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!

The following two tabs change content below.
Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.

Leave a Reply

74 Comment threads
53 Thread replies
Most reacted comment
Hottest comment thread
89 Comment authors
Donna O LaceyChristine VMorgan StaarAmanda LyonsJessica Girl Recent comment authors
Notify of

I dress to satisfy how I feel. I don’t care what anyone elce thinks I know i feel good. They have there own hang up . They are more tense then we are. I don’t try to chase anyone I just want to be myself and share my life stile with my lovely wife that knows me and loves me for who I am. I just wish every one had the chance to do something thay always wanted to do and enjoy it like we do. clothes are clothes mens wemons or what ever. They are made to be wore.… Read more »


I dress like a man b/c that’s what society demands of my physical body type. I cross dress when I can because that is what my personality prefers. But I don’t want to abandon the man. I enjoy who I am … All of who I Am.


hi ladies. my name is bianca I’m from south africa, I’m of indian decent. very new to this but I’m absolutely in love with it… whatsapp me 😉 zero,seven,two,eight,seven,eight,nine,three,five,three;) I’m very very naughty so don’t be shy mwa


I was born and raised in an abusive home and was the outcast in school. Most of my life is painful memories. When I slid on the black dress I could not get enough of turning her loose and erasing me. It has nothing to do with sex, I don’t get turned on seeing myself as her, I simply enjoy the clothing and jewelry she can wear, the night clothes and the nylons. When I am alone I can turn her loose, take walks, and even play my music. I like her much better. I wish I could just toss… Read more »


Actually Darlene is mellow and laid back. She loves Gothic stuff and jewelry. She also likes late night walks.


I, too, lived in an abusive home. My mother beat me over the head with the first thing she could find.My father was impossible to please, nothing I did was ever right, but my brothers could do no wrong. My whole life I had trouble expressing my emotions because I never felt emotions. Countless concussions have affected the way I express myself . I was an angry man that didn’t know how to control it.After coming out to my lo wife several weeks ago changed that. Since dressing almost full time around the house, I have become a kinder, more… Read more »


I honestly become very slutty and outgoing


my life was very much like darlylikeblack01 but the few times I did get found out I was ridiculed shamed and slapped by my own mother . so I have been to guarded to do it for awhile .


I am a completely different person when I dress. I am so much more outgoing, friendly, kind, gracious, spontaneous, adventurous and surprisingly confident. I feel so comfortable and positive being a woman. I have never been so happy. When I am in my male persona I am critical, mean-spirited, painfully shy, anxiety-ridden, miserable, routine-bound, sluggish and negative. When I’m a woman I believe I can do anything, when I’m male I am too busy criticizing, and devising why I can’t do anything to actually do it. I never want to go back to that me.


My persona as debbie is much more confident and outgoing. I am much more chatty and silly but love who I am inside. I also find myself crying during romantic movies which I would never had done as a male. My fem side is so much happier too. I just wish I could find a man who would accept me like this 24/7 to feel totally complete


Oh I agree I am so much happier and out going in fem then I am as a boy. I wish I could be Jenny 24 7.

Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account