6/7 Prison Sissy Stories – PRISON SISSY CH. 02

Warning: This is a twisted and dark fantasy about a guy who was turned into a sissy in prison. It contains extreme ideals and is generally insensitive. Please do not read if you are easily offended by black cock, black men, or gay sex. I warned you, so don’t waste your time. It is for a particular audience, so again, if that’s not you, no shame in turning back now. If it’s not your thing, well, you can’t say I didn’t warn you.

Sorry in advance for the grammar mistakes. I’m neither native nor the best at writing. Please give me constructive criticism if you have any, and I will learn from you. I’ll edit this story’s mistakes in a later version, so if anyone is interested in helping me, then knock me down. [Check out my profile]

All characters are 18 or older. Now enjoy.

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“I really do like your smell down there. There’s something about your scent that I really love. It’s familiar, it’s pleasant, and it’s enticing,” I replied like a slut with a puppy face. I was always good with my words, and now it worked like an atom bomb.

“Wonderful, someone did their homework very seriously,” he replied with a grin. “Okay, get up. Time to launch. Everybody calls me Shaw. You call me Daddy. Understand?”

“Yes, Daddy.”

Daddy was right, they were looking for food. At the launch, a boy got gang raped while everyone was just enjoying their launch. My lawyer is really a good lawyer. If I tried to save my phat ass, then I saw exactly what could happen to me.

Daddy talked about his little plan of what he’s going to do after his prison time. When he entered the prison, he was sentenced to only 5 years, but he did some bad shit which cost him 7 years. He now has only 2 more years to go.

However, I asked him what he did out of curiosity, but he didn’t like that at all. And then he replied, I sent a boi like you in a comma. I swallowed a big gulp of air, and I zipped my mouth for forever. One thing I forgot to mention is that it doesn’t matter if you’re white, brown, or black, if you’re a wimp like me, then you’re somehow screwed if you don’t play the card right here.

“You’re a smart boi. Did anyone tell you before that?” Daddy gave me a compliment while I was busy giving him some hard massage on his sore muscles after a gym session. Now I know why he sleeps on the top bed. You have to be at least 6’2″ to see what is happening up there.

“I’m in prison for a crime that I didn’t commit.” I replied with a sad face.

“Do you know who did this to you?” Daddy asked in a serious tone.

“I know exactly who did this to me,” I murmured a little loudly.

“My friends can send a Santa to bring him a Christmas present,” he said solemnly.

“Nah, I’m going to kill that shit after I get out.” I said with anger.

“Now you’re talking like a bitch. I liked you the moment I saw you. I’m going to treat you well, just don’t fuck with me,” he replied with a normal tone, like the one you don’t get scared of. “Do you need some professional tips?”

“Hehe!” I giggled. “I don’t want to come here again.”

“I read your profile; you’re 25, but you look more like 16,” Daddy mocked. “So, what do you have in store for the future?”

“Haven’t thought about that yet. Just focusing on how I can survive at least the next three years.” I was enjoying his small talk. The more we talk, the less cock I’ll have.

“I’m definitely calling your lawyer next time,” Daddy joked again. “Don’t worry about that; Daddy will take good care of you. But you need to plan what you’re going to do after prison time.”

“Can I ask something?” I didn’t want to say that, but it’s an old habit.

“Go ahead, I’m enjoying your sweet voice,” Daddy grinned.

“Why do you seem too nice to be true?” I was shaking after saying that.

“Why? Haha. Boi, do you want me to be rough?” Daddy laughed. “You’re so lucky. So you want to suck my cock now, right?”

“Mmmmm, mm aaa. I mean, I thought you were going to use me like a bitch.” I answered nervously.

“I’m going to fuck you like a bitch,” Daddy said. “Now, start stroking my cock and keep talking.”

Daddy’s soft cock was resting on the bed about a foot away from me. I took his cock in my palm, and the feeling was familiar but a lot better. Somehow, I found it enjoyable and relaxing. In my hand, a cock nearly 5 inches soft and thicker than 4 inches; the sensation is indescribable.

“Get naked, because the next time I’ll spank your white ass till the blood starts to flow,” Daddy said with a straight face. “And wait until I tell you to touch yourself.”

“Okay, daddy.” I replied obediently, and then I got stripped naked.

“You want to take a pee or just get a random boner?” Daddy asked sarcastically.

“Amm, aaa,” I didn’t want to lie, so I kissed his cock tip and started stroking him. He was getting hard so quickly.

“Are you sure you are straight?” He mocked me again. “Either way, I’m good. You have money in your account, right?”

Is that what he really wants from me? Now I understand why a man like him would be nice to me.

“Yes, a little.” I was just a cashier.

“I know what you were. The money isn’t for me, bitch. Tomorrow you’ll buy an enema,” Daddy said.

“Do they sell condoms too?” I asked curiously.

“Why? Don’t you like barebacks?” Daddy asked sarcastically.

“Condoms will protect us from…” I got cut out before I finished my sentence.

“Don’t worry, I’m clean. If you’re worried about my size, then you should buy some lube,” Daddy replied.

“Do they sell lube too?” I asked.

“Everything you need. How do you think those drugs came from inside the prison?” Daddy replied. “And don’t forget to buy me a gift.”

“Sure, daddy.” I responded.

“Now show me your homework.” Daddy smirked.

I started giving him the head. His cock was absolutely huge! It was bigger than my forearm and I could barely wrap my hand around it. I started to go to town on his cock like my life depended on it.

Actually, it was. He took me as his bitch, but it doesn’t mean he can’t throw me out now. I couldn’t help but think how small I was compared to him. He must have been at least 12 inches and as big around as a coke can.

“You need a new nickname,” Daddy groaned. “I’ve got some in my mind, just picked one or thought of something smart. Ava, Amber, Emily, Lexi… Barbara…”

Sucking cock wasn’t enough for him. Now he wants to give me a pet name. But sucking his cock was far better than sucking those silicone dildos at home. At least I’m enjoying the taste of it now.

“Aaaaa, Cindy.” I just love this name.

“Sissy Cindy, I like it. You’re doing great. It would look better if you wore lipstick,” Daddy kept moaning and groaning. “Turn around, let me play with your ass. How the fuck do you keep this ass so phat and jiggly, smaaacck?”

After I turned and positioned myself in 69, he cupped my dick and balls, his large hand completely engulfing me and started squeezing me like how you would treat a boobie. He was gentle and his other hand was caressing my ass cheek.

“Your pussy is looking so delicious. From tomorrow, I want it fresh and ready for 24/7,” Daddy said lewdly. “You’re pp throbbing and leaking too much. Are you…”

“I’m close.” He stopped squeezing my pack right after I said that.

“Have you ever tasted your cum before?” Daddy asked.

“A few times. When I get too aroused and don’t get enough satisfaction from orgasm.”

“Self facial?” Daddy asked.

“Yeap,” I replied, while I was busy worshiping his black python.

“My bitches adore swallowing cum, no matter where it comes from,” Daddy explained.

“I’m your bitch, daddy.”

“Good girl,” Daddy groaned while slipping my tongue inside his big slit.

“Hey, Shaw, are you there?” A random inmate called my daddy’s name.

“Not now,” he barked a little.

“You want to taste my Asian bitch? You’ll love her tight holes,” the same random inmate shouted again.

“I’m good with my one,” Daddy replied.

“Must be a special one then. Wanna share for a bit?” That annoying inmate once again.

“Nah,” Daddy replied out of boredom.

“Wow, do you have a princess there? Fuck, look at those bubble phat ass,” the inmate said, referring to my ass.

“Don’t worry, she’ll be yours after I leave this shithole,” Daddy replied. “What do you want?”

“I’m just offering my bitch to my friend… Alright, you’re having fun. I’ll make it small then. I need to borrow some money again,” the inmate said.

“Is it for your bitch?” Daddy asked.

“Yeap, just for a minor surgery,” the inmate replied.

“What’s wrong with her nuts?” Daddy asked.

“I’m making it permanent before she leaves the prison,” the inmate replied.

“Okay, I’ll call my man tomorrow. You’re spending too much money on her,” Daddy said and got back to working on my butts.

“Why is he removing her testicle?” I asked stopped blowing his rock-hard big cock.

Daddy spanked my ass hard. “Keep sucking. None of your business. Take it deeper. How many chicks do you fuck with your big hard manly cock?”

I thought he wouldn’t talk about my small dick. Now he is enjoying humiliating me.

“A few,” I replied.

“A few?” Daddy asked while he squeezed my nuts a little tighter, and that was enough to make me talk.

“Seven including three hookers,” I replied.

“How was the pussy?” Daddy asked.

“Good,” I said slowly.

“I promise, after leaving this prison, you’ll never look at a girl to get laid,” Daddy said with a smirked face. “Tell me your favorite part of my cock, excluding balls.”

“My most favorite part of your cock isn’t the length, size, or pronounced veins running top to bottom of it; it is your cock’s weight. I think it’s heavier than my arm,” I replied, obediently.

“Your lawyer told you to find a friend. I think you finally got one,” Daddy laughed out loud.

“I don’t think I’m in prison with a pal this big and a daddy like yours; I think I’m in heaven,” I exclaimed.

“Haha, you’re special,” Daddy smiled.

Daddy was close. He was throbbing and leaking a lot of precum. I didn’t love my cumies, but his precum was a lot better than what I had tasted before. I started caressing the head in my mouth with my tongue and sometimes making a vacuum while I jacked him off with more enthusiasm.

Suddenly, my monster friend started spurting inside my mouth. I was gulping down semen like a cum-starved whore.

“Mmm, ammmh,” a little moan came out. And then fireworks shot off. I started to spasm on his hand. I felt rope after rope of cum shoot out of my dick into his palm while cupping my whole package tight. I couldn’t help it.

I grinded my hip until my orgasm settled and I regained control of my body. I couldn’t believe I came just to give a man a blowjob. He was playing my dick, afterall. Maybe I was just too horny for him. His manly scent was so intoxicating, especially his cock scent.

“That was awesome,” Daddy exclaimed. “Now clean your mess.”

Then, like a good puppy, I cleaned his hand. I climbed down and washed my mouth and then prepared to get a nice, safe, sound sleep while my daddy looked after my body. I was about to put on my clothes, but Daddy called me up there.

“You’re sleeping with me,” Daddy said.

“Daddy.”

“Ahhhm,” Daddy hummed.

“Why is your bed bigger and higher than others?” I asked like a little girl.

“Haha, my little gurl, if you can feed them enough, they’ll let you live with your wife here,” Daddy gave me a little kiss on my full pouty lips.

“But I don’t have a wife.”

“I like it more, when you play dump,” Daddy responded.

He put his hand under my ear and brought me in for a passionate kiss. When he pulled away, I nibbled at his bottom lip. I opened my mouth to take his tongue. I have made out with girls before, but with Daddy was a whole new territory. I touched his face back, cupped his jawline, and pulled him closer to me to make my actions seem more intimate and heartfelt.

“Mmmmh, uuuuh, mmmh,” I was moaning like a girl.

“Mmmmhhh, you have soft lips. Don’t mind If I eat them like strawberries,” Daddy moaned.

After that, I don’t know when we fell asleep, then we woke up from the bell. I looked at Daddy and he tried to make it a little longer. Then I noticed his morning wood, and I knew what I had to do now.

Before I came here, I was thinking about how I was going to spend the day and how I was going to sleep in this cell after a gang rape. But now look at me. Nobody forced me to do it. Whatever the shit is, I’m loving my prison time, at least for now. I start bobbing on his rigid cock.

“Cindy, are you playing with your friend?” Daddy asked lewdly.

“Amm mmm,” I nodded up and down quickly. A few minutes later, I had my protein shake and then we dressed to have our breakfast. When we finished our breakfast, Daddy told me to start shopping.

“I want to taste your ass before launch,” Daddy whispered in my ear.

“You aren’t coming with me?” I asked and I was scared to go alone.

“Don’t worry, you’re already branded. Even a freak won’t try to touch you,” Daddy replied.

“Do they all know that I belong to you?”

“They know. I used to like tattooing my bitches, but I won’t do such a thing on your nice smooth skin,” Daddy replied, and gave me a long kiss. Then when I turned and was about to go shopping, he smacked my ass hard.

“Uuuh,” I rubbed my ass. It sting a little but somehow I get aroused because of it.

*****

“Give me a big bottle of lube, an enema, and lipstick.” I asked at the counter of the prison shop.

“Tell me your serial number,” the officer asked.

“I read out my serial number from my jumpsuit.” Then he passed my good in the trey. Lube, enema, makeup box.

“Hey, I said lipstick. Why did you give me a hair removal cream and a buttplug?”

“You don’t like eggplug, they’re good for a long time,” the officer replied. “The hair removal cream will take less time than a razor.”

“Alright, I need one more thing.”

Then I left the counter and got back to my cell. Daddy was in the field at that time. So it was the best time for taking poo. I need to get used to this time. I don’t want him to lose interest in me. I cleaned my pussy and used my new buttplug to stretch it a little bit for my huge friend. But taking a shower with all the other inmates was a little difficult.

They were eye-fucking my phat ass. Daddy told me that nobody would touch me, but still I was scared. I finished my shower as soon as I could. I didn’t have any noticeable hair on my legs or arms, but a little fuzz on my pubic area. But I cleaned them all.

I was naked and waiting for Daddy to take my anal virginity. I just spent one day here. Now I’m dripping precum for Daddy’s big, black cock.

“Where is my sweet Cindy?” Daddy called me holding a paper wrapped package.

“Close your eyes, I have a gift for you.” I climbed down. “Now open your eyes.”

“Wow, you look so hot. You brought panties. I like your red lace panties. Show me that ass,” Daddy said. He was already hard in his jumpsuit.

“What is that?” Daddy pointed at my buttplug, then came closer to get a good look. I bend over to give him full access. He didn’t wait to pull that out and buried his face down there. He was eating my ass. Fuck, I never knew that I could feel this good.

“Ahh, mmh,” a soft moan escaped my lips.

“Now, I want to taste those painted red lips of yours,” Daddy said. “You’re looking so stunning.”

He turned toward him, then we started making out again, and we didn’t break our kiss until he carried me up and laid me down on the upper bed.

I was so small compared to his physique. He spread my legs wide open and lay down over me. I wrapped my legs around his waist as he pulled my panties to the side.

“You ready for Daddy’s cock, Cindy?” Daddy asked, staring directly into my eyes. Then he used a lot of lube on his cock and on my ass crack.

“Yes, daddy. Put my friend inside me,” I moaned with delight. He was pushing but slipped twice. I reached down, grabbing his cock with both hands and guiding his big, black cock to put it inside my pussy. I pressed his tip against my pussy and it started to enter me. When I pushed his tip in, my part of guiding him in was over.

“Ahhhh,” my shaked a little the moment his tip got inside me.

“You’re doing good,” he groaned. “Just hold the bed for a minute; the pain will pass away.”

I gripped the steel on both sides of the bed. He began to push in more and more. Daddy’s cock was huge. My breathing became more rapid as my ass swallowed inch after inch. He was roughly a quarter in, but there were three more quarters to go.

He began gently drawing out and then slipping back in. He went through this technique multiple times until I could feel him all the way inside me.

“You practiced at home, didn’t you?” Daddy asked. “Nobody swallowed a big cock like this fast in their ass.”

“Yes, daddy.” I was so stuffed. A foot-long shaft stayed within my little body. I couldn’t believe I was bearing his full big, thick cock inside of me. He paused for a few moments, allowing me to make adjustments to his enormous size before leaning in for a deep, sloppy kiss.

“Is it better than dildo?” Daddy asked.

“Your cock feels amazing, Daddy. That dildo has nothing to compare with your big fat cock. I had no idea what I was missing out on.”

“You want me to show you what else you are missing?” Daddy asked while he was moving his hip in a circle to make my pussy a little more loose.

“Yes daddy. Fuck my pussy.”

He was dicking me slowly and deeply at first, all the way out, then all the way in. He eventually began to accelerate, which felt incredible. When his cock brushed up against my p-spot, it felt wonderful. I read that spots can make me cum hands-free, but I failed every time I tried with my dildos.

“Your clitty dripping like a broken faucet. You want to cum for Daddy?” Daddy sped up a little bit. Every thrust pushed fluid from my prostate and spurted from my erect clitty. Fuck, he gave my dick a name too.

“Huuaamm…it feels sooo good, daddy.”.

I could feel pressure growing inside of me with each stroke. It felt like I was going to explode. Then Daddy rammed into me, and my head felt like it was on fire. When his big black cock pinned me down on the bed, I started shaking uncontrollably. That was the strongest orgasm of my life I ever had. My clitty squirted all over my chest and belly.

“Wow, you made quite a mess there. Now clean it like a good gurl,” Daddy said. “But your job isn’t done until your daddy finishes, princess.”

“Daddy, I just had the most mind-bending, body-bending orgasm of my life. I’ve never had such a sexual thrill before,” I exclaimed. “But why am I still horny? I never imagined I could cum so hard.”

“Because Daddy is fucking all the manhood out of you. Now tell me, do you want more good, hard fucking?” Daddy asked.

“Yes, daddy. I want to cum again.”

“They show me how much you want it?” Daddy said while he pulled out his cock, leaving an empty feeling inside me. Then he lay on his back on the bed. “Hop on me and bounce on my cock.”

I was sitting beside him and looking at his creamed cock standing straight up in front of me. I didn’t know what got inside me, instead of squatting on Daddy’s cock. I shoved it into my mouth. It was right inside my cock, but too late and I was so horny. I just came, but I have never felt this much arousal in my life.

“I was about to say this, but you’re ahead of me,” Daddy smiled. “How’s it taste?”

“I love the taste of my ass on your hot hard cock. Don’t you like your bitches to go a bit dirty?” I asked dramatically.

“You’re not my bitch anymore. I think I have fallen in love with you,” Daddy said. “I’m taking you with me when I go out here.”

“I’ll go wherever you take me, if you promise you’ll always keep me with you.” I put lube on his cock again, then straddled him, grabbing his cock with my right hand to line up with my gaping pussy as I lowered myself onto him until I was fully impaled. I started riding up and down, up and down. This position was amazing; I could control the pace and keep hitting my p-spot. Damn, it felt good. I went even faster, and then faster, until I felt that heavy pressure.

“Ahhh, uug, mmmhh, fuck, mmh.”

I slowed down to take a breath, but Daddy gripped my hips with both of his hands and pushed me down like a hammer. Then he kept stroking his cock with my pussy like a fleshlight. My soft clitty was oozing out seminal fluid everywhere when Daddy was still jerking his cock. I don’t know how long that happened. When I got my sense back, I was still used as a fuck toy.

“What was that?” I asked if I saw a UFO.

“You don’t like it. Look around, you paint all our cell walls,” Daddy said.

“That was absolutely blissful.” I exclaimed.

“I’ll buy a UV light for to show you how much you enjoy my hard fucking,” Daddy said.

“What about yours?” I asked.

“Mine will always go inside your belly or ass,” Daddy replied. “Now, daddy wants to breed you.”

Daddy grabbed me by the hips and flipped me back over onto my back, pinning my knees by my ears. I knew I was flexible, but I didn’t know I was this flexible. He folded me in half like a girl.

“Ever, fucked a girl in this position?” Daddy asked.

“I think I wasn’t strong enough to do that.” I replied.

“Haha, then we’ll say, today is your lucky day,” Daddy said. “Now cum one more time with daddy.”

My pussy was already gapped open. He just filled up the hole with his big fat cock. Then he pistoned his big black cock into me, over and over.

My ass was bouncing up with every thrust. His speed was picking up and his cock was throbbing and getting bigger. That increased the pressure on my p-spot. When he got close, I could feel my orgasm building.

“Ahh, mmh, ahh, emm, mmh,” I was moaning so hard and having a hard time getting hard. I was a little worried about my clitty. After the first orgasm, it still limps like a worm. But my clit didn’t stop for a single moment to leak out my juices.

“Daddy is going to cum,” Daddy groaned and moaned rapidly.

Fuck, I never thought I’d find a man’s moaning so hot and arousing. I heard a loud groan from him and felt his hot sperm fill my pussy. It was too much. I couldn’t take it anymore, as I came for the third time without touching my clitty. My clitty was oozing little strings of cum as he was filling it with his. When he said, “I’ll never try to get laid with girls,” he didn’t lie. When you can get cum like this from a cock, then why are you going to seek some complicated pussy?

“That was amazing, babe,” Daddy said as he gave me a kiss on the lips.

I didn’t expect that kiss on my lips. Then, he pulled out and plugged me in to close my gaping pussy. I shifted left a little to give him space, and he lay next to me. I rolled onto my side, assuming the tiny spoon posture. He turned as well, pressing his crotch against my phat ass.

“Was I good enough?” I asked.

“You already learned what makes a man happy,” Daddy said with a proud face. “You were perfect.”

“What’s in this?” I took that package from under my pillow. “Is it a gift for me?”

“Yes, you gave me a gift, now it’s my turn,” Daddy replied.

“I love gifts. Can I open it?”

“Ofcourse, it’s for you,” Daddy replied.

I opened it just like I used to open my birthday gifts. Today wasn’t my birthday, but it was the day that my life changed for good.

“I brought you short-shorts, wear them with your tank-tops. No more those baggy jumpsuits,” Daddy said.

“Is it made out of a jumpsuit? Where did you find a tailor here?” I asked like a child. “What else do we have here?”

“A parlor,” Daddy replied. “I love that you tried to put on makeup for me, but you need to do it properly. You can learn it there.”

“Let’s take a nap before launch,” Daddy whispered as we both drifted off to sleep. “Sleep tight, my princess.”

To be continued…