How I Got Started

[Elaina]

Hi,

I am new to the forum and I have never shared my crossdressing experience with anyone. I am here to try to engage in meaningful conversations with other people and offer my acceptance and support to them, while also allowing myself to be accepted and supported by them. I thought that I might start by telling my story. So, here it goes:

My earliest memories are of my desire to be female. When I was about two I noticed that my mother wore pretty, silky slips/nightgowns when she put me to bed. I liked how soft they were, and enjoyed touching them. I would ask to keep her slips with me through the night, so that I could touch them with my hands and rub their silky material on my face. Sometimes it took some whining and convincing, and other times not so much...she always gave them to me and went to bed without them. At that time I didn't wear them, I just enjoyed laying with them and holding them against my skin.

I also spent plenty of time watching my mother putting on her makeup in the morning. She wanted me near her so that she could see me, so I sat on the floor and watched her routine every day. I liked how pretty she looked, and I wanted to be pretty too.

I started dressing before I went to kindergarten. I had a friend who I would visit for play dates, and he had a sister who was a few years older than us. One day, while she was sleeping, he showed me that he liked to go into her room and put on her underwear. I went in with him, and I too, put them on. Immediately, I knew that my life was forever changed. As soon as I felt the white cotton panties with red and purple hearts grace my thighs, I knew that I was meant to be a woman. I felt sexy, powerful, and RIGHT. My friend seemed to like the taboo part of dressing, but I felt like my soul had become aligned with God.

He was jumping around like a loon, and so after a moment, he turned around to see that I had already pulled on a white, lacy dress and was putting my feet into a pair of black flats with pink bows on the top. He didn't know that before I put the dress on, I had pushed my genitals between my legs and pulled the panties up more snug to hide my masculine features.

My friend and I dressed a few more times in his sister's clothing, but he eventually began to stop doing it, and tried to get me to stop, as well. I was confused. How could he want to stop feeling like this? How could he not realize how right this was? He started to tease me each time that I would try to convince him that we should play dress up, telling me that boys aren't supposed to do that sort of thing. He told me he had only done it because he liked the idea of being caught. I told him that I wanted to be a girl. I realized then, that I was different from him, and that I wouldn't be able to dress up with him anymore.

So, I started to sneak into my parents room and wear my mother's clothes. Nothing fit, of course, but that didn't stop me. I would often take the clothes that she threw away or stuck in a donation bag and I would hide them under my bed to wear later. My mother caught me several times, and there would be an argument between us, but she always let me keep whatever article of clothing I had taken. She would always ask me why I wanted it, and I always fell short of admitting that I wanted to be a girl, so I would just say "Because I want it."

Once, I found a pair of black nylon stockings in the trash, because it had a hole in it. I immediately slipped them on and walked around the house with them. Mom just shook her head and shrugged, but my father told me to take them off. I did, but I put them back on the next day. He saw me with them again, and he went and spoke to my mother, who came to me with tears in her eyes and told me to take them off. I gave them to her, and she threw them away.

I knew that my crossdressing would not be accepted, then. For years I continued to wear her clothes, and I would often wear her undergarments under my own clothes and hope that I would get caught. I can't begin to tell you how many times I wore her bra under my shirt, hoping that the whole family would notice, and find out what I was doing. I wanted to get caught so that they would understand who I really was. I wanted to get caught over and over, so that they would finally let me wear girl's clothing all the time. At one point, I even asked my mother if I could wear girl's clothing to school, and she said "No."

At about age nine, I was at my neighbor's house visiting. They had a daughter who was a year older than I, and she was painting her nails. On a whim, she asked if she could paint mine. I had learned by now that I was not to show any sort of interest in anything girly, so I feigned disinterest. I allowed her to persuade me though, and soon I had beautiful pink nails. Her mother was there, and they both giggled as the polish was applied, and laughed with surprise when I kicked off my shoes and asked if they would do my toenails too.

This happened on multiple occasions. I would go over and visit, and I would get my nails painted in all sorts of colors and swirls. One day, her father came home and saw what was happening. He just shook his head and said, "I don't know about you boy." That became a regular occurrence. When I would get home, my mother would shake her head and remove the nail polish. Eventually, she stopped letting me go over to the neighbor's house.

When I was eleven I had a friend over and we were watching television. It was "Jerry Springer", and they were doing an episode in which audience members had to guess as to which of the show's guests were women and which were men (they were trans women). I told my friend they all had to be women, because they all looked so realistic. We discovered that some of them were trans, and I didn't understand how that was possible. They were in swimsuits and skimpy clothing, but their male parts were not visible. They also had breasts! That was when my friend told me about vaginoplasty and breast implants. I had no idea of what that was, but I was floored. "You mean, they can actually DO that?"

Instantly, I hoped that I could have a vaginoplasty and breast implants. I so desperately wanted to be a woman. After I picked my jaw up from the floor, I asked him if they could make it so that the trans women could have babies. He said, "No." I was slightly disappointed, but I hoped beyond hope that I could one day become female.

It was also at this time that I started to have sexual thoughts about the boys that I knew. I was interested in the girls too, but I was interested in the boys as well. I daydreamed about getting married to them (I had a beautiful white gown, of course, and long, flowing, brown hair, with just a touch of blush and mascara to accentuate my already gorgeous feminine features), and I dreamed of a domestic life with them. I was raised with a traditional view of women's roles, so I saw myself being the wife who took care of domestic duties and still made time for her man. I became obsessed with the idea of, naming our children, and raising them.

There are plenty of things I could say about how crossdressing works in my life now, but that is for another post. I thought that posting about my beginnings would be a great way to finally start to share my story. I apologize for it being long, and I hope that it was not boring. I welcome your thoughts, comments, and questions. I really would like to be able to engage with others about these sorts of issues.

Elaina