Prison Sissy Ch. 03

Warning: This is a twisted and dark fantasy about a guy who 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. You can't say I didn't warn you if it's not your thing.

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. And this story was proofread by two editors. Thank you so much for helping me.

All characters are 18 or older. Now enjoy.

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"Let's take a nap before lunch." Daddy whispered as we drifted off to sleep. "Sleep tight, my princess."

"Holy fuck, how did he take two cocks in one hole?" I was surprised to see a new meat gangbanged by five inmates in the lunch area.

"Cindy, not all new meat is straight." Daddy replied while enjoying his lunch.

"However, those dicks are really massive," I murmured a little loud.

"Big cocks make your mouth watery, don't they?" Daddy made fun of me.

"He's enjoying those big cocks. Fuck, he's squirting now. Now he fainted. He came back. Wow, he's taking cocks like a champ. Two guys are leaving now. Wait, wait, okay, now four new guys joined them. Daddy, he's gonna die." I stood up to see their brutal fuck.

"They're simply dicking him; nothing will happen." Daddy laughed. "Come here."

Daddy took hold of me underneath my arms. He lifted me with seemingly no effort and bent me against the table. I paused a little since I was aware of his next move. It wasn't that they would see me naked. They already watched my live show 20 minutes ago. I was just... I thought Daddy wouldn't share me with others.

"Ass up and moan, sissy. You deserve to be fucked like a whore." Daddy demanded.

"Cock in my ass puts a smile on my sissy face," I murmured. I know men love teasing.

Daddy pulled down my shorts with my ruined panties until they got stuck on my knees. Now he was exposing my ass in the lunch area. The guards had been walking over our heads, while my ass was sticking out and ready to be fucked. I could feel his finger teasing my pussy lips around the buttplug.

"Now, let's see how much you absorbed." Daddy pulled out the buttplug with a "pop" sound. I let out an audible moan. I could feel the creampie dripping from my pussy and hear the drop sound on the floor.

"Looks like we don't need any lube." Daddy said. "Where do you want me to put your buttplug?"

"In my mouth. I don't want it to get dirty."

"Here you go. Ready?" Daddy put it in my mouth.

"Mmmm, mm." I nodded.

My entire body tensed up, and my breathing became ragged when I felt the tip of his cock begin to enter me. Daddy didn't have to wait long to get balls-deep since I was loose and lubed. When he made sure I was ready for some hard fucking, he pulled out his cock and jammed it inside me with one push.

"Uuuhhh, fuck." I moaned.

Daddy began to ram his thick cock deep inside me and fuck my sissy brains out. And he said, "Embrace your inferiority. Take it like a bitch, sissy."

A symphony of girly whines and moans seemed to be forced out of me with each stroke. The sounds erupted from me, I had no control over them. When I looked down, I saw my clitty make a puddle on the lunch table. The real pleasure started when I lost track of how many orgasms I had today. I have never felt this slutty in my life.

"Yes, keep making those sounds. With a girly whimper, Sissy's heterosexuality dies." Daddy groaned.

"Hey, Shaw. Mind if I use the other hole of your new bitch?" A random inmate asked while trying to pull out his cock.

"She'll bite your cock?" Daddy gave him a big smile.

"Man, you could just say no." said the inmate who packed his hard cock inside his pants.

I really thought I was about to get spit-roasted. His cock was almost 10 or 11 inches long and proportionally thick. If he shoved that python inside my throat, there would be at least 22 or 24 inches of cock inside me. Maybe their cocks would collide within my tummy if I were a bit shorter. LoL.

Suddenly, Daddy started fucking me hard. I could feel his cock throbbing. He pushed my head down on the table, and my cheek started caressing the leftover food on the table. The way he was treating me, I wasn't sure I was a man anymore. I was moaning desperately.

"You want more of Daddy's cock, slut?" He groaned.

"Mm, hmmm." I moaned back in a breathy tone. The way he fucked me reminded me of a caption I saw on the internet. It was, "Real men pound the male away, each thrust remaking you into the simpering, whimpering, cock-hungry, cum-thirsty, gangbanging sissy slut that you are." The only thing I hadn't experienced yet was the gangbang.

I was in pure ecstasy while Daddy's thick cock was rimming my asshole. His strong hands were holding me tight like I was his fucktoy. One grabbed my waist and the other my shoulder. My ecstatic squeals didn't stop, nor did his relentless hammering. I stopped counting after the third time I had an orgasm on the table. Honestly, my mind was not in a state to thinking clearly, and I was on the point of passing out. I could never imagine watching a new meat gangbanged and fucked hard in the ass at the same time.

"Do you want me to fill your ass or your mouth?" Daddy asked.

"Yeaa, haammhh, mmm." was all I managed to get out while my mouth was plugged.

"It is ass then," Daddy exclaimed.

He drew me in with his body and kept me tight by grabbing my boobies, hehe. After getting me firmly mashed up against his chest, he took a deep breath and began pounding my sore ass as quickly and vigorously as he could.

"Give me your buttplug." Daddy took it from my mouth. "Damn, you sucked it dry."

"It tastes so good," I mumbled as soon as he took the buttplug.

"Now tell me, are you my bitch?" Daddy asked.

"Yes, Daddy."

"I said, are you my bitch, sissy? Scream it as you mean it!" Daddy demanded.

"Yes, Daddy, I'm your sissy bitch!"

"Daddy, it's hurting a little. You're making a belly bulge on my stomach." I screamed.

"The bulge of a large alpha cock poking out of a beta boi's tummy is one of two bulges they can have." Daddy said.

Suddenly, I shrieked with joy as my eyes dilated. He continued to mount me more aggressively and swiftly. His breath caught with one more thrust, and he let out a groan. His cock blew up and flooded my pussy with hot milk. I could grab his cock head over my tummy.

"Holy fuck, that was awesome." Finally, I could talk properly.

Then Daddy pulled his cock from the pool of cum he left in my ass and, just like the last time, closed my gaping back door with the buttplug. After that, he sat down at the table to catch his breath.

I knelt in front of him and looked up to push his dripping cock to my lips. The moment it slipped inside my mouth, I started to clean it. It has a strong flavor blended with the scent of my pussy and his cock. After fully sucking dry his soft cock, I started licking up everything on his balls, and the flavor and odor were overpowering.

"Yes, babe. That's it. A good sissy keeps her daddy clean." Daddy said. "How was getting fucked in the lunch area?"

"The pleasure of getting fucked in front of people maximized the intense orgasm," I replied.

"That's how that bitch is feeling now." Daddy replied, pointing to the gang-banged bitch.

"Maybe more than me. That boy is taking too much dick." I murmured.

"Haha. And what about getting your brains blown out by experiencing a sissygasm?" Daddy asked.

"Sissygasm?" Is it the orgasm I had with Daddy called? Fuck, I crave it more than fucking a girl's cute puffy pussy. "Does everybody get it, Daddy?"

"The orgasm you're having is called a sissygasm." Daddy replied. "Sissygasm isn't for everyone. Staying limp while getting your boi pussy drilled and slammed shows how useless your clitty has become. Your boipussy is all that matters. Sissygasm is all your body needs."

"So, it's only for me."

"Haha, sissygasms convert curious twink-bois into cock hungry anal princesses." Daddy replied.

"I'm your princess, Daddy," I sat on his lap and hugged him.

"You are, Cindy." Daddy laughed out loud.

******

After lunch, we returned to our cell.

"Daddy!" I called from my lower bed.

"I'm listening." Daddy replied from the upper bunk.

"I saw a few girls were playing... Are they prison hookers?"

"Get over here," he replied. I climbed up. "Did you see if any of them had pussy?"

"Nope!"

"Then they're inmates just like us." Daddy replied, looking at my smooth face. "Do you want to fuck them? Daddy can arrange that."

"Hehe, my balls are still sore, and I can't even clench my dick right now." Daddy touched my lips with his finger to stop me.

"Call it clitty." Daddy replied.

"Okay, my clitty kinda lost all its..."

Daddy stopped me again.

"Do you want to fuck them or not?" Daddy said.

"Aaaa, hmm, I don't know. My mind is still processing all those orgasms I got from your cock." I answered like a confused baby who doesn't know which one is the best ice cream in the store.

"Alright, now tell me about the girls you saw." Daddy said.

"I noticed they have a penis down there. But so small, even smaller than mine. I could barely see it. It was like a girl's clit..." I paused.

"Haha, now you're thinking about yours. Come here, let me cuddle you. Just keep your juicy ass still, or I'll probe it."

I shifted and positioned myself as a small spoon. Daddy laid against me and grabbed my right breast firmly like I was his woman. He started twisting my nipple. I never noticed before how sensitive it was. It was like a mixture of pleasure and pain. Then he again grabbed my breast and squeezed it hard until a groan slipped out of my lips.

"Sorry, honey. Daddy is used to caressing big boobs." Daddy replied with a soft laugh.

"If you keep doing it, then maybe they'll grow," I giggled.

"Haha. The girls you saw all have big boobs, don't they?" Daddy asked.

"Yes, but how did they get them? I didn't notice any implant scars," I asked curiously.

"Nobody will send their bitches away for surgery and start jerking off their cock. But do you like them? Want daddy to help you to grow yours?" Daddy asked while he started eating my right nipple.

"Hormones?"

"Yes. I can arrange that for you." Daddy replied.

"Daddy, do I have a choice?"

"Of course you have. That's why I asked you." Daddy ensured.

"No, daddy. I don't want to. What if I don't like it after prison time?"

"Wow, finally, you have a plan after your prison time. So what is it?" Daddy asked.

"You told me you would take me with you. But your time will end before mine. How do you plan that?"

"Simple, I'll just scare the shit out of your manager. Then he'll take care of the rest of the case. Case dismissed." Daddy replied.

"Can you do that now? I mean..."

"I can, but can you pay me for that?" he asked.

"How much do you want?"

"How much can you give me?" he said.

"I don't have any savings after my lawyer charges. I can take out a loan. Nope, that won't work. And my friends are poor like me, and I lost my inheritance a long time ago. How about I pay you like I'm..."

"But if you go out then, how will you give me that?" he said. "Even if you work 80 hours a week, it'll take years."

"I understand. But surely my debt will be paid if I serve you for the rest of your prison sentence?"

"You're a smart bitch." he said with a grin.

"Hehe, I thought you liked it when I talk smart."

"Enough chit-chat for now. Did you visit the parlor after your lunch?" Daddy asked seriously.

"Sheila showed me some basic things and gave me some of his makeup too."

"Then she wants something from me. You didn't have to pay her, did you?" Daddy asked suspiciously.

"No, I asked her how much it cost. But she said it's a gift from her," I replied in a childlike manner, describing the sweets a stranger gave me.

"I'll talk to her later. Now Daddy wants your slutty cock sucking mouth. Put some makeup on. I want to see your lipstick smudge on my cock." Daddy demanded. "What she did to your eyes is gorgeous."

"What about my bubble butt?" I said, presenting my butt to tease him.

"Don't push it. You won't like it to take my cock in your sore pussy. Now, chop, chop."

Daddy was right. My ass and legs were numb. Sheila gave me some great tips. One of those was that glossy lips are perfect for blowjobs. Putting lipstick on my lips felt different but in a good way. "Shit, I messed it up again." I sighed as I tried to apply a vivid shade of red to my full lips for the third time. Sheila also gave me a manicure and pedicure. I never noticed before my hands and legs were so damn sexy and hot. I have a foot fetish, however, my petite gorgeous smooth feet have never caught my attention sexually. That was a whole new level for me.

"Now you're taking too much time like girls." Daddy complained.

"I think now I'm one of them, and it's what we do." I giggled.

"You know, I'm going to ruin your makeup anyway." Daddy replied.

"Still, it has to be perfect to get ruined. Just wait a minute. I'm almost done with my lips. They'll blow your mind before I drain your balls empty. Now stop talking, and let me finish."

"Ooo, now you're moody like them," Daddy replied with a pretend scared face.

I finished off my cherry red lips with a layer of gloss and took a step back from the steel mirror to see my work. My black, smoky eyes and red lips shined against my milk-white, smooth skin. I was gorgeous and the only two things I was missing were tits and long hair. "How do I look?." I asked, trying to mimic some sexy poses.

"You need to grow your hair long. But still, you're looking perfect." Daddy replied. "Now I want to see those glossy lips on my cock."

"How about you buy me a wig?" I could see his hard cock twitching up from down there.

"Okay, just get one from sheila, I'll pay her later," Daddy replied with a big smile. See that's how you took gifts from men. They stop thinking with their head after their cock gets an erection.

I climbed the ladder, sat between his thighs, and positioned myself to give him a blowjob. As soon as I put my hot, red lips on him, his cock was rock hard and pulsing. I couldn't tell if my lips or his cock were sexier.

"It's time to put my lovely red lips to use. Now enjoy the view, Daddy." I giggled.

I looked at his waiting expression and then wrapped my manicured hot red nail-polished fingers around his thick shaft. I started with slow stroking to extract his precum from the long pipe. The moment I saw my precious pearl come out from the slit, my glossy red lips covered his tip. I gently began to bob my head up and down while suckling on the tip of his cock. The more I was blowing, the more precum I was swallowing. Then, I looked at him to see his burning with pleasure face. Looking at a man's eyes while giving a blowjob works like magic.

"You do enjoy my dick, don't you cock slut?" Daddy smiled. "And your fingers are looking picture-perfect around my cock."

I let my lips slip off his cock head with a satisfying pop sound. "Nope, it's my friend, not just your cock anymore." I giggled.

I got back on his cock and began to gently run my tongue along the underside of his shaft and balls. I love it more when it is messy. Finally, I could feel my dick... sorry my clitty. I could feel it leaking inside my thong. Daddy had already ruined my first panties before lunch.

"I can see your wet spot. Need some squeezing like last time?" Daddy offered me a clitty job.

"I'm good." I replied quickly and kept worshiping my friend. It was intoxicating. Each time his cock thrust into my throat, I could feel more of my precum leaking away. I pushed it a little deeper to test my gag reflex. Then I went a bit deeper until I started gagging on his sloppy cock head.

"We need to work on that more." Daddy smiled.

I was feeling more submissive and girly than I ever imagined I could. I needed more cock down my throat. I kept pushing. I slid my lips deeper and deeper onto his shaft, pressing my throat on his cock head to open. This time, his cock seemed extra big and swollen. Ufff, the moment it got inside, I could feel the stretching of my throat. I increased my pace while its tip went inside my throat. My throat finally accepted this massive intruder.

"Yes, baby, like that.," Daddy growled. "It looks like you fell in love with your best friend."

"My friend is the best. Can't wait to take him deep inside my throat and hold him there until he gives his hot ice cream treat." Naughty talk is another way to make men cum fast.

"Look at you, begging for cum like a bitch in heat. And you absolutely love it, don't you, my sissy cumslut?" Daddy mocked me. "Keep doing that. I'm enjoying your throat bulge."

He firmly grasped my head before pushing me onto his cock and starting to face-fuck me. Daddy was acting like a beast because I teased him excessively. As he repeatedly drilled his firm cock into my throat and let the large bulge form on it. The tears poured down my cheeks. I felt him probe deeper and deeper down until my lips grazed the base of his shaft. I didn't wait for a second to brush my tongue on his balls.

"Take that cock slut." Daddy growled hard, while I was dizzy and about to lose consciousness. My mouth was filled with the flavor of his cock and precum while feeling his big heavenly shafts throb and pulse inside me. I love his cock inside my mouth and throat.

Then Daddy finally pulled his rigid wet sloppy cock from my mouth. I opened my mouth to take the air. My tongue was hanging out and panting to catch my breath just like a bitch in summer. I could feel my face get redder and redder. I was naturally making an ahegao face without even meaning to do it.

I wanted to feel his cum slide down my throat instead of my pussy. My pussy had already been filled with my Daddy's thick, gooey milk, which was still inside me and making squishy noises. I was wondering how much he could cum after two big loads. Even so, his balls suddenly appeared to have enough cum to fill a pool.

"Here is your reward, cock slut. Enjoy real man's cum, sissy. It's the only source of your regular protein." Daddy groaned, spurting his thick creamy goodness onto my cheeks, forehead, chin, mouth, and throat opening. I kept my mouth open wide so that I could store a little more of his delicious cum inside it.

"I told you I'll ruin your makeup." Daddy said.

"That's the reason I did it more enthusiastically," I replied with a happy face from swallowing his cum. I kept eating his cum until my cum coated face was almost dry-cleaned. I looked at his semi-hard cock glistening with my saliva and lips glossing. Then I cleaned his cock as usual.

"Let me clean my hair, Daddy."

"Cindy, Daddy brought some pills for you. Not more than one per day. Tomorrow I'm eating your ass again." Daddy notified me. "Now take some rest. I'll feed your favorite dessert again very soon."

"I'm totally full in both ways."

"They say, you can't feed a sissy too much cum!" Daddy grinned.

"So, you're turning a man into a sissy?"

"Nope, I fuck the boy out and fuck the sissy in." Daddy smiled.

"You want me to be your sissy bitch, Daddy?"

"Yes, sweetie, be a pretty nice bimbo sissy bitch for Daddy." Daddy replied. "Now come here. It's cuddle time."

To be continued...