When I was younger, I had to do some time in a county jail in Texas. The crime was minor and I was quickly made a trustee. I had the privilege of moving freely about the jail. I would clean and take meals to the guards who were on perimeter posts.

I was not a big guy, and I knew I was kind of bi. I kept it hidden, but with all the testosterone and cock around, it was difficult. I would be hit on by the men, but I played it straight. Once when I was taking a food tray to one of the guards I entered his shack. He stood up and tucked his penis away and buckeled his pants back up. There was a girly mag on the table, and I played it off saying that I hope I didn't interrupt something important. He just grinned and sat back down to eat his food. He made small talk with me and offered me some of his meal. He said to go ahead and deliver the rest of the food and to stop by when I was done so we could talk some more.

When I got back we started the small talk again. He was standing and had me sitting. He was always getting the conversation into a sexual nature. He was showing me the girly mag and asking if I had a girl back home. I could tell he was hitting on me. He told me he was in between girls and was looking for a new one, or a mouth or an ass. He said I had a nice figure, and kind of looked girly from behind. He could tell I was flushed, and asked if I gave it up on the inside. I didn't answer quickly enough because I was looking at his growing bulge.

He came over by my face, unzipped his pants and pulled out his dick. He told me to go ahead and suck it. I was overcome by lust and grabbed his dick and started to swallow it, lick it, and jack it. He said, "Oh yeah that is it". He began to grind in my face and put both hands around my head. He told me how horny he was, and that it wouldn't be long. With a grunt he began squirting down my throat.

He told me where he would be at on his next shift as he zipped up, and told me to meet him there again. I was so horny when I got back to my cell; I jacked and shot in about 60 seconds. I met him again, and he had me on my knees and blowing him immediately. For about 3 days, I blow him several times. Then he was at the post that had to strip search me before entry into the jail. In the strip room, he told me to take off everything and turn around and grab the wall. He was on me in an instant. He was humping on me and stroking my dick with one hand and rubbing my breast with the other. In my ear he was whispering to me, asking me if I wanted his dick up my ass. I let out a small grown and he released his dick from his pants. His penis was a nice dick, about 7 inches, and nicely thick. It felt so hard and hot and large as it pushed between my ass cheeks. He pointed at my ass hole and pushed it steadily into my butt. He was pumping away, stroking my dick rubbing my tit when I blasted on the wall. He came shortly after.

We did all kinds of kinky stuff together. He would hand cuff me, he would cum on his food and make me eat it, and sometimes he would make me wear panties and a bra as he bent me over his desk. One time he told me he had a surprise for me. After the strip search he had me put on a thong and a bra under my clothes. He then took me to segregated part of the jail. At one of the doors we stopped and he opened it. Before he had me go in, he handed me some lipstick, and shut the door. Inside was a very large black man lying on the bed with only a towel on. In a very deep voice he told me to turn around and let him get a look at me. He then told me to strip down to my girlie underwear. He sat up and told me to pretty myself up. I could see my guard was watching the whole thing. I went to the mirror and put on some red lip stick. The big dark black man told me to dance, slowly, show me that ass. It was turning me on so badly. I could see his man hood start to rise pushing up the towel. He told me to bring that sexy mouth over here. He told me to crawl on my hands and knees on the cold concrete floor. I got up between his legs and pulled the towel off. His dick was soft, and large and dark . He had to be all of 9 inches soft. I gently grasped it and it throbbed once, I giggled and he told me to go on and suck it. I placed my mouth over the head and began to lick it. I put it in my mouth and stroked it down to his balls (which were quite large). He smelled so good and put a hand on my head as I sucked on his dick. It oozed precum and every time I moved off it, the strings went from his penis to my mouth. I looked at the door and my guard was photographing it. This really turned me on. As I bobbed on his dick, he reached over to a can of Vaseline and coated his fingers in it. He reached to my ass and began to finger me. One finger, two fingers, then three. He moved me off his cock and told me to get on the bed on my belly. He got on top of me (and he was a big guy). He got on his knees between my legs and lubed up his cock. He told me to "look back here white boy, look what I got for you!" He lay back down on top of me, and told me to say how much I wanted that big black cock. He began to hump on my hole, gradually working the head in. Then with each long stroke he pushed up into my guts. He fucked me and my dick was cumin the whole time. He got on his knees and told me to back my ass up onto his cock. I did everything he told me to. He lay on his back and made me ride him. He had me get on my back, placed my legs over his shoulders and really pumped into me. When he came, he grunted loudly, and I could feel his dick pumping load after load into my ass.

About once a month I was lead into his cell to please him. He always treated me like a good bitch. My guard friend had me move into his apartment when I got out. I stayed with him for about a year before we grew apart. I will never forget how womanly I felt with these two men.