A Brief History

(Originally written August 7th, 2012)

On the eve of my birthday I am thinking about how it all started – my crossdressing, that is. I have a few very strong, very specific memories, and with them a smattering of more vague ones.

The most powerful, and important, in my opinion, dates back to I believe middle school, 8th grade, maybe 9th. I have trouble recalling those specifics. The A&E channel was showing a “reality” documentary about a group of people who volunteered to crossdress for a few weeks and live life as the other gender.

I remember seeing a commercial for this in the den with my family and immediately getting, and hiding an erection. I noted the time the show would be on, and kept it stored safely for later that night. When the time came, I went to bed early, and so nonchalantly that it had to have been suspicious.

At that time I had a small television in my room that fortunately got the cable channels. I can’t remember the name of the documentary, but I remember being so amazed that men and women could so convincingly pull of the other genders. The TV was at the foot of my bed, and I spent the entire night under the covers with an erection, clutching my penis in one hand, the television remote in the other – just in case a parent were to barge in.

The documentary was about two hours long – and would replay again late that night – around three of four in the morning. I couldn’t sleep, thinking about how much I wanted to watch it again – so I stayed up to do so. When I finally did fall asleep, I woke up in medias res of something new. My first nocturnal emission. I hastily cleaned myself up – nervous and confused about what had happened. I buried the tissues in the garbage and never told anyone.

To this day I can’t remember the name of the documentary, nor can I find any records of it on the internet.

I don’t remember if this was my first real experience with crossdressing. Something in me must have realized I was interested in this – or else I wouldn’t have watched it in secret. I don’t recall any examples of crossdressing early in my life – only a curiosity.

When I stopped taking baths and started showering, I, for some reason, always used my parents bedroom bathroom. I don’t know why this is – it’s something my siblings do as well, and I still do whenever I’m home. It’s a nice shower – that’s all I can think of. Regardless, in my parents bathroom, hanging on the inside door knob would always be my mother’s bra. I was always fascinated by bras – and over time I got more comfortable looking at them, feeling them, and eventually trying them on. Every night, before school or camp, I would go upstairs to take a shower, and quite frequently, before cleaning up, I would try on her bras.

I very clearly remember the way they looked and felt. Nylon and lace. Always white or off white. I admit – this is very, very strange, but it was apparently pretty formative, as I have such vivid memories.

Eventually, one day when my parents were both out of the house I snuck up to my parents’ bedroom and stole one my mom’s bras from her drawer. At night I would put it on, stuff it with socks and fondle my erection – never masturbating (more on that later, I suppose.)

I hid the bra behind my bed, which was pushed up against the wall and not often explored. Over time, my exploits became more intricate. First I created breasts using socks and hamster feed. Then I started making dresses by wrapping blankets around myself. I would lay in bed and just be comfortable.

One day my mom decided to use my closet to store some of my sick grandmother’s old clothes. Old lady dresses, but still women’s clothes. I had no problem wearing those. When my grandmother eventually died of cancer, her wig was stored in my garage. When no one was home, that too became part of my ensemble.

One night, the summer before ninth grade, I fell asleep with a bra on. I don’t know how it happened – I was always so careful not to get caught. Now, normally my mother would wake me up for work – this was my first summer with a job. On this morning, I woke myself up. I think. Immediately noticing the bra I took it off and hid it, along with the bird seed breast forms. Had my mom woke me up, noticed the bra, and left the room not wanting to embarrass me? I have no idea. To this day I don’t know if she knows.

I do know, though, that I had a red mark around my chest from the bra being too tight. I covered myself with a towel, went upstairs to shower and tried to scrub the marks away. No luck. Time would have to be the eraser – unfortunately I worked at a summer camp and we were going swimming that morning.

When swim came around the mark had mostly dissipated – but I was still nervous that some remnants had shown. I spent the rest of the summer foolishly thinking that everyone was on to me. I doubt anyone knew.

Eventually I moved off storing the bra and sock breasts – deciding to always play it safe. I would still dress when I was safely the only one at home. I remember being able to fit into, and then outgrowing my mother’s wedding dress in early high school. I remember the way the dress she wore to my bar mitzvah had built in curves that made my body look realistically feminine. I would stand in front of the mirror and stare at myself – too excited to feel any shame, only knowing I had a secret to keep.

Once I tried on lipstick – but never again when I spent a full week paranoid that it hadn’t come off completely. Another time I shaved a slight 1x1inch patch on my leg – partially by accident, not realizing the sharpness of razors. Although this was high up, I took extra precaution for a few weeks until it grew back completely.

By the time I was 16 I had my first girlfriend and my urges to crossdress strongly subsided. I still maintained some interest – especially on the internet. From 16 to 22 I only dressed rarely – primarily due to lack of clothing, and personal relationships. It never left my mind completely though.

I will discuss my relationship with crossdressing on the internet  in another post – there is a lot more to say on that topic than would fit here.

In the meantime, tomorrow is my birthday and I am excited to see what clothes my girlfriend bought for me to wear. I’m so glad that she’s willing to participate in this “hobby.” Yesterday she said I looked cute in a girly t-shirt I got, which was the nicest thing she could have possibly said to me at the time. She then said my body looked convincingly female. It’s these types of small little complements that make me so happy that I told her.

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One comment on “A Brief History

  1. local custom says:

    Incredible points. Outstanding arguments. Keep up the amazing spirit.

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