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BlochWave
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Conclusion: Yah, after reading this the next morning and the responses, the only insane thing about me is that I even typed all that up. I'm just gonna calm myself the hell down. The one guy who kinda busted my balls about clearly being overly self analytical by writing a 45 page thesis on how I'm totally not kinda gave me the necessary e-slap to realize I'm being overly ridiculous
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Yeah, you're overthinking it. You gotta just act. Like ripping off a bandaid. You think she's ready for a kiss? Then just rip off the bandaid and kiss her. Think she's ready to go a little further? Rip off the bandaid and just do it.
the "no true scotch man" fallacy.
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Secondly, the only advice that I have for you is that you have to wait until it feels right. And I know you probably hate that advice because its so obvious and general, but truly, thats all it really comes down to.
I was in a similar position to you. I was shy in high school, and actually didn't have one relationship throughout. Enter college, and I'm presented with a few opportunities to have sex, but I pussy out each time. I get scared, or nervous, or whatever, mainly because of my lack of experience with women.
Enter my current GF. With her, I didn't feel any nervousness. I knew she would accept me completely, and by the time we advanced to the point of having sex, it felt right. There was no nervousness, and I wasn't scared at all.
You have the fear of being rejected or humiliated because of your lack of experience. Once you find the right person, you won't have to worry about being rejected or humiliated because you know they will accept you either way. (A good side effect of not being self-conscious is that you'll be a lot better in bed as well.)
So, yeah. Its probably better that you didn't do her that night. Try and get to know her. Establish a relationship before the sex comes, and if shes the right girl, it'll be fine. If not, continue your search.
Good luck, dude.
Just for sake of clarity...don't ACTUALLY rip off a bandaid before kissing her. That's kind of icky...but some girls might be into it.
That said, Feral's right. Read the situation as well as you can and go for it. The worst that happens is that you'll be rejected and embarrassed and, well, join the club. It sucks, but just about every guy has been there.
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Don't freak out about being inexperienced, either. Every girl I've ever known has had some hilarious stories about guys who, despite having been with many girls, obviously didn't know what the hell they were doing, and they always sounded much more embarassing than any "devirginising" story I've heard. So don't think just because you're inexperienced you're going to be the worst lover this girl ever had, or something.
Except there's nothing tremendously abnormal about you. You feel self-conscious and sometimes feel compelled to lie in an attempt to make yourself seem normal? Tons of people feel like that. You're starting to experience emotional intimacy (you shared the truth when prompted with this girl) and that along with the potential for physical intimacy makes you feel intimidated? Yeah, NORMAL. If I had a nickle for every thread where some male OP had a problem that originated from the urge to deflect during serious conversations about relationships with a potential girlfriend....
Whether or not you have sex with this girl eventually is frankly neither here nor there. It'd probably help more if you actually realized that the huge problems you think you have are neither terribly remarkable nor uncommon. Start wrapping your head around that; in the meantime, keep exploring emotional and physical intimacy with this woman. She sounds nice.
I don't think anyone interested in you personally is going to think less of you because you haven't had sex yet. Especially since its not that you're making a big deal of it, you just haven't had an opportunity you'd feel comfortable with. Don't worry so much about being honest, sure there are a lot of cultural messages out there suggesting that manly men are men because they been doin it, but the reality is, that that is not what makes a man, so it is totally okay to be manly on your own terms.
Be open, be willing to explore, and realize its okay to ask for direction- as long as you share the initiative as well. It will, unfortunately, likely be put on you to get the ball rolling. But once you've shown an interest and a desire, where that ball goes can be an open and awesome discovery process. Also, don't think that just because you haven't done something doesn't mean you don't have talent- a lot of this stuff is basic instinct; if you're really into her, let your body speak for itself, it usually does a pretty good job.
But part of not worrying about it means not feeling the need to have sex just for its own sake. In other words, don't pressure yourself to hook up with girls. It's much better to actually build up a relationship first. And if the girl is someone who is worth having a relationship with, she won't care that you're a virgin.
I distinctly recall rolling off my first and thinking. You got to be kidding me. That's fucking it? All that bull shit for that. Christ what a fucking rick roll.
Granted don't get me wrong sex can be pretty awesome and magical too. Just when you put it in perspective it is really not as important as you think it is.
Also sex with some random girl is usually not as good as it is with someone you actually care about. (usually sometimes its better!)
It's way better to just say you're inexperienced and enjoy what comes, instead of lying and saying you've gotten laid before and then having anxiety the entire time that she's going to figure it out.
Not only that, but like some of the other people in the thread said, it's pretty obvious when a guy has no clue about what he's doing and if he's claimed he has experience/lots of experience it just makes him look like an ass -- usually enough to halt the proceedings.