We all know that Halloween is pretty much a crossdresser's dream holiday, and it probably takes less balls (pardon the analogy, but the irony was too much to pass up) to go out for the first time on Halloween weekend than other times of the year, but that was when I first worked up the nerve to go out in public dressed up, just this past year.
I have dressed in private much of my life, going through the typical hid it, purge, don't tell girlfriends, lifelong game of denial until my current relationship when I just went with it and told her a couple years ago. I got lucky and have a supportive significant other (SO) who didn't run away in horror and actually doesn't really mind. I can't say she prods me to dress, but really has no problem with it and helps me get ready for nights (or days when the work schedule allows) at home dressed up. Helping with makeup, clothing, nails, etc is something she is more than willing to do and it is really pretty cool to have a supportive SO who thinks it is fun to have a little dress up project sometimes. A bottle wine (or more) definitely helps us get into it more sometimes. But dressing at home wasn't enough for me, as it isn't for most of us. I yearned to try out in public.
So, we did this past year Halloween. Actually, the day before Halloween, but on a Friday night of a Halloween weekend why not, right?
I have gone through the typical try to find the right size game when buying clothing online and it really is a bit wasteful to end up with the wrong cloths and either return them, or in many cases I just haven't bothered to return them and they just ended up in the donate pile.
So, I had it in my mind that I wanted to go shopping. For real. Dressed as a girl.
I live in a very conservative part of the country, where seeing someone crossdressed is very rare. So, I was obviously nervous, but what the hell. Go with it I guess is what I said in the end.
I got home from work early on the Friday and we set to getting me "ready".
A shower with a very close shave. Some facial moisturizing. And it was time to start with the rest of the process.
I didn't hold back. Thigh high black stockings and knee high platform heel boots. Panties, a bra filled with some good breast forms I have, and a dress that went just below my knees. I topped it off with a good wig that I had bought for the occasion (shoulder length to try to cover more of my manly features).
My girlfriend did my makeup, glue on nails which she then painted, and completed the look with some of her jewelry (a necklace and bracelets - I didn't have any rings and don't have pierced ears, so those were missing, maybe some clip on earrings in the future need to be added to the wardrobe).
Oh, and I had to add some perfume. To me for some reason the perfume is one of the major finishing touches in my mind when dressing up. The olfactory stimulation is irresistible to me.
It amazed me how long it really takes to get ready. Nearly 2 hours. Serious respect building for women who do this stuff every day.
To help take the pressure off, my girlfriend also dressed up in a sexy Halloween style outfit and we were set to go out.
The plan was to go to Lane Bryant for some shopping (to buy a couple new outfits) - I am a bigger guy and needed to go to a plus size women's store - then to go out for some dinner, "in costume" for the holiday.
The store was about an hour away so we left the house with me fully dressed up committed to no getting out of the game until we went home.
Driving in high heeled knee high boots was another new experience.
I guess once I was in the car driving I can honestly say that the nervousness went down a little. I don't know if it was because I knew I was committed at that point and just went with it? If it was because we had developed a little "story" for the event whereas we had developed a scenario that I was going out dressed up on a Friday night as a gurl because I had lost a bet with my girlfriend and had committed to spending a weekend dressed as a girl (that I had agreed to do it on Halloween weekend to lessen the potential impact of being in public dressed up, that the other option I had in the bet was way worse and I would easily have chosen this option, and that no permanent body changes could be made - think shaving legs, piercing ears, etc)? Or if I just hoped that because it was Halloween I would blend in and nobody would care. Although with the obvious caveat that nobody really goes shopping for clothes dressed up obviously. Whatever it was, I went with it.
We went into Lane Bryant (and I will add we only went an hour or so before closing to limit the traffic that they would be experiencing) and I just went with it. Walked up and asked a clerk to help. Told her I had lost a bet and was going to go with it to make good. I don't know if she thought it was a true story or not, but she was very helpful. I have no doubt that before I told her I wasn't going to "pass" as a woman anyway. There aren't that many 6', 250 lb women around, and I know my facial features and aneurisms (even with makeup etc) don't completely hide the guy underneath. But I don't really care, it feels good to me.
The clerk was awesome.
She got into it and helped find skirts, tops, and some lingerie. She even helped get some discounts. A little under an hour later I had 3 new skirts, 4 new tops, and a nice nightie.
Bag in hand, back to the car we went and off to get dinner out.
We did a dinner at a Bar/Restaurant, thinking on a Halloween weekend there might be others dressed up, but there weren't. Oh well. Nobody questioned, commented, or even seemed to notice me.
Oh, eating wings with long fingernails is definitely harder also. Along with getting my wallet out of the purse my girlfriend had lent me for the night. All the little things you learn as you do this more.
Dinner done, we went home and enjoyed some personal time to complete the evening out.
So that was my first and only time so far out in public dressed up.
I haven't done it again since, but I will admit I have a yearning to go in public dressed up again. I can't really do it where I live because if I was seen, it would have a potential to have professional implications. My work is rather public, and I work in a very conservative industry, and if I showed up anywhere it would spread quickly. So, maybe my girlfriend and I can find a way to travel and have me be dressed up again sometime and go out. Maybe I will just have to wait for next Halloween to do it again.
I know many here have had many more experiences "out" than I have, but that was mine and I thought I would share it! Not sure if Halloween time really counts as "out", but that was all I have ventured for so far. Thanks for the support from everyone in these forums. Another first, this was my first post here.