It was freshman year of high school and I was friends with a few girls and for Halloween, we all wanted to get together and do this little trick-or-treat night together. I had never gone out trick-or-treating on my own. They were all like, “oh my God you should dress up like a girl, you should fully dress up like a girl” and “yes do it. Do it! DO IT!” and I’m like “fine, I’ll do it.” 

Halloween Day: Preparation

In preparation for that night, I asked one of my friends to do my makeup. She brought her makeup to school and we literally sat on the bench during lunch and she did my makeup in the middle of the Courtyard at my high school. Then I just loaded up a bag full of the clothes I was going to wear that night and the wig and whatnot. I got like a $12 wig and this outfit though, you guys, kills me! I had some gloves from Hot Topic and my dress is actually a skirt from White House Black Market, I had borrowed it from my aunt. I was also wearing some women’s shoes too. I don’t think I have pictures of them, but they were also from my aunt. I borrowed the majority of my outfit from my aunt with a necklace and such. I totally slutted myself up, going all out. I looked… not good, but it was dark and people couldn’t see too much. 

Trick-Or-Treating

We went from house to house through two different neighborhoods. We all walked up to the house together and the three of them would say “Trick-or-Treat” and I’d be at the very end and in my deep “manly” voice say, “Trick-or-Treat” and “Thanks!” but it was funny, a lot of the reactions were like, “oh my God, best costume ever” and I got a lot of positive responses, not many negatives. I’m surprised to be honest because my friend lived at the moment in a more seclusive neighborhood and a lot of people here in Arizona are very religious and don’t like or support the LGBT community as a whole. I was already out as gay at that time.

How I felt getting dressed up

I want to go back a little bit to talk about getting all dressed up. I’d say it took probably 4 hours with putting on the nails, making sure the makeup looked good, doing the hair, putting on the clothes, making sure I felt confident enough, and of course getting down the walk because I had not really worn high heels before that. I wore high heels for the night which was a mistake. I tripped a few times and decided to take them off while we were still out, which was disgusting walking around the neighborhood barefoot. But we circled around the block to go grab my shoes because I was not feeling it, but we still wanted to be out. 

I looked like a hot mess back then. I had oil problems and acne. My friend who did my makeup literally just did like my eyes. I was at my friend’s house and I got all dressed up and I took some pictures in her bedroom cuz she was in the bathroom getting ready and so used her room. You know, I honestly didn’t know what to think about what I saw. I was scared and actually cried. I thought I looked pretty, nothing like supermodel status, but it was scary. I had never even thought about being feminine in any which way at that point. The thought of something different was kind of intriguing. I don’t know if you know this, but I grew up Mormon. My family was really pushing the Mormon beliefs. My grandparents on both sides are Mormon. My dad has now left the church and is now an accomplished tattoo artist, feel free to check him out on social media @JohnHansenTattoo. My mom is still Mormon, so that made me nervous especially later in life when I came out as transgender. When I went home I was still kind of dressed up. I think I changed back into my boy clothing before I went home, but I still had the face on and they asked “how did it go?” and all I said was “it was great, it was great” and I went to my room and didn’t talk to anyone the rest of the night. 

The importance of my first time cross-dressing

The reason why I bring up this story is to show people that I had never even thought about anything like being transgender and that was how it all started. I’m not kidding, within two weeks I was wearing eyeshadow and painting my nails every single day for school every single day. I have some pictures from the following Christmas. I dressed up full glam, well, full glam for back then. For the Christmas party with my family, all the pictures I had full out eye shadow, I loved the eyeshadow. Dressing-up was honestly one of the most important parts of my transition and really helped shape me into the person I am today. If it wasn’t for my friends pushing me to do it, I feel like I would have never felt like I had finally found myself. That’s really the most important part, for you to love who you are. I’m glad for myself that I had realized this, because who knows if it could have been another 10 years before I finally realized this is why I’m not happy with myself. Thanks to those friends freshman year, I realized I did not like looking like a boy, it just didn’t suit me, personality-wise, and everything else. I just thought I looked awful all the time. The second I put on that “dress,” all I knew was that I liked how I looked. 

Thank you for taking the time to learn about my experience with crossdressing for the first time! I definitely think that it’s important for us to communicate with each other, so go ahead and continue to follow my journey on social media and share with me your own stories of discovering a new part of yourself and finding ways to love who you are!