I thought I’d tell my crossdressing tale in two parts. The second part, where I make my first public appearance as Carolyn hasn’t happened yet; it will happen soon, and how I got to that stage is a story unto itself.
What were you doing last October? If we’d made a bet that I would be in the very place I am now – communicating on a crossdressing site that I joined voluntarily, with purpose and with delight, I would have bet twice my life savings against that very scenario; I’d given long odds to boot. And what was I doing last October? I was riding my bike on a normal Saturday afternoon when suddenly I had the urge to try on women’s clothes.
To elaborate, I’d started receiving testosterone injections, to address both a perceptible decline in my sexual energy as well as to bolster my physical energy. That the injections triggered some new sensations was a potential side effect, but as to why my feminine side should be awakened was something of a mystery – the regimen included an estrogen blocker.
There was another aspect to the timing that was equally important, in a very different sense, it was just before Halloween. The season of witches, goblins . . . and grown men going into women’s clothing stores under the protective guise of a purchasing a costume that never really was.
I didn’t try on my mother’s clothes as a child. I didn’t foster fantasies of myself in drag. There is nothing in my past that can be identified as curiosity on one hand or suppression on the other. There was no denying the force that came over me that afternoon. Scarcely thirty minutes elapsed between my initial impulse and the moment when I stood at the door of a women’s boutique. I was determined not to chicken out, and I didn’t.
The Halloween excuse seemed important at the time. Aside from a handful of clothes on the rack, I didn’t know what I was getting into. I was in unchartered waters; my only guideline the presumption that barging into a women’s changing area would be poor form indeed. I didn’t need to worry; my new friend Claudia, a woman in her mid-to late twenties, had an advanced degree in putting people at ease.
I don’t know about other men stopping by to try on women’s clothes, but it sounded as if she’d dealt with all types. My innocent request for a Halloween fitting didn’t seem to be all that unusual to her. I tried on a dress that might have been perfectly lovely for its intended audience, but on me looked like a sack of potatoes. I then moved to a flexible sort of dress, form-fitting and far more revealing. I silently thought to myself that maybe I could pull this whole thing off.
I didn’t buy anything that day, not from Claudia, and not from Jane, a saleswoman at a store two blocks away. She was equally willing to entertain my fantasy of the moment. The day ended without a purchase, but I knew what I was feeling, and I knew that I wasn’t done.
The day before Halloween I returned to Claudia’s store. I managed to convey that it was too late for a costume — even as I tried on the little dress a second time. I don’t recall a wink in her eye or anything that telling, but I do believe that she knew why I had returned, and it was fine by her. Truth be told, I’d felt a little guilty for wasting her time the first time around. My guilt disappeared when I bought the dress. There was another salesperson working at the time; I deliberately brought her into the discussion of what color was best, eventually settling for teal over purple. Including her was important; I didn’t want it to seem as if I was embarrassed by the whole proceedings and wished to deal exclusively with Claudia. It felt better and natural to be more open as the circumstances allowed.
I also returned to Jane’s store. I expressed a genuine interest in finding something that was just unisex enough for me to pull off in real life. She didn’t come up with anything that worked, but she did show me a dress—it was a regular dress and definitely not unisex. I tried it on anyway. She encouraged me to tell her a little about myself, which was the most direct probe I’d received. Jane was obviously someone who wanted to help rather than someone who was going to be judgmental. I answered that crossdressing was more of a bucket list item with me rather than something I actually did; she accepted my answer, which happened to be the truth.
I revisited Jane right before Christmas—another time when a man could sift through racks of women’s clothing without attracting undue suspicion. I purchased a nice white blouse for my significant other – we’re not married, but we’ve been together 25 years. I told Jane that I was only too happy to purchase something from her, given her willingness to help me out when I had been an unknown man occupying one of her changing rooms. She smiled a knowing smile.
Fast-forward to present day. I arranged for a makeover on a weekend when my common-law wife will be out of town. I’ll go back and revisit Claudia and Jane, but I won’t look the same.
I have no idea how this will turn out. I might love it or I might hate it. Perhaps I’ll simply cross off the “Queen for Day” entry from my bucket list and move on to whatever the next item happens to be. I’m not really worried about what will transpire; I’ll be following the only directive that really matters, the only one I’ve been following throughout this story—I’ll be doing what feels right.
I look forward to sharing my further adventures… maybe even a picture as well…