Should I be honest about being a virgin at 23?

I am 23 years old, and I have not gone all the way. I chose not to, because I have always been afraid of someone claiming ownership over me. I've avoided relationships for a long time, because my previous experiences with boyfriends left me unwilling and feeling pressured to sleep with them because they were more experienced than I was. I have done everything but, but it was always a liberating (?) drunken one night type experience. I have mixed feelings about having done those acts, but now that I have started dating someone who I actually really like and have a lot in common with, I feel somewhat ashamed of these past flings. I really like this guy, but my anxiety about being judged is through the roof at the thought of having to explain these things to him. Now I am wishing that I had just gotten my virginity over with before, because I don't want this to be an uncomfortable experience with someone important to me, and I really don't want to have this discussion with him. But I also want to be brave enough to enter into a relationship with someone that I am actually truly honest with. I want to be braver when it comes to love, but my fear of being stereotyped or made fun is kind of hindering my moving forward. I know I might be an anomaly, but it is not like I have not had the opportunity (which I have, many times) to lose my virginity, So should I be honest with this guy and tell him about it before hand or should I go through with it when it comes time to sleep with him and not mention the fact that I haven't gone all the way and just hope I'm not too awkward?