I’m writing this post to document everything that hinted at my later transition. This is a living list; I’ll add to it as I remember new things.
This post is about all the weird stuff I did growing up prior to transitioning. Needless to say, some of it is sexual; so if that’s not your cup of tea then it’s time to leave.
It is my hope that someone who is questioning themselves can find some comfort and courage by reading this. Don’t be discouraged if you don’t measure up to my level of madness or idiocy. My friend didn’t act strangely at all and she’s thrilled with her transition.
If you have questions you can email me at: firstname.lastname@example.org or find me on the dying micro blogging site Twitter @missamyjie
Girlfriends is as a good as any place to start. A lot of my peculiarities came out around them and they help provide a context to some of my other stories. Looking back I noticed that I almost never initiated a relationship. I would hang around even them until the awkwardness was so unbearable they’d ask me out of frustration. Most of my girl friends were convinced I was gay until I accepted their propositions. So close and yet so far 😛
I was anti-thesis of the boy that just wants sex. I wanted to be “really good friends” that spent all their time together. That cooked and cleaned together. That lived together. I didn’t mind sex, but preferred if she lead.
In 8th grade, my first “girlfriend” would invite me over to her house. We’d go into the basement and watch movies. Her mom was a “cool mom” because she’d just give a knowing smile and leave us be. Despite all this, I always left a space between us and more focused on the movie than her. She moved to a different town and broke up with me.
It’s not that I didn’t like her, or that she wasn’t pretty. It was like we were friends, not boyfriend and girlfriend.
Middle school is stupid anyways so this barely counts. It does corroborate the pattern though.
My next girlfriend was part of my robotics team friend group. She constantly tried to get me to have sex with her in ways I found painfully embarrassing. I never did have sex with her although she did get me to do some sexual things with her. I think she ended up cheating on me, but I never bothered to confirm. I did, however, find out she had dated most boys I knew for brief periods. I was the only one to resist her siren’s call and I think that threw her through quite a loop.
I remember sitting on the couch with her and she came on to me, as strongly as ever, and asked me what I’d like to do. Like a total weirdo I blurted, “We could switch clothes.” She was briefly taken aback by the suggestion but then followed up with “Oh? And why is that?” Obviously, I wanted her to facilitate my crossdressing. For better of for worse I replied, “To see you naked” instead. She seemed content with this but I was so upset that I couldn’t feign interest and went home.
Holly was the first and only girl that I made a move on. To be fair, I did sit next to her in the school hallway for an hour each morning for an entire year before asking her to prom. She refused to go with on account of having a boyfriend, but we ended up dancing in the school parking lot after prom had ended and dating shortly thereafter.
We dated until I was suspended from college. I crossdressed in her room a lot, shared my nascent trans thoughts with her and even convinced her to peg me twice. I have a sliver of a memory of her intimating I should “get help at an LGBT center” and me quickly shooting that idea down. I’m just weird I’m not TruTrans™ Haha.
I was super clingy and she was wisely more interested in studying than having sex with me. I also think she stopped thinking my crossdressing was worth enabling and decided it was time to move on. Move on with my friend 😒 but move on all the same.
I met Sasha when I returned from my suspension. She caught my eye in the computer science class I was taking at the time (for reasons detailed below 😏) and, in desperate need of new friends, I sat next to her.
She eventually warmed to me and I would come over to her house everyday to talk with her. She started intimating that I should spend the night and I took the hint and slept on the couch. Then she said I should sleep in her room on a spare mattress. Then she dragged the mattress next to hers. Then one night she rolled onto my bed. I figured it out eventually and we dated briefly before she broke contact for another guy. We got back together at some point and we friends to this day.
Nina went much the same way. We met at a party and eventually started hanging out. Night after night I would visit her, drink wine (first time I started drinking) and Netflix and (actually) chill on her couch. We were like a couple without ever saying it, or consummating it. This charade would have gone on forever had she not climbed over me on the couch and kissed me. I kissed back and when we parted a wave of relief passed over her face as she exclaimed “Oh thank god, I thought you were gay!” I quickly laughed it off, “You’re not the first girl to say that.”
One night, while lying in bed, I confessed that I often thought about being a woman. She was understandably confused and cautiously probed me further. I got flustered and went to sleep.
Much, much later, near my coming out time she asked me The Button Question over dinner. I forget what prompted her to ask, but I do remember pausing for about thirty seconds before answering I wouldn’t press it. I knew what it meant to say “yes” and I wasn’t ready for that.
There was some occasional crossdressing with her as well, bringing us to our next topic.
I started to crossdress around the 6th grade. I did it mostly in private, and occasionally in public when I could get away with it. I “borrowed” clothes from my mom, sister and girlfriends, bought my own online, rummaged through clothing drives in my dormitory, and of course, purged my collection when I felt ashamed or thought I’d be discovered.
Crossdressing was a mixed bag. I felt compelled to do it. It was an extreme version of the hopefulness and disillusionment you may have experienced buying clothes. While shopping you imagine that you will look as good as the model if you bought that top or those shorts. Instead you realize that it wasn’t the clothing, it was the model’s body. Almost anything would look nice on her. Once dressed, I’d usually feel bitter disappointment. Nothing would fit right; instead it seemed to call attention to all the ways I was not a woman.
Nevada, by Imogen Binnie described it best through her character James (who is an egg).
After she came over that night, and after they had sex, and then after she went home, he did try it on. It looked like a skirt and a jacket, but it was actually only one piece, a dress. Maybe because he’d already come once that night, or because the dress was so ugly and stupid, or maybe because his ribs were all full of disappointment and helium, whatever it was, he didn’t even get turned on when he tried it on. He had expected to. The whole point of actually getting his first dress was to satisfy this impulse that was supposed to be all sexual.
He didn’t have a full-length mirror or anything, but he could barely figure out how to get his shoulders into it, and then it tangled around his ribs and armpits and he was worrying that he was going to stretch it out and ruin it— wouldn’t it be a tragedy, to ruin such a beautiful thing—but eventually he got into it and felt probably dumber than he had ever felt. There was tons of room and drape in the hips. His stomach, even though it barely even exists, bulged out against the front of the dress. He realized that he hadn’t known what he’d expected to feel when he tried this dress on, but it certainly wasn’t this emptiness verging on boredom butting up against wanting to die.
A painfully familiar feeling. There was nothing fun or sexual about crossdressing for me. It was wishful thinking that if I dressed like a woman maybe I’d look like one to (and then people would regard me as one and wouldn’t that be lovely).
Bras to Bed
While I lived at my parents house I frequently wore bras to bed. I would fold two boxers into squares for light padding. There was something right about sleeping with the weight on my chest. I was usually the first person awake in my house so the risk of discovery was minimal. As a backup I would move my night table over an inch to block the door. This way, if someone came to wake me it would buy me the seconds needed to recover my wits and avoid an awkward discovery.
I had a dream that my dad had woken up extra early one morning and knocked on my door. Bleary eyed, I climbed out of bed and opened the door and listened to my dad tell me he had to go into work early so he needed me to take care of the dogs. I nodded in ascension, he said good and then with a condescending smirk snapped a bra strap and left. My bowels turned to ice and I awoke with a start. It was so vivid that I wasn’t sure if it had happened or not. I was able to confirm after coming out that it was just a dream.
I only crossdressed in public twice. Once in high school and once in college. Always in the dead of night as to not run into anyone. I’d spend the entire time terrified until I made it to an empty public place with long lines of site where I could enjoy being out of my room.
I would occasionally trap it up and go on Omegle’s video roulette. I never said anything. I just wanted to figure out if I had a chance at passing.
A year and half after coming out I was at my family’s cottage on the lake. I still didn’t have a swimsuit, so my mom let me borrow hers. I went upstairs to put it on and halfway through dressing myself a wave of déjù vu passed over me, causing me to pause. I laughingly recalled how this was not the first time I “borrowed” my mother’s swimsuit. When I was younger, I would stay at the cottage when the family went to town and so I could try them on. The good news was that I looked much less ridiculous this time.
During my freshman year of college I convinced my poor girlfriend, among other things, to let me dress up in her room and use some of her clothes (the ones that I wouldn’t immediately break in half at least).
While going through my Google Photos backup I found a short video of myself dressed up in her apartment that had apparently been spared during my purges. It’s very embarrassing. What am I wearing >__<;; (probably whatever I could find that fit).
Literally kill me.
She was also the girlfriend I was with during the end of the semester clothes collection. I surreptitiously went from bin to bin and floor to floor to see if there was anything in my size I could pilfer for my wardrobe.
My next girlfriend would not enable my crossdressing. Instead I had to goad her friends into suggesting it as a source of amusement. Eventually they’d drag a reluctant agreement out of me 😏
For Halloween I planted the idea that I should crossdress and dance with a slightly homophobic housemate of mine once he was sufficiently drunk. I went shopping with my girlfriend and tried on lots of clothes. I even found heels in my size and made up some lie how I came in possession of breast forms. The plan was a success. I passed well enough to give my plastered housemate a surprise greeting. Afterwards I went upstairs with my girlfriend. I was hopeful I’d get to wear the outfit, or at least the bra and breast forms but she insisted otherwise. Not her cup of tea.
As for the breast forms; I would wear them to sleep or while working alone in my room. Something about it just felt right.
The cycle of starting a secret wardrobe and then purging it continued until I transitioned. I’m still not a fan of drag or crossdressing. I almost snapped my spine in half cringing at the above video of myself. I’ve not watched RuPaul’s and I’m not going to your local drag event so stop asking 😛 It’s not my cup of tea.
Growing up I was very into a very specific subset of porn. Namely porn and erotica describing men becoming women. This is so niche that it is almost universally terrible. The writing is terrible, the art is terrible. You have to search a long time to find something worth reading or whacking off to.
If this is what you consider “porn” you might want to talk to a gender therapist.
To this end, there were a couple of content aggregators dedicated to sorting through this smut so that you could feast on the cream of the crop (so that you could harvest your own crop of cream). They invariably disappeared and someone would setup another one.
At one point there were no suitable aggregators for so long that I took it upon myself to build the next one. I learned Linux, how to administer servers, structuring databases, LAMP, front end and design. I built a truly terrible website. Content must really be king because lots of people liked it anyways though. I ended up rebuilding it much better a second time (although still awful). It got so popular that I ended up taking a computer science class to learn better software engineering techniques.
In summary, the reason I discovered I loved computer science, received a degree in it, got my first job and met Sasha was due to my interest in porn. Thanks porn =^__^;;=
Eventually, my site mysteriously disappeared as well. I decided to put this weird fetish behind me and move on with my life (and failed miserably). Until read Nevada I had always assumed I was a deviant. Again, Imogen Binnie’s character James proves uncannily accurate:
It’s not like James is proud of the porn that he looks at, but what are you supposed to do? Will yourself not to be a pervert? He’s tried. He’s still trying. He tries most nights…He knows how this is going to end, though. He’s going to try to watch men fuck women for about half an hour, get depressed, not be able to even get hard, and then look at blogs of pictures of women with captions that turn the pictures into weird and absurd erotic transvestite scenarios.
It’s like, this is no longer a dumb picture from a fashion magazine or a porn shoot or a Halloween costume advertisement, subtitled with a stupid scenario. Suddenly this shit is functioning in your reptile brain the way that pussy is supposed to function.
James isn’t gay or anything. He’s not that into the ones where there are dicks. The ones with lesbians, sure, but he’s not into dudes or anything. Like, being a pervert would probably even be easier if he was gay…If you’re a straight guy who’s into the idea of being turned into a girl there’s not a lot of girls who are interested in being involved in that, probably.
It’s supposed to be called autogynephilia. It’s like a thing. That’s the name of the fetish. If it’s a fetish? James doesn’t know what it is. Being sexually attracted to oneself as female. Hot! Who wouldn’t be hot for that? Gross.
It’s the sort of thing you can never tell anyone. A secret you carry with you like an albatross stapled to your neck that you take with you to your grave.
Lots of other fetishes or whatever, like, you can frame them as cool…But wanting to be a girl? Not even like, I have known my whole life, man trapped in the body of a woman, whatever. Anyone can tell you that James is not a woman. James knows who Jennifer Finney Boylan is, and he is no Jennifer Finney Boylan. He’s just some fucking dude who wishes he was allowed to wear dresses.
He’s looking at a picture of a girl in a French maid Halloween costume: Philip’s girlfriend was furious! It seems he couldn’t be bothered to get a costume for her big party so she got one for him—and it was a dress! It’s absurd and he can’t even focus on it. He’s a million miles away, imagining how ridiculous he would look in that dress, working out scenarios for ways that he could ever connect with another human being about this stupid.
What kind of twenty-year-old guy has a lot of trouble coming unless his girlfriend is sucking his dick so he can think about the evil ice sorceress turning Brave Samson into a demure maiden?
Ugh. Fucking End Me.
If you’re “greatest fantasy” is to be turned into a woman you should probably see a gender therapist.
My dad set up a proxy server between the LAN and the wider internet. I was tech savvy enough to avoid leaving a log of where I visited but I still made mistakes from time to time. Well, my dad must have been checking the logs because one day he came to talk to me about porn. Every kid’s nightmare made manifest. I thought I was going to be asked to explain what I couldn’t even explain to myself.
He told me not to watch anymore porn and nodded silently in agreement. He then handed me a book on LGB subjects and told me I could ask him if I had any questions. I flipped through the book scanning for the word “transgender.” It appeared only in a footnote. I distinctly remember thinking “This book has nothing for me” and throwing it under my bed.
In a horrifyingly ironic way I was considered to be very secure in my masculinity. Disparaging my status as a “man” universally failed to register as an insult. Probably because I didn’t think much about being a man.
On the other hand, on the infrequent times I was mis-misgendered (referred to as a girl before I came out) my heart always soared.
I remember eating dinner with Nina and her mother. When the check came, they offered to pay for it since they had jobs and I was still in school. Her mom facetiously asked me “how I liked being the woman” and with a dumb grin on my face I said it felt great.
I’m still not sure how I rationalized these things to myself. I knew what I meant by that statement. I knew it made me feel good. I repressed connecting the dots.
Like this ancient photo:
I knew why I wanted a pic of my head in the cutout. So that I could go home and try to visualize what I might look like had I been born female. Never daring to ask “why” I would want to do something like that.
In the same way I wore a bra to bed most nights, I would lie in bed imagining being a girl. Trying to figure it out if it was better, if it would be worth the trouble.
Sometimes I would listen to these audio recordings that would hypnotize you into becoming a girl. Even as a middle school student I knew it was impossible. Most of them were fairly erotic and weird, but you could find a few vanilla ones. I suppose I’d take whatever had a chance at working.
I also had lucid dream in which I was in a hot tub on wooden balcony overlooking a snowy mountain side. A party was going on and there was a bunch of other teens milling about and having a good time. After sitting for a while I realized that I was dreaming and remembered the concept of lucid dreaming. No sooner than I remembered, a magic lamp appeared in my hands (apparently my way of making anything happen). I rubbed it an was granted one wish. I couldn’t think of anything I wanted so I wished for something dumb. So dumb I don’t even remember. I do remember my eyes opening in panic as I realized I could have wish for that.
Fortunately, the exiting genie acquiesced and granted my new wish. I was female! I sat back in the hot tub with a stupid grin on my face and enjoyed watching the fresh snow blanket the mountainside until I woke up.
Tests, Quizzes and Such
I spent a lot of time taking quizzes that purported to tell you if you were transgender or if you were more like a boy or a girl. I was also cognizant of the answer I wanted to see at the end of the quiz. I told myself the quizzes were meaningless but never stopped to think why I acted like they had meaning to me.
In middle school and possibly earlier, I was very well learned in chromosomal disorders, sex hormones and gender reassignment surgeries. I was particularly amazed how much hormone replacement therapy could change a person’s body. I was always scouring the internet for a case of someone very young transitioning. I frequently wondered what would happen if someone my age was started on HRT and if there were any countries that did it that early. Not that I would have wanted it done to myself, I was just really curious what would happen if someone my age did it. That’s all. I swear.
Growing up I was a big fan of the Animorph series; where teenagers gained the abilities to shape shift into any living thing they touched. I’m not quite sure when I first encountered them but it must have been between the ages of 4-8 given the series’ publication.
I remember seeing the fourth installment of the series upon walking into my school library. There was a girl changing into a dolphin into the cover and knew I had to read it. “I wonder if any boys change into girls in this series.” was my first thought upon finishing the book and I quickly read the entire series. I found out that a gender-morph does indeed happen. In book 43 Tobias morphs from a hawk into a woman. I always identified most strongly with Tobias while reading. Which was funny because we had nothing in common. Unless you count being stuck in the wrong body ¯_(ツ)_/¯
That’s all I could remember. I’ll add to this as I think of more tranny bullshit I went through before I came out.
If you found this piece unreasonably engrossing, you’re probably an egg 😉