My Boyfriend was a Ladyboy

Even after death, I still see his beauty


Original artwork by IG: @ryan_flux

A year into our relationship was the first time he asked me if he could wear my heels …

I hesitated. I wear a size 9-and-a-half female shoe; and he, a male size nine shoe. He squeezed into them at first—after time eventually claiming them his, as they became too stretched for my foot to comfortably fit any longer.

He was sitting on the couch in fishnets — nothing else.

He had a face that, whichever way you wanted to look at, could contort to a beautiful woman or a handsome man. I would tell him that if he had only been a little taller, I could see him walking down the runways of Paris or Milan as he was an unconventional beauty, androgyny being his main suit. His hair cascaded down his back only when he decided to be his second self—or when we made love.
During the majority of our relationship, his wardrobe consisted of black button ups, beige Dickies and DC skater shoes. He wore this like a uniform for life. I remember always wondering why he never ventured off into other styles or other cuts, other forms of clothing–colors, what have you. He always claimed that the great minds of this world always claimed their own “uniform”: Steve Jobs, Bill Gates, Steven Hawking e.g. His uniform is what he felt comfortable in. It was not until I understood that what he really wanted to wear was not what he thought to be systemically-socially appropriate.

I have always been an LGBTQ+ rights activist and advocate. I’ve never pin-pointed to where this “liking” had fallen into that spectrum, or if it ever did. We were us. He was comfortable being himself with me; sexually, mentally and emotionally. He expanded my horizons of what not only being intimate with one another meant or could be, but to a degree, how fluid I could be as well.

He had his own makeup bag, he had his own wardrobe, he had his own costumes, he had his own shoes and he had himself with me–his true self.

I remember being envious of how beautiful he looked with a full-face of makeup on, so much so; I felt like I couldn’t compete. Funny as it is, I liked it. I loved him; I loved everything about him. I thought him to be the most interesting person that I had ever met. We enjoyed making late-night runs to the sex shop for new “gadgets” if you will. It was exciting. It was something that neither of us ever felt comfortable sharing with anyone else but one another. We would then shop for his taste in nail polish, usually bright reds, and new makeup. I never brought this up to him, but I thought that he believed–with the veil of the night–his secret wouldn’t be revealed. He never wanted to share his tastes with anyone else but me, and as far as I’m concerned, he never did.

There were times where I questioned if this was normal. There were times when I questioned if I really liked it.

I never wanted him to feel ashamed of who he was or what he liked, but there were times when I thought that I was negotiating what I really wanted in a partner. I’ve always seen myself as a straight female and acted as one. I made compromises in my own sexual sense and lifestyle to make sure that this beautiful human being, who felt safe and compelled to open up to me, would not feel scorned or shamed for what he wanted and what he lusted. I found myself confused. The compromise took a toll between the two of us.

He died in a car crash on November 27, 2020. It was the worse day of my life.

He had a substance abuse problem which I think was an attribution to not knowing what to do with his true self, as well as other underlined issues. He never revealed his secret to his family or anyone else. He expressed to me on several occasions that he was embarrassed to share himself. This feeling of self-distain made him feel alone. He was the golden boy. He graduated from a prolific school with a master’s in aerospace and mechanical engineering. He felt the need to fit into a certain persona and lifestyle, something that he thought would be conflicted had he opened-up.

He questioned his sexual orientation at times; I couldn’t help the internal confrontation that he had. I couldn’t save him from himself. This made me feel helpless. I always wanted him to feel comfortable in his own skin. I thought it wrong for any man or woman to be conformed to a systemic sense of what masculinity or femininity should be. Why couldn’t my boyfriend feel pretty? Why couldn’t a man feel beautiful? I thought he was gorgeous.

I will forever miss him. I miss his individuality, I miss teaching him how to execute a perfect winged-liner, I even miss him stealing my clothes. The most of all, I miss the love and trust of my best friend.
When I think back to our relationship, and the time that I had with him; I feel some closure knowing that I was able to give him some solace and some relief knowing that there was someone out there that loved and accepted him for who he was. It kills me to know that I will never see that beautiful hair, those eagle—half-moon eyes; the way he walked with a handsome femininity in heels around the house– the confidence and comfortability he had around me when he did it; smiling as he looked back at me because he could feel my stare. I was in awe of it, walking art.

I miss you.