How Wearing Skirts is Changing the Way I Look at the World–for the better.


I’ve been going out and about in clothes gendered female now for a few months, after my first time doing it “naturally”.  [Written about here]. By that I mean, in life, not just to costume parties.  I have been dressing privately for a long time of course, wearing women’s clothes at home.  This has been going on for a very long time…and for the past few years, when I have been working so much away from home, has been more constant than dressing in male attire.

My choices tend to the more classical, a bit conservative, and this is largely the result of what I have found attractive in women.  Power dressing.  Pencil skirts, white blouses, corporate-like clothes.  I will admit to a fondness, however, for skimpy and flouncy short skirts.  Anyway, after that first time wearing [written about here], and the feelings of elation that accompanied it, I have basically stopped dressing like a man does.

There is a tremendous letting go of fear that has accompanied this…and while I might like to think that this is exclusively my doing, the fact is that the people I have interacted with have also helped.  My therapist (s) say that I should not be looking for validation from the outside, so okay, “officially” I am not looking, but I do appreciate it when it happens.  I am also not alone in that I have an encouraging Mistress with whom I have been able to share some moments dressed this way.  And two of my closest female friends have always known, but until recently had never seen, but now they do.  And they have been nothing but encouraging.

To be asked for advice on dressing—what to wear with what—is the ultimate compliment.  And, of course, all of my therapists, that’s a confession, because I am seeing quite a few of them (I have a hard time whittling down the list to the one, and since they all give different things, I am keeping 4 of them for the time being), all of them are very encouraging…

And I am finding that the more I do it, the less I think about it, the less I need to get “psyched up” or to give myself a pep talk…and I am just doing.  And while it is a little odd that my hotel receptionist told me after I appeared in a dress that they like to google their guests, and he was like, “wow, did you really do such and such?”  And there were these people looking on, and there I was in my nice new warm wool tights my favourite new skirt—soft woven cashmere to the knee and wearing a men’s dress shirt because that’s what I am flying in this evening—so looking half of this and half of another, but frankly, it looked hot.  I say this, because this is a hotel where I have played with Mistress the only other time I have stayed there, and they put notes in the system about a guest’s predilections…and boy, mine must be a long list!  

And since when I checked in the woman said, “I hope you have as much fun there this time as you did last time,” I was thinking, ‘how much do they know about fun?’

But the purpose of this post is really more about the reflections of how people react.  Which I find quite intriguing.  I know that generalising about age, race, sex, etc is horribly inappropriate, but I will do it anyway, because I think I see patterns, and I would be really curious to hear the thoughts of others on these topics.  Rather than making value judgements, I will just highlight standouts.

  • The group of Mexican builders who carried my suitcases and helped me hail and get into a taxi
  • The black woman who pulled me from the checkout line at the supermarket, called me “baby” and checked me out in another line
  • The white woman who told me she liked my sweater just after a white woman as tall as me and her husband were whispering and staring at me
  • The white man at the checkout counter of the hotel who changed his mannerisms from classic male to more effeminate when he talked to me…the black man who did the same after serving me a coffee at the train station
  • The white middle-aged man who looked me up and down, and couldn’t stop staring at me in the little compartment on the train we were in today, while his wife stared at him
  • The young middle eastern boys who sat opposite me on the train and smiled smirkily when they sat down, but then studied me with curiousity during our ride, and their parents sitting next to me who looked from them to me but never said a word.
  • The conservative white couple who couldn’t stop staring at me on the train
  • The super tall white construction worker who admonished his workers for not holding the door for me, and then used his own key to get my elevator button pushed, then walked out of the lift head held high without ever looking at me or saying a word to me with them tagging along behind him
  • The older white construction worker who pointedly refused to say good morning to me in the elevator this morning as I headed out
  • The woman I flirted with at the bar who served me wine was so much friendlier with me this second time when I showed up in a skirt for a drink
  • The two women who helped me in the wine shop nearby who were so much friendlier to me dressed with a skirt than when I went in wearing trousers the previous time

There are so many examples.  Many people, mainly men, will make a point of not looking or looking away.  Am I making them uncomfortable?  In a way, I hope so.  They’re just clothes.  Right?  But I also find another pattern, and this is where the generalisations lie…in dangerous territory.  I have touched on this a bit before when I wrote about my exercise gear and beach attire.  Blogged about here.

I am finding that non-whites are generally more obviously tolerant.  African-American women have been by far the most outwardly warm and encouraging.  By far.  Latina women have had more nuanced reactions, which have ranged from curiosity mixed with sexual attraction, to a total sister feeling, to near hostility (though this only once).  Young white women have been very positive, without saying anything, but with big-hearted smiles.  At worst, they have just not paid attention.  African-American men have been totally nonchalant, as if they don’t even see it…not that they are avoiding it, but just seem to accept it.  Latin men have had a range of reactions, from very gallant to curiousity to avoidance.  White men have had the closest feeling to hostility, though nobody has been outright hostile.  And plenty of white men have been friendly, though I think that these are more in the LGBTQ camp, while most are just avoidant.

These reactions are of interest to me because I wonder if minority groups recognise that I have signed up for discrimination, and therefore, see me differently than they might otherwise.  Is that what is going on?  And I am wondering if a white man might regard me as a traitor to the cause.  I know these are gross generalisations, but what do you think?

Separatel, what do I find in myself by doing this?  This is the best part.  For one, I find intense pride in my courage.  I am not trying to toot my horn or to ask for feedback with that statement, but I know how long I cowered in fear over doing this—“what will someone think”, and I know so many people in the community struggle with this.  In fact, one of the most terrifying things I recall reading growing up about sex change operations was the now-outdated dictum that you had to live for a year as a “woman” before they would even allow you to start the hormone process…we have come a long way.

I can’t look back now.  I have begun to taste liberation.

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