Now, I'm not one to go out in public in heels in guy-mode to be seen.
But I do enjoy walking the trash down to the apartment dumpster, it's a 20 minute walk round-trip.

Just about 45 minutes ago as I was chilling in some Mary Jane heels, pajama pants, and a hoodie when I just decided to.

So leaving the heels on I changed into an ankle-length black skirt, keeping the blue hoodie on of course.
I had already been wearing the heels for hours at this point.

These were the heels:

https://www.crossdressers.com/forums...els&highlight=

I headed out at about 0520.
A few cars passed, no biggie.
As comfy as the heels are, they do become a little pain on the return, but I obviously don't mind.

Share your such adventures.