First Time Going Out

[Raychel]

I have been out a few times.
Much easier when I lived in Tennessee. My house was in a very private place.
I could park the truck close to the door and could get out easier.
I would go for a drive occasionally, never getting out of the vehicle.

Now living in Maine, my house is in an Mobile Home Park, Houses very close together
Definitely more of a challenge to get out.
Although I have been out a couple of times, Leaving and changing after I left home.

Having been laughed at and ridiculed so much as a child. I really have no desire to even get close to that again.
Therefor I am very careful to avoid those situations.

Plenty of deep rooted issues here.
I will never be able to just go out how prefer to dress.
But my hats off to all that can.
I bow to my idols.

[Just Dana]

During COVID (the worst part of it), I got up the nerve to go for a drive while on an overnight in another city, then a month or so later, my wife and I went for a wander in downtown Chicago on a weeknight in winter. I didn't have to interact with anyone on either outing. So, what I consider my proper first time out was...

Last month, I was supposed to have my very first date as Dana. I bought a new dress, a black, long-sleeved, midi length sweater dress, since I didn't really have anything for going out on a frigid February evening. My wife loaned me a beautiful, red scarf that really set it off and matched my red glasses. I scheduled my first professional makeover at Transformations by Rori. Then, he cancelled. Thanks COVID! But, everything was set and Rori had even scheduled my makeover at her posted closing time, so I decided I'd put on my big girl boy shorts and go anyway. As it turns out, I wasn't alone; Mr. Murphy accompanied me all evening.

When I got to Rori's, there were three 60ish women trying on wigs. They had no idea it wasn't your everyday wig shop. Rori showed me to the dressing room and I got changed - from the neck down. I'm not sure what the women thought when I came out and started browsing while they were finishing up with their shopping, but I'm sure I gave them a good story for later. Then, Rori did my makeup, helped me get my wig just right, and I was off.

Not two blocks from the shop, a younger guy pulled up next to me at a stoplight, a bit ahead of me, since he'd slammed on his brakes when he saw me. He craned around, looked right at me, and nodded. I nodded back, since that's the polite thing to do. He then proceeded to pace me for the next block or two. I looked straight ahead, but out of the corner of my eye I could see that he kept looking at me and gesturing, trying to get my attention. It was definitely a bit scary. I made a quick turn off the main road and lost him. I have no idea. Did he immediately clock me and think, of course a transwoman out for the evening would want to go home with him? Did he think I was a woman, who'd be impressed by his road seduction and want to go home with him? Was it something negative? Beats me. But, I didn't let it bother me and continued on with my evening.

I went to a LGBTQ bar (regular Chicago neighborhood kind of bar, not a dance club) for dinner. I got there and dug my vax card and ID out of my purse, completely forgetting to put on my mask. (Doh!) I walked in and the bartender said something like, "Hey glamorous." Short pause. "Do you have a mask to go with that? You need to wear a mask in here, honey." I was so flustered about the mask that I didn't mind that everyone turned to look at me. I fumbled around in my purse again, found my mask, and all was right with the world. The waitstaff was great. The rest of the customers seemed to completely ignore me. Nirvana.

After dinner, I'd hoped to stop at a Target and do some shopping. Unfortunately, it was already closed. So, I walked around the block and found a little shop where I could buy a six pack before heading home. The store was run by two elderly men and you're supposed to scan your ID when you enter. (This was near Wrigley Field, so there are always lots of under 21s trying to buy alcohol.) I had to hand over my ID, so one could go back to the front door and scan it. I'm well past getting carded, so I was not expecting that at all! They were perfect gentlemen, though.

Before I got home, I found a spot to pull over and put on a pair of jeans, hat, boy coat, and a mask, so I wouldn't have to walk down my block all dolled up.

It was the weirdest evening. It seemed that everything that could go wrong, or at least not quite right, did. But, I had an absolutely incredible time!!! Once I put on that dress, I was in the zone or something. It's kind of like when I have to get a shot or a blood draw. I'm always very nervous beforehand, but perfectly fine once I sit down in the chair.

So, that's my story. I hope to do it again, but without the hiccups!

Dana

[TamT]

My first time going out was about twenty years ago. It was near midnight and I was with makeup, a party wig, water filled baloons and a not very blending outfit: mustard synthetic leader pants, a red&mustard blouse, a dark red synthetic leader jacket and red sandals. I always wanted to go out, and I was so excited that I put some Ids and cards in a purse, covered my outfit with a windbreak, a jeans and a sports cap, changed my shoes and walked to my car in the parking lot of the building. There, I removed the jeans and put the sandals again. After I left, I stopped some streets later to remove the windbreak and the cap. I drove for about half an hour without a destination, but at some point, I parked and took a deep breath before opening the car's door. Once out, I walked for about 5 to 10 minutes in the neightborhood, returning to my car from the opposite side. I drove back to my home, covering my outfit again with the windbreak and the cap.

I repeated that few times in the following months with different outfits, but those were other times. Today, I'd not recommend going out late at night, as it has gotten dangerous, at least in my city.

Being in a DADT relationship, as I cannot dress at home and I cannot pay for an hotel room, I found it much more easy and fun to underdress in the morning, then dress and apply makeup in the car during lunchtime and drive to a mall. I don't care if I blend (I know I don't pass), but I own it. I can check for sales and buy more clothes and accessories as Tam without any bad experience at all. I return to the office after an hour, remove the makeup and clothes still in the car, then back to work for the rest of the day.

[Jenni6521]

I have been out in various stages of being dressed many different times. Recently, it has been jeans, blouse, shoes, no makeup, forms or wig, don't own them. Last Friday I went for my first complete makeover. That was the first time in my crossdressing career that I put it all together. I planned for my trip to Washington DC for the makeover by stopping to get my nails done first. I had them painted in a soft pink. That was the negative experience. I walked in and was asked to take a seat near the back of the salon. There were no other seats available. After sitting down there was a women getting a pedicure, she gave me terrible leers for most of the time I sat there, along with lady who was giving her the pedicure. To build my courage I just continued to say you deserve to be here and you are okay. I also avoided eye contact. I was sat between two young ladies during my manicure and both of them smiled kindly at me. I know that I opened myself up there because of not wearing a wig or makeup. My makeover was amazing, and I was stunned to tears when I first saw myself in the mirror. I left there with my makeup still in place, the same blouse and bra, jeans and shoes that I wore. I went to check into my hotel room and that was the one of the best parts. There were to female clerks at the desk, one young and one closer to my age. The younger one checked me in and asked for my CC and ID. I got them out of my purse. She stared at my ID for longer than I expected her to. Then she asked "is he here." Only my sisters here can understand the smile that came to my face. I removed my mask and said he is right in front of you. She had this wonderful smile, and then said you look beautiful, which lead to another tearful moment. The other clerk walked over and was also very supportive and mentioned that she wants to get a full makeover. She commented on how pretty I looked. I went up to the room. I had planned on maybe going out, but was pretty pooped. I went to the target to get some makeup wipes and a couple of other things. I grabbed some takeout and went back to the room. The next morning as I returned the key, they were also working. Which started a new conversation with both of them.

[Wendy-Lyn]

I've been dressing on-and-off for decades, but mostly only partially and for limited times. And always at home. I NEVER dreamed I'd ever have the guts to go out in public dressed, although I'd often wondered what it would be like. My first time out in public was not long before last Christmas. I went out underdressed and changed in the car into a skirt and shoes, put on my wig and some jewellery, and went to a park and ate lunch while I watched some kids playing cricket. Then I went to a place I know and got out of the car and went for a walk. I was terrified, but exhilarated at the same time.
It seemed to unlock something, because I've been out fully en-femme a few times since, and I often go out in 'stealth' mode even when presenting as Jimmy. I've even been shopping en-femme a couple of times, but nothing too exciting - just makeup and odds-and-ends.
Onwards and upwards.