#trigger:painal

[kingkatsuki]

Barely got his GED hard working Kaji who helps keep the streets safe finally has a girlfriend now that he's in his mid twenties. Hard to get one when he always has headphones on or a sucker in his mouth but more and more he found himself placing his headphones by his neck music playing softly until it didn't play at all as he hoped to hear your cute voice better.

But now that he's got you underneath him, finally about to lose his virginity that he lied to you about the tip of his leaking dick slides into the wrong hole

If we’re on this wrong hole hype today I won’t survive it.

Warnings: 18+, virgin!Kaji, wrong hole, painal.

Word Count: 0.8k.

It’s not his fault, and you can’t blame him when you look this pretty beneath him. Your lips pouty and bruised from his rough kisses, cheeks flushed with heat and your chest heaves with anticipation. Your fingertips leave sparks of electricity across his skin as pretty manicured nails drag up his sternum to curl around his neck, desperately trying to pull him down for another sultry kiss as you whine his name against your lips and he’s certain he won’t survive this.

Kaji’s cock feels hot and heavy where it rests against your pelvis, leaking thick globs of pre that drool down the swollen tip and leave pools against your skin. He’s far too amped up and needs to ground himself, or he’s certain he’ll cum with the first sensation of your warm wet heat wrapped around his cock. If you were that tight when he slipped two fingers inside, he’s not even certain you’ll be able to take his full length. But god, he wants you to try. He wants to feel every single inch of you wrapped around his cock, clamping down around him like you had his fingers when he pushed you over the edge. God, you look so pretty when you cum—

“Ren,” You’re practically mewling now, the saccharine lilt to your voice sends a jolt directly to his cock, “Please, I need you.”

You need him, and he needs you.

Kaji hisses as he wraps himself in a fist, giving himself a cautious pump to try and allieviate the tension that sits in his pelvis as his balls threaten to empty all over you before you’ve even started. He had to push your smaller hands away moments earlier because the moment he felt your soft palm wrapped around his length his hips were bucking uncontrollably as he exercised every ounce of restraint he’d built over the years to stop himself from coming undone.

He chances a stroke through your sopping heat, dragging his leaky cockhead through your messy folds as you soak him in your slick. His lashes flutter as he has to close his eyes when your pouty lips part in a sultry whine as he knocks against your puffy clit, and you look so utterly fucked out beneath him when he hasn’t even breached your little hole.

“Fuck.” He mutters beneath his breath as he tries to focus, fingers tangled in the sheets by your head as he swallows thickly, Adam’s apple bobbing as he feels his slick tip catch against your entrance.

Your hips buck wildly at the contact, trying to coax him in and Kaji ruts his hips forward with a guttural grunt. The heat that engulfs him is tight, and he covets the sensation, despite the fact it clouds his brain and and has his heady balls throbbing for relief.

“Ren— fuck,” You cry out, and he panics.

He’s heard it hurts the first time, so he expects you to feel an ache from the stretch. Leaning down to pepper kisses against your jaw as the change of angle has him pushing another inch inside you, thankful his cock has leaked so much pre.

You’re squeezing so tight, and he can’t stop himself as his cock jumps. Pulsing with need as he finds himself succumb to the pressure that roars inside him, unable to hold on as he moves his hand to your hip, his upper lip doused with sweat as he tries to remember to breathe—

“No, ow— wrong hole, Ren.” Your pretty nails are clawing at his chest, leaving messy crimson lines against his pale chest as the painful ebb pushes him over the edge.

He can’t stop his hips from bucking when he cums, spilling his hot, thick spend into your unprepped asshole as he barely manages to pull out. More pearlescent ropes of cum land on your slit and pelvis as he moves back as though he’s burnt you. Wide eyes now glancing down at you with worry as he sees the look of pain that morphs your pretty features, teeth biting down on your bottom lip as he hates how his body reacts— you’re in pain and it still has his spent cock throbbing with want.

“I’m sorry,” He whispers, pressing lingering kisses to your warm cheek as he smooths calloused palms along your sides.

“It hurt,” You gasp out, thick tears clumping in your lashes as you stare up at him and oh god, he really is a sick fuck for getting off on it.

And what makes it even worse is the moment when Kaji pulls back to glance between your parted thighs to check if you’re okay and he sees what he’s done. Your tight, fluttering asshole pushes out the thick globs of spunk he’d pumped inside you moments earlier, drooling down the curve of your ass and pooling on the tousled sheets beneath you. It takes every single fibre of his being to stop himself from reaching out to push the moisture back inside your abused little hole.

“I’m so sorry, baby.” He coos, “I didn’t mean to—”

But he’s not really sorry, not even close.

[kingkatsuki]

There is something so funny about poor Sakura accidentally fucking your ass and not your pussy 😭😭 you tried your best, baby boy

I KNOW because think about how long it took to get him here?!

The number of times he’s unravelled with the slightest touch, creamed his pants from the sight of your bare breasts or naked cunt. The crude words that slip out of your pretty lips that are a complete contradiction to how sweet you look.

You let him take the reigns, brows furrowed in concentration as his lips curl into a determined pout, dragging his leaking cockhead through your messy slick until he feels it catch against your entrance and he tries to remember to breathe. It’s not his fault he has to screw his eyes shut to stop himself from looking down at how debauched you are beneath him, sultry eyes gazing up at him enticingly as he tries to remember to fucking breathe.

He’s so close to you this time, he’s got to take the leap before he finds himself fucking his fist and spilling his spunk all over your tummy again. So he positions himself, feeling the resistance as he takes a deep breath and ruts forward with purpose. With his eyes clenched shut he can’t see the way your face contorts in pain, or the way you reach out to claw at his forearms. He’d expected you to be tight, but he didn’t expect this.

“No, not that one, Haruka.” You whine, shifting beneath him which only has your tight hole clamping down around his tip with a vice like grip.

Sakura knows he’s fucked up, and that should pull out— but how can he when he sees the flushed tip of his cock buried inside your tight rim as your glistening cunt practically drools all over him. You’ll probably call him dumb now, and never want to see him again.

And it’s pathetic how close you have him coming undone again. Locking his jaw as he prepares to pull out, cheeks flushed a deep crimson as he’s barely able to murmur a gruff “sorry” before he notices your prettily manicured fingers slip down to where your bodies are connected as you rub persistent circles against your puffy clit.

“J-just, give me a sec, ‘kay?” You gasp as he shifts his hips, trying to etch away the pain with pleasure as you trick your body into relaxing, “I think I can take it.”

[kingkatsuki]

Well now you have to share those wrong hole thoughts with the class!! 🥹🥹

I don’t even know where to BEGIN.

Inexperienced Sakura who is so nervous and awkward that he blindly thrusts into your poor ass.

Smug Togame that loves to slip you a pinky when he’s fingering your cunt because he adores the shocked gasp that sounds from the back of your throat at the motion.

Mean Sanemi who pretends he doesn’t realise he’s pushing the fat tip of his cock into your poor, unprepped asshole when he’s got you bent over in front of him.

Endeavor convincing you that it’s not cheating if he fucks your asshole.

Drunken fumbles where he accidentally ruts into your ass.

Or he’s got you bent over for him, fingers buried deep in your cunt as he coos about making sure you’re prepped for him— all the while he’s watching your tight rim flutter invitingly for him as he barely gifts you a glob of spit against it before he’s forcing his cock into your asshole.

But also just the thought of a man being completely engrossed in how good you feel that even when you tell him “no, not that one!!” he just can’t stop himself? I’m on the floor.

[kingkatsuki]

Meany kiri as a waxer! He gets so hard when you wince. Or push your lips together as your eyes water and if you moan or whine?? Honey he’s adding a massage on to your spa day. Gonna massage your insides with his cock. (And makes you pay the fee still lol)

“Aww, come on sweetheart. It’s not that bad, is it?” He’d coo down at you when the tears are pooling in your lashes from the pain.

He wonders if you’re doing this for yourself, or if it’s for a guy- jealousy immediately flowing through his veins at the thought of someone else getting to see this perfect pussy.

His fingers stroking along the now smooth skin before reaching to the other side, telling you to take a deep breath before he pulls again. God, why did you have to sound so pretty like that? Now all he could think about was hurting you to have you make that sound again. Maybe he could slap your slit-

“Did I hurt you?” He asks, an air of condescension in his tone as his fingers begin to massage the dips of your pelvis, at the junction right near your folds. Digging into the skin as he deliberately tries to spread you open for him- trying to get a better look at your tight little hole. And we’re you wet? The slightest hint of moisture leaking between your thighs as it shone beneath the angry spotlight above him that helped him work. Were you getting off on this?

[pemdas-isamyth]

pathetic boys are the best

There is something so funny about poor Sakura accidentally fucking your ass and not your pussy 😭😭 you tried your best, baby boy

I KNOW because think about how long it took to get him here?!

The number of times he’s unravelled with the slightest touch, creamed his pants from the sight of your bare breasts or naked cunt. The crude words that slip out of your pretty lips that are a complete contradiction to how sweet you look.

You let him take the reigns, brows furrowed in concentration as his lips curl into a determined pout, dragging his leaking cockhead through your messy slick until he feels it catch against your entrance and he tries to remember to breathe. It’s not his fault he has to screw his eyes shut to stop himself from looking down at how debauched you are beneath him, sultry eyes gazing up at him enticingly as he tries to remember to fucking breathe.

He’s so close to you this time, he’s got to take the leap before he finds himself fucking his fist and spilling his spunk all over your tummy again. So he positions himself, feeling the resistance as he takes a deep breath and ruts forward with purpose. With his eyes clenched shut he can’t see the way your face contorts in pain, or the way you reach out to claw at his forearms. He’d expected you to be tight, but he didn’t expect this.

“No, not that one, Haruka.” You whine, shifting beneath him which only has your tight hole clamping down around his tip with a vice like grip.

Sakura knows he’s fucked up, and that should pull out— but how can he when he sees the flushed tip of his cock buried inside your tight rim as your glistening cunt practically drools all over him. You’ll probably call him dumb now, and never want to see him again.

And it’s pathetic how close you have him coming undone again. Locking his jaw as he prepares to pull out, cheeks flushed a deep crimson as he’s barely able to murmur a gruff “sorry” before he notices your prettily manicured fingers slip down to where your bodies are connected as you rub persistent circles against your puffy clit.

“J-just, give me a sec, ‘kay?” You gasp as he shifts his hips, trying to etch away the pain with pleasure as you trick your body into relaxing, “I think I can take it.”