Teenage Crossdressing Stories
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Teenage Crossdressing Stories
Crossdressing — Going out in public for the first time.
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There are many ‘first times’ when we crossdress. One of the most challenging is the first time we go out in public. Like so many things, this is best approached with a good plan, and in as controlled a situation as possible.
I am going to describe this as it worked best for me, and of course there is no particular right or wrong way to manage it. There are probably as…
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First, I'll have you know that I was NOT a very stylish teen. I wore the same oversized grey hoodie and baggy jeans most of my senior year, paired with a ponytail and no makeup, along with shoes that I think actually turned out to be from the men's department. I care a lot more about fashion now, which is why I can probably sometimes be a little too quick to judge when it comes to my teenage sister's outfits.
Kristen is 16 years old and pretty much your typical teenage girl: She loves to read YA series like Divergent and The Hunger Games , she's obsessed with Marvel (especially when it comes to Spider-Man), and although her school has a strict dress code involving uniforms, she usually sticks to the average teen uniform of leggings and hoodies at home.
I was curious to see what would happen if I gave her complete access to my wardrobe and asked her to dress me for a week. Would she put me in leggings every day or dress me up in all the cute dresses that I own but almost never wear? Let's find out!
First of all, this is the sort of thing that I usually wear:
I work from home and prefer to stick to neutrals and comfortable-but-stylish basics. Black skinny jeans and a black jacket (or down coat, when it's cold out) are my mainstays, along with ankle boots and a giant scarf. I have to admit, however, that some days when I have a lot of work and don't even leave the house, I just stay in pajamas.
I told Kristen at the beginning that the only rule was to approach the experiment seriously, mainly because she said she was tempted to just make me look like a complete fool and embarrass myself. I explained that I was honestly curious to see how she would dress me, so she agreed not to treat it like a joke.
For the first day (a Monday), Kristen picked out thick black leggings, a blue long-sleeved t-shirt and a grey hoodie layered under a black leather jacket, and my Comme de Garcons Play Converse sneakers, which I love but don't wear often enough.
I really liked this outfit. It was comfortable and casual (so casual that I was relieved I don't work in an office), and I thought she did a great job with the layering. I did wish she had picked my down coat instead of this jacket because it was cold out, but I was still reasonably warm.
Also, I have to note that I looked over at Kristen at one point later that day and realized she was dressed almost exactly the same: black leggings with a hoodie and a black jacket.
For the second day, Kristen dressed me in boyfriend jeans, a white sweater that my mom just gave me for Christmas, ballet flats, and a pink blanket scarf. (No coat because I don't think I left the house.)
This was another comfortable outfit, and even though it was still casual, I liked that it had a softer, more feminine color scheme. The scarf and sweater kept me warm on top, but the ripped jeans and ballet flats without socks left my bottom half on the chilly side.
On day #3, I told Kristen I had to shoot a video, with the hopes that she would pick out something really cute. She chose black leggings again, a striped crop top, a black jacket, and black knee-high boots with heels.
This outfit made me complain all day. First of all, these are the same leggings from day #1 and they were covered in dog hair, since I hadn't washed them yet. Secondly, I would never pair a crop top like this with low-waisted leggings. I'm not generally comfortable wearing crop tops, so I only wear them with high waisted bottoms to avoid having my stomach showing. Finally, suede high heel boots when it's wet and muddy out? Great.
I was not warm or comfortable at all in this outfit. This is also when I started to realize that teens apparently don't care much about dressing for the weather.
Day 4 was New Year's Eve. I had plans to go to a party and then stay overnight at a hotel. I already had my party dress picked out, but Kristen chose my outfit for driving to the hotel (as well as an outfit for driving home the next day). She chose a striped, knee-length T-shirt dress, my new yellow coat, a floppy black hat, black leather gloves, and black T-strap flats. The flats were a compromise because she wanted me to wear black heels, which I refused to do while driving for two hours.
I didn't love this outfit. It was colorful and put-together, but all these pieces combined didn't feel like my style. Also she didn't pick out tights, so my legs and feet were cold.
I packed the outfit that she picked out for day 5 and wore it for checking out of the hotel, having brunch at a diner, and driving home. This outfit was comprised of the same black flats, a red pencil skirt, a short sleeved velvet turtleneck, and (hallelujah!) black tights. I also wore the yellow coat again.
I liked this outfit, although to be honest, after a night of partying I would have vastly preferred to be wearing sweatpants and hoodies like all the hungover college students in the diner that I stopped at. Also, I realized that this skirt (which I haven't worn in ages) is now too tight and can't be zipped up all the way. So thanks for leading me to that realization, little sis.
At this point, Kristen was obviously getting tired of picking out my outfits. She chose the same boyfriend jeans from day #2, along with a gray T-shirt, a cardigan (only because I complained about being cold), and black ankle boots. She also finally let me wear my down coat, since I had to make a trip to the library.
This outfit was a lot more casual than the previous two, but I was OK with that since I was just happy to be warm and comfy at this point.
By the final day, we were both feeling pretty over this experiment. She was tired of having an extra chore in the morning, and I wanted the freedom to choose my own clothes back. She quickly picked out black skinny jeans (because I told her there was no way I was wearing the same black leggings for a third time), flat knee-high boots, a blue and white striped turtleneck (who knew teenagers were so into turtlenecks?), and my Union Jack cardigan.
She also let me wear my down coat again, since I was taking my dog to the dog park that day. I was warm and comfortable again, and we were both happy to be done with the experiment.
To be honest, it started out well but went downhill fast. At first we were both excited, but in the end I was tired of being cold in outfits that bared my midriff or legs and she was tired of hearing me complain about her choices. Turns out, it was hard to surrender control of my closet, especially this time of year. It could have been much worse — she could have put me in high heels and crop tops every day — but it's not fun having to ask a 16 year old for permission to wear a sweater.
Still, when I think about my complete lack of style when I was her age, I have to give Kristen props. She did a nice job with layering, proportions, and mixing different colors and patterns. She could have just had me wear leggings and a hoodie all week but she didn't. Perhaps high schoolers are more excited to appear put together than we give them credit for.
Now I'm wondering what it would be like if I had my teenage brother dress me for a week...
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People were saying that I was "disgusting and should die" or that I "deserved all of this."
Halloween my freshman year in high school was the scariest day of my life. But it wasn't scary because of a ghost or a monster — it was scary because in one moment, my life turned upside down.
Just a year before, I moved from New York to California. While in New York, I had been relentlessly bullied. And when I moved to California and started a new life, it seemed like a giant Band-Aid had "fixed" the problem. I had new friends, I started acting in plays and writing stories, and the bullying had stopped.
Halloween that year started like every other Halloween. I dressed up, had a great day at school, ate way too much candy, and laughed with some friends. But then it all changed.
I got a text message from a classmate I had known in New York. The text included a photo of a girl I didn't know wearing a big sign around her neck. The sign had my name on it: Aija Mayrock. I was so confused. Who was this person? I went on Facebook and saw dozens of people posting the same picture. A girl whom I'd never met dressed up as "me" for Halloween.
I was in a state of shock. In that moment, I did not feel sad or hopeless or angry. I felt like I was drowning and no one was there to save me. I scavenged through Facebook to see why this was happening, who did it, and for what reason. As I combed for information, I began to read the most disgusting comments about myself. People were saying that I was "disgusting and should die" or that I "deserved all of this."
I messaged the girl who dressed up as me. Let's call her "Sara." I wrote, "I don't know who you are or why you are doing this, but why would you dress up as me for Halloween?"
But instead of apologizing or even ignoring me, she posted an image of my note to her on Facebook, which only garnered even MORE attention and even MORE brutal comments. Each post hit my heart like a dagger.
As this was unfolding, I was standing with my school friends. I showed them the pictures, the disgusting comments, and the text messages. Just when I thought it couldn't get worse, my "friends" laughed at me and walked away. How could they think this was funny? How could they not see how hurt I was?
In a matter of minutes, I had been impersonated and humiliated 3,000 miles away by a girl I didn't even know, my new "friends" had shown their true colors, and the Band-Aid had been ripped off my new life in California.
I have never been so afraid of the world. I have never felt so alone, so hated, and so lost. That day I went home and told my mom everything. We found Sara's home number and spoke to her mom. When Sara got on the phone and apologized, I finally felt a wave of relief.
But a few days later, Sara sent me more harassing messages. And then I started to get anonymous phone calls where people said horrible things to me.
I immediately deleted all of my social media accounts and changed my phone number. But it was the most difficult time of my life. I really believed that there was something very wrong with me. Even though I lived across the country, I felt ashamed of myself. I started to wear baggy clothes to hide my body. I picked at my food, thinking my weight was my problem. And I started to avoid people. Maybe if I was invisible, no one would be mean to me?
A few weeks later, I entered a screenwriting competition in a film festival. I needed to find something to pour my pain into. I never thought I would be accepted into that competition. But, miraculously, I was. And I decided to write a screenplay about bullying.
That year, I won the competition. From that moment forward, I decided that I would dedicate my life to giving a voice to the voiceless through art. And that's when I started writing my book, The Survival Guide to Bullying.
It's not easy for me to share my story with the world. As I write this, I still feel that fear in the pit of my stomach. But I also feel a duty to share this story for you and every other person being bullied. You are NOT ALONE. There is NOTHING WRONG WITH YOU. I know this, because I have felt that way for too many years. Bullying won't last forever and you don't need to go through this alone. Without my parents' support, I never would have gotten through this.
And always remember this: In those moments when you feel that there is no hope, remember that I have had those moments, too. And so has every other person who has been bullied. But we have the power to move past our difficulties. We have the ability to change our lives. I have done it and I know that you can, too.
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