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.

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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Amanda Lyons
Amanda Lyons
5 years ago

When I’m dressed as Amanda I care more about my actions and how they affect people I’m way less stressed a lot softer and worry about my weight

Morgan Staar
Morgan Staar
5 years ago

It depends on the situation and mood. When I am with good friends I am outgoing and silly…If I am on a date I’m quiet and shy, but I would go as far to say submissive.

Christine V
Active Member
4 years ago

I found that I don’t get road rage when I’m dressed as Christine.

Donna O Lacey
4 years ago

When the opportunity to dress up in feminine clothes and shoes etc presents itself, the entire ritual is exciting, relieving and very intimate for me. In my male persona I am very self conscious, overly macho, football fishing guy. When I shower and shave myself, then apply my make-up and nail polish I am always happy relaxed relieved and excited. I pick my outfit and heels, pull on my stockings and wig and admire my other self in the mirror. When it’s late and I have the opportunity, i go for long walks with the dog. I love the sound… Read more »

Kathi Miller
3 years ago

When I am dressed, I become much more interested and concerned about other people. I remember to send birthday wishes, give positive feedback, and be an all around nice girl. Also, I work very hard on not slouching. (Posture, Posture, Posture ladies!)
I also become much more aware of how I look.

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