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Did Virginia Woolf write the first trans novel? She believed that the creative mind is androgynous

Credit: Orlando


November 20, 2023   8 mins

“Yesterday morning I was in despair
 I couldn’t screw a word from me; and at last dropped my head in my hands: dipped my pen in the ink, and wrote these words, as if automatically, on a clean sheet: Orlando: a Biography
 [I]t sprung upon me how I could revolutionise biography in a night
” — Virginia Woolf to Vita Sackville-West, 9 October 1927

It was playful and bold to write a novel as though it were a biography, and to call a fiction a life, and to invent that life around a woman the author was in love with, and to stretch her over 350 years, like a body freed from the problems of gravity. In Orlando (1928), Virginia Woolf did away with the usual co-ordinates of biography and set off through time as though it were an element, not a dimension.

The story is simple: Orlando is a young nobleman, aged 16, in the reign of Elizabeth I. After a series of adventures and disappointments in love and life and poetry, he takes an appointment as the British ambassador in Constantinople. Aged 30, he wakes up one morning from a week-long dead sleep to find that he is now a woman. Orlando returns to England and discovers that it changes as centuries pass but he, or rather she, continues as before. Woolf wrote the book at top speed, scarcely pausing, as Orlando scarcely pauses as he races through 350 years.

On 11 October 1928 — the last day in the novel — Orlando has reached the age of 36: “The true length of a person’s life, whatever the Dictionary of National Biography may say, is always a matter of dispute.” This is a poke at Woolf’s father, Sir Leslie Stephen, the great and erudite editor of the DNB. The Victorians loved dates and facts, especially dates and facts in order — theirs was the age of classification, of taxonomy, of the museum, the geographical society, the butterfly net. The pinned wings or the shot and stuffed head are symbols of Victorian England. The Dictionary of National Biography, where the great and the good could be safely pinned and stuffed, was, to Woolf, part of the monstrous edifice of the 19th century that 20th-century creativity needed to overthrow.

As Orlando enters the 19th century she notices, to her dismay, “widow’s weeds and bridal veils
 crystal palaces, bassinettes, military helmets, memorial wreaths, trousers, whiskers, wedding cakes, cannon, Christmas trees, telescopes, extinct monsters, globes, maps, elephants, and mathematical instruments”. In one of the funniest passages in the novel, Orlando suffers a kind of self-generated electric shock treatment as her left hand takes to convulsing spontaneously. She realises that it is because she is not wearing a wedding ring. She rushes out and finds a husband, and the symptom subsides — the censorious somatic symptom of an age where every woman must be classified as virgin, wife or widow.

And everyone as male or female. Woolf was born in 1882. She grew up as a Victorian. Gender roles were strictly observed in society and at her London home in Hyde Park Gate. Her brother Thoby went to Cambridge; Virginia and her sister Vanessa were educated at home. The social doctrine they were raised on was that of “separate spheres” — woman in the home, man in the world — and it was still going strong when Woolf published Orlando, in the year that all female British citizens over 21 finally got the vote.

But Woolf believed that the creative mind is androgynous. She was an expert in Elizabethan literature. She loved both the scope and the certainty of the Renaissance mind. Shakespeare, writing his sonnets to boys and women with equal passion, understanding the manliness of a soldier, the intensity of a nun, seemed to her to be a sign of what we all might be — bigger, wider, freed from convention and hypocrisy. Woolf met Vita Sackville-West in 1922. Sackville-West was an English aristocrat brought up at Knole House in Kent. As a woman, she could not inherit the ancestral home. Woolf, who had fallen in love with Sackville-West’s past as much as her person, found that the family portraits, ancient relics and priceless objects that filled Knole filled her imagination.

But Orlando is more than a fantasy or a historical novel; it is highly political. Orlando is a savage satire on sexism. When Orlando becomes a woman, his stately home and all her affairs are put in Chancery, because a woman cannot be a duke, and a woman cannot be an ambassador to the Turks, and a woman cannot inherit one of the finest houses in England. But a woman can cross-dress. Once Orlando becomes Lady Orlando, he must make his skirmishes across gender by dressing up. This she does frequently, in order to meet with life outside drawing-rooms and carriages. Sackville-West often dressed as a man and had affairs with other women in her disguise as “Julian”. She had an affair with Virginia Woolf as herself, and although both women were married the passion between them was real — this is clear from their letters. On Woolf’s side it was deeper while it lasted, because Woolf was deeper, and Sackville-West was an unrepentant flirt.

But whatever happened between them affected Woolf’s imagination as well as her heart. Orlando, written as a romp, a love letter, a gay book in every sense of the word, turned out to be the engine of an exploding freedom in her style. Writing Orlando did Woolf good. Begun as a gift to Sackville-West, it became a gift to herself. It is the most joyful of her books. Woolf’s mind was always first-rate, but when she came to write her next book, A Room of One’s Own (1929), she carried across the full-heartedness of Orlando. A Room of One’s Own is a masterpiece because it is more than a polemic; when she writes about women, about men, about the interplay of the mind, about creativity — above all, about writing — all her thoughts are steeped in feeling. The tract is much more than an argument; it is a passion for life as it could be lived.

Sackville-West, who was not a great writer or a deep thinker, and certainly not a faithful lover, released something in Woolf — something that had been pressing at the bars since Mrs Dalloway (1925). The quality of mind that Woolf (following Coleridge) called “androgyny” is really an adventure of the spirit (think Emily Dickinson). Sackville-West, for all her evening suits and ancestors, did not possess that quality of mind or that adventure of spirit, but she did have a full sexuality and a body to match. It is as though Sackville-West became Woolf’s blood supply for a while. Woolf was never a physical person; with Vita she found herself to be a woman — rather in the way that Orlando does. Sackville-West, all body, allowed Woolf to live in her own body.

It is an entertaining thought to remember that Orlando, all sex-change, cross-dressing and transgressive desire, appeared in the same year as Radclyffe Hall’s sapphic romance The Well of Loneliness. The two novels are different solar systems. The Well is gloomy, beaten, defensive, where women who love women have only suffering and misunderstanding in their lonely lives. The theme is as depressing as the writing, which is terrible. Orlando is a joyful and passionate declaration of love as life, regardless of gender. The Well was banned and declared obscene. Orlando became a bestseller. Woolf’s wit, her writing, her audacity, smuggled across the borders of propriety the most outrageous contraband. Many of the photographs included in the first edition of Orlando were of Sackville-West. I am still not sure how Woolf got away with all this, but she did. The exhilaration of the writing has a lot to do with it.

It is hard not to fall in love with this book. The writing has a lovely physicality to it. Woolf is always an exquisite detailer but in Orlando the writing is earthed differently. There is something unprotected, even as it is fully conscious. There is a smell of soil, a wave of bilge, the turf is spongy, the rooks hoarse. The unprotected feel of the writing is about speed and energy. Some of that energy is sexual:

“Flinging herself on the ground, she felt the bones of the tree running out like ribs from a spine this way and that beneath her. She liked to think that she was riding the back of the world. She liked to attach herself to something hard.”

When Woolf thought about writing she concluded that poets proceed by leaving everything out. The novelist proceeds by piling everything in. How could she both pile in and leave out? Orlando is more cluttered than any of her other novels. At the same time, because she is Virginia Woolf, this pell-mell fling of a book is anti-clutter, anti-collecting, and we find as we read that all these collectables are playthings and chimeras. She vanishes them away in an instant. Centuries pass, the rules of time are ignored, physical boundaries do not matter, even the shabby poet Nick Greene, who insulted Orlando as a young man, is met with again as a fashionable London critic of the Victorian age.

Woolf’s sense of this tremendous freedom of existence clusters in a moment near the end of the novel. The Lady Orlando is by the Serpentine watching the toy boats. She has lunched with Nick Greene. She has ordered books from a bookseller — a great novelty for one born in the age of ink-stained manuscripts. She stands at the water’s edge:

“It’s something useless, sudden, violent; something that costs a life; red, blue, purple; a spirit; a splash; like those hyacinths (she was passing a fine bed of them); free from taint, dependence, soilure of humanity or care for one’s kind; something rash, ridiculous
 ecstasy
”

And we are back with the boy Orlando racing through the rooms of his ancestral home, late for the great queen, sinking upon his knees under a hand “attached to an old body that smelt like a cupboard in which furs are kept in camphor”.

We live in a speeded-up world where is it difficult to find 40 minutes, let alone nearly 400 years. Yet, as Woolf observes, time is there for us if we know how to take it. Reading is one way of taking time. Reading takes time, but time is not lost that way, it is repurposed. We find time. Orlando refuses all constraints — historical, fantastical, metaphysical, sociological. Ageing is irrelevant. Gender is irrelevant. That last is especially interesting now, as the politics of non-binary identification are challenging categories of what is male, what is female, and whether or not biology should be destiny. Orlando grapples with sexism for sure — but makes it clear that while society regards Orlando very differently after her unexpected sex-change, Orlando themselves does not take that view. Immediately after the transformation, the newly formed Orlando gazes into the mirror “without any signs of discomposure” and calmly goes off for a bath, while Woolf addresses us directly:

“We may take advantage of this pause in the narrative to make certain statements. Orlando had become a woman – there is no denying it. But in every other respect, Orlando remained precisely as he had been. The change of sex, though it altered their future, did nothing whatever to alter their identity. Their faces remained, as their portraits prove, practically the same.”

Different sex. Same person. Orlando is not the first piece of fiction about sex change. Ovid’s Metamorphoses is an equally playful and serious treatise on the mutability of the human form. The Arabian Nights is stuffed with gender-switches and cross-dressing. Shakespeare’s comedies often pivot round a gender-disguise, and as no women were allowed on the Elizabethan stage, and female parts were played by boys, every romance is also a bromance. It’s likely that Woolf’s title is taken from As You Like It, where Rosalind, disguised as the shepherd Ganymede, teaches the man she loves — Orlando — how to love in return.

Still, Orlando is the first trans-novel. Except that Woolf was refusing all labels here. She called it a “biography”, knowing it was a novel. She started the postmodern fashion for mixing up fact and fiction, history and invention. We are used to all that now. Woolf was our pioneer. “Did you feel a sort of a tug, as if your neck was being broken on Saturday last at five minutes to one?” Virginia wrote to Vita on 20 March 1928. She sent her a copy on publication day, 11 October 1928. Their love affair was nearly over by then. Our love affair with Orlando, the boy who’s a girl who’s a girl who’s a boy, goes on and on.

***

This extract is taken from an introduction to the Everyman Classics Library edition of Orlando by Virginia Woolf. 


Jeanette Winterson CBE is the author of 13 novels, including the national bestseller Why Be Happy When You Could Be Normal? and Oranges Are Not the Only Fruit. Her introduction to the Everyman Classics Library edition of Orlando by Virginia Woolf is now published.

Wintersonworld

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John Lammi
John Lammi
7 months ago

No one is trans, of course.

George Scipio
George Scipio
7 months ago

Orlando is a bisexual fantasy romp, nothing more. No one has or ever will literally change sex. Like all apologists for postmodern chaos, Winterson confuses the map with the territory. Destiny is of course a false concept, like the “authentic self” of the transgenderist game players. The self cannot be separate from the body, except in fantasy. This is conclusively demonstrated by death.

Alan Jackson
Alan Jackson
7 months ago

Let’s pretend! . More, let’s pretend is what makes life exciting. No boundaries! Nothing fixed -except mortality! Woolf in the end drowned herself. Alas, a serious end to all that pretence!.

Sue Sims
Sue Sims
7 months ago
Reply to  Alan Jackson

Mr Jackson wins the Internet.

UnHerd Reader
UnHerd Reader
7 months ago
Reply to  Alan Jackson

Anyone who thinks they’re not pretending is either not thinking hard enough or pretending.
What is Alan Jackson? He might be the summation of a set of life experiences (quite a few judging by the picture) but the man who Alan Jackson believes himself to be has influenced his own interpretation of those life experiences.
Alan Jackson is incapable of being an objective observer of his own existence. He might have been born in a particular space, amongst a particular community, he might consider that his home. But in forming that judgment Alan Jackson will have selected and weighted certain experiences and aspects which he then internalised whilst ignoring others.
Was Alan Jackson using objective criteria when selecting and ignoring these experiences and aspects? Is he viewing them objectively when remembering now? Has Alan Jackson allowed future experiences to influence his interpretation of his part experiences?
Alan Jackson, like all of us, is an abstraction. Alan Jackson is and only ever can be what Alan Jackson pretends to be.
As Freud might have predicted, the anti-trans lot grasp their genitals as the sole objective fact in their existence. The only element of their being that has been inextricably true since birth.
Alan Jackson is confused – maybe he has been pretending? Who is the authentic Alan Jackson? He can hardly remember old friends, parents are only memories, the place of his birth is changing but he can say one thing for certain. Alan Jackson has his genitals and all else flows from there. Alan Jackson is a p*n*s.

Last edited 7 months ago by UnHerd Reader
Steve Murray
Steve Murray
7 months ago
Reply to  UnHerd Reader

All of that may be true, but at least he hasn’t drowned himself yet.

Martin Smith
Martin Smith
7 months ago
Reply to  UnHerd Reader

I don’t know anything about myself but I know that I am in the wrong body and must undergo genital mutilation otherwise I will kill myself, a victim of the cis white patriarchy.

starkbreath
starkbreath
7 months ago
Reply to  UnHerd Reader

Good God, what a load of post-modern drivel. The article wasn’t any better. For too many ‘intellectuals’ no idea can be stupid as long as you dress it up in the requisite amount of solipsistic dross. For the rest of us, bullshit’s bullshit.

Martin Smith
Martin Smith
7 months ago

Androgyny and trans are not the same. Trans women/men are women/men apparantly…

John Lammi
John Lammi
7 months ago
Reply to  Martin Smith

Androgyny is not a mental disorder

carl taylor
carl taylor
7 months ago
Reply to  Martin Smith

And ‘non-binary’ doesn’t exist.

Ewen Mac
Ewen Mac
7 months ago

What do you mean by “trans?”
It currently means several entirely-different things including: Transexual, Transvestite, ‘Suffering from gender dysphoria,’ or ‘Trying to get a reduced sentence in a women’s prison.’

Last edited 7 months ago by Ewen Mac
J Bryant
J Bryant
8 months ago

I enjoyed this article at least for the quotes from Orlando. The term “genius” is bandied about too freely, but I believe Woolf was a genius. Her prose is all rhythm and cadence, breathlessly taking us from one time or place to another with no clear memory of how the transition was made. I would hate to “critique” a Woolf novel; I’d hate to rationalize the magic.
She wrote a very short story (what would now be called flash fiction) called “A Haunted House” which is one of the most original contributions to the horror genre I’ve read, and yet it is a century old and probably isn’t really a horror story. It’s easily googled if you’re interested.

Margaret Ford
Margaret Ford
7 months ago

please don’t call one of my favorite books a ‘trans-novel’. Why does this new ideology have to invade my imagination and history as well as everything else? Can’t we just accept that some sensitive writers women and men have always imagined life as the other without attaching ideological labels that impose imaginative limits?

Shrunken Genepool
Shrunken Genepool
7 months ago

Bla bla bla. Enough already. There is no such thing as ‘trans’. A genuine mental illness (dysphoria) and a much larger process of social contagion egged on by activist teachers. VW has nothing to offer our world. She never did. JW neither – part of the problem

Steve Murray
Steve Murray
7 months ago

I’d suggest they do have something to offer – an insight into a particular mindset – (of which i’m making no particular judgement with this comment) that is, however, something very human; and i’m very much interested in that, as we all should be. It needs to be more fully understood rather than dismissed.

Allison Barrows
Allison Barrows
7 months ago

Who gives a flying? This fad will fade away, like they all do. The huge and tragic difference is that it will have created countless permanently disfigured patients for the medical monsters to milk, and plenty if lucrative law suits for lawyers.

Theresa Guirato
Theresa Guirato
7 months ago

The brain is not androgenous… it is genderless.
So NO, Orlando was NOT the first trans novel.

Benedict Waterson
Benedict Waterson
7 months ago

If gender is so mutable and challenging it so transgressive then why go to all the trouble of full body plastic surgery to achieve a supposedly literal and fixed sex identity?

Carmel Shortall
Carmel Shortall
7 months ago

Unherd has now reached peak Guardian. I’m off to Substack…

Charles Stanhope
Charles Stanhope
7 months ago

You can’t be serious? It’s full of brain dead American poseurs.

starkbreath
starkbreath
7 months ago

Instead of throwing fellow anti woke writer/journalists such as Matt Taibii, Michael Schellenberger and Bari Weiss under the bus, why not accept them as allies? Those of us who despise the far left need to hang together, otherwise we shall hang separately.

Aphrodite Rises
Aphrodite Rises
7 months ago

The title of the article sounds like a question addressed in a woke PhD thesis. Jeanette Winterson lectures in the Oxford English department which produced Cathy Newman who exposed the progressive Oxford mentality in the Jordan Peterson interview. I really enjoyed both of Jeanette Winterson’s autobiographies, I thought they were brilliant, but not her other writing: I got the sense she was trying too hard to be a great writer. It put me in mind of an interview with Salman Rushdie I once read. He said when he first tried to write, his writing was not well received and he was advised to write what he knew. He sat down and wrote Midnight’s Children – pure brilliance.

UnHerd Reader
UnHerd Reader
7 months ago

Amazing. “don’t like title. saw something on youtube loosely related to writer which I didn’t like… must be bad”

Aphrodite Rises
Aphrodite Rises
7 months ago
Reply to  UnHerd Reader

Are you projecting? I have read a great deal about the writer and many of her novels. I have never seen anything about her on YouTube. I was going to criticise the article in detail but I couldn’t be bothered repeating myself again.

Charles Stanhope
Charles Stanhope
7 months ago

Agreed.

Susan Scheid
Susan Scheid
7 months ago

Answer: no, she did not.

Mathilda Eklund
Mathilda Eklund
7 months ago

Remember being absolutely bewildered and so sad finding out Winterson had fallen for the gender propaganda. One of my favourite authors of all times. Gut Symmetries is a masterpiece.

Christina
Christina
7 months ago

My first thought upon seeing who the author of this article was, was “oh no not Jeanette Winterston too”
I don’t understand how intelligent people are rewriting every unconventional women in history as trans.
And this book which was obviously a feminist book and not a trans one.

Dulle Griet
Dulle Griet
6 months ago

I admire the beauty and originality of Jeanette Winterson’s prose, and the empathy and insight with which she writes about Virginia Woolf. But no, Orlando was not the first trans novel, because Orlando literally changes sex – which transgender people don’t do because it’s biologically impossible.