In mid-October 2018, I made a decision that changed my world.
Up to then, for basically as long as I could recall, I’d had a curiosity about being a girl. I don’t know why; I just did. Even as a little kid, I’d stumble around in my mom’s heels. The family thought it was funny, since I was just a kid, but I honestly didn’t understand why they wouldn’t get me any in my size. In my teens, when I did what teenage boys do (you understand), I quickly figured out that I really couldn’t complete the task, as it were, very easily until I put myself in a more female mind space. Without going too far into it, for reasons I haven’t figured out to this day, I get more turned on as a girl than a guy. So, there was definitely something female within me. But black boys don’t think about being girls – or that was the general attitude of my household. So, while I still had my occasional fantasies, I figured that’s all it would ever be – a somewhat odd fantasy that I’d have to keep to myself.
As I got further into adulthood, I still found myself admiring not only women’s bodies, but their look, hair, makeup, clothes, and shoes as well. I loved the way women’s clothes fit them and how they always seemed more interesting than men’s ensembles. I’d try to put together a “sexy” men’s outfit, but to me it didn’t look much different from a lazy Sunday men’s outfit, and it certainly was never very eye-catching, to me. I’d look over at the women and think: “Wow, now that’s a look people will notice.” The colors were more interesting, the materials felt better, and the different cuts and styles just seemed to fit my personality so much better. Eventually, I kind of figured out that, even though I liked women, it is so much more than just a romantic attraction – it’s a love for them and for what they are and what they can do. Yes, a little jealously, too. It took a while to wrap my head around it – well into my 30s – but I came to the conclusion that it’s possible to want to be with women while wanting to be like them, too. I’d spend my time at night before going to sleep watching YouTube videos (and some slightly more … intense media) about transforming one’s self from male to female, and I’d be in awe at how stunning some of the results could be. But it was still just a thing in my head, something to ponder from time to time and nothing else.
Then, toward the end of last year, I had an idea. Not sure why or what changed, but I decided I’d buy a package of panties for myself. It was scary as hell! I actually thought security might say something. But, I did it. And then I got it in my head to buy some bras. I had an idea for making some inexpensive breast forms, so why not? (That turned out not so great, but that’s a story for another time.) Ultimately, over the course of October 2018, I found myself building a feminine wardrobe and buying things like breast forms, hip pads, and wigs. It took a while before I was brave enough to try my hand at makeup – probably three months or so. But I gave it a shot, and eventually got to where I knew how I wanted to look and more or less how to get there.
At first, this was only when I was home alone, which isn’t often, as my disabled mom lives in the same house. It was just me, and no one knew what was going on. After a while, I decided to reach out just a bit, joining a more fringe website where I could speak freely about this adventure and show off my improving looks. That site was much more interested in the private matters of my crossdressing, so to speak, and that got quite uncomfortable, so that endeavor ended after a time. But, being on a webcam (fully clothed) did drive me to find my best look and learn what works and doesn’t work for me, style-wise and cosmetically. So, something positive came from the experience.
Perhaps the biggest step came early this year, when I found the nerve to go out of the house in my female form. Conservatively, I started going to a gay bar, despite not actually being gay. Since then, I’ve become somewhat of a regular, and I’m not sure if they know they’ve kind of been infiltrated, lol. The main thing is that I found a place where I could enjoy my feminine self and there was no judgement and no ridicule. After the first couple of visits, I wasn’t nervous. I was just hanging out in the bar, like millions of people do every day.
It was around that same time that I found CDH and I must say it’s been quite the experience. I don’t always agree with everything I see here, but I know the mission is to create a safe place for folks like us to exchange thoughts and stories. Here, we are just who we are, and we can laugh and cry together as a community. For that, I must thank every member of CDH. It’s been both educational and entertaining. It was, in part, due to the support from this site that I was able to tell my mom what I’ve been doing after she had a life-threatening moment. I didn’t want to lose her with this hanging in the air. She’s been surprisingly okay with it. I think not entirely comfortable, but willing to ride along and let me do what I do.
And now, as I sit here in my white snakeskin leggings and a tight black tank over my around-the-house foam breast forms, I can’t help but marvel at how much my life has changed. Despite everything that’s happened over the last year, it’s really only been about the last three or four weeks that I feel like I’m really comfortable as a crossdresser. I think I know where I stand now – I’m definitely straight, but a little bit gender-fluid, I think. I like the feel of being a woman, but I don’t consider myself a woman. I still have no plans or desire to fully transition, but maybe if life circumstances play out a certain way, I would be open to living a more fluid lifestyle where I get to live my life on both sides of the aisle. Quite a lot would have to change in my life to allow it, but I do think it’s something I would consider. I stopped wearing men’s underwear months ago, and I think I’ve pretty well stopped with the men’s undershirts as well. I’ve worn exclusively women’s jeans even in man mode for a long time now. So, I’ve definitely progressed more to the fem side than where I started. Where does that end up? Who knows?
Just about a week ago, I tried something that I never thought I would even consider. I went to the Las Vegas Strip en femme – in a skirt, no less. It was both scary and thrilling – more scary, though. I spent the entire time worrying about who was paying attention to me and who wasn’t. I was worried I’d have to pepper spray someone at any moment. And that’s not even to speak of the fear of humiliation, to include being outed if I ran into a familiar face. So, I think it will be a while before I try that again. Maybe after I get better, thinner, and understand the small nuances of being a woman a little better. But it was a big step, I think.
So, it’s been almost a year. My, what a year it has been. What does the next year hold? I have no earthly idea. But I can say this: I believe the journey has only just begun.
Girls, I have just a few questions for you now and here they are!
- Have you totally stopped wearing men’s underwear entirely now and how do you feel about that?
- What percentage of your shopping time is now spent in the women’s or junior’s departments as apposed to shopping in the men’s department and how have those percentages changed over the last few years?
- Why do you think there are so fewer African American men who seem to enjoy the thrill of cross dressing than caucasion men?
Thanks for reading my article and I look forward to your responses to the article or any of the three questions noted above!