Confidential to Cootie Infested: No, you don't have to "play it cool." Playing it cool is the root of all your troubles; try playing it desperate: Tell your friends that if they don't fix you up with some cute, single guys, you're going to shoot up a Kmart or something.
Confidential to KD: Someone told you your almost 8-inch dick was "smaller than average"?! The average dick is between 5 and 6-ish inches long, which makes your dick above average if anything. I don't know who was measuring you, but he or she was full of shit. You're hung, baby.
Confidential to Queer and Confused: There are plenty of places to meet "good-looking, masculine gay guys who are up for some fun," just not in West Hollywood. My advise for you: Move to a real city -- New York, Chicago, Halifax, Portland.
Confidential to Wish I'd Known: The more information someone has about anything, the better prepared they're going to be for any eventuality. Soooo, buttercup, yes I do think a girl virgin should inform the boy who's about to fuck her that there's a hymen in there somewhere, even if that boy isn't her longtime boyfriend. What reason could there possibly be not to inform him? The risk that he'll bail is slight; he's likelier to be a little more considerate and thoughtful. If he does bail, good riddance: Why would you want such an asshole to take your virginity anyway?