So.. I feel like I've got my foot on the gas with crossdressing! I had my first femme makeover last week and another one two days ago. After the second makeover, I decided to wear everything back to my hotel.
WOW. What a rush!
To give you an idea, this is what I wore out of the studio. Natasha at My Changing Room in Boston was incredibly supportive and allowed me to keep all of these beautiful items.
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Now, I unfortunately had a very un-femme jacket with me - it's an olive waxed cotton outdoor coat from Barbour. Not too good of a match to this breezy and light outfit, but it was almost 40 degrees out.
My very first public appearance was walking outside the building - along quite a busy road - back to my car. I'm not really sure why, but I have a pretty innate ability to wear heels. I was a little unstable in these 5" platforms at first, but got the hang of it quickly. Despite broken pavement and such, the walk was very manageable. Not sure how I looked from the road - it's probably not everyday that a 5'10" woman in platforms and nude fishnets goes for a walk in a parking lot at midnight.
Anyway, I took off down the road back to my hotel. Driving was very exciting. I took my shoes off and drove barefoot for safety's sake. And then.. it turns out that there is a toll plaza! So my very first presentation as a woman was to a fairly nice young dude in a beard who took $1.50 from me. I choked a little bit with talking, as I have yet to attempt a femme voice, but I smiled and mouthed "thank you" after getting back my change. Ultimately it was no big deal.
The bigger deal was the hotel. It was pretty late, so I figured that the lobby would be empty save for a night employee or two. And regardless of my body or makeup, I was going to stand out because no woman in her right mind would ever wear my jacket with that skirt and shoes - not to mention on a night when it's way too cold for such an ensemble. I was going to just own it, but got nervous at the last moment. I took off the heels and put in my Nike's so that I could move faster. I walked into the lobby, and smiled at the girl behind the counter. She looked down, but I think that was more to avoid embarrassment for me - I must have looked very nervous. I bet this isn't the first time that she's seen it either.
After I got into my room, I vamped in the mirror for a bit and changed. I tried to remove the makeup, but couldn't get the eyeliner off with some vaseline. Which they sell in a little area next to the front desk. So I walked to the desk in guy mode, but with lots of liner and shadow still on my eyes. I wore the same sneakers as before. The girl was polite to me, but neither of us brought up anything around the situation. And I went back and fell asleep, blissfully.
Thanks for hearing my story! It felt great, and certainly felt like something I can do. I recognize that my tastes as "Eva" are skewing towards the kind of sexy clothing and looks that I've always liked on GG's, so for me to pass more, I'd have to be more casual. I love fishnets, but I can count the number of fishnets that I see on GG's (well, outside of Halloween and Nightclubs) on one hand. I'm thinking to shop at a store like MadeWell and get something along the lines of chino shorts, sandals, and a girl's army jacket. Wear it with bare legs and see what happens. I'm probably too built to pass physically, but I'm not really looking to. I guess that I'd just like to be me, and look like someone who's indulging his femme side, not wearing something very revealing for attention.
I'll save revealing attention seeking for photoshoots and CG/TG events! Roar!! :-)
congratz on the first time out, it is quite a rush, now youll want to do it more,
crossdressing...theirs an app for that 
, You look absolutely gorgeous, You are out there now, there's no turning back now. 
