Quote Originally Posted by KnottedYet View Post
I'd really suspect sitbone width to saddle width is a major contributor to your distress.
This.

Have a bike shop measure your sitbones (I know any Specialized dealer will be able to do this), and that will give you an idea what width saddle you need.

Cutouts could help, but they won't make a difference if you still buy the wrong width! (My saddles happen to have cutouts, but that's not why I bought them).

And yes, you are correct, no undies with the bike shorts.

Honestly, I've never used chamois cream and never had an issue. My typical ride is 40-55 miles and I have done centuries. Other people swear by the stuff. The cream will help primarily with any saddle sore or ingrown hair issues; it won't help with private area issues that are due to an ill fitting saddle.

Good luck and have fun at the ride