First Prison Anal With Kent - Sex Stories

First Prison Anal With Kent

It is a common misconception that prison sex is violent, f***ed and brutal. For me nothing could be further from the truth. My lover Kent and I sexual relationship started during my second month of confinement. One night I decided to suck his cock and I loved it. For the past few weeks I have been serving my new found prison lover every night. I was in heaven when I sucked his organ and in return he gave me the gift of his sperm. I was officially his prison “bitch” and since he was an important gang leader I was protected from the usual prison predators. About three weeks went by and each night I serviced my older prison lover. But I knew this would not be enough and shouldn’t be enough, Kent deserved to have me any way he wanted. I knew anal sex would be the next phase of our relationship together. The problem was I was terrified of the thought of how much pain I would endure, one of my college lovers tried to take me anally once and I almost died from the pain of the initial insertion. One day I asked my doctor who I knew was gay about my inability to have anal sex. He examined me and said “you have an incredibly small sphincter”. He laughed and said, Jake, who have two choices, avoid anal sex altogether, or have sex and endure the initial pain for the first ten sessions or so. In the process you will make some guy a very happy and lucky man. You will be tight your whole life. I was strongly considering having anal sex with Kent but I knew I probably couldn’t. Then one ...

... night he grabbed my ass and kissed me on the neck. It was then that I decided to reveal my fears to my new found lover. About two weeks went by and nothing was said further, although on occasion he would squeeze my ass as I got ready to suck his cock. Then one day I returned to my cell and there was a package. Kent said “I told you there was a solution for everything, go look in that box? I looked in the box and there was a set of “anal dilators” which were rubber phallic like medical objects of five different sizes. They looked like a set of different size dildo’s each one was bigger and longer than the next, except they were totally smooth. Kent said “tonight we start your lessons” and I said “fine “. That night after my usual blow job, Kent said “lay on your back” I complied and soon some KY jelly was applied to my ass. Kent said “look at this” as he held up the smallest and narrowest dilator in the set. The next thing I felt was the tip of the dilator pressing against my sphincter as he slowly pushed it inside me. Kent was very gentle and I was surprised when the pain of the insertion was less than I expected as the phallic object slowly entered my rectum. Kent got it all the way in and said “just relax and get used to it”, I squirmed around the object as Kent began slowly moving it in and out of my rectum. Kent then said “let me know when it doesn’t hurt anymore and you are used to it then I will move it in and out”. Well strangely enough after a few minutes I started to ...