Don't feel bad. It's happened to all of us. I also tried my new stock saddle--because DH said it looked cool (it was white). Nothing hurts more than road rash down there

Definitely no underwear under bike shorts!

When I get over 25-30 miles, my "regular" bike shorts aren't enough. I've invested in some more expensive SheBeest for longer rides.

Chamois cream can't hurt to minimize friction, but isn't necessary.

Saddles--whew! I believe there is a forum just for saddles. It's a very personal choice and involves trial and error. I use a Brooks.

After chafing down there, my SheBeest shorts and Brooks saddle didn't seem like such an expense