I've only truly bottomed once for a man, though I've been pegged by a woman many times since.
The only time with a man was weird. I was probably around 20, cruising CL found someone and I was ready. I put a butt plug in so the stretch wouldn't hurt, even tho it still did. But I got there, he was living in an RV on the side of the house...first red flag. He said hi and let me in, and finished his cigarette... Second red flag.
Pretty quick he wanted me, so I started sucking him on the rv bed, before he was even truly hard. I made him put on a condom as I took the plug out my ass. I winced a bit as he entered but once I stretched for him, probably only a 6 inch cock, but nice enough, he started pounding me good.
I loved it, but was afraid to touch my cock and cum early cause I thought I'd ruin it and be grossed out and want to stop.
After about 10 minutes, he pulled out and stood up, picked up a pipe and took a hit...not weed, not cig, he asked me if I wanted I said what is it.. he said M...there's the 3rd red flag... I said no, but the smoke was all around me. I'm no stranger to drgs but i havent done the bad ones you know?
After his hit he put a new condom on and got right back into my ass, thank god. But after a minute or so I felt him pull out and pull the condom off and go back in....final red flag... I asked, did you take it off?? And he said yes, but idk I was so horny or what that I let him keep going, and it did feel better.
Another 10 min, I could hear him getting tired, saying he wanted to smoke more, wanted me to stay the night, so I jacked off before pulled out again and came all over his bed. When he pulled out, and I said I'm ready to leave, picked up my plug off the floor, walked away used. But he didn't cum.
Got back to my car, and took a minute before driving away, letting the usual shame wash over me, I had to pull over and throw up on the side of the road. Showered immediately when I got back.
Never shared that story, "funny" remembering it, as I didn't know I loved being submissive back then. Weird how horny we get sometimes.