Wondering what it would be like to be the opposite gender isn't an experience unique to tomboys or feminine boys; I think everyone thinks about this kind of thing at least once, and sometimes thinks about all the positives they could experience as the opposite sex — avoiding the expectations placed on their own sex. Men don't want to always be expected to be tough leaders, and women don't want to always be expected to be sensitive followers. Sometimes it can be hard to come to the conclusion that not conforming to stereotypes just means you're human.
I also think one would be hard-pressed to find a child who isn't afraid to grow up, to have an adult body — especially when the intermediary stages are so awkward. Having budding breasts that are too small, or too large, having "weird nipples," being too hairy, being too hairless... being perceived at all by others, period, is one of our greatest torments about being human. As Jean-Paul Sartre wrote, when we perceive ourselves being perceived, we objectify ourselves in the same way others objectify us.
This all being said, I am going to explain what happened to me - I am sure others will be able to relate.
Last year, I made one of the biggest changes in my life thus far by deciding to stop trying to live as the opposite sex. A few days after my 28th birthday would have been my ten year anniversary of cross-sex hormones. This was to be a milestone I always thought I would feel at peace with, so deep into my "authentic life." A month after that was 6 years after my mastectomy, something I stopped genuinely thinking about pretty much as soon as I recovered from the surgery.
I had what may be called a more severe case of gender dysphoria as a child, though none of it had anything to do with my body until I began learning about the ways others changed theirs. In the beginning, I simply thought so much would be better if I were a boy - my "tomboyish" hobbies would be accepted by boys, I wouldn't get stared at in the video game aisles... nevermind all the negatives that would come with being a boy, like being judged for my carebear collection or affinity for barbies! In truth, I was less of a "classic tomboy" and more of a healthy young girl who did not let gender stereotypes dictate her life.
And yet each night I prayed, and every year made birthday wishes, and every day hoped with all my might to one day wake up as a boy, with not a soul having any recollection to the contrary. And yet, I did not really mind being a girl. In fact, our neighbor loved to tease my sister and I by yelling to us, "Hey, boys!" which was met without fail each time: "WE'RE GIRLS, MARK!"
My main issue with sex was primarily that everyone around me seemed obsessed with separating boys and girls, telling us what hobbies or friends we were allowed to have, something I did not understand.
A hefty desktop computer found its way into my home as a child, complete with dial-up and MS Paint. When I first got online, I was about 10 years old (this was in 2006-07). At first I mostly played dress up games, arcade games, and things of that sort. Eventually I learned that I could search questions that I had and find answers, which led me to... Yahoo! Answers.
Yeah, if you were posting questions on Y!A in the aughts, chances are a barely-fifth grade girl was answering. I was often mistaken for a guy, because my birth name is traditionally masculine and was cut off to an even more masculine name due to the character limitation for screen names.
I wound up on the LGBT section of Y!A and asked if I could be "a boy inside" even if I loved my long hair, liked my girl clothes, liked my "girly hobbies," and didn't really mind being called a girl.
The answer was, bizarrely, a resounding "yes." Several of the responses even gave me resources: forums I had absolutely no business being on, full of transsexual adults. Webcomics that glamorized medicalization and the lives of these adults, and sometimes even teenagers.
