How Crossdressing Made Me a Man

I kept the wig in the car. Just in case. Sometimes they needed me. The jersey was always sitting on the sideline, empty, waiting for me to pick it up and shove it over my growing belly. I actually filled it out nicely. I wasn’t too husky yet, so the green and white stripe down the side was very slimming. My dad was coaching my oldest sister’s soccer team and their attendance was pretty poor. If little Becky had an orthodontist appointment or if Melody couldn’t find her safety goggles, the team usually didn’t have the required number of players to properly cover the field. That’s where I came in. “Matty” – the secret weapon of 14-year-old girl’s soccer. My dad would wave me over and hand me the jersey. That was the sign. I was going in. I begged my dad to let me wear the wig, but he had to put his foot down somewhere, I guess.

There actually was no wig, but the team did exist and I was actually really good – the best, even. The opposing girls had no problem letting a blossoming-into-huskiness-10 year old with asthma play against them. They thought they had me all figured out. They thought they could handle the little brother of number 9 – the cross-dressing son of the head coach. But they were wrong. I wiped the field with them. They were keeled over, sucking in air after 10 minutes. I was just warming up.

My sisters practically raised me. And by “practically” I mean that I had a stay-at-home mom and a great dad that played outside with me all the time and taught me to ride a bike and throw a football. But, I did spend a lot of time playing with my sisters too.

Let me paint you a picture of my then 14-year-old sister, Sarah:

She was the boss. She was in charge. She planned activities for my other sister and I, and we had to follow along, no questions asked. She was tall for her age, but after her growth spurt ended and everyone else caught up to her, she quickly became the shortest in the family. She had great style and command and loved to work. She pulled and tugged the lawn mower up and down our front yard effortlessly. That’s who she was. She was tough. I hated mowing the grass. I hated yard work. I hated work. I would have killed myself. I would have hanged myself from the porch with my NES cables. I would have doused myself in cooking sherry and stood too close to the vanilla cupcake Yankee candle. But she liked to do it. I think it made her feel strong. She was the ringleader and what she said, we did. And that meant being in every play that she wrote – in every runway show that she choreographed.

This next section might be a little hard to get through for all you fellow, raised-by-girls dudes out there. But we’re in this together. Keep the faith.

My sisters loved to dress me up in their clothes. I was their best girlfriend from next door or I was a supermodel walking down the runway or I was the lipstick-wielding corporate woman going on a job interview. I never understood lipstick. I still don’t. It looked like blood on my lips. They would smear it all over my face, too. If a stranger were to ring the doorbell and see me in my underwear and high heels, screaming and running towards them with this blood-red goo all over my face, I think they’d have a hard time not thinking that I just devoured the whole cast of Priscilla, Queen of the Dessert in that bathroom back there and that this might not be the best time to sell our family a new vacuum cleaner.

I had to participate. If I didn’t I wouldn’t have had anything to do. I would have had to read a book. And no one wants that.

My other sister, Rachel, was the middle child. She was compassionate and loving and patient – but only to her dolls. If I sat in her seat on the couch, game over. She had the best back-hand on the block. We played house a lot. I was the dog or the baby or the little sister. We would act out her crazy imagination with no regard to safety. One time we were “sled riding” down our indoor staircase in the middle of August. I was the “little sister” at the time, dressed up in girl’s outerwear. It was a quiet day if I remember correctly. She jumped on the back of the sled with me and down we went. Unfortunately for her, my chubby little butt landed right on her arm and crushed it faster than a beer can on a frat guy’s head. Her arm did heal, eventually, and we had to, sadly, wait until winter to get the sleds back out.

When their friends would come over, I would join in with them. I was constantly surrounded by girls. I knew how to relate to them. I knew how to understand their emotions. I knew when to talk and when to listen. They taught me how to relate to girls in a mature and intelligent way – guaranteeing me absolutely no girlfriends longer than a week and a half. They would get tired of me and move on to Dirk – the hot head skateboarder from down the street. I was as close to first base as a paraplegic with short-term memory loss who left his legs in his other car. Girls didn’t want to be respected then. They wanted to be with the bad boy. They wanted to be with the Stanley Kowalski’s of the world. I was passionate and understanding and boring. But my sisters had a plan. They knew that I would have my moment in the sun.

My sisters put me through many traumatic experiences. They even have pictures locked up in safes, waiting to show to my blushing bride on my wedding night – the perfect image to put in some lucky girl’s head as I carry her across the threshold. But, my sisters taught me so much. They taught me to be patient and not settle on the two-week relationships that surrounded my adolescence. They taught me to be unafraid and vulnerable and willing to put myself out there. They taught me to be an actor and a writer and a comedian and gave me plenty of great material. They taught me to respect women. They taught me to be my own man. They also did teach me to be a cross dresser at the tender age of 10, but I forgive them for that.

My sisters came up to NYC last week for Thanksgiving, and for the first time, I had things to teach them. I taught them to not count their money on the subway. I taught them which ticket machine didn’t smell like pee. I taught them how to properly fold their pizza so the grease dripped onto the plate and not their jeans. I felt like a big brother for the first time. So, without getting too sappy, I would like to give a shout-out to my sisters for dressing me up like a cracked-out, tranny Barbie. Thanks, Sarah and Rachel. You taught me a lot.