Hello! This is my project for July 2019's NaNoWriMo, my first time participating! I'll most likely publish updates every Friday, since my other current story (Coffee, Books, and Secrets) is generally updated on Mondays. If you love AU KakaSaku stories, please go check that one out!

Summary: Prince Haruno wakes every morning to bind his breasts and face the world while his life is turned upside down. He is hounded by his latest female suitor, tempted by the men around him, and doesn't have a clue how to be a woman. As he goes undercover as a lady-in-waiting, he will discover more than womanhood. There's a plot against the Kingdom, and he can trust no one.

Pairings: I plan to have the final pairing be SaiSaku and have KakaSaku for the other side of the love triangle, but I will see what everyone wants! Let me know as the story goes who your pick will be :)

Feedback/Reviews: I appreciate any and all reviews. I always love feedback, as it makes me a better writer. This story in particular, though, I want your feedback if you have some! If it goes well, I plan to adapt this into my first novel. Let me know if you ever love or hate something, want to discuss anything, or just let me know you're still with me!

Disclaimer: I do not own Naruto or it's characters, only the story idea. Many characters are OOC and out-of-place compared to the anime.

Chapter 1

A woman looked at me in the full-body mirror. Pink hair fell to her shoulders, framing the face filled with bright green eyes and soft cheeks. Her jaw was strong yet delicate, begging the eyes to trail from her ears to her chin. Her clavicle rested atop the sea of skin with a ripple of her breasts on the horizon.

The woman began to disappear. Her hair was swept onto her head, smothered by a wig of short brown hair. Trace amounts of dirt were smeared over her face, toughening her jaw. Her clavicle lost its luster as her chest was bound by layers of cloth and encased in a linen shirt.

I stared at my dull green eyes.

"Prince Haruno, King Danzo requests your presence," I heard from the other side of the door to my chambers.

"Thank you, Naruto."

I pulled on cotton shorts, stuffing a sock inside the front as my father taught me as a young child. I tucked in my linen shirt and tugged on my leather pants just as my door opened and my two knights stepped inside.

"Your Highness, we must leave at once to see your father," Sasuke said sternly. He was the stiffer of my two knights, always trying to be punctual and follow rules.

"We don't intend to rush you, Your Highness," Naruto added. I could always count on him to have the personality and the heart.

I had my waistcoat slipped-on and buttoned in seconds, but took my time strapping my boots to my feet. I could guess the topic of the day's meeting, me, and I was in no rush. My father and his privy council could wait a minute longer.

Knights weren't allowed to walk ahead of Royalty, so Sasuke breathing down my neck as we walked was as close as he could get to shoving me. Naruto stayed back a few paces, which I appreciated. If we were late to the meeting, my father would scold my knights. I didn't need Sasuke making me feel any more guilty about that fact.

I concentrated on my feet rather than the servants and guests bowing around me as we walked. I had to slam my feet onto the floor, making it sound as if I weighed more than I did. A Prince was to be a dominating force, my father once said, and walking lightly wouldn't do the job.

I nodded to the guards posted at the Council Room doors. They opened both doors, allowing me to sweep inside with the dominating force I hoped my stomping created. I went to the raised platform where my father sat on his throne. Sasuke and Naruto stayed by the door, which was the appropriate place for knights during council meetings.

The Privy Council members had stood at my entrance, and I waved for them to sit. My father grunted, and I couldn't tell if he was expressing disappointment for my delayed arrival or approval for dismissing his council without speaking, the kind of flippant attitude he holds towards his subjects.

A chair scratched against the floor, and I turned to see Duke Jiraiya standing. His bowed his head slightly before speaking. "Prince Haruno, this Council meeting has been called to discuss your upcoming birthday." He sat again when my father started speaking.

"The Dukes are concerned," King Danzo said. He had an amused glint in his eyes, and I knew I wouldn't like what was going to be discussed, just as predicted. "You have yet to show interest in a single suitor, and they worry you will be crowned King without a Queen at your side when I die."

The room buzzed with conversation as the Privy Council began to discuss my father's words. Would he die soon? Am I not ready to lead on my own? Why haven't I picked an heir? My head started to spin.

Duke Jiraiya didn't understand the rush for me to marry, while Duke Hiruzen pointed out the urgency for heirs. Duke Minato nodded along, which didn't surprise me. He had so many sons he didn't need to worry about his legacy; he could even afford his youngest, Naruto, becoming a Prince's knight — a station much lower than what he was born into — out of desire alone. .

"We will continue to welcome suitors," my father's voice rang in the room, silencing all conversations. "We have six months until Prince Haruno is crowned Heir. If not married or even engaged, he will be expressing exclusive interest in at least one suitor. Will that satisfy you all?"

I heard a chorus of "yes, Your Majesty" and "wonderful idea, Your Majesty."

Duke Asuma began a conversation about trade routes, and I stopped paying attention. I knew I'd eventually have to wake up and worry about trade routes and food supplies, but it all seemed so far away. I still woke every morning to worry if a maid threw away my bindings in the night, thinking they were scraps, or if I'd be surprised with my monthly bleeding before I had stolen bits of cotton.

The meeting ending, and I quickly excused myself. I declined Naruto's invitation to escort me to the dining hall for breakfast. Once we reached my chambers, I instructed Naruto and Sasuke to remain outside my door; I would summon them if I needed anything, I said. They agreed without question, as they were trained to do.

The Prince's chambers were connected to the Princess's, which would remain unoccupied until I found a wife. They would soon make my room feel like a prison, but for now they would help me gain my first taste of freedom. I slipped through the door connecting our chambers, careful to shut the door quietly lest Sasuke and Naruto hear it from outside the Prince's chambers.

The Princess's chambers were exactly like mine: a main living area, double doors leading to a balcony, and a bathing room to the side. This room was stripped completely bare, unlike mine which was lavishly decorated with foreign rugs and drapes.

I walked to the bed and saw the dress I laid-out weeks ago. I had stolen it on impulse. The tailoring room was left unoccupied during a rare moment I was alone, and I snuck inside to steal a dress without thinking. I had no idea what to do with it until two nights ago.

I slowly undressed. My fingers trembled as I unbuttoned my waistcoat. My linen shirt stuck to my arms in spots I was beginning to sweat as I slipped it off. Taking off my leather pants was even worse. Finally I was stripped to my cotton shorts and bindings, the last bits of clothing covering what made me a woman.

When I had stolen the dress, it was folded into a bundle and tied with ribbon. Now I saw it in three pieces: a skirt, a linen shirt, and a corset. I picked up the linen shirt first, it being the only article I knew how to put on.

The shirt was lighter than the men's shirts made for me. When I pulled it on, the sleeves were tight and were barely long enough to cover my elbows. The buttons were smaller, too, so I struggled to fasten them. The chest of the shirt hung on my frame, and I realized I needed to release my bindings to fill the shirt.

Bindings off and shirt back on, I tried the skirt. I twisted it a few times before finding which part of the skirt went in the front. I sat on the bed and stuffed my legs through the top hole, struggling to get my feet through the layers and to the other side. I managed to secure the skirt around my waistline.

The corset was the most intimidating. I'd heard women complaining about how complicated corsets were to lace. Higher-born women even had servants to help them. I was in over my head, but I knew I had to try. I practiced three times on the bed before slipping the corset onto my chest. I didn't know how many minutes passed before it was finally laced.

Two nights ago I knew what I wanted to do with the dress. It would be dangerous. I embraced that.

I took off my wig, wiped the dirt from my face with the linen shirt I was wearing when I was still Prince Haruno. My heart rate sped up at the realization that I was no longer Prince Haruno. I could and would walk outside the Princess's chambers, a stranger to the castle and to myself.

The Prince's and Princess's chambers were conveniently placed at a corner. My personal chambers would lead to the hallway my knights were positioned at, but the Princess's chambers would lead to a hallway perpendicular, where my knights couldn't see.

I stepped into the hallway and waited for knights to tackle me, demand I take off the dress and go back to being Prince Haruno. But no one came, and by the sounds of their bantering, Sasuke and Naruto hadn't even heard any doors opening and closing.

I decided to go to the servant's wing. My simple dress would have stood out among the wealthy guests wandering the halls near my chambers, and I didn't need anyone looking too closely at me. Thankfully no one did. I was a nobody as I walked, someone not worth giving a second glance to.

It was exhilarating.

I was so invisible that as I rounded a corner near the kitchens, a man smacked into my chest, knocking me to the floor.