Ever since I was a kid I would play dress up with my sisters. As I was the only boy it was easy for me to find myself lured into the seductive world of the mysterious female creature. Not that I want to belittle women, on the contrary I am not only fascinated by femininity on a personal level, I have a deep respect for what females go through. Over the years there were a number of movies, TV shows, cartoons, toys and even video games that either inspired me or motivated me in some way as I explored the feminine form through cross dressing.
Below are a few of the different works that shaped my world.
Boy Meets World
It was season 3. Corey Mathews and Shawn Hunter were doing a class project to become a female in order to experience dating from the eyes of a girl. It was an eye-opening episode that stirred things not only in myself, but clearly in the writers as it really cemented the comedic running gag of the adoration the two friends had for one another.
It wasn’t the Girl Like Me episode that really tickled the girl hiding inside’s fancy. It was actually the later episode where Joey the Rat and Frankie the Enforcer dress the two boys in cheerleader outfits. By the time I discovered this episode I had already stolen my sisters discarded cheerleader uniform and claimed it as my own. Oh I wore that thing out with my secretive dance routines. Not for nothing but it was glorious for me to see my role models strutting their stuff on national TV in front of all my peers quietly reaffirming my own feminine desires. I experienced a similar incident when one of my male friends dressed like a girl to school for a class project and one of the boys in class commented how nice his ass looked in girl pants. I wasn’t in his grade, I was a couple years older but when he relayed the story to me I immediately mentioned our mutually favorite TGIF sitcom to which he smiled and got into the spirit of it.
Super Mario Bros. 2
This one is two fold. First it was the perfect opportunity for me to play a video game as a female character. It was a way to cross dress in plain sight, even if it was only virtually the case. Still playing the game as Princess Toadstool (peach) was such a revelation for me. I enjoyed it a little too much at times I must say. It quickly became one of my favorite video games of all time. It was easy for me to justify picking the princess too because she had that floating jump that made her useful as a character.
In later years I would learn to use video games to express my girly side more often. I had to be sneaky at times with some games but it started with me running around Subcon as the princess of the Mushroom Kingdom on a quest to return home.
All of that by itself was easily enough to stir things in me. However Nintendo Company Limited, or NCL, the Japanese parent of Nintendo of America, sneaked a nifty little cross dressing surprise in the game just for “girls” like me. Birdo is a pink bird enemy boss in the game that shoots eggs at the player. Fortunately in the official lore Birdo is actually a cross dresser pretending to be a girl bird but is really a guy bird. They never explain how he/she is able to shoot/lay eggs but that’s not too important, after all it is a fantasy game.
Being John Malkovich
I cried. I literally cried when I got to the end and heard the voice over of the adult male swimming in the pool inside the body of the young girl. I had long desired to not only look and act more like a girl but there was always this part of me that really wanted to have a female body, complete with all the stuff most girls complain about.
The movie itself is very weird. At first I was only passively into it out of morbid curiosity. However as the story progressed it captured my imagination and held my attention until the very end. To this day I feel a stirring whenever I think of this movie. In fact it was such a powerful feelings I’ve since decided to ration my viewings of the film in order to preserve some of that mystery. I would hate to watch it too much and wear it down.
If this movie didn’t make a list of a budding cross dresser as something to explore I’d say that person isn’t digging deep enough. A combination of heartfelt, awakening and a little on the creepy side, it has that perfect blend that makes you just uncomfortable enough with how comfortable it makes you feel about cross dressing, transgenderism and even homosexuality if you go that route. It was one of those movies that was hiding some subtext I picked up on quickly under that mask of a kids show. Don’t think that was lost on someone like me who enjoyed heavily seeking out forms of entertainment that either normalized, if not glamorized the ideas I was fostering.
This. This game was heavenly. The first time I realized I could create an imaginary world where I could live out my fantasy of being a woman entirely from childhood into adulthood was mesmerizing. Of course I was already a fan of sim type games, Sim City, Sim Earth, Sim Ant, etc., but to get to create a female character with her own hopes, dreams, personality and style and then set her on the path to success, OMG it was beyond heavenly, it was absolute ecstasy.
This one falls more under the category of exploring lesbianism as a potential lifestyle. Still, as someone who was fascinated with all aspects of femininity I couldn’t help but consider the need to also learn about the females who were sexually attracted to other females.
The movie is considered archaic today by the LGBT community for it’s stance on being gay being a choice which is not the common view point held by many in the community. Still, it was one of those movies that, at the time, did a lot for breaking down walls and getting people like me to ask the questions my parents were hoping I would avoid.
The movie itself doesn’t really do much for a cross dresser but it still helps normalize the alternative lifestyles as they call it which something.
The Secret World of Alex Mack
This one isn’t so much about cross dressing in particular but it was one of the earliest examples of a female super hero that really stuck with me. It was a teenage girl trying to live her normal life while being granted super powers. Of course the far superior and vastly more popular Buff the Vampire Slayer would soon replace it in the cultural lexicon but you have to give it props for being able to lure young boys into a watching a TV show where the main character is sort of an action hero and totally a chick.
Buffy the Vampire Slayer
I already mentioned it above but this show broke down barriers. It obviously left a mark on me. Now truth be told I already had a crush on the young Alyson Hannigan from her appearance in My Step-Mother is an Alien a few years prior. It was easy for me to get into this show as it featured her as one of the prominent characters throughout.
This show started off with the lesbian leaving Ross for another woman right off the bat. It also sported three equally interesting and very strong female leads who carried the weight of the show as much as, if not more than, their male counterparts.
Over the entire course of the show’s run I took flack for liking it so much from many of my male compatriots. It was called a show for chicks, a show for gays, or both. I didn’t care I replied, Rachel is hot so whatever. Hey, Rachel was hot so there is that. Nobody needed to know I was equally checking out the cute outfit she was rocking each week while also appreciating the rest of her beauty. There was also the episode with Ben playing with his Barbie. Obviously this stirred things up in me as well.
I know I’ve talked about this a lot but you know what, if my older sister hadn’t introduced me to the lovely world of this amazing super hero with her cast of colorful friends, who knows what I might have ended up liking. The toy and cartoon both had an impact on my interests in life early on. I especially liked the purple girl that wore glasses. She was my favorite.
There are many others, too many for an article such as this. Here are a few quickies to round out the spectrum.
G1 Transformers and Arcee, a female robot made by male robots to understand females.
Super Metroid for staring a bad-ass action hero that looked somewhat masculine to trick boys into playing but was totally a woman underneath it all.
Clueless, a teen comedy all about fashion and shopping. What’s not to like.
Herman’s Head. He had a chick living inside his head controlling his sensitive side.
And there you have it a brief list of movies, cartoons, video games and toys that either inspired or influenced the cross dresser in me. Stay Cool.