Relief of Crying: How do I achieve?

I (sub) love the relief I feel after crying (especially if it's the "ugly" crying). A couple of years ago before I started being involved in kink fully, I did a bondage and spanking scene with my vanilla ex, without any knowledge about kink. I ended up crying, and I had an amazing relief thanks to that.

Now that I'm involved in kink very actively (24/7 PPE power exchange dynamics, dungeons, workshops, multiple play partners), I feel fortunate to have different scenes with different people. I am a masochist, and my reactions to pain don't include crying at all, unlike how I experienced it once, years ago. I grin at first, and if I get into subspace, I simply turn into mush, mumble, speak in tongues, or some other subspace behaviour. If the pain doesn't feel right for whatever reason, I just stop the scene.

As far as I've seen, I mostly get close to crying if I feel a lot of pressure under me. On the other hand, I hate failing, and having tasks that I'm bound to fail is a limit. I also don't role play. I'm not affected that much by humiliation, and degradation is a limit.

What I want to achieve is feeling lots of pressure (physical or emotional) without triggering any self-confidence issues or having to fail something, start crying out of that pressure, be embraced by my play partner / Dom in a caring way, and then receiving the sweet and caring aftercare. Any tips?