Chapter Text
You and Dwight had been in a relationship for quite some time now, and it was very obvious that he was inexperienced in the dating field.
His main priority was to make you happy, which obviously sounds great, but part of his way of ‘making you happy’ was ignoring when something made him upset. Like, if you teased him just a bit too much, or tried to cuddle with him when he wasn’t in the mood for physical affection. This led to you having some very serious conversations with him about communication. It’s the foundation of a lasting relationship, it’s the most important thing to you, so on and so forth. He was a little embarrassed that you caught on to him trying to hide his discomfort, but he agreed that he’d start telling you when he didn’t like something you did.
He upheld his promise, and to encourage him to continue voicing how he really felt, you’d hold him close and praise him for being honest with you. You did the same thing, of course. You told him when you didn’t feel like talking and just wanted to be alone, or when a joke he made hit you just a bit too hard.
Communication was especially important when you two started getting intimate. You urged Dwight to tell you when he didn’t like how he touched you, if you were being too rough, if you were being too demanding. You were happy when he actually listened, and told you to stop doing something. Yet, as good as he got at telling you what he didn’t like, he never actually told you what he wanted.
You were very observant, always watching him for any signs of discomfort. All the time you spent focusing on him, you also picked up on when he really liked something. But he never encouraged you to keep going, keep doing that, keep touching him in that way. You had to pick up on all his physical cues just to make him feel good.
There was one thing in particular you were very curious about; if Dwight liked having his ass played with. You tested it one night, dragging a finger lightly across his hole as his cock was in your mouth. His breath hitched, you could feel his cock twitch against your tongue, and he didn’t tell you to stop. Without any encouragement, though, you were still unsure if it was something he’d be into. So you pulled your hand away.
A few nights later, you wanted to see if you could get a stronger reaction out of him. So with your index finger slicked with your own spit, you started to press carefully into his hole. You only got to the first knuckle before he started whining and pushing his ass into your hand, trying to get it in deeper. That confirmed it; it was definitely something Dwight was into. While he might’ve encouraged you to continue, he didn’t use his words to do so. You were determined to make him tell you what he wanted, so you pulled out, not giving him any further satisfaction. He never asked for you to continue, so you didn’t.
This went on for a while. You tease his hole, just barely insert a finger to get him worked up, and then remove it to continue whatever you had been doing to him before. One night, you had him sitting up to watch you gag yourself on your own fingers while your head was between his legs. After you had two fingers thoroughly drenched in saliva, he watched you as you slid one into his waiting hole, and then a second. As soon as he clenched down onto your fingers, you pulled out. He groaned, and piercing eyes stared down at you. You smirked.
“You’ve been teasing me,” he had suddenly said, tone accusatory.
“I don’t know what you could ever mean, dear,” you replied, feigning innocence. You slowly crawled up over his bare body until your face was right above his. “I can’t give you what you want unless you tell me.”
“That’s why you’ve been torturing me like this?!” He asked, eyes wide and face bright red.
“Mhm,” you confirmed, smiling. “I want to hear you say it.”
Dwight looked away from you, and bit his lip. Saying “I don’t like this” had become easier over time, but he had no practice saying “Please fuck my ass with your fingers until I can’t think.” That was way harder! How could you expect him to say something like that out loud?
“Please…” he started, slowly directing his attention back to you. “Please… I want your fingers… In my ass…” He could feel how warm his face was becoming. It practically felt like it was on fire, and your smug expression above him didn’t help one bit. He was flustered beyond belief.
“Okay, sweet thing,” you replied easily, giving him a kiss on the forehead before returning to your position between his legs. “Was that so hard?”
Dwight almost replied with something snarky, but you hadn’t given him a chance. Whatever he was going to say was cut off by a loud whine as you reinserted your two fingers into his hole. You worked them in to the second knuckle easily, his hole more than welcoming to the intrusion. It was actually extremely hot. You brushed your fingers upwards, looking around for that one special spot. Dwight had been waiting for this for so long, that once you had found it, he came instantly with a choked cry. Watching him cover his own torso in cum while you were fucking him with your fingers… You hadn’t given him a chance to recover. You mounted him then and there.
That was a few days ago. Since then, you’ve pulled some strings, called in some favors, and acquired one strapon harness, and a dildo to go with it. Nothing too big or intimidating, of course. You had picked out a small one, just in case he hadn’t done this before, or if he just preferred to be penetrated by smaller cocks. It’s not something you talked about, you had wanted to surprise him. If he said he didn’t like the idea, though, and that he preferred just your fingers, you’d back off and never bring it up again. You were content with getting him to climax with just your fingers alone, not even having to touch his dick. It was hot!
Tonight, you urge him to sit down on your bed. You almost shake with anticipation as you hold the harness and dildo in a box behind your back, gift wrapped and everything. Even got a pretty little bow on top. You can’t hold back your smile as Dwight takes his seat on the bed in front of you.
“What’s got you so excited?” He asks, smiling just as wide as you are. He’s got no clue what you have prepared for him, but just seeing you smile makes him happy enough.
You thrust the box out to him, bouncing on your heels with excitement. It’s honestly something you’ve wanted to try for a while, and seeing him take your fingers so well… You can’t wait to hear what kind of sounds he makes when you have him stuffed full of your little gift. If he likes it, that is.
He makes a little surprised face, pointing to himself in a “for me?” motion, before getting right to unwrapping his present. He takes the bow off… carefully unwraps the paper, making sure to not drop any on the floor… and opens the lid of the box. You can’t read his expression, so you quickly try to explain yourself.
“If you’re not ready to go that far yet, or don’t want to, that’s fine. I thought it’d be nice to surprise you, if this is something you’d want to do,” you say, trying to get your sentence out as fast as possible. “You can tell me if you don’t want to try it.”
“You’d do this with me? You’d really want to?” Dwight asks, looking up at you. You can see his face clearly now, and you can tell how he’s feeling. He’s just as excited as you are.
You smile at him as you nod and sit on the bed beside him. “Honey, I’ve wanted this for a while. You know I wouldn’t do anything that I wasn’t fully enthusiastic about.” To assure him just a bit more, you take his cheek in your hand and lean in to kiss him softly. He kisses back, and rests one of his hands on your thigh.
“Could we… Try it tonight?” He follows up, his voice somewhat quiet, like he’s afraid to ask. You respond by taking the box from his hands, placing it behind you on the bed, and then grabbing both of his wrists. He seems a bit confused, until you raise his hands above his head and slowly push him until his back is flat on the bed. You straddle him, and kiss his temple.
“We can try it right now,” you suggest, moving your knee between his thighs, pressing against his crotch. He’s immediately responsive to your touch.
“Okay,” he squeaks out, face completely flushed and pupils blown wide as he looks up at you.
“You know what I wanna hear, baby,” you urge, starting to trail kisses down his neck. “Do you want it?”
“Yes, yes, I want it,” he moans out, already so worked up from just your lips on his sensitive neck. Pressing your knee against his crotch once more, you can feel him starting to get nice and hard.
“Good boy. I want you to use your words while I fuck you, okay? Tell me what feels good.” You start to unbutton his shirt, trying to get him out of his clothes as fast as possible. Dwight takes it upon himself to grind down onto your knee for friction. He holds a vice grip on your hips as he humps your knee like a dog in heat, and it’s so hot that it’s distracting. You fumble shakily with his stupid buttons while also trying to focus on the wonderful sensation of his hard, desperate cock grinding against you.
Once his shirt is done away with, you unfortunately have to reposition yourself so you can get his belt and jeans off. He whines when you move your knee away from his aching dick, and you apologize by pressing soft kisses to his stomach. You get his belt off, and then his jeans, and you’re awarded with the prettiest sight you’ve ever had the pleasure of seeing.
Dwight repositioned his hands back above his head, wrists held together, ready for you to hold down for leverage to fuck into him harder. You trail your eyes down over his body, and God, you’ll never get enough of his gorgeous chest, nipples always pink and puffy and ready to be sucked until he’s crying. His stomach is so soft, a little bit of pudge that turns you on more than words can explain. A nice dark treasure trail leads down to the real prize. He’s still got his boxers on, but you can see the outline of his cock clearly through them, along with a decently sized wet spot where his tip lays. Fuck. He’s the perfect man.
You must’ve been staring a bit, because Dwight starts to squirm beneath you and whine under his breath. You finally peel his boxers off, letting his cock spring free and land against his stomach. He’s already that hard… Just from the promise of having his ass stuffed full? You can’t blame him, you guess. Just the idea of getting that harness finally secured around your hips is making you wet.
“So fucking sexy,” you coo, taking your familiar place between his legs. You’re not gonna prepare him for your strap just yet. You want to rile him up first. You drag your hands lightly across his stomach, up to his chest, and start to rub his nipples. He moans out, and it’s music to your ears as you continue your abuse on his poor buds. You know they’re very sensitive, yet he’s sensitive practically everywhere. You flick the tips of your nails across his nipples, rub along each wrinkle of his areola, and squeeze them between your fingers. While your hands are busy, you put your mouth to work as well, licking a stripe up his cock.
Dwight continues his melody of whining and moaning, and unintelligible begging and pleading for you. You can just barely make out “please” and “more”, and since he’s asking so nicely, you’re happy to give him whatever he needs. You take the head of his cock between your lips, just the head, and start sucking. Dwight thrashes above you, trying to buck into your mouth, but you raise your head up whenever he tries to get further between your lips. He whines, and it sounds absolutely pathetic, and you love it.
After a minute or two of torture, you decide to get to the main course. You release his cock from your mouth with a lewd pop, and delight in the sound it makes when it falls back against his stomach. You move a bit further up his body, just so your fingers can reach his mouth. You notice his hands are still resting above his head. God, his obedience is fucking hot. You’ll have to reward him for it.
“Suck,” you command as you press your index and middle fingers to Dwight’s mouth. He eagerly complies, opening up immediately to start licking and slobbering all over them, before tilting his head forward and taking them in his mouth to the third knuckle. He gags a bit, and you pull your hand away.
“Patience, baby boy,” you remind him, and he whines at the new pet name. “You wanna be good, right? That means you have to be careful. Don’t take them in so fast.” Dwight nods in understanding, and you bring your fingers back to his mouth. He’s much more gentle now, taking his time swirling his tongue around your fingers. It’s absolutely intoxicating to watch him work your fingers like this, and you wonder if he’d be into sucking your strap.
You entertain that thought for a moment, imagining his flustered face dripping with sweat as he tries to take your strap to the base. He’d learnt his lesson now to take it easy, so he’d go down slowly, pull back when he starts choking… Dwight sucks on your fingers mindlessly, completely unaware of the kind of thoughts you’re having.
“You’re so good at that, pretty thing,” you praise, and you bring your other hand up to run through his hair. He moans when you experimentally tug on it, and that’s when you decide that you definitely need your strap down his throat. Maybe after you stretch out his hole on your fingers. You give Dwight a quick but passionate kiss, which he eagerly reciprocates, before you move back down between his legs.
“Are you ready?” You ask. He moans out an eager yes, voice full of lust, so you start pressing a finger into his hole. There’s no resistance, so you go further in, and Dwight pants and whines above you. His sounds encourage you, and you work your finger quickly, aiming for the sweet spot that you had found the other night. You can tell when you hit it, because he arches his back off the bed and lets out a moan that’s downright whorish.
“Fuck, I love your noises,” you groan out, getting awfully worked up beneath the belt. You add a second finger, and Dwight’s eager hole takes all of it in. You work on stretching him out, getting him nice and ready to take your strap for the first time. When you feel like he’s ready, you stand up to quickly strip yourself. Once you’re fully unclothed, you reach for the box that your strap and harness were just wrapped up nicely in.
There’s also a small bottle of lube in the box, lost among the brightly colored tissue paper that the strap lies in. You had kinda forgotten about it while caught up in the intense lust you were experiencing when Dwight was sucking on your fingers. You should probably use some, just in case saliva isn’t enough. You equip the harness, adjusting it to fit you snugly, and then slot the dildo into place. Dwight has sat up slightly to watch you, mouth practically watering at the sight. Good.
“I really wanna put this inside you, baby,” you start, but you climb over his chest instead of settling between his legs. “But I wanna try something first, if that’s okay.”
He looks lost for just a moment, but quickly realizes what you’re implying. He lays his head back down and opens up his mouth, sticking out his tongue as well. God, you’re so blessed to have such an obedient boyfriend.
“You’re such a good boy, Dwight,” you coo, moving up a bit more to get into position. “I’ve noticed that you’ve kept your hands to yourself all this time. Were you waiting for permission to touch me?” You ask, a slight smirk on your face.
Dwight nods, and sticks his tongue back in his mouth only to speak. “I want to be good,” he explains, lust clearly audible in his voice. He really likes this, and fuck, so do you.
“Mmm. If you continue to be a good boy and keep your hands above your head while you suck on my strap, you can have a reward, okay?” You promise, hands trailing across his collar.
“Yes, please, okay,” he begs, and sticks his eager tongue back out. You smile, and almost press the tip of the strap to his waiting tongue, but you have one more question.
“Can I call you names?” You ask, wanting to make sure he’s okay with it before saying something that might upset him. The last thing you want to do is hurt him in any way, physically or emotionally, while trying out something that he’s clearly super into.
“What kind of names?” He asks, sounding a bit unsure.
“I wanna call you a slut,” you explain. “Or whore.” You trace patterns on his collarbones, trying to soothe him.
His eyes light up. “Oh! That’s okay. Just, um, nothing like… worthless, or stupid, please?”
“Alright,” you nod. “I wouldn’t call you those things anyway, dearest. You’re so good for me. My good little slut, yeah?”
Dwight whines, and easily melts back into the scene. You can’t see it, but his cock is painfully hard and leaking generous amounts of precum onto his torso. All these new names you’re calling him are turning him on more and more. Now that you’re sure he likes the name, you slip your strap into his mouth. Just the head at first, to get him used to it.
He sucks on it eagerly, and at first leans up to try and get more into his mouth, but remembers his lesson from earlier and rests his head back down onto the pillow. This angle is good, with him laying on his back and you above him, so you control the pace and how much of your length he can take in. You test the waters by thrusting slightly into his mouth, and he accepts it with no problem.
“Fuck, you look so pretty like this, taking my strap in your mouth. My eager little boy, you just want to make me feel good, hm?” You praise, really getting turned on by the sight beneath you.
Dwight moans in response, and nods the best that he can. You push a little bit more into his mouth, slowly, inch by inch. The dildo isn’t huge- it’s got about one inch of circumference, and five inches of length. You figured it was a good dildo to start off with, but you only had Dwight’s ass in mind when picking it out. Now, you’re glad that it seems to fit in his mouth as well.
Once you’re so horny that you physically can’t take it anymore, you pull your strap out of his mouth. As asked, Dwight kept his hands to himself the whole time.
“Such a good boy. Good boys get rewards.”
Dwight pants beneath you, trying to catch his breath after having his throat full of strap, but yet still tries to beg and plead. God, he really is desperate. It’s beyond sexy.
As you climb off of his chest, you grab the lube from the box, deciding that you definitely need it now that your spit has likely dried inside him. You just get to finger him open a second time, which, really, who’s complaining about that?
Dwight certainly isn’t, as all that falls out of his mouth when you insert a lube slicked finger back inside him is a loud moan. He was already recently stretched, so you waste no time in adding a second finger. The dildo is rather thin, so he won’t need a third to prepare him, but you imagine working your way up to that point. Maybe if he asks you nicely. Even after his hole is nice and open for you, you continue to tease him by just barely pressing your fingers against his prostate.
He huffs after a while, throat starting to go hoarse from all the broken moans you’re pulling out of him. You get the message, and decide to have mercy on him by slicking up your strap with lube and lining it up with his eager hole. At first, you have the idea to position him in doggystyle so you can watch his perfectly thick ass jiggle while you fuck it, but you’d much rather see his face during your first time penetrating him. With that thought stored in the “save for later” folder somewhere in your brain, you line yourself up with his eager hole.
“Yes, yes, oh, please!” Dwight begs, and with that, you press the first inch into him. You can’t even feel the sensation of really entering him, but his expression in that moment causes you to let out a loud moan.
“God, fuck, Dwight… I’m gonna ruin that ass,” you moan, and you grab onto handfuls of his thick cheeks to accentuate your point. You slowly guide the rest of the dildo into him, which doesn’t take very long. You’ve gotten it to the hilt for hardly a second before Dwight starts begging you to move.
“Ah, ah, baby boy. Gotta be patient if you wanna be good,” you remind him, and he stops begging, instead choosing to start whimpering beneath you. You circle your hips, barely moving it inside him, torturing him just for the fun of it.
“You can touch me,” you say, giving him permission. He immediately takes advantage of his new privilege, hands reaching up and linking behind your neck. You lean down to capture his lips in a deep kiss, which he happily moans into. You start actually moving, pulling out to the tip and then thrusting it all back in, which causes Dwight to cry out.
You release his lips only so you can hear all of his noises. He sounds like a perfect little whore beneath you, unable to stop moaning as your thrusts pick up speed. You’d love to savor this moment, but you know how fast you can make him come, and just watching him like this has already almost gotten you there yourself. You maintain your pace until Dwight begs for harder, faster, more.
“Do you only know how to beg like a slut, like a dog? Do I need to collar you like one?” It just comes out of your mouth in the heat of the moment, and you’re almost worried that you’ve ruined it, but Dwight is very responsive to your words.
“Please, yes! I need it, I need it, I need a collar! I wanna be your dog!” He cries out, and you can tell he’s getting close. You start stroking his cock as you continue talking.
“Yeah? You want a leash too? You want me to grip you by your leash, keep you in place as I fuck you on this strap?” Dwight only moans in response, his hands gripping tighter around your neck as you pound right against his prostate. “Come on, baby boy. You want me to own you?”
“Yes, yes! I’m yours!” He nearly screams as you start dragging your thumb over his leaking tip. He’s nearly there.
“Come for me, puppy,” you command, and he obeys, just like a dog. Dwight comes with a loud shout, orgasm wracking his entire body as he shakes and digs his nails into your neck. You help him ride out his orgasm, roughly thrusting into his hole and stroking his twitching cock as he shivers beneath you. When he starts pulling away, the feeling beginning to get overwhelming for him, you slowly slip out of his ass.
You take a moment to recover, laying down next to Dwight and peppering his face in kisses, showering him with praise in between each kiss. After a minute or so, you get up to retrieve a cloth to clean the both of you with. You wet it with cool water, and wipe down his chest and torso. Carefully, as softly as you can, you also clean around his crotch and sensitive hole. You discard the cloth along with the pile of your clothes on the floor, then flop back down onto bed to cuddle with Dwight.
“You know, you’d be a good puppy,” you say softly. You wonder if that’s something he’s really into, or just something he found hot in the moment.
“Y-Yeah?” He asks, looking at you with an excited little smile.
Seems like you’ve found another kink you’d like to try out with him. You hope he’s got the courage now to ask for you to indulge in it with him.