Why “crossdressing” is such a big part of my transgender experience

Every transgender journey is a little different. Some of us know at an early age there’s something unique about us. Others feel a nagging sensation they can’t explain inside somewhere that manifests fully later in life. Some, especially transmen, go through the steps of accepting they are gay or lesbian first before coming all the way out. This is my story. How I went from being a girl in my daydreams to living as a woman in real life. 

The earliest memory I have of what could be considered crossdressing, which I will use here to mean wearing typically feminine attire while I was assigned male at birth and living as a boy. It was Halloween. I was no more than 6 or 7 years old maybe younger. My sisters Stacy, Candy and myself all dressed as “punk rockers” one year. I was able to wear daggly plastic jewelry as a part of the costume and wear face paint. I was so giddy walking around with my unkempt hair dressed like a rock star, back then they looked kinda feminine anyways, people kept thinking I was  a girl. I didn’t mind although I pretended it bothered me because I knew I had to behave a certain way. Deep own though I liked it.

Sadly it would be several years before I got my next dose of the drug that would consume me. This time I was in 3rd grade. I had just finished watching the movie Weird Science with a cousin of mine. We were dorks so playing along with the movie I set up my toys to look like a computer and we put bras on our heads. Dad came in and yanked the bra off my head asked if I was a fag and told me to not play that game ever again. I overreacted because it was just a silly game but it still stirred something inside me touching a woman’s bra. It was kinda gross because it was either my moms or my sisters. Nonetheless it helped reawaken that feeling I had buried.

I can’t be certain the timeline but it was in the same house, 3rd grade. I remember that much because we moved a lot and I mark my memories based on which house we lived in. The details of a house are sometimes all the anchor I have to set my brain straight. 

I was a sleep. Dreaming about going to Blockbuster video to rent a movie. The reason I dreamt it was because we never went there. We were poor so we rented from the library or the book store that had 50 cent rentals. In the dream I rented a tape. It didn’t have a label I just grabbed it off the shelf and knew it was the right movie for me. I hugged it tightly, possessively. The details are fuzzy as dreams are but I vague remember going through a chase scene desperately trying to get home to open that box and see what film was inside. I knew it would change forever whatever it was. I got the box home crawled behind the couch where I was safe from prying eyes and opened it. Inside the box was not a VHS tape with a prized movie or some other treasure. In my subconscious I knew it was significant hence why I defended it so intensely. Inside the box was a pair of girls panties. They were pink. I put them on in the dream and suddenly I felt more alive than I have ever felt in my entire life. I woke up, in tears when I realized it was just a dream and those panties were not on my person. I never wore boy underwear another day in my life. That was the day I started going commando, against my mothers stern reminders to wear undies. I refused. They were the wrong undies and I couldn’t do it anymore. I was 8 years old and refused to wear boys underwear from that day forward.

The next time I dabbled was in the next house after we moved again. I was 10 now. Still haunted nightly by that dream. It kept nagging at me to steal a pair of my sisters panties and just try them out. Try them on. See how it felt. 

We were playing, my three sisters, my cousin who lived with us and a couple of their friends. It was a game of pretend. We were playing pirates. I was a Scottish pirate so I insisted my sister let me wear one of her skirts as my “kilt” for the game. Once I put it one all the girls giggled but I pushed forward with the ruse and the game ensued. It was over the top of my pants and thus didn’t quite fulfill the fantasy but I was getting closer.

The same house, later that summer shortly after my 11th birthday had passed I seized my opportunity. I was sitting on the recliner watching TV and mom was doing laundry. She plopped the laundry basket on the floor next to me. I looked down and say sitting on top a pair of white panties with a pink trim. They had some sort of flower pattern but I couldn’t tell you today which flower it was. I looked around, made sure nobody was watching me and grabbed them, shoved them up my shirt and waited. I also snatched a bra and a nightgown I knew would go unnoticed. I waiting till the show was back on and all eyes were glued towards the TV set. I slunk back into my bedroom, put them on and felt instant euphoria. I cried real tears. Nothing ever felt more real, more joyous than that moment. I rolled around my bed giggling I was a girl, I was a lesbian, I was a gay girl. I was giggling like I had never giggled before. Good thing the TV was loud or else they might have heard me. 

From there it was on. I never went to school, outside, or to bed without a pair of panties. Slowly but steadily I secretly built up my girlie wardrobe. By my 12th birthday, just one year later, I had amassed a full set. I had panties, bras, skirts, night gowns, slips, dresses, swimming suits, shorts, everything I could get my hands on. I had three sisters, two close to my age and size who each had girlfriends their own ages. Girls buy a lot of clothes. They swap a lot of clothes. They quite often lose articles of clothing and never think twice about it. This made my obtaining items quite easy. My stole from their girlfriends. I stole from my own girlfriends who let me into their bedrooms or wore things into mine. I even shoplifted from the thrift stores every chance I could. I didn’t care I felt justified because I desperately needed girl clothes. I hated wearing boy clothes. It made me sick. It made me disgusted with myself.

By the time I was 18 I was dressing up daily. If I was home alone I was in girl mode. I savored every trip my parents took out of town. The longer trips bought me more girl time. I would put on a dress, crank up the Britney Spears and do the dishes. I would dance around like fag I thought I was because I hadn’t learned what trans was.

Once I moved into my first apartment on my own without a roommate I went Stephanie full time. I came home from work, got boy clothes off, sometimes as I was walking into the door, got into girl mode and let out a deep sigh of relief. I did this every day for three years before finally coming out to the world during Pride month 2020. I have no regrets. Not the things I stole nor the girls I stole them from. I do not regret doing what I had to do to survive. What I had to do, to get to where I could love myself. To me it was life or death. 

Even now I refuse to wear pants. I refuse to wear a ballcap. Anything that resembles the clothes I had to wear in my boy disguise I despise, detest so much they make me gag just thinking about it. For me, I was always a little girl trapped in a boys body. Today, I am a proud transwoman conquering the world.

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Stephanie Bri

A transgender writer who also does podcasts and videos.