I'm almost 30 years old, male, heterosexual — and a virgin. I've never even kissed anyone on the mouth. It's not for lack of desire; I just have always been shy, overweight, and not well-endowed in the masculine sense. Now I'm terrified that I've missed the sexual boat and there won't be another one. I don't think I would be able to hide my inexperience in bed, so if I do become intimate with someone, I would have to tell her, and I am afraid that would cause any potential partner to lose interest. I also have the problem that my desire for young women has never been fulfilled, so it nags at me. It sounds terribly shallow, but I don't want to get old and die without ever having sex with a 22-year-old woman. Yet I also don't want to be a dirty old man, going after girls who are way too young for me. I would appreciate some advice.
I totally get it. I wouldn't mind having sex with a 22-year-old woman before I die, either.
The good news is there is no sexual boat, just as there is no social train, spiritual Smart Car or… I don't know… professional airbus. I swear there isn't. That is a really terrible metaphor for something that doesn't exist. People have sex when they are intensely, achingly attracted to one other. They do it as teens, as old people, and at every age in between — and they all have a first time.
More good news: Sexual experience is overrated. You'll have to take my word for this, but plain old frantic, fumbling, basic-biology intercourse feels crazy, ungodly good, so you don't get a ton of bonus points for having "moves" or encyclopedic nudity know-how.
But some of your excuses are lame. You could go a long way toward turning "overweight" into "ripped hottie" if you really, really wanted to, and the size of your, er, masculine sense probably isn't an issue for anyone but you.
I’ll give you one thing, though: Confidence is sexy. And if you absolutely can't muster any without having some sexperience under your belt, then quitcher whining, go to Nevada, and pay for it. (Spare me the sanctimony: Ask your grandpa about HIS first time).
Then stop thinking of sex as a checkbox and start seeing it as an opportunity to connect deeply with someone who's drawn to you for the thoughtful, honest man you clearly are. Maybe it'll even be someone in the same boat.