Inmates Chain Gang
My name is Billy. My last name doesn’t matter. When I was 22 I got pulled over in a stolen Mustang doing about 110 mph. The cops found a couple of joints on me to add to my troubles.
I ended up pleading guilty to the charges and was sent to the county pen for 2 years. I had never been locked up and it’s hard to explain the emotions I felt at that moment, mostly fear and anxiety.
I was showered, given clothes, blankets and one sheet. We were instructed to change the top sheet to the bottom once a week and trade the old bottom sheet for a clean one. One sheet and one towel for the shower, twice a week.
There were 12 of us that came in on the bus. We were put in a segregated block for a week to get used to the routine. It was called ‘orientation’. It was pretty uneventful for the most part. Almost every time we went to the mess hall there was a very large muscular black guy that would wink at me or smile or just look at me weird. Once as he was leaving he grabbed his cock through his pants as if to display it to me. I was glad that the 12 of us were kept from the population for now.
I had heard stories of guys like me getting raped in jail. I am a pretty good looking guy with a smooth body and a ‘baby’ face. I am in pretty good shape but I never work out and I have always been kidded about my ‘girl ass’. One of my friends told me at my going away party that the guys in jail were going to love my sexy feminine body. I was starting to think his joke had a real ring of truth to it and I was more than a little worried by this time.
We were released into the population finally and taken to our new cells. I was assigned to ‘A’ block. I looked around my new cell. It was danker than the one in the reception area where I was being held before. I felt real fear in the pit of my stomach as reality began to set in. I was going to have to find a way to fend for myself in here.
After breakfast we were taken to the deputy warden’s office for job assignments. I also saw my black ‘friend’ again in the mess hall.
"I hear you were a landscaper on the outside Billy," the DW said.
"Yes sir I was," I replied.
"Well son the warden has a need for your services on his property—so I guess today is your lucky day, I’m assigning you to the grounds crew. You get to work outside the walls 5 days a week," he continued. "And let me remind you that if you try to escape you will be given more time and I can guarantee you it won’t be easy time either"
I tried to hide my elation. I didn’t know much about the routine here but I did know that I lucked out on the job assignment. I could see it in the eyes of my fellow inmates and was told so by more than one at dinner in the mess hall later that evening. Even my black suitor looked at me with contempt as he passed by.
There were four of us on the grounds crew. They were all older guys their names were Al, Larry and Tony. Good natured guys it seemed. Not much was said after introductions we just went to work and the head grounds keeper, Tony, told me what needed to be done. I had the rather mundane job of weeding the garden. The Warden’s house was on prison property but was a very luxurious estate. The garden was huge and since he was an organic gardener there were lots of weeds.
Tony was a good looking well built guy with grey black hair and a self assured attitude that I liked right off the bat. He appeared to be a pretty good guy. After I finished the garden I went around to the back of the house to find Tony to see what he wanted me to do next. I was eager to work my ass off to keep this job not only because it was outside and with a seemingly cool group of guys, but it turned out that the grounds crew had their own cell block all to their self. I was later told it was to keep us away from the population so we had less chance of smuggling in ‘contraband’. I was really shocked at the sight that greeted my eyes when I came around the back of the house.
Tony was lying with his eyes closed on a lawn chair by the pool and the other two were in the pool swimming naked.
"Hey Tony, the kid is here looking for you," Al said.
"Hey kid, come on over here," Tony waved.
I was speechless. I guess Tony could tell by the dumbfounded look on my face.
He said, “C’mon kid take off your clothes and take a dip.”
It was hot and I was cooking in the afternoon summer sun but I wasn’t about to jump in the warden’s pool naked. “These guys are nuts,” I thought to myself.
"Are you guys nuts? We can get in real shit for this," I said.
“Okay kid, sit down and let me tell you how this works.”
As I sat in the chair next to his Tony continued, “We can do whatever the fuck we want, the warden is on vacation right now and even when he is here, he is inside the walls in his office until supper time.”
"So there is no one around to say a god dammed thing!" Tony laughed.
Larry and Al getting out of the pool distracted me momentarily. They were both younger than Tony but real good looking guys. Al was tall and lean with longish blonde hair and a full body tan. The water glistened off his body as he walked to his chair to get a towel. As he dried out I glanced at his cock. It was pretty impressive and a little intimidating because I am somewhat below average in that department.
Larry was the strong silent type I gathered at our first meeting. All he said when we shook hands was “Larry”. He was about average height and very muscular. Not bodybuilder type bulky muscular but naturally thick. His hair was a deep black. He turned to face me as he prepared to sit in the chair next to mine. His cock almost touched my face. It was so close I caught a whiff of it. It was short and thick.
"Hey kid," Al said, "Go for a swim man the water’s great!"
"Well I would like to but…"
"But what?" Tony replied.
"I told you there is no one here to do or say anything about it."
"Nobody home but us chickens," Al piped up in a half laughing half singing voice.
Tony laughed and Larry cracked a smile at the joke.
"Okay," I said.
I stood up and took my shirt and pants off. As I lowered my underpants, Tony place his hand on my ass cheek and gently rubbed it as he said, “Wow what an ass!”
"I’m not gay!" I blurted out.
Tony’s hand was still rubbing my ass. I was afraid to move. It suddenly occurred to me that maybe these guys were going to hurt me if I didn’t cooperate and I hadn’t made up my mind yet to resist or not.
"Neither are we," Tony said.
He continued to talk as he rubbed my ass. I could feel his fingers brush the crack. I was getting very nervous and was afraid to talk, so I listened.
"Do you really think you got this job by some stroke of luck?" He continued, "I asked for you, I can get anything I want in this place."
"Huh?" was all I could say.
"An associate of mine that works as a trustee in the reception area described me to you." He moved his fingers deeper into my crack as he squeezed my ass I could feel his finger touch my asshole.
"He described this to me." He squeezed my ass cheek a little harder to emphasize what ‘this’ was. "So here’s the scoop kid," Tony continued, "I don’t know if you’re aware of it but you’re very sexy."
I noticed him stroking his long thick cock now as he spoke. It wasn’t hard yet but it was huge. Al was stroking his semi hard cock too. It was also huge and thick. Larry was behind me and I was almost unaware of his presence.
As Tony spoke again he was trying to wiggle a finger into my asshole. As I tried to turn away he squeezed my ass harder and pulled in such a way as if to suggest it was a “bad idea.”
"We’re not going to make you do anything kid."
I was relieved for a second until he continued, “The truth is kid—with an ass like that, in a joint like this, you’re going to get . It’s not a question of ‘if’ it’s just a question of ‘who’”
He had the tip of his finger almost up to the first knuckle in my asshole. It didn’t feel all that bad.
"That guy that’s been eyeballing you in the mess hall’s name is Isaac," Al said. “He will fuck you and you won’t enjoy it one little bit. He’s a mean bastard!"
Tony added, “We want you to be a part of our group but if you don’t want to, I can get you assigned back inside the walls tomorrow.”
I knew what he was getting a, so when he told me to bend over I reluctantly did so. Tony had worked his finger into my ass a couple of inches by now but it was dry.
"You might as well try to enjoy this kid," Tony said in a gentle voice. He pulled his finger out of my ass and sat up. He pried my ass cheeks apart and began to lick my asshole. I never though of myself as gay. I never really even had any gay fantasies. Now I was bent over with a guy licking my ass—and it didn’t feel too bad. Al stood in front of me with his huge cock in hand, put his hand on the back of my head and pulled down just enough to let me know what he wanted. I had the fear of some mean black guy beating the shit out of me and raping me in my mind as I lowered my head. My lips parted as his big purple knob approached my face. I couldn’t believe I liked the smell and taste of a man’s cock as it entered my mouth. As it hit the back of my throat Al gently rubbed my head as if he was making love to a woman and half whispered, "Just relax your throat and let it in and you won’t gag"
I could feel my own cock react as his long thick cock began it’s descent into my throat and he slowly started to fuck my face. Tony by this time had two fingers in my ass and was pulling and turning as if to loosen me up. He stood behind me and started to rub his mushroom shaped head up and down my crack. Every once in a while he’d stop at my asshole and press a little. I nearly panicked when he stopped the rubbing motion and I could feel the big head pushing to gain entry. Tony rubbed my back gently and spoke softly, “Just relax baby and it won’t hurt much.”
I felt as much like I was being made love to as I was being raped and it helped me to relax. As the head slowly entered my asshole there was some pain but I kept relaxing. Suddenly the head just popped in and it hurt badly. I could feel the thick shaft stretching my asshole to the limit.
Tony was motionless as he spoke again, “Just relax baby.”
He gently rubbed my back once again as I could feel him slowly push the rest of his cock into me. I could feel his prickly pubic hairs tickle my ass cheeks and his cockhead deep in me. He slowly pulled out leaving just the head in. He thrust it in a little faster. I heard myself moan. To my surprise it was a moan of pleasure.
Larry moved into my chair that I was straddled and showed me his cock. It was the biggest and thickest cock I had ever seen.
"Don’t worry I’ll never try to fuck you with this thing he said has he guided my hand to his cock. I couldn’t get my hand around it. I noticed I had a full hardon myself. I began to jerk Larry off while being by Tony from behind and sucking Al’s huge pole. I could feel the hot cum of Tony’s cock pumping deep into my bowels. I could feel the blood rushing in Al’s cock telling me he was going to cum too. As he did the huge cock pumping semen into my throat was so intense I could feel myself cumming all over Larry, who was lying on the chair beneath me.
He laughed and said, “Try some of mine” As he pumped his load up onto my chest. Al pulled his cock from my mouth, Tony pulled his cock from my ass and I dove into the pool.
For the rest of my time in the joint I had it easy. Tony, Al, and Larry never touched each other the whole time I was in prison. I was their woman or slut—or whatever you want to call it—and to be honest, it was some of the best sex I ever had. Even though I am married and living a str8 life now, I still jerk off thinking about my men in jail.