When I was around the age of puberty, I occasionally hung out with the girl next door. Being in the country, that was a short walk from our house. She was a year or two younger than me. Considering that I only hung out with the guys one house over from hers on a nearly constant basis playing football, baseball, etc., I found myself confused at my interest in my new friend.
Well, sure, there were hormones going (I’m not gay), and she was kind of cute, but I wasn’t really “attracted” to her, per se. To be honest, her family was a bit quirky. She was not an exception.
But one day, I saw her in a dress.
She was just playing outside, running around, doing whatever all in a dress. No special occasion going on that day, she just decided to wear a dress. Back in those days, girls didn’t wear a dress except on those special holidays, or maybe to church. She was out in her yard, in a dress just because she wanted to wear one on that particular day.
I normally would cut through their front yard (the parents were fine with that) on my way to “the guys” house, and I stopped to chat. I didn’t make it to the guys’ house for a while.
As we played in the yard, she brought up the fact that she loved to wear dresses. This one was a bit over-sized, hem below her knees, and a flouncy A-line. I loved watching it move as she walked and played and danced. I can still see it (I’m sure the details have been edited by a faulty memory), a broad yellow floral cotton dress, puffy shoulders, and a high waist.
I felt something flutter in my chest as I watched. I didn’t know what that was. I felt guilty for feeling it. I assumed it was because I was lusting. But I didn’t know at the time that I was lusting as much (or more) for the dress as for the girl. I felt guilty. Like I shouldn’t be watching so closely.
I don’t know why, but she brought up the dress, and how much she loved dresses. “I would wear them all the time if I could,” she said. “My Mom gives me dresses, and I wear them around the house when I can.”
In looking back, I can see that I was putting myself in her shoes. Without understanding or even knowing that envy was the dominate feeling that caused the “flutter” from me unconsciously putting myself in that dress. I felt empowered by her revelation and confession that a dress was a feeling that girls enjoyed! It wasn’t just a social convention that women cowtowed to. There was a special girl feeling that came with wearing a dress and it was unique and delicious. As I contemplated that feeling, I was both electrified and mortified by my reaction. I felt confused on the inside with my feelings about how I would feel wearing that dress of hers!
But all the same, I thought about how that dress would feel on me. I thought about wearing only soft little panties under the dress. I imagined my legs naked and smooth down to the ground, moving in freedom under the dress, and the cloth caressing my skin. I saw her move freely, legs together or stretched out to either side while covered in soft fabric in a tent of privacy and femininity.
I can look back, now, and see how I was experiencing those moments. I can see that confusion about my feelings about the dress conflicting with my male persona (persona is Greek for “mask”) that was not allowed to consider these thoughts.
I can see now that the confusion was also fueled by the time when I was 8 at Halloween and my sisters dressed me as a little girl and one of the people at a Trick or Treat house asked me, “And what are you supposed to be, little girl?” And his face dropped when his friend nudged him with a look, and he figured it out, and the room went silent.
I wanted that dress. I wanted to wear that dress. But I was confused and ashamed. I was afraid that if I continued to hang out with her that I would ask her if I could wear one of her dresses. I’m guessing she would have said yes, and I would frolic in the yard in a dress and panties, and then all “the guys” would find out, and that would be hell.
I didn’t ask. And because of my confusion and my fear that I would act on my urge – I stopped hanging out with her.
Sitting here, now, in my dress, a simple frock that reminds me of that yellow dress, I am encouraged by that early moment in my life that affirms the truth of who I am today. Whether I am transgender, gender non-conforming, or gender fluid, I have always been Lorie. And today she is freer than she has ever been before. She continues to be that little girl in the dress playing in the yard, carefree and happy.
Girls, can you share with us a time you had an encounter with a girl back when you were a young boy that gave you the desire of wanting to wear a dress?
Or tell me about the very first time you got the desire to wear female clothing if it happened when you were a young boy.
Thanks for reading my story and I look so forward to hearing your responses to my article!
Tags: confused crossdresser cross dress when young crossdress as a school girl