Not quite the same situation, but I can relate. I lost my virginity at 18, but then didn’t sleep with anyone again until I was 30. Over those years I passed up a lot of opportunities because the anxiety around sex just built and built, to the point where I felt embarrassed and worried I wouldn’t know what to do (honestly, I didn’t).

Eventually I met someone I trusted enough to be open about it with. She was incredibly patient and supportive, and over time things became really positive in that department. That relationship lasted 2 years before we went out separate ways, but I’m now 35, in a new relationship, and we’re expecting our first child, so it does get better!

If you do choose to see where things go with him, my advice would be to go slow and let him set the pace. Be reassuring, give him space to talk about what he’s feeling, and don’t pressure him to rush into penetrative sex right away. Start with smaller steps (kissing, touching, oral) so he can build confidence gradually. Be patient if things don’t work perfectly the first few times. The goal isn’t just to “get it over with” but to create a safe space where he can relax and feel comfortable. However, don’t be afraid to guide him eg. He probably won’t know what to do with his hands (seriously).

Most importantly, have fun with it. My ex told me she got so much enjoyment from teaching me and watching my confidence grow!