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.

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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. Julie 13 hours ago

    That is such a good question, How do we feel when Dressed, Actually I am fairly confident either way, As Julie, damn do I look hot. So many guys and girls tell me I am the hottest girl in the club. I am very confident as Julie because I know I have it going on. When I first started I kind of dreamed that I could walk down the beach all dolled up and would get catcalls. Well I have no achieved that on the beach but going out to clubs, WOW do the guys compliment me. With the ladies they are usually jealous of my legs, say they wish they had legs like mine, even hot sexy girls have said that, and I dance with most of them, they love it. So with all these compliments, I am beaming with Confidence as Julie. I am also extremely excited and feel super sexy. with all the confidence I still feel a little shy, like to play hard to get and a little bit mysterious. Two guys are crazy in love with me, one I like the other not. The one I like just cannot change his life so I understand but I can see his heart aches. Pretty Woman have control in this world, I love a beautiful woman. I love to go in a store like CVS or Walgreens and buy makeup, it makes me feel so lady like, I love it, same going to Macy’s to shop as Julie.

    As a guy I have confidence also but I have so much more fun as Julie. As a guy I dance with a lot of Girls and they love to dance with me but as Julie I get in on the girls world, which is cool. I am Privy to all that little private girly talk. I now know some ladies rooms are downright nasty!!! Thought guys were bad, think again.

    Cross dressing may be the most amazing thing I have ever done, to come home on a Friday night, get all smooth and choose you skirt and heels, put on your makeup, go out and meet the girls and boys and dance all night, it makes me feel so satisfied that I have pulled it off. My Advice show guts walk right into the club and meet people, vanilla people, it is amazing and 75% accept and love you and the other 25% can take a hike, just act like a woman, mannerism;s don’t stuff your facelike a pig, be a lady and not a slut……Oh By the way the long brown hair and DD boobs are very coveted by the guys…….The hot sexy legs and pretty clothes and heels are loved by Woman . Love Cross dressing, Kisses to all Julie

  2. Leonara 3 months ago

    What a thought provoking topic.. In male mode , I am always looking for “how am I doing”? As Leonara , she is shy and the woman within seems so natural but still lonely. Although this may seem vain, My pending makeover will show how the woman within is as pretty in public… The ladies here are so supportive and I thank you….Leonara

  3. Lisbeth Lacy 3 months ago

    When I am Lisbeth I feel like perky idealistic southern girl. Lisbeth is a feminist liberal. She dislikes men for the most part. But Lisbeth likes to look attractive but not slutty. She feels that a woman can be attractive and modest She enjoys wearing tight fitting skirts and dresses that either knee length or below the knees. She prefers pencil skirts because she loves to show off her slender feminine figure

  4. Louisa Jones 3 months ago

    When I’m Louisa I am much more relaxed and content. I also feel slutty,When I am dressed in male clothes I conform to what’s expected of me.

  5. Davia Deaton 3 months ago

    I live in a small southern town and crossdressers are not tolerated what do I do

    • Davia Deaton 3 months ago

      You said you only wanted to do this when your high!!!…so what’s really going on caus I wanted the husband I married and I’m in love with

  6. Interesting article Vanessa! Thank you for bringing it up. I have been studying psychology for a while….in particular….female psychology. I want to know what makes females the way they are and what avenues led them down the path. Men and women are physically quite similar. Change a couple of body parts, add some hormones and voila you have an opposite, at least in the physical end of things. Mentally…..not so easy! I hope to gain enough insight to be able to become a successful cross dresser. I want to walk the walk and talk the talk as it were. I have met a couple of dual personalities while on the psyche ward (for unrelated issues…..PTSD) and it was a very worthwhile meeting and I was lucky to meet both sides of the coin. They presented a skill in the nuances that we struggle to perfect. This is what I want to find out. Physically, I can convert to female no problem…..there is a need to perfect make-up (still working on it) and more importantly, how I re-act/respond to issues that “push my buttons”. That undoes all my efforts at feminization…the male persona comes out to respond. This needs a lot of work! As I come across things that might be helpful to all us girls…I will post same. Also, if fellow or fellowesses have any helpful hints….they would be most appreciated. It might be a bit for me to reply as I seem to have a proclivity towards dumping my coke onto my key board! That is why I use a desk-top with separate keyboard…..afraid to really damage my lap-top! Lady Veronica Graunwolf.

  7. Pippi Long 3 months ago

    yes , i am totally the opposite of my male side .When i get dressed up i become Pippi ! She is more free spirited and a little more on the daring side ! And yes i do know the feeling of trying to be perfect , trying to keep it all a secret but not really caring if found out lol seems silly if you think about it .

  8. Rozz 4 months ago

    As Rozz, and as yet I have not been able to come out, I still find myself to be a tame, reserved person as opposed to my normal persona. At the present I want to come out but I do not have the support and am afraid that I will lose the people I love and care for If I do. therefore I keep Rozz locked away until I am sure I have a lot of alone time. then I enjoy being fully fem and free.

    • I really hurt for you Rozz. The only other Rozz I know is played on the Frasier Show(Peri Gilphin). I just love her personality. Yes, it seems “only people can make you cry”. Hopefully time will help those near and dear to be more accepting. My people do not know and never will….thankfully most of them are far away or gone now. My ex didn’t like it….and that is one of the reasons she is my ex. If you wish to talk or borrow a sympathetic ear…..contact me. Lady Veronica Graunwolf.

  9. Janine Milburn 4 months ago

    When i am Janine, I feel so hot and sexy. I always get shocked when i see my big curvy ass. I become a hot bitch

  10. Lisbeth Lacy 4 months ago

    when I dress up as Denise I feel so good about myself especially if my make up looks good and dress fits like it should. I see myself as a femme fatele. I prefer to dress 1950’s style when women wore tight dresses, stockings & garter belts…etc.

  11. janine 4 months ago

    I am janine, when i am dressed i become the sexiest slut i have ever seen. My big booty is my best asset and it jiggles when i walk. I always feel hot and i love it

  12. Sarah Daniels 7 months ago

    Sarah is chatty. Well she would be. I find in my normal male life I am more chatty than I ever was. Im always asking people how they are doing and talking to cashiers etc. Sometimes I find I am talking for quite a while. Sot into a dress shop to pick up some stuff Id ordered and got chatting. before I know it the 3 shop staff were there talking to me about the stuff Id got for my wife. Not sure if they sussed me out then but one of them certainly looks at me differently. lol

  13. Donna March 8 months ago

    Donna is a party girl, I wear classy outfits and heels. I stand out being tall to start with but i love this life. The only time i wear non feminine clothes is on the job. I always look forward to off time and will always do so. I don’t drink but do know how to have fun.

  14. Michelle 10 months ago

    I’m submissive when I crossdress. I keep my legs smooth shaven, and would love for my wife to encourage, even order me to wear sheer nylons on a regular basis. I would also enjoy my wife teasing me about my crossdressing , maybe calling me her feminine “bitch husband”. I’ve always had the fantasy of my wife with that dominant nature, among other fantasies she’d never be open minded enough to accept in our marriage. Maybe too little; too late!

  15. Steffani 10 months ago

    Steffani is the same way. She’s a diva and I’m shy and reserved in male mode.

  16. Samantha Louise Scott 11 months ago

    I change quite significantly as Samantha. I am definitely more relaxed and probably passive rather than assertive. Once quite significant change is I feel so horny as Samantha. Its almost as though I slip into Girls wanna have fun. I realise that no ones life is all sunshine and a girl needs her quiet moments, its just my Samantha highs are girly sexy lively highs.

    I love it :~)

    I wish I could go en femme 24/7 , I’m sure the world would see a nicer person and someone would get a great lover x

  17. darleen evosevich 1 year ago

    hi girls im darleen im 53 i have prolem i can only dress whenno oneshome.i wish ihad an under standing partner.

  18. debbie 1 year ago

    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

    • Jenny1323 11 months ago

      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.

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