When Chrissy, Chris at the time, was thrown into prison, it was a process of building up trust. He could just rape him if he wanted to, but what was the point of that? He had time to spare, and it wasn't like he was getting out any time soon. Killing a police officer is not something they let you off for, even if he was acting in self defense. The judge didn't want to hear any of that.
He had raped a few new fish, but it just wasn't for him. He wanted somebody who actually wanted to please him, so he changed his approach. Chrissy was his biggest success story. He had lingerie smuggled in for her, makeup and even hormones. Chrisy had a cute pair of breasts and her brown hair grew nice and long.
By the time she got out, she was riding his big black cock like a naughty little slut and begging for more. She actually cried the day she was released She promised to stay in touch, but of course it didn't happen. Tyrone wasn't hurt by that. He knew how it went. The last thing you wanted to do when you got out of here was come back.
He'd had a couple of short term cell mates, but they were gone before he could work his magic on them. Today was the day a new cell mate would be coming. He wondered who it would be this time. "So, what you gonna do, " JD asked? "You've been moping around for too long. The little faggot is gone."
Tyrone turned and gave his friend a threatening look. "Don't be talking about Chrissy like that."
"Alright, alright. I feel you. But you know he ain't coming back to see you, right? What you need to do is find some fresh meat and make him yo bitch." JD grinned and pointed to the short black haired white guy walking along the fence. "Like that one over there."
Tyrone laughed. "You mean the one you fucked?"
"I'm telling you, that one knows how to suck my cock just right, and he's got a nice tight, fuckable ass."
Tyrone shook his head. "JD, I don't want your bitch."
JD grinned. "I'm just saying, gimme that carton of menthols you got coming and he's yours."
"I got my own system, bro. I'm gon get me a new sissy cell mate, you just watch." Tyrone got up and walked over to a couple of black guys who were in a serious discussion. These were two of his associates who helped him get the things he needed.
Back in his cell, Tyrone lay on his bed when the prison guard led a slender, blonde headed guy into the cell. He had no facial hair, blue eyes and his hair was in a pony tail. The guard looked at Tyrone. "Be nice, Tyrone. This kid ain't like you guys. The judge threw the book at him."
Tyrone grinned. "I'm always nice, " he replied as the guard slammed the door shut.
The blonde man sat next to the bars with his arms wrapped around his legs and started crying. Tyrone shook his head as he looked him over He looked to be all of 20 years old. "You got a name?"
"It's Danny, " he sobbed.
Tyrone smiled. "I knew a girl named Dani. Danielle actually. Prettiest thing. You remind me of her. I think it's your eyes. So what did you do to get in here?"
Danny rubbed his eyes. "Pot. I sold pot in my neighborhood. Fucking judge gave me 20 years, and I've never been in trouble before. I just needed the money."
Tyrone looked the small, effeminate man over. "Yeah, don't we all. And don't even get me started about judges. Mother fuckers don't care about justice. You know, if you like to blow smoke, I have some here we could share."
Danny perked up. "Really? I'd like that." He paused "Wait, then I'll owe you."
Tyrone lit a joint. "Girl, relax. I just think you could use this, and I look out for my fiends."
"We don't even know each other, " said the new cell mate.
The muscular black man handed him the joint. "You have an honest face, almost like that girl I used to know. I think we gon be good friends, if you know what I mean."
Danny nervously took a hit off the joint and tried to relax. "So, what are you in here for?"
"Life, " he said with a frown.
Danny handed him back the joint. "Life? For what?"
"I killed a cop, " he replied casually as he took a big hit.
"A cop?"
He blew out a big cloud. "Yeah. Mother fucker tried to set me and a friend up and then threatened us. He shot my friend and I grabbed the gun and killed his ass. Him or me. I chose me."
Danny gasped. "Oh my god, that's terrible. I'm so sorry you had to go through that. " He received the joint and took another hit, feeling a very nice buzz.
The two talked casually and realized they had a few things in common. Both liked to read and enjoyed science fiction. Both enjoyed soul and rap music, even though Danny liked rock & roll too. Both even shared similar political views.
Tyrone surprised his effeminate cell mate. He reached into a box and pulled out a red baby doll nightie and panties. "Do you like this lingerie, Dani?"
Danny blushed. "I've seen the girls on TV wear that. It looks so pretty on them."
He set it on the bed next to him and grabbed some lube. "I bet it would look good on you."
"But I... I'm not gay, Tyrone. Please don't..."
Tyrone laughed. "Relax, babe. I'm not gonna make you do anything you don't want to do, but I'm feeling horny as a mother fucker right now. Pot always does that to me. Do you mind?"
Tyrone pulled down his pants and revealed a thick eight inch cock. He applied lube to it. "I feel like I'm about to burst."
Danny blushed and looked away. Tyrone laughed. "No need to get so nervous. We in here for a long time, baby. We all have urges. Feel free to play with yo little thing too if you want."
Something in the way he said "little thing" made Danny nervous, but he said nothing, He watched as Tyrone came. There seemed to be a lot of it too. "Damn, I needed that. Just a shame I didn't have somebody special to share that with, you know what I mean?"
Danny blushed, and Tyrone noticed. "I got this one," he thought to himself. "Say, Dani, could you hand me that towel by the sink. I made a mess here."
In the shower the next day, Tyrone got a good look at his cellmate's slender and anything but masculine body. He was practically hairless, and had a small cock that couldn't have been bigger than four inches. His own cock started to stir when he noticed one of the black men approach Danny. "Hey bitch. Why don't you get down there and suck my cock."
Tyrone grabbed his arm. "Don't you fuck with Dani over here, understand." He looked around the shower. "That goes for all of you. Hand's off. She's my friend."
Danny felt safe and yet nervous. He loved having protection, but did Tyrone just refer to him as she? The guys laughed. "Uh oh, Tyrone got another girlfriend. She gon be prancing around here shaking her ass in no time, just like sissy Chrissy." They all laughed.
"Stop it guys, you're embarrassing her." He patted his cell mate on the back. "Pay no attention, babe. They just jealous."
The masturbation scene played out in the cell for the next few nights, all the time Danny just watched. Tyrone took it up a notch on the third night as he pulled out some pink lipstick a bra and a pink t-shirt. "I hope you don't mind, but these belonged to somebody I used to know."
Danny watched him stroke his cock again as he talked. "What was her name?"
Tyrone smiled. "Chrissy. She was the cutest little thing, just like you baby. I got her nice things to wear, makeup, even got her hormones."
Danny was confused. "Hormones?"
"Yeah, baby. Female hormones." He felt himself about ready to cum but waited. "See, girls like Chrissy really want to have the body, a pair of tits, a nice ass. I got her hormones. Still have some here too in case I find somebody who needs them."
"So, Chrissy was a guy like me, and he... She... Did she do things with you like..."
Tyrone started cumming. "Suck my dick and swallow my cum? Yeah, she did. That and a few other things. She was real sweet."
Danny was mesmerized by the amount of cum his friend had. He blushed as he thought about swallowing Tyrone's cum. Tyrone grinned. "Relax, babe. I'm not making you do anything you don't want to. But if you ever want to..."
Danny had strange erotic dreams that night. Perhaps it was because he went to bed high, but more likely because of what he had witnessed. In the dream, he was wearing the red panties and nightie and kneeling in front of Tyrone, sucking his cock. He came on Danny's face in a big load. The image in his mind resulted in a very wet dream.
He was almost robotic in the mess hall, just sitting next to Tyrone, listening to the guys talk business. He started to notice there were effeminate men, mostly white, wearing some makeup and clothes in a feminine style. How could those boys let them dress them up like that?
Were they forced too? He knew what went on in prison. Did the bigger black men rape them and make them dress this way? Tyrone seemed to like the idea too, but why didn't he force him to do it for him? He was so nice to him, protected him, shared his pot with him. He seemed to like the idea of having Danny dress in lingerie for him. Would that be so bad, he wondered?
Tyrone had gone out to the weight room to work out when Danny returned to the cell. He went straight to the box and pulled out a red lacy bra. It felt nice to the touch, so he removed his shirt and put the bra on. His cock started getting hard at the sensation as he looked in the mirror over the sink. He put a shirt on over it. He untied his blonde hair and let it flow
He held the satin red panties in his hands. How would they feel over his cock, which was hard as a rock, all four inches of it. He removed his pants and underwear and slipped into the panties. He was on overload as he put the pants back on. What kind of man would do such a thing and get turned on by it? Maybe he wasn't a man at at. What did the black guys here say? Maybe he was a sissy.
Tyrone and JD sat on the bench in the yard, chit chatting about the ball game. "Yeah, but he still should have caught the pass, " said Tyrone. "It was right to him."
JD caught a glimpse of Danny walking into the yard. "Don't look now, but here comes yo bitch. So, you fuck her yet?"
Tyrone noticed that his hair was down and he liked it. He grinned. "These things take time, bro."
JD shook his head. "No, man. You gonna get a bad reputation if you don't tap that sissy's ass. If word gets out that you haven't..."
"Are you gonna say anything?"
"Come on man, you know I'm not. I'm just saying..."
"Don't worry about it. I got this, " he said with a s mile. "By the time I'm through, Dani over there is gonna be riding up and down on my dick and calling me daddy."
As Danny walked towards Tyrone, the panties were showing ever so slightly above his pants. One of the skinheads noticed it and grabbed him. "Hey faggot. I got something you can suck right here."
Danny pulled his arm away. "Leave me alone."
He shoved the sissy to the ground. "Don't you take an attitude with me, bitch."
Tyrone was there in an instant and laid out the man in one punch. "Lay off, she's mine." He reached out and pulled Danny up. "You okay baby?"
Danny felt a tingle. "Yes, thank you. I don't know what I would have done if you hadn't..."
"Don't worry about it. Come sit with my and JD, " he led Danny to the bench. "By the way, I like what you did with your hair."
Danny blushed. and smiled "Thank you."
In the cell, Tyrone pulled out another joint, and they relaxed. He pulled down his pants and reached for the box. Danny stopped him "Tyrone, I have a confession to make."
He pulled down his pants and removed his shirt to reveal the red bra and panties. "I'm sorry. I just couldn't..."
Tyrone stood up and hugged his sissy. "Relax, baby. I wanted you to wear them. Those are your clothes. My girl wears sexy things for me."
He reached into the box and pulled out the satin baby doll nightie. "Would you wear this for me, please?"
Danielle blushed, but did as asked as Tyrone handed her a tube of red lipstick. "And this too, please."
Daniele looked into the mirror and tried to get it just right. Nervously she turned around. "How do I look?"
Tyrone took her into his arms and kissed her. "Does this answer your question, baby?"
She melted into his kiss as she felt his bulge pressed up against her. He sat down and pulled his pants down. "Baby, I've been dying for you to do something for me. Would you?"
"Do we... Do we need a condom for this?"
Tyrone laughed. "Baby, it's just you and me. You ain't sucking any cock behind my back, are you baby?"
She blushed. "Of course not. It's just..."
"Baby, we gon be together a long time. Might as well get used to my cum. I got a lot of it for you. Now, put those pretty red lips on yo daddy's cock."
Danielle knelt between his legs and kissed the tip of his cock. Having never done this before, she could only guess what needed to be done as she licked his hard shaft and then started slowly sucking it. She felt it twitch as she slowly glided her tongue underneath his head. "Yeah, baby, that's perfect."
She gave him a slow and sensual suck as his taste became stronger. She recalled her dream of a couple nights earlier, but she wanted his cum in her month. In moments, she got her wish as he let his manly fluids loose. He smiled as he watched her. "That's it, baby. Swallow daddy's load. It's all for you."
When she was done, they cuddled in the small bottom bed and kissed. "Tyrone. Do you think I should take hormones like your old girlfriend?"
He kissed her. "That's up to you do decide, baby. The hormones will be in the box if you want them. I guarantee you gon be a hot babe if you take them."
They spooned in bed and fell asleep with him holding her in his arms from behind. It was a couple hours later when she got the surprise of her life. Tyrone was hard as a rock and pressing his cock up against her tight sissy hole. She had never been penetrated before. "Tyrone, what are you doing?"
He reached into his box for the lube. "It's time, baby. I need to make you mine."
"But, you're too big, " she protested.
"No babe, you just too tight is all." He spread some lube on her hole and entered it with a finger and then two. "How does that feel?"
"I don't know. It doesn't hurt too bad."
He lay her on her stomach and pressed his cock against her hole. She started to moan. "Bury your face into the pillow, baby. We can't be making too much noise now."
It hurt as the first couple inches of his cock pushed their was past her tight entry way, and she felt a tear in her eye as he kept pushing in. He was determined to get it all inside. He kissed the back of her neck. "You doing fine, baby. Almost in. Just relax. A little more."
Danielle felt like she would be split in half as Tyrone had it all the way in. "There it is baby. How does it feel?"
"Still hurts a little, " she moaned.
"Feels real good to me baby, " he said as he kissed her neck. "Just relax and let daddy take control."
He began to slowly thrust in and out, and the pain was still there as she felt empty and them full with each slow thrust. Was this going to be her life in prison? Was she ready for it? So many thoughts and emotions ran through her mind as he slowly fucked her virgin ass.
Was this so bad? She knew she would probably get raped in prison. Everybody warned her about it. But, Tyrone wasn't bad at all. He was good to her. And, she kind of liked him too. Was it to much to ask to let him have her ass for all the good things he did for her?
"Oh God, I'm gonna love pounding this fine ass baby, " said Tyrone as he continued to thrust inside of his sissy's loosening ass. "How does it feel now, Dani?"
"Kind of nice Tyrone, " she confessed.
He picked up the pace. "It's gonna get even better. Let me know where it feels good and I'll show you. I know how to make girls like you feel good."
She relaxed and started to realize there was a place inside her hat felt really nice when he hit it. She started working on it. "Yeah, right there."
"You like daddy's big cock in yo ass baby?"
"Mmm, yeah, gimme your cock, daddy."
He kept fucking her deep. "I know a few places around here we can fuck. Me and Chrissy used to have a good time. We gon have fun together, Dani. Just you and me."
She was pushing her ass against him as he trust in. "Fuck me anytime. I'm yours. I think I'm gonna cum."
He kissed her neck. "You cum when you feel it. Daddy won't be far behind you."
The pleasure both felt was amazing. Tyrone hadn't had a tight sissy ass in a while. He felt her ass squeeze his cock and knew he as making her cum from the pleasure he gave her. It was a slow and steady cum that felt unlike anything Danielle ever felt before. She could get used to it.
It wasn't long before Tyrone grunted and tensed up. He began filling his sissy's no longer virgin hole. He lay on top of her with his cock still inside her. She felt oddly secure and safe underneath her man. He kissed her on the neck again. "Baby, how long did you say you in for?"
"20 years."
"Well, don't take this the wrong way, but I'm glad."
He pulled off of her and they lay face to face. She felt his warm cum inside her ass, and it felt nice to her. "Why is that, " she asked?
He kissed her deeply. "Because, you and I can have a lot of fun together. The way I see it, as long as we in here together, we're married. You mine, " He kissed her again. "You take care of me, and I'm gon take care of you."
Danielle felt goose bumps, and she smiled. "I think I'm gonna like being your wife."
She melted into his kiss. Prison was not where she wanted to be. But, if she had to be, at least she was in a situation in which she felt safe and secure.
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