Over the years I have done many things I am not proud of. One of those things got my ass in hot water with the law and I was convicted of the crime. Try as I may to flirt with the DA and judge, I still received a 3 year prison sentence. I was sent to a small minimum security prison that looked like it had been built in the 1800s. During proceedings I was stripped and made to bend over, squat and cough to make sure I wasn't hiding anything in my v***** or up my ass. Then I was issued a set a prison clothes and instructed to get dressed. I finally made it to my room which happened to look a lot like a gymnasium with many bunk beds setup for the inmates. I settled in and quickly made a few friends. Eventhough I make bad choices I am still a very nice and trustworthy person. I make friends easily, so it didn't take long before they assigned me as trusty that allowed me to go wherever I wanted within reason. One night I was sitting in my bed when one of the ladies came and told me she had forgotten a teddy bear in the laundry room and feared it would be gone by the time she made it back there the next day. She begged me to go get it because it had belonged to her son. I told her I would go look for it and headed down to the laundry room. As I was down there looking for it one of the male guards came in and wanted to know what I was doing. I told him about the bear but he didn't believe me. He thought I was trying to hide something and ordered me to strip so he could search me. I objected at first, but anyone who has been in prison knows that when a guard tells you to do something, you do it. So I stripped off my clothes standing there in just my bra and panties. He then instructed me to remove them as well. I stood there totally naked as this male guard walked around me eyeing me up and down. Then he asked if I had anything in my v*****. I told him no but once again he didn't believe me. He ordered me to bend over and spread my cheeks with my hands. I did as he ordered and bent over. He walked behind me and rubbed his fingers on my v*****. Then he pushed a few fingers inside me. I wanted to protest but he again told me not to say a word or life would get really miserable for me. I closed my eyes and allowed him to proceed with fingering me. Then I heard the unmistakable sound of his zipper followed by the unmistakable feeling of his c*** rubbing against my v*****. Another few rubbings and he pushed his c*** inside me. He f***** me bent over in the laundry room for several minutes until he finished and pulled out and dropping it on the floor. He then instructed me to put my clothes back on and return to my room. Oddly enough he was decent enough to throw me the bear before I left. I would go on to have s** with this same male guard many times over the next year while I was there. Everytime in the laundry room and everytime later in the evening. He mostly f***** me bent over the table, but we did missionary on the table as well. I also gave him many b******* and swallowed a lot of his c**. At first I hated having s** with him and used to wish he would die, but after time I started to realize I was getting normal s** where most of the ladies resorted to lesbian s**. I actually started looking forward to s** with the guard and even asked him a few times if he wanted to meet for some fun. I ended up riding him several times and had many o****** over the course of a year before they released me.