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I don't even think I have to say it, but don't go with a prostitute. No good, potential girlfriend is going to be weird about 'deflowering' you. Definitely do it with someone you love, or at least someone you are interested in on more than just a sexual level. I lost my virginity at age 18 and my girlfriend was surprised that it was my first time, not because I was 18, but because I tried my best to remain confident. It worked, and that's not because I got some in the end, but because I had a great relationship for a while after that.
Obviously it's popular among young people to lose your virginity early, and all that crap. Don't fall for it, really, whatever you do, whoever you lose it with, and whenever you lost it, that's up to you, and is nobody else's business. In high school you're asked if you're a virgin almost every day. Once you get to college (hopefully your college!) nobody gives a damn. People care whether you're in a relationship, but nobody asks if you're a virgin. You only hear about people losing their virginity early because they're the ones that advertise it (either to brag or to regret it). Older virgins don't advertise the fact, so you automatically think that older virgins are 'abnormal'. The fact is it isn't true, and you don't have to fall for any of the crap about feeling left out. Everybody loses it in the end, so it'll happen, but you want to find someone to share it with.
(Isn't it interesting that people don't recommend a fake vagina, but if a women were lonely, and in the same position as germanguy, and asked here about buying a vibrator, there would be lots of support? I guess it has something to do with the stigma attached to men and sex toys.)
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