NB: I am a cis woman, assigned female at birth, and I’m pretty happy about it. I have never felt a need/desire to transition, so this is not that kind of story. It’s a different kind of story.
When a girl-child acts and dresses kind of like a boy-child she is called a tomboy, and that was me. I liked to climb trees, hang out with boys and play with gadgets. I favoured trousers and pockets and came home with grass stains on my jeans.
But, I also fancied boys and wore dresses and when Clueless the movie came out I fell in love with long socks and miniskirts, and I adored wearing shirts with a short skirt and heels. I played with dolls, kept a secret diary and devoured teen romance novels. I was obssessed with relationships and boyfriends.
For me, any behaviour that is normally gendered seemed to be theoretically on the table. I understood that people often divide down gender lines but I felt that you didn’t actually have to. Anyone can grow up to be anything, right? Such was the luxury of being a girl in the 80s/90s. So I happily sampled from both genders in terms of behaviours, clothes, thoughts & hobbies.
The local context of this ‘when I became a man’ story is much the same in terms of gender. I was in my late 20’s, newly out of a long relationship, newly out as bi, and also quite newly polyamorous. I was a passionate feminist activist, and a menstrual activist. I talked to people about their periods, having completed my dissertation on it at university. My friends called me ‘the period lady’. I loved being female and was making more and more female friends.
I was also deeply engaged with masculinity, what it means to be in the “active” role in a relationship with a woman, especially sexually, how to ‘get girls’ and so on. I was also curious more genereally since I’d always had such a strong masculine side throughout my life. I was reading radical feminist texts and hanging out with lesbians, while also trying to have sex with lesbians, and also feeling more kinship with men as my friends and lovers. Armed with awareness of how to deconstruct gender, I was exploring what being a man really means.
I played around with lowering the pitch of my voice, I dressed in a masculine way, I already had short hair and a bit of swagger, I sometimes pencilled a moustache on my lip at parties. I was curious how much you could do without changing your body in any way. How much was masculinity a state of mind, and how much could you project that to others? How much does biology matter when it comes to being a man?
I like to think I was quite successful. When feeling masc I was constantly ID’d for alcohol because I looked like an 18 year old boy. As soon as they looked closer they could see I was a nearly 30 year old woman, but the first glance had completely fooled them. I was also mistaken for a guy in shops or in bars, with people greeting me and my friends as “lads” and “fellas” until they realised I was clearly female.
I discovered how warmly men treat other men, when they think no women are around.
I sunbathed topless all summer that year with my guy friends, to see if I could trick people even when naked, by my posture and by being in a group of other guys. It worked. It would take people whole minutes to realise I was actually a woman with my tits out. I was never bothered about it or arrested, even though I was in public parks or in our front garden facing the street.
I interanalised a lot of it too, fairly frequently commenting “come on, you can speak freely, we’re all guys here” or accidentally miscounting the number of men and women in a room because I’d counted myself as a guy.
I also had a friend where me and her joked that she was my “wife” and I was her “husband”. Here I am with a protective arm around her chatting away while she rolls me a smoke.
Setting the stage: Makron
One of my best friends from this time was Makron (not his real name). Here’s us.
Here’s me imitating him while we roll cigarettes.
Makron (and our other male friend Feo) never questioned my desire to act like a guy and were completely on board with me relating to them as a guy would. It wasn’t hard, we were all into smoking and video games and talking about women. Makron got me into drum n bass and we would go moshing together. Feo patiently played Halo with me on the Xbox 360 while I got the hang of analog sticks on the controller. We would fuck around yelling at people on the street and trying to slap each other as hard as we could.
Makron loved women and dated various people on and off during our friendship. I slept with three of the men in the house we lived in, including Feo and Makron, and slept with several women in our friendship group. Makron and I talked openly about our escapades and once he mentioned that none of his girlfriends had ever let him do anal, because even if they were into it, his penis was too big.
Another time, I asked him when he lost his virginity, and questioned him when he said he lost it “properly” at age 18. I had to drag it out of him but it turns out that while he lost his ‘virginity’ to a woman at 18, he actually lost his virginity to a boy at age 15, back when he lived in Portugal. Him and this boy were fucking for about a year, so it was not just ‘experimentation’ or an accident at school. This was a whole thing!
He once mentioned that he’s mostly into women, but for some reason he starts to find men attractive in spring time. How awesome is that? Bisexual men exist y’all.
Another thing about Makron was that he refused to wear condoms. Not only was this bad for me because of diseases and being poly, I also had stopped using hormonal contraception years before, because of its negative effects. Between that and him having monogamous girlfriends, our sexual interactions were limited.
The time I turned into a man
One day, at a party, Makron was really horny and so was I. We really wanted some kind of sex to happen. He wouldn’t budge on the condoms but I told him that I was into anal and willing to try.
Anal is always tricky but after a bit of fumbling we got his cock in me and he started gently thrusting. Anal is an extremely intense experience, almost overwhelming at times. But me and Makron were very close by this time, I trusted him and myself, I felt super secure and horny and we could read each other really well.
Suddenly I tuned in to what Makron was doing as he fucked me. He was touching my hair. Delicately, maybe even nervously. He was also not touching my boobs or butt, rather pulling on my hips and touching my neck. He was avoiding the parts of me that were female. At that moment a bunch of different realisations hit me from different conversations we’d had over many months. In one huge moment I realised that he was experiencing me as a man.
He had lost his viriginty to a guy and had tons of sex with him, but only slept with women after that. None of the women he’d slept with had ever done anal with him. And I spent all my time relating to him as a guy. Now here we were, doing something he had only ever done with guys.
He was touching my hair and penetrating my butt, remembering what it was like back when he was 15 with that boy in Portugal. He was a guy relating to me as a guy, and for all intents and purposes, I was a guy too.
My masc energy was more than willing to rise up and meet that, I’d been practicing with my mind, my body and my voice for months. Hell, I’d thrown off a shirt, waistcoat and tie and left my “wife” downstairs to come up and do this. I was overwhelmed by the physical sensations of the sex, and a little drunk too.
I ran with it.
In that moment, for just a fraction of a second, I feel and I like to believe I “became” a guy. My biology didn’t change, but I experienced myself as a guy while someone else was experiencing me as a guy, together in one of the most intimate ways two humans can experience and witness each other. It was and remains the most transcendant moment of my life.
Nothing changed after that. We’re still friends, though separated by time and distance. I’m convinced masculinity is largely in the body-mind system and deeply influenced by intention. The meaning of my experience is, as with all things, a complex interplay of many factors. I don’t know if there is some “essence” in biology that is required in order to be a man, and of course I will never know, but I’m certainly suspicious that it is required.
I’m not sure how to adequately sum up this story, but we’re all guys here, so maybe I don’t have to.