Chapter Text
Leon had never been the best with girls. It wasn't his fault - really! He just had a habit of coming off a little creepy, definitely came on too strong when he was trying to ask girls out. He fell hard and fast, convinced he was in love with a girl if she was so much as nice to him.
He'd been rejected more times than he could count, leaving him a little bitter. He's in his twenties, and he hadn't even had his first kiss. It was fine… totally fine. He wasn't mad about it at all. Women just didn't understand how nice he was. He'd treat his girlfriend so well if a girl would just give him a chance!
He's started to give up on his exploits, coming to terms with the fact he'd probably just die a virgin. That is, until he's blessed with a miracle. Must be divine intervention, he can't believe he got this lucky. His dad ends up telling him he's getting married to the woman he's been seeing for a while, and drops the fact that she has a daughter that's just a few years younger.
He meets you at the wedding, and he's instantly sure you're the one. He's pretty chill for the first few weeks that you two start living under the same roof, him as your sweet step-brother. He always dotes on you, takes you out for rides in his patrol car and takes you shopping.
He deserves a reward for all of that, right?
Well, he doesn't want to scare you off. Not when you're the first girl to actually give him attention. Doesn't matter that you're his sister now, you're so sweet and cute. His cock throbs every time you smile at him, and he's starting to get used to the perpetual erection he sports in your presence.
He starts off pretty slowly. Offers to help you out with your washing, pocketing a pair of used panties for later and washing the rest of your stuff. Holds them up to his face when he's alone in his room at night, inhaling the scent of you and rubbing his cock raw, cumming over and over until it's practically just water and his dick has friction burn.
The only issue is once he starts, he finds it hard to stop. It escalates pretty quickly. He starts spying on you in the shower, one hand rubbing his aching cock while the other records you washing yourself. He likes the souvenir, and he needs the material for when he can't sneak in to watch you.
He ends up completely cutting out porn. Why would he need it? He's got enough material of you to keep him busy for a while, and he makes it his passion to gather more. Starts sneaking into your room when you're sleeping just to slip your panties to the side and get some close-up shots of your fat, juicy pussy.
The only problem is, he keeps getting bolder. You've almost caught him so many times, and he knows he has to move quickly before you catch on. He flirts with you jokingly a few times, pushing down the anger that bubbles in his chest when you make a remark like ‘ewww, you're like, my brother, Lee. That's so gross!’.
Fine. If you didn't want him, he'd take it into his own hands. It was honestly way too easy to slip a sleeping pill into your night-time tea. You had been living together for a good 6 months now, and you trusted him more than anyone. He smiles sweetly when he brings it to you before bed, ruffling your hair playfully before saying goodnight and heading to his room.
Not that he stays out for long. He's sneaking back into your room a few hours later when he's sure your parents are sleeping. He walks up to your bed, phone in hand - there's no way he's missing out on getting this on camera.
“Hey, sis? You awake?” He asks softly, grabbing your shoulder and shaking you. He grins widely when you don't budge, sleeping peacefully with one of your legs thrown over the cover. He really is so grateful you sleep in nothing but a shirt and panties. Makes this whole thing a lot easier.
His hand reaches out to touch your bare thigh, palm sliding up your soft skin. His blood all rushes to his cock, and it's already twitching eagerly in his sweats, leaking enough pre-cum that a wet spot forms in his boxers.
His eyes stay locked onto your face as his fingers graze your panties. His breath hitches when you let out a deeper breath, and he stills to make sure you're not waking up. When he's sure the coast is clear, he reaches for the hem of them and slides them down your legs carefully, phone camera trained on your legs while his eyes refuse to look away from your face. He can't afford to get caught, not yet.
He's leaky and dripping when he finally gets your panties off. He moved slowly, not willing to risk anything. He's a bit bolder now that you're exposed to his eyes, taking in how pretty you are. His breath stutters in his chest, his eyes wide and lips parted.
He dips two of his fingers between your folds and spreads your lips to give him a good look at you. He makes sure his phone stays angled at you, not wanting to miss a second of this. He slides his thumb along your clit clumsily, trying to copy what he saw in a video online one time. He suppresses a whine at how wet it makes you, arousal dripping down and making his thumb all sticky.
He can't wait any longer. He sets his phone down to wriggle out of his sweatpants and boxers, kicking them off and letting them drop to your floor. He settles carefully on the mattress between your legs, gripping your thighs to spread your legs a little wider, careful not to jog you too much.
He moves a hand to the base of his cock so he can position himself at your entrance, his eyes unable to tear away from the sight. He's forgotten about his phone which is still recording face-down in the sheets somewhere. This has all of his attention now.
He can't help but moan as he pushes the tip past your entrance. You gasp softly in your sleep, shifting slightly. He doesn't notice. He also doesn't really care, to be frank. This feels too good to worry about anything else - the way your tight, wet heat engulfs his length inch by inch. He couldn't think about anything else if he tried.
He fills the familiar tightening of his balls as he fully pushes into you, his eyes widening as he moans again, his cock twitching as he cums inside of you. His breath catches in his throat, and he just stares down at you for a few minutes.
“Fuck…” He murmurs, voice cracking slightly. He's still hard - he's not sure he could ever go soft with you wrapped around him so nicely. But he didn't think he'd cum that soon. His cheeks are a bright red, and he's glad he decided it would be better to have his first time while you were asleep. That could have been embarrassing.
He starts shifting his hips, whimpering at the sensitivity he feels from just cumming. His eyes water slightly, but the tears don't fall past his lash line. He has to bite his lip to make sure he doesn't moan too loudly. He couldn't imagine waking you up like this. Or worse, his dad or your mom.
“Mmph… I'm so sorry, sis.” He whimpers as he starts to move faster, his hips rabbiting back and forth. His movements are sloppy and clumsy, every thrust pushing more of his cum out. He can't help but shiver at the sight, quickly fumbling for his phone so he can capture it.
“Couldn't help it.” He says weakly, voice breathy as he continues to fuck you, causing you to rock gently on the mattress. “You look… ah, fuck… so pretty. So nice to me…”
One hand grips your hip to steady your body as the other shakily holds his phone, recording the slip of his cock in your wet pussy. You're dripping all over his length, making the prettiest little gasps and whimpers despite being asleep.
“See baby?” He murmurs, leaning down to kiss the back of your neck, shallowly thrusting in and out of you. He's already close again. Fuck. Why did you have to feel so good?
“Even when you're asleep, your pussy sucks me in… fuck… s'good. Best thing I ever felt…” He whines, thrusting harshly into you now, gripping your hips tight as he stares at the way your face scrunches up, checking for any signs of the pills wearing off.
He cries out your name as he cums again, his brows furrowing as he buries himself to the hilt in your tight cunt, shooting thick ropes of his cum deep inside you. Finds himself hoping you're not on birth control. If he can get you pregnant, you'd have no choice but to be his... right?
He shakes the thought away, pulling out of you with a whimper. He leans down slightly, recording your puffy pussy for a few seconds as his cum starts to drip out before shutting off the phone camera.
He just stares at you for a while as you leak his cum, the sight making him hard all over again. It almost physically pains him to clean it up, but he knows he has to. He can't have you catching on to what he was doing too early. He doesn't want to risk his chances of doing this again.
He cleans you up carefully, making sure that no sign of what happened remains. He pulls your panties back on carefully, patting your ass gently before giving you a loving kiss on the cheek and scrambling off to his room.
He doesn't let out the breath he was holding until he's safely tucked back into bed. He jerks off to the video he took, pouting when he realises he was too distracted to record him sliding in for the first time. He sighs, but continues watching the video, cumming for the third time that night before going to bed.
He can tell you wake up sore the next morning when your brows furrow as you sit at the kitchen counter, confusion written all over your features.
Ever the doting brother, he offers you a sweet smile and slides a cup of tea over to you, tilting his head with feigned curiosity, as if he didn't know exactly what that face was for.
"Everything alright, sis?”