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Yeah... so when it comes to sex, I firmly believe that there is no such thing as normal. If you were to take a mean average of the age at which people lost their virginity, you'd probably end up with mid to late teens. But there are folks who go much later and folks who go much earlier. Statistics are meaningless.
In terms of sex being or not being a big deal, well, yeah. In some ways it is; sex is a crucial part of a properly functioning relationship and it has some potential life-altering consequences. That part is a big deal. Actually having sex.. well, before I did the deed, I had sex built up in my head as this absolutely amazing experience. Then I finally did it. Yeah, it was fun. Yeah, it was cool to have that kind of a connection with another human being. But there was a part of me that sort of thought 'wait, that's it?' I'd built the experience up to the point that the reality didn't meet my expectations.
You're not going to be a super stud out of the gate, because nobody really is. It takes time to figure things out. And then, once you've got it figured out you end up having sex with someone else and you have to figure it out all over again, since no two girls are the same. And the bottom line is that so long as you both enjoy yourselves it doesn't really matter anyway.
So, onto the Dear Marrsy advice column.
The biggest thing I get out of what you've written is that you're not being terribly pro-active about the whole thing. The problem with the 'sit back and let it happen' approach is that you're basically waiting for that right girl to come to you and that may end up being a long wait. What you should be doing (assuming, of course, that you don't want to just wait) is getting out and meeting people. It's fine that you don't like the bar scene, so long as you realize that that means that bars are probably a bad place for you to meet girls. So find good places to meet girls; join special interest groups, go hang out at the park, go to an art gallery or a museum. And once you go that place that captures your interest, don't be afraid to talk to people. So what if you were picked on in high school? You're not in high school anymore and by all reports you definitely have your shit together. If you were so inclined you could now be the one who picks on people, but seeing as that's probably not you, you can instead take that and turn it into confidence. You are educated, sophisticated, financially independent. You have everything going for you. So take the bloody chance, find a girl you're interested in and start up a conversation. If things go well, ask her if she wants a bite to eat. Or if she wants to catch a movie or go sing karaoke or what have you. So long as you're not offering to show her your hard drive or anything odd like that, you'll be fine and the worst she'll do is say 'no, thank you.'
Personally, I tend to prefer honesty as a blanket policy, since it means I don't have to keep track of what I've said. Plus, if you fabricate some story up front and things progress to an actual relationship, any lies you told in the beginning have the potential to come back and bite you in the ass. Keep in mind, however, that honesty has it's limits. You can feel free to leave stories about your teenage acne or the list of names the meathead jocks called you in high school until at least the third date. Or, y'know, leave them out entirely. Your call.
And if you meet that right girl and things progress and you do end up in the bedroom, then you definitely don't want to fabricate stories about your experience. You don't want her to come into it expecting that you'll be a super stud, since as I said above you almost certainly won't be. It's okay to tell her that you're a virgin; abaya found it charming and I think that's the general response, although perhaps some of our female members can chime in on this. Again (and this probably goes without saying, but) this is the sort of thing that you'll leave until things have progressed to the point where it becomes relevant information. Feel free to leave it out of your introduction.
Your penis doesn't know the difference between your hand and a vagina as, contrary to popular opinion, it does not actually have a mind of it's own. You know the difference and when you finally experience the sensation of a vagina, you will feel a distinct difference. It's highly probable that the biggest difference will be that her vagina is either tighter or looser than your hand normally is. Also of note is that I have yet to meet a girl that is able to give me an orgasm equal to or better than the ones I give myself. Sex is fun because it's a team sport, but going solo means that you have a direct feedback loop which results in a better overall response. And after all of that, if you do last a very long time or are even not able to finish, it will likely be a result of nerves. Relax and have fun. If it comes to the worst and your first time experiencing sex results in an accidental discharge, you can follow it up with your first time experiencing cunnilingus and/or mutual masturbation. So long as you both have fun it's not going to matter.
So, I think that about covers it. Any questions?
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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