First Prison Anal With Kent - Sex Stories

First Prison Anal With Kent

... enjoy the feeling of a mini-cock moving in and out of my ass. I let Kent massage my ass for several minutes and then said “pull it out”!!! As the object exited my rectum. I felt an unusual sensation of pleasure after the repeated mock fucking of my asshole. For the next ten days Kent repeated this exercise with larger and larger dilators. Soon my ass was totally free of pain at the initial insertion and the subsequent false fucking of my asshole loosened me up for what was to come. That Saturday night I was ready to let my lover take my anal virginity. After lights out, I laid naked in bed on my stomach, with my firm ass cheeks facing upward. Kent could not help notice my provocative pose. It was almost pitch dark, looked over and Kent got out of bed and removed his underpants and t-shirt, his cock was fully erect and was certainly hard enough to penetrate me. Kent got into my bed and layed on top of me, his weight pushed me down into the mattress. His head was even with mine and he began kissing my neck, I turned my head sideways and our lips became interlocked in a slow passionate kiss that seem to last forever. I whispered in his ear “go ahead and fuck me, but be careful, take your time with my ass”. With that I felt his rock hard cock pressing between my ass cheeks. It went up and down until it found my rectum. Kent pushed forward and the head of his cock entered my rectum past my sphincter and into my anal canal as it went in, it finally passed all the way past my ...

... sphincter muscle into my anal canal. I was in tremendous pain, my ass was burning as my anal canal expanded to accommodate his phallic shaft. Kent muffled my screams with his hand over my mouth as tears fell down my face. It hurt even more when he slowly inserted the remainder of his cock into my virgin ass. Kent told me to sit still and relax and “get used to it” as he held his cock in place in my rectum. Then to my surprise I began to get used to the feeling of a smooth cock in my ass. The pain of the initial entry had subsided and all I felt was his cock expanding inside me stretching my anal cavity. Then I just stood still until I no longer felt and pain or discomfort. I said to Kent “ fuck me but be gentle and go slow”. Kent slowly began making love to me; he worked his entire cock into me and slowly began moving it in and out of my ass. I moaned softly as it finally went all the way inside me, Kent held it there and then began the slow rhythmic fucking that was his style of making love. My ass now accepted his slow and deep strokes. I was beginning to enjoy being taken by a man. After I relaxed and gave myself to my lover; my hips began to rise to meet his cock as he reentered me time and time again. I was in heaven and began speaking erotically to arouse my lover I said “I know you know I am just starting, but I want you to really enjoy my ass tonight”. Kent whispered back “you are going to get 100 strokes tonight”. It seemed like his lovemaking lasted forever. His hips ...