It could be that the social environments that you've been in have been quite hostile and unforgiving. When I see the level of shallowness and insensitivity among a lot of modern young Americans I'm positively disgusted. I say that on the assumption that your peers have been less-than-friendly and sensitive toward you. It's hardly surprising that rates of social anxiety among young people are going through the roof, when you see what a lot of young people are like today.
Don't worry too much about your virginity, as has already been said, you don't want to lose it to some hoe. You have to remember that sex and relationships have been cheapened to a harmful degree and those girls that judge guys by their sexual experience do not value it, or in some cases don't see other people as people, but sources of short-term pleasure. If someone was to reject you because of that, because of anticipation of any awkwardness, then it's shallow and selfish and it shows they don't really care about you as a person, only their sexual needs at the expense of all other parts of a relationship. Hardly the basis for a healthy relationship. It's no surprise that divorce rates are so high. Don't be ashamed about it, nobody (worth having a relationship with that is) will be turned-off by it.
Can I ask what situations you find difficult, what people you're shy around? If the types of girls with a stuck-up mean look on their face, with a loud voice, bratty, obnoxious and all those other characteristics make you feel nervous, then no-one can blame you. A lot of guys find that uncomfortable (and annoying).
But anyway, what particular aspects do you find most difficult of all? If you could start answering those questions, it maybe of help.