Friday, May 29, 2015

The Life of Cross Dresser, Jessie Pierce

A longtime customer of, Jessie Pierce is now a huge inspiration in the CD/TG community. She has found a real passion in helping others feel more comfortable in their discovery of becoming a cross dresser. Like most cross dressers she was not always this confident, it was a gradual process and she still works on it daily. She went through most of her life not dressing, so she can relate to the struggle one feels with gender identity. Now that she has discovered Jessie she has blossomed into a beautiful woman who loves to help and share her wisdom with others in the community. Jessie was kind enough to share her story with us and all of you.

Jessie Pierce

I started cross dressing when I was 49-years-old, four and a half years ago. My first experience with women's clothing was when I was only five-years old. I hid under my mom's desk and tried on her pantyhose. I remember putting them on my legs and rubbing them…it made me feel like I never had before. They were the smoothest silkiest article of clothing ever to grace my 5 year old body. I was in a trance.
 I never did anything like that again, until I was 49.
 I was always an emotional guy and that sometimes was used against me. In relationships I’d take on the stereotypical ‘female’ role…emotional…wanting to talk about feelings and connect on a much deeper level. I had a personality that I felt was a huge weakness most of the time…And I can say there were many times I loathed myself for it. I wasn’t the stereotypical male but I had been called a “man’s man” several times.

At the age 49, I started wearing thigh highs and panties. I remember reading an article about a guy who did that too, but he liked to paint his toenails and look at them while he walked around. I thought there was no way I could go that far with this. Guess what? My toes are never NOT painted now. As I progressed in what I wanted to do with my girly side, makeup entered the picture. From the time I started using makeup I spent the next two years getting made up EVERY night.

I spent those two years learning all I could about being a girl for the simple reason that if I was going to be a girl sometimes, then I was going to BE a girl, for me. I was passionate and that passion continues to grow. Every day I get the hope that tonight I’ll get made up, though it doesn’t always happen. Even though I don’t get made up every day, I do wear girly clothes every day for the simple reason that I feel the most comfortable doing so.

YouTube has been a great resource for my development, and I can’t imagine what it would’ve been like without that. I looked up makeup tutorials, feminine movements, gestures, walking, walking in heels and so on. I learned there are a lot of guys who love to cross dress, and they didn’t look or act like some weird creatures from the back alleys. I learned there are some guys that are more feminine and beautiful than genetic girls.

Now I have a YouTube channel with 5000 subscribers…who watch me dance (or move) to songs while being the most girlie-girl I can be. They watch me and thank me. Really? For doing the thing in life I feel most passionate about? How incredible, what a dream. This is the LAST thing I would have ever thought I’d be doing…in fact it wasn’t even a thought. I get a lot of messages from confused guys, married guys who don’t know how to make dressing work within their marriages let alone how to tell their wives about their feelings/desires. You’re not alone I promise. We all have different reasons for dressing as well as some similar ones. It’s simple, complex and complicated…I think that’s pretty neat. If I could make one thing stick with you it would be to go explore…see where this may take you…accept yourself…and, HAVE FUN!
We hope that reading Jessie's story will provide a little inspiration to your day. We are thankful to have her as such a loyal customer to and really appreciate her contribution to our community.

Jessie loves to give back to the community and encourages you to reach out to her with any questions you may have.You can visit her You Tube Channel and send her a message through there- 


  1. Quite a nice article.
    Thank you.
    Nancy James

  2. Hi Jessie:

    you look gorgeous [that's a genuine compliment] but it is so much easier to cross-dress openly when the end-product is gorgeous...what about the 'inner girls' who are not so lucky?

    i wish you luck and continued success, but i can't relate and the ridiculosity of my own alter-ego always haunts me...

    the inner [real] me can be out there having a lot of fun, but the first mirror i see 'pricks my bubble' in a way that is exactly opposite to my needs!!

    so good luck, but can we have some 'ugly ducklings' who could be [for us, well me] role models while we admire the 'swans'


    If anything sounds negative, please take that in the context that i am still here reading every email i get from you :)


    also as a PS 'what the what' was going on from age 5 to 49? that's the story 'I' would like to hear, Rosa

    [excuse the knee-jerk, i will dutifully go over to your blog and glean the answers there, R]

  3. What a beautiful story! Jessie is such a wonderful inspiration.