Crying during anal penetration

Just curious if any guys find a cathartic to cry during anal?

Personally I cried from the pain of anal quite a few times, but there was something about the release of crying that makes it better for me. Just curious if anyone has anything similar.

Even without the pain, once when a guy fucked me, and it didn't even hurt that much, but he just encouraged me to go ahead and cry, and it was great to do so.

Personally I like it when the bottom cries. It lets me know I'm doing my job.

I can remember crying a bit the first few times I was on the receiving end of anal. It stung like hell, but with some patience and repetition, the sting wore down and I began to crave a hard cock in my ass.

Only once did I cry during anal….my husband at the time & I were having sex in the shower it slipped out & went straight into my a$$…cried for about 30 minutes hurt to sit down 🍑🍆😭

Aware that I'm straying from the original point just a little but if some woman is kind enough to let, or better still encourage me to fuck her anally I'd be mortified if she cried. I'd want to make it as pleasurable as possible, not reduce her to tears.

Despite a couple of occasions when Mistress had the opportunity to have her way with me anally, she never made me cry. This topic makes me wonder if she was disappointed that was not the case?

Ideally it shouldn't hurt. Having been a long-time "total top" I did lose my anal virginity not that long ago. A lot of time was spent in foreplay. I think he was up to 4 fingers in me before he said I was ready. And he was BIG but it didn't hurt at all.

If I made my sub cry when I took him anally I would stop. It would tell me I was not doing something(s) right. It should be pleasurable, at least that is my view.

Now crying during a spanking...that would be an interest, which has not happened.

OK, I've done it on purpose once. It wasn't a smart thing to do, could have actually hurt me (though the guys tried really hard not to) and was part of a CNC scenario (consensual non-consent). Basically I had arranged to be raped during a home invasion by my husband and lover. They took me anally as part of it and weren't as gentle as they usually were and I did cry. Part of it was the pain, part of it was the intensity of the scenario and what to do if I cried WAS discussed beforehand. They did check in by asking 'OK' (we agreed that a simple OK? was to be the check in phrase as it didn't interrupt the flow too much) and I responded with 'green'. The safe word was 'red' which meant stop everything or 'yellow' which meant 'stop what you're doing and check in further'.

As I said, it wasn't super smart as I could have actually gotten hurt, and there was a little bleeding back there after, but all's well that ends well and I got what I wanted out of the encounter.