I'm 28 now but this was back when I was 21.
I'm 6'3", then 285, I don't have a big cock, pretty average, 6" cut. I am a chub even now since I lost weight but I can see my cock and toes just fine without a mirror or bending over.
Anyway, he was 18 and a fem. Wore water balloons in a sports bra, went by a girls name, acted like one, full act. Cutest ass I ever saw so far on a guy.
I was passed out on his couch, our friend asleep in a recliner. I wake up to him watching some guys rimming on his computer. He passes me a note asking if I wanted to fuck, I said yes since I hadn't gotten pussy in a while.
We go into his bedroom where we begin making out, stripping our clothes off and I rim that boi pussy. After a couple minutes, he lubes up his pussy and my cock, puts his legs on my shoulders as I slide full cock into his pussy. We fuck this way while kissing for about 10 minutes before going into doggy.
Once he is on all 4's, I take my time, enjoying seeing my cock sliding in and out that cute little ass. I pull out to prevent from cumming. He then throws me on my back and rides me hard, fast and deep till he cums on me. Right as I'm about to cum, he gets off, gets dressed and leaves. Sadly I didn't get to cum but that was my first time. I fucked him again after that a month later, again, wasn't able to cum. Not because I could but more of a one sided fuck.