Mistress Measure could certainly make you whimper and beg for mercy, but you don't necessarily cry in that situation.
One woman who made me cry a bit was a huge escort I wrestled long ago. She was neither an fbb type nor a bbw, but a big solid 6 foot women of 220lb plus with a large lumpy body that became really hard when clenched around you.
We wrestled on the bed and it was no contest. She just grabbed hold of me and threw me down each time, pinning me down as long as she felt like it.
She said she also worked as a bouncer and I could believe that. She wasn't actually rough or nasty, but very dominant and in charge, and I had the sense to be appropriately submissive towards her.
It was my first experience of a stronger woman and I quickly forget I was wrestling a woman. It was more a case of just being caught up in a desparate struggle and being manhandled and roughed up by a huge brute who could have done whatever they wanted to me and the humiliation at how helpless and submissive I was (she even forced me to say she was more of a man than me) made my eyes sting a bit.
After one brutal headlock that left me gasping and flushed, a few tears rolled down as I gathered my breath. I lied that I wasn't really crying, it was just my eyes watering, but we both knew I was at my limits.