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TG History — Forced Crossdressing

| Jul 7, 2008
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Michelle Moore brings you TG History“You can’t make me!”

There’s probably nothing in transgendered folklore that’s as provocative as the concept of forced crossdressing, especially stories about raising a young boy as a girl. On one hand, it’s a crossdressing fantasy that’s as old as, well, crossdressing. On the other hand, anything involving with the raising of children has to be considered carefully. You need only look at Dr. Renee Richards’ autobiography, which recounts in unflinching detail her own forced crossdressing at the hands of her mother and sister. It’s not a pretty story, though, but a pattern of abuse that led Dr. Richards to question to this day what effect it may’ve had on her decision to transition. With that cautionary note in mind let’s take a look at some historic accounts of forced crossdressing.

Forced transformation novels first appeared in Europe at the very end of the 19th century. Set in the sexually repressed Victorian era, these fictional stories first introduced the now familiar themes of “corset training” and “petticoat punishment.” The plot usually revolved around a domineering aunt, governess, or other female authority figure who would first lavishly dresses up some unruly young male then thoroughly turns him into a beautiful, demure young lady. Of course in those stories the young male usually goes on to discover he actually likes being a girl and all ends happily ever after. But these were just fantasy stories – things like that never happened in real life. Or did they?

The De Lessup family.Let’s consider the possibilities for a moment. Dressing up young boys in girls clothing was actually a commonly accepted practice in both America and Europe. In America from the 18th century through the early 20th century, young boys routinely wore the dresses, skirts, pinafores, and even had the same hairstyles of their young sisters. Afterwards in a process called “breeching” boys were finally allowed to wear trousers, signaling their assent into eventual manhood. Yet when this decision was finally made varied from household to household and young boys typically remained in dresses and skirts up to ages 6-8, depending on the era. But consider – today we now believe that a child imprints his gender identity as early as age 2 or by 3 at the latest. Also in those days a boy was raised at home in an almost exclusively feminine environment by either his mother or a female relative or servant. Now suppose — just suppose — that she would really, really prefer to have a little girl instead. It certainly would’ve been easier than today to dress up and feminize him – whether he liked it or not. Let’s take a look at four different instances during Victorian times when this actually happened.


Tommy“I kept him the baby,” his mother reportedly bragged about her youngest son. And so she did, keeping him dressed up in baby girl clothes well past infancy and continually fussing over his appearance. This was at a time when boys were starting to be educated in public schools rather than at home so mothers weren’t as inclined to dress their boys in fanciful styles. But that didn’t stop Tommy’s mother. Tommy was forced to wear a series of frilly dresses and precious lacy outfits well past age 6. As he became older and his mother was required to present him in public as a boy she introduced him to the dreaded, long out-of-style Lord Fauntleroy suit. Frilly Lord Fauntleroy outfits sometimes consisted of dresses with lace collars or were fitted with Fauntleroy blouses and jackets with a kilt-skirt rather than kneepants. Perhaps worst of all for Tommy was his mother’s constant fascination with his hair. She would lovingly style his hair each and every day into long, elegant ringlets or sausage curls. When he began attending school looking so unabashedly feminine his classmates continually accused him of really being a girl.


His doting mother affectionately foisted the nickname “Bertie” on him and forced him to wear a succession of femininely styled dresses and skirts well past the age this was considered to be socially acceptable. His mother also worried incessantly about his smooth, creamy complexion and forced him to wear a sunbonnet whenever he went outside. As a youngster he was made to learn lace making, embroidery, and other feminine handicrafts normally taught to proper young ladies. By the time he was old enough for school he displayed distinctly effeminate mannerisms and spoke with a very pronounced lisp.


Who’s that girl?Just as it’s common today to dress twins alike so it was common in Victorian times to dress a twin boy and girl alike. But it can be said their mother, Grace, really went to extremes. She really wanted twins and was very disappointed when her son was born a year after her daughter Marcelline. So Grace decided to raise them both as twin girls, even holding Marcelline back from the first grade so that the two of them were always together. Grace liked dressing the boy and his older sister in matching girlish outfits so they looked as much alike as possible. He was made to wear an assortment of ruffled skirts, pink gingham gowns, fluffy lace dresses, black patent leather Mary Jane shoes, and high stockings, usually accessorized with either crocheted bonnets or large flowery hats.

A hairstyle sometimes seen on little boys of that era was called the Dutch Dolly. In a highly feminized version of this style Grace would cut his yellow hair into a square bob with big curls over his ears and long girlish bangs. She enduringly referred to him as her “sweet Dutch Dolly.” He soon began wondering out loud how Santa Claus would ever know that he was really a boy. But perhaps most telling is a famous photograph showing him at age two clad in a dainty white dress and wearing a big flowered hat. At the bottom of the photo his mother wrote the caption “Summer Girl.”


This boy spent the first eight years of his life dressed as a girl. His mother would doll him up in adorable dresses with lace trimming and big colorful bows or in long flowing skirts. These outfits usually were topped off with pretty feathered hats or occasionally bonnets. His long hair was elegantly coifed with bouncy feminine curls – a hairstyle that he was forced to wear until puberty. He began to display a great personal vanity and developed a love for costumes and finery, causing his classmates to nickname him “Sarah” after the actress Sarah Bernhardt.

Now admit it — any one of these stories sounds like it leapt right off the pages of a “forced crossdressing” Victorian novel. But did any of these boys actually grow up to be transgendered? Not really.

“Tommy” got so sick and tired of his classmates calling him a girl that he pulled down his pants to prove they were wrong. It wasn’t until nearly the age of 9 and after much begging that his girlish curls where finally cut off – and only then because he’d been infected by head lice. As you might expect this quiet, shy, sensitive boy grew into a quiet, shy, sensitive young man. When he decided to become a writer he basically became his own therapist by telling fictionalized accounts of his own life. His world famous novels including Look Homeward, Angel and You Can’t Go Home Again also dealt with shy, sensitive, intelligent young men growing up and coming of age in small Southern towns. Today, Thomas Wolfe is considered one of the 20th century’s greatest writers and he did it by writing about what he knew best — himself.

“Bertie” took considerable abuse and received quite a few thrashings from class bullies due to his effeminacy. He would eventually suppress his lisp by learning to speak in a slow, deliberate, and determined manner. It’s generally accepted that all this contributed to his growing up to be such a tough, obsessively driven man who could endure great personal hardship under even the worst of conditions. He joined the U.S. Navy Civil Engineering Corps but became world famous as an arctic explorer – each time going further and further north then anyone had ever dared go before. Finally on April 6th, 1909 after steadily inching forward through brutal arctic terrain, 52 year old Robert Peary along with his assistant Matthew Henson and four Eskimos stood where no one had ever stood before – literally on top of the world. After a lengthy investigation the United States Congress in 1911 officially recognized Robert Edwin Peary as being the first man to ever reach the North Pole. Following his death on February 20, 1920, Robert Peary was buried in Arlington National Cemetery with full military honors. Peary’s gravesite includes the inscription of his personal motto: Inveniam Viam Aut Facium – “I shall find a way or make one”

“Dutch Dolly” – The Summer Girl – grew into adulthood with a bitter lifelong hatred of his mother. Utterly embarrassed by his past, he embraced instead the life of the rugged outdoorsman. Soldier, adventurer, sportsman, bullfighter – you name it, he was all that – a man’s man, the Hemingway man. But it was as a writer that he acquired his worldwide fame, telling finely crafted, gripping stories of war, adventure, and other trials of manhood. He left the Summer Girl far, far behind and became known instead as “Papa.” And later in life when faced with lingering illness and depression he dealt with that too in the way he felt a man should – with a final, self inflicted shotgun blast. That was Earnest Hemingway.

“Sarah” — unlike Hemingway — grew up utterly devoted to his mother and it could be fairly said that he was a “mama’s boy.” But no one ever dared say that to his face. Because far from turning into a sissy, Sarah’s love of costumes and presentations was translated instead into a lifelong love for military uniforms and pageantry. Fiercely ambitious and driven, he would go on to a military career of unrivaled distinction while his emotional theatrics developed into a personal charisma that made him a dynamic leader of men – millions of men. Flamboyant and willful, his brilliant military campaigns led the Allies to victory over Japan in World War II while his vanity led the world to the brink of nuclear war in Korea. He was General Douglas MacArthur.


Thomas Wolfe: An Illustrated Biography, Ted Mitchell
Thomas Wolfe: A Biography, Andrew Turnbull
Ernest, Peter Buckley
Hemingway: Life & Work, Kenneth Schuyler Lynn
Peary, the Explorer and the Man: Based on His Personal Papers, John Edward Weems
Arlington National Cemetery – Robert Edwin Peary entry
Douglas MacArthur, Clark Lee and Richard Henschel
Vested Interests, Marjorie Garber
Who?, Erin McHugh
New Gay Book of Lists, Leigh Rutledge
Historic Clothing Website

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Category: Transgender History


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  1. Michelle Michelle says:

    Cena – Thanks. One thing you get from their bios is that these guys really got some conflicted gender messages early on. But they weren’t alone and I could have used other examples. Some mothers just wouldn’t let go and even after switching them to boyish clothes they kept a girlish hairstyle going for as long as they possibly could. Take Mickey, for instance – Mickey’s mom wanted a girl and his girlish Buster Brown hairdo got him more than a few poundings by class bullies. Maybe that’s why Mickey Spillane went on to create the hardboiled detective Mike Hammer. Then there’s Moses Harry Horwitz – his mother put him in dresses early on then continued keeping his locks long. When he couldn’t stand being teased any longer he cut it himself using a mixing bowl as a guide. Of course that “puddin’ bowl” haircut became the signature look for “Head Stooge” Moe Howard. It also might explain his constant PO’d attitude.

  2. Michelle Michelle says:

    Wolfram – For now how about an “un-forced transition” story instead? The story of a boy raised as a girl who not only enjoyed it but built an amazing life of adventure around it? Tune in next month.

  3. cena cena says:

    Another wonderful article, as usual Michelle! Too bad you couldn’t come up with the other two photos. I read somewhere that Hemmingway did dabble a bit with role reversal in marriage but it never got fully explained. MacArthur and Peary were real surprises!
    Cena Williams

  4. says:

    Great article and very well researched. I couldn’t guess any of them and was expecting more modern stories.

    Do you plan a later article on “forced transition”? Parents who for one reason or another decide to transition the child while still at an early age? I know there have been some occurances and they haven’t had good endings.

    I saw this on a cable channel one night.

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