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It's late at night.
Leonardo is sitting on the rooftop of one of New York's many apartment buildings situated on the outskirts of the city, his legs crossed, his eyes turned skyward. For a month now, he has had the habit of sneaking out of the lair as soon as his family goes to bed to spend some time there, in what has become one of his favorite places, a slice of tranquility amidst the chaos of his life. Not that there was anything special about that rooftop in particular. What really made it special was—
Leonardo senses it immediately, the presence of someone behind him. It's someone trying to make as little noise as possible as they get closer to him, but he's a well-trained ninja and can hear everything: every breath, every step, the air that moves with every movement of that person who's trying to catch him by surprise. He pretends not to have noticed anything, though. He stays still and waits for the right moment.
You lunges toward his shell, trying to hug him from behind. Without batting an eyelid, Leonardo grabs you by the back of your shirt and throws you over his shoulders and into his arms. Now you’re there, breathless, sitting on top of Leonardo's crossed legs, your head supported by his right arm, looking up at him in amazement with those brilliant eyes Leonardo has come to love.
He chuckles in amusement, looking down at you, his gaze full of affection. "Did you really think I wouldn't notice?"
"Oh, come on! I was so quiet, how could you hear and know it was me?!" you pout, but your protests quickly turn into a giggle. "You don't miss anything, do you?"
"Sensei would be very disappointed in me if I were caught unprepared for this kind of ambush, especially when orchestrated by lumbering beginners." He explains, his tone light, playful.
“I will pretend not to be offended by being called a ‘lumbering beginner’, even if it’s true.”You adjust your position, getting more comfortable on his lap and against his chest. “Now, unfortunately for you, I’ll stay right here and you'll have to hold me like this the whole time, hah!” You copy the playfulness of Leonardo’s voice, your lips curled into a smirk. He knows you're trying to make him think that even if you didn't manage to fool him, in the end you're the one who won and got the prize. But you don’t know how wrong you are, because Leonardo now has in his arms the person who made this simple rooftop his special place, so if anything, it's a draw. He doesn't tell you, though, he lets you rejoice in your small victory and focus on the warmth of your body and the furious beating of his own heart. If only you knew how happy and nervous being this close to you makes him feel.
He thinks back to that fateful night a month ago when you first met. He'd ended up in that part of town because Raphael had decided to storm off the lair and go topside alone after getting angry and arguing with everyone. Which wasn’t really something new, but trusting Raphael not to do something impulsive in those conditions wasn’t something that they could do. So Leonardo and the others had gone looking for him under Splinter's orders and had decided to split up. But instead of finding his brooding brother, Leonardo had found you.
You were sitting on the edge of the roof, lost in thought. He would be lying if he said he hadn't been curious about you from the start, but then again, before that night, he had never seen a human being up close, much less a woman, and as much as he prided himself on his discipline and self-control, being so close to someone outside his family had distracted him. That's why he'd made a misstep, making a noise. The same noise that startled you and made you lose your balance. You would have crashed onto the road below if Leonardo hadn't had his quick reflexes and grabbed you just in time.
He still remembers the leap his heart made at that scene, his hand tight around your wrist to keep you from falling, and your eyes, scared and incredulous at the same time, fixed on his.
Time seemed to stand still as Leonardo waited for your reaction after almost falling to your death and after being saved by a giant humanoid turtle. He remembers thinking how stupid and careless he was to have caused such a thing and to have been forced to reveal his existence after his father had warned him since he was a child to stay away from humans.
“You saved me” was the first thing you said to him after minutes of silence as he pulled you up and steadied you on your feet, while you kept looking at him like you were trying to figure out what exactly was in front of you. Which was still a much more positive reaction than he would have expected.
“I’m really sorry, miss. It was my fault, I startled you and almost made you fall,” he apologized politely, bowing to you in the manner his father had taught him to show respect. He heard you giggle then, and so he stood up straight again, looking at you in confusion. Maybe the strange one was you.
“No, I should have sat down somewhere less dangerous. Thank you for saving me from certain death,” you had replied, smiling. You were taking the situation way too lightly in his opinion, but Leonardo didn't really know you so he didn't feel he had the right to judge.
Then you looked him up and down. “Can I ask you… What are- no. Who are you?” You seemed embarrassed by the fact that you had to ask him something like that, but your eyes couldn’t conceal your curiosity. He didn’t blame you. He appreciated the fact that you tried to be tactful, in fact.
He explained his nature, the fact that he was a mutated turtle trained to be a ninja, and made you promise not to tell anyone about his existence. Then a sound came from his com, Donatello's voice updating him that he had found Raphael and that they all could go back to the lair as they planned. Leonardo looked at you one last time, considering whether he could really trust you, then nodded in sign of salute, and turned to leave. He would never have returned to that rooftop if you hadn't stopped him and asked “Wait! Will I see you again?" with a voice so full of hope that made him reconsider all his father’s words about direct contact with humans.
He should have said no. He should have obeyed his father’s warnings and be like the perfect rule abiding golden child that Raphael always accused him to be. Instead he responded “Maybe” before jumping off to another rooftop and disappearing from your gaze.
And the next night, he was there again, behind his family’s back.
And you were there too, waiting for him.
That's how your friendship began. Night after night spent chatting together in your little corner of the world, carved only for the two of you. Leonardo had never spoken so freely with anyone. Nor had he ever felt so understood and at ease. He found joy in your time together, and he felt good in having something all to himself. A precious secret away from his family.
Then things began to change. That friendship for which he had been so grateful had begun to feel too tight for him, suffocating him like a turtleneck-sweater shrunken in the washing machine.
And as your laughter, your complicity and the depth of your long chats increased, so did his feelings.
Now every time you found yourself sitting side by side on the floor, he could barely concentrate on the words coming out of your mouth or on what to respond. He could only think of your scent filling his lungs with your every move, of every time your shoulder brushed against his before pulling away, of how much he wished he could hold you and be lulled by your warmth. How your lips beckoned him closer, a siren song hypnotizing a poor sailor into drowning in the sea.
But Leonardo resisted. He would never do something without making sure you wanted it too. For a mutant like himself, befriending someone was already something incredible, unthinkable, a stroke of luck already too great. Moving on to another step, to a relationship that would entail kissing and intimacy, was probably too much to hope for. There was no way to know with certainty if the idea of undertaking something like this with him was something that would ever cross your mind or if it was something that, in the worst case, could disgust you. Not without asking directly, with the risk of ruining everything and getting his heart shattered.
But then Leonardo began to notice a change in your behavior, the way you seemed to linger on his facial features when you thought you weren't being seen, a certain wonder and admiration painted in your irises. The way your gaze sometimes dropped lower and lingered on the hard plates of his pectorals before blushing and looking away. The way your breathing became shallower, and your body stiffer and you seemed not to want to stop the contact when he touched you first.
Leonardo wasn't entirely confident in taking the first step toward that uncharted territory called love, but he was perceptive and knew that you too had stopped being content in the role of mere friend.
He tried flirting a little sometimes, testing your reaction, never overstepping too much. And when you responded by flirting back, the idea arose that perhaps, despite all the differences between the two of you, something more could actually work.
Maybe, maybe all the dreams he's had since he first realized he loved you could come true for real.
“You’ve been quiet.” Your voice bring him back to the present. You're still in his arms, closer than you've ever been. And you look at him with those eyes full of light, and maybe, maybe this is the right time to finally make that step and walk through that door.
He holds you a little closer. He brings the arm that's not supporting your back over your leg. He caresses your thigh with his thumb, a gentle, affectionate touch. It serves more to calm his nerves, to ground him, than anything else. And he looks at you, sinks into your eyes. The blue of his seems to become more turbulent, deeper.
“Would it be okay if I kissed you?" Leonardo finally asks. He's always been the most confident of his brothers, but now he feels like he's tossed around on a raft in the middle of the ocean, ready to sink at any moment, only you the one with the power to save him from that destiny.
He notices your eyes widen, your breathing hitching. For a moment, Leonardo is afraid. That he's not as perceptive as he thought, that he has misread the signals, that he has risked too much and he will gain nothing. But then you smile, your cheeks red. “I would love it if you did that.”
And so Leonardo leans down and kisses you. It's just a peck at first, just his lips touching your lips, a light touch that is enough to burn him from the inside out. He tastes how it feels, the softness of your mouth against his own. He feels like dying from the amount of emotions swirling in his chest, and then he dies a little for real because you try to lick and suck his lower lip. At this point he doesn’t really know what to do, he has never kissed anyone before, after all. He'll never tell you, but the only thing that he did was practicing making out with his hand closed in a fist in the solitude of his room — hoping that none of his noisy brothers would ever find out — to prepare himself for the eventuality of having to do it with you. He thought that would be enough to know how to move his lips better, but he still finds himself awkward. And the ticking bomb situated in his chest right now certainly doesn't help the situation.
“Wait.” Leonardo stops immediately, putting space between your faces and letting you breathe. He notices your shiny, red lips as he looks down at you and feels a bit proud knowing he was the one who made them that way, even though he knows perfectly well that the kiss must not have been great for you.
“Sorry, I've never—"
“No, me neither, for that matter.” You stop him from apologizing further, smiling. “I just want to get more comfortable, then we can practice more together." You smirk, and Leonardo smiles at that, both relieved and eager to continue. You get up, only to then straddle him, circling his lap with your legs in a lotus position. Your arms go to rest on his shoulders, joining behind his head. You gaze into each other's eyes for another moment, then lean in again.
Leonardo brings his hands to your hips and squeezes them, savoring your curves with his palms as he tastes your mouth again. You both try moving your lips again, using your tongues together, and this time it's better. After a few seconds of trying, you find your rhythm, and although there's room for improvement, the kiss becomes satisfying. Leonardo loses himself completely in the sensation, a rumbling chur erupts from his chest, and he hopes you don't pull away to ask what it is. He will explain later, right now he doesn’t want to stay a single second away from you.
Then the unthinkable happens. By the time Leonardo realizes, it's too late, because he clearly feels the slight jolt of your pelvis against him, letting him know that you noticed too. This makes things worse, because that small movement creates friction on the boner that has formed between his legs.
Leonardo brings his hands to your shoulders and gently pulls you away from him. He struggles to look you in the eye as he coughs to clear his throat.
“I'm sorry, I didn't think my body would react like this." Leonardo always thought of himself as a gentleman. He always thought that he could restrain and control every desire and reaction in his body, with the help of his training and his will. Apparently, he was wrong, so wrong.
He hears you giggle and he isn't sure if that should reassure him or make him sink deeper into embarrassment.
"Don't worry, from what I know it can happen to many." You try to put him at ease. He feels your hands cupping his face and then he finds himself looking directly at you again. “If anything, I’m flattered,” you tease him lightly, caressing his cheeks with your thumbs. One of his hands cups one of yours, still resting on his cheek, and he squeezes it. A chur rumbles in his chest again. This time, you do ask what it is.
“It’s something that we do, my brothers and I. Mostly when we’re happy. A turtle thing.”
The explanation makes you smile. “I’m happy too, Leo. A lot.” You pause, and Leonardo knows that you’re collecting your words to say something important about where the both of you stand now. But he won’t let you confess first, that is something that he should do.
“I like you. I really like you,” he says. Your name comes out softly from his lips. “I would be honored if you would take me as your boyfriend.” His gaze is serious but also a little shy as he waits for your response.
“I like you too, Leo. And I would be honored to be your girlfriend.” You smile and give him another quick kiss, almost like you’re officially sealing this new arrangement between the two of you. He smiles on your lips, then he clears his throat again because the ‘problem’ between his legs is still there. He’s not ready to take care of that part of him with you yet, so he gestures for you to get up. He’s thankful that you seem to understand and that you don’t push.
“I should go now,” he says, getting up in turn. He’s still a little bashful but you squeeze his hand lightly and you smile and that’s enough to calm him.
“Goodnight, then. See you tomorrow?”
He smiles, the affection that he has for you pouring from his eyes.
“Of course. Same hour, same place.”