Dear Mistress Maeve,
Over the last few months I've become vexed by my inability to ejaculate while receiving oral sex. In the past I've dismissed this problem, but I recently had the same partner for over a month, who, by my estimation, was extremely good at it. No matter what she did, no matter how "on the mark" she was, I couldn't get comfortable enough to come. Sometimes I would even experience physical pain, even when she wasn't doing anything abrasive. Eventually I'd always just give up and return to intercourse.
It has also occurred to me that I perhaps have some childhood trauma to work through with a therapist. It also doesn't help that I don't keep partners long enough to really make any progress in this department.
Yours in frustration,
First and foremost, when someone says they "perhaps" need to see a therapist, it usually means they should. Kudos to you for facing your childhood trauma and seeking help. You'll be in good company — most of my favorite people are in therapy.
While you're tackling the bigger issues, remember that relationships cannot get to the next level unless both partners show some vulnerability. If you're still seeing this woman, communicate with her. Let her know that she gives great head and that your issues have nothing to do with her. If you start letting partners in, you may be able to end this cycle of short relationships and make some progress with intimacy. Who knows — maybe you've reached a point in your life where intimacy trumps oral when it comes to getting off?
Above all else, remember that sex is supposed to be fun. In the end, do you really care how you come? You talk about giving up and returning to intercourse like it's a death sentence — I can think of far worse alternatives. I'll bet you'll have a much better time if you stop thinking about the things that don't get you off and start focusing on the things that do.
And one more thing: If pain during fellatio persists, see a doctor.
Best of luck,