I actually managed OK living as a guy, in terms of gender stereotypes and how others perceived me. In highschool, I presented myself as a pretty normal cisgender guy, and that's more or less how I was perceived by both my peers and classmates. However, I always knew deep down that being a guy wasn't my true gender identity.
I did the typical guy stuff. Me and my friends were into body building. I was muscular and vascular. My hair was often shaved or in a fade. I played football and baseball for several years (Dad pushed me into sports from a young age). All of my friends were cis males and most were homophobic. When I wasn't playing sports, I was smoking pot and getting into scraps with my friends. I was a masculine, popular guy who would bully people who were vulnerable.
Now, I fear of running into my old friends, or those guys who I once shitkicked in highschool. As high school progressed, things started unraveling for me. On weekends when my family was away I would wear my brother's girlfriends clothes, and walk around my house in heels. It felt so right. Once in a while I would cake and smudge my mothers makeup onto my face. Ever since I was 14 I had thoughts of wanting to be a woman but I couldn't act on them in terms of a full out transition. I didn't want to be perceived as queer. I liked living with the privilege of being perceived as a tough white cisgender heterosexual guy. Not only that, but everyone was so happy with me as a guy, I didn't even stop to think about my own happiness, living to only seem approval from the people whom I surround myself with.
When I graduated, things fell apart. All my friends started doing things with their lives. Working, going off to college, pursuing different interests. None of my friends were real friends anyways, we fought more often then we got along. I told my dad I wasn't going to play sports in the summer last year so I could take a post-graduation break and focus on myself. During that time I realized how depressing and pathetic my life was. I was living my whole life for other people without myself being happy. Not only that, but I knew my parents, the people who actually mattered, would probably support me.
Slowly, I prepared for my transition. Because I was already doubting my gender identity in secret for so long I had started to grow my hair out a few months before summer. I stopped going to the gym and started eating leaner. I lost 30 pounds. I went from being bulky to slender. Then I started learning. I went on this page and tried to learn everything I could about transitioning. I watched lots of transgender youtubers. I learned more about the community, through my counselor and psychiatrist and started battling all of the internalized trans and homophobia that stuck with me over the years. Even now those internalized phobias aren't completely resolved for me.
Then there was the fateful day when I came out. I went to my bank and withdrew the only 200 dollars I had in my account. I bought some jeans, 2 shirts, some floral sneakers from payless, some makeup, and a bra. Then when I came home, my mother asked me if I had gone shopping. After lying to myself and those around my for several years at the point, I gave up. I told my mom I was shopping for women's clothes. She burst into tears and gave me the best hug a child in need could ask for.
My dad found out shortly after, and much to my surprise, although he needed time to adjust he was supportive to the idea of me transitioning.
After the day with my mom, I went full time. It was hard at the beginning because I was tucking with tape and didn't have barely any clothes to wear. Not only that but my hair was pretty damn short.
Over months, things got better. I went to a clinic and put myself on the wait list for HRT. I learned what a gaff is. My parents helped buy me some clothes/makeup to start out with, and after my brithday /christmas my wardrobe and makeup kit has become diverse. Also I started dressing like a woman instead of a little girl like I did at the beginning of my transition. I constantly use the internet to expand my mind and become aware of other's unique lifestyles, experiences, and perspectives.
Now i'm at a joyous part of my transition. I started blockers on the 22nd of January and I couldn't be happier. For once in my life, I am happy with my identity and I am at peace with myself.
And by the way, I thought people liked me before, but I was wrong. People only respected me in High School because they were afraid of me. I was a goof. I still regret being a bully to this day. But people forgive and forget. After coming out on facebook, many boys/girls have actually supported me and are happy for me that I'm finally living as my genuine self.
The most important thing is though, Is that i'm happy with myself, and slowly but surely, i'm growing and becoming more comfortable in my own skin.
Sorry for posting a novel.