

"Please." Jennings said as she climbed onto the desk and laid across it. "Please fuck me."

"Say my name, and ask me properly." The man said as he walked over to my cage and let me out. Crawling out I stretched my legs and cringed as I felt the life move back into them. "Get her ready for me, sissy."

I crawled over to Jennings and was about to bury my face into her ass when I realized that the dildo had not been inserted back into her pussy. I held my hand out and the man nodded to me and handed me the dildo. I slipped it back into her. Jennings moaned and then I buried my face between her cheeks. Lapping my tongue against her opening I was pleased to hear Jennings moan each time my tongue brushed against her.

In between moans Jennings found her voice. "Please fuck my ass, Warden Dean. Fill my body with your cock."

The Warden unzipped his pants again and pulled me away from her body. He put his cock at her anus and then he spoke again. "How many men have you let fuck this beautiful ass of yours."

Jennings didn't answer as he began to slowly pump in and out of her. Looking over his shoulder Warden Dean made eye contact with me. Reaching back he pointed to his ass and I knew what he wanted. Burying my face between his cheeks I started to lick while he grabbed my hair and held me in place. He started to pump harder in and out of Jennings grunting in unison with her. "Answer me."

"Just you sir." Jennings said through gritted teeth.

"Good girl." The warden said right before he snapped the cattle prod again. The current rushed from Jennings body to his and on to mine. I would have jerked away but he held my hair tight. He thrust his cock deep into Jennings and shocked us all again. "You're the only whore I fuck like this, I hope you appreciate it."

I stopped listening and just kept licking until the Warden released my hair. I collapsed to the ground and watched catatonic as the Warden pulled out of Jennings and pulled her from the desk. Once she was on the ground before him Warden Dean started to pump his cock until he shot the largest load of cum I have ever seen a man produce on her face. As he shook the last drops onto her face the Warden waved me over and pushed his filthy cock into my mouth. "Now I believe you have some rounds to make this afternoon."

Jennings reached for a box of tissues on the table but the Warden told her no. "If the inmates see me like this..."

"You think they will lose respect for you? Good, now you will know how I felt finding out that you tried to blackmail the twins behind my back." Jennings dropped her head and reached first for her panties. "No those stay and the bra as well."

Without any protest Jennings put on her shirt and then her pants. As she is pulling her pants up over her ass the Warden speaks "Aren't you forgetting something."

Both of them then look to the dildos that are laying on the floor, "Please no."

"Mercy has never been one of my virtues." The warden said as he waited for Jennings to insert both dildos. Once they were inserted Jennings started to pull up her pants and again was stopped by the warden, "Bend over the desk."

Tears spilled from Jennings eyes as she meekly bent across the desk. The warden reached between her legs and that was when I realized that both dildos were actually vibrators. He flipped each of them on and waited a moment before turning them to full power. There was a notable buzzing coming from Jennings pants as he pulled them up.

Standing up Jennings tucked her shirt in. She kept her back to me which gave me a clear view of her ass, the dildo bulged against her uniform obscenely. Being dressed again empowered Jennings and she turned to the Warden, "Please let me clean off my face."

"I have answered that request already." The warden said as he dismissed Jennings with a wave. "I want the tape within the hour."

Jennings stumbled when she reached the door. As an orgasm racked her body. A wet spot began to show-up between her legs. Taking a moment to steady herself Jennings took a few deep breaths and opened the door rushing out.

As the door closed the Warden looked me over. "Are you feeling a little cold. Would you like to put some clothes on?"

He pointed to Jennings discarded bra and panties. I nodded and dressed quickly. The panties felt nice as I slipped them up my legs. Wrapping the bra around my chest made me feel covered and confident for the first time since I had awaken in the cage. I walked over to the Warden and dropped to my knees. "Let me suck your cock. I am a really good cock sucker."

The Warden reached down and took my chin in his hand. "Mitchell, was almost in tears when he found you, your boicunt all stretched out. He was going to make a nice bit of coin with your gang bang today. That combined with the money I was going to pay for you.

The Warden shook his head. "He had a nice little 66 Chevelle picked out."

"I will make a good house boy. I served my last Daddy as a maid and I would cook for him sometimes too." I grabbed his leg pulling it close to me.

"You don't recognize me do you?" The warden said as he kicked me free of his leg. I shook my head and he frowned. "I was there for your very first gang bang. You were a firecracker that night. You fucked my cock better than it had in years. I begged your owner to sell you to me. He refused."

"I was happy to hear you shot him down like a dog." The Warden smiled as he grabbed a hold of my hair. I didn't tell him that I didn't shoot Daddy, I didn't think that it would matter. "Had I known you were Mitchell's newest toy I would have arraigned to take you the moment you were delivered."

Pulling me to my feet the Warden walked me over to a filling cabinet. My hands were cuffed behind my back and shackles were attached to my feet. The metal collar I had been wearing was replaced with a heavier steel collar that kept my face forward and raised slightly. "You know Kenneth actually offered to buy you."

A chain was attached to my collar and run down to the cage on my boipenis, before going through my legs to attach to my hands and then down to my shackles. "He is a good boy, but nieve as sin. I offered to let him have you all he had to do was get gang banged himself. He said no."

Returning to the cabinet the Warden removed a butt plug and a small remote. I was ordered to bend over while the plug was inserted. As I stood back up the Warden held the remote out for me to see. It was small and only had one button on it. The Warden pressed it and the plug inside me came alive, writhing and spinning, my boipenis started to harden and then bulged against the steel cage I was trapped in. the feeling was horrifying at first and then I accepted it. The more I let the mechanical plug over take my body the better it felt. My boipenis started to leak around the steel cage as an orgasm rocked my body and I collapsed to the ground. The plug was immediately turned off.

Standing me back up the Warden examined all the chains making sure they were still attached. The Warden pulled a cape from the filing cabinet and wrapped it around my body and then fitted a spider gag into my mouth.

"So now I will show him what you are really for." The Warden said as he clicked a leash onto the steel collar and led me from his office.

The shower was located in a different part of the prison then where I was cleaned up before. The door was closed as we approached but I could hear a large group on the other side. My steps became halting the closer I came to the door. The Warden yanked the leash drawing me closer to the door. Looking back to me the Warden gave me a wicked grin, "Big smile now, sissy you're going to have a grand time."