More Thinking. More Progress? Destination?

So, in light of recent events and how things have changed over the last few years, as well as finding my mind wandering, questioning what is going on, I have decided to list everything I can remember with regards to how I’ve thought about this crossdressing thing and how my thoughts may have change. Or where they always that way, I just didn’t read the signals then, the same way I do now?

Some points that follow I have mentioned before, others never.

Childhood (7-11 years old)

  • I remember the girls at school wearing the school uniform skirts, doing handstands against the wall and showing their undies and me thinking I would like to wear those.
  • I went to a Cub Scout theatrical performance where a number of the boys where dressed like “angels” in white dresses. I was jealous, I wanted to dress like that.
  • That time I wanted to wear my sisters nurse uniform (too small) but turned my police one into a girl’s version using my sister’s black cape as a wrap skirt. Why? No idea, but it felt great. Not so finding out my mother had taken back her nylons I had stashed under my bed. That was a major downer.
  • Continued sneaking through my mother’s stuff as “we” so often tend to do, loving the image the mirror projected. Never questioning.

Youth (12-18 years old)

  • Puberty was starting. Sister’s too. I tried on her training bra and wondered if this might cause my breasts to grow. Remember the first “real” bra I wore, a Daisy Fresh front snap closure.
  • As a kid, ever remember the story of if you crossed your eyes and looking in the mirror at midnight, you would stay cross-eyed? I tried that while being crossdressed. I looked like a girl, would I stay that way after midnight? Why would I even tempt fate if that’s not something I wanted?
  • I wore my mother’s bathing suit. It had semi rigid breast cups and tummy control. It provided some hiding factor to my maleness, but that’s the first time I remember tucking things away, to look like a girl. Then I thought if I can do this with a swim suit, why not a bikini? That quickly moved onto sisters smaller panties and bra (which, like so many girls that age, I stuffed with toilet paper). This was all done with the aim of looking like a girl. And I never thought anything was wrong with it.
  • I tried pushing “things” back inside my body to hide them. Didn’t work.
  • All through this time (and still do), I looked at girls and wondered about dressing like them. Their hair, make-up, clothes. After evening Drives Ed, the school was empty, so while waiting to be picked up, I’d sneak into the girl’s bathroom and experience a sense of…I really don’t know how to explain it…it “felt” good to be in there.
  • In grad 12, one of the girls can to school in a skirt suit as she had a job interview right after classes….I was SO FRIGGING JEALOUS of how she looked. I SO WANTED to look like that.

Teen to adult

  • I would be remiss if I didn’t say that dressing also brought about arousal and pleasure, but ALWAYS followed by guilt and shame. After the purges, deep regret for having done so. Like I’d lost something that I may never get back.
  • On the farm, when I’d find myself alone, I’d dress in my sisters barn clothes to do chores. I mean everything she wore! I wanted to be like her.
  • When I worked overseas on an exchange program, again, for whatever reason, I wanted and did get out while dressed. These where my very first excursions outside of the safety of my room. Went for a drive, walk in town, cycled. I wanted to be seen as a woman.
  • When I can home, waiting to get into the Forces, there was a compelling need to go beyond dressing in the apartment. A needed to get out and be seen and interact with society. Always nerve-racking, but also enjoyable.
  • After joining the Forces, there was two Halloweens, a winter carnival with a Womanless Beauty Pageant and an Octoberfest that were used as “excuses” to dress. Again, I enjoyed being out.
  • On two occasions, while driving from temporary posting to the next, I chose to dress for parts of those drives. But why? It would have been so much simpler to just travel as “me”. I’ve never really given much thought until recently, as to what the motivation was. I just wanted, or needed to do it. Now as I think back, I may have started out nervous, but it did indeed feel great to be able to do it. Dare I say, as I’ve most recently written…it felt comfortable.
  • A couple of times I drove 50 minutes to the nearest airport just to wander around. No thought given to “what if something happened”.
  • I stifled the desire to get out once we started a family. The thoughts though never went away. The “want” has always been there.


  • Most recently, through the fantastic invention called the internet, I have been able to reach out to others around the world. Read, write and exchange thoughts on what makes “us” tick. I’ve learned much about myself, but with each passing experience, although I keep learn more,  I’m also left with newer questions.
  • Am I now also experiencing the “finding ones true self”? And if so, what the hell is it? I used to describe myself as a “hetero-crossdresser”, but I’m now thinking there is more to me than that. There is a deep seated desire to be much more than just my male self. I know there is always a process of maturing and education throughout our entire lives, but while reflecting on my most outings in Ottawa and digging deep into the recesses of my mind, there seems to have always been a part of me that has wanted to show/express my female persona.
  • I know there are many who have gone through something similar and can relate.
  • And the rhetorical question re-appears…Where is this taking me? Time will tell I suppose.



  1. I think you have to have lived some aspect of transgenderness (as an umbrella term for any number of ways we need express a sense of the feminine) to be able to understand your story.
    And I do. Before this aspect of my personality hit me later in life (or shook me out of my entrenched male persona) I doubt if I’d have made any sense of it at all.
    As to where to for you, it is very concerning not to have a clear direction of where we should aim.
    And there are a miriad of complications that affect where we might end up. Family responsibilities, acceptance or rejection, employment, social support, health, age, and on and on.
    But your story makes full sense to me Michelle.
    Counterintuitive though it is maybe we don’t need to know all aspects of whereto from here. Maybe it is most important to realise you are this complicated personality. You are unique, valuable, and lovable. Your feminine is complete regardless of who recognises her and regardless of the direction you take to express her in you.
    Congratulations on realising her and expressing her as you have to date.
    I have followed your progress over the years from your voice videos to your most recent. Real progress missy! Need you go further? I have no idea and maybe you do or not.
    And maybe those close to you respect themichelleinyou or not.That is their choice in the end. But you must respect her because she is a part of the whole you.
    I look forward to following the further chapters of your story.
    With ny best wishes my sister,

    • Thank you so much Geraldine for your kind and thoughtful comments. I know that with every step that is made “outside the box”, the chances of putting anything back into it diminish. I talked about re-finding a balance…hard to do when the weights at the ends of the scale keep changing. I’ll just keep working on it.

  2. Jessica Winecross

    Hi ya Sis! I’m thinking of posting my manifesto here if it’s appropriate. Let me know. Hugs! Jess.

    • Go for it Sis. I’m here to support you! 😉. M.

    • Though I should have really replied, ” do as you feel comfortable with” 😊

  3. Outstanding post! I have to say that you trying on your Mom’s swim suit was exactly what I did. The One piece suits in the 1970’s had built I cups and it felt so good to me.

  4. Joni Ria

    Hi Michelle, love your blog! Am on Flickr and have been following your pux with interest. Just discovered in a recent comment exchange you had that you are only a part time lady! Wow!
    Quickly just want to say how closely i can relate to everything you’ve posted, including your graph!
    – Comfortable – exactly! Just comfortably me. Content, normal. How i felt when i finally tested the waters fully at age 45 and accepted myself for who i am. See my Flickr bio. I consider CDs part of the TG spectrum and call myself a part time TomGirl. All for now, more later… so nice to find yet another person like me.
    Sincerely, Joni

    • Thanks Joni.
      I realize my blog is in dire need of a major update; much has happened since the last entry. In the mean time, I guess the updated Flickr pics that appear on the side kind of do the talking for me. 🙂

  5. Hello Michellerdeere,
    I am glad you are still posting (I see your response date is July 2019.) I too need to work on my website. It is a funny thing, I journal almost everyday. My intention was to write down my thoughts during the day and then transfer them to my website however by night fall I am very tired and just fall into bead.

    As a side note, I have recently started a time line just like yours. I am wanting to document every memory of anything that promoted my wanting to dress like a women. Why am doing this? Possibly to better understand myself. Possibly to see if I can shake lose a hidden memory of how it all began. Possibly to finalize my journey and pick what I want to do with this gift.

    I do feel we that can travel back and forth, dressing as a male and then dressing as a female comfortably is a gift. Very few can do this.

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