Should I be his girlfriend? How do I get over this? Would appreciate advice from people with life experience

Ok, so this may be a little confusing but I'll try my best:

I am trying to decide whether I should be the girlfriend of a guy who I care very much about, and is practically my best friend. We have a really good connection and both feel very strongly towards each other. The problem is, I've never been in a real relationship before. I've never really been in love with anyone before, and although I've made out with people I'm still a sexually inexperienced person at nearly 21 years old.I would like to wait for marriage, but I know that my mind might change eventually. The problem is, ever since I've found out about his past, it's been a really big problem between us. He's been amazingly supportive of me and is trying to help me through it, but I've been emotionally going through a horrible time for the past several months. I feel constant heartache and it makes me cry relatively often. It's not even that bad.he's had sex with several people and the majority were in relationships. He lost his virginity to his high school sweetheart who he was with for a few years, and they were both virgins. This drives me crazy, for reasons I don't even fully understand. I guess I'm just afraid of living in her shadow even though I know that he doesn't care about her anymore. I guess it also bothers me that he lost his virginity to a virgin, but if I end up with him I can't do that. I guess I feel like, since he's already been there and done that, anything between us would never be as special to him as it would be to me. He makes me really happy, but at the same time this tears me up inside. The thought of losing him breaks my heart as well. I'm caught between a rock and a hard place. I've tried so hard to get over this, but so far, it's just not happening. I'm at my wits end.a part of me feels like maybe its just bad timing, like if I could date other people first, then we would be in a better position to be together. However, I don't WANT anyone else. I should also add that I have trust issues because my dad cheated on my mom. Please, I would appreciate advice from anyone, and I would be happy to explain further if you have any questions. Advice from someone older with who has a lot of perspective on life would also be very nice.
Should I be his girlfriend? How do I get over this? Would appreciate advice from people with life experience
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