Bottoming for the first time

Advice

I realize this question has probably been asked a lot but for context, I just turned 35 and have literally never topped or bottomed before. I’ve only even done oral with a couple people. I’ve never been in a relationship, and only started using Grindr recently, so I have less experience than most teenagers do.

I always thought that if and when I did have sex with a guy that I would be strictly a top, but I realize that I am going to attract more tops than bottoms simply because I look really young and slender for my age and present basically like a fem twink.

I’ve been talking with a guy who is really cute for quite a while and he’s strictly a top and I agreed bottom for him. I told him it would be my first time and that I was really nervous and he promised he would go slow and be really considerate and I believe that he will be.

However, I am still extremely anxious and wondering whether this is something I want to through with.
I asked Claude, the AI program, how to prepare and I had no idea how elaborate the whole process is. Claude even suggested poppers which I thought was wild that an AI program is suggesting I take drugs, so between that and the instructions for douching and the fact that some friends of mine have talked about how painful it was for them, I am having second thoughts.

But if I never try it, how will I know if I like it or not? I’m just so conflicted and I’m not sure if the risk is higher doing it and regretting it, or not doing it ever and regretting it. So I don’t even know what I’m asking other than for any advice at all… and should I in fact be taking poppers? Is it so painful that drugs and/or lots of alcohol is required to get through it?

Posted May 8, 2026, 3:48 PM UTC

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