First Time Bottoming

This is a confession as well as asking for opinions and advice. I've had plenty of sex with men before, but always topped, which I enjoy very much.

Recently on a work trip, I was having drinks at the hotel bar and got to talking with a very masculine 40 something man who was also staying at the hotel. Small talk turned sex talk as we got more drunk. He was first to bring up MM sex. We were relaxed enough to tell each other a couple of stories. Both of us were 100% tops to that point. Eventually he lamented that it was too bad, because we could have lots of fun. I told him we could have fun in other ways, so we headed up to his room.

It didn't take long for us to be naked on the bed sucking each other's cock. He had a nice 6 incher, same as me. While we were 69ing, he started to grab my ass cheeks and rubbing my hole with his thumb, I didn't object at all and he proceeded to lick my hole. Felt fucking amazing. Eventually I ended up on all fours with my ass spread open and his tongue inside me. Next thing I knew I felt his shaft beginning to push inside me. I just went with it and pushed back. It hurt a bit but felt good. Took a little while to get balls deep. He started to slide it in and out slowly at first and eventually I was getting fucked hard! Anyway, he came in my ass, I came in his mouth. I went back to my room and went to bed.

Next morning, I woke up in pain. My asshole was hurting so bad that I could barely walk. It's been a few days now and I'm still really sore!

So here is where I need to know if this is normal. For those that have bottomed, did it hurt for a few days after? Please comment.

Comments

Anonymous

by Anonymous on Aug 18, 2025 at 8:37 AM

Yes, because it's your first time the more you do it the less sore you become after. like they say practice makes perfect.

(3)  (0)
Anonymous

by Anonymous on Aug 18, 2025 at 9:33 AM

Check out guys first, primarily their dick size.
Bottom for small dick or skinny dick guys.

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Anonymous

by Anonymous on Aug 18, 2025 at 11:05 AM

It hurt the first time and the second time is 50% less. However, it gets more stimulating and after that, it’s a pleasure...

(3)  (0)
Anonymous

by Anonymous on Aug 18, 2025 at 11:37 AM

Always been a bottom, the first few times it hurt a lot. It got easier the more I got it. Now nothing feels better than taking a man - big or small, you learn how to adjust and control your sphincter to better please them and how they like to top you.

(1)  (0)
Anonymous

by Anonymous on Aug 18, 2025 at 3:42 PM

When to Charlotte Pride this past weekend. Got my boy pussy pumped full five times.

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Anonymous

by Anonymous on Aug 19, 2025 at 6:05 AM

Above post: Me and my bestie Peter had been fooling around with each other since middle school. We both were bottom orientated but had zero experience and in no way wanted to be outed by some horny teenager who's gay and bragging about fuckn a cute freshman sissy boy.
We decided to scheme a plan to go to the gay pride parade in a major city over a hundred miles away by saying that we were staying over at each other's house.
It worked, it really worked ! Both of had wonderful sweet surrenders and were hosted by two of the cutest boy's that were brothers, 16 and 17 with parents that actually know that they're gay and supportive.
We've remained boyfriends and all of our parents know and surprisingly they've known all along. We're in our first year of college now and realize how naive we were to take off to the city at 14 with no idea who we'd hookup with. If Jack my now boyfriend and Jorge Peter's boyfriend hadn't met at an ice-cream shop who knows what would of happened to two hick gay boy's from a rural town.

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Anonymous

by Anonymous on Aug 19, 2025 at 8:48 AM

I love bottoming. It’s so hot being fucked as the initial pain turns to pleasure.

(2)  (0)

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