Had my first crossdressing experience on Monday (unless you count hoop earrings, many men wear the gender neutral kind you find at Target).
I was at the mall and was looking for a bodysuit or one-piece swimsuit. had always been curious. Anyway I found some leotards at Forever 21 that I passed on because they looked far too small for "my friend" for whom I was buying a gift. (wink wink) Then, found a sale on Dolfin one-piece swimsuits at Scheels. So I bought one, guesstimating my size. Well, upon taking it to another store's dressing room and trying it on (with underwear, of course, I'm not a barbarian) it was too small, even the next size up, a 40, which was their largest size, was not tall enough as I'm around six feet. So I returned it.
I ended up buying a 'skater skirt' in dark silver from Pacsun. I put it on and absolutely loved it from the first second, and not only from the crossdressing point of view. It's just plain comfortable! Why didn't the whole 'kilt' resurgence take off? Guys just don't know what they're missing.
Of course it doesn't feel quite 'complete' in Hanes briefs, from a crossdressing point of view. I'll have to pick up some more essentials. Any Ideas? I managed to smuggle the skirt home under my mom's nose (she drove us) with the simple expedient of bringing a day pack. I'm becoming quite the 'personal items' smuggler.
Anyway, this is my intro to the crossdressing side of the site. What would I call myself? I don't feel childish, maybe 17-25-ish. I don't like the sound of the term "sissy". Always reminds me of bondage and dom/sub, which isn't really my cup of tea. Somewhat tomboyish, hence why the name 'skater skirt' jumped out at me. I like the name Ester, too. Classy yet unusual.