My first year in High school my best friend and I tried oral sex on each other for the very first time. We always talked about sex looked at dirty magazines all the time and even jacked off together at times. We had hinted around about trying something together but had never been serious about it until one day the urge got too strong and we agreed to at least try it.
My Parents were both gone to work and it was right after we got out of school. We were back in my room and both took our pants down and tried sucking each other a little. After we went down on each other a couple of times we liked it enough to suck each other longer and longer and right at the last second we stopped and finished each other off with our hand to make each other cum. We were both excited but a little shocked that we actually went thru with this and we were talking about the whole experience and got even more excited.
We had time to try it again so we did and we made each other cum again then pulled up our pants and talked about doing it again as soon as we could. That day started something that lasted for several years and only got better. His dick was much bigger than mine really long and fairly thick and he came a lot too. We sucked each other almost every day for months and eventually we came in each others mouth just to see how it would feel and taste. We both had tasted our own cum many times so we figured what the hell let`s taste each others once. Not long after that we discovered the 69 position and that's when we both actually tried to swallow and it was pretty wild to do that in the 69 position. After that swallowing became part of it and got easier each time.
All thru High School we would sneak around and suck each other off as often as we could and we both swallowed more than our share of each others cum during that time.
Once we got old enough to drive and both had our own pick ups to drive we would ride thru the country on the back roads drinking beer and sucking each others dicks out in the country. On weekends we would be gone all day drinking and just driving around. My Dad had a Deer cabin on some land he had leased and we went there often to drink beer and suck dick. One night we were spending the night there and in the back bedroom naked in bed drunk in a 69 sucking each others dicks and we got each other off and were laying there naked afterwards just talking when he asked if I ever thought about doing other things. When I asked what he told me he wouldn`t mind fucking me. I was caught off guard and a little shocked but wasn`t against trying it but I kept thinking about how big his dick was. We must have talked for over and hour about doing it and the longer we talked the more we thought we might like to try it.
We both knew he would never be able to fuck me without some kind of lube and we looked every where for something to use and all we could come up with was some cooking oil. The whole thing was pretty awkward at first to say the least and we both poured out a little cooking oil and as he rubbed it on his big dick I rubbed some on my asshole and fingered some up inside of me. By then we were both very hard and laughing about it and were talking about how we would do this and what position would be the best for us to try this and finally I just laid on the bed on a towel face down spread my legs and he got on top of me.
After rubbing his big hard dick up and down in the crack of my ass awhile he raised up enough to grab his dick and find my asshole then started to push and it kept slipping off my tight asshole and he would try again until finally I felt my asshole start to expand and he was pushing pretty hard when it went in and I screamed out loud and he took it out really fast. We waited a few minutes and he tried again and after having to pull out three or four times I was able to let him leave it in me but it still hurt and stung quite a bit.
Once I got used to his big dick in m y ass and it didn`t hurt so bad I told him to put it in a little more and as he did I pulled at the sheets and bit the pillow trying to hang on long enough for him to get it in my ass as far as possible. It was pretty painful to say the least but in some strange way it felt pretty damn good too. We never got to see how far it would go up my ass because he got too excited and started to cum before he got it all the way in. I wasn`t expecting him to cum in me but he did and he came a lot and in the heat of the moment he couldn`t control himself and shoved it all the way up my ass and I screamed out loud again as even more cum filled my ass and his dick felt like it was up in my stomach and I started to cum like crazy and never even touched my dick.
He finally stopped shooting his cum up my ass but kept ramming his big hard dick up my ass grunting and groaning and I could feel his huge nuts smashed against mine and we were both breathing very hard as I laid there in a pool of my own cum and my ass full of his cum plus his big dick still balls deep in my ass. He laid on top of me for quite awhile and kept poking his dick up my ass as we talked a little. I had gotten used to the thickness of his dick but the length was still uncomfortable. I could feel his dick getting hard inside of me and we both wanted to do it some more so I told him to go slow. I knew he came a lot but I had no idea it was so much but when he slowly pulled his dick out with just the head still inside of me a huge amount of cum came out of my ass and ran across my nuts then he pushed it all the way back up my ass again then back out several times until it really started to feel good and when I pushed my as up towards him I guess he thought I wanted more then he started to fuck me faster and really started sticking it in me a lot harder and he fucked me for a very long time and cum was still dripping out of my ass when he stuck it in me all the way and came deep in m y asshole a second time.
He laid on top of me awhile then his dick got soft and slipped out of my ass and cum poured out of my asshole and I could tell it was opened up pretty good after having such a big dick in me for so long. He rolled off of me and I just laid there with his cum running out of my ass for awhile then I got up to go shower. He took a shower after I did and we talked awhile before falling asleep. I woke up a few times and cum was still leaking out of my ass.
The next morning I woke up and he was humping my ass and he fucked me again before we even got out of bed. We had all day and night plus the next day before we had to go so we tried it quite a few times in different positions in every room of the cabin and even fucked in front of a mirror a couple of times and I got to watch his big dick go in and out of my asshole and watch his cum run out of me while he fucked me. He fucked me a lot and shot a bunch of cum in me before we had to leave but after that weekend I wanted him to fuck me all the time and I got to where I could take him easily in my ass and he could fuck me as hard as he wanted to for as long as he could and it felt very good and I liked taking his cum up my ass.
We went to the cabin a lot over the years and I was always asking him to fuck me so we fucked a lot plus we still liked to 69 and swallow the cum too. Even after we started dating and getting a little pussy we still snuck around so he could fuck me in the ass and we could sallow a little cum. Later we moved apart to work at our jobs and it has been years since I even heard from him but I will always remember those days and all the good times we had sucking each others dicks and taking him up my ass. I would like to do it again if I ever ran in to him again.