First butt boils and now bleeding nipples?! I'm scared to see what page three will have next.
In all seriousness though, I hope you get better soon. My personal experience is as follows. I used to ride about 20 miles in regular street clothes and would be ok so long as it wasn't 90 degrees or hotter. Then I started using regular compression shorts and was fine for 30 miles in any kind of temps. I also found that if chaffing was happening or was a frequent occurance I could "Splash" baby power down there and it would take care of it. Now I have graduated to actual bike shorts, ones with minimal padding, and have ridden up to 50 miles in 100 degree temps and been just fine. My next purchase will be bibs since so many people here on BF swear by them.