This question comes from a point of real frustration. I'm a 26-year-old straight guy. Due to my being overweight, awkward, and generally unable to attract women I'm actually interested in, I have only been sexually intimate with prostitutes and women of low caliber. I have never been able to sustain an erection during intercourse. I've climaxed during oral sex or handjobs. I'm not physically accustomed to getting off with anything but my hand. Worst of all, the intense fear of impotence has caused me to avoid sexual liaisons. When dating, I feel threatened by the expectation of sex within the first few dates. Any solid advice?
Sick Of Beatin'
Join a gym and lose some weight. You'll gain some confidence and improve your health — and your circulation — which could help in the keeping-the-dick-hard department. (I'm not telling you that you have to transform yourself into a muscle god to be happy or find love.) Seeing a doctor and getting your hands on some Viagra couldn't hurt, either. Vary your masturbatory technique.
Stop sleeping with women unless you're attracted to them on some level, and recognize that holding the women who will sleep with you in contempt is an expression of self-hatred and knock it the fuck off. Since sex within the first few dates makes you feel anxious, inform anyone you date that you're not up for having sex within the first few dates. And the next time you find yourself in bed with someone or sense that things are headed there, SOB, tell her that you're really only interested in oral and mutual masturbation — at least at first — and that you generally take a long time to come. Then you don't have to stress out about failing to meet her expectations, because she won't be expecting anything other than what you're capable of delivering.
Finally, there are sex workers out there who will not only get you off in exchange for your money, SOB, but will work with you on improving your skills and building up your confidence. You may have slept with one already without realizing it because you so resented having to pay for it that you dismissed her as a cheap whore to protect your ego. Dumb mistake.
I'm a heterosexual male. I've never been in a long-term relationship, I've never been in a short-term relationship, I've never been in a relationship. Four make-out sessions in my youth and paid sex with cheap street prostitutes is all the physical intimacy I've ever known. And sometime before the end of this year, I'll be turning 45. I have no explanation for how I fucked up something this important this badly for this long, but here are my best clues: 1. Deep down, I don't think I've ever really believed women could possibly find me attractive; 2. For me, being rejected and/or humiliated after approaching someone is an almost paralyzing fear; 3. My professional/career/financial situation is only slightly better than my romantic/sexual situation: I'm always either barely getting by or in some crisis where staying non-homeless is my only priority.
I want to understand what the fuck is wrong with me and why I'm staring at a lifetime of totally unfulfilled romantic and sexual hopes and dreams. The last thing I need right now is some Pollyanna bullshit. I want brutal honesty.
A Lifelong Onanist Needs Explanations
Some people are alone all their lives because they're too damaged or too terrified or too terrifying, ALONE, and some people are alone all their lives because they are simply, as the cliché goes, unlucky in love. It sounds like you suffer from social and sexual anxieties — damaged and terrified — and could benefit from seeing a shrink. You say you're barely getting by, ALONE, but if you're spending money on cigarettes or booze or pot or all three, well, you might want to prioritize your mental health over those nonessentials.
Here's what you need to do between now and death: Keep a roof over your head, put food on your table, get some help with your emotional problems, and take your pleasures where you can. Do things you enjoy — alone, if you must — and you might meet someone along the way.
Or not.
And if the only intimacy available to you is paid sex with cheap street prostitutes — or, as they prefer to be called, "conveniently located and economically priced sex workers" — that's better than nothing. Remember: Sex workers are part of the solution for you, if not an entirely satisfactory solution, so have a little gratitude and treat them with respect.
