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I began crossdressing around the age of 10. That may sound scary to some people but there was something there that drew me to it inside myself. Please join me on this walk through my history with cross dressing and discovering my gender.
Content Warning: Sex and kink mentions, dysphoria
Before I get into this. A resource I've linked to before is Stained Glass Woman who has actually written an amazing article on Sex and Kink and how common it is in the transgender community as a form of safe expression and exploration before hand. I highly recommend reading this. I will just share my personal journey but if any of this even remotely resonates with you please read her piece: https://stainedglasswoman.substack.com/p/beneath-the-surface[0]
I first remember my affinity for presenting female was during dress-up games as a child. Wearing my moms high heels or a dress or wig playing about with my siblings and friends. While this is technically true I do not necessarily think there is much to read into here. I was simply being a kid. The first time I think I was what I would consider crossdressing when I was about 11 or so, a pre-teen. I found myself home alone and ventured into my mothers closet and walked in-front of their vanity. I just stood there. I didn't do anything. I simply stood there staring at myself. I did this a lot. Any time I could. While this was over 20 years ago now I distinctly remember thinking a few years later "why the hell did I do that" and even remembering thinking at the time "why am I doing this". I couldn't explain it. But I did. I continued to do this for a while. I don't remember why I stopped, probably because I was a teen and sex took over my brain and struggling with my sexuality was a bit easier to tackle. I continued, however, doing some other classic pre-trans signs like tucking and such.
As I got older and started going online I returned to her. At first I wasn't crossdressing but simply taking online personas. This would often fall under sex and kink stuff where I would find myself reading transformation or genderbending scenarios. When I turned 18 I would even go online and just sign-up as a woman and just assume that role.
I'd even join streams where I'd sign up female and in the chat get called she/her and such, even by the streamer we're chatting with (FWIW this is like 2009 era streaming) and I'd melt. Yeah, some serious egg_irl stuff. But this led me into more personal cross dressing.
My first adult experience with crossdressing was the first weekend at college. We were doing a new student scavenger hunt where one of the tasks was "change clothes with a teammate". My group all looks at each other like... uhhh... and didn't wanna volunteer. My friend says sure! And I'm like I'll do it. So she and I swapped our clothes. She was in jeans a top and a black leather jacket. I was probably in ill fitting jeans and an ill fitting shirt with a hoodie. So we swapped clothes in one of the dorm rooms. All we had to do was take a photo together for the competition. I kinda wish I had that photo still.
Funnily enough, my second moment was the next semester we were having some couples theme party and I was desperately single and my friend's girlfriend was at another school so he and I went together and of course I volunteered to wear the dress. I went over to that same friend as before's room and she and some friends gave me a makeover. I was in a modest black dress they did something to make my hair a bit less bad, and my make-up.
I think that was when things changed for me. If you asked me how I got here I couldn't tell you. That's what I find so interesting. I have no clue why (well now I know why). I found myself chatting with an online friend I made. I think we met on omegle or something and I talked about how those experiences and I don't know what was happening. She took interest and would talk to me about it a lot. She even encouraged me to buy some clothes online. So I did. Mostly little things that I could wear beneath my clothes (underwear and such) or something small. But I continued to do this for the rest of the school year. I would wear the underwear around outside and such. It made me feel really good. Due to my misunderstanding I mistook what was gender euphoria as fetishistic and had this guilty sinking feeling inside me. But I'll touch on that below in "How I realized this was more than just a fetish" .
I kept buying things with what little money I had. I kept using female personas. I'd even chat with men online as a cross dresser and this became a full fledged kink for me. It still never felt like a kink. It felt like I was just being me online. It felt really great, because of the gender euphoria, but whenever things would get too sexual I would end up getting anxious and stopping. This was the quandary that I was faced with:
Maybe not enjoy is the wrong word. More so, it doesn't feel right. I still felt like a boy, in women's clothes, turning people on because I was a boy in women's clothes. Not because I was a woman. I realize that more clearly now but that disconnect was really hurting me.
That said at this point I had a cute stash of outfits and a wig or two thanks to the ever more popular Amazon.com and free shipping. I had been working over the summers too so I had plenty of allowance for buying things. I wasn't doing anything seriously but it was a great outlet for myself.
What frustrates me is I never encountered another trans person (or out trans person) during all of this. I did, towards the end of this journey, discover the trans subreddits, but this lingering fear in the back of my mind clouded the words and made me run away from it.
Because this never went beyond the fetish range when it was time to pack my dorm and go home. Every year I'd take the drawer I stashed my clothes in and dump it into a black trash bag while my roommates were out. I'd cry that night. Knowing I'm just going to have to start over again next year. But the thought of my parents finding a bag of women's clothes and sex toys made me so scared.
Except my senior year. It's time to stop all this perversion and get a job. I had a job lined up. I was all set to wear a casual suit and get to work (lol, idiot me didn't realize the people I saw in my interview wearing suits were the business side and the software devs were all downstairs in jeans and a t-shirt).
I am sitting there, looking at this box, realizing this may be the last time I get to do this. I still bought some things now that I had a proper job and income. I moved to the city and lived with my sister who was far more outgoing and was rarely home. So I had a lot of privacy so I kept a few things around. Mostly sex toys. But I'd not really find much enjoyment from them. I didn't really enjoy any of the sex I'd have... with myself or with others... Everything felt wrong. The clothes I am wearing. Everything.
The saddest part in this entire journey is just how little I began to care about myself. I was wearing dress shoes I'd bought for high-school after my final growth spurt. The heel was dragged to the point it was a just a hole. I was wearing a size 32 waste when I'm a 29. I had lost a lot of weight in the process of living alone. My shirts were wrinkled and ill fitting. I was depressed. But not because the 9-5 grind. Because the life I was living wasn't mine. It took my mother and sister to intervene. I should really ask them about what they observed. But my sister and mother took me to proper shops got me clothes that fit me and dressed me like a 24 year old software engineer should dress (so like a casual button down shirt and chinos) and some new shoes (thank god). I think the only reason my hair got cut was because I lived next to a barber shop. This old Russian man cut my hair and was very sweet. I'd call in the morning, work from home that day, and then pop down and get it cut. I'd cry. I didn't want to cut my hair. But I had grown my hair out fully twice before. Once immediately after high-school (where I was forced to keep it tight) and then after leaving college. I got it cut because I assume my parents told me to. But I also hated that it didn't grow out how I wished it would (more feminine; like it does now). So I'd fight, what I thought was anxiety but was really dysphoria, and get my hair cut. Things were now "normal" after a strong push I was now a good boy in good clothes with a ... kinda shit job.
And I met someone! A cute shy fun girl. I was still depressed and dating wasn't easy. I came out to her as bisexual and I even mentioned how I crossdressed in college. She's the only partner I've ever been out to. I was happy for a bit. But with my depression once things got hard, she was still a student going into her final year, I bailed. I still feel guilty and I hate thinking about it. But we reconnected once she graduated and began dating again. And we're still together now. She was instrumental in the success of me coming out as transgender and I can't thank her enough.
But... I was now in a long term committed relationship. What about my crossdressing. I can't keep doing that. I only ever saw it as this sexual thing. She doesn't seem into that thing and I don't really want to disrupt what we have to introduce this fetish back into the bedroom... so it can just end here...
There were three main instances where I was handed the key and I threw it away:
Each time I was reading about trans people and just didn't understand. I really, really, didn't. I don't know if mentally I was blocking myself from understanding, out of fear, or if I simply didn't understand. I suffered a lot of brain fog, which I'll cover in a separate post, where I actually could not retain or comprehend things. I forever was seeing something then forgot. I even recall mentioning this to my partner:
Back before I left college I swear its like I couldn't retain information. I would be present in class, remember it for the test and it'd disappear! I'd be playing a game with my brother and immediately forget the rules after he told me. It was like my brain wasn't even on half the time. I really think the only reason I remembered my school work is because I knew I had to, or else. Anything that wasn't vital was just through my head, never in it.
But the last time, winter 2021, I was sitting at home with a new reddit account reading and asking questions. I swear it all just clicked. I can't even remember what made me start reading the subs again. Maybe it was me turning 30 and thinking about my future and what time I have left or what. I wish I could tell you, my readers, I wish... But I don't fucking know.
It all just rushed into my head. Everything I've shared on this site. All of it. I was sitting on the couch over the holiday break, awaiting New Years, and realized "I'm fucking trans!". That's all I remember. So I returned home. Told my partner. And have been living as a woman since.
This was a very personal and tricky post to write. There are a lot of details lost to time, and depression, that I can only feel in me, but not recall well enough to tell. There are so many little beats in life that I could mention but ultimately are so small and insignificant, to read, that I can't find a way to really tell it. Being trans is just one of those things I guess:
It's just who I am...it's hard to explain
It really fucking is. And sorry for swearing a lot. I know I couldn't really give you an answer. I would read the Stained Glass Woman post I linked. She's done way more for anyone actually struggling here, I am just trying to tell my story.
Thank you.
[0] https://stainedglasswoman.substack.com/p/beneath-the-surface