Brace for it, this is going to be a long one.


I've been crossdressing for a long time. I don't even know if I'm a crossdresser or a trans woman. I pondered the question a lot, but have no way of really discerning which.
I do wish I was born female, but is that enough to be trans? Anyway, I won't transition (for financial and social reasons, largely), so the question is largely irrelevant.


It started with sporadic incidents of borrowing my mother's clothes in childhood and teenagehood, that grew less and less sporadic over time.
Eventually, I bought my own clothes, whilst I was still living with my parents, arranging for delivery when they were on vacation (I stopped accompanying them on vacation around age 15). Hiding them was a challenge at times, but I still remember how ecstatic I was when they were delivered.
Over time, my collection grew, and I kept my secret for a long while.


After a very rough patch (jobless, depressed, suicidal), I sought treatment for the social anxiety disorder that had wrecked my life in many ways and, after some time, I nervously came out to my therapist. How nervously? I couldn't even tell her verbally (I tried for a couple of sessions, but chickened out), so I wrote her a note, printed it out and handed it to her with trembling hands whilst whispering "alea iacta est".
We talked about it a bit, and I was actually the one to come up with an exercise for once (cognitive-behavioural therapy relies on "exercises" in which you confront your disorder in a controlled context, record the parasitic thoughts and try to come up with reasons why they're not true or exaggerated): going shopping. My previous exercises had been unrelated to crossdressing, and felt like a chore. I was only doing them to combat my mental illness; whereas this exercise would be its own reward.

She proposed to go with me for my first time, and we spent a session browsing in various shops together. I was still exhibiting signs of anxiety, such as mumbling. I didn't buy anything. Obviously never tried anything on. Still, the outing had been a success, and no sooner had we parted that I went back alone to a shop and bought something (still without trying it on, of course). Don't even remember what it was.
Strange, I remember my second purchase in a shop (a grey silk nightie ... that I'm coincidentally wearing right now, actually), but not my first.

I instantly came up with another exercise for a future session: going out in full fem with her. Just for a walk. My therapist's cabinet (and home) was in the capital of my small country, so although her residential street wasn't too populated, we ran into a lot of people as soon as we got to a commercial street.
The results were mixed: although I clearly didn't pass (imagine a giant clad in a black satin skirt and black satin blouse wobbling on unmastered stilettos with poorly shaved leg hair inadequately masked by hosiery and a face adorned with inexpertly applied make-up), but most people made no comment (that I could hear), nor reacted much.
That is, until we crossed a school exit. By that time, unbeknownst to me, my concealer had thoroughly betrayed me, ruining any meagre chance of me passing.
The children could easily tell, and started yelling things like "hey, mister madam" and trying to take pictures. We ignored them and turned away, completely our loop back to my therapist's office. It was then that I noticed how back the concealer had worked out: it had turned a rather dark shade of brown, which on my milk-pale skin was much more visible than the beard shadow would've been.

After that, I'd sometimes change in my therapist's office and change back at the end of the session. I once drove back home in a skirt (I had parked very near her place). My therapist suggested coming out to my parents. I procrastinated at the task. I came out to my GP, then my mother and, a day later, my father.
Unexpectedly, my mother was the hardest of them. My GP was supportive, my father accepted it or rather was somewhat indifferent, but my mother really didn't understand at that stage.
Eventually, they saw me in full fem. I had improved a bit since my walk around the capital, but let's say the evening was awkward and I couldn't stop trembling during the meal.
Those 4 people are the only ones I've come out to IRL, and I'm not seeing the therapist anymore, nor the GP (she retired).


Henceforth, I sometimes ventured out alone, at night. A very risky thing to do, but I still wasn't in a great place mentally, so I wasn't being very cautious.
I lived in a very rural place, so the streets were mostly deserted for my late escapades, but I once walked along a very frequented road (yes, even at night). Got honked at more than once. I was walking with traffic, so they couldn't see my face and maybe the honking wasn't mocking, ... but that's not really better.
Went to a much less frequented road next time, where there is a pedestrian+cycle+tractor lane separated from the road by a metre of grass, with periodic entrances to allow rractors to reach the fields. A car stopped at my level, the driver talked to me, invited me in. I don't know whether he thought I was a hitchhiker of a prostitute (though if I'd been the latter, the spot would've been terribly chosen). Either way, I didn't want to get in. I was terrified by that point.
Maybe the man was well-intentionned and I offended him, but I walked on, stopping at the midpoint between two entrances to the lane.
My thoughts were to maximise the opportunity to run away should he try to corner me.
He stopped at the entrance in front of me and opened his passenger side door. I froze in place. He waited for what felt like an eternity, and so did I, immobile, eyes fixed on his car. Eventually, he drove away and I went home.

That experience cooled me down for a long time, but eventually I found myself driving to a nearby city and walking its streets in full fem at night.
Streets were almost deserted, and I was nearly back to my car when I encountered a group of people barely in their twenties. They didn't talk to me, but I heard jeers as I went past them. I think a couple of guys started following me for a bit, but some girls in the group called them to order.

After that, I kept my crossdressing to my own residence and my parents', until recently. But this is getting way too long and it's getting late, so it'll be for another time.
(yes, mockery had a more chilling effect on me than fearing for my life - that's what a social anxiety disorder does to you)


Sorry for the length, but I did warn you.