Warnings - Slash, potential NSFW (I may have to change the rating) Trans!John, Fem!John

I do not own the musical Hamilton or any of the character personalities created by our lord and saviour, Lin Manuel Miranda

December 1774, London


Jaqueline Laurens turned around, quickly wiping the tears off her face, to see a squealing nine year old stumbling towards her, covered in grass stains and mud. He was being closely followed by a quieter eleven year old, who was trying in vain not to get himself dirty.

"James! James!" called a girl at the top of the hill, who was holding the hand of a toddler, "You better not get your clothes muddy! Pa is going to be so mad!"

The older girl stooped down and spun James around, the latter shrieking with delight. Martha Laurens stopped half way down the hill and looked at her sister with amusement.

"Don't encourage them, Jack," she scolded, feigning irritation, but she was smiling as she shook her head.

Jaqueline turned towards her younger sister, grinning, with eyes full of mirth. She walked towards them, putting James down carefully and taking the older boy's, Henry Jr, hand.

"My, my," the freckled girl laughed, "How did my little fifteen year old sister become so mature? Ma would be proud." Martha's face flushed with delight and pride, but she still pushed Jackie playfully.

"You're the lucky one, Jack, you get to go to school! To school! Whereas I stay at home and look after this lot," she gestured to Mary, the toddler, and James. Jackie bit her lip and frowned.

It was true. Since she could talk, Jaqueline had begged her father to let her go to school. At first he had dismissed it, thinking it was something she would grow out of, but as she aged it was clear that it wasn't a thought she was giving up. Even though a few rich girls would go to school, the majority were educated at home in domestic chores. She knew she would be married away to a stranger and spend the rest of her days locked inside a house, providing suitable male heirs for her husband. Jackie wanted her best shot at life, so she decided to get an education at a proper school.

Surprisingly, her mother encouraged her. Perhaps she wanted her eldest daughter to have a better life than her. Sadly, she passed away four years ago, a month after Mary was born. Since his wife's death, Henry Laurens had grown further away from his children, barely talking to them except when it was necessary. On the off chance that he did, it was short answers, often snapping at them. So Martha and Jaqueline had to look after their three siblings themselves.

Finally, after years of arguing back and forth, Henry had reluctantly agreed to let her go to school. One month ago, Jackie began to study law. She was ecstatic, yet also terrified. A girl, studying law? Her classmates thought it was a joke. To make it worse, she felt very strongly about the revolution, freedom for herself and slaves. Freedom for everyone, maybe. She wanted to fight for America, fight for her country, but how could she express this? A girl fighting just couldn't be. Even though she was fighting with herself. Fighting with-


She blinked and looked up to see three concerned faces. Except Mary, of course, who was running in circles giggling. Jaqueline laughed shakily.

"Well, Martha, you should be the one going to school, not me," she teased, "You're much smarter than I am, if only you used that brain to think instead of pining after every attractive young man." Martha snorted and shook her head.

"School? Although I might envy your freedom, it's not for me, Jackie. Come on, let's head back inside. Papa will be waiting for us." Although she said it in a light hearted tone, Jaqueline could see a flicker of fear on her sister's face.

Henry was indeed waiting for them, with a stony look on his face.

"Where were you?" he growled at Martha. She cowered in front him, and was about to open her mouth when Jaqueline interrupted.

"Pa, it was me, pa. I-I was outside and they came looking for me. Don't blame Martha, pa." Without taking his eyes off of the the quivering teen, he addressed Jack.

"Don't speak unless spoken to, girl," he said, dangerously calm. Speaking to Martha this time, he whispered, voice barely audible;

"Where. Were. You?"

Martha looked down and swallowed, then finally opened her mouth, "We-we were outside pa," she managed, her voice shaking. Out of the corner of her eye, Jaqueline could see the boys clutching onto Mary, their eyes wide with fear.

"And why were you outside?"

Martha swallowed, terror etched across her face. Tense silence filled the room, and all you could hear was the younger girl's nervous breathing.


"Hurry up, girl!"

Jackie stepped forward, unable to keep quiet any longer.

"It was me pa, I went outside, don't punish Martha pa, mama wouldn't have-"

Henry spun around so quickly Jack couldn't even think. He struck her across the face, and she gasped at the sudden pain, stumbling backwards. Martha recoiled, and the boys gripped each other tighter. Even Mary had stopped making any noise.

"Do not speak about your mother in this house, girl. I thought I told you not to speak unless spoken to," he snapped, face red with rage, "You are already a disgrace to this family's name, don't give me another reason to send you away! Martha," he growled, using her name for the first time that day. She yelped in surprise. "Do not go outside unless told to. Do you understand?"

Martha nodded quickly, understanding that it was time to leave. Gathering the boys and Mary, she shot a sympathetic look at Jaqueline and left. Henry sighed and rubbed his temples, as if Jack was an annoying headache he had to deal with.

"Why do you always have something to say?"

"Pa I-"

"Shut up, girl. Your sister can speak for herself. She's smarter than you. She knows when to keep her mouth shut, she doesn't want to go to school," his voice was raised, so he paused, regaining his composure, "All I want is a decent, normal family. Is that too much to ask?"

Jackie bit her lip, knowing that it was not the time for a snide remark.

"Go. Leave my sight," her father muttered.

She happily obliged, running to her room and closing to door immediately. She slid down until she was sitting on the floor and sobbed. Jackie's throat had been tight like a knot, and it felt like all the pressure was released as she wept. Tears streamed down her face constantly, too fast for her to wipe them away - not that she wanted to.

There were two faint knocks at the door. It was too gentle to be her father, but Jaqueline didn't want any visitors.

"Not now," she croaked in between sobs. A pause, and then footsteps walking away.

Jackie crawled over to her bed, rummaging underneath and pulling out a large box. She wiped the dust away in one swipe and lifted the lid. It contained clothes, her father's old clothes.

Now, one may think that it would be strange to keep your father's clothes in a box underneath your bed, but Jackie wanted to remember him. When she was younger, long before ma died, he would play with her. He would smile at her and laugh with her. However, that man was long gone. One might also think it would be a bit forlorn to act like your father is dead, and this man you see everyday is someone different, but it wasn't far from the truth. The grim truth, but the truth nonetheless.

Jaqueline stared at the fabric in her hand, then looked around guiltily as if she was about to commit a crime. She suddenly paused.

What if...what if no one is ever going to accept me as a girl.

No one lets a girl fight.

No one lets a girl speak for herself.

But a boy...

She shook the thought from her mind immediately. It was silly and childish. If God wanted her to be a boy, He would have made her a boy. Wouldn't He? Maybe, just maybe, she was a boy. Trapped inside a girl's body, trying in vain to escape. Jack groaned, trying to rid herself from this incessant thoughts.

However, they persisted.

But what if...

If you were a boy...


Everything would be easier...

"Fine!" she yelled, then instantly slapped a hand over her mouth. The entire house was silent as Jaqueline waited tensely to see if anyone had heard her. After a few minutes, she figured, with relief, that she was safe.

Turning again towards the box, she deliberated for a few minutes. Well there's no harm in it, she thought decidedly. As if she had made her mind up, she grabbed some gauze from her first aid kit she played with when she was younger. She would imagine that her dolls were wounded soldiers, and then pretend she was a wounded soldier, covered in injuries from her heroic battles. Her father didn't exactly approve.

Slowly, she undressed, and glanced at her body in the full length mirror. Jackie had always hated it, but she didn't know why. It wasn't as if she was ugly.

She was shorter than most girls, with wider shoulders. She lacked the hourglass figure that many females her age desired, and her skin was covered in freckles, from her toes to her cheeks. The South Carolina sun had been forgiving, so even though she had a darker complexion than most, she wasn't as tan as her siblings. Her curly, hazel hair tumbled over her shoulders in waves. Jack would refuse to wear a wig, finding them itchy and sweaty. It was certain her sister Martha was the belle of the ball, not that Jaqueline minded.

Carefully, she wrapped the gauze around her breasts. The clothes were too big for her, but she would have to make do. After fiddling with the length of the jacket sleeves for some time, she tied back her hair into a ponytail with a matching blue ribbon to complete the look. When she stepped back in front of the mirror, Jackie let out a gasp.

She didn't look like herself. This wasn't Jaqueline Laurens. This was someone completely different. The young man in the mirror smiled with delight, spinning around to look at himself. He wasn't the most attractive man, but then again, he was far from ugly. Soft, brown eyes gazed at Jackie as he got used to this new idea. He looked away from the mirror, and focused on his hands.

If he could become this new person, if he could convince everyone that this was the new him, maybe I wouldn't be judge anymore...but what was a face without a name? What was his name?

John. His name was John.

"John," he whispered, shivering at the delicious sound of his new name on his own lips.

It felt real

It felt right

It felt natural

It felt-

"Jaqueline?" a voice called. He jumped at the sudden noise. It was Martha. "Jack...um...papa wants us all in the drawing room,"

He scrambled to take off the clothes, throwing them into the box in a rush and shoving it under the bed. John went to take of the gauze and paused.


That was the one part of him that they couldn't take away.

He wriggled into a simple dress. The clothes felt strange, foreign on his skin, but he grit his teeth and dealt with the uncomfortable feeling.

"Coming!" he called, noticing how high-pitched and silly his voice sounded. That would have to change.

In the drawing room, their father was waiting impatiently, pacing the room. It appeared that the incident earlier had been completely forgotten, regarded as simply another inconvenience.

John seated himself on an easy chair stiffly, his back straight as a board. Martha had Mary on her lap, and was watching him worriedly, as if she knew something was different but couldn't quite figure out what.

"Jaqueline is currently studying law," Henry suddenly spoke, making them all jump. He spat out the words as if they were bile, "And the boys have been enrolled into British schools. Martha has proved herself capable of caring for them whilst Jaqueline is at school. Therefore I am leaving for Charleston next month,"

Jaqueline was stunned into silence. Looking around, she saw that the others shared the same gobsmacked reaction. He was leaving?

"Does anybody have any issues with that?" he asked, making it very clear by the tone of his voice that if they did, he didn't want to hear them.

When nobody spoke, he nodded approvingly. "Good. To be more precise, the ship will arrive in three weeks time. I have prepared already and I suggest that you do too in the time given. When I shall return, it is not clear, but the maximum time I will be away is three years" With that final statement, he stalked out of the room.

Henry was the first to break the silence. "Papa is...leaving?" he trembled. Martha hurried over to him and hugged him tightly.

"Shh, baby," she whispered, rocking him back and forth. Even though their father regarded John as a nuisance, he always had a soft spot for his oldest son. The brunette realised, suddenly, that he was now the oldest son.

The next three weeks were such a blur John could barely register what was going on. Then, before he knew it, they were waving their father out of the door. In between his studies, John would practice, well, being a guy. He wasn't used to all the social norms that revolved around the gender.

John would still go to school and pretend to be a girl. It was painful, but he kept reminding himself it would be over soon.

He was changing his body, too. John kept the gauze on, except when he was sleeping. He changed it every so often, and washed it. By the end of 1775, his voice was significantly lower than before, as he practiced speaking like a 'man'. It wasn't long before his siblings were noticing the differences as well.

Martha found out first. When he was confident enough, John would dress up in his father's clothes and sneak out of the house. The first time was terrifying, because he didn't know where to go. Eventually he walked into a pub. British soldiers milled about, people his age and adults stood in groups, laughing heartily, many in a drunken state.

John quietly ordered a drink and slipped to the back of the room, but it wasn't long before curiousity got the better of him. He walked over to the bar, and not one but two girls came over and began flirting shamelessly with him. Needless to say, John was hopeless at flirting, much less with girls. He told them politely that he wasn't into girls, and they blinked, stared at him and called over one of their male friends.

John got home late that night.

By the seventeenth time he visited the bar, he was used to the rowdy shouts and snide comments, not always from the men.

However, one time he was sneaking out, he rounded a corner to be greeted with Martha holding a candle. They stared at each for what seemed like a decade, then Martha raised her eyebrows and whispered, "Jaqueline...?"


"Why didn't you tell me?"

John averted his eyes from his sister's intense gaze and sighed.

"I...thought you'd hate me,"

Martha ran into John's arms and hugged him tightly, on the verge of tears.

"I could never hate you!"

She looked up at him, eyes shining in the dim light and John realised just how lucky he was to have her in his life.

"I could never hate you...um...big brother," Martha ventured.


When Martha looked up again, John was crying. He knelt in the ground and buried his head in her arms.

"I-I'm sorry! Did I say something wrong!?" she panicked. John, still shaking, shook his head. Martha relaxed, holding her brother's hair to her chest and listening to his steadied breathing.

"What's your name?"


Martha rolled her eyes and stared into John's.

"Well I don't know many guys who go by 'Jaqueline'. So, what's your name?"


"Well, John, it's way past your bedtime,"

He chuckled, and ruffled her hair. He was about to go back to his bedroom when he turned around.

"Don't tell the boys yet. Please. I'm not ready,"

"Don't worry, I won't. But how are you going to tell papa?"

John stared at the wall.

"I-I don't know yet. I'll find a way though, don't worry,"

Two more times John encountered Martha whilst sneaking out. She just grinned and shook her head at him, then let him go past.

Both times John stuck out his tongue ruefully.

One day, however, Martha pulled him aside. "I cannot bear to watch you dress up in those clothes anymore. They're way too big for you! Come on, I'm buying you some new ones," John blinked at her.


"It's alright, I've got someone to look after the children. Get your jacket, we're going into town,"

Before John could object, Martha had him by the arm and was pulling him out the door. They walked through the streets of London, John trying not to be seen by anyone at school in the fear that they'd recognise him, and Martha peering into shop windows. Eventually she dragged John into one. She had him measured, and he tried different clothing on. At first he was bored, but as the day went on he got rather excited by the prospect. He finally settled on a blue jacket with beige pants and waistcoat - after Martha's approval of course.

The shop keeper found it all very amusing. "Usually," he remarked, "It is the man picking out the clothes for the lady, or at least their mother." John stood there awkwardly, unsure of what to say. Luckily for him, Martha - bless her soul - came to rescue again.

"My brother has no sense of fashion whatsoever, and I'm afraid of what he would come back with if I had let him go out alone," she chuckled. The shopkeeper raised his eyebrows and said nothing.

When they arrived back at home, Martha made John parade around the house in his new attire. They ended up falling over one another in fits of laughter. As John watched his sister, her head tilted back and eyes full of mirth, he couldn't help but feel proud.

February 1776, London

"Henry! Henry! Jackie, Martha, tell Henry to slow down!" panted James, who was chasing his brother around the room. The thirteen year old only chuckled in response, but willingly stop running and let himself be captured. Martha was paying no attention, for she was tending to Mary on her lap.

"Martha?" she gurgled, blinking innocently at the seventeen year old.

"Yes, Mary?"

"Hungry. I'm hungry,"

Martha sighed and looked over to John, who stifled a laugh. However, it was his sister's turn to laugh as he desperately tried to adjust the dress. He rarely wore them, only at school and when around his brothers, and he had never been good at wearing them in the first place.

There was a knock at the door, so Martha let Mary toddle over to the boys. John watched his younger siblings antics absentmindedly, but really he was listening to the muffled conversation happening through the wall. Despite straining his ears as much as he possibly could, John couldn't make out any words, so he settled back in the chair.

Not two minutes later, Martha walked back into the room, followed by an older man. Their father.

His signature frown had seemed to sink lower on his face, and cruel, sharp eyes darted around, examining John and his siblings as if they were nothing more than items of clothing.

"Pa...?" whispered James, running over and hugging his legs. His father gave him a tight lipped smile, and looked around the room.

"I'm glad you are all here for my return. We will begin to make some changes immediately. The boys will resume school until needed, Martha, we will see to finding you a good husband, and Jaqueline," he looked up briefly and narrowed his eyes, "You will be married to Matthew Laurens next month. His family are friends of ours and it is necessary that we-"


John was on his feet immediately, a look of disbelief and horror on his face. Martha widened her eyes and shook her head vigorously at her brother, but he payed no attention to her warnings.

"I-I've never met him...I don't want to marry a stranger!"

Henry silenced his pleas with a cold stare. "You don't get a choice," he continued nonchalantly, "I expect my daughters to marry a civil gentleman who can put her in her place,"

"I'm not your daughter!"

He whipped his head around and stared, gobsmacked, at the defiant adolescent.

John bit his lip and pulled his hair into a pony tail.

"I-I'm your son," he whispered, "My name is John,"

Henry Laurens face flickered from anger to confusion to horror then back to rage. In one swift movement, John had been shoved to the floor. His head hit the wall, and he stared in dazed surprise at his father, who was practically foaming at the mouth.

"I have given you food. I have give you shelter. I have given you an education," Henry growled, stepping forward menacingly. John shrank back in fear. "I have raised you, but where the Hell did I go wrong?!"

He turned, took a deep breath, and began to walk away. When he reached the door, he turned his head and gave John a cold, unforgiving look.

"You are no son of mine," he hissed.

February 1776, London

"John! John! Wait!"

John kept walking, trailing behind him a small bag of belongings. Salty tears stained his face but no more fell for he had no more to cry.

"John, please. John!"

He finally turned, and waited for his sister to catch up. She too had been crying, and behind her followed the two boys, one leading Mary by the hand.

"Sister Jaqueline is a...boy?" asked Henry Jr, staring at his clothes. John had long since changed outfits and left behind all traces of the old him. He knelt down and smiled at the confused boy.

"Yes. But I'm not your sister Jaqueline anymore, I'm your brother John," he explained. His younger brother tilted his head, processing the new information. As if he had made up his mind, he nodded.

"But we can still call you Jackie..?" he asked.

John laughed. "If you want to,"

Martha ran forward, pulling her brother into a tight embrace.

"Oh, John," she sobbed into his shoulder, "We're going to miss you. Do you have to leave?"

"I'm going to miss you too," he said gently, brushing away her tears, "But I do. I'll write to you,"

James hugged his leg tightly and even Mary was quiet for a few seconds, as if she realised what this meant.

Pressing a final chaste kiss to Martha's forehead, he walked away from his family, knowing that it might be he last time he ever saw them.

But he was going to start a new life.

Be a new person.

In New York City.

A/N - Whoa I actually finished the chapter. Some parts of this are not historically accurate but fuck historical accuracy amirite? In all seriousness I tried to get this as close to the actual events that I could, but the characters themselves are the personalities created by Lin Manuel Miranda. Reviews are always welcome!