the virgin thing is interesting, if you know the person well and have built up a good relationship with them then it is the best way, its how i lost mine (16) yet if its someone you are just with just because they are a virgin, then it might just double the erm awkwardness. i dont think the previous person sexual history should matter, cus we all have pasts. she might be a little dissapointed if she doesnt know before hand, but then if she knows then she can help and make sure you are at ease. plus then she gets the added bonus of moulding you into a decent lover. not just a wham bang theres you lot love, kinda kuy.
the only reason you give to being a virgin is your social skills. well thats probably where you want to start. get a hobby, join a club volunteree. meet some new people and improve them. social skills are just that, they take a bit of pratise for some people. but u will get better with time. but just dont feel like you have to get on with everyone or be a door mat if u feel indebted to people.
be yourself and enjoy yourself
the rest will come

peace and progress
snowblind