I was exactly like you, The_Shnitz. I was afraid of dying a virgin, and I lost it one day before my twentieth birthday. You bet your arse I played the birthday card to chat up that girl.
What changed my life was seeing a psychiatrist and then seeing a therapist.
Flame away, brothers.
I knew I was an unhappy, bitter person, and hadn't a clue what to do about it. Thankfully my University has a very good student health program that covers psychiatry. In very little time I was given medication (which I am still on) for social anxiety.
It was as though the walls separating me from people were obliterated totally. I was not a social butterfly, nor am I currently--that takes practice--but I wasn't afraid anymore. I had this magical ability to use words to express myself around strangers and females.
And no, taking medication is not an "easy way out". This is because it is NOT a way out at ALL. The real "worK" is in teaching yourself new lessons and learning new ways of thinking, which is something you do in everyday life and with the help of a therapist (which by the way, insurance can also cover.) Medication simply ameliorates one's biochemical disadvantage.
It amazes me how negative so many people are about psychotropic drugs, particularly those similar to Prozac. These drugs do NOT make you a lethargic listless smiling zombie, and they do NOT take away who you are.
If you have a hard time talking to people and feel depressed often, it's worth a shot. Look into it.
And furthermore, I say OWN your virginity with confidence and enthusiasm.
Don't bring it up if you don't have to, but if a girl ends up asking you, it is MUCH better to divulge the truth with CONFIDENCE and a SMILE than seem ashamed and backed into a corner. If she asks why, just say it isn't the most important thing in your life, and you haven't met the right girl. And then on with the conversation. The important thing is that you are warm and comfortable with yourself. If you're not weird about it, she won't be, either.
End of rant.