My Attraction to transgender women shouldn’t be a secret

This is a repost of an article I originally published on Medium and at The-News Hub.

I want to begin this article with a warning. I have deliberately been graphic about some of my experiences because they have been pivotal points in my life and my growth. Experiencing them with me might just give you an idea about how I felt during those moments. They are very contrasting experiences; some cold and unemotional which failed to live up to my expectations and some beautiful and deep – moments I wish I could experience again and again.

I never thought that I would ever be okay with writing an article about myself with the admissions that I am about to divulge. The truth is: I’m still slightly insecure about my attractions and sexuality. I worry about what the world will think of me; I worry about it diminishing the respect that my co-workers have for me, about losing that camaraderie with the people I work with and the “guy atmosphere” that we currently have. I don’t want this to make me different or special.

Let’s rewind – to a Pentium 90, 8MB EDO Ram and US Robotics Modem that was a hand-me-down from my dad’s friend. Now at some point (and it’s not a point in time that I had regarded as significant) I found porn. Now as a kid you are naturally curious and back in the days of pop-ups and Warez (illegal download sites) usernames and passwords being bandied around the internet, you occasionally got access to some new and interesting stuff.

Remember, I’m 12. Sitting at my computer. Looking at porn on our 640×480 screen. I’m now presented with a gorgeous woman from Thailand who has an ample sized penis. Hold on — there is a woman on my screen, but she has a penis. She’s attractive. She has breasts. She has a penis. And I’m attracted.

Now here is where things feel like they get complicated. I’m not looking at gay male porn, I have no interest or attraction towards guys; I never have. Yet I’m attracted to a woman with a penis. As a 12 year old kid with no guidance on the matter and no Wikipedia, I have only my own assumptions. I don’t even know how this woman is real — they didn’t teach us this in sex education.

This is where my denial and lies began. This is something I carried with me, kept to myself and didn’t act on until my mid 20’s. This isn’t something that I experienced and forgot about; it’s something that was always there. I cannot tell you the number of times I’ve been browsing through my movies folder on a network share and “Shemale Porn” flashes up. Instant shame and self-loathing kicks in. I try to blame my current girlfriend — it’s her fetish not mine; I’m totally just indulging her. Except this isn’t just someone’s fetish that we are talking about – it is a type of woman that I am attracted to and it would be too easy to pass it off as a fetish.

I can’t tell you the number of times my heart would start racing when people crowded around my laptop or computer to type in a URL and it started with “T” or “S” or “L”. I was always living in constant fear that someone I cared about would discover this dirty little secret of mine that I could never quite shake.

Let me ask you something — imagine you are a 6’7” tall, built, alpha male-type guy, friendly but firm; a natural leader. Not a single person in your life would ever expect you to be attracted to transgender women. Who do you talk to? Are you part of the LGBT community? Are you a “tranny chaser” or admirer?

The truth is (and I can whole-heartedly say this after spending all of my adult life living with these feelings) there isn’t an obvious place for you to go. There isn’t anyone to talk to. There are no groups.

So let’s make a quick list:

Attracted to Women: Check.

Attracted to Men: Nope.

Attracted to Men in Drag: Nope.

Attracted to Transgender women who don’t pass: Nope.

Attracted to Passable Transgender women: Check.

This, by my logic and years of mulling it over, makes me heterosexual. I’m not bisexual, nor am I gay. I am attracted only to women, penis or not. This is purely a physical attraction.

I used to worry about what Jeremy Kyle or Jerry Springer used to think. And I constantly worried about what my friends would think.

It took me a long time to decide I wasn’t gay or bisexual and feel comfortable with that admission and truly believe it for myself. I can honestly say that I’ve never thought of a transgender woman as anything less than a woman. Knowing first-hand how it feels to wrestle with the way you feel inside and everything on the outside, these women absolutely deserve to be treated the way they feel.

Over the years I’ve met some amazing women. Some have passed through my life; some have become my closest friends whom I absolutely cherish. One of my closest friends, Emilia, has been there for me so many times I can’t even begin to count. I used to hate myself so much that I would cry myself to sleep every night when I fell in love with her but never considered myself to be worthy. In a way, I think we’ve both been there for each other, during her growing up and transitioning to me slowly getting more comfortable in my own skin. Truth be told, she has probably been my personal psychologist.

I gradually started telling my friends over the course of several years. Secrets get heavier with each year that passes and it gets harder to hide a part of yourself. I had a plan: I structured the order of my admission based on how judgmental I thought they were, how long I had known them and how devastated I would be if they called me gay and removed me from their life. These were all guy friends.

The first guy friend I confided in, Tom, I told just before I was meeting a transgender woman for the first time at my apartment. This was going to be the first time I had ever slept with a woman like this – I figured I might need to talk to someone afterwards.

It hurt. It was rushed. I learnt that I had much more of a dependence on an emotional and romantic connection than I’d realised. That was the first one-afternoon-stand I had and it wasn’t the last. But this experience taught me a lot about what I needed to enjoy myself.

You might wonder why I would want to try something again that was such a bad experience first time round. But even after that event, my attraction never went away. I guess I figured it was kind of like olives. You eat enough of them and you actually enjoy them. There was a bit of enjoyment the first time. But it wasn’t the romantic, euphoric moment that I had expected to share with someone.

I guess this begs the question: why a one-afternoon-stand? Let me put it like this; you can share anything with a stranger, and I very much doubt you would be concerned about their judgements and what they think of you. In many ways, it’s much harder to tell a partner you have known for some time your deepest darkest secrets. Over the years I’ve developed the approach of being very upfront with mine because who cares if someone leaves or dumps you at the beginning over judgement? A stranger is someone you can try something new with, something you might not stick with, an experiment who won’t cast a judgement that will haunt you.

I’d like to tell you another story of when I thought my life had ended and when I found “The Scene”. I had arranged to meet an absolutely beautiful woman – think Jessica Rabbit. She was almost as tall as me in heels, with the most seductive smile and voice. I’d never been so smitten, and my fear and self-hatred had never been so far away. Meeting her publicly for the first time should have been a big step for me. Because I was so wrapped up in just having a drink with her, I had not even considered I was meeting a transgender woman in public for the first time.

We spent the entire evening talking and flirting; I couldn’t stop looking at her eyes, and she was a seductress of the most advanced level. I think I would refer to this as Hyper-Femininity; a woman more female than any female you had ever met. In a way, this is one of the things that attracts me to transgender women.

Now, I will credit her with a few things. Primarily, the first time I had ever been to a gay club was with her. I clung to her arm like my life was at stake and I didn’t leave her side all night. She knew everyone and everyone wanted a kiss on both cheeks and I was more uncomfortable than I had ever been in any situation. Ever.

I would have done and gone anywhere with her, so it wasn’t the last time I ended up in a club like that but I never left her side while there. One of the last times we went out together was to a well-known Birmingham drag club, with her female friend and partner. Some of these experiences definitely contributed to me feeling more at ease; like this was all normal.

As we flirted and talked and watched the show, she placed my hand under the table in her underwear. I’d never touched her before and this was in public. I was so shy, I remember feeling like I was going bright red. I wasn’t even sure what I should do — what was the protocol?

What I liked about her was how she took the lead: she placed my hand in her pants, not me; she would walk further ahead when we were out, slightly tugging on my hand as if to lead me. No woman has ever been able to push me up against a wall, kiss me and leave me feeling as vulnerable and desperate for her attention as she could.

Later that night I left and she stayed out. I woke up the next morning to go to work, and while I was in Tesco getting some breakfast, my neighbour professed that he had not only heard what I did last night, but that every gay man in Southside Birmingham had. To make matters worse, the drag act on the stage had seen what I was doing under the table and made it part of the night’s entertainment. I was devastated! My life was over. I didn’t even want to leave my apartment. But funnily enough, life went on and everything was forgotten. It’s silly how big we make these things in our mind.

Now one more thing I have to accredit this woman with is being the reason I told my dad. I had fallen for her so much I absolutely wanted to date her; she was a goddess, and I was amazed that she was even talking to me. I’d cooked for her a few times (I even practiced making the dish three times to get it right) – I had never done that for anyone. I remember calling my dad and telling him how much I liked this girl and that I wanted to date her. I also remember choking over the words “she wasn’t born a girl” like it was something I had to disclose. The simple truth was that I didn’t want her to be a secret; I didn’t want her to ever think I was ashamed of being with her or embarrassed. My dad of course was okay with it and simply said “whatever makes you happy”. I don’t know what I had expected from him, but the result was good. We talked about having kids and my feeling that I had an obligation to have them, but dad reassured me that the only obligation I had was to me alone.

She was the first transgender girl I think I loved. I didn’t even consider how anyone else felt except me and her. But it soon became clear that she was a pathological liar and more of a fantasy than a realistic partner.

Let’s move on to the second girl I felt something for, Anastasia. I met her though a mutual friend. I think all three of us spent a Saturday drinking and watching movies at my apartment. She was sitting at one end of my three-seat sofa with me at the other. I think our feet were touching. Later on she got up to get a drink and then we were sitting on the same seat of the sofa. I was attracted to her from the moment I saw her at my door. As the afternoon passed, the touching became fondling, as the alcohol flowed the inhibitions and the fact that there was a third person in the room drifted away. I’m not entirely sure when our mutual friend left, but she did.

Now I can only describe this next “scene” as something resembling frightened teenagers experimenting, except I was 24. Both of us had our jeans undone and hands down each other’s pants. I think it would have been fair to say because of the mutual attraction we were both nervous as hell.

The braver one of us (I forget who) pulled the other’s penis free of their underwear. The other followed, and soon our jeans were off, and my penis was in her mouth.

I’m going to interject before this next part. This isn’t actually the first time I sucked someone’s cock. I did that the first time I had anal sex with a transgender woman. I didn’t mention it though because it felt forced the first time and I regret the entire experience. I feel ashamed that my first time was so rushed, forced and painful; it lacked the romance I had imagined and anticipated.

Back to the story: I pulled her close to me, kissed her as to say I am okay with all of this and slid down the sofa before taking her cock in my mouth. This was an entirely different, slower, erotic and intimate experience. I really liked this girl; we connected, and there wasn’t a single thought about what I was doing or what it meant in my head — just a beautiful moment between me and Anastasia.

That night we slept together, in the literal sense – nothing happened sexually. We were both a bit drunk and she was transitioning. I wasn’t sure if there was some sort of “who goes first” etiquette I was unaware of. It felt crude to ask, so I held her until she fell asleep. If I said I didn’t regret letting the day end that way I would be a liar. I will regret that for the rest of my life. I will always remember how attracted I was to her; I will never forget how quickly that feeling of ease developed between us and I will always regret it never became something more.

What followed for her was an abusive boyfriend and a reoccurring drug addiction. You might ask why we didn’t have a relationship. Truth be told, as smitten with her as I was, that Saturday I was still in a relationship with someone else. I betrayed someone I loved for her. I was confused and cowardly. I should have ended my relationship that I was clearly unhappy with and started seeing her – but love and relationships aren’t that simple. I didn’t, and she met someone else who was an abusive asshole. I will always feel directly responsible for that happening – she deserves so much more.

Anastasia is one of the kindest, sweetest and most genuine people I know. I’m proud I can call her my friend.

I find it difficult to categorically know how I feel about a situation — that is; how I truly feel, and not some romanticised remnant of a feeling that I’m morphing into something else. I never know if I should be with one person or another.

I’m now going to walk you through two pivotal points during my life in London.

The first was a time when I was unhappy in a relationship with little communication and what felt like an endless distance between my partner and myself. I ended up wondering what it means. I’ve known since I was 12 that I was attracted to transgender women — should I act on it? I must be with the wrong person! To cut a painful story short, I broke up with my girlfriend, dated a transgender women for a bit and realised she had equally as many flaws as anyone I have dated or ever would date. I decided that person wasn’t for me and that being transgender or cisgender didn’t have a bearing on my happiness in a relationship or who I should be with.

During this time, I’d starting hanging around with lesbians; it seemed to help with the gender issues and made them feel more normal for me. I confessed to my boss I had these feelings and I was going through a difficult time and apologised for not really being on point. He is an incredibly gracious and understanding person who has given me more pivotal space to sort myself out than anyone could hope or ask for – I owe him a lot during a difficult time.

This brings us to somewhere between those two events where I decide I should tell my best friend, Mike. Mike is Chinese, and as Welsh and Brummy as Mike is, he is still conservative when it comes to certain things. I’m also the guy who he’s cracked gay jokes with and tossed gay slurs casually across the office with. I know this is going to be difficult for him as well as myself. We’ve known each other for about 14 years, and in that time there has been a lot of lies and denial on my part. We have an incredibly close friendship but we’re still guys who have a guy culture.

I’ve actually forgotten how I told Mike. But I remember him being very quiet for a few days and not talking to me. He called me one evening and said: “Do you want to talk?” Instinctively I asked if everything was okay and if he was alright, he replied: “No, about you.” My heart sort of sank. I was so scared of losing Mike as a friend, I couldn’t imagine my life without him because we are so synchronised. All the stupid hobbies I’ve taken up and made him join in with, all the adventures and bar hops. We even learnt to ride motorbikes together.

We met at the bar downstairs in my building. I was sitting down, shaking, very nervous. Mike walked in, and I asked him if he wanted a drink. He smelled like a bottle of vodka – and confessed it took half a bottle just to have this conversation. This was obviously difficult for him.

He told me I should have done this shit when I was 21, not 28. I told him it wasn’t that simple and that these aren’t issues you can publicly council. I asked him how he would have reacted had I told him years ago. I got a laugh out of him; I guess things felt the same. He said to me in some kind of Yoda-like logic: “I know you’re still the same, but something is different; it’s like you’re disabled.” In a weird way I knew things wouldn’t change. Over the last year he’s gotten a lot more comfortable talking about it. The irony is that the ladyboy jokes in the office continue and I have no idea what he really thinks. He’s my best mate and I know he would go out of his way to make me feel okay. I just stay quiet or join in when the subject bubbles up in the office; they don’t know and guys banter. I certainly don’t want to be the one to change things or make things serious just because something is a painful point in my history. Banter is harmless; it is what we make of it.

After I moved to London for work, I would occasionally come back to Birmingham. I remember one weekend around Christmas-time I was meeting two of my best friends; namely the one I’d had a crush on for an eternity, Emilia. I was always going to be the guy in the friend-zone with her; I don’t think she will ever know how painful it was at that time for me, especially hearing about her conquests and boyfriends. I did what any friend would do: I never said a word, and I refused to risk our friendship for anything, even my own feelings. I consider her friendship one of the most precious things I have in this life.

Before going out that evening she met me in my hotel room, slightly drunk. She decided it would be a good idea to have a bath before going out; she took off all her clothes and ran a bath. We talked and I tried not to stare. I’m pretty sure she knew I might have felt something for her. After she got out of the bath, she walked over to the bed and simply lied down. I don’t think I’ve ever seen a girl I could compare to how beautiful she looked in that moment; it will be a moment that I will never forget. I spent the rest of that night feeling lost, infatuated and wanting to cry alone. I just felt trapped and unworthy. I remember Mike’s words that night: “You’re in-fucking-love with her aren’t you?” I remember my eyes welling up slightly as he said it. By saying those words out loud, he had made it all the more real.

Mike and Emilia had never really met up to that point. We had Chinese dim sum together the next day. Mike was very quiet; Emilia text me after and said: “I think he wishes I wasn’t real.” She probably wasn’t wrong.

Let’s fast forward slightly: I’m out with a few of my friends on a weekend back home in Birmingham; a few of them know I like a certain type of girl, a few of them don’t. My biggest fear soon starts to become a reality before me. Mike and Tom have assumed another friend knows my secret and it’s an open conversation. They soon start discussing who I like – more specifically, Emilia. Something is said. My secret feels like it’s falling out. I’m inside a bar in Birmingham’s Arcadian and my eyes are welling up, the tears are about to burst; I look away and quickly walk out of the door. I am devastated. I am now in the corner of a car park in the Arcadian crying my eyes out. I don’t know who knows what. I haven’t told them. Someone has done it for me. And I still cannot stop crying.

Emilia knows me better than almost anyone, but she doesn’t know how I feel about her. She is the only person in the world I can talk to about this. I call her, telling her between breaths and heavy sobbing what just happened. She’s leaving with Anastasia to go on holiday shortly and there isn’t much she can do. I know at that moment exactly how it would feel to be “outed” for being gay or transgender and it reduced a 6’7” man to tears in a cold car park on a Saturday night.

Mike soon calls me and tells me that he is sorry and has managed to convince my other friend it was girl problems that he was totally unaware of. I had to compose myself and go back to the bar. I just told them I had too much to drink and was a little emotional. I wanted to run away that night; I wanted to disown everyone I knew and disappear into a black hole. I don’t think anything has ever upset me as much as that experience and I don’t think anything will ever surpass the sheer devastation of that night.

It’s funny how close I am to my two best friends. I’d never talk to Mike about the things I talk to Emilia about. Somehow when I talk to her, everything we have to say is okay and acceptable. We both can be outrageous at times. I’ve often wondered if it’s like a group therapy for both of us, talking out loud and sharing. I remember when she started dating her current boyfriend. We had all taken a trip to Bicester Village for a shopping day. My current partner and I are very open with each other sexually; my partner also knows that she can be open with Emilia as well.

At some point during the day, very casually, Emilia turns to her boyfriend and says: “You should talk to Simon about strap-ons.” Once again I am mortified and overcome with embarrassment. I have never in my life talked to a guy about anything like this and now I am out in the open and alone with my secrets on the table with a guy I had not long ago met. This was a horrible moment for me, but it was also a moment that helped me get over myself a little and make me feel at ease talking about this stuff to an extent. I still find it a lot easier to talk to a woman about anal sex than I do a guy. But I expect that’s just a guy-thing.

I don’t broadcast my sexuality. I don’t announce it. I don’t wear a badge or go to gay pride. I’m not proud. In fact, I was ashamed for a very long time. But now I accept who I am. I don’t have a group to go to, nor do I have friends who are like this. Consequently, I often feel alone.

These days I don’t mind telling people I’m attracted to transgender women. I don’t have to act on that attraction and I would date a cisgender woman or a transgender woman.

So, what’s changed? Where is the guy in the car park and who is that guy now? Well, I’m older and wiser; I’m number to some of the things I’ve experienced. I’ve realised I can be attracted to someone and not have to apply meaning to it or act on it. I’m very happy with my cisgendered female partner Dan. She could easily have been transgender and things would be exactly the same between us. While I might be okay with the world knowing I’m proud of whomever I date, it’s worth considering that if my partner was transgender, she might not want the world to know that. I wish I’d thought of that before I spoke to my dad years ago.

Most transgender women are going through a transition from one form to another; most will want this to become ancient history as soon as possible. It’s one thing being open about your partner, but how about after they transition, and want to forget about that part of their life? What about all that history and the people that they know?

I know girls who just want to move on once they have finished their transition and want nothing to do with ‘The Scene’. I also know girls who are quite the opposite. I really don’t want to speak for everyone on this subject as it’s incredibly sensitive and diverse. I will no doubt upset someone with whatever perspective I share — but I think what men are attracted to in transgender women, that exotic hyper-femininity, isn’t aligned with what women who are transitioning and planning SRS (Sexual Reassignment Surgery) want. I think the majority of men look for pre-op girls and for them to feel complete they often need to become post-op. I do however think that relationships are about the people and when two people are in love, they would do anything for their partner’s happiness.

Everyone is very different and this is but one guy’s perspective.

I will say this: watching one of my two closest friends transition; meeting girls from all walks of life; standing girls up and making excuses not to meet them because I was insecure and ashamed of who I was – all of those events have given me the utmost respect for women who transition and a deep personal regret that I couldn’t accept who I am earlier. These women deserve respect, support and love as much as anyone else. They are some of the strongest, most feminine and amazing women you will ever have the pleasure to meet. My pain and journey is minuscule compared to what women who transition go through, and I have only admiration and respect for them.

Truth be told, I’ve probably invented a lot of this pain and emotional scarring myself, but this is what happens when you are left alone to deal with something. Often, we magnify and twist things into evil abstractions that haunt and taunt us.

My name is Simon Stearn. I live in London – and I am who I am.


9 thoughts on “My Attraction to transgender women shouldn’t be a secret

  1. M says:

    Simon, your article has helped me so much, can you please get in contact with me, I have a few questions which you may be able to help with that I desperately need to talk over with someone with your experience.

    I feel so alone and powerless to change my situation. I think you may be able to help


    • Sure, contact me on the forum directly if you want, we can talk through anything you want to talk about. There are a few other members on the forum too so if you make it public and that’s up to you, they might be able to help. Well done for standing up though.


  2. James Saint says:

    Well written and honest. Here’s my brief history: I have had quite a few relationships with so called ‘cis’ women then I stumbled across an article by Paris Lees, I thought ‘wow! I’d date her’. I use the internet a lot and chat to people about all sorts of things and for all sorts of reasons. The Paris Lees thing was in the back of my head for a while and I decided to go onto a transgender dating website and just chat to some of the girls since I wanted to know more. No intention of anything else and I will say I was a little bit wary and unsure at the time. I quickly relaxed however and had some good conversations and made some good connections. Then I came across the profile of a girl who looked like a supermodel. I thought ‘what are the chances?’ When we chatted we clicked and found we shared the same perspectives. We both decided to leave the website and swapped details. The upshot is I will be marrying this girl next year in the UK. As far as other people and what they think, I don’t give it a second thought. I basically don’t care. It’s my life at the end of the day. What it has opened my eyes to though and you touched on this Simon, is the bigotry and nastiness that’s out there. I won’t have any of it. I will protect this girl with whatever it takes.
    The experience has made me somewhat militant on behalf of transgendered girls (well someone’s got to do it) so I take great pleasure in joining discussions where transphobes are venting their ignorant bile and shooting them down in flames… well as I say, someone’s got to do it.

    All the best to you.


  3. Charlie says:

    The beginning of this article could have been written by me.

    Though I knew about my attraction from I was around 16, and didn’t act on it until I was 28, and only now at 32 have I decided to actually take a transgender woman as my girlfriend.

    I thought it was just a sex fetish, but it isn’t, it’s just a type of girl that I’m strongly attracted to. I may never date a genetic girl again.


    • Awesome, thanks for your comment Charlie, I’m glad you’ve found a loving partner.

      I think that our awareness on this subject as men is likely to be from the internet and it’s easy to write it off as just a fetish rather than a life option.

      I’m glad you see trans women as just another type of woman your attracted to, I think that’s a cool way to look at it, we all have our types.


  4. Captain Morgan says:

    Reading this felt like reading my own biography. Can’t believe I only just found this site. It feels so good to see proof you’re not the only person who feels this way. Thanks man for your honesty Simon, and everyone else. It’s good to know WE EXIST. See you all on the forums.


    • Really glad that helped buddy, it’s really why this site exists, I think guys like us fall into a grey area without much support, at least this gives you and others a sense of not being the only ones.


  5. As a 40 year old Trans woman who transitioned when I was 19, I found this story incredibly touching and thought provoking. It’s very easy to forget the issues that men who like Trans face. We need more resources like this. It’s a pity posting seems to have stopped. You’ve inspired me to look into this further. I’ve been looking for a way to make an appreciable difference to the next generation of Trans and I think this is a good area. I don’t want to see the next generation face the soul crushing and breathtaking loneliness that I’ve had to face. As far as our society has come, there is so much more that needs to be done.


  6. the dude says:

    Yeah I too agree with the lack of forum to talk about this issue. Judging by a lot of the porn out there. There has to be a large amount of men who are trans attracted… its terrible having to hide because of fear of people not understanding it. And thinking you are some kind of freak. We are the true supporters of trans women as we are the ones that are attracted to who they are. And if men were not ashamed they would proudly date trans women openly


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