Should I/Could I/Would You?

I think transitioning is such a big decision...

Ever since I've been conscious, I can remember feeling a certain way. I felt like something had been robbed of me "down there". My mom really wanted a girl and she got me. As soon as she tried to dress me up, I put up a fuss. From even age 2, buttons and flowers had to go. As a 5 year old fan of the Backstreet Boys, I didn't have a crush on them nearly like I just wanted to be a part of them. I dressed like them, oversized t-shirt and cap and all. My mom eventually let go of trying to dress me up. Walking into WalMart for clothes, she'd walk us to the girls' section and I'd break off her hand to go running towards the 6x rack of boys' clothes. I walked home with a brand new Raptors jacket that day. It was purple and sporty - - and I adored it.

School, before and in kindergarten, was where I learned. I loved to learn but was easily distractible. Especially by the young boys. I often had a crush on one. I "confessed" my "love" to a few. Some of them I, ah, "dated". Others avoided me from that point on.
I soon learned that in the classroom, like everywhere else, girls rarely had the big kinds of personalities exhibited by a few boys, or the teacher. I was always a happy, energetic kid but found myself stifled in school. Not actively stifled, but as a result of the energy around me when it came to the other kids. I felt unwelcome among the boys and I just wanted to do what they did. I ended up hanging out with a few girls but felt dull inside very often. It wasn't like being at home.

Puberty, highschool… I didn't do much. I did nothing at all. Private school was what it was. But as soon as I was out of high school, that's when things started changing. I cut my hair short, wore funky colours, went to an uber-political-hippy school downtown in Fine Arts, learnt to draw from a real teacher (because I drew my whole life, one of my school distractions), moved to a different town with my mother, etc.
I left that school and went to a closer one where I started smoking weed. First, casually. Gradually, I became a smoker over a span of 5 years. The first two - on and off. The last three… daily smoking.
I had some experiences with men and dating. Mostly it was disappointing. I was always so horny and it felt good, yet I couldn't come. Again, I felt like a part of me was, truly, missing. And I felt unable to stay aroused at the sight of an aroused male in front of me.
A few more years have passed, since then I've been through more and more soul-searching type ordeals, from moving across the country on a one-way ticket, trying mind-expanding alterers and being blown away by the answers gotten back, made new friends and met men I felt more kindred with, more in sync with.
I'm back to my original city, living on my own. I understand that, within me, there is a conflict. From making love to studying to expressing myself, it's hard to stay focused because I feel like the body carrying all these messages is wrong.
During my time smoking a lot of weed, I went full-on androgynous. I even got some binders. I got pretty thin and the only thing that was working against me was my height of 5"4'. I've always felt "taller" in my mind, so I must seem like I have a Napoleon complex to others.
I feel like this body is preventing me from being who I am, from the exchanges I have with my outer World to full-on inner conflicts like masturbating air or being insanely attracted to men… I'm a confused individual.

I've only recently started coming out of dissociative depression. I'm still working on it. But part of me feels that it'll always be there a bit because of… my body.

Thoughts?

ps. I also feel that if I didn't have to answer to anyone, specifically people that know or have known me, I'd go for it. If my grand-parents, mother and family died, if I moved to an unknown town… I'd rather start anew as male rather than female. But being here hinders that feeling.

 

You seem quite independent from your family, even if you do still hold their opinions of you to heart. The question is, can you imagine yourself after the transition? Dating who you want to date and being who you want to be in a body that you chose, not one you seem to have been mistakenly given?

Do whatever you feel is right for you. Even if you haven't talked to your family about it, they probably won't be 100% surprised at whatever decision you make, from what you've said.