New.

“h-hurts.” you whined, and issei just grunted in response, too caught up in the way your pussy twitched around just his head.

“it gets easier. you know it does.” he finally breathed.

first you wanted him to take you dry, barely letting him through the door before pawing at his cock.

now you were whining at him to slow down.

he figured the best option was to clamp a hand over your mouth, letting those high strung wines hit his palm. but you didnt want that, moving your head away from him, tongue reaching out to lap at his fingers.

“ahhh.” he chuckled, of course.

he popped two fingers in, pressing them down on your tongue, letting you play with the metal adorning his fingers.

the image of your spit covered lips sucking earnestly on the rings littering his hand all but broke him.

he pushed in, fighting the unforgiving softness of your cunt, seeing your pussy stretch to accommodate his big cock had him suck in air.

he kept going, slidding in against your muffled cries, face wet with fat tears, sinking until he was met with an ungiving wall, even then testing it, prodding at the sponge there.

it hurt so bad, so bad but the fullness and drag of his dick stretching your poor cunt was worth it.

you were already gushing, and with a couple thrusts you were gone, legs kicking as you tried getting leverage on the bed, hips pathetically humping him, trying to get away and closer all at once. you didn’t know what you wanted, just knew that you were cuming real hard.

even if it was a tight fit you’d know you were made for him.

your hearing dipped out for a second thanks to the utter pleasure of your pussy trying to clamp down on something too big, warm and pulsing inside you.

“g-gah! god, issei!”

the splatter of your cum against his balls and the bed was loud, made you feel dizzy and spent.

it was something he wasn’t ever going to get tired of.

he popped the fingers out your mouth, hand drenched with your drool to grab your legs, pulling them up how he wanted.

you’d have your fun and now it was his turn.

“fucking little cock slut.” he grunted, using his weight to pump his hips in and out of your still gushing hole. your orgasm was only exasperated by the sudden force, spray after spray of your cum drenched his thighs and balls.

“rintar- ohhhhh.”

your face, just like all the others, scrunches up in just the right way that lets him know it hurts. he sees tears forming at the waterline as he sinks his cock further and further into your little hole. 

a hand pushes on his chest, momentarily stopping him. he raises a brow at you.

“it’s too deep.” your eyes are locked on where he’s halfway inside of you. “i can’t take it all right now...”

“shh, baby...” he keeps going, making you squirm. “let me just...”

“n- no!” you choke out as he sheathes himself fully, hips flush against yours. 

“yeah, just like that.” he groans, head falling. “squeeze me just like that, you’re like a fucking vice.”

“rintarou!” you cry as he presses his hands on your legs, spreading them wider. “it hurts!”

“i know, baby, i know...” he pulls out a few inches just to press back in. “i like it when it hurts, though fuck.”

you throw your head back, tears falling down your face as he fucks your aching pussy. it stings as he bumps your cervix with each full thrust. moans of pain force their way through your throat, and suna mistakes? them for pleasure, going faster and fucking deeper. 

“you’re good...” there’s a squelching sound every time he thrusts in. “you’re a good girl for me, y’know that?” 

through your upset, your heart clenches at his words. “i- i am”

“‘course...” he leans over so he can sloppily kiss at your mouth. “you’re making me fucking cum, shit.”

you feel him burst inside, cum leaking into your cervix and pouring into your womb. your legs involuntarily wrap around him, trying to bring him closer as your body begs for his cum. 

i feel like he has a real “traditional” mindset as well. 

he doesn’t care if you’re his sister, you’re supposed to be a housewife. you’re supposed to serve the man of the house, even if it’s your brother. he’s just training you for what a man will really want.

so when he comes home from work, you better have dinner on the table and be ready to get fucked afterwards. 

he loves breeding you, something about his dear imouto-chan having her holes torn and leaking white makes him ready to go again. he’ll fuck you in the morning and expect you still have his cum inside when he gets home so he doesn’t have to prep.

there’s a ringing in your ears.

you wonder if that was an omen of what was to come, because not even a moment later you’re slapped back into reality. 

“don’t space out now, bitch...” his voice is loud in your ear. “i’m about to cum and i don’t want you making a mess. tighten up your dumb cunt.”

you nod, breath hitching and uneven. “sorry, senpai...”

“fuck...” he groans, pulling on your hair. “yeah, just like that, clamp down on me stupid bitch...”

you begin to cry again, feeling his cock dive into your cervix over and over. “please...”

“there it is, there it is...” he groans aloud. “i’m cumming.”

and he does, spilling all inside you. you’re quick to tense, trying not to make a mess. sakusa-senpai hates messes

“keep it in there for me.” he says as he pulls out of you. “i’ll beat you if i find out you’re being ungrateful.”

but frfr...... issei-nii hits different.

you want to help your nii-san, don’t you? he’s just so hard... he doesn’t want to be hard anymore... you’ll help him take care of it, right? please?

“no, nii-san...” you shifted in bed, trying to push him away. “i don’t want to.”

“please?” he pouts, cock already out and aching to be warmed up by you. “just the tip, please? it won’t hurt that bad.”

you pout, too concerned about what might happen if you’re caught. “fine... just the tip.”

he is so happy at that, pulling your underwear aside so he can get inside of you. even if he was being truthful about just the tip... he’d already forgot about all that. the second he gets his head in, it’s free game.

once you get home, you’re literally on fire. you’re short circuiting, twitching and pulling on his sleeve, mumbling and stuttering about how you just want it out, want it out, issei-nii, please!

“couldn’t handle it, huh?” he grins, put his hands up your skirt. “my poor little sis...”

“nii...” you’re crooning as he pulls the vibrator out. you stare into his eyes, wincing and moaning at the warm, stinging feeling of it coming out of your cunny. it’s soaked in juices and slick, and god you’re so sore...

“such a mess,” he laughs. “i really did you in.”

“hurts, nii-san...” you can barely stand on your feet. “hurts so much.”

“it does?” he croons, fake pouting. “well, i know how to make it feel better.”

“huh- uh!” you nearly scream as he presses you against the wall, taking his cock out and shoving it inside of you. “no, nii-san!”

“shh, it’s okay,” he coos. “doesn’t it feel better already?”

“n- no, hurts...” you squeal. “i can’t... can’t take it!”

“of course you can, you’re a big girl aren’t you?” he hugs you close to him. “now, m’just gonna cockwarm for a while...”