I had experimented in high school and early college with sticking the head in my ass but not much more. I tried to do a little more bit it hurt too much. In hindsight, it was really because I was too up tight.
Thus happened around 1990. I went to college in Cleveland and one night I met this guy out at the bar one night. I believe it was Keys but it could have been Numbers.. His name was Tom and he worked at Eddie Bauer. He was only slightly older than me.
He asked me to come home with him so I did. He had a couple staying with him from out of town. They had the bed so we had the couch. He sucked me off but I don't remember where I came. He had not cum. I was so exhausted at this point that I told him that I would make it up to him in the AM. I had decided that it was only fair to let him fuck me for giving him blue balls but did not tell him choosing instead to surprise him. That is exactly what happened he fucked me into spoon position. We used hair gel for lube. I made him pull out before coming. I was so proud of myself an I remember telling him that it was worth his wait from the night before. Ha. I was a little full of myself.
I was hooked.
We fooled around a couple of times after that and I was really falling for him. We flipped fucked a couple if times always pulling out but I each time i did let the first shot go in him before pulling oit. He became a jerk and essentially ghosted me or at least he tried to since we would see each other out at the club.
Armed with my new found bottoming skills, I decided that I would let my boyfriend back home fuck me. This is the boyfriend who I was cheating on with Tom. My boyfriend was always the bottom in the relationship and always took it raw from me.
That is exactly what happened. Me and the bf were parked in a parking lot at a playground late at night after clubbing He fucked my bare and missionary in the passenger seat of my Honda Accord with his thick 8 inches. We used suntan oil for lube. I knew that since I had shot my load in him countless times that I could not ask him to pull out so I did not and took my first load. In hindsight, I should not have trusted him but I ended up being fine. We broke up soon after and I never got his cock in my ass again.