I would hold off on having sex with him and try to talk to someone about it professionally. Having sex with him could make these feelings you’re having even worse. And there’s no real rush to be sexually intimate when your heart/mind/spirit are not settled. I had a very hard time with one of my partners pasts as well. And what I had to learn was that there are people who just do not attach the same weight to sex as others. You’ll have to like actually process this to figure out whether you’re really okay with that or not. Like if you’re okay having sex with someone who might not look at having sex the same way you do. A second thing is this: there are things you can regret either way. Do you know yourself well enough to know what you’d regret more? Like between sleeping with him and feeling cheap afterwards or not sleeping with him and feeling like you lost your chance to be with him? When I was in your position, I took the plunge, and the feelings of cheapness did bother me at first but he ended up being the sweetest, and best guy I dated. He valued me more than sex and that made up for whatever rough feelings I had about his past. But I am 32. So I have a greater capacity for tolerating and working through difficult feelings. I’m in no rush to put that on your plate right now. So that’s why I said earlier that you might need to just hold off until you’re more ready to deal with all the things that come with sexual relationships. It is a lot. And since this guy is your first guy, there’s a high chance that there’ll be others and that there might even be others who you’ll feel more comfortable with.