How an anti-trans advocate ended up providing me a bottom surgeon

Over a meal in a European capital recently, I dined with a woman who is at the pinnacle of the financial world—she runs a prestigious firm, has hundreds of people working for her, handles billions of euros of investments, and is a phenomenally energetic and engaging person.  She is also a friend.  She and members of her family have also waded into the debate on transgender rights and feminism—made more impactful by her professional prominence.  These are some glimpses into our evening together.

In the past I have said I am nonbinary.  Also, that I didn’t know how far I would go on this journey towards the feminine.  My children have admonished me about surgery—in part out of concern for my health.  But in recent weeks a recognition that bottom surgery lies in my near future is a certainty that is settling in.  I wrote before that my closest friend sees ‘she’ in my future.  I do too, but I don’t say it.  It will be gift that unfolds for me (that is my hope).  Recently, another professional friend, who had already asked my pronouns once, said “she” of me, and then asked again and said, “sometimes your gestures and mannerisms, and often your way of thinking and expressing yourself is female, and ‘he’ doesn’t feel right, and it just came out ‘she’ just now.  I hope that’s all right.”

My male bits will be upcycled into female bits.

I can’t tell you the relief that provides me.  One of my male friends offered that as a tragedy—that I had the looks as a man, given my physical proportions, and he “speculated” as to my endowment…whilst flattered, I did tell him that it was already too late, and anyway, one can’t donate cxxk.  I do not lament how much smaller it has become and its apparent dormancy.

Coming out has been a process of unbridled joy

I’ve been gradually chipping away at the parts of my life where full disclosure has not happened and continue to receive universal support.  I am kind of blown away by how naturally and how quickly people have embraced me.  I told my boss at work, and he was so utterly supportive.

I was at a “school” reunion recently, catching up with people on the periphery of events, and despite having come out to many of my former classmates individually, nobody had said a word.  Nobody had gossiped.  I felt so respected by this.  And when I went to dinner with a number of them, my male classmates hugged me and kissed me European style.  I never expected to be received so warmly.  It took me completely by surprise, but to a person, they received me as I was presenting, and we didn’t need to talk about it.  Not a word.  It was completely organic.

I remarked this to my dinner date a few days later, another classmate and friend whom I had not seen in nearly 20 years, and she said something which I have posted about and been thinking, and which proved to be just one of many rich things she said to me over an evening.  She said, “you were never an asshole.  You were always a gentle person.  No mean words.  Everybody knows that.  Everybody remembers that.  So why shouldn’t they treat you this way now when what you need is support?”

Bless her.

An Encounter with An Anti-Trans Advocate

To be forewarned is to be forearmed.  I had been told by a very dear friend who is a mutual friend of my dinner date that my evening companion had strong views on the topic of transgender rights, and that I might find the conversation spicy.  In the end, I was left with a feeling of how friendship can transcend politics…and was really moved by her personal Damascene journey over our meal.

We explored everything, from trans women in politics, to bathroom use, to sports, to the essence of femininity and masculinity, when you become a woman and when you are not, gatekeeping, transgender rights, transvestites v transgender, the Balkanization within the LGBTQ “community”.  We also talked about divorce and the stigma of divorce in conservative society, particularly the one she lives in.

In the end it was seeing these issues through someone with whom she had a personal connection, someone she knew, liked, and respected who was without politics, that most moved her.  She shared stories of her own about a close friend whose “daughter” is now a son.  And how that happened at such an early age…something which she struggled to understand at first, but understood that for most trans people, the knowledge is there from the outset.

“Tell me about this,” she said.

“I’ve always known.”

“That you were female?”

“That I wished it more than anything.  I can remember going to bed at night, wanting to go to bed at night so that I could fall asleep hoping that in the morning I would wake up a girl, and how sad it was for me that every day my wish didn’t come true.  I wanted to a ballerina.  So badly.”

“but you weren’t happy to be a boy?”

“Not at all.  It has made me suicidal.”


“Yes, certainly in my early twenties, and also recently, maybe two or so years ago.  And I ran to the arms of therapy both times.”

“Why now?  Why not ten years ago?”

“I don’t want to die a man.  I am coming to retirement.  I can contemplate not needing to work anymore—only this divorce business is putting a crimp into things.  And it just started happening.”

“How did it start.”

“Just one day, I had been with a friend, and I looked in the mirror and what I saw was beautiful to me, and I thought, I’m not taking these clothes off.  And it wasn’t like I had lot’s of women’s clothes, or that I wore them in private all the time…not at all, but I had never been out in public before.  And that day I did.  And since that time, I almost didn’t stop.  I had one affirming experience after another.”

“That’s beautiful.”

I told her about some of them.

“And then, working with a therapist, I also did Ayahuasca, setting a very clear goal for the experience of “’etting her out’.”

“XXX [a good mutual friend of ours] has been very involved in Ayahuasca.

“Yes, I had heard.”

“I think he has done it a lot.”


“Too much.  I am not sure it is helping him.”

“That can happen.”

“So, tell me.”  And so I did, and how that played out will be another post, but it was instrumental in helping me to peel away any vestigial fear of letting go of my masculine self.

When I had finished she said, “that’s so beautiful.”

“It was amazing.”

“And how far will you go?”

“I don’t see an end point on this process.  I will also change my sex.  There will be a time when it will feel right, and that is going to come soon.  I don’t care if people look at me and see a man, I don’t care what pronouns people use, but I want to be liberated from my male anatomy.”

“One of my boyfriend’s best friends is one of the top transgender surgeons in the world.”

“You’re kidding.”

“Not at all.  He is an amazing person.  And my boyfriend has taken a keen interest in these issues since getting to know him.”

“Please make an introduction.  I am worried about finding a surgeon I can trust and want to know who it is well before.  It’s a big operation.  And there is lot’s of prep beforehand too.”

“It’s a huge operation.  Yes.  I will.”

There we have it…my research into bottom surgeons begins with a bang.  Thailand, Brazil, Europe, USA—so many theories, and then the apple falls at my feet.  You will know dear reader the credence I place in these things.  I do not believe that chance encounters are chance, or that conversations opens these doors by accident.  It was meant to be this way.  And whatever your journey in life is, listen to these faint signals, follow them, and you will find your life becoming increasingly effortless.

Sexuality and Touch and Differences Between Men and Women

I told her that although I have always been an emotional person, quite capable of crying, that now I just cry all of a sudden.  She shared about how she can cry for a day.  That it is very healthy and therapeutic.  

“When a man doesn’t know where he is going, he just keeps going.  A woman asks.  We are social.  We ask for help.  Men are simpler that way.  At times, I think, how easy and refreshing it would be…but then I realise how rich my life experience is,” she said.

“Its funny you say that, since I started taking estrogen I want to talk to everyone.  I talk to the person next to me on the train, I talk to my taxi driver, I talk to all kinds of people.  In my man days, I never talked to anyone.”

“You see,” she said, “we are social.  For many men, we are their only outlet.  My brothers have never told our mother that they love her.  My boyfriend and his best friend speak every day, but they never discuss any of their problems.  ‘Why not?’ I asked.  When I have a problem, I go onto a group chat with my girlfriends and announce, ‘I have a problem,’ and then we all start talking at once, and I never resolve my problem because nobody ever answers it, but I feel better because I feel like I’ve talked about it.”

“You know,” she continued, “you are getting the best of life.  To grow old as a woman is much better than to grow old as a man.  I see all these middle-aged men who just more and more want to watch TV, to stay home, never go out, and just start to die.  Women take hobbies, want to socialise, go out, go on trips, take courses, expand their lives and their minds.”

“Well, I’ve certainly been busy.”

“You see.”

“The best part of what is happening to me is that women see me as I feel, have always felt.  They look at me different.  They know I am safe, that I am not a predator, and that means they allow themselves to smile at me, to talk to me, to compliment me.”

“There are two kinds of men.  There are men that a woman looks at and sees in him something vulnerable and beautiful, and something that she wants to protect, to cuddle, to hold…and then there are the others we don’t care about.  You have always been the kind that a woman would want to hold and care for.”

“Gosh, thanks.”

“You are beautiful.  As a man, you have always been beautiful.  Now as a woman you will also be beautiful.  You would look good in anything.  And that feeling doesn’t change.  I look at you now and can imagine that women will react to you in this way even more strongly.”

“Wow.  I hope so.”

“Look at all the amazing people you are meeting.”

“That’s true.”

“That’s why.”

The Process of Coming Out

“My experiences coming out have been so positive, but I know for many trans people it can be awful.  Very traumatic.  Violent.  We get killed.  Beaten up.  Sexually assaulted.  Our existence scares people, offends people.  I feel very lucky.”

“You aren’t lucky.  You are who you are,” she said.  Very Buddha!

“What do you mean?”

“You don’t force yourself on anyone.  But you are also very present.  You are tall, even majestic looking, but you are quiet, you pass gently, there is an ease about you.  I feel calm sitting with you.  I think you walk into a room and people feel good, feel calm.”

“Thank you.”  There are so many changes in my everything that are coming about because of my chemical makeup, I feel a bit as if I must walk on eggshells.  I don’t mean that as if to say that I need to be careful, but rather, that it is forcing me to re-examine my values and to try to step closer to living them, embodying them.  One of the therapists I am seeing is really just focusing on this one thing with me, living in a state of Grace.  [Dear reader, you know who she is, and know why that no matter how weird she seems to get, she is right there with me every step of the way].

In skating on thin ice, our safety lies in our speed.

–Ralph Waldo Emerson

That is so true.  I feel the same way about being trans…that through embodying kindness and grace, I will stay safe, and maybe, if I am lucky, will touch people’s lives in a positive way.

We also talked about how we both find drag queens offensive to women.  I apologise to anyone out there who is a drag queen, but it is a kind of humour that has parallels to me to racist expressions in early American 20th century cultural history.  Cartoons.  Not for me.

Physical Changes

Trans people often say to take selfies every day so that you can see your progress.  I have not been religious about it, and I don’t really see progress, only I feel happy with my body and face in ways that I have never felt, and I don’t know if that is just chemicals.  Whatever it is, it feels wonderful.

My skin has come alive.  It is a giant erogenous zone now, and I can’t stop caressing it, and my craving for human touch is off the charts.  Not teasing touch, but gentle, sensual touch.  My own hands help enormously.  

My breasts are real.  They are small, perky little things.  They also hurt like hell.  My nipples especially are so sensitive.  They have grown in size, as have the aureoles, which have also darkened, and are in a near constant state of arousal.  The milk ducts are forming.  That is a sensitive process.

“My breasts hurt,” I said to my dinner companion.

“Oh, I remember that.”

“Especially my nipples.  They’re killing me.  And I can’t not wear a bra anymore, or some kind of top.  It is too much to just wear a shirt.”

“Gosh, you’re taking me back to puberty.”

“That’s what my doctor says it is like.  That I am experiencing female puberty.  My trans friends tells me that is why I am crying too, and that sooner or later it calms down.”

“I remember that, and believe me, it doesn’t calm down.”

“I must have banged my chest all the time when I was a boy, but it didn’t hurt, but now, Oh my goodness, it hurts so much to bang my breasts, or even to lean on something.  I have to change how I lie in bed, how I sleep.  I can’t lie on my stomach anymore.”

“Well it’s better for you to lie on your back.”

“I went running this morning and I forgot to wear a sports bra, and I had to hold my chest the whole time.”

“Now you begin to feel some of what it is like to be a woman.”


I showed her the bras that I had bought that afternoon.

“They’re so feminine,” she said.  It’s funny, I didn’t see them that way just that they looked and felt comfortable.

“Do you think so?”

“I think they will look good on you.  Do you have a hard time buying them?  How do you know your size?”

“I’ve been wearing lingerie my whole life…just not bras…that’s new, but I know my sizes.  I had a fitting anyway.”

“And they just help you?”

“I used to work in retail, and I remember the ladies from the lingerie department talking about “shifty” men coming around…and from them I learned to just be open about it.  So the sales lady came up and asked if she could help, and I said yes.”

“I told her I don’t like underwire, and anyway my breasts are still growing, and what did she have in my size—small cup, 85 cm.”

“And what did she say?”

“For you?  And I said, ‘yes’, and she just started showing me stuff and I was helping with what I liked and didn’t.”

“I’ll bet that you were the topic of conversation after.”


“Who was that gorgeous man?”


“He was shopping for himself.”

“What a disappointment.”

“They were intrigued.  I’ll bet.  I’ll bet they are wondering all about you.”

“That’s the best part of this whole thing.”


“The way women look at me.”


“Women don’t look at me as a threatening anymore.”

“I’m telling you, they just want to hold you.  Cuddle you.  And now, the way you look now, I think it will be even more.”

“That sounds nice.”

“Women are more complicated.”

“In a good way.”

“Yes, I think so.”


I had a beautiful evening, and it was very strange to find myself in agreement on so many levels with someone who is outspoken about transgender issues, and is “on the other side”…or at least has been.  But here she was meeting me and understanding, showing compassion, recognising how dangerous the bathroom issue is for a trans person, and understanding that it is impossible to see “intent” in someone.  She knows me, and would not question even a male-bodied version of me in a female space…and that realisation helped moved the needle for her.

I am not an advocate for men in women’s spaces, or even pushing it.  I am an advocate for women having the right to invite someone on the border into such spaces.  I never take it for granted.  One day, I won’t have a penis.  Though, as some deliciously articulate trans people who have come before me have said—we still have penis’s, we just turned them inside out!  And it is hideously complex.  When is it okay?

Some day, I hope that I have crossed a line that people simply see me as female.  I won’t begrudge someone who calls me male.  I will be grateful to those who accept my femininity.  When will I start using women’s bathrooms?  When my anatomy has changed.  But I also know transgender women who are legally women, who look like women, live like women, but who still have vestiges of their male past—and I would never begrudge them.  We suffer mightily…and I thank God that this suffering is not mine, but I feel it all around me.

This is very important for me to say.  I am having so much positive affirmations.  I don’t mean to repeat them to toot my horn.  I am flabbergasted.  And silly Christian expressions such as “what you give is what you get” seem so transactional.  Ex-Mistress spoke of the concept of quid pro quo as something which has no business between those we hold close.  That’s very convenient for me, whose kink is giving.

What we ate

As we talked, we ate a giant beefsteak tomato that had been blanched, peeled, lightly caramelised in a slow oven, cored, drizzled with olive oil, salt and wine vinegar, sprinkled with dried oregano, and served whole.  It was sensational.  We also ate artichokes which had been trimmed, blanched, and slow-boiled in oil, before being drained, flattened out like flowers into disks as wide as pineapple slices, and roasted in the oven until golden brown and slightly crispy.  

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