I think you may be missing something in your guesswork analysis of PENSIVE in this week's "Savage Love."

My reading is that this is a man who by his own admission seems to define some of his worth by his willingness to work really hard to give the women he has sex with orgasms—or at least that seems like a not unreasonable possibility, given the way he seems to be conflating his enjoyment of working so hard to satisfy his partners with his supposed feminist values, which the tone of his letter seems to indicate he considers to be good and worthwhile. By extension, his holding those values may be part of what gives him his sense of self-worth or of being a good guy or whatever, and that's before even considering how the idea of being able to get women off is often so caught up with straight men's feelings about their power and masculinity.

Note that I said the idea of getting women off, not necessarily the actuality of it; men who pay for sexual services can go a lot of different ways when it comes to women faking orgasms, with some not caring if a woman fakes it as long as the illusion of her pleasure is sufficiently maintained, and others hating it because the thought that they can't genuinely please their partner makes them insecure about their manhood. (As well as some who like knowing she's faking it without believing the illusion at all because they enjoy the feeling of power it gives them to know that she's putting in the effort, but this isn't intended to be an exhaustive list and hopefully you take my point.)

Anyway, obviously there are multiple reasons in addition to the above that people may like or dislike their partners faking orgasm, but one other big reason to dislike it: it's dishonest. In a sexual relationship that includes emotional attachment the dishonesty might be problematic because it's a barrier to intimacy, but I know there are a number of men who prefer keeping their paid sexual encounters more businesslike transactions for the same reason—that is, not just because it's less intimate, but because the honesty of both parties acknowledging that it's not about the woman's sexual pleasure means that pleasing their partner is one less thing the man has to worry about. And for someone as invested in working hard in bed to the extent that PENSIVE is, the idea of NOT having to work that hard for once might be really freeing. I mean, she has zero expectations that he should even be trying to get her off and she is totally okay with that—okay with it to the point where she's taking phone calls while he's fucking her!

So rather than simply eroticized self-hatred (which I'd also guess was in the mix), maybe another aspect of what made him enjoy the experience so much was that her answering the phone showed her matter-of-fact acceptance in a way that let him BELIEVE she was okay with him not doing any of the work he usually feels like he has to do. I can see how his being able let go and believe it could be okay for the sex to be all about his pleasure and to be so comparatively EASY—and that that wouldn't make him a bad person or bad in bed or inadequate as a man—might have been such a relief that he would come in twenty seconds as a result. Although it cracked me up that after the endorphins wore off, his question to you was about whether his enjoyment made him a bad FEMINIST... because naturally his biggest potential concern with whatever deep dark secret beast he's worried he has buried in his psyche is that heaven forbid his POLITICS might be wrong. So thank you for calling him out on that, which I always appreciate reading.

All the best,

D.

P.S. Oh, and it occurs to me that his apparent failure to consider that there may be many women who really like a good old-fashioned “Wham, bam, thank you, ma’am!”quickie now and again just as much as men do may speak to some notions of women that are a little outmoded and not particularly feminist, but that's neither here nor there.