I used to masturbate since I was 14, usually once a day, and I usually had satisfying orgasms, but I never had a girlfriend and I didn’t have sex until recently. I just turned 33, and decided to have sex with escorts, but although the two escorts I went to were beautiful, sexy and understanding with me, I couldn’t have proper erections with them. I was very anxious. I felt almost no pleasure during vaginal penetration, I didn’t have an orgasm and I didn’t ejaculate.

So I very much wanna know this:

1) Am I – technically or scientifically speaking – still a virgin if I didn’t have an orgasm with the escorts and if I didn’t ejaculate?

2) Why didn’t I feel pleasure during penetration? Because of the condom? Or maybe their vagina was large and the friction wasn’t strong enough? Because I was inexperienced and anxious? Because of the weak erection? I remember it hurt when they put the condom on my penis, so I don’t think I have an insensitive genital area.

3) So many people say that you don’t really lose your virginity no matter how many times you masturbated until you have vaginal intercourse with a woman, but I didn’t hear anyone say anything about whether you do lose your virginity if you didn’t have an orgasm during vaginal sex. So what is for a man/guy the difference – scientifically speaking – between having an orgasm while masturbating – which is sometimes very satisfying for me, especially if it’s the second one that day – and having an orgasm during vaginal intercourse? Because I didn’t experience the latter. Is that and that only what makes you a non-virgin? Why most people consider that only through vaginal intercourse you actually lose your virginity? Is there a physiological or a psychological difference that only a guy who had vaginal intercourse can understand?


  • Michael Castleman says:

    Thank you for asking your questions. It’s not easy being an older virgin, but I think I can help.

    “Virgin” usually means a person who has not had vaginal intercourse. This standard definition says nothing about whether or not the participants enjoyed pleasure, orgasm, or for the man, ejaculation of semen. Using the standard definition, you are no longer a virgin. You’re a man who has lost his virginity, but who has some sex problems—erection issues and no ejaculation/orgasm.

    Why didn’t you enjoy pleasure or orgasm/ejaculation? I seriously doubt that the condoms had anything to do with it. Condoms are ultra-thin and despite the mythology, don’t significantly reduce penile sensitivity. Millions of men use condoms and enjoy pleasure, orgasm, and ejaculation. So, no, it wasn’t the condoms.

    And your issues have nothing to do with the tightness/looseness of the escorts’ vaginas. If you’d like to learn more about this, read my low-cost article, The Truth About Vaginal Tightness and Looseness.

    You’re by no means alone. Lots of men over 30 are virgins or, like you, have had intercourse a few times without pleasure or orgasm. The issue is almost always anxiety, deep, soul-rattling anxiety. Older virgins usually feel that there’s something terribly wrong with them, that they’re not really adults, that a key part of life is a total mystery to them. These feelings trigger a predictable physiological reaction to substantial stress, the fight-or-flight reflex. The nervous system sends blood away from the central body and into the arms and legs for self-defense or escape. But when blood flow is reduced to the central body, it’s also reduced to the penis. So men under stress don’t have sufficient blood flow into the penis to raise firm erections. If you’d like to learn more about this, read my low-cost article about the Causes of ED.

    The kind of stress you’re under is also the cause of lack of pleasure during sex and lack of orgasm/ejaculation. For more, read my low-cost article on Problems with Ejaculation/Orgasm.

    It’s also very common for men in your situation to have no problem raising erections and enjoying pleasurable ejaculation/orgasm during masturbation. In solo sex, you’re NOT anxious, you’re relaxed and comfortable, so you don’t trigger the fight-or-flight reflex, and you don’t suffer the sex problems associated with it.

    The good news is the you CAN enjoy partner sex, ejaculation, and orgasm. Here’s what I suggest: sex therapy combined with a surrogate partner. The sex therapist can help you relax about your situation, and answer all your questions about women and lovemaking. The surrogate partner can teach you how to both experience an provide pleasurable erotic touch. If you’re unfamiliar with sex therapy, read my low-cost article, An Intimate Look at Sex Therapy. For more about how surrogate partners can help older virgins, I’ve attached an article about that. And if you’d like more comprehensive information about all aspects of sex, you can read my low-cost e-book.

    To find a sex therapist near you, visit the American Association of Sex Educators, Counselors, and Therapists, the Society for Sex Therapy and Research, or the American Board of Sexology. Ask prospective therapists if they work with surrogate partners.

    With sex therapy and surrogate partner work, you CAN learn to have satisfying partner sex. I wish you the best.

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