I was young and dumb and kind of a dick.
I remember like it was yesterday. I was 18 and I fucked this one cute chubbier guy a few times over the course of two days(that’s a story in its self), but I was in a failing relationship. His ass was so amazing when I plowed it using the trojan ecstasy condoms, new on the market. Unfortunately he ruined a good thing, I was going to break up with my boyfriend at the time, but he sure liked telling our friends we fucked before I could do that, mainly because he was happy about taking my huge cock, plus he fell in love with the feeling of ecstasy (me in his tight 16 year old hole). As this was perfectly legal and consensual, we grew apart because of his jealously, however, I always wanted his ass after that because it was truly the first ass I fucked.
One evening I shoot him a message and tell I tell him I’ve been wanting to hang out. This being a year later so I head to his house. We spoon and watch tv and head to bed, but I would pretend to be asleep. He’d try to pull my underwear down, and would suck my cock every time. I’d cum and when I did, I’d “wake up” confused*Wink*. Eventually one night we were in his basement and things got interesting. He sucked me and got my cock wet and rock solid. There was a condom in the reachable distance, but he never grabbed it. Instead he climbed on top on my “sleeping“ naked body and crouched. He played with my cock, teasing his hole and spreading my precum all around it. He then proceeded to grip my cock and made his way onto my shaft. He attempted this multiple times as I would purposefully interrupt by moving my cock so I wouldn’t go in bare. I was nervous, heart pounding and adrenaline pumping. Eventually I caved. The final time his warm hole opened wide and slid down my shaft. I just wanted to feel it for a second but I was trapped with his big body and his perfect bubble ass on me and the feeling of the moment. I felt the inside of his warm hole, bare. It was so amazing and he just road me up and down like a pro. From the top to the balls every time. I was so hard that the feeling was like a consistent orgasm but couldn’t actually cum. This feeling lasted for 2 mins straight but I was too nervous and eventually I pulled my cock out waking up to saying “dude fuck”, started playing with my cock till I came. After he sucked the cum off my throbbing dick, then he rolled over like nothing happened. Pulling my arm over him. I laid with him but I left shortly after since it was about 5 am but that feeling was the best feeling I ever experienced. I never got to fuck his hole bare again, but did meet up a few times as the years passed. Now I’m 28 and he still begs for daddies cock once in a while. I tease him but circumstances keep me from wanting to go back. Unfortunate because I would love to cum in that ass just once and never got the chance.