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You see, you mention that you’ve had a handful of chances at one-night stands, but only one real “relationship”. I’m not the least bit surprised that you weren’t able to have sex with your one girlfriend; you weren’t attracted to her at all. Forget the popular idea that guys will fuck anyone when the circumstances are right is a myth; if you’re not into someone, you’re not into them. You have nothing to be ashamed of, GPA. The problem wasn’t you, the problem was that you were dating someone who didn’t make your dick hard. There’s nothing wrong with not being attracted to somebody; attraction isn’t an obligation, and the fact that they have compatible genitals doesn’t mean that you’re expected to get sprung at the thought of it.
Now, following up that experience with those would-be one-night stands was a bad idea; you’ve placed all of the importance on proving that you can “perform”, you psych yourself out and take the experience as more “proof” that you’re somehow defective.
So what’s a guy to do? Well, here’s what I suggest:
First of all, no more one-night stands. In fact, sex is officially off the table for you for a while; you need to be able to enter a sexual situation without feeling that you must perform rightthisfuckinginstantgogogogogo. You’ve gotten so wound up about the destination (getting an erect penis into a vagina) that you’ve lost sight of the journey (everything else). So it’s officially time for full-on intercourse to be set aside while you get more comfortable with your identity as a sexual being. Starting every potential interaction with the goal of getting de-virginized and proving that you’re a functional man is only going to make things worse. So you’re going to need to take things slowly. A one-night stand is only going to make things worse – you don’t need the mutual expectations of sex. You want someone you can connect with and with whom you can take your time.
Now, don’t take this as a recommendation to rush into a relationship. After all, you’ve been there and done that and look where that got you: stuck with a girl you didn’t find attractive with your limp dick in your hand and feeling as though this were all your fault and with undeserved feelings of shame. Don’t try to find someone with the goal of getting laid. Don’t be afraid to be picky. After all, you want to find someone you have a genuine attraction to, emotional as well as physical. It doesn’t have to be a committed relationship; you could just be friends who like to fool around. But it must be a genuine attraction. Don’t round up to “attracted” just because you’re feeling the need to lose your virginity.
When you do find her, you’re going to go slowly. Explain to your partner that you’ve gone too fast before and it’s caused you problems and you want to take your time with her. Don’t be embarrassed by this: if she has any problems with you wanting to take things slowly, she’s not someone you should be hooking up with in the first place. If she cares for you and respects you – and for fuck’s sake, if she doesn’t, you shouldn’t be with her – she’ll understand and respect your wishes. If not… well, even though it may not feel like it, there are lots of women out there. You don’t want to let a scarcity mindset push you into another relationship you don’t want.
As much as you’ll feel the urge to push straight to sex, you need to move at a glacial pace. Spend time just making out and letting hands roam around the outside of your clothes without feeling the pressure to go further. Let yourself get comfortable with her and the attraction you feel to her. Let things progress a little at a time; there is no rush and you need the time to get acclimated to each new stage. Even when you’re to the point that you’re regularly achieving erections in her presence – and you will, when the pressure is off and you’re not feeling as though every interaction is all about having to perform – don’t rush to sex. Get used to being sexual with her without feeling as though you’re required to move to intercourse. You can masturbate in front of each other, you can roll around and perform oral on each other… but you’re still going to hold off on sex until you are comfortable and ready. When you can have an orgasm with her active involvement – whether it’s through her jerking you off, oral sex, using a Fleshlight on you, whatever – then and only then should you consider yourself ready for actual sex.
Even then: take it slowly. Lots of foreplay and stop for a breather or two if you feel your anxiety start to creep up. It’s not a race, and you’re not doing yourself any favors by rushing straight for the finish line. When you get to that point, be sure to make sure you’re prepared and then… just relax. It’ll be a breeze and you’ll feel as though a whole new world open up to you1 .
I know how frustrating this will feel. Don’t – and I can’t emphasize this enough – look for shortcuts. There may well be times that you think that drugs – Viagra, Cialis, hell, even meth – might be the answer. It’s not, and trying to skip straight to sex with the benefit of chemical enhancement is going to be the equivalent of trying to stem a gushing hemorrhage with a band-aid.
The other thing I would suggest is talking to a therapist. You’ve let years of unnecessary shame and self-recrimination rule your life for years now. It won’t do you any harm to have a sympathetic ear there to help reassure you that you can let go of all this baggage you’ve been toting around.
Don’t worry man. All will be well.
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