Prison Lesson

Aside from a couple of blowjobs, and some mutual masturbation, I had never had sex with a man before. I was happily married and sexually satisfied for two years. I had never wanted sex with a man before and certainly never thought I would ever have such an experience. Yet, two weeks before my twenty-first birthday I was introduced to gay sex and explained how if it was done right it would eventually save my life. And no matter how ridiculous that sounds it is true and it did save my life.

It all started when I was sentenced to five years at a maximum-security prison. I had been found guilty for doing some creative financial bookkeeping with a bank I worked at. My wife, Phyliss, stood by me at the trial and promised to wait for me. We had to move out of our house during the trial, so we moved into a basement apartment at my Aunt Mae's house. Mae understood what Phyliss was going through because Mae's husband Grant spent eight years in prison when they were first married. Grant was more than an uncle to me, he was like a big brother. He was only nine years older than me and he had been in my life since I was six. Since I didn't have any brothers or sisters and Aunt Mae lived next door she and Grant were like my brother and sister. We knew I would be going to prison, but because I was cooperating with the courts we had to wait for a sentencing date.

About two weeks before the court date, and my last day of freedom, Grant called and asked me to take a shower and come to his apartment. He didn't say why, he just said not to mention it to Phyliss who was going out with Aunt Mae to a baby shower for the evening. When I arrived at the door Grant had a strange look on his face and for the first time in my life I felt weird around him. He invited me in and told me to sit down.

"What I am going to tell you and show you tonight is going to save your life. This is not easy to talk about but I have been in that prison and I promise you it is worse than anything you can imagine." Grant said and then he sat down across from me on the couch.

I am trying to enjoy my last few days Grant! I don't want to think about that yet." I said feeling defensive as if he were just trying to scare me.

"Kid have you thought about what you are going to do for sex while you are in that place?" He asked me. I told him that I made a promise to Phyliss that I would not let anyone touch me and no matter how horny I got I would not touch another person. Grant rolled his eyes and then asked me if I was really that naive. I didn't really understand what he was trying to say, so he just came right out and asked me a question.

"Kid, do you think I had sex while I was in prison?" I said no emphatically because I was sure he didn't and I didn't want him to think that I would think for a minute that he ever did. Grant was a much bigger man than I. He was over six feet and he was always very athletic. Grant would sometimes take his shirt off in the summer time and I would envy his physique, with his hairless torso that was tight and shined in the summer sun. He had huge muscles in both his arms and legs and he was not the kind of man that would be wrestled to the ground easily. I remember when I was a young boy, he and Aunt Mae would take me swimming and he and I would change together in the change room. Grant's penis was huge and it had foreskin, two characteristics that were both unbelievable and foreign to me. I had no idea at that time that I would eventually have a man size dick, even though I am sure today that I am still not as big as he is.

"Well kid I had plenty of sex while I was inside, from the very first night right up until the night I left. And let me tell you, none of it was voluntary!" Grant replied.

"What are you telling me?" I asked not really wanting to know the answer.

"You are going to have sex while you are in there. That is a fact. There is nothing you can do to stop it. However, what you can do is stop the experience from killing you is know how to do it quick and clean". Grant responded.

"You are wrong Grant, I am not going to let anyone touch me!" I explained indignantly as I felt a great need to convince myself now more than ever.

Yes you are. I am sorry to be the bearer of bad news but you are going to have sex and because you are a smaller, prettier guy than me you are probably going to have a lot more than I ever did. That's a fact and you better get real about it quick." Grant said pushing me back into my seat as if to show me I only really had the allusion of control in my life. Grant was also right about my size and features. I was always referred to as a pretty boy, which before that day had been a compliment. I was about five foot ten and weighed about 185 pounds. I was a swimmer most of my life and I was in really good shape but I wasn't terribly strong. I had practically no facial hair or for that matter any hair anywhere on my body so I often looked like a sixteen year old boy rather than a twenty year old man. I was always carded at bars and when my hair was long a couple of years before that time people often though I was a girl.

Grant went on to describe how he was first raped the night he arrived in prison. The guards led him down a long hallway and made him take off all his clothes. They sprayed Grant with some kind of disinfectant after they did a cavity search, which he said was mild violation compared to what was yet to come. Once he was cleaned up they told him to put on just a smock, like the kind you would wear at the doctors office, and then led him into another room where he had to lie on a metal table.

Two guys that looked like prisoners came in, turned out they were prisoners, and strapped Grant's feet into stirrups and his chest down to a table. Grant didn't protest because two guards were standing by and he figured he had to submit. Next the two prisoners spread his arms out and strapped them down as well so that only Grant's head was free. The guards then left the room and one more prisoner came in and closed the door behind him.

The biggest prisoner undid his pants and started to stroke his big penis. He walked over to Grant and told one of the other guys to lower the part of the table where Grant's head was. The table was electric and began to rise at his feet and lower at his head until Grant's head was level to the prisoner's penis. The prisoner told Grant to suck his cock which of course Grant refused to do. The prisoner rubbed the big purple head of his penis across Grant's closed lips, but Grant refused to open them.

Another prisoner pushed the smock up over Grant's stomach exposing his genitals. He pressed a button and all of a sudden the stirrups slowly began to separate until Grant's legs were spread. He was completely vulnerable. His dick and balls were dangling and his ass was wide open. The prisoner with his dick now resting on Grant's closed lips nodded to one of the other prisoners who grabbed one of Grant's balls in his hands. Grant winced as the prisoner informed him that his testicle would be crushed if he didn't open his mouth.