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Like most trans women, I remember the first time I ever wore female clothing knowing that it wasn't made or designed for me and that I really should not be wearing it.
It was back when I was either 10 or 11 and being a 'latch key kid' there were a few hours between my coming home after school and my parents arriving home from work. I don't know what possessed me to look through my mothers' clothes. ... Maybe she had some laundry out on her bed or in their bedroom or something and I felt myself growing … 'curious' … so I grabbed a dress, bra and pantyhose that were laying on the bed or in the clothes hamper or someplace else in plain site and proceeded to the bathroom to try them on. Even though nobody was home I went to the bathroom just in case someone arrived home earlier than expected.
Once I was in the bathroom I stripped down to my fruit-of-the-loom "tighty-whities" and proceeded to put on the pantyhose. I had seen my mother and sisters put on pantyhose before so I had a decent idea of how to do it. I may have even seen it done in a movie or TV show too, I don't really remember exactly where I learned it, but none-the-less I felt confident in my knowledge of how to successfully put on pantyhose. Using my hands & fingers, I scrunched and gathered them leg-by-leg down to the foot of the hose and placed it over my toes & heel then slowly pulled them up each leg, alternating every few inches between my left and right legs, being as careful as possible not to put any runs or tears in them. I had seen my mother "pitch-a-fit" when she got a run, so I knew I had to be extra careful not to damage the hose. Once the pantyhose were on and up around my waste, I took a moment to enjoy the feeling of having my lower half encased in nylon. It was a different feeling. Not weird. Not shameful. Not even embarrassing. The simplest way I can describe it is ... a feeling of "sexiness" embraced me. You may be asking yourself, "Sexiness at 10 or 11 years old?!?" ... Yes. That is what I felt. I may not have known it at the time, but in hindsight, yes ... definitely sexiness.
Now that I had the hose properly in place on my lower half, I moved onto the bra. Not really knowing anything about how to put on a bra or adjust it or anything, I did the old "put it on backwards, spin it around, and then stick your arms through" move. I was smart enough to not make any adjustments to it because my mom would then wonder why her bra didn't fit. Lucky for me I guess we were about the same-ish size because it seemed to fit fairly well from what I remember. (I'm using the definition of 'fairly well' from a 10 year olds point of view who had no clue about what he was doing at the time) As I looked at myself in the bathroom mirror, it was the first time I realized that I needed boobs. ... Real ones? ... Maybe, but I don't specifically remember. What I knew I needed at that moment was something to take the place of boobs and in my 10 year old mind the first thing I could think of was ... balloons. In my head I ran through a quick inventory of what was available around the house and I quickly realized that we didn't have any balloons so I moved on to the next idea ... socks.
My room was right next to the bathroom, so I thought about quickly running to my room, grabbing socks and returning to the bathroom. The time on my watch confirmed that I had at lease another 30 minutes of time before anyone was due to return home so I took the risk and ran to my room and back again with a pair of socks. It may have only taken a few seconds but to me it felt like ten minutes. Returning to the bathroom I started rolling and balling each of the socks up as best I could and made some make-shift boobs that would work for the moment, meanwhile filing the thought away in my head that I needed to get some balloons the next time I was at a store.
Now it was time to put on the dress. It wasn't any special dress. If I remember correctly it was made of cotton or a cotton blend and was a simple mid-length black dress with some sort of floral design embroidered along the chest and hem. It was a scoop or V-neck with short-ish sleeves. It must have been made sometime between 1977 and 1981 because I remember seeing my mom wear it in the recent past. It seemed to fit me fairly well. It's a memory that is slightly spotted after thirty years, but the one thing I do remember was looking at myself in the mirror and instead of feeling shame or guilt or humility I felt comfort and correctness. It was then that I realized I was running short of time to be able to remove and return everything to its original place ... OR ... I could keep these three items hidden in my room and in the next day or two go to the store to pick up balloons and try this all over again with better boob making material other than balled up gym socks. It was a big dilemma and I didn't have much time to ponder it. So I took the risk and returned to my room to disrobe, hide the clothes and redress in the attire I was wearing that day. Once all of this had been completed and except for the blatant fact that my mother was missing three articles of clothing, no one but me would know what happened during the previous 20 minutes or so.
Within the next couple of days I went to our local 7/11 convince store and purchased some balloons. Nothing fancy, just a small bag of simple party balloons. The day after my excursion to 7/11 when nobody was home, I experimented with the balloons both with water and without. I didn't do too much with the water filled balloons because I knew how easy it would be for them to break. In fact, when I did place them in the bra, I was always standing in the tub just in case they accidentally burst. That way I wouldn't have a potentially huge mess to clean up and explain. After about a week of experimenting with the three articles of clothing and balloons, I returned them back to my mother's room. I don't know if she ever knew I borrowed them or not. She never asked. Even during the week they went missing she never looked around for them (thinking she left them in the laundry room or something) and she never asked me if I had seen them. Nothing. To this day I find it strange that she didn't go looking for her missing clothes especially a bra, but she may have assumed one of my sisters borrowed the articles.
Now that I had the hose properly in place on my lower half, I moved onto the bra. Not really knowing anything about how to put on a bra or adjust it or anything, I did the old "put it on backwards, spin it around, and then stick your arms through" move. I was smart enough to not make any adjustments to it because my mom would then wonder why her bra didn't fit. Lucky for me I guess we were about the same-ish size because it seemed to fit fairly well from what I remember. (I'm using the definition of 'fairly well' from a 10 year olds point of view who had no clue about what he was doing at the time) As I looked at myself in the bathroom mirror, it was the first time I realized that I needed boobs. ... Real ones? ... Maybe, but I don't specifically remember. What I knew I needed at that moment was something to take the place of boobs and in my 10 year old mind the first thing I could think of was ... balloons. In my head I ran through a quick inventory of what was available around the house and I quickly realized that we didn't have any balloons so I moved on to the next idea ... socks.
My room was right next to the bathroom, so I thought about quickly running to my room, grabbing socks and returning to the bathroom. The time on my watch confirmed that I had at lease another 30 minutes of time before anyone was due to return home so I took the risk and ran to my room and back again with a pair of socks. It may have only taken a few seconds but to me it felt like ten minutes. Returning to the bathroom I started rolling and balling each of the socks up as best I could and made some make-shift boobs that would work for the moment, meanwhile filing the thought away in my head that I needed to get some balloons the next time I was at a store.
Now it was time to put on the dress. It wasn't any special dress. If I remember correctly it was made of cotton or a cotton blend and was a simple mid-length black dress with some sort of floral design embroidered along the chest and hem. It was a scoop or V-neck with short-ish sleeves. It must have been made sometime between 1977 and 1981 because I remember seeing my mom wear it in the recent past. It seemed to fit me fairly well. It's a memory that is slightly spotted after thirty years, but the one thing I do remember was looking at myself in the mirror and instead of feeling shame or guilt or humility I felt comfort and correctness. It was then that I realized I was running short of time to be able to remove and return everything to its original place ... OR ... I could keep these three items hidden in my room and in the next day or two go to the store to pick up balloons and try this all over again with better boob making material other than balled up gym socks. It was a big dilemma and I didn't have much time to ponder it. So I took the risk and returned to my room to disrobe, hide the clothes and redress in the attire I was wearing that day. Once all of this had been completed and except for the blatant fact that my mother was missing three articles of clothing, no one but me would know what happened during the previous 20 minutes or so.
Within the next couple of days I went to our local 7/11 convince store and purchased some balloons. Nothing fancy, just a small bag of simple party balloons. The day after my excursion to 7/11 when nobody was home, I experimented with the balloons both with water and without. I didn't do too much with the water filled balloons because I knew how easy it would be for them to break. In fact, when I did place them in the bra, I was always standing in the tub just in case they accidentally burst. That way I wouldn't have a potentially huge mess to clean up and explain. After about a week of experimenting with the three articles of clothing and balloons, I returned them back to my mother's room. I don't know if she ever knew I borrowed them or not. She never asked. Even during the week they went missing she never looked around for them (thinking she left them in the laundry room or something) and she never asked me if I had seen them. Nothing. To this day I find it strange that she didn't go looking for her missing clothes especially a bra, but she may have assumed one of my sisters borrowed the articles.
The thing I remember most about this time in my life was knowing that I wanted boobs which didn't make sense to me. A "boy with boobs" was not a normal thing. It was at this moment when I started feeling shame, guilt and humility for feeling different then the rest of society. Something I'd eventually come to terms with but it would take me 20+ years to get there.
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