Ultimately it's up to you. A sexual past is either a deal-breaker or a relationship strengthener. There really is no middle ground here. Everyone has a past in one way or another, but some past decisions do leave lasting baggage that not only hurts the person who is reaping the consequences of their behavior, but people who grow close to them as well. I wasn't a virgin when I met my husband and neither was he. In fact, both of us had previously been married and had children from our previous marriages. I couldn't, realistically, expect to marry a virgin. There is nothing wrong, however, if you want that.
If it's about the issue of you striving to be a virgin until your wedding night and his past lack of wanting the same thing is what's bothering you then that is something you may be able to work through. If you're constantly mentally filling in the blanks and trying to picture what it was like and were they pretty, etc. then it will destroy the relationship because it will destroy your inner peace first.
I'll let you in on a secret, though, and it deals with this statement:
and the thought of it no longer being a special thing for him.
Some people may disagree with me, but you don't have to be a virgin on your wedding night for sex to be special. By no means am I saying go ahead and just do it with this young man because it will still be special. What I'm saying is if the two of you were to be married some day then being intimate with you will be the most special thing he's ever experienced.
I had been sexually assaulted as well as highly sexually promiscuous prior to meeting my husband. I also divorced a cheating, abusive husband at the age of nineteen and had a child. I assumed no man would want a serious relationship with me, so I fooled around a lot. I'm not proud of it. Anyone who tells you sleeping around is empowering is lying to you and themselves. It's a form of physical, spiritual and emotional bondage. Despite the both of us having previous partners, sex with my husband is not only very special, it's sacred. It's special because we're in love and we're soul mates and we have a mutual care and respect for one another. It is absolutely nothing like casual dating sex or one-night-stand sex.
In the long-run it will be up to you to decide if his past is going to effect your future.
ETA: I also agree with the opinion that knowing every sordid detail about a person's past relationships (including sexual encounters) is not beneficial to a relationship. It just adds confusion and feelings of insecurity. To me it's almost borderline perverse to want to know how good a previous partner was in bed, what they did together, how frequently they had relations, what their name was, what was their body like, etc. There is something to be said for tact and discretion, even in a serious relationship. I'm not condoning outright lying, but no one gains anything but heartache and jealousy from demanding the "dirt" on previous partners.
