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I am a private person and prefer being en femme to relieve stress in my home, accomplishing domestic chores. I know that sounds boring. The idea of mingling with the masses does not appeal to me. I do venture out for evening drives and strolls to satisfy the urge to "just do it!" The times when I went out with the intention of being among fellow humans has been at Halloween.
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I think courage comes much more from the desire to be myself than from the absence of fear. At first, I went out to more discreet places, or accompanied by people I trusted, until I felt confident. I still get butterflies in my stomach sometimes, but I've realized that most people are more concerned with their own lives than judging me.
I've met acquaintances once or twice, and I confess it was a shock at the time, but in the end, they acted naturally. I think the key is being at peace with who you are: when we accept ourselves, it becomes easier to face any situation.
Translated from Portuguese by Google.
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It occurred when the need to go out dressed was greater than my fear. Once done, it just became easier.
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Perhaps some day I will get the courage. To me another component is wanting to pass and not viewed as a guy in a dress. I know some are ok with that and much respect to those girls.
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I have no interest in passing, and I doubt it would be possible. That said, I try to push my own boundaries on what a guy can wear in public. I've traveled in leggings many times. I often wear obviously women't t-shirts. All of my tank tops are from the women's side, most are racerback and some are fairly low scoop. And I have many pairs of short yoga shorts. All of these I've worn outside either in public or out front as cars are driving by. Just trying to push the envelope on what's "normal" wear for guys.
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It started with blending. Wearing some fem jewelry. Wearing leggings, painting my toes and wearing flips or sandals.
I still get nervous but once I get goibg it settes down.
Hugs,
Jenn
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Courage is not the absence of fear but rather the assessment that something else is more important than fear. —Franklin Roosevelt
Courage is being scared to death and saddling up anyway. John Wayne in True Grit
If I am afraid to go en femme to places that ordinary women in my culture routinely go, what am I afraid of? Myself.
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I go out every couple of months. Usually it's just for a day/night, but sometimes it's for several days in a row. I pass, more-or-less.
That being said, for me, going out as Sherry isn't a choice: it is something I innately NEED to do. I could choose not to do it -- and I made that choice for a long time -- but it was killing me inside.
OTOH, I'm lucky in several regards: 1. I live in the northeastern US, which is mostly safe; 2. I'm 5-7 and not muscular, so physically passing isn't too hard; 3. I have a supportive spouse -- I didn't always, so going out was harder back then, but it certainly makes it easier now that hiding isn't an issue.
And with THAT all being said, yes, it still takes courage! When I started going out, I was scared beyond belief. Little by little, I learned how to pass, how to be safe, and how to feel comfy doing it. Many years later, that first step out of my home is still a bit nerve-wracking!
To the OP's other question, no, I never ran into anyone I know while out dressed. I had a single close call, but avoided detection.
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My courage came with age and of all places, the burlesque community.
For years I was a closeted crossdresser, it was a secret, and it became a habit of keeping it a secret. When I first met my now wife, I decided I needed to be upfront with her, I didn't want to it to be discovered. She could either work with it or not. Now we have been married for 15 years. Just before we got married, she bought me a gift of a series of burlesque dance lessons. I went into these classes knowing I wanted to learn to walk and dance in heels confidently, do an alluring stocking peel, all of the same things the women in class were learning. They were just as nervous about themselves learning to strip as I was. It was a bonding experience, and we formed friendships.
This new group of friends had known from the start; there was no secret to hide. Over the course of 11 years I took more classes, some of the people I met originally formed our own little troupe, I developed a few acts and performed locally. I had two different worlds, those who knew and those old friends who didn't.
At some point, having experienced so much acceptance within the burlesque community, I came to the conclusion that I kept it a secret not because I didn't want others to know, but it had become a habit. There was no real reason I shouldn't be able to tell everyone. This may not be the same for everyone, but I truly didn't fear losing friendships over my being a crossdresser. One day I just bit the bullet and told five of my male friends as we were up at my friends' cabin. No one got angry, no one treated me differently, it was just out there. I have since told multiple other friends.
The timing of this specific thread is pretty fortuitous. One of my burlesque friends is producing a show in three weeks and asked me to come out of semi-retirement to perform an old act. None of my old friends, who I had been keeping my secret crossdressing from, have ever seen me perform. Now that they know, I have 14 old friends who are showing up to see me perform for the first time.
It's not a secret anymore.