Eight months…it’s been eight months since the amazing day of getting my first ever makeover at Ulta, then shopping, and finally topping it all off by meeting up with a CDH friend at a brewery to actually talk in person about anything and everything – all night long! It was such a wonderful, normalizing experience, and then…COVID happened. No more work trips, no more counselor safe spaces, no more leaving the house at all for any of my family, which meant no time to express my femme-side fully, without fear or risk of being caught. Holly was boxed up completely in an “out-of-sight, out-of-mind” attempt to help me get through it.
Of course, as we all know, this kind of effort never lasts. The amazing part was that my wife was the one who brought it back up. At the start of the year, we were finally working on trying to do more than pretend my dressing didn’t exist. Then with COVID stress, I tried to relieve her of that added burden because it was, and still is, a very emotionally exhausting effort for both of us at times. When she brought it back up, things came roaring back and I was feeling very trapped once again. On the plus side, I’m able to dress in my home office from time to time, and work a large portion of the day en femme. This can be wonderful, but still I’m basically locked away in a closet. What meant so much to me about my long-ago day out was that I interacted with people throughout the day. I talked at length with the girls at Ulta, who were wonderful. I even talked with a few sales people at stores. Most importantly, I talked with a girlfriend over drinks and dinner, and that was a first for me as Holly. Part of life is interacting with others – in person – and that was something I was deeply craving as Holly. Once I had experienced it, I knew I needed more.
Fast forward from March to October and I FINALLY get a chance to take a work trip! (This pre-dated the Halloween adventure from my previous article). I only had two nights, but I was SO excited to be going out again! As soon as I landed, I put on a running skirt and went for a run on a very popular, beautiful path along the lake shore, with the Fall colors in full bloom. It was amazing! When I got back, I did some work meetings (while painting my nails), and then finally got to start really getting ready. All I wanted to do was look nice for going to a mall, but definitely wanted to feel girly. So I wore a skirt that fell just past the knees, a pink sweater with a big, floppy, scarf-like collar, and my black knee high boots (too small for my big feet, but I love them anyways!) My makeup turned out pretty good…I still struggle with my eyes…but all in all, I felt pretty. So I grabbed my purse, my keys, and then paused at the door handle…always this hesitation and fear…then got over it and went out!
Confession time: I LOVE playing dress up! I’ve been wanting to go to a mall and just try on dresses, especially fancy ones. Unfortunately, in COVID times, no one gets to do that because dressing rooms are all closed…(sniff). Regardless, at least I could browse around, so I drove to the mall, figuring I had a couple hours until they closed, but when I walked up to the doors…WRONG! SEVEN?!?! Who closes at SEVEN? OMG – I can’t believe that I got so close and then completely shut down. Feeling defeated, I went to Target to at least look around, hold some clothes up to me while I could, without people staring at me…you know, just try to feel like a normal girl. I grabbed a couple items from the makeup section and went to check out. While scanning things I hear “excuse me…miss…excuse me!!” I glanced up and, probably in my deepest male surprised voice, responded with something intelligent like, “Oh, sorry? Can I help you?” She proceeds with, “I just had to say, your boots are amazing!” (Huge smile under mask! Heart skips a beat!) I try to recover my voice. “Oh, thank you! That’s so nice!” She then corrals her two little girls and they go on their way. I’m thinking to myself, “a real girl with two little kids to watch over just went out of her way to compliment me.” Honestly, that felt kind of wonderful! So feeling a little better, but still pretty defeated, I just went to dinner at the patio outside my hotel. I sat alone and ended up freezing in my skirt as the temperature dropped. All in all, a bit of a rough night for Holly.
But the next day, I finish work and go for another beautiful run in another running skirt (can you tell I like running skirts?) This time I got ready early. I wore a simple dress that night to shop with more comfortable boots (still heels, of course) and got to the mall around 5:30 (Seriously…7 PM? Still can’t get over that…). I decided to look in JCPenny because I figured they would have more interesting clothes when compared to the other stores at this mall. I found the clearance section and was looking through it when I noticed there were no barricades at the changing rooms – well this is interesting. I find an associate and she says, “Yes, they’re definitely open! Enjoy!” OMG OMG OMG!!! I head back over and grab something like five dresses, a skirt and three tops. I head on back with the biggest smile, not believing my luck. This is what I’ve longed to do so badly. I went through them all and then decided I wanted another round, but this time it was eight dresses. I was back there until they closed the store. In the end, I was so excited just to be able to buy one dress for only $18, on clearance! And it’s so cute and so me – I just adore it. (I’m wearing it in the picture)
Ok, so…winning! What next?
I went back to my hotel and changed because I wanted to go out to dinner, but again, the place I was targeting was outdoors, so I layered up a lot. Still girly though, with my leggings and sweater dress over the top. I got there and even though it was reservations only, I got a single spot and it was so worth it. It was another brewery (yes, this girl also loves her beer!) and the beer was amazing. To top it off, so was the food! The best part of the evening was when the waiter came over and just sat down with me to talk for awhile. We talked about the beer and how they made it differently and I thanked him for the food recommendation, because it was delicious. Again, I got to actually interact with someone and it felt amazing!
Even better, I was able to tell my wife about all of my experiences once I got home. Finally being able to share this with her, even if it’s only talking about it at this stage, makes it all more real, normal, and wonderful!
Great article, Holly. Miss it so myself; at least I can get this great kind of vicarious experience on CDH.
Hi Holly, Terrific article. You did everything I’ve ever wanted to do, but haven’t yet. Do you think the waiter at the brewery was hitting on you? Do you think they knew you were a CD? Either way, very exciting. I’m a runner too. Can you please tell me what brand of running skirts do you buy and like? I’d like to get a running skirt, not a skort. I look forward to your reply. ❤️
Really fun reading your story. And you’re a girl after my own heart….The JCPenney clearance rack? My favorite. Leave a few things for the rest of us ; )
A lovely experience for you Holly. I remember a few of my own first exploits. And the dress is just adoring!
Thanks for sharing – I enjoyed reading your experience. At the moment, my experience with shopping is of the window shopping variety. Maybe some day I’ll pick up the courage to try some on.
What an exciting adventure Holly. An experience you will never forget and I know what a thrill it is having done it for so long
Love the dress. Love your story. Getting out and being yourself is always is a wonderful experience. Good for you girl!
What a wonderful experience. That does mirror mine to an extent. As I was getting used to going out en femme, and had found a CD/TG social group to meet with for dinners, which is so nice. Then we had the Covid lockdown! However one of the few places I could go was the grocery store, which I did, casual in jeans, sweater, modest heeled boots, and such. It is amazing to be treated like that, like a real woman! Lets hope we can get through all of this in a more months and we can get back to being… Read more »
helo
Hi Holly , reading your article made me happy for you , and you look so pretty . I’ve been out a couple times to shop , usually in jeans and a top and pantie and bra under and it felt so thrilling so right . I will be so glad when the virus goes away so all can get out and have fun . I’m glad your able to talk to your wife to , takes a lot of strain away to . You rock girl . Leslie