Here's my question. With a bunch of convoluted background to preface it...

I'm going trough some pretty crappy break up type stuff right now. Married almost eleven years. Separated for about a year and a half. Pending divorce. Long story, bad marriage, I was too young, he's not really that nice... blah blah blah

Been messing around with another guy for well over a year. This other guy is married. It was a bad call on my part. But it's been going on nonetheless. Truth is, I think he's a dick. I like the attention he gives me (even if it's not as much as it should be), but he really is just a selfish prick. I know this. And I'm trying to just stop seeing him. I'll get there eventually.

But here is my actual problem/question, now that you have a little background.

I've noticed that after masturbating (maybe to a little porn), I'll come just fine... but then I start to cry. WTF is that? I go into these masturbating sessions wanting to come, wanting to get some release, but then I start to cry right after I do come. I have been dealing with some depression issues—for all of the above bullshit—and I've noticed that I cry a little more than I used to in other circumstances. But this after orgasm cry fest? I don't get it. Can you help?

Cry Baby

I don't know if this will help, CB, as it's just a little something I yanked out of my ass. Meaning, no data, no research, no psychological experts weighing in.

You typically watch porn when you masturbate, projecting yourself into the fantasy scenes and scenarios on your computer or phone. (Who watches porn on the teevee anymore?) Or you lay back and fantasize about the sex you'd like to be having while you use a vibrator. Your fantasies—whether augmented by porn or entirely your own creation—remove you from your current reality. You don't watch porn featuring your shitty soon-to-be-ex-husband, you don't lay back and fantasize about that married jerk you need to stop fucking.

And then you come.

The fantasy ends, the orgasm(s) subside(s), and it's back to reality. Your current reality, CB, which ain't so great. You're already feeling a little emotional as your not-that-great marriage ends and this not-that-great affair continues—those tear ducts are primed—and the combo of those already heightened emotions and the contrast between your sexual fantasies and your current sexual/marital/relational realties is just too much. So you have yourself a nice, cleansing little cry.

My hunch: once you're no longer married to your not-so-nice husband, CB, and once you're out from under your selfish prick of a lover, the contrast will be less stark and your masturbatory sessions will no longer end in tears.