Origins of Jess the Crossdresser


Sometimes it seems crossdressers are like superheroes as we live a double life, have secret identities, and we all have an origin story, if you look at my avatar i used an obvious homage to this idea.  I was scrolling through the comments on the So I’m a Crossdresser now what? page and there is a number of people started to write about their first time dressing up and I have never done this on this site.  Mostly because I have never had the need to, but since others are sharing so I’ll do the same.

The Origins of Jess the Crossdresser

The earliest moment of me choosing to wear a dress I was really young, perhaps four or five and I put on a frilly dress and walked around.  Of course at age there were very few social repercussions and it was likely considered cute.  As we age however that changes and we learn that there is a gender line that is not be crossed.  Luckily as kids we are allowed to play dress up and there is always a steady supply of dresses in the dress up box.  At these young ages it is the outerwear that is of note and the idea of different underwear never really occurs to us.

As I aged the part of me that wore a dress for fun was hidden more and more thanks to social pressures.  Though two things did change as I aged: The way I enjoyed women’s clothing and that underwear become interesting and the new focus.  While I routinely engaged in crossdressing and had those confusing thoughts as to why I felt this way and felt this need.  There was a dress up box in the house or old clothing would be discarded for children to engage with our imaginations more fully, I’m sure many of us have access to these resources and can understand what happened. While there was a wide selection of clothing are available in this dress up box in the basement it was obviously the old dresses and purses that drew my attention but even at this young age I was quickly realising how unacceptable it was for me to have these desires for these pieces of clothing. My most vibrant memory is actually from when I was in grade six so about 11 years old and I had a dream that I was wearing a bra at school and was found out, though strangely no seemed to have had too much of an issue with it.  That dream was so real I could feel the bra strap, and then I woke up a realised there was a fold in the sheet where a strap would normally go. The rest of my elementary school years were spent dressing in clothing from the dress up box and items borrowed from my mom and sister. It is always interesting to me that cross-dressers are attracted these items of clothing well before our sexuality has become fully realised leading me to believe that it is not just a sexual thing for us there is something else going on.

In high school I was out of town for an appointment in another city and I decided to buy some women’s underwear.  I went to a dollar store and got myself a black bra, pair of panties, and a slip for almost nothing.  The bra was actually terrible but unlike all of the other women’s clothing I had worn up to that point it was mine and never had been worn by anyone else.  While I was in high school the Internet was also coming of age so I was able for the first time to reach out into the digital world and find out that I wasn’t alone.  I remember very distinctly the realisation that I was in awe on and how comforting it was which is one of the reasons that I started this blog was that hopefully by putting myself out here somebody else would take comfort in it and realise that they themselves are also not alone.

When I moved into a basement suite on my own with no roommates your family members around I was able to much more fully engage with my cross-dressing as I no longer had to hide my panties and bras  and I could just have them in a drawer or laying around and no one would be around to question it. I also did not have to worry about somebody walking in on me and discovering my secret and so I was able to spend hours a day wearing women’s clothing without having to be disturbed by anybody else.   In retrospect I think it was during this time that I started to become much more at ease with crossdressing.  It was also during this time that I gave up on the dual personality that many crossdressers have as I have stated on several occasions it is just me there is not a he and she inside of the same body.  I use Jess as a pen name and nothing more.

I am now in my thirties and have a spouse who actively engages with my crossdressing and I am able to do it whenever I want.  So really I am living the charmed life right now I suppose, or atleast the best I can hope for.

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2 thoughts on “Origins of Jess the Crossdresser

  1. I enjoy your writing. My sense is that you and I see our cross dressing in a similar vein but I am likely twice your age and my wife is from an earlier generation than yours.
    Keep writing.

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