#dark!dex

[angellicxx]

rooftop watcher

Benjamin "Dex" Pointdexter x Reader

Summary: Dex loves watching you from a distance, but hates not being able to give the pleasure you deserve from him.

an:This is my first ever published fanfic one shot so hopefully its not that bad. I've been obsessed with Bullseye edits recently and just needed to write a stalker fic.

warnings: Dark!Dex, stalker, f masturbation, cumming in pants, dark thoughts, Dex daydreaming and wanting to hurt a guy (he's so precious he would never)

w.c.: 1,300 (edited 5/25/25)

A fresh breeze of the city hit Dex’s face as he adjusted his binoculars. It was the perfect view. It didn’t take him long to find it. He only had to find a building adjacent to your apartment and with a higher outlook. How lucky he was for it to have an unlocked rooftop no one ever went to. It was almost like you were inviting him to watch you, not ever closing your curtains at night. Didn’t you know there were bad people who could see you living all alone? Thats why he had to be there. To make sure you were safe.

It was a late Friday night, and Dex was so proud to see you were staying home tonight, instead of venturing out into the unsafe city where it would be hard to keep an eye on you.

You probably would go out with your girlfriends in a skimpy outfit-- that sexy, black plunge top and skirt he loved so much, the one that showed your ass perfectly--all of it earning sinful gazes from prowling men in the night who would offer you drinks and a night at their apartment. He would have no other choice than to watch you blush and smile at them, too drunk to make a decision that was good for you.

If Dex had the courage he would be the man.

He was a coward, too unworthy to approach you. Instead he would just follow from a distance to make sure the guy didn't get any wrong ideas-- make any moves that made you uncomfortable. If he did, he would leave him bleeding in the alleyway, before asking if you were alright, if that man was going to hurt you.

Maybe he wasn’t-- but he would still earn your thankful praises.

A hero in the night.

You would be so grateful for him and insist on bringing him back to your place-- oh, that would be so nice.

But that wouldn’t happen tonight. No, tonight you had chosen to stay in and rewatch that show for the third time. Dex didn’t pay attention to the show, he was too busy adjusting the magnification of the lens to get a better look at your tank top and shorts. They must’ve been new and not worn in yet because they were just so tight.

In the faint glow of your dark room he would see your delicate nipples pushing at the fabric, your breasts stretching the cotton. The sleep shorts riding up your thighs as you mindlessly gazed at the TV under drowsy lids. How cute you were sprawled across your bed sheets for no one else to see but him.

Dex was getting agitated in the soft chill of the night. He deserved to be in the warm bed with you, holding you close as you smiled at the cheesy joke on the screen, caressing your soft exposed skin still fresh from the thirty minute shower you just took. Dex didn’t know what it was that made you switch on, but it snapped him back to his watching when he saw it.

Maybe it was an intimate scene on the television, or a passing thought of him, but a drowsy smirk played on your lips as your hand slowly slid down your chest and slipped down your shorts.

This was going to be a good night for Dex.

You were rubbing slow, soft methodical circles underneath your shorts. Dex prayed you would take them off so he could see your pretty pussy just once. It was unfair how you didn’t even take your clothes off. Dex wanted nothing more to see you naked—unfortunately you only ever seemed to put your clothes on in the bathroom.

Your other hand had dipped under the hem of your tank top, palming at your breasts as your eyes closed to your sensual movements. It only took a few seconds until you began to squirm, legs reaching out as your mouth fell agape to soft moans and whimpers.

His cock twitched beneath his pants, fighting the urge to take it out and stroke himself alongside you. But he resisted. He had to take in every moment. Dex noted to bring a camera next time.

Your hair sprawled out on your pillow, back arching to the pleasure Dex wished he could give you. if only you were kind and gave him a chance— it tortured him to the fact you hardly ever even looked at him.

Dex allowed his hand to fall to his hips, palming at the erection you selfishly gave him. He couldn’t contain his grunts of frustration as you fucked yourself, teasing him mercilessly from a distance.

You were a whimpering mess. How easy you got off, your sensitive self didn’t even need a toy.

He couldn’t take it, the thought that he could make you feel so much better. But tonight he would contain himself, and admire your needy form pleasuring yourself from a distance.

Dex couldn’t stop himself as his hips bucked into his hand in tandem with yours, his dick straining the fabric of his pants as he breathlessly fought to control himself. The form of your hand rutting underneath your shorts was enough to set him off completely.He could feel the pre-cum on the tip of his cock, white knuckling the binoculars so hard he thought he would break his damn hand.

You were so pretty, lips agape and body shuddering with your struggle to cum. Arms tensing as you fucked yourself all alone, whimpering to the dark air of your room. Next time you would be moaning his name into his ear as he did all the work for you. He would make you feel as good as he felt right now watching you.

You were close, fingers clutching your tit as you fingers moved faster under your shorts, legs straining to reach the climax he could give you faster. Your index finger was rubbing circles on your nipple from under the fabric, hip bucking into your hand at a faster pace. He could image in the lewd sounds of your moans and slapping of how wet you were. One final cry out and you became undone, falling back onto your mattress as you chest rapidly fell and rose, fingers still lazily drifting around your nerves to let the orgasm ride out.

“Fuck.” Dex breathed out and shuddered in the cold. Cum filled his boxers, sticking to his pants and hips as he gripped the brick boundary of the roof to steady himself.

Only you could make him so pathetically mindless to cum in his pants. Just imagining your tight body clenching aorund him and making him cum was almost enough to make him grow hard again.

When Dex gathered himself again to look back into your window, he was disappointed to see it had become pitch black, and you were lost in the dark to him. You must have grown tired from your orgasm and shut the TV off for the night, drifting off the sleep without him. He cursed himself again at how stupid he was to have looked away.

He couldn’t take it anymore. Perhaps tomorrow when you were on your morning run he would follow more closely behind. Maybe he would accidentally bump into you at the coffee shop you like so much and make a comment about the show’s upcoming renewal. The plan was all coming along, just so you could be together. Maybe tomorrow night you could get fucked by him instead of your lonely fingers.

He took one final peak and whispered a good night before he returned home.

“I’ll see you soon, darling.”

[thenightwinggf]

employees only

dex x f!reader

word count: 2.4k

summary

you are having a horrible shift, Dex is content to sit and grade papers for you.

tw for extremely toxic relationship dynamics & domestic violence: reader walks dex like a dog. stay tuned for my hc's about his antipsychotics

You hate your hotel. 

It is 1am. The issues started at midnight, really 12:02am. You know because while printing out the folio for your walk, you thought—I can run the audit after this, but you don’t get to run the audit after printing the folio, because your night is determined not to be that easy.

Occupancy is at one hundred, you are oversold by one. You had hoped that the silver tier member wouldn’t arrive and make your life easy, but your life is never that easy because not only does he arrive, but he insists on making every step of the walk progress difficult. He doesn’t want to go to the hotel you had called ahead at and verified availability, okay. That’s fine, he’s being relatively cordial about it so you help him. He doesn’t want to put down a card for the other hotel, you are firm: if he doesn’t want to put down a card, he needs to go to the hotel that you chose. 

Why couldn’t you call him?  He wants to know, because you don’t have a phone number on file. He isn’t listening, you’re just glad he’s gone. He eventually agrees to tap his card, your AGM will set up direct billing in the morning. That’s not the worst part.

That would be room  410’s  gnat infestation. You did not expect the sheer volume of gnats in the video that this guest is now showing you—a man who came up when you were discussing billing complications with aforementioned walk guest. 

You have no rooms to move him to. This is not good, this is horrible, this is your worst shift in recent record and you’ve had to evacuate the entire hotel before. They gnats had taken over the light above the entrance door, a black swirl of movement that was merely agitated when you attempted to take the housekeeping long lint-roller to the light, walls and doors in order to try and slightly fix the issue. It did not help, at all.

He says he noticed yesterday, but didn’t report it. He wants to be put into a different hotel, you cannot do that. 

You do not have raid, you have searched the hallway closet, the house person closet, the maintenance supervisors office, the back room, it is overdramatic to say you want to die, but you definitely want to smash your head against the wall until your face is imprinted. 

You are finally freed from trying to fix the gnat infestation, looking at your dashboard. You feel guilty, really, you hate nights like this—stuck between impossible situations. 

OOO. Out of Order. Room 201, What is this? out of 175 rooms, four floors, you have one room that could be used. You check the details, marked OOO by housekeeping supervisor based on odor, okay, you can work with that. 410 is begrudgingly sleeping in his room, he will have to be moved immediately upon the earliest check out but maybe, maybe you could just clean this room. You are trained in housekeeping, okay. You almost run to 201, skipping the slow and outdated elevator that multiple people have gotten trapped in (you refuse to be one of them.) you tuck the giant keyring into your pocket to stop the jingling as you begin to jump over multiple sets of stairs to reach the second floor, trying your best to close it softly behind you but a heavy door is going to make a noise louder than a clink when it locks as you tab your master key against the door of 201.

Once, twice, three times, “I’m opening the door.”

“I’m in here! It’s Christian.” You jump, half-thinking that you are hallucinating as you pause with the door slightly open, chain lock taunt as it stops you from opening the door any further.

Your General Manager is in an out of order room marked vacant. 

“Oh. Have a good night.” You do not ask, ‘what the fuck?’ Because years of customer service experience have taught you to always keep a level tone and with met with rejection, always ‘have a good day.’, ‘thank you.’ Rather than ‘you make over six figures and can’t pay for your own fucking hotel room?’ As you walk down the stairs in a haze of confusion and annoyance—now you can’t hide in the back room and grade piles of student work, now you had to pretend to work to keep up the appearance of being busy. 

By the time you’ve walked back to the front desk, Dex is there. 

He is halfway towards the door leaving to the back room, a place that you have lectured him on multiple times that he can not go because he is not an employee and now, you have caught him red-handed with his hand outstretched to push the door open. 

He must have paused when he heard your footsteps, as if he stood still enough you wouldn’t notice that he was once again, attempting to go into employee only areas. Tonight, you don’t really have the energy to lecture him. 

You know that he knows it’s wrong, that it’s not allowed—he just doesn’t care. Dex will nod along, apologize at the correct time, but you know that next time you do not immediately show yourself when he walks in, he will do the same thing. 

Sometimes you just like to lecture Dex for the thrill of game, really. It keeps him on his toes. Tonight is not that night. You know that it is useless to be disappointed, but you cannot hide it. Instead, you walk past Dex and hold open the door of the employee only area for him to hover in the entrance way, solemn as he plays when he has done something he knows is wrong, but does not particularly want to draw attention to it while simultaneously wanting you to absolve him. 

You gather ungraded work, stacking it neatly and evening out any papers sticking out from the stack before tucking away your laptop, then pull out the stack of papers that will eventually be a book that you are reviewing for a colleague then hand the ungraded work to Dex. On the top of the stack is the rubric and answer key, “Please grade these for me. I need to pretend to be busy in case my GM comes out.” 

Dex leans down, just slightly, he is too cute. You pat his cheek, once, twice, then trail your hand down his jaw, his neck, his chest above the loose black long sleeve and pat his forearm to get him moving.

You aren’t supposed to sit in the back, but it has never stopped you and no one has ever mentioned your habit to you. 

Really, you tried to sit in the restaurant for the longest time, then tried to sit in the far corner in the dark but had scared too many guests to continue. After years of testing out new positions to hide, you had eventually given up and decided it really was best to just sit in the back—avoiding guests who had weirdly quiet footsteps seeing you with your laptop. 

Dex does not argue that reading is not being busy. 

He moves from the door frame, sitting on the couch in front of the TV, in direct line of the front desk though from his angle he can’t see what you’re reading. 

He has the papers directly in front of him: answer key to the left, ungraded in the middle, graded to the right.

His natural state is obsessively observant, he knows that it is not you who needs to look busy, but him: the one who’s out of place, who doesn’t have a room and only visits the hotel because he hates that you work overnight. 

So intensely that Dex had once sent your immediate notice to quit via email when you were sleeping, your manager had replied by asked for additional time to hire a replacement and you had lied, managed to keep that fucking job.

He had thought you’d go along with him—that’s all you had to fucking do but Dex had a fundamental misunderstanding of your character based on what he wanted to see and you had thought it was time he woke the fuck up. 

You had been mad at him, but he had thought he could’ve smoothed it over. You just had to listen to him, see his point of view, how much he loved and cared for you and just wanted the best for you.

He hadn’t. Dex was used to picking fights: challenging you to see how much you’d fight for him.

That fight had been different, an entirely different game than he had meant to play. He had stepped on the field expecting baseball, but you came on with a tennis racket.

 Even now, you don’t realize how close he was to killing you—he had never told you. Dex hadn’t wanted to hurt you, but you had been forcing his hand. 

Why couldn't you see that Dex was just trying to protect you? Wasn't it obvious? As he was pressing all of his weight into keeping you pinned to the floor, he had completely engulfed your smaller form.

Dex was the dragon and you, his captive princess. All your fault it was, you were making him do this.

‘I’m so sorry, I’m sorry, I don’t want to hurt you.’  This could’ve all been avoided—you just had to quit. You didn’t need that shitty minimum wage job—you had Dex, you had your full-time job. People fought tooth and nail to land where you had stumbled. 

It didn’t matter how little academia paid, that being a professor was more something you did out of sheer love and determination. Dex would cover everything else—he was all you needed. ‘I’m sorry, sorry, so sorry.’ Repeating something don’t make it true. 

He wouldn’t forget the vibrancy of panic as he pushed your face harshly into the hardwood, grappling with you to reach your phone. It had calmed him, just a lapse that hardly lasted a second—you were never supposed to look at him like that, the deer-in-the-headlights sort of shock as if you were seeing him for the first time. In that brief pocket of time where Dex thought you might’ve hated everything you saw.  

It was just enough for you to shift away from his hold, just slightly, just enough for you to twist around and pull your foot up to kick him, first blow landing against his nose, second against his jaw. It stunned him, out of the character, you were changing the script. Dex fell slightly to the side, the intent more painful than the contact.

Then you were on him, hands on his neck, face bent down and contorted into a horrific sneer, ‘You ever, fucking touch my shit again—‘ he hadn’t been able to breathe, but fuck if that hadn’t driven the point in. Dex reached up, hands digging into your wrists but didn't attempt to pry them away--just holding, if anything, keeping them in place.

‘I’ll fucking kill you.’ you were sitting on his chest, knees digging into the sides of his torso and pressing every ounce of force you had into your grip on his neck, painful, bruising and violent. 

He had never been more aroused, your hands were so small in comparison to his neck. It added to the thrill, how much you wanted to hurt him, how far you were wiling to go for it.

‘You ever fucking touch me like that again?’ you used that force to lift his head and slam it violently back into the ground, ‘I’ll fucking kill you.’ You snarled, spit flying from your mouth as you did and Dex? Oh he had been right where he wanted to be—your actions were entirely unexpected, clashing violently against his idolized version of you, but he was delirious with pleasure, with adoration.

In that moment, when black dots were dancing in Dex’s vision and he was bordering on unconsciousness, he loved you and you, were perfect for him. There he was, every horrific, violent part of him parroted in your eyes.

Yet, you still managed to be good. Steadfast, a lighthouse to guide, a safe harbor to dock at. There was hope for him.

At least until you changed your passcode and didn’t give him the new one until a week later when he was crying so profusely his body was violently shuddering with his pathetic, desperate sobs as snot was dribbling down his chin after having cycled through the seven stages of grief before trying to challenge you to see if you would leave, then becoming terrified you might actually take him up on his offer before settling on desperately trying to tether you to him by insisting he would kill himself if you left him.

You had looked at him, really looked at him. Every pathetic, disgusting part of him and thought back to your own life. You had always told yourself that you would never be the angry man— it was a part of you, but not everything that you were. You would never be the person that made someone dread to come home. 

There had been a deviation somewhere, a fork in the road that you had taken while Dex had remained. You could recognize the familiar patterns of his violent tendencies. Sure, he had hurt you, but his neck was still covered in vibrant bruises from when you had choked him, the ones on his face had mostly faded. In comparison, you had some sparse bruising on your ribs and torso where he had held you down but you had beat his head against the hardwood with enough rage that Dex had been laying in a pool of his own blood and a concussion.

With that, you settled on giving him your new passcode with the stipulation he would get back on his fucking antipsychotics. 

Tough bargain that paid off in the end because he’s still here, with you and knows that your night hasn’t been easy, so he obediently sits and grades student papers. 

Dex listens to your movement, listens to you walk in the kitchen, fiddling with the oven and then a pan. He knows what you're doing, can close his eyes and picture you with perfect clarity from the nights he had done nothing but obsessively catalogue your actions.

After ten minutes, you are behind him, leaning over his shoulder and pressing a kiss to his temple as you hold a hot chocolate in front of him. 

When you move to pull away, Dex moves his head with your movement until you are pressing another kiss to his hairline. He reaches up, taking the hot chocolate from your hand resting in the space just above the ungraded papers.