I’ve been mostly lurking here for the past few years, but recently I’ve been making good progress with my CDing activity, so I figured I’d drop by and share an update.
Warning: Long, self-indulgent post to follow. Executive summary: Timid CD who was afraid to leave his living room finally manages to start stepping out into the world, and finds it really isn’t such a difficult thing after all.
I’ve been trying for the past several years to do a better job of embracing and enjoying my femme side, and though I had made a decent amount of progress, I was still held back from my ultimate goal of getting out in public by a pretty common problem: I don’t pass. At all. Like, not even close. Now, I’ve gotten pretty good with a makeup brush, and a while back I invested in a fairly high-quality wig, so I can certainly make myself look less amateurish than I did ten years ago, but I have enough self-awareness to know I’m not going to actually fool anyone. Being 6’4” certainly doesn’t help, but I don’t have a particularly androgynous face or body shape, so I doubt I’d have much more success even if I were a foot shorter.
And for years this was the huge sticking point. I really wanted to get out and about, but I was sure folks would point and laugh when they saw what was obviously a guy in a dress, and I didn’t have any interest in that. So most of the time, I’d get all dressed up and stay in my living room, or maybe go out for a late-night drive just for the sake of getting out of the house. If I were feeling particularly brave, I might take a stroll through Walmart at 2 in the morning, but I didn’t really think of that as being out in public since there weren’t many people around, and I generally tried to avoid the ones who were there. It was a way of getting my feet wet a bit, but after a while, sneaking around at night started to feel kind of silly.
Then, a few months ago, I was randomly flipping through my copy of “My Husband Betty” (which I’d previously read years ago), and happened upon this quote:
"Crossdressers who wish to pass *physically* are aiming too low. They would be much better served developing the confidence, character, grace, and manners that will allow them to pass *socially*. The former is living in the shadows; the latter is blossoming in the light.”
Or, in other words, Quit trying to blend into a crowd of women (which, at least in my case, is nigh impossible), and instead learn to be proud of being a crossdresser. Now, over the years I’ve seen plenty of variants on the idea of “It’s all about confidence!”, but never really believed it. But for whatever reason, this quote actually resonated with me. So I don’t pass…well, so what? What exactly did I think would happen if I went out and people saw that I was clearly a man in a dress? I’d probably attract some extra attention, which, as a naturally shy person, I wasn’t crazy about, but I figured I’d get over it. Some random strangers might think I’m weird? Well, I’m 41 years old, which is way too old to care about the opinions of random strangers.
And just like that, going out en femme suddenly seemed like something I could actually do. So I started to look for an opportunity to get out and mingle with the normals a bit. This past April, there was an ideal chance: I had a rare weekend when I didn’t have to work and my wife was out of town (not to give the wrong impression: she’s amazing and completely supportive of my crossdressing, but has balked when I’ve suggested she come out with me while I’m dressed up, and if she were around we’d almost certainly find something fun to do together rather than me engaging in a solo activity).
On that Friday night, I got home from work around 7:00, did a quick change, and headed out. There’s a Kohl’s nearby that stays open until 11:00 on Fridays, and that seemed like a good, low-key place to start. I got to the store around 10:00, sat in my car for about 10 minutes to psyche myself up, took a deep breath, and walked in. I browsed around for about half an hour, during which time...shockingly, nothing extraordinary happened. As I expected, there were a few other customers around, and they mostly ignored me. One of the young men working there did a double-take when he saw me, but didn’t say anything. I tried on a few outfits but didn’t really love any of them, so I headed out empty-handed. One of the female cashiers gave me a big smile and said “Have a great night!” as I was on my way out of the store, and I tried my best to respond in kind. I got back to my car without having a panic attack. Victory!
The next day, I figured I’d ride my momentum and up the ante a bit: I decided to hit the local mall during actual daylight hours. After waking up early to undergo my transformation, I pulled into the Macy’s parking lot around 10:30 in the morning, and without giving myself any time for second thoughts, got out of the car and walked through the main entrance. This trip was a little less successful; after about ten minutes of browsing, I started feeling a little paranoid that everyone was staring at me, and retreated back to my car to gather myself. I decided on a different plan, and headed to a smaller mall a few towns over, so that there would be a little less pressure. This went much better: I parked outside the Bon Ton and walked straight in with as much confidence as I could muster. After giving myself a few minutes to equilibrate, I found, much to my surprise, that I was completely relaxed. There were several other customers browsing around, and they reacted to me in more or less the same way as if I’d been dressed as a guy: they paid me very little attention and minded their own business. I tried on several dresses and found a few that I needed to add to my wardrobe. I was a bit nervous about interacting with the cashier, but she was actually super friendly and cheerful. As I headed out the door, my main thought was “That’s it? That’s what I’ve been too scared to do all these years? That was easy!”
Since then, I’ve managed to have several more outings en femme—just shopping trips, nothing too adventurous so far—and everything’s been great. On a recent trip to a nearby Macy’s, I did start having some serious butterflies, but when I wandered by the cosmetics department, I noticed that my favorite artist was working at the MAC counter, so I decided to stop by to say hi. She’d helped me out plenty of times when I was shopping in guy mode but had obviously never seen me en femme before. Her response was something along the lines of “OH MY GOD YOU LOOK AWESOME YOUR MAKEUP IS FANTASTIC I LOVE YOUR DRESS,” which of course calmed me right down and put me in a makeup-buying mood.I got a similar response from another one of my favorite folks at a different MAC counter a couple weeks later…and when I mentioned to another artist (whom I hadn’t previously met) that I felt my contouring and highlighting game was pretty weak, she handed me a mirror, grabbed a brush, and gave me some quick tips, then told me I absolutely HAD to come back at some point for a full makeover so she could give me the whole tutorial. (Have I raved about MAC recently? MAC is awesome. Everyone should buy lots of stuff from them. Seriously.)
And the negative responses I’ve been SO afraid of all these years? Pretty much nonexistent. The closest thing would be this past weekend when I was at Lord & Taylor hunting for more pretty things to buy. I looked up at one point and saw a sixtyish guy standing next to the women’s fitting room (waiting for his wife, I assume) just STARING at me. Not even attempting to be subtle about it. I thought, “Eh, screw him, let him stare, I have bargains to hunt for,” and went back to my browsing. Five minutes later, I looked up again, and he was in the same spot, still staring. If I had a little more sass in me, I would’ve marched right up to him, struck a pose, and told him to go ahead and take a picture already. Maybe next time.
But positive responses? Plenty! Every single cashier I’ve interacted with has been incredibly friendly, and the young lady who rang me up at Sephora the other day told me she loved the lipstick I was wearing. A saleswoman at Macy’s greeted me with a huge smile and said “It’s lovely to see you here today!” Several random folks have walked up to me to tell me that they thought my dress was really pretty, and, in one case, that I looked “fabulous.” I have to admit, I do love a good compliment, and if the tradeoff is that I have to deal with some creepy dude staring at me every now and then, well, I’ll take that deal.
Probably my favorite response was when I was walking through the mall and noticed a small group of younger folks (late teens, I’d estimate) coming towards me in the opposite direction. Just as they were about to pass me, one of the girls in the group looked over at me with a surprised expression on her face and said, loudly, “Oh my God!” I didn’t respond and kept walking, but a couple seconds later, apparently realizing her faux pas, she followed up with an equally loud “You go, girl!” Definitely put a smile on my face.
So that’s my story. It took me years to work up the guts to walk through that first door, but once I broke that barrier, everything else has been far easier than I expected. If anyone had told me a year ago that I would be at the point where being out in public (at least in the relatively safe space of a shopping mall) fully en femme was starting to feel completely normal, I’d have told them they were crazy.
And if there’s anyone reading this who wants to get out in public but is afraid as I was for so long: Seriously, just get out there. It’s tons of fun! All the things people around here say like “It’s all about confidence!” and “All of the barriers are only in your own mind!” are actually true. Worried about not passing? Again, I don’t pass at all, and it really doesn’t matter. Feel like you’re too shy? I absolutely GUARANTEE you that I’m shyer than you are. Give it a shot, it’s easier than you think.
If you made it this far, thanks for reading! Now off to plan my next adventure…
