Throught history transgender, transsexual, and crossdressing women have served in the military. Sometimes this was done by women who simply wore men's clothes so they could serve and have a military career. Most of these women lived as women before the war, and resumed living as women after the war. Sometimes this was done because the woman truly identified with the opposite gender, and truly was transgendered, living their life as a man both before and after serving. No matter the reason though, their true birth gender was always hidden while serving. 

Below is a brief timeline outlining some important dates regarding transgenderism in the military:

In the mid 1700's many female to male transvestites joined Nelson's Navy, and were only discovered when they were "flogged". Once discovered, they were never punished. They often went on stage and became celebrities wowing audiences backed by an all singing and all dancing group of transvestite stars.

Female-to-male transgender man, Jan Van Ant, enlists in the dutch army as a man in 1746. In 1748, Van Ant marries his sergeant's daughter, Johanna Cramers. In 1751 he is recognized by a former employer and put on trial for making a mockery of marriage and by entering an illegal marriage (for marrying a woman), and sentenced to exile from all garrison cities.

One notable female to male crossdressing sailor who served in Nelson's Navy was James Gray, who served as a navy marine until 1750. Gray was born Alice Hannah Snell in 1723, the daughter of Samuel Snell, a Worcester hosier and dyer, and Mary Williams, his second wife.

After the birth and subsequent death of her child, Snell borrowed a suit of clothes from James Gray, her carpenter brother-in-law, and travelled first to London and then to Coventry where she was pressed, under Gray’s name, into General Guise's Regiment of Foot in 1746.

Gray finished with his tour of duty in 1750, without his birth gender ever being discovered. 

Tales of Snell’s exploits quickly spread throughout the country and were even published in print. She took to appearing on stage, at the London theatres. Dressed in uniform as a soldier or a marine, she would go through her old drill-motions and sing appropriate ballads. In 1751, she even went on tour to Bath and Bristol, and it may have been at this time that Hannah became acquainted with the town of Newbury. In the meantime, the Duke of Cumberland was successfully petitioned to place her name on the military pension list and her battle-wounds led to her receiving an annuity as a Chelsea cut-pensioner. Never one to look a gift horse in the mouth, Hannah took on a public-house in Wapping, naming it ‘The Female Warrior.’ The pub sign represented her in regimental dress on one side and marine uniform on the other, with the inscription ‘The Widow in Masquerade’.

By the mid-1750s, Snell was probably living in Newbury in Berkshire and, on November 3rd, 1759, she married, for a second time, in St. Nicholas’ Church, to a journeyman carpenter named Samuel Eyles. Snell was heavily pregnant at the time, and a son, George Spence, was born soon afterward. A second son, Thomas, followed four years later. Upon Samuel’s death, she remarried again in 1772, to Richard Habgood of Welford, at the chapel in nearby Wickham.

In 1792, Gray is admitted to Bedlam Hospital after showing symptoms of insanity. Gray dies shortly after at the age of 69. Gray was buried among the old soldiers at Chelsea Hospital as she had always wanted.

19-year old female-to-male cross-dresser, Arthur Douglas, served on board the British Royal Navy’s “Resolution” in 1757 from January-May. 

Another notable transgender sailor who served in Nelson's Navy was William Chandler. William Chandler (born Mary Lacy, cirka 1740, dead after 1773), was a British sailor and shipwright. Chandler ran away from home dressed as a boy at the age of nineteen in 1759, and worked as a servant for a ships carpenter of the British navy until 1763. He then studied as an apprentice to be a shipwright. In 1770. In 1771, Chandler was forced to stop working due to rheumatism, and applied for a pension from the admiralty under his legal name, Mary Lacy, which was granted. As Lacy, She published her memoirs "The Female Shipwright" in 1773.  Chandler/Lacy's life after 1773 is unknown. 

Female-to-Male cross-dresser, John Meace (Born Joan Meace), enlists in the British Marines in 1762. John’s true birth identity is quickly discovered.

In 1781, naval seaman George Thompson revealed that he was female after being sentenced to be flogged.

Male-to-female transgender soldiar, Robert Shirtliff, joines the American army on May 20th, 1782. Shirtliff was honorably discharged from the U.S. Army’s Massachusetts Regiment At West Point on October 25th, 1793 after it was discovered that he was biologically female. Shirtliff had passed as a man for almost 1 1/2 years and formed attachments with several women.  

Female-to-Male cross-dresser, John Taylor (born Mary Anne Talbot) was enlisted as a foot-boy in 1792 and served as a drummer-boy in the battle for Valenciennes. Taylor later deserted and became a cabin-boy for a French ship. When the British captured the ship she was transferred to the HMS Brunswick in Portsmouth, England where he served as a powder monkey.  

In June 1794, Taylor was wounded for the second time when grapeshot almost severed his leg during the battle of the Glorious First against the French fleet. Taylor never recovered the full use of his leg but later rejoined the crew. He went ashore at St. Katharine’s Dock and, upon being approached by a press gang, revealed his true birth gender. 

Female-to-Male cross-dresser, John Bowden (Born Elizabeth Bowden), enlists in the British Royal Navy in 1806 and serves aboard the HMS Hazard out of Plymouth. Within 6 weeks of his serving on the ship, his birth gender is discovered.  

21-year old female-to-male cross-dresser, William Brown, enlisted in the British Royal Navy and joined the crew of the Queen Charlotte as a Landsman on May 23rd, 1815. Brown was forced to leave the Nelson's Navy In 1816 after being “outed” by a newspaper. Brown, who’s birth name is unknown, was reputed to be a Black man who was born female.

During the American Civil War (1861–1865) at least 240 biological women are known to have worn men's clothing and fought as soldiers. Some of them were transgender and continued to live as men throughout their lives. 

During the American Civil War (1861–1865) Sarah Emma Edmonds (born Edmonson or Edmondson) enlisted in the Michigan volunteer infantry company as Franklin Thompson in 1861. Edmonds successfully evading detection as a woman for a year. During her duty she participated in the Battle of Blackburn's Ford, First Bull Run / Manassas, the Peninsular Campaign, Antietam, and Fredericksburg. Sarah Edmonds sometimes served as a spy, "disguised" as a woman (Bridget O'Shea) or as a black man. After deserting, she worked as a nurse for the U.S. Christian Commission. Edmonds published her version of her service in 1865 as a Nurse and Spy in the Union Army. In 1882 she began to petition for a pension as a veteran, and was granted one in 1884 under her new married name, Sarah E. Seelye. 

Another such notable soldier who fought in the American Civil war was Albert Cashier.  Albert D. J. Cashier (December 25, 1843 – October 10, 1915), born Jennie Irene Hodgers, was an Irish-born immigrant who served as a male soldier in the Union Army during the American Civil War. Jennie Irene Hodgers was born female, but lived as a man named Albert D. J. Cashier. Cashier was born in Clogherhead, County Louth, Ireland. According to later investigation by the administrator of her estate, she was the child of Sallie and Patrick Hodgers. Cashier's later accounts of how she moved to the United States and why she enlisted were taken when she was elderly and disoriented, and are thus contradictory. By 1862, Cashier was living in Belvidere, Illinois.

On August 6, 1862, she enlisted into the 95th Illinois Infantry using the name Albert Cashier and was assigned to Company G. The regiment was part of the Army of the Tennessee under Ulysses S. Grant and fought in approximately forty battles,[3] including the siege at Vicksburg, the Red River Campaign and the combat at Guntown, Mississippi, where they suffered heavy casualties.

Other soldiers thought that Cashier was small and preferred to be alone, which was not uncommon. She was once captured in battle, but escaped back to Union lines after overpowering a prison guard. Cashier fought with the regiment through the war until August 17, 1865, when all the soldiers were mustered in and out.

A transcription from a letter written by Thomas Hannah, Jr., a private in Company G, 95th Illinois Regiment, on 17 November 1862, from near Jackson, Tennessee reads:

" ... we have just discovered one of our soulder belonging to this rigment is a woman and she is found out and sent home she is one of those loose caractors that used to run around camp in rockford she put on mens cloths and enlisted just before we started ..."

Thomas Hannah indicates that this woman was sent back to Belvidere.

After the war, Cashier returned to Belvidere, Illinois for a time where she lived as a man who worked for Samuel Pepper.[4] She settled in Saunemin, Illinois in 1869, where she worked as a farmhand, choosing to remain as a man. Her employer there, Joshua Chesebro, built a one-room house for her. For over forty years, she lived in Saunemin and worked as a church janitor, cemetery worker and street lamplighter. Because she lived as a man, she was able to vote in elections and later claimed a veteran's pension under her pseudonym Albert Cashier. In later years, she ate with the neighboring Lannon family. A later tale tells that the Lannon's discovered that she was female-bodied when they asked a nurse to look at "him", but they didn't make their discovery public.

In November 1910, Cashier was hit by a car that broke her leg. A physician discovered "his" secret in the hospital, but did not disclose the discovery. On May 5, 1911, Cashier/Hodges was moved to the Soldier and Sailors home in Quincy, Illinois. She lived there as a man until her mind deteriorated and was moved to the Watertown State Hospital for the Insane in March 1913. Attendants at the Watertown State Hospital discovered that she was female-bodied when giving her a bath, at which point she was forced to wear a dress.

Albert Cashier/Jennie Irene Hodgers died on October 11, 1915. She was buried in the uniform she had kept intact all those years and her tombstone was inscribed "Albert D. J. Cashier, Co. G, 95 Ill. Inf." It took W.J. Singleton (executor of Cashier's estate) nine years to track Cashier's identity back to her birth name of Jennie Hodgers. None of the would-be heirs proved convincing, and the estate of $418.461 was deposited in the Adams County, Illinois, treasury. In the 1970s, a second tombstone, inscribed with both of "his" names, were placed beside the first.

Also Known As Albert D. J. Cashier: The Jennie Hodgers Story is a biography written by veteran Lon P. Dawson, who lived at the Illinois Veterans Home where Cashier once lived. The novel My Last Skirt, by Lynda Durrant, is based on his life. Cashier's house has been restored in her home town of Saunemin. 

Brittish Army surgeon, Dr. James Barry, dies in 1865, and is discovered to have female sexual characteristics. Barry had been passing as a male since at least 1809. 

During World War I from 1914 to 1918, Transvestites were being regularly charged as spies or cowards, and executed. 

During World War II in 1935, the Nazis abused, murdered, and sterilized transgender men and women. Aversion Therapy, which was first used to eliminate homosexuality, was later used on transgender men and women as well.

A United States Army colonel was discharged and sentenced to 90 days in Leavenworth on October 26th, 1990 for appearing in drag at an AIDS benefit and kissing another man. 

The Transgender American Veterans Association (TAVA) was founded in 2003.

In 2010, Australia ends their ban on transgender people in the military.

In 2011, the Veterans Health Administration issued a directive stipulating that all transgender and intersex veterans are entitled to the same level of care "without discrimination" as other veterans, consistent across all Veterans Administration healthcare facilities.

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