PRETTY WHEN YOU CRY ˚ ༘♡ ⋆｡˚

PRETTY WHEN YOU CRY ˚ ༘♡ ⋆｡˚

ೃ⁀➷ pairing: sub stalker charlie x fem dom reader

ೃ⁀➷ warnings: stalking, masturbation, fingering, pre mature ejaculation, dacryphilia, overstimulation, humiliation kink, mean (ish) reader.

ೃ⁀➷ notes: this wasn’t supposed to be this long but enjoy…

you had just gotten in bed, with your hands in between your legs, right above your underwear as you heard loud rustling from outside your window. you knew it was charlie. you knew he would come to your window, watch you change, watch you touch yourself.

he wasn’t aware that you knew about his perversions, how he’d cum in his pants by just watching you squirm under your own touch. was it bad that you found it hot? the way he stalked you, the way he was completely and utterly obsessed with you. you’d leave your blinds open every night, just incase he wanted a show.

you and charlie had a couple of classes together and would talk every now and then. you had always found him attractive but you knew he was infatuated with you. you saw the way he looked at you, spoke to you, about you. you’d have to be dumb not to realize.

knowing charlie was right outside your window, you hand wasn’t enough. so you decided to ‘catch’ him.

you got out of bed, walking over to your window, you could hear charlie trying to climb off the ledge of your roof. you opened the glass to it see just who you thought it was, a guilty look painted on his face.

“what are you doing here char?” you questioned, playing dumb. charlie’s eyes scanned over you, you wore pyjama shorts that fell just under your ass and a tight tank top that he could see your hard nipples through.

“i-i can, i can explain myself.” he stuttered, panicking.

“go on then.” you told him. you crossed your arms over your chest, making your tits press together which drove him mad.

“i—”he muttered, he couldn’t even think of an excuse right now.

“were you watching me touch myself?“ you teased, your lips turned up into a soft smirk. poor charlie was so confused, he thought you would file a restraining order on him but it almost seemed like you enjoyed it.

“no- no i wasn’t i swear.” his tone was meek, begging to be believed, he even put his hands up, as if you were a cop.

“i’m not stupid charlie, you can tell me the truth. you’re not in trouble.”

“okay… i was.” he couldn’t look at you while admitting this.

“why don’t you come in my room char, it’s kinda chilly out hm?” you bit back a smile.

“uh, okay.” he crawled through your window, you closed it behind him. charlie examined every inch of your room, obviously he had seen it many times but never up close. charlie took in every detail of your room. he surveyed photos of you and your friends you had hung on your wall, little trinkets you kept, the products on your dresser.

you laid back down on your bed, propping yourself up on your elbows. you motioned for charlie to sit at the end of your bed, he obeyed.

“charlie?” you called, disturbing his train of thought.

“yeah.” he replied almost immediately.

“were you touching yourself while watching me?” you were driving him insane, but he deserved it.

“mhm.” he nodded, unable to meet your eyes. he felt so bad, so guilty, so pathetic.

“okay, well since you interrupted me, why don’t you watch me and try not to.”

“i dunno if i can.” he looked down at the his boner, poking through his sweatpants.

“kinda owe it to me char. i mean, i did just catch you stalking me, the least you can do is do what i say. plus i wanna hear you beg to touch yourself.”

“fuck.” he groaned. you giggled at him before pulling your tank top off, making sure charlie’s eyes were on you. the sight of your boobs right in front of him only made him harder, he wanted to touch them or suck on them, anything would be enough.

“bet you wanna feel my tits so bad huh? i mean you’ve been watching me change, jerking yourself off while looking at them. this isn’t the first time you’ve been outside my window.” you taunted. “gonna have to earn it.”

“how-how do i earn it?” he wasn’t even concerned with how you knew that he had been watching you for a while, just desperate to feel you.

“already told you char, watch me touch myself without touching yourself.” you pulled down your shorts to reveal the lacy thong you wore. charlie couldn’t help but notice the huge wet spot on your underwear.

‘you did like this.’ charlie thought to himself. he stared at you as you rubbed your clit over your soaked thong, teasing yourself with one hand, playing with your tits with the other.

“you’re so… wet.” charlie said in a breathy voice.

“mhmm was thinking about you char.” you told him. his eyes went wide,

“r-really? you were?” he smiled at you. charlie sounded so pathetic, you loved it.

“mhmm.” you nodded, slowly removing your thong. the sight of your body entirely exposed forced charlie to whimper.

“i-i think about you, like that, a lot.” he was struggling so hard not to touch himself, it almost hurt. at this point, your cunt was throbbing, desperate for stimulation.

“i know you have.” you replied before rubbing your clit in circular motions, humming in pleasure.

“can i um, can i touch you instead…like finger you? i won’t touch you anywhere else if i’m not allowed to yet.” charlie couldn’t bare just watching you. if he couldn’t touch himself, he wanted to touch you. “please?”

“not yet, be patient.” you spread your legs further apart, pumping two fingers from your free hand into your entrance slowly. “feels so fucking good, don’t touch yourself yet charlie.” you groaned.

“t’so hard not to.” he whined, putting his hands behind his back to retrain himself.

“i know, you’re so needy char. fuck!” you panted. both of your hands sped up, making your moans louder. you were squirming so much. charlie watched you closely, taking in every one of your sounds, movements, and expressions. he whispered compliments as you brought yourself closer to your climax.

after you came, you sat yourself back up on your elbows to see that charlie’s pants were wet. “did you cum in your pants? that needy huh, can’t even wait ten minutes?”

“i know, m’sorry.” charlie said shyly, he looked away

“i didn’t even touch you…you didn’t even touch yourself and you came, holy shit… you don’t get to touch my tits yet, couldn’t even hold off.” you let out a short scoff which was followed by silence. charlie was so embarrassed, not daring to look you in the eyes. he wished he could’ve just disappeared at that moment. “lay beside me char, i wanna see your cock charlie.” you purred. charlie followed your order, moving from the edge of your bed, next to you. “now show me, take off your shirt too.”

charlie nodded before swiftly removing his shirt. he then pulled down his sweat pants, exposing his cum filled boxers. finally, he took off his boxers to reveal his dick. he looked over at you, your eyes remained on his body.

“so perfect char, bet it’s really sensitive right now though hm?” you asked. charlie’s cheeks turned red at your compliment.

“thank you and yeah m’sensitive.” charlie responded.

you shifted your body so you were on your side, facing charlie. you tucked his hair behind his ear, bringing your mouth to charlie’s it you whispered, “i wanna make you cum again”.

charlie’s breath hitched, he couldn’t believe you were finally going to touch him. after countless nights of imagining that his hand was your warm, tight pussy wrapped around him or your soft hand pumping his cock, he was finally getting to feel you. “please make me cum again, please.” he begged.

“so needy.” you giggled, crawling downward until your lips met charlie’s sensitive tip. you placed short, gentle kisses on it, holding his shaft in your hand.

“oh my god, fuck.” he huffed, his breath heavy.

“i haven’t even started yet.” you nagged, taking your soft lips off his tip. while still giggling, you began slowly moving your hand up and down his shaft.

“mmm thank you.” a stupid smirk was plastered on his face as he watched you speed up your movements. after a few minutes, his chest began to rise and fall rapidly as his mouth hung open, high pitched and draw out whimpers leaving his lips. you felt his dick twitch in your hand before he came for the second time.

you took a second to think of a real punishment for him. as the idea crossed your mind, you immediately wrapped your mouth around his soft cock, feeling it grow in your mouth.

“wah- what are you doing? i, fuck, i can’t go again.” he babbled. you rolled your eyes in annoyance, taking your mouth off his dick.

“too bad isn’t it, didn’t i tell you that you owe me? charlie, you’ve been watching me, stalking me for weeks now. can’t you just do what i say?” your tone was weirdly calm.

“okay…m’sorry” he answered. you placed your mouth back on his now, painfully hard cock, hollowing your cheeks. “ahhh! it’s too much.” he moaned. unable to stay till, charlie began squirm and bucking his hips into your mouth.

“ohmygoddd please i’m sorry, fuck aughhh! i’m sorry for stalking you, it’s too much please!” his words were slurred, charlie didn’t even know what he was pleading for. tears began streaming down his face from overstimulation. you bobbed your head up and down on his cock at an increasingly fast pace, the room filled with charlie’s loud sobs and whimpers. you then felt that same twitch as before and as you suspected, shortly after, charlie’s warm cum filled your mouth, you swallowed every drop.

you returned back to where you laid before, watching tears flood from his blue eyes. “you look so pretty when you cry charlie”.

he turned towards you. “thank you.” he sniffed as you wiped his tears from his cheek. holding charlie’s jaw in your hand, you traced his cheek with your thumb. “you’re always pretty.” he spoke. the two of your faces were so close together, charlie brought his lips to yours, you kissed back passionately, feeling charlie grin against your lips. one of his hands found its way too the bare skin right under your boob. “can i um- can i?” he questioned after pulling away from your lips.

“go ahead.” you responded before attaching your lips to his once again. charlie cupped your tit in his hand, squeezing and kneading it.

“so fucking perfect.” he groaned before shortly pecking your lips.

“charlie.” you said, staring at him.

“mhm?” he mumbled, looking away from your tits and up at you.

“next time you’re outside my window, you can just come in.” you purred. your words forced charlie to whimper. he could do this again? touch you? maybe even be inside you? god he felt lucky.

“actually?” he looked at you with that pathetic smile.

“yeah, maybe you’ll get to touch more than just my tits next time.” you smirked at him, kissing him once more before he cleaned himself up, climbing back out of your window.

the next night, you heard tree taps at your window. knowing it was charlie, you opened the window to let him in. almost immediately, you began undressing each other between staggered sloppy kisses. the night ended in him sobbing after you rode him, making him cum five times, which left his cock red. he knew he deserved it.