Kandi, dear:
You have struck the perfect nerve. In sum, I've been taking my interest in women's clothing seriously for only about the last 6 months or so. The long journey to the point of buying my first dress is another story. But in this time I've "come out" to The Wife (of 39 yrs), expanded the wardrobe and become quite brazen in "living the dream"; with good and almost disastrous consequences.
I love going out dressed. Maybe it's the old audacious pilot in me, but I've experienced a joyful exhilaration each time I dressed up and went out into The World. And mind you. This 6'3"/215 lb frame (taller in heels) will always attract attention if it's wearing a dress. Even if I was a natural GG, that tall would stand out. So I accept that. Make myself as pretty as I feel and GO.
The first real time was my long fall bike adventure trip. I dressed at the various B&B's on the trail. I went out one evening to dinner (alone) fully dressed except for my wig (which I didn't wish to abuse backpacking). I wore a very nice silk headscarf. My waitress was fantastic. She was not completely at ease until I broke the silence over the obvious (yes dear, I'm a man in a dress). After that she took care of my like royalty. Bought my wine. Poured out heart heart over her LGBT friends, etc.
I was also well received by the breakfast cook at another B&B I stayed. I was the only soul present. I believe I surprised the poor woman knocking along the hardwood floors in heels to the dining room, only to see a tall man in a dress and makeup. She, a retired teacher making extra $$ on the side as a cook, taking care of grandchildren. She whipped up a great soufflee and fruit cup, and we enjoyed the morning showing photos of grandkids.
The rest of that trip went great (except the night I locked myself out of my lodging while I was in a dress and heels).
I ventured into The World last Oct to have a makeover at ULTA. A fantastic and encouraging experience. I'm dying to go back.
I dressed up (in my favorite and "hottest" green dress) and strolled a mall and a dept store. The SA's in Macy's made me out relatively soon. As soon as one came over to check out the Very Tall Lady, I bet I was approached 4 more times. I made it around the jewelry counter and the make up counter with ease, and even engaged one of the artists (in my male voice, as I was obviously a cross dressed male IN GOOD MAKEUP, BTW) for a short discussion. She did indeed crack a smile, but a kind one.
The best place "dressed" I went was to the local Colorado "dispensary" [if you know what I mean]. The women at the front counter know me in my "rugged" male athlete (but kind of weird guy) form, and they love me. What a hoot it was when I walked in dressed in my green skirt, lace top, heels ... the works. We had such a laugh and fun about it. Now she knows I'm crazy. They both thought I looked great AND mastered walking in my heels like a Jedi.
The S.O. isn't too keen about the "going out" business. I've told her about a couple times. She wasn't with me and she's stated she has no interest in going out WITH me while I'm dressed in my Lady Clothes. Yet I am quite attracted to the notion of going out. Don't know why. Maybe it's the (safe) danger of it. The audacity alone is alluring. Maybe it's the "secret identity" part of trying to mingle in the Normal World. Or maybe it's just the damn pleasure of letting go of your psyche, feeling good and having to confidence to just go out into The World as YOU, and truly not give a ratzazz about what they think.
