Well this thread is going to get awkward sooner or later, might as well kick it off...
Speaking as a male rider who does jumpers, there's always going to be the occasional bang against the saddle that's going to hurt. I have no idea what it's like when someone squishes your boobs but I imagine it's the same horribly awkward feeling when it happens to us down there. You quickly learn how to sit on your seat bones and avoid leaning forward unless necessary.
For me personally, I took most of the hits while posting and found that some saddles were more forgiving than others. Eventually, I realized that I was simply rising too high and coming down was where things were getting squished. I can now go weeks without having any memorable incidents but it does happen from time to time. Just last weekend, I had a jumping lesson and near the end I got lazy and lost my balance going over a rail... slammed myself into the front of the saddle and it was the most excruciating pain ever! Needless to say, I won't be making that mistake again.
I never feel uncomfortable riding, but I have to 'adjust' myself before I lead the horse into the ring. A quick look around, make sure no one is watching and then align everything up so it's perfect, lol. This is probably too much information, but you don't want anything tucked under you that doesn't need to be there if you catch my drift. Also wearing boxer briefs, jockey shorts or plain briefs is much more comfortable than loose fitting boxers.