So who is Jess?

Well Jess is not my real name for privacy reasons.  I am a somewhat closeted Male to Female Crossdresser, somewhat as some people know but not a whole lot. I have a girlfriend of 5 years and a German Shepherd cross, they are both fully aware of my crossdressing though only the girlfriend is able to contextualize it.  I’m in my early 30’s and live on the Canadian Prairies.  I have a love for Politics (Liberal), Sci-fi (Dr. Who) and Sociology (working on my degree).

When did I start Crossdressing?  I have always crosssdressed I remember as a toddler putting on frilly little dresses and running around.  Borrowing my moms and sisters clothes growing up and always playing with the dresses and purses in the dress up box.  In high school I finally had the guts to buy my own pair of panties, a bras and a slip which was likely the most stressful moment of my high school life in retrospect.  Since that point I have over all intensified my crossdressing to the point now where I regularly crossdress and often wear panties to work, out etc.  I use the word overall as I have found over the years that I have gone through phases of how often I dress and there would be times I would go all hard core then leave it for a very long time.  I have never purged, I have packed away but never have I purged for a few reasons:

  • I love my feminine clothes
  • I knew I would do it again
  • I knew that purging would just lead to shopping
  • Bras are expensive
  • Buying womens clothing is not the least stressful thing to do

Why do I crossdress?  Unknown as I have stated I have always done it and though I have attempted to stop I have a burning desire to keep doing it so in my early twenties I gave up fighting it and just went with it.  In my later twenties I decided to see where this rabbit hole ends, a journey I am still on today.

That is all I am going to put up here currently, I’m sure I’ll add to this as time goes on.


4 thoughts on “So who is Jess?

  1. The only thing that comes to my mind about this title is “New Girl”,but apart from that just wanted to say hello 🙂

  2. I’m a man in his late twenties, and I practice every day crosdressing confidential.
    The tendency towards women’s clothing lasts from childhood.
    There was a lot of depression and frustration why I but with time I have come to terms with it.
    I’ve always been fascinated with femininity.
    When I started wearing women’s clothes did not have the internet but later when I got it, I realized that I’m not the only one.

    In public I’m in male mode and when I come home from work wear women’s clothing such as dresses, skirts, lingerie, high heels and a wig.
    Fully understand.
    What does the future who knows.

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