Cross-Dressing Inline Skating Adventure

Hello,

I am mapping out the plan below. I intend to skate a fair distance while cross-dressing (CD). My outfit will include a white Nike tennis skirt, an unspecified top, light stockings, and inline skates. Makeup is off the table for now because my wife doesn’t have any yet, and I don’t want to be rude by handing her mine; besides, she always insists she looks wonderful without it—and that’s actually true.

I won’t wear this outfit right out of the house. Instead, I’ll drive there, change in the car, and leave a spare key about 10 miles away. Since I am fit and competent at skating, protective gear isn’t necessary.

I plan to do this during daylight hours, which will be my first time doing so.

That covers the basics.

However, I have some questions regarding clothing choices since I am new to CD. Right now, I only own black string underwear and bras. Would it look odd wearing those under a white skirt? Also, I have semi-long hair that I plan to style in a very feminine way. I found but any other tips for making my head look more female are welcome.

Any further suggestions?

I probably won’t use bondage because if I fall, I don’t want it to be fatal. However, I will likely wear a nipple clamp.