Orgasms during Intercourse: A man’s perspective

Dear Sex Educator,
Do all women really have some “miracle” lover hidden somewhere in their past, or is it just fun to make a man feel inadequate? I recently broke up with my girlfriend and I must say, the relationship left me feeling quite inadequate. One of my biggest problems was that she never had an orgasm with me during intercourse. Yes, she could have them from oral sex, but only that.

Now, all this would have been fine if she didn’t tell me about the wonderful, mind-blowing orgasm she had “only once, with this one guy, during intercourse.” This, of course, only made things more difficult for me. And even when she did have an orgasm with me, and I started to feel good about our sex life, she would always say, “Yeah, maybe next time you’ll be able to do it to me with your penis.” Of course, she was referring to an orgasm produced through intercourse, which had only happened one magical time with a guy she said she “couldn’t remember”.

Interestingly, this is not the first time this has happened to me. I have always been the kind of guy to try to discuss all aspects of a relationship with the women I date. But I am starting to see that even though women constantly talk about how they wish their boyfriends could be “more open”, etc. they take advantage when men are open. Why do women want to do this to me?


You appear to be caught in several difficult traps that result from misinformation, and cultural socialization. I want to address the misinformation part first.

Unfortunately, many men and women have been taught that the best orgasms that a woman can have are those that happen as she is having sexual intercourse with a man. Many men and women are taught, and believe, that all other orgasms are inferior. While many men and women no longer believe this to be true, I still encounter people almost daily who do believe this. The truth is that, anatomically, it is difficult for women to have orgasms from penetration alone, and most require additional clitoral stimulation by a hand or a vibrator in order to have an orgasm during intercourse.

It’s likely that your previous girlfriend was so aroused during this one encounter that she had an orgasm during intercourse. The thrill of anonymous sex, or even sex with someone one doesn’t know well, can add a lot of charge to one’s arousal and increase the overall intensity of the experience. This is most likely what happened, and unfortunately she was persisting in trying to replicate this peak experience – which is most likely a rare occurrence.

It sounds as though the dynamic between the two of you was negative enough that she got some pleasure out of poking fun at you with those comments comparing you to her nameless lover – which was something that was very hurtful to you. Keep in mind that while you do have something to do with the pleasure your partners experience, I also believe that women can take responsibility for our own orgasms by learning what stimulation feels the best, and then asking for that, or providing it ourselves.

With future partners, your part in this can be to ask what feels best and how she wants you to touch her. Have her show you what she likes, if she can, so you don’t have to guess. Intimacy should be a process, not a game; both of you can take responsibility for making sure you are getting the most out of your intimate encounters.

As for what may be happening when you try to open up to your partners … that’s going to be hard for me to know. Since all of us are socialized to certain relationship patterns, it may be that your partner asks for something but is not really ready for it when it happens. Or it may be that you are misunderstanding what your partner is asking for, and offer more honesty than she really wants.

I want to urge you not to overgeneralize to all women. No, all women do not have some miracle lover in their past. Some women, and men, have peak experiences in their past that they try to replicate. The nature of a peak experience is that it’s hard to repeat, even though one may want to. You may want to look at how you interact with your partners, and work to be more confident with yourself and your skills, so that you are less vulnerable to those kind of comments.

You have had some unfortunate experiences, but I assure you that many women are seeking a supportive partner in life, not someone to berate and cut down. I hope you find a partner who is more of the former, and none of the latter.

The Sex Educator