I never have...but think it'd be a lot of fun for sure!

Never actually played dress up before but think it would be fun. I do have a few things in my closet I could use...soldier's uniform, cop uniform, hospital scrubs, business suit, ect.

I kinda like the idea of a naughty nun now that someone mentioned it...kinky!! :D

Of course, I like the old stand-by's too: nurse, maid, school girl, ect.

ME ME ME... i'm sick! *cough*

I've just remembered something from a few years ago.....

Back in my college days I had this very short demin mini skirt which so turned my ex on......it wasn't a 'costume' but it did become something I played dress up in. In the end, I had to throw it out, as it'd been cum on so many times, it became pretty much beyond wear. There's a limit to how much you can wash an item like that without it being totally ruined!

I have never done the dress up thing either, or than teddies and such, But do have a few things in my closet that would work for dressing up if anyone ever told me that they wanted to see me it whatever, lol.
full length fur
school girl
teacher/sec/librarian
cowgirl
nurse
too name a few, still trying to set up a time to do a photo shoot..............