I don`t know at what age I started doing this but I was a young boy. Maybe 8 or 9 years old the first time I stuck my finger up my ass in the shower. I liked it so much I fingered myself all the time sand loved playing with my dick. It didn`t take long for me to start experimenting with other things in my ass when ever I had a little privacy and wouldn`t get caught. I knew it wasn`t normal but it just felt good.
My best friend and I had started playing around like most young boys will do and we liked touching each others dicks and rubbing each other all over. Late at night in bed at each others house we would lay side by side with our hands on each others dicks for hours. We both lied doing it so we did it all the time. We even took off our underwear lots of times and rubbed our dicks together and would take turns getting on top of each other to rub our dicks together.
We talked a lot about it so I felt comfortable telling him about how I liked sticking things in my ass and told him how good it felt. He didn`t believe me and said he wanted to see me do it. I thought about it and didn`t see much wrong with it so I turned over face down and it was pretty dark in his room but hre could see well enough that he could watch my finger go in and out of my asshole and he kept touching and rubbing on my ass and even pushed my butt cheeks apart a time or two to get a better look.
He was playing with his dick watching me finger my young tight asshole and we were both enjoying it so I kept doing it until he said he wanted to do it and I let him stick his finger up my ass and he fingered me in the ass for a long time that night. We didn`t sleep much at all that night and he even got on top of me and humped his dick on my ass for a long time.
The next day we took a big risk and went out to their storage shed out back and went inside shut te door and I took my pants down to et him finger me in the ass again as I bent over a few boxes stacked in the corner of their shed. We went there twice that day so he could play with my ass again. He was at my house the next weekend and we were at it again and I showed him my favorite little plastic tube I liked to stick in my ass late at night or when I was in the shower. He wanted to use it on me so I turned over and he pulled my shorts down enough to slowly push it up my ass as I spread my ass cheeks for him. We had to be very quiet of course to not wake my parents but he really liked using it on me so I let him do it for as long as he wanted to and we ended up naked trying it several different ways and playing with each others dicks.
As expected it wasn`t long after that he came up with the idea of sticking his dick in my ass and I thought it was a great idea so that next weekend while I was staying at his house it was during the day on a Saturday we walked down the street to this vacant lot and found a nice private spot hidden back in the bushes and we tried it. We took our pants down enough that he could get on top of me and eventually work his hard young dick in to my tight asshole and right away we both liked it so he laid on top of me on the ground and worked his dick in and out of my asshole for awhile and he stuck his dick in me three different times that morning and each time it felt even better.
We couldn`t stop doing it and the first time he ever shot a little bit of cum was in my ass. Neither of us were expecting it and it wasn`t much at all but I felt it go inside of me and it made my tight ass slick enough that he could stick it in me much easier. Every time we were together it was the first thing either of us thought about doing and we started finding different places to hide so we could do it. Back then our Mom`s always hung the clothes out on the line out in the yard and we even did it in the house while they hung the clothes out to dry.
As we got older we enjoyed it even more and I always liked it when he came in my ass and we learned a lot of different positions and did it all the time. When we got old enough to drive we both had a pick up so we went a lot of places together mostly went fishing on weekends so we liked fucking outdoors a lot and would always end up walking thru the woods to find a nice private spot so he could fuck me in the ass. It was my idea most of the time and I was always asking him to fuck me and he always did. Of course we had a lot of oral sex and both liked to 69 but he never wanted me to fuck him in the ass and I didn`t mind that at all.
When we were 17 our parents let us go to this party that was a few miles away and there was a lot of drinking going on there so we got drunk like every one else did. We made friends with others that were at the party but this one guy hung around us most of the night and it was very late and we were all drunk and ended up at his house still drinking and found out from him he liked having sex with other guys too so we had three way sex for hours and not only did we all suck dick but they both fucked the hell out of me in almost every room of his house. He was 20 years old and very experienced and had a pretty big dick that felt very good in my ass.
More than once that night I had a dick up my ass and one in my mouth and had an ass full of cum the whole time we were at his house. He told me he never saw a guy that liked getting fucked so much and before we left the next day he invited us back and then told me he had a couple of friends that would sure like to meet me. We told him we would come back some time and it was about a month later when we went to his house for a party. Every one started leaving around 2 am but there were two guys that stayed there and between the 5 of us we had a great time. I was the only one there that liked taking it in the ass so I enjoyed all the fucking you could wish for and had four very hard older guys that gave me all I could handle that night.
It was my first ever gang bang and it was great. We went back to his house a few times for the same fun and games and it was good ever time. I guess we all got older and things changed but it was a good time back then and I think about it often.