What Is Your Crossdressing Personality?

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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84 Comments
  1. Profile photo of nichol
    nichol 7 months ago

    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 .

  2. Profile photo of Allie
    Allie 7 months ago

    I honestly become very slutty and outgoing

  3. Profile photo of JoJo
    JoJo 7 months ago

    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 understanding, gentler man(or woman). I can finally enjoy what emotions are supposed to feel like. It’s been such a revelation that I break down and cry when I feel emotions. For a rough and gruff 61 year old former factory worker that had anger issues , this has been a very confusing time. I believe that by letting JoJo out, I’ve found my feminine side and I’m loving every minute of it. I find that I need hugs and kisses often throughout the day. I wish I would have had the nerve to come out to my wife years ago. I feel like I’ve missed so much of life’s enjoyment, not to mention ruining much of my wife’s enjoyment. I apologize for the long post. Too many emotions to write about that are clouding my head and heart. Thank you for allowing me to rant, Love you girls, JoJo ( finally feeling the dream) ….

  4. Darlene 2 years ago

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

  5. Darlylikeblack01 2 years ago

    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 him and let her live the rest of my time.

  6. pri 3 years ago

    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

  7. Judith 4 years ago

    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.

  8. Tammy 4 years ago

    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. So I’m waring my clothes my way and it makes me happy. When I bye my clothes nothing is said about what I bye. When my wife bye mens clothes nothing is said to her eather so who cares what we ware as long as we are decent .

  9. avalana 4 years ago

    hi i’ve been dressing as a girl since i was 3yrs old i also had boy clothes,which i was told to wear at times,however,the older i got ,the more i prefered the girl clothes..they were (are) way more comfortable ,at least to me! i’ve worn nothing but panties for 30+ yrs,all my jeans are misses sz 5/6,and it be a rare day when i’m not wearing a bra w/forms…90+days now,and nobody has noticed…sweet…i can only hope that white america will become more relaxed in their ideas and their notions as to “whats correct”or “whats right”to wear. i myself am starting to get weary of the stigma of wearing nought but girl clothes,they fit me better,and feel WAY better than “boy clothes” although that does bring to mind an article in tapestry called “over bra and panties,what” when you consider what gg’s wear, over their bras and panties,it would seem that all is fair game,if you are wearing a bra and panties(and they need not match,mine don’t at the moment) it doesn’t seem to matter what you’re wearing,as along as it fits and feels good..please enjoy your whimsey’s and keep your faith…peace,avalana

  10. ginger morgan 5 years ago

    looking for help on my first date as a crossdresser with a man ginger

    • Antome 4 years ago

      Then there is a bladerunning balance between the respect you owe to the man you date and your need to pass as woman. Does him know? And what are your intention with him, are you only interested in girls, boys or both?

  11. Diana 5 years ago

    Would love for someone to get togeather and dress up with in San antonio Tx

    • Delores 4 years ago

      Hi Diana,
      I am a crossdresser from San Antonio. Maybe if we start some form of communication we could eventually meet and crossdresser together .

      Love to hear from you.

      Hugs n kisses,
      Delores

    • Nancy 3 years ago

      Diana,

      Would like to meet sometime. Would like to dress up and go out also. Live on NW side.

  12. stevie 5 years ago

    looking for a g g in okc area that would like to meet an artest type crossdresser !

  13. Alttlbiazz 5 years ago

    I started early with putting on my sisters clothes and underwear. Although I am bisexual I enjoy releasing the girl in me when with a man. I have yet to wear make up or wig but I can see that happening one day.

    • Vanessa Law 5 years ago

      Go at your own pace dear, and do what’s comfortable and right for you 🙂

  14. Daywalker1966 5 years ago

    For me myu alternatie personality has long black hair, nice legs and a very pleasant personality.  She is pretty and liked, and she is things I cannot be a s  a guy.  I can dress her and make her be what I want her to be.  She is an escape from me, from the norm, and from a life of problems.  I dont have to worry about her having issues with things I like or do.  I like her better than me, she is a breath of fresh air.  She is just plain fun to be,.

  15. Tailsing 5 years ago

    I think it’s why men crossdress . And call it a crime. It’s why women can dress up in any clothes she wants and get away with it. What I mean is go to any major city or college. Look around for several hours checkout . What men and women wear, I’m guesting this part that half the women wear male style clothes. But if a male dresses in a nice skirt, top and nylons and heels or flats and he looks okay in the outfit. How many will say what is wrong with him or something like it?

  16. seha 5 years ago

    same with me also

    • Vanessa Law 5 years ago

      Thanks hon – welcome to Crossdresser Heaven! *hugs*

  17. Jabooska212 5 years ago

    I cross dress in stockings and heels and have a fantastic wank, thats all there is to it, I love standing there in stockings, high heels, basque….I do this in the garden, has to be out doors, exposed although not ultimatley risky, the sensation is intense…
    Im straight as straight can be, my girlfriend doesnt know about it, although funnily enough a few months ago she said she would like to see me in stockings…..its kinda personal though. I have another friend (female) who has actually stated that she wants to fuk me while I wear the stuff so that Im going to do, both of us dressed up in lingerie and heels, jeeez cant wait.

  18. Jabooska212 5 years ago

    I cross dress in stockings and heels and have a fantastic wank, thats all there is to it, I love standing there in stockings, high heels, basque….I do this in the garden, has to be out doors, exposed although not ultimatley risky, the sensation is intense…
    Im straight as straight can be, my girlfriend doesnt know about it, although funnily enough a few months ago she said she would like to see me in stockings…..its kinda personal though. I have another friend (female) who has actually stated that she wants to fuk me while I wear the stuff so that Im going to do, both of us dressed up in lingerie and heels, jeeez cant wait.

  19. Jabooska212 5 years ago

    I cross dress in stockings and heels and have a fantastic wank, thats all there is to it, I love standing there in stockings, high heels, basque….I do this in the garden, has to be out doors, exposed although not ultimatley risky, the sensation is intense…
    Im straight as straight can be, my girlfriend doesnt know about it, although funnily enough a few months ago she said she would like to see me in stockings…..its kinda personal though. I have another friend (female) who has actually stated that she wants to fuk me while I wear the stuff so that Im going to do, both of us dressed up in lingerie and heels, jeeez cant wait.

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