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imtiredbutimhere · 3 years ago

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Obviously, when u can, when u have time, could I request…

How would the guys react to their first time? Would it be hot? Gentle? Rough? Would it be planned or would they be caught off guard? Nervous? Excited? I loved how u did the bj ask do something along those lines would be brilliant! And then! If you’re up for it and u have time available anytime how about how they would act the day After? Kinda like a sex hangover! Would they be on cloud 9? Excited to tell their brothers? Floaty light? Hopefully there’s food for thought there. Hope u like the ideas xxxx love ya!

Request from my dear @nittleboo 😘😘😘 You always have the best asks for me babe! Love you!!I’m treating these as the boys being in established relationships and I’m doing fem!reader this time.

Warning: Language and NSFW 18+ only

First Time Headcanons

Leonardo

Leo is a planner. He’s the leader. He makes all the calls.

So it shocks the hell out of him when you make the first move.

Date night, your place, dinner and cheesy old ninja movies complete with subtitles and terrible English dub.

His arm is around your shoulders and you’re snuggled up against his side.

And then your hand slides from his knee, up his thigh. A few inches at a time, until he’s not chuckling at the movie. He’s too focused and holding his breath, waiting for your next move.

To borrow his baby bro’s words, he can feel his shell tightening and it’s about to become embarrassing.

His eyes shift to yours, and he finds you staring intently back. You both still for a beat and then you’re on each other.

Mouths are crashing together sloppily as you tug one another out of clothes. Leo’s mind is reeling from the sight of all your naked glory and the softness of your curves. He palms, he squeezes, he laves his tongue against all your intriguing places.

He melts at your embarrassed gasp when he tastes your pussy for the first time. Your burning cheeks urge him on as he explores your most private area.

As amazing as it feels, you need him to fill you and you need it now. You start to beg and plead in a breathy voice, “Leo, I need you. Please fuck me now, please, please!”

He’s never felt more confident or accepted as this moment, hearing you beg him to fuck you. This gorgeous human female WANTS HIM.

He lays you back on the couch, and settles between your thighs. Looking you in the eyes, he grasps his cock and pushes it through your entrance.

He’s huge, and you wince. He stops immediately, terrified that he’s hurt you. You have to reassure him that you’re okay, you just need him to go slow and let you adjust to his size.

He grits his teeth and takes his time, when all he really wants is to plough into you until he explodes. Slow and steady, like Aesop’s tortoise.

When he hilts, you take a breather and then at your nod, he pulls back and thrusts forward.

HOLY FUCKING HELL ON WHEELS!!!

Your walls hug him so tightly, and it’s so warm and slick. He never knew it felt this amazing. His hand will never be able to satisfy him again.

Each rock of his pelvis is heavenly, and look at how beautiful you are, laying beneath him, meeting his thrusts with a rise of your hips.

Your eyes are glazed over in pleasure, and the sounds you make, those little moans and whimpers, the way you gasp his name. He’s quickly coming undone.

When he murmurs that he’s getting close, you clamp your legs around his hips to keep him from pulling out. Sliding a hand down between your bodies, you rub circles on your clit until you begin to twitch.

He’s roaring his release as you buck, cumming at the same time. He strains as he empties himself completely. He holds himself up to keep from squashing you as you both catch your breath.

The next day, his brothers notice a change in his attitude. He hums to himself while he makes his tea. His step is lighter, and they catch him staring off into space smiling a lot.

It isn’t hard to put two and two together.

Raph finally can’t stand it and has to ask, “Leo, man, throw us a bone here. Ya got laid last night, didn’t ya? How was it?”

Leonardo looks his brother dead in the eye and smirks knowingly as he answers, “I don’t know what you’re talking about.”

And walks away.

Raphael

He’s running his mouth, talking dirty, being a flirt like usual.

You two are hanging out in his room, just goofing off and enjoying each other’s company.

You’re telling him about your first time on a motorcycle and he just can’t help himself, the innuendo is perfect.

“I’ll take ya for a ride.” Insert brow wiggle here. Add smirk.

So when you retort, “Yeah? Why don’t you?” Insert hand on hip. Add narrowed eyes.

Wait, what? Raph’s brain is trying to catch up. Are you being serious?

Feeling both brave and sexually frustrated, you pull your top off and toss it to the floor.

“Are you all talk, Raphael? Or are you gonna give it to me as good as you say you can?”

You challenge him? YOU CHALLENGE RAPHAEL?? Oh, he’s back now. He’s gonna show you. Have you begging for mercy.

You see the lust darken his eyes and think, thank god, finally. Goading the big lug always does the trick.

He reaches for you and bye-bye bra! See ya sweatpants! Au revoir panties!

Now that you are naked before him, he feels his nerves coming back. You are so stunning and he’s just a green beast. Doubt creeps in but you see it and intervene just in time.

Sashaying up to him, you start pulling at his straps and his clothes. Scattering kisses on each fingertip, across his plastron, and once you have him undressed, you kiss the thick head of his cock.

Raph watches, enthralled as you lick his shaft, and try to fit it in your small human mouth. It’s doesn’t get very far, but he’s blown away by you taking the effort.

You suck on the tip and he’s so sensitive, he growls out, “Fuuuuuck” and pulls you away.

Before you can protest, you are in his arms and pressed back against the wall. He’s already trying to press his cock through your tight entrance and regrettably, you have to ask him to slow down before he hurts you.

Instantly contrite, his face falls, and you reassure him that this is normal for a first time together. You show him how to rub your clit to help get you wetter, and pull him in for toe-curling kisses.

As your walls slicken, he pushes in a little deeper, until he gets just over halfway. You both agree that it’s just going to have to be enough for now because you feel incredibly full and need him to move.

He starts thrusting, shallow at first, still afraid of hurting you. He groans at how well you squeeze his cock. You gasp at the fullness, but by god, he’s rubbing every sensitive spot inside you and you could weep at how good that feels.

As your moans grow louder, you begin to plead for “Faster, Raphie!” and “Right there! Harder!”

He’s happy to oblige. At some point, you are so wet, he has managed to slide all the way in, your walls accepting him and gripping him tight.

Pleasure has overridden both your brains, as you huff and puff, and fuck your way to orgasm.

You cum first, clamping down on his cock and making him cry out. It’s too much for his lust driven body and he pounds you into the wall until he’s shooting you full of his cum.

You know without a doubt that there will be bruises and soreness tomorrow, but it 👏🏼 was 👏🏼 so 👏🏼 worth 👏🏼 it.

Once you are snuggled down in his bed, he goes out into the rest of the lair. He’s grinning from ear to ear, but his brothers heard everything, so he doesn’t even have to brag. Leo shakes his head at him, but smirks a little. Mikey comes in for a fist bump and a “Congrats bruh!”. And Donnie salutes him from his computer chair. He’s already working on ideas for soundproofing their bedrooms.

And Raph is already planning your morning ‘wake up call.’

Donatello

It might appear to be a spontaneous decision on both your parts.

It is not.

Donnie has been meticulously planning for this since you started dating.

He’s read all the articles, studied the human anatomy, and watched more porn than anyone would guess. For science, of course.

He feels supremely confident that he can blow your mind right out of the gate.

He starts by increasing his ‘casual’ brushes against your skin.

Kissing you a little deeper, a bit longer. When you lean in for more as he withdraws, he knows it’s working.

He lets you catch him looking you over, licking his lips. Then faking embarrassment at getting caught.

He always sits sprawled out now, to draw your attention to his crotch.

It’s all been leading up to this moment. You were coming over to help him clean up the lab, and he already made sure that intrusions wouldn’t be a problem. His cot in the corner is set up with fresh blankets and bottles of water are in the mini fridge.

Now all he needs is to seduce the girl.

When you arrive, he wastes no time with his deliberate touches. He’s worked himself up with all his sneaky planning and he’s struggling to be patient.

He presses against your back as he reaches above your head to set something on the shelf. You stiffen as you feel the evidence of his desire bumping your lower back.

You gasp, “Donnie!” and whirl around as soon as he backs up.

There it is, straining against the zipper of his cargo pants. And good lord, is that a big bulge.

You stare hard, and damn if it isn’t getting bigger. Donnie’s fully erect cock is a beast and you can’t wait to take it for a ride.

Donnie watches your reaction, and just as he reaches for you, you jump him. Literally. He’s so tall, he has to catch you as you launch yourself into his arms and smash your lips to his.

He groans as he feels you grind against him, and when you pull his suspenders off his shoulders, he’s relieved that things are going in the direction he wants them too.

As clothes are peeled off, Donnie does a double take when he sees that you are wearing a matching bra and panty set in his shade of purple. You grin. “Did you really think I’m that clueless? You might be a genius, Donnie baby, but I can read you like a book.”

So much for stealth. He snort laughs and helps you remove them. He sits you up on an empty table and kisses you again, slipping a finger through your folds to check your readiness. You are sopping wet.

Donnie lines up to your entrance and pushes. You watch in fascination as his dark cock disappears into your warmth. He’s thick, no doubt, but the length concerns you. It takes some time and a lot of give and take before he gets all the way in.

It’s a bit painful when he first starts to thrust, but he goes easy on you while you are still adjusting.

Soon, you are both moaning. Donnie is blown away. He knew it would be pleasurable, but he had no idea that it could feel like this. Now he gets why cock warming is such a thing. Your body is so warmth and welcoming, like a comforting hug around his dick. He could stay here forever.

Later, he will be embarrassed that he didn’t even attempt any foreplay. Right now however, he’s in ecstasy.

Before long, you are panting his name as you cum around his cock. His eyes nearly bug out when your inner muscles squeeze him. He picks up his pace and when his orgasm starts building, he lets loose. His hips are pumping fast, he’s pounding your cervix and the pleasure-pain of it is driving you higher again.

When he cums, it’s explosive and messy. There’s just so much and it’s leaking from your battered hole. Donnie grins in triumph.

He cleans you up, and then takes you to his room. He spends the next couple of hours enjoying all your body has to offer, and you fall asleep more than satisfied.

The next morning, he lets you sleep in, and heads to the kitchen for some coffee. He feels better than he ever has and he knows it’s because of you.

He enters the kitchen and grabs his favorite cup. His brothers are all grinning at him. Your scent is all over him.

“Well, how was it?” Raph asks.

Donnie frowns, “How was what?”

“The sex, bro! How did it go?” Mikey pipes up.

Donnie’s jaw drops.

“Come on, man. You don’t think we’re that dumb, do you? It was obvious why you were getting us out of the lair last night,” Leo laughs.

Donnie clears his throat, and turns to pour himself a cup of coffee. His brothers wait expectantly.

He goes to leave the kitchen, and calls over his shoulder, “A gentleman doesn’t kiss and tell.”

Thirty seconds later, he comes back in and pulls out a chair to sit.

“Good thing, I’m not a gentleman.”

Michelangelo

Mr. All Heart tends to go with the flow.

So when things start getting hot and heavy, he embraces it and rides the wave.

He wants you, there’s no doubt about that. He has for a long time. But he likes to let things move organically at their own pace.

When you are ready, he will be ready.

And while he understands the mechanics of it, he expects to need your guidance and is totally chill with that.

It’s a Netflix and chill kinda night. You two are cuddled up in his bed, eating snacks and stealing kisses.

The movie you picked has an unexpected steamy scene and your cheeks heat up. Mikey notices that the hand he’s holding is starting to feel damp.

He glances over and realizes that you are getting hot and bothered. Just to test it, he leans close and places a soft kiss on your neck.

Your swift intake of breath and the clench of your thighs tells him all he needs to know.

“Hey, you wanna try it?” he asks softly.

Your eyes are wide but you nod eagerly. You want this. You want him.

With a smile, he pulls you underneath him, and starts off with some slow kissing.

Hands wander and clothes come off, but it’s easy and gentle. You both want to take your time and savor this.

Mikey is fascinated with your smooth skin. He touches, he tastes.

When you reciprocate, he lays back and watches you explore his body.

When you kiss the heart mark on his lower plastron, he whimpers. When you take him into your mouth, he moans.

As much as he loves it, he really wants to be snuggled tight in that pussy. He urges you to sit up, and helps you straddle him. You angle your hips and take him in slowly.

Oh shit, oh shit, oh shit! Mikey squeezes his eyes shut tightly. He had no idea it was gonna feel this good. How is he supposed to last??

He asks you to wait a minute once he’s fully seated inside you. He takes some deep breaths and tries to remember meditation training. It’s isn’t working.

He makes a mental note to work on that later.

For now, he wants to make sure you enjoy yourself too. You lean forward with your hands on his chest and roll your hips. Your clit rubs against the rough edge of his plastron and damn, does that feel good!

You start riding him harder and he gasps and groans. “Babycakes, slow down! I’m gonna cum too soon if you keep that up!”

You are chasing your own orgasm though and you know you are getting close. “Close,” you manage to gasp.

Thankfully, he understands and begins bucking his hips. “Yes!” you hiss, bearing down.

Mikey’s brain is mush right now. Nothing else matters but the way you are taking your pleasure from him and looking like a fucking goddess while you do it.

When you cry out, legs trembling, he grasps your hips and slams up again and again until he is left panting and empty.

After a snack fill-up, the two of you end up in round two.

The next morning, you both come out of his room and head straight to the kitchen. The others, who were enjoying breakfast, stare in disbelief at you in nothing but Mikey’s hoodie, a few hickeys marking your neck and thighs.

You grab a breakfast bar and some juice, scarf it down and then announce that you are headed to the shower.

As soon as you are out of sight, Mikey grins, dances around, and loudly announces, “I got laid, suckas!”

Then you peek back around the corner and look pointedly at your boyfriend.

“You coming?”

“Not yet,” he quips. “But I will be soon!”

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