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What I do: I put on my false lashes and eye makeup (not obvious with glasses on) Bra with false tits, jacket over, pantyhose under slacks. Now the tricky part. At Pride parades I use a porta-potty. Or the unisex restroom of an indoor venue. Carry a big bag, strip off slacks, put on skirt, heels, wig, earrings, lipstick, etc.
Did this two months ago in the mens room at Exxxotica. Blasted out fast as possible without making eye contact with the guys in there.
If I have to change in the car I dress from the neck down. Then I only have to put on my wig, makeup and jewelry in the car.
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One time after a day of activities. I had my bag of goodies and stopped at McDonalds. Went into the guys restroom, changed fully into girl mode in the stall. When the room was empty I stepped out, walked straight to the exit and out to my car. No one noticed or said anything. But you could hear my heart beating like a bass drum from across the street.
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One thing about changing in parking lots, most of them are monitored with security camera's. No one may be watching but there is always that possibility.
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This is something I think about alot. I can wear a bulky jacket and loose athletic pants over a dress or a jacket over a blouse with gurl jeans. Put the shoes and wig in a gym bag. Do foundation and eye makeup before I leave the house and wear sunglasses to conceal that. Then I just need to find a quiet parking area with no security camera or a pullout on the side of the road to don the wig, put on my earrings, and my breast forms, change my shoes, and apply lipstick. Though I can do lipstick while I'm driving. I have a couple of spots around here and always keep an eye out for more. If I wear nail polish I have to keep my hands low while driving.
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My car has factory fitted tinted windows to the rear and the back seats. Almost impossible to see in.
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Mostly I partly dress before I leave home and then finish dressing in the car or in public restrooms.
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I am sorry so many of you have to consider these options. I don't always appreciate how good we have it.
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I cannot leave the house with makeup. Since I will wear sunglasses, I may just take lipstick with me. I just picked up the pants and top today. Until I put them on, I won't know if I can leave the house with them under my male clothing or not. The bra, forms, and sandals won't be a problem as I can just put them in the car. Since the bra will be a front closure, it will be easy to put on in the car. I'll be getting dressed in this new outfit later tonight. I can hardly wait. (giggle, giggle)
EDIT: Also, the press on nails won't be an issue. I now have the pants and top on. They fit well. I tried to put on a pair of my wife's size 14 pants which I couldn't do, so I guessed a size 18 would be right. Good guess. They fit perfectly other than the legs are ever so slightly longer than I like them. However, woen are simply higher waisted than men so their legs are proportionately longer than men's legs. At 5.8" I wear a 29" inseam, so my legs are even proportionately shorter than most men's legs. Next up for tonight is to add the hip/butt pads and sandals.
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Sounds like an excellent outing coming up!
A comment about height and inseam. I'm 2" shorter than you with a 29" inseam so I understand what you are saying about proportions. I've found that my figure looks best with a tucked in top. My inclination was to wear my top untucked to hide my lack of a defined waist. But with appropriate padding it seems to give a better look when tucked in.
Also, I shop more in the petite sections of the store or on line.
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I just found the final thing for my outfit - something I didn't know existed. Yep, press on toenails. I found them on Etsy. I've also decided I'm going to take the pants to a seamstress to have the legs shortened. I want them to be comfortable to wear at my normal waist and not up around my neck (or so it feels lol!!). Oh, I can hardly wait. I cannot wear the top or pants under my male clothing when I leave the house, so I will have to be creative when deciding where, and how, to change.
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Whatever you do, make sure you can walk comfortably. Uncomfortable footwear can turn a dream outing into a nightmare and walking awkwardly in female shoes is a notorious "tell" for CDers.
I had this great outing on a national holiday planned to the minutest detail. It almost all fell apart when the heel of my shoe unexpectedly broke off just as I was stepping out of the car. I had to wear my guy shoes in the end.