A Sissy's New Daddy Ch. 04

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Billie experiences a new dominant.
9.4k words
4.52
75.7k
48

Part 4 of the 9 part series

Updated 06/07/2023
Created 12/19/2011
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sissyneko
sissyneko
463 Followers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dark times been all that has kept me going. A small technical note, I gave this story a good once over, but I have not brought in an outside editor. I did so in past chapters and while it was helpful and appreciated the process simply took longer than I hoped it would. So please enjoy this next chapter and if you are new to the series please go back and read the earlier chapters.

************

The heavy steel door was pushed open with Billie pressed firmly against it. It opened onto the same storage room that the guard, Mitchell always used when he came for Billie. Their meetings had become a regular occurrence at the end of the week. Mitchell watched Billie like a hawk every day. He never stopped any of the inmates from harassing him, but he made sure Billie didn't speak to any of the other guards. Fridays had become a mixed blessing for Billie, the other inmates left him alone when Mitchell was going to use him, but Mitchell himself was temperamental man.

"129873, what is your name?" Mitchell said adjusting his crotch through the heavy guards uniform.

"129873, doesn't have a name." Billie said as he stripped off his orange prison uniform. His yellow silk panties practically glowed against his pale skin. He didn't need to be ordered to strip he knew the routine by now.

"What is your purpose?" Mitchell asked as he leaned against set of empty shelves. His eyes covering every inch of Billie as the young man crawled over to his feet.

"Sir, 129873, lives only to please real men." Billie answered his voice smooth and even. Still acting on routine he reached up and with trembling hands undid Mitchell's belt. Reaching down Mitchell gently caressed Billie's cheek. A smile spread across his lips as his belt came free and Billie unzipped his pants.

"I really want to ask about that tattoo you have, Sissy Bimbo, how fitting. But you see I read the statement you gave to the police again today. That's good stuff, it never fails to get me hard" Mitchell said as he took a firm hold of Billie's chin. "I want you to tell me about the football player."

"The coach?" Billie asked as he slipped his cold fingers into the Mitchell's silk boxers.

"No, we will get to him I want you to start at the beginning. The poker party...

*******

I had just gotten off work at the porn shop and was waiting just outside the entrance for Daddy to pick me up. Randal had been busy that day so we hadn't screwed around, so I was more than a little horny. If one of the half dozen customers that walked past me while I was waiting had even given me a second look I would have dove for their cocks in a heartbeat. Three months of constant sexual debasement had turned me into a pretty wanton slut. While my wardrobe had evolved a bit by that time, I was wearing a boy costume that day.

Daddy didn't bother pulling into the parking lot, he came to a stop at the curb and gave a light honk of the horn. I had already seen him but I think he wanted to make anyone who happened to see us think I was a hooker. Climbing into the passenger seat of his car I wasn't too surprised to find his cock was already out and hard. I leaned across the seat and took him into my mouth, Daddy's cock was warm and already dripping precum. I could feel Daddy's meaty hand fumbling around with the back of my pants; So I reached under me and unbuttoned my jeans. Daddy pushed my jeans up and over my ass before quickly pushing the back of my pink silk thong aside. I felt his finger probing my boipussy and was reminded just how little cock I had gotten that day. When I felt his finger slid in I instantly started to push back and ride his finger. When Daddy stuck a second finger in me I started bucking like crazy, and I felt his cock start to quiver and spasm as he pumped a load of cum into my mouth.

As soon as he came Daddy pulled his fingers out of my boipussy. I swallowed hard sucking the last little bit of cum from Daddy as I carefully slid his quickly softening cock from my mouth. Daddy had mellowed quite a bit since I started being his slut, but his temper would still flair up every now and again. I slipped his cock, back in his pants and zipped him up before I plopped down in my seat.

My pants were still at mid-thigh exposing not only my pink panties but my matching pink garter and stockings. Daddy had expanded my daily sissy wardrobe a while back. He had started making me wear a bra every day, I added the stockings and then the garter belt myself. When I started to pull my pants up Daddy told me not too, which meant he had more plans for me today. I kicked my tennis shoes off and pushed my jeans down into a pile at my feet. I pulled my shirt off and grabbed the whole mess and tossing it in Daddy's backseat.

Daddy waited about fifteen minutes to give me a slip to cover myself. If he was trying to humiliate me he was out of date. A few months ago my heart would have been racing and my boipenis hard. Of course my boipenis was still hard but being naked or close to naked in public wasn't as terrifying as it used to be. When he finally decided to let me cover up, Daddy handed me a deep purple silk nightgown. It came down to my ankles and was slit up both sides to just above my waist.

Once I had the gown settled daddy slipped his hand through the slit in the side and started to massage my boipenis. That told me that Daddy had stopped watching the webcast he made me run every day, I hadn't been able to cum like a boy in weeks. If a cock wasn't pounding my boipussy, I wasn't going to cum. I let Daddy fondle me the rest of the way, moaning occasionally to keep his wrath at bay.

I was completely lost when Daddy pulled off the main road. Who ever lived here, liked being out in the middle of nowhere. There were about a half dozen cars parked along the dirt road leading up to the house. The house was large and well maintained but very old. Two men were standing on the porch beers in hand. I was worried for a half second that Daddy had whored me out to some kind of stag party or another Gangbang. Daddy hadn't organized a group event since that first weekend, but I was still terrified it would happen. Since that first weekend all my slutting around had been one on one or the occasional two on one.

Daddy pulled to a stop in front of the house and hopped out as soon as the engine died. A quick nod meant I was supposed to follow. At my feet were a pair of six inch acrylic heels, I strapped my feet into them and slid out of the car. Smoothing out my nighty I walked around the car my stomach twisting into knots. Both men on the porch looked me over like a piece of prime meat. Three steps led up to the entrance of the house. Daddy waited at the base for me. Taking my hand Daddy made the show of a gentlemen making sure I didn't stumble in my heels. As I reached the top off the stairs the older of the two men, late forties if I had to guess, took a hold of my waist and pulled me too him. His hands were all over me, slipping into my nightgown and past my pink thong.

Slipping a finger into my boipussy the man spun me around pressing me into the porches railing. Once I was pinned against the railing, the man bent me at the waist. Pinned against the railing he pulled his hand from my boipussy and wrapped the back of my nightgown around his hand and pulled. The flimsy silk tore easily with my body weight holding half of it down. With it now in two pieces the man let his half fall to the ground. His voice was calm but dripping with malice "On my property bitches, keep themselves properly displayed. Tell me Frank is this slut going to be better than that last one you trained."

Daddy answered him with a hint of humiliation and anger in his voice, "Yeah George he is a lot better. I tell you I learned a lot from that twat."

The man holding me, George didn't answer he just went back to probing my boipussy with his finger. The other man spoke next, "So how long have you been training this one?"

Daddy liked that question better, and answered quickly "A few months, she broke pretty quick. She knew that she was a slut and has really embraced her place in life."

I tried to look over my shoulder but George smacked me on the back of my head for trying. His voice was quiet and scared the hell out of me. "She... A sissy at its basis is an IT. A really well trained Sissy can be called a girl. Are you a well-trained sissy?"

When I answered quietly, George stuck his thumb in me and using his middle finger he slowly messaged the skin between my boipussy and penis. "What was that now my little cock slut?"

His hand was making it hard for me to concentrate, if he kept this up I would be moaning to loudly to do anything but get fucked. George's motions were so smooth and casual that I didn't feel him gripping my sissy balls until he squeezed them tight. I drilled my eyes closed as I screamed out in pain. All three men laughed at me, as I begged to be released. George just held them tight listening to me begging and pleading. My cock that had been hard all afternoon softened and tears filled my eyes. Just as quick as he started squeezing, George stopped. Even with his iron grip released my sissy balls still throbbed.

I sucked in a huge gulp of air trying desperately not to lose control of myself. My hands were shaking so bad I couldn't do anything with them, George slipped his hand back between my legs and gently cupped my balls. I didn't wait for him to squeeze or even speak, I yelled out as loud as I could. "I am a well-trained sissy slut."

George took his hand away from my balls and unzipped his pants. The pain in my balls had masked that George had pulled his thumb from my boipussy and I didn't realize it until he pressed the head of his cock against me. "You know what to do."

I pressed my hands onto the wooden railing I was bent over and pushed myself back into George's cock. He slipped into me easily as I let out a quite moan. Once I felt Georges body on my backside I stopped and waited for him to fuck me. A small slap on my side told me that George expected me to do all the work. I started moving my hips back and forth in a circular motion, speeding up a little every few minutes when George gave me a light slap to spur me on. No matter how hard I pounded my boipussy against George's cock he seemed completely indifferent as he stood behind me talking. "You know what your problem is Frank?"

George paused waiting for Daddy to answer him. I quickened my pace hoping to distract George and maybe keep Daddy from getting mad. I knew he wasn't going to be able to yell at George so he would have to take that anger out on me. "You think that these toys are people, they aren't people they are sub people at best. It isn't enough that the slave 'embraces' its true self." George let out a laugh as he said that last part and took a firm hold of my hips. "You need to abuse these fuck holes till they live and breathe to please you."

With his hands on my hips George pushed me forward till I was pinned against the railing. Pounding against my back side George felt massive. I was moaning loudly when he finally came pumping the largest load I had ever felt filling my boipussy. Pulling his still hard cock from me, George pumped it a few times send a last few blasts onto my ass. I felt fingers curl into my hair pulling me upright, George turned me to face him and squeezed my nose tight. He looked me in the eye as he spoke, there was a darkness there I had never seen, George I realized was truly evil. "For the rest of the night you will refer to yourself as TWATboi. Go on give it a try."

When I didn't say anything George slipped is hand into the front of my panties, leaning in close to my ears. "Sissy's don't need balls, I know a doctor and it may cost me a bit but I think it might just be worth it."

My words came out in a jumble, "Please don't take Twatboi's balls. Please I will do anything."

George smiled, his lips quivering with excitement as he looked me up and down. With a voice as charming as I have ever heard, George told me how things were going to be. "Nice first step, but you don't own anything, these are your masters balls. Now you owe him an apology for thinking you possessed anything. If you get this right I won't punish you for the mistake you just made"

I looked to Daddy, he didn't look happy, but he wasn't unhappy with me he was made at George. I bowed my head and spoke clearly while keeping my voice low. "I am sorry that I thought that I owned my balls."

Looking back at George I knew I was wrong, he had a shine in his eyes that told me he was happy I had screwed up. I never saw his hand, coming or going, but my cheek burned as if someone had held a bathed it in burning embers. Tears filled my eyes but I knew I couldn't start bawling, if I cried George would own me. "You need to forget the word I there is no I, My, or Me in your life. You are Twatboi and that is how you will refer to yourself. Do you understand."

I started to speak but George smacked me again, this time on the other cheek. George lowered his voice and sounded sweet; if I hadn't seen his dark side I would have been charmed. "Do you understand?"

I nodded my head as George pulled me close kissing me deeply. My boipenis twitched as I closed my eyes. I kept reminding myself that George was evil but his tongue was warm as it slipped into my mouth. I felt his hands move around my waist and cup my buttocks lifting me oh so gently. Dropping me with no warning. George gave me ass hard swat and sent me inside. I spent the next three hours shuttling drinks and empty bottles back around the house. The men used every chance they had to fondle and grope me. I few months back I had hated being groped. It seems it is an acquired taste, because walking around the party that night I felt down right special with all those men paying attention to me.

At the three hour mark is when Daddy started losing. I don't know a lot about poker but watching from outside the game, it looked to me like George and his friends were playing Daddy for a fool. He couldn't see it and I wasn't about to tell him. Of course he ran out of money before he ran out of desire to play. I can't prove it, but I think George was dealing from the bottom of the deck. Once Daddy was out of money he started trading favors, from me. A lap dance here and a blow job there. Within another two hours I had swallowed a load from every man at the table except George that is.

Once he had Daddy where he wanted him, George laid the bet. Most of the nights money was in the pot. "You win and you take the pot home . I win I get the pot and the sissy for the rest of the night."

Daddy couldn't resist, he immediately waved me over. As soon as I was at his side he yanked my panties down and tossed them in to the pot, along with the rest of his chips. I didn't watch George he knew the outcome. I wanted to see Daddy's face. Watching him get taken was amazing. George tossed me my panties and sent me under the table. His cock, was nice, straight and hard as a rock. No matter how much love a gave his cock he wouldn't come.

After a couple of hands I heard the front door open and felt three HARD flicks on the top of my head. I zipped George's pants up and climbed out from under the table just as George started to speak "Mike, it is about time you got home. I got a present for you."

I recognized Mike, he was on the football team. I wish I could see he was a nice guy, like Junior But he wasn't Mike was a cruel douchebag, just like his father. He didn't even say anything to me or his dad, he just licked his lips as he grabbed me by the back of the neck. Mike bent me at the waist and pulled me through the house and down to the basement. I almost fell going down the stairs but thankfully I was able to catch myself on the railing. At the bottom of the stairs Mike swung his door open and shoved me inside.

Standing back up I found Mike going through the top drawer of his dresser. I started to say something but he shot me a look. A small pile had started to form on the top of his dresser. A cheerleader skirt, or at least it was supposed to be I don't think any school would let the girls wear something that short, pompoms, a ball gag, and a couple of cameras. I didn't have a good feeling for the rest of my night.

"Undress me." I walked over to mike and started with his pants. I undid his belt and was about to pop button on his jeans when he stopped me. Taking a hold the belt buckle he pulled it free from his pants. The belt was an Inch and a half side and a quarter inch thick. He rolled it up and tossed it on top of the dresser with the other supplies. Pulling his pants down I wasn't surprised to see that Mike wasn't the undergarment type. I was surprised that he was only a bit over six inches. With his pants piled around his feet I fumbled with Mike's shoes. Once I got them off I stood back up and pulled Mike's shirt over his head. He was fit but lazy, his muscled tone was held together right now by his teenage metabolism.

I took a hold of his cock and he instantly stiffened. I bent my head down and took a nipple into my mouth. It was salty from sweat, and downright delicious. As I rolled his nipple around my tongue I felt him get harder. I moved to his other nipple as he put his hand on the back of my head. With one hand I stroked his cock and with the other I gently massaged his balls. I knew it wouldn't take long. Mike sat himself down and spread his legs wide.

With every breath Mike took his cock would bounce just a little. I locked my eyes on his and knelt down to swallow his cock when Mike shook his head no. I was confused for a second and then Mike motioned for me to step forward. I took a little step and Mike spun me around. His finger felt rough as they slipped into my panties. Two fingers easily slipped into my boipussy as he pulled my panties aside. He pumped his fingers gently into me. It was like priming an engine I was ready to go. The fingers pulled out just before I felt the head of Mike's cock brush against my opening. I lowered myself down savoring every inch of him as filled me.

Once he was buried in me, Mike shoved two fingers into my mouth, they were the same two that had just left me. I tasted George and remembered him fucking me on the patio. My little boipenis strained against the front of my panties. I reached down to pull it free but Mike slapped my hand away. Feeling Mike's hairy thighs against mine I knew I was all the way down. I reached around behind me and squeezed Mike's abs before planting my hands just under my ass. Slowly I started to bring myself back up.

He felt bigger pulling out. Just as his cock was about to pop from me Mike grabbed my waist and slammed me down. A spasm of joy rolled through my whole body as the wind rushed out of my lungs. Mike didn't wait for me to catch my breath, he just started lifting me and dropping me. He was stronger than I thought and felt good to have him pounding into me. My Boipenis hardened instantly and seconds later I shot a load all over the inside of my panties. Mike wasn't done and he kept pounding away. Rubbing against silk panties wet with cum got me hard again, I was just about to cum a second time when Mike jerked me down for a final time. He pressed my backside hard into his lap and grunted as he filled my boipussy with a hot load of cum. I don't know how long it had been since someone serviced Mike but he came and came, filling me to the point of overflow.

Sliding my panties back into place they were quickly soaked with the river of cum pouring from my backside. I turned around expecting to see Mike lulled in bliss, instead he looked angry. "Hey Bitch, this cock ain't gonna clean itself."

sissyneko
sissyneko
463 Followers