Summary: When Reborn is sent to Japan to train Sawada Masako to be Vongola Decima, he is surprised to find Sawada Tsunayoshi instead, a struggling young trans man trying not to drown in a world where no one takes him seriously. And suddenly, Reborn finds he is not only a tutor, but also a parental figure to his new young student. Vignette series. No pairings. Character-driven.

Disclaimer: I do not own KHR.

Disclaimer: I am not a transgender/transsexual individual and do not in any way claim to be an expert on this subject. I have done research in order to make this as accurate as possible given the characters and the world in which they inhabit. That said, I am human and prone to making mistakes. If you notice I have made a mistake, please do let me know and I will do my very best to fix it.

"It's Reborn...looks like you were called by the old man again," said a voice from in front of him, and Reborn didn't have to look up from cleaning his gun to know that it belonged to one of the regulars of the bar he was currently in.

"Must be tough being popular," added a new voice. "Going to Rome next? Venice?"

Reborn was silent a moment before saying a curt, "Japan."

As soon as he said this, a hush fell over the entire bar and the tension in the air skyrocketed.

"What!?" demanded one person. "So the old man finally made up his mind!"

And with this one exclamation, the ice seemed to have broken, as the rest of the bar's occupants started murmuring amongst themselves and taking out cell phones to spread the message.

Within seconds, the entire mafia would know that the Vongola had found another heir.

And that was just what Reborn had wanted; it was the reason he'd chosen this particular bar, whose clientele was made up of the most talkative and most well-connected of the mafia.

It was finally time to put to rest the rumours that the Vongola's bloody reign was coming to an end with the deaths of the Nono's sons.

Standing up, the infant smirked triumphantly as he exited the bar.

"Looks like it's going to be a long journey."

"Ciaossu!"

Silence reigned in the bedroom as both of its other occupants looked down at Reborn.

Taking advantage of the silence, the hitman took a moment to study his new charge, and he couldn't help but let out an internal sigh.

At first glance, it became immediately apparent that Iemitsu knew absolutely nothing about his child.

Reborn had often wondered if Nono had had a momentary lapse in judgement when he had made Iemitsu the External Adviser of the Vongola, but now he was sure of it.

Everything from the way the youngest Sawada held himself to the way he dressed and even his hair showed that he was obviously a male, and not just, in his father's own words "a bit of a tomboy."

Upon finishing his initial assessment of his new student, Reborn broke the silence by stating, "I arrived three hours early but as a service, I'll evaluate you now."

Seeming to snap out of her daze, Nana asked in a concerned voice, "Hey...whose kid are you?"

"Hm?" replied Reborn, a slight smile on his face. "I'm Reborn, the home tutor."

"Oh!" exclaimed Nana, her hands flying to her mouth.

Her son, on the other hand, let out a snort which soon turned into full out laughter.

"I was wondering what sort of person created that bullshit flier. It's this baby!?"

Ignoring Nana's quiet "Oh my", Reborn turned his attention to his charge.

"So you're Tsuna," he said, and the boy immediately stopped laughing in order to stare at Reborn disbelievingly, his eyes narrowing a bit.

Reborn was a little perplexed at this reaction until Nana interrupted, saying in slightly stiff voice, "I'm sorry, Reborn-kun, but I think you're mistaken. My daughter's name is Masako."

Tsuna flinched almost imperceptibly at his mother's words, and Reborn immediately realized why the boy had been so surprised at being addressed as Tsuna.

Now, the brunette was looking at him, waiting for his reaction, and Reborn knew that his next words would have to be chosen wisely, for they would most probably dictate how well his relationship with the youngest Sawada would go.

Looking up at Nana, Reborn took a step towards her, causing her to back up a little.

"I'm sorry, Sawada-san," he said, gently herding her towards the door, "but at this moment I will have to ask you to give my new student and I some privacy. Tsunayoshi and I have quite a bit to discuss."

Closing the door behind her, Reborn waited until he heard the sound of retreating footsteps before turning back to Tsuna, whose eyes were wide with disbelief.

"Stop gaping and sit down," ordered Reborn. "We have a lot to talk about."

Tsuna seemed unsure for a moment whether to follow the orders but in the end, he sat down.

"In order for me to come up with an effective lesson plan for you, I need you to answer my following questions truthfully."

Tsuna was quiet for a moment, seeming thoughtful, before asking, "I'm sorry, but who exactly are you and what are you going to be teaching me? Because there's no way you're a normal baby so..."

Reborn, though annoyed that he had been interrupted, decided to let Tsuna off the hook just this one time because he had a valid question – it was good for a future mafia Don to be wary of strangers.

"My true line of work is assassination," answered the infant, "And my real job is to make you a mafia boss."

Tsuna's eyes widened in alarm when he heard this.

"WHAT?" he demanded, his voice sounding panicky. "But why me? I don't even know anything about the mafia! There has to be someone more qualified!"

"There isn't," replied Reborn. "All three of the current boss's sons were killed and therefore you are the only remaining heir."

"But I'm completely useless!" protested Tsuna. "I don't even know how to get people to call me by the right name and you want me to take over a mafia family?"

Clicking his tongue in annoyance, Reborn delivered a swift kick to the gut of his student, leaving him wheezing.

"Don't insult yourself. It is unseemly for a mafia Don and will lead to other Families taking advantage of you and will ruin our reputation."

Tsuna looked like he was about to argue, but didn't say anything; probably for fear of being hit again.

"Good," said Reborn, nodding in approval of the silence. "Now I'm assuming by your mother's reaction that you're not currently on testosterone."

Tsuna nodded mutely.

"Do you want to be?"

Tsuna's eyes widened at this, before he said a breathless, "Of course!"

Nodding, Reborn said, "Okay. Tomorrow, you will come with me to see your new doctor. He will be giving you all the information you need about hormone therapy, and if you decide you still want to go ahead with it, you will have to start meeting up with him regularly."

His brows furrowing a bit, Tsuna opened his mouth, as if he were about to ask a question, but Reborn beat him to it.

"The doctor works for the Vongola, the family you are now the heir of, so you don't have to worry about bills. In return, I will train you for your position as Vongola the Tenth up until the day of your Inheritance ceremony, on which you will have the choice to accept or refuse your new position. If you refuse, you will, at that point, have to find yourself another doctor, but will not have to pay back the Vongola. If you accept, you will become the official head of the Family and will start studying under the Ninth, who will teach you all the things only the head of the Family is privy to."

Tsuna was quiet for quite a while after this, deliberating, before he finally asked, "What will happen to you after the Inheritance ceremony?"

"I am currently Vongola Nono's most trusted assassin and a close advisor to him. If you accept your position, it is up to you whether I continue to be so or not."

Nodding thoughtfully, Tsuna let out a sigh of resignation, saying, "Fine. I'll go along with this. Bunt ONLY until the Inheritance ceremony."

Reborn nodded his approval.

"When is the ceremony, anyways?"

"On your eighteenth birthday."

"HIIEEEE! BUT THAT'S FOUR YEARS AWAY!"

SkyGem: Well, that's our little intro. I hope you enjoyed it! This fic will be largely from Tsuna's and Reborn's points of view with some other characters thrown in occasionally. It will focus mostly on Reborn helping further Tsuna's transition and also on Tsuna's relationships with others, most particularly his guardians, Reborn, and his doctor (whom I'm sure you've all already guessed the identity of). If there are any issues any of you would like me to address, by all means, let me know! And if there are any lgbtq+ individuals in my audience, I would love to hear about your experiences, if you feel comfortable sharing them. Just shoot me a message, eh?