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The boy could stop a heart with his stare

Yes I should be working on prompts (which I am) but this has been nagging me and I wanna write it out so enjoy. Here are some First Time™️ headcanons and how it might’ve gone down with a few realistic blunders here and there cause yes.

Needless to say nsfw under the cut

Leonardo

Ok so fearless himself first experience isn’t all the way of you catch my drift.

No seriously the first thing that happens for him is a blowjob which isn’t exactly how he expected his first sexual experience to go down like (was that a pun? wow)

Necessarily isn’t a bad thing, but let’s be clear Leo has that idea of the typical first time events, the candles, the ambience, all nervous touching etc

But then again Leo never expected to even get to experience having someone fall for him let alone want to be intimately involved with him

And it’s so out of the realms of how he dreamt or fantasized about it. Because his s/o catches him off guard.

It happens at Vern’s fancy af penthouse(all that Falcon money you telling me they ain’t hanging out there, he owes them lol)

But yeah it’s one of those get together nights, the gangs there with Ape and Casey. Musics playing, Casey set up beer pong, everyone is so engrossed in the game that when Leo slips out to find the bathroom he’s a little startled when you grab him and gesture him to be quiet

He’s even more startled when you get into the bathroom with him and kiss him like you haven’t seen in weeks.

It’s somewhat subtle cause you’re gonna run your hands down that plastron and admire how broad and strong he is and Leo absolutely eats that shit up he LOVES when you admire him and compliment his strength and hell even his looks

Leo’s brain becomes white noise when you get on your knees though and your hands reach the hem of his pants and there’s several heartbeats where you wait for him to say ‘keep going’ and all Leo can do is just nod, grip the sink behind him as a shyness takes over him when he feels his pants slide down

There amongst the music and group banter just a few feet away hes in some fancy bathroom with his s/o on their knees engulfing him and gripping him and honestly Leo’s meditation skills go out the window.

It’s not that long of an experience honestly and Leo is embarrassed that he couldn’t hold out a little longer, he’s also worried he didn’t warn you in time that he was about cum but you seem to handle the situation with grace and give him a smile even as you cough slightly. It really makes him flushed cause you look so beautiful right then and there and the two of you start giggling and laughing cause it just such a left field situation. It catches him even more off guard when you pull him down for a kiss and that intermingle taste of himself and your mouth hooks him.

Donatello

Listen I’m gonna catch flack maybe for this but Don’s the first out of his brothers who actually goes all the way with his s/o like fully

And it happens in the truck and it’s so unplanned because neither him or you expected the drive to end like this.

It’s a midnight roadtrip that takes the two of you through the more rural side of NY. This is Donnie’s way of clearing his head m, he loves driving so when he adds you to the equation it’s even more perfect.

The trucks been parked for a bit now and it’s not uncommon for y’all to makeout and be all lovey with one another

But on this particular night, the powers that be have you right on Donnie’s lap and that sweet makeout has turned a little more scandalous than usual.

Donnie’s no even sure to this day how it escalated to the degree of pants being pushed down and underwear disappearing but it happens and soon enough with each other’s consent to progress he’s inside of you and your running the show cause he’s terrified he’ll mess up or cum way too fast.

Surprisingly enough it goes really well, With minimal to no hiccups, the most being Donnie rubbing a little too hard on your sensitive nub/tip. He manages to last a decent amount of time (probably doing complex equations in his head to distract himself)

The aftermath is a little awkward although you’re both all shy smiles with “was that good?” “Did you like it?” etc and Donnie is gonna have to sneak his way into the bathroom once he’s home cause there’s a mess of stains on his pants.

Michelangelo

Also unplanned, more so literally an accident

It’s not the full experience of going all the way

Cause Mikey and you are hooked on kissing and pawing but it never truly escalated further than that

Until today of course

It’s the usual heated makeout session but your both on his bed, there’s music playing and the two of you progressively get bolder

The best way to describe it is basically dry humping. Dont tell me that wouldn’t be the way it goes down with him.

He feels you grind against him as the two of your feverishly kiss and Mikey’s already feeling a little too hard. Almost unvonsciously you both rub against one another, each grind and grip and kiss making the two of your too warm. Before you know it your both pressing your forheads together, thrusting against one another.

The first time you hear Mikey moan makes you moan right back against him, that alone causes his hips to stutter. It’s his ‘ohmygod’ that you basically swallow that makes you grip him so close to you, the trembling of your body as you muffle a long moan against his lips and Mikey cums, hard, in his shorts to the feel of your shaking figure shooting all that delicious oxytocin all over your body

You’re both so hazy and weightless when you come down from it. Mikey’s sheepish but tired smile so adorable, you two can’t seem to find a reason to disentangle from one another

Raphael

Raph is actually super Nervous™️ because he’s got a pretty big idea that things are gonna get heated cause you’ve been pretty vocal about it

But alas this boy has got some major body issues (they all do but it do be hitting him hard when he with you) cause you’re so perfect and pretty and he doesn’t want to harm a hair o your head

And for a huge FLIRT™️ he does get all shook up about not being able to deliver the goods, but alas you are there to encourage reaffirm and gas the shit out of him.

So naturally you make the first move and trust me he is so happy you did cause he was gonna pass out.

It goes down while he’s at your place and y’all watching a movie and for the past half hour you’ve been making cartography on his thigh and Raph honestly can’t even explain the first five minutes of this movie because he’s been on cloud nine since you started

You snuggle up closer to his massive frame and when you explore his inner thigh and press your lips to his neck, Raph is sure that he’s going to combust. You linger at the hem of his shorts and ask him if you can and Raph is embarrassed with how quickly he nods.

Raph seriously doesn’t understand how a simple movement like that (which he himself had done countless times) is just ten times hotter when it’s you. The softness of your hand gripping his already hard member and the way you bite your lip at the sensation of how thick he is

Raph sighs against your temple, he gets such a head rush with the first few strokes. Pride flows through him when he feels you struggle to jack him off one handed. But that quickly melts into shyness when you push his shorts down enough for you to be able to wrap another hand around his thick member.

There isn’t much of a hiccup, mostly that Raph barely makes a coherent sentence enough to warn you that he’s cumin, so there’s a mess and you know there’s no way your gonna get those stains off your couch.

He almost gets hard again when he catches you licking your fingers, giving him a look that puts him out of this realm of existence

99% of romance books about werewolves have Some Guy on the cover and it's just devastating to me what a missed opportunity it is. SHOW ME THE MEAT