What is your crossdressing personality?

Last night my wife and I were watching the episode of Boston Legal where Clarence – the otherwise shy unassuming lawyer who enjoys crossdressing in his spare time – enters a singing competition as his alter ego Clarice. We watched the dramatic transformation – his feminine persona shone radiantly with confidence when she set foot on stage. Singing, dancing and shaking her booty with freewheeling abandon. As if crossdressing psychology had dazzled her mind and switched her personality.

After the show my wife asked me a question which got me thinking about my crossdressing personality. Am I more confident and outgoing when dressed as Vanessa? Does my personality change in ways not easily explained by being more feminine?

What Is My Crossdressing Personality?

When I put on my makeup, heels and hose I become more feminine, more outgoing, more confident, more excitable, less contemplative, less uncertain and more open to being vulnerable. When I’m in male mode I’m constantly worried about what people will think of me. I try to be perfect, to not offend anyone, I shape who I am to fit into the person I believe others want me to be.  When the transvestite inside of me comes out I realize that I’ve probably already offended some people. I don’t mold myself to their expectations, but find myself free to be who I am inside.

Crossdresser Heaven - Find Your Tribe

It’s a strange balance. I find myself less interested in what others think about me and more interested in them. Even a light dusting of makeup and a feminine mindset will find me chatting with cashiers in the checkout line, willing to share a piece of my day and eager to hear a bit more about theirs.

In truth I like who I am when I’m crossdressed. I think that if there was socially acceptable cross dressing more people would feel comfortable expressing a different side of themselves. We may even find that crossdressing psychology is sometimes the best kind of psychology.

What Is Your Crossdressing Personality?

Does your experience mirror mine? Think about what it’s like when you’re the woman of your dreams. Who do you become when you’re dressed?


P.S. When you’re crossdressed be fabulous on the inside and the outside! Learn how to dress and act like a woman!

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  1. Kristy Bucklyn 1 day ago

    What an interesting question. Since I’m “new” to the whole “going out while dressed” thing, it’s hard for me to gauge but so far I think I’m more empathetic than what my guy self would normally be. I think someone in the thread already came up with the best label so I’m going to borrow it – “perky idealistic Southern girl.” Two instances – first, I was out dressed one evening in our city at a local music festival and on the way to the boulevard from the parking lot I spotted this family – dad, 4 or 5 kids and a bedraggled mom trying to keep them all in line. Anyway, I was sort of “cornered” at that point and we traded glances. I smiled at her and she smiled back and it was the best feeling (dad didn’t even notice me or seem to care. The second was more recently in another city again in the evening. I was walking downtown in my usual fare when I came across a homeless man in a doorway. Mind you, this was a really nice, well-lit part of town where I felt reasonably safe and this poor man so down on his luck asked for help. In my city we have a lot of panhandlers at stop lights and (for better or worse) people don’t pay them much mind. But that night Kristy was going to at least try to help someone. I reached into my purse and pulled out a couple bucks. “Here you go my friend, I hope things get better,” I said. “Thank you darlin'” he answered, and I went on my way strolling down the street. Each time I was in my usual outfit – dark top, a pretty skirt, tights and heels – feeling confident, idealistic and empathetic in a way I might not have been had I not been en femme at that moment. Maybe I felt we were all “in the same boat” – vulnerable to life’s situations. But what an amazing phenomenon how our outward appearance can influence our inward decisions and our actions.

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