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Who are you? Who am I? This is a question that over the years I have found many of us don't ask enough. Instead we find ourselves wanting to dress femme or having a menu of desires and feelings we are having trouble sorting out and so we look for a way to fit in. If we can't fit in with the mainstream, we look for others similar to us and try to be like they are.
The real question is, "Who am I?"
I first dressed in 1987 at the age of 21. I was with a girlfriend and we'd been together for over a year. I'll just say we tended to be very kinky and experimental. Along the way we talked about having me dress up like the woman, have her dress like a man, and engage in some gender swapping role play.
I liked it a lot, but I shied away from it and admitting to myself that I enjoyed it as much as I did. It became another chapter in our young sexual adventures and mostly forgotten. After we split up a couple years later and I went on with my life I found the desire to dress femme staying with me. During a period of time where I was flying solo, as in not being with a girlfriend, I decided to try shaving my legs, after which I tried on short shorts, miniskirts, stockings and heels. I loved the way I looked and felt, but I rejected it out of hand. No one would like me like that and I'd end up permanently single.
Years went by before I tried again. A couple times I dressed for Halloween parties, always combining a look involving miniskirts, stockings, and heels along with a costume. "Cheerleader from Hell" involved a cheerleader outfit with a full-head devil mask and gloves. There was also a witch costume that also gave me an excuse to wear a skirt, stockings, and heels publicly.
Over the years I struggled with my identity. In the later 90s I tried going out and about shopping and doing various errands wearing short shorts and showing off my shaved legs. I found a club that had a drag night and went out dressed. I met both male and female admirers, but the lifestyle scared me, as well as their insistence that I had to "do more to be passable."
I hate the term "passable." It was what seemed to matter more than anything when I first went out dressed and it didn't interest me. I had my first intimate encounter with a man and although I enjoyed it, the experience scared me. I didn't want to "be gay" and ran away again, purged my wardrobe and swore off dressing.
A few years later I ran into an ex-girlfriend from more than a decade before. The issue came up about my dressing because I introduced it. MD was, or I thought she was, a very open minded and accepting person and since our relationship had ended long ago I figured she'd be the best person to come out to. She was very accepting and encouraging and we ended up back together.
It wasn't all wine and roses, and in fact it turned into a horrible experience. "The Dark Times" as I now call it involved her encouraging me to dress more, dress more completely, and to meet people while dressed. She introduced me to men while insisting I was closeted gay and that my acting on my fantasies, as well as hers, would lead me to happiness. Two years later I was broken, depressed, and horrified by the things I'd done. I swore off dressing again for years.
I recently found my way. I now only dress from the waist down. My love of costume dressing led me to enjoy dressing like a pirate from the waist up and a woman in a skirt and heels from the waist down. And I have accepted I am bi, but I can control the circumstances.
We are who we are. We don't need labels, nor do we need other people to define who we are.
Sally your post was both moving and inspiring. Elsewhere in the forum I posted (some time ago) a very brief comment about being one's self. Your post however drills down to the basic fact that we need to be the person we decide we are, or want to be, not who or what others think we should be.
I've heard non-transgender people easily say "Oh, you should just be yourself" yet I feel that behind their supposedly kind word lurks the thought that the 'self' they mean is fine as long as it's more like the person they think that 'self should be. Akin to your comment about the advice you received to be more passable. Those people were 'okay' with your crossdressing but still didn't feel you met their expectations.
I'd happily sit down for a coffee and a chat with a skirted pirate any day - well, unless her legs showed up mine too much. 😉
Thank you for a great post.