I am a transgender woman and I want to have it all


While life seems to gyrate between a series of highs and lows, mostly occasioned by the changes that are wrought by oestrogen (on the upside) and my divorce (on the downside), I don’t think I have ever been happier or more carefree in my life.

I am a transgender woman.  I don’t doubt it anymore.  That means an expectation for people to take me as I am, and not give me bullshit about having to “ease them in slowly” to my transition.  Why should I?  It is their problem.  I won’t let it be mine.

I live in Italy.  People stare at me.  I mean, really stare.  Someone walking with me in London recently asked me if it bothered me that people were staring at me.  I hadn’t really noticed.  People look.  That’s not staring.  And every now and again, a really beautiful woman sees me, looks me in the eye, and smiles a deep and wide smile.  For that I would crawl across cut glass.

But in Italy, they actually stare.  I mean really stare.  Rude like.  Too long.  So now, I stare back, and sometimes I make faces at them.  After all, didn’t their parents teach them it is impolite to stare?  Of course the world has descended from civility to a new barbarism in human interaction, but Italy?!  This is one of the last bastions of gentility.  Come on people.

What I discussed with my Reflexologist is a diagnosis of this situation.  The benchmark is Spain, where I have been working lately, and have been very out in public.  Okay, this has been in Madrid in the main, one of the most LGBTQ-friendly places in the world, but this has been true in many smaller cities as well.  The only people that seem to “look” at me as an object are tourists.  Spaniards just live and let live.  And the men have been unfailingly polite—courteous, holding doors.

I was puzzled by this because Spain is one of the most macho countries in the world.  And we often associate machismo with insecurity.  But that is clearly not going on.  These men are very secure in their masculinity and seem to have no issue with gendering me as I present.  Good lads.  I found the same in South America.  In Lima, in Buenos Aires (Argentina was the first country in the world to offer “non-binary” as a gender marker in the passport), I have not even felt for a moment any weirdness.

But in Italy, in my cherished, adopted home, I get this.  Small towns are one thing, but the Milanese can do better.  I will keep trying.

What’s the diagnosis? Italians are conformists. They travel together, even bringing their own food. They dress with the fashion. And every evening, on the passeggiata, they check each other out. As in Asian cultures, the concept of “face” exists in Italy. So, when they are staring at me, some version of this is playing out. That’s all I can figure.

One of my closest Italian friends, close to both sides of the divorce, took great pains to say that they would “be there” for me, that our friendship was more important, blah, blah, blah.  I appreciated the words, but I could feel that it was a struggle for them, and that they were fighting against their own nature and experience.  I still called them again and asked them out.  Here is one instance where I am slow-pedalling on the clothes, though my tinted lashes and eyebrows are pretty hard not to notice.

But I went out for a drink with the male half of the couple the other day, and for the first time in a very long time, he insisted on paying.  I guess there is a silver lining.  I kind of like being regarded as vulnerable.  And in reality, I am.  Not because of being female trending, or of being trans, even though these are the markers they are reacting to.  No, it is a result of being more open.  Stepping into myself.  Stepping into the world.  

Italy.  So special and so contradictory.  At the check-in desk at the airport the woman said, “your famous aren’t you.  I know you.”  Even though my name is not famous, they continue to assume I am a movie star.  Is this their way of processing my fabulous dress sense?  I was wearing a short wool felt skirt, brown cashmere stockings, dusty chocolate suede high heeled boots, a wide matching belt sitting on my hips, a cream-coloured blouse with lacy sleeves which was naturally open far enough to show my bra, and a fitted black cashmere overcoat.  Plus I had a lot of luggage—as always.

But it can’t be the clothes, because I used to get this via my kids when I did the school run for them in my bathrobe. I guess “normal” people don’t drive their children to school in their bathrobes. I call that a last-minute function of ADD.

And yet, despite the get-up, everyone still calls me, “sir”.  What’s not to like?  The only makeup I wear is of the semi-permanent variety—coloured brows and lashes, which took some getting use to, but have now settled in…I don’t pass, shan’t pass, but don’t care.  I look good this way, I feel good this way, and if they want to call me ‘sir’, let them.  I don’t think I will care after I have had the anatomical solution I am planning and looking forward to since I was a little boy.

I was reminded of this the other day when a woman was man-handling me and she pressed her crotch hard against my posterior, and I could only think about how badly I look forward to having a clean crotch.

We are told that in order to love others, we must first love ourselves.  And that has always sounded like mumbo jumbo, and also an impossible task.  And anyway, who is the first person to betray oneself but the self?  

What I am learning is that loving the self is just the same as loving someone else.  They hurt you.  They betray you.  After all, they are only human.  We can’t help it.  And being vulnerable and open to that, especially in relation to the self, is exactly what it takes to love oneself.

Some amazing things have been happening to me lately on the personal front, within the sphere of “vanilla” love interests, but also with SWs and friendship, and on the work front.  So many irons in the fire that the sense of abundance is blowing me away.  My best friend tells me that the universe is taking care of me.  It sure feels like it.

What else?  I have a massive crush on my lawyer.  She is everything I look for and admire in a woman.  Professionally accomplished.  Focussed and hard-working.  Independent.  Strong-willed and outspoken.  Hilarious.  These were the things that my wife was when we first married, and which I sincerely hope she finds again inside—though she has the air about her of a beach-side restaurant in Le Touquet all shut up for the winter—awning drawn in, chairs and tables stacked and locked away…

The other thing about my lawyer is that she vibrates at a higher energy level than anyone I can remember meeting for a very, very long time.  Guru level.  Much higher than me.  And I can’t believe I am saying that about a lawyer, a professional class I have not had much good to say about over the years.  When people push you to be the best version of yourself, to stand taller, they are keepers.  She is a deep cheerleader for me on this path of transition, encouraging me to take no prisoners, to just be.  It is so utterly refreshing.

Besides those reasons, she is my knight in shining armour.  She is protecting me.  And that matters, because I suck at protecting myself for the particular kind of dynamic in relationships that divorce entails.  I can’t even stop using terms of endearment towards my wife.  I am mad at her and betrayed by her, and could never open my heart to her again, but I still love her and wish her well.  Apart from being disappointed in her for the betrayal—whatever happened with “in sickness and in health” and “until death do us part?”—the counter-balance is much stronger: what a pity for her to experience these feelings.

Oh, and yes, the physical changes are showing.  Naked me is unmistakably different.  My skin has changed.  It is softer and the pores have tightened.  The hair on my body, always sparse, is not so soft as to be nearly invisible.  My hairline, the one on my hand, appears to be moving forward again, and my hair is most definitely softer and thicker.  I also have that fuzz that women get at their hairline, a little detail which I have always loved.  I think my hair colour is also changing, becoming darker, and also more varied.

But most of all, it is no longer possible to deny the existence of my breasts.  Even when I’m in drag, what I call it when I am rocking boy-mode, as I do when I put on a men’s business suit, if I take my jacket off, the boobs are obvious.  My shirt tents quite dramatically—they are actually rather perky little things…and I noticed this morning that I have that crease, the seam in the skin under the boob that speaks to volume.  They are small, but they will be growing for the next 5 years, so I guess they will find their way to the right size.

And for the first time in my life, quite literally, I am not ashamed of my naked body.  Imagine that.  Life is now punctuated by the very rare times that I have to go into stealth mode, moments which are fast shrinking in frequency.

I don’t really know what will happen to me professionally, but I refuse to let fear of the unknown stand in my way.  Okay, therapy helps.  So too do meditation retreats.  And so too do a small number of SWs who I can actually regard as friends.  So what if I pay them?  As one enlightened SW said to me, “why would I want to play with someone who isn’t a friend?”  Now that’s enlightenment.

10 thoughts

  1. I love hearing that you are very happy, despite the difficulties of divorce. I was surprised to read about the judgmental looks you’ve been facing in Italy. I am glad your experience has been better in other countries though. Please continue posting, my friend… I love following your journey! Best wishes to you XOXO

    Liked by 2 people

    1. Hi. Divorce in the end will be a relief. I took my vows seriously. Had she cheated on me, I would have stayed by her. I could never have been the one to leave…or even be said to be the one who wanted to leave. But now that it is happening I feel so light and free. You don’t realise the burden of expectation the wrong partner places on you. I only realise now after 20 years of marriage that it was all about her, always all about her. That’s not a partnership. Its not even good slavery…because at least for the slave, you can enjoy what the Mistress enjoys from your work.

      Liked by 3 people

    1. Thank you for joining in. I hear you. But what choice is there? Why should our existence be our problem? We have enough to deal with as it is. I think we are beautiful. We possess so much as trans people by not fully belong to either camp and yet having so much lived experience that is common to each. You needn’t be anyone but yourself. You are enough and your lived experience, both good and good (because what doesn’t kill us makes us strong) is delicious. Savour it, love it, love you.

      Liked by 3 people

  2. This is so good! I’m so ready to begin transitioning! I’m finally accepting myself. My body and mind deserve it after dealing with anxiety and depression for so long. I love how your lawyer friend is supporting you. Have a fabulous week hon!

    Liked by 2 people

    1. Thanks so much. And sorry it took so long to come back to you, but for some reason this comment ended up in the spam folder. Thanks for chiming in. There was a moment where I realised that I didn’t care anymore, that I had to do it. And once the decision was made, I did it. And when I felt weak, or unable to face the stares, because that happens, I stepped into it even harder…I demand acceptance. And finally, one day I woke up after a few months of GAHT and realised, I am not a man anymore. I may not look female, but I sure feel it, and that’s enough for me.

      Liked by 3 people

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