Straight Male / 35
My Teenager Years With My Bro
When I was in my early to mid teens, me and my younger brother have this thing we would do that was unoriginally called "the thing". You see "the thing" was really just my brother would lay on his stomach on his bed while playing PS2 or Gamecube while I unsuccessfully tried to get my cock into his ass. That is until I leaned about lube and found some KY in our parents bedrooms and that was the missing piece as I mamaged to slide my cock into that tight ass. He didn't cry out beg me to take it out but he did have his head buried. I put all of me in him and that was really it, maybe a few in and out motions but I kind of just kept it in place. I asked a few times if he wanted me to take it out and he said it was okay. I ended up taking it out eventually but my heart was pounding with excitement.
Luckily for me, he still wanted to do "the thing". With lube my cock went on every time and with every new time the easier it got. Eventually I started movements and whenever I asked if it was was okay he would tell me it was. It eventually got his enough where I could pick up just enough speed to make me feel really really good. I had been avoiding cumming in his ass up to this point; not sure why but nerves I guess. But after not jerking off for a few days I didn't care and let loose in his ass as deep as I could.
That's when I realised that he couldn't feel it. He couldn't feel my cum in his ass. From then on whenever we did "the thing" I came in his ass and he had no idea. That is until eventually down the road he learned about that and asked if I did that to when I confessed I had been cumming in his ass. He didnt seem to care which was a good thing for me. He also asked if we were having gay sex and I told him no and that we were just having fun. "The thing" went on for a few more years, usually once or twice a week. He got good at taking it, like towards the end of "the thing" there were times where I was giving it to him with everything I had. I would always ask first, some days he would not be for it, some days he would want it and tell me more while we did it.
Position wise it was always on his stomach or eventually we threw doggy in the mix. If I knew what I knew now, I would of mixed in missionary to get as deep as I could. Anyways I moved away for university so "the thing" stopped. Years later he is not gay engaged to another man: not sure if I jad anything to do with that. I'm married to my wife and have kids. Though I have a thing for anal, its like my kink and the cards were dealt in my favour because my wife only cums from anal. We have actually been only anal for a while now as well she cums from it and we do not want amymore kids so up her ass the cum goes.
Luckily for me, he still wanted to do "the thing". With lube my cock went on every time and with every new time the easier it got. Eventually I started movements and whenever I asked if it was was okay he would tell me it was. It eventually got his enough where I could pick up just enough speed to make me feel really really good. I had been avoiding cumming in his ass up to this point; not sure why but nerves I guess. But after not jerking off for a few days I didn't care and let loose in his ass as deep as I could.
That's when I realised that he couldn't feel it. He couldn't feel my cum in his ass. From then on whenever we did "the thing" I came in his ass and he had no idea. That is until eventually down the road he learned about that and asked if I did that to when I confessed I had been cumming in his ass. He didnt seem to care which was a good thing for me. He also asked if we were having gay sex and I told him no and that we were just having fun. "The thing" went on for a few more years, usually once or twice a week. He got good at taking it, like towards the end of "the thing" there were times where I was giving it to him with everything I had. I would always ask first, some days he would not be for it, some days he would want it and tell me more while we did it.
Position wise it was always on his stomach or eventually we threw doggy in the mix. If I knew what I knew now, I would of mixed in missionary to get as deep as I could. Anyways I moved away for university so "the thing" stopped. Years later he is not gay engaged to another man: not sure if I jad anything to do with that. I'm married to my wife and have kids. Though I have a thing for anal, its like my kink and the cards were dealt in my favour because my wife only cums from anal. We have actually been only anal for a while now as well she cums from it and we do not want amymore kids so up her ass the cum goes.
