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Writer's pictureYoya Fabulosa

My first time crossdressing...



The first time I've ever dressed up in woman's clothing was in High School for Halloween. It was my senior year and I knew I wanted to dressed up like a woman! I worked with some of my girlfriends to find the perfect outfit. Luckily at lot of my friends were in theatre, so they offered to help me with my makeup and hair. One of them actually had a wig just laying around. I'll never forget what I wore my first time... I wore a red blazer and red mini skirt, I wanted to give boss vibe as I strut through the hallways in my 4 inch heels. My closest friend and I were the same shoot size and she had these legendary booties that I would always wear when I was first starting my crossdressing journey. I walked like a complete natural, despite it being my first time I believe I've been prepping for this moment my whole life. Seriously! When I was younger I use to walk around on the tips of my toes pretending I was wearing heels while imitating the clacking sounds I loved to hear whenever high heels made contact with the ground. So when I first wore those heels, I just imagined I was walking on the tips of my toes, and I was strutting like there was no tomorrow! My first time was an absolute blast! I had teachers who loved it and other students who treated me like the diva I knew I always way. But there was a bit of drama. I remember it was during sixth period lunch, when I walked through the cafeteria to grab my lunch and go to my art class (my senior year I didn't have a lunch break) and a group of rowdy boys felt so insecure that they had to go out of their way to harass me. The followed me to my art class room and called me profane names, but I kept matching cause I knew I was the moment. They didn't like being ignore! So of those insecure little boys spat on my skirt! I was so shocked, but before I had time to react-- My best friend at the time lunched herself at the guy, chasing him down the hallway. My art teacher witnessed this at the time and commented on how well composed I was during the whole incident. It didn't bother me at all, because I was riding this high-- Dressing in public for the first time created this impenetrable state of happiness. I was going to let some group of losers rain on my parade! It was such an amazing experience over all, so much so that I continued to dressed up multiple times while at school; because why not?! I actually have two different videos of me dressing up while attending college, you should check them out if you haven't already. ;) xoxo Yoya Fabulosa


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