Update: Hot guy but he has a VERY small dick
For those who provided advice, thank you.
For some of you, your brains are broken.
Anyway, I did talk to him about sex. He understood that I didn’t want to be a perpetual bottom. He admitted he was really inexperienced with bottoming.
He had only bottomed twice, which was a surprise to be honest. I didn’t think it was that few. The first time he said he didn’t enjoy it that much. The second time he said the guy fucked him really hard and it was really painful. His ass was extremely sore for a week. Pulling on that thread, they didn’t really do any prep to open him up. They went right to fucking and the guy just slammed it in effectively. There’s the problem.
I asked him if he willing to try with me - someone who would be willing to work with him and take it slow - and he said he would be willing to try.
We talked about some prep from a dietary standpoint and I sent him some good videos to help too.
We met up to fuck. Through a combination of toys and other foreplay, he was relaxed and when I started to fuck him, he was ok. And as we got into it, he really started to enjoy it. He came very easily while I fucked him.
After we got cleaned up, I asked him what he thought. He said he really enjoyed the experience mostly because he came super hard.
I think we might be able to make this work! I won’t be providing more updates but thanks everyone for the advice.
Update: I appreciate the interest in further updates but I’ll be silent moving forward. Key takeaway is just talk to the other person but it doesn’t hurt to ask others for help in framing the conversation correctly.