This might not be entirely accurate. My memories have clouded over the years, as they do, and I chose to forget quite a bit, so this is probably missing information. I don't think it's that important though. I only started crossdressing this last year, which remains in memory. I hadn't thought much about talking about this before, but @VikingNipples posted about their history, and I thought it was interesting, so I decided to share mine. I don't know if many people will care, or even read something from this subverse, but it's nice sometimes to talk.
I don't identify myself as a man. When I think about, I don't think I ever have. I was myself. Some people seem to believe that the gender attached to toys children play with determines their personality; that somehow a boy who plays with Barbie dolls will become girly instead of masculine. Obviously, that's not true. Anyone can tell that. I always had typical boy toys. Action Man, Transformers, Batman, that kind of thing. Back then of course, I was in Primary School, so boys and girls didn't really hang out much. I didn't think much about it.
Come to think of it, that was the closest I got to anything outside of male gender roles for a long time. We had a day where everyone was to come in dressed as a character from a book, or TV series or so on that they liked. Like non-uniform day but with fancy dress. I can't really remember the details, but I wanted to dress as a character from a book...If memory serves, she was giant that came out of the ground. That's not very specific, but it's all I remember. I've not read that in over a decade in all likelihood. I no longer remember the title. I was really looking forward to it..I was told I shouldn't, because the character was a girl, and obviously I wasn't, but I wasn't much bothered. I got ill and couldn't go in the end. My younger self was very disappointed.
As I said, that was my only experience really of going outside typical "boy behaviour" for a long time. That said, I think in retrospect I was barely in the boy zone. Especially in Secondary School. I could never relate well to the other boys in my year. Their attitudes, their interests were completely different to mine. It seemed they were trying to put on a more tough, masculine image as they grew. In Year 7 (About 12 years old) people seemed fine enough, but after that, people started to change. The boys were trying to act tougher and do more typical male things (football, talking about girls more like objects,) and the girls suddenly became quite concerned with their makeup and gossiping. That's how it seemed, anyway. I didn't speak much with the girls because I had no makeup to talk about and don't talk shit about people behind their backs.
As that went on, I noticed more the differences between who I was and who other people appeared to be. Things men were expected to do, I had no interest in. The way men were expected to look..I.I spent like ten minutes trying to write this sentence actually. It's difficult to put precisely into words. I think the easiest to understand would be to say that I didn't identify with it. It seemed like something that should happen to someone else. I was happy as I was. The idea of looking like what a man was supposed to look like ate away at me. I didn't want it.
One day. I was wondering what the term "transgender" meant. I'd heard it somewhere. I looked into it. First the definition of the term itself, then experiences of people who were. I found I could identify with them, quite strongly at times. For a time, I believed I was transgender. It wasn't nice to think. Considering my changing body, and the experiences I'd read about of others, it seemed like it would cause me nothing but adversity. My family seemed dismissive of the idea at best, and in at least one case disgusted, based on their reactions to a documentary that came on for a few weekends in the summer once. I discovered the term "androgyne" on a certain forum, alongside standard transsexual and crossdresser subforums. I'd never heard of anything like that before. A gender (identity), but not male or female? It's understandable that it's dismissed by many people when most would never give the concept a stray thought. "Then...I don't have to be one or the other?" I thought. These people sounded a lot like me when they described how they felt. But what they did was like walking the line. They did as they pleased, presenting as one or the other, or ambiguously, to match their feelings. Sometimes you'd find a transman or a transwoman posting there, who was going through HRT but didn't want to be completely female. I'd never thought that a person could do that..to create themselves, instead of adhering to the box they were born into. Not in terms of gender role, but expression and identity. I realised that sounded like me, and took up the term. Being referred to as a man always stung anyway. Even today, if that happens, it spoils my mood for the rest of the day.
But what could I do about it? I was still in Secondary School, and lived with my family whose opinions were either unknown to me, or known to be less than flexible at best. Still, I just went along with my life. Fortunately, I didn't end up being very masculine in appearance. I ended up relatively tall, but fairly thin, with a relatively soft shaped face for a male. I was told once or twice that if I were put in makeup and a wig, I'd look just like a girl. I didn't show it, but that made me happy.
Still, by the time I was 16 and in college, the thought of crossdressing hadn't occurred to me. I wanted to be androgynous, but I didn't believe it was possible. "I can't do that!" I'd have said. It was as I'd thought of being MtF before; too much adversity. I think if we met, my younger self would be quite surprised. I remember I used to envy the characters in gender bender manga because, being anime-type characters, they could change their apparent gender easily, and look androgynous without trying. I don't remember when, precisely, I decided that I would definitely crossdress at some point. I think it was while I was talking with a transgender friend of mine online. I talked a bit about this subject, and she said I should do it. I thought a lot, and decide that I would. One day, I will be old and unable to pull it off at all. I might as well do it while I can. I started with a skirt and a top and some other minor things, but I wasn't satisfied just with those. I want to appear androgynous, yes, but I also like the idea of being able to disguise myself as a woman. I think I picked it up from all that gender bender manga. Besides, if I'm effective all the way, then androgyny is just dialing it down, isn't it?
I was on Reddit by that time. They have a crossdressing subreddit, but I don't post there. I suspected, and still do, that it has a lurker population. Attractive/convincing crossdressers get upvoted a lot, while those are unattractive, unestablished, or just starting out don't really. I didn't want to post in a subreddit where I'd be unlikely to get much advice, nor one that was fairly popular for what it was. I'm very selective about posting photos of myself. I left Reddit after a while, anyway. So instead of posting on the internet, I'd just take photos, and if I could stand how I looked, I'd send them to my friend for advice and general feedback. She was very encouraging.
When I found this subverse on Voat, I subscribed, but it only had 4 users then, and no posts since the day it was made. Since the moderator hadn't posted anything, I requested it. It was relevant to my interests, and I hoped to make it into a community of people I could talk to and share my experiences with, and post without fear. The subscriber count is now above 10, which makes me happy. I don't know where they all are, though, I rarely see them comment. I think they don't see posts here because with a small community, they don't get many upvotes and are buried.
Still, I'm glad I did end up crossdressing. It feels good to appear more like myself. I've chosen to live this way. I won't waste my life trying to be someone else. It's too short to waste pretending to be a man. I hope this long wall of text was at least interesting to read for someone. It's not necessarily useful information, but it's nice to talk about sometimes.