[MM] I (28M) lost my anal virginity tonight

I have been fantasising about this moment for years, using my fingers or whatever I could find around the house (don’t own any toys unfortunately) to try and get an idea of what I was missing out on. I’ve been on several different sites trying to meet someone to make it happen to no avail. On the rare occasion when I found someone, I’d get scared, my anxiety would flare up and I’d back out at the last minute.

Tonight was different. I arranged a meet on grindr and was at his door an hour later. We went straight to his room where he took his pants off immediately. I was on his cock with my mouth immediately. I’d sucked before but I wasn’t into it like I was tonight. The feeling of it growing in my mouth, knowing this time it was going somewhere else, was really getting me going. I was gagging on it a little too much in my eagerness. Eventually we locked eyes and decided it was time.

He made me put his condom on. He said he thought it was hotter when the other guy does it for him. In my eagerness I started putting it on the wrong way and had to correct it. We made while I did that, stroking his length as we did so. I was so fucking ready.

He got me on all fours and started fingering me with lubed up fingers. It felt good. Then he got in close and I felt it pressing against my entrance. He started pushing. I could feel my hole resisting, despite me willing it not to. I wanted this. I needed this. He started playing around, rubbing it around my area, fingering me some more. Then he tried again.

Again my hole was resisting. He said I was too tight. We might not be able to do this. Then something gave. He slid all the way in and holy shit I’ve never felt anything like it. I was in heaven. I could feel his length deep inside me. Then he drew back for the thrust. My god I almost came. I was moaning like a porn star. He pounded my no longer virgin hole for only a few seconds before he slipped out again and my stupid arsehole wouldn’t let him back in. But I don’t care. I say it still counts. We would have tried again but his condom was dried up by this time and he didn’t have another.

I’m now addicted to anal and can’t wait until I have another go.

Source: reddit.com/r/gonewildstories/comments/qxsdj2/mm_i_28m_lost_my_anal_virginity_tonight