Ok this turned out to be super duper long, way longer then intended lol, sorry bout that...
Though I never had that "I'm a woman in a man's body" feeling or moment, I showed signs in my early childhood that I might be trans but never connected the dots because I never knew anything about this subject. I had a total male upbringing and everyone who lived near me were males so I only had male friends growing up; never was good at being social so I barely made any friends at school. I grew up playing sports and video games, once they became popular, and I can't complain, I love both still, but other than that, I don't feel like I ever really fit in.
Sometime in elementary school is when I began to "mess" around with my mom's clothes and even makeup sometimes; whenever I was alone so that I wouldn't be caught. After school I would play hockey and other sports almost everyday until it got too dark to see and also played video games with the same peeps.
In middle school and high school, my social situation started to change. People we used to play hockey with stopped or moved away, some of the people were older and either graduated or got caught up in other things. Occasionally we would get together and play and video games where still big for me. My brother, who is a year younger, started hanging with other people; once in awhile I would tag along as well, but they were "his" friends if that makes sense, not mine, and I didn't really fit. Later on I would learn about some of the things they would do that I wasn't aware of or invited to do. Some of them started dating and stuff around here but I had no interest really in doing so; the idea of sex and pregnancy was terrifying to me.
Another interesting thing about this time is that I waited a long time before I started to shave my face. By 8th-9th grade I had a lil moustache, beard and uni-brow lol. I waited a long time to shave because my parents told me that once I did it would grow in faster and thicker and I didn't want that.
I continued cross-dressing as well, even though my brother semi caught me wearing a bra; he felt the straps and asked me, I denyed it ofc

, played it off well I think, well at least nothing was ever said about it so who knows. I continued to wear my mom's stuff and had a secret stash in the only bathroom in the house and I would spend hours in it lol. I started getting "bored" with her stuff, I guess you could say, and started stealing stuff. A nearby thrift store would sometimes have bundles of clothing outside their store and I would dig through it looking for stuff to wear. I also started going out and shopping for stuff, which of course is scary as hell.
Things stayed like this for quite some time. I definitely got caught once; my mom had died and my brother had moved out with his g/f at the time, now his current wife, so it was just me and my dad now. One day I was washing my clothes and I forgot about them in the dryer, when I woke up I found them stacked on top of it and I was like %()$*)#()#($ (insert expletives). When questioned by my dad, I said I was washing them for a friend lol (so lame that one right?!?). He was like ya right, I see your mom's stuff in there, throw them away, which I did (only temporary tho, retrieved later from trash), but thankfully nothing else was said about that.
Up till this time I was still basically clueless about things. Never would've thought I might be trans, never thought I was a woman, never even thought I was a cross-dresser, I just thought I like to wear women's clothing. Still never had a gf, never had sex, nor did I really try or seek it out; I just felt undeserving of it and uncomfortable with all that.
Around 24 or so I met a girl online while playing a lame game and that's where things started to change again with me. Never met her irl though I wanted to nor ever really "spoke" to her, just messaged each other and played together. I called her my gf but she would say I was just a friend, if even that really, if asked about it, but anyways, I ended up falling head over heels for her. Somewhere/time in our relationship my thoughts switched from damn, I wanna be with her and bang her to, damn, I wish I was her. Started imagining have sex with her but I was her and she was me if that makes sense. I think this is because sex as a woman is more appealing to me than as a guy, possibly part of the reason why I never tried to get with anyone before.
Things continued to move forward from there. Randomly messing around on the 'net one day I discovered a "drag shop" for lack of a better word and realized I had to go there. I ended up getting breastforms and some other feminine clothing and planned on going on vacation dressed as a female. I did go on the trip but couldn't muster the courage to go out dressed. I knew I would be seen as a man in drag and a poorly dressed, half assed one at that, and hated the thought of that.
Shortly after I got back I learned that there are ways to feminize yourself and grow boobs and such, and I was like WTF, NO WAY! Here I am, a 20 something year old, who I consider to be quite smart, taking all kinds of science and other classes, in college and pre-nursing, and I am just now learning about this!!?!?!?!.....Needless to say, it did not take me long to realize that hell ya I wanna do this, even though I wasn't a believer and thought I was just gonna get scammed, and I started like the next day.
It wasn't until I found Susan's, I'd say around 6 months or so ago, and started reading everyone's intro and like 1000s of post that I started to realize that, hey, a lot of this sounds familiar o.o, maybe I'm trans lol. For me, reading and learning about everything and seeing the changes that people have made made me realize that hey, maybe I could actually do it and not be seen as a man dressing as a woman. If I would've had access to the internet earlier I might have realized this long ago but I wasn't allowed to have it until I was like 22 because my parents thought I'd get id thefted and all the other horror stories that the internet can bring.