knowing me, knowing you
Fandom: Degrees of Lewdity
Pairing: Male!Gwylan x GN!AFAB!Reader
You betrayed Gwylan by not stopping Avery from going through with his ritual. But that's okay. Gwylan betrayed you too—by taking away your freedom.
Warnings: dubcon, somnophilia, hypnosis, being held prisoner, yandere-ish Gwylan, what I imagine a soft bad end could be for Gwylan basically
I was highk super insecure about this one but it received good reception by a couple of others so I decided to post it! Smut is at the very end, I'm still getting used to it so idk if it's super great but fuck it! We ball!
Spoilers for Avery's Mansion and the Brown Fox questlines!
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You had betrayed Gwylan.
You weren’t sure where everything had started to go wrong.
Ever since Landry had asked you to thwart Avery’s plans and replace the wishing bones in his vault with replicas, your life had been upended—and that was saying something, considering all of the shit you had been through previously. You had survived plenty of unsavory places, had survived everything the Temple had put you through and the people that forced you to stay with them. It wasn’t even your first heist, having robbed the people on Danube Street with Wren before.
Compared to everything you had been through up until now, replacing the wishing bones should have been a piece of cake. You had a wonderful support system—Landry and Mickey were helping when they could, and you had your (lover? paramour?) closest friend masquerading as the Brown Fox—a masked vigilante—to help you make sure everything was going according to plan.
The plan had been simple. Avery clearly held an interest in you. You were supposed to entrance him enough to gain access to his mansion. That was easy enough, he had, after two months of going on weekly dates, had you move in with him.
Access to his mansion: done.
Next, you were supposed to find where the vault holding the wishing bones was. That was also easy enough. Avery was quick to show his true colors, and one day he had dragged you to his secret dungeon to be punished. It was there that you had seen the vault.
With the location of the vault known, breaking in should have been easy. You knew Avery’s schedule. You were proficient enough with your skulduggery that eventually you would have cracked the code to the vault. Gwylan—as the Brown Fox—had even offered to help pull off a heist. Surely, the two of you together could have broken into the vault within the hour. However, you kept dragging your feet. You kept telling Landry and Gwylan that you had everything under control. Things were going as planned.
For a while, everything felt normal. Avery may have bought you from the orphanage, but you held no romantic intentions towards him. He was a means to an end. Your mission. You followed Avery’s demands perfectly, slept with him when he demanded it, attended his parties and went on his dates. You went to school, you cleaned Avery’s mansion, and you tried to spend as much time with Gwylan as you could.
Amidst the chaos, Gwylan was your rock.
Your relationship with Gwylan was… peculiar. You had only met Gwylan about a year ago. You had freshly turned eighteen, and Bailey had begun demanding weekly payments from you, when you had stumbled into Gwylan’s shop. No matter what life and the people of this town threw at you, Gwylan was always there to listen. Most importantly, he listened without judging, something even your closest friend Robin couldn’t always do. Gwylan had been quick to become your new closest friend and confidant. He understood the way the world worked, and as you two had grown closer, you had begun to help him with his weekly ritual to purge the world of corruption.
Eventually, after some bumps in the road and ups and downs in your own relationship, you and Gwylan had become a thing (as much as he could allow—it was clear he had plenty of issues he needed to work through).
Things could have been good. You could have accepted Gwylan’s help to replace the stones. Avery wouldn’t have been allowed to go through the ritual, and you’d still be your own person.
Oftentimes, you wondered what life would have looked like, had you stopped Avery. Gwylan had set out a bed for you—sure, you would have probably gone back to owing Bailey money, but you’d have a safer place to stay. It’d be better than Avery’s mansion. Besides, you had a feeling Gwylan would have your back if Bailey was stupid enough to come out to Gwylan’s shop to demand payment from you.
You would have been free from Avery’s grasp; you would have been able to freely be with Gwylan. No more being Avery’s maid, no more cooking tedious dishes (you’d kill a man if you had to make souffles or beef wellington one more time), no more stepping on eggshells in fear that you were going to get dragged to the dungeon to get whipped. You’d be free…
… Or at least, as free as Gwylan allowed you to be.
Maybe that was part of the problem. Maybe that was why you had dragged your feet in ruining Avery’s life work.
It wasn’t to defend Avery by any means. He was a terrible fucking person. But even knowing this, even though you had to monitor your own actions and words constantly around him… he gave you a sense of freedom even Gwylan didn’t. If you wanted to act out, you could. Would you get punished? Absolutely. But you still had that choice.
Even before Gwylan had put the special collar on you—something you could never take off so long it was ‘locked’ by him—you had a hard time resisting him. Part of it was just his natural charisma; but even when you first met him, you knew there was something more to it all. Magic, maybe, now that you had seen the true horrors of the world and knew magic in some form existed.
After the collar, resisting him was nigh impossible. Even if you wanted to refuse his requests, you were unable to. The option to choose had been taken away from you. A part of you hadn’t even wanted the collar, but the moment you tried to refuse, your mind had grown fuzzy, and next thing you knew the collar was on you.
You loved Gwylan. Truly. But deep down, you knew your relationship with him was just as fucked up as your relationships with everybody else in this Godforsaken town were.
Was that why you never switched out the stones, then?
Granted, you hadn’t known what would take place up in the tower. You hadn’t known that you’d be wrenched into some kind of ritual that had Avery tear a dagger into you. It didn’t physically wound you, but you could feel it scar your soul.
Something was lost in you forever that night.
Terrified, with no idea on what to do, you had immediately ran to Gwylan’s shop, ignoring the pouring rain or the blood moon high in the sky as you pounded on the door. Normally, it would have opened—but it stayed shut that night.
You had even tried the pub, knowing he would frequent there as his alias, the Brown Fox, but when you asked Landry for him, you were only met with confusion. She hadn’t known what you were even talking about.
It was as if the Brown Fox had never existed. Mickey couldn’t recall him, either. He was only left in your memory.
The shop had stayed closed for a week after the tower. With nowhere left to go, you had stayed at Avery’s, and things had carried on as normal. He had a new pep in his step, and didn’t seem to sleep as much, but other than that, things just… carried on.
It didn’t stop you from visiting Gwylan’s shop every day, though. Waiting for that door to finally open.
It shouldn’t have surprised you that when it finally did, Gwylan was upset. He had trusted you to switch out the bones, and you hadn’t. You didn’t even have a solid reason when he asked. You didn’t know why you had failed yourself, when you had the resources and skills to carry out the plan.
Was it because you were afraid of Avery? No, that wasn’t it. Was it the knowledge that you were truly helpless in the end, no matter what you did? Maybe. Avery, Gwylan—they couldn’t be more different, and yet the same in how they controlled you.
There seemed to be no way out. No matter your option, you felt trapped. You hated that you had broken down in front of Gwylan then, hated how powerless you felt.
Was that truly where things had gone wrong? Not you moving in with Avery and second-guessing yourself, not even you failing to swap out the wishing bones—but showing weakness in front of Gwylan, the one person you had trusted in this world?
It was too late—you were already deep in Gwylan’s grasp before all of this had even happened. You failing your mission seemed to only prove to Gwylan that you needed to be protected and kept from the outside world.
How many weeks had it been, now?
It was hard to keep track of time here. You didn’t have a phone, and Gwylan wasn’t too keen on letting you ever leave the shop anymore unless it was for breakfast or a ritual—both activities that kept you by his side.
Your collar was locked again—it had become unlocked during Avery’s ascension ritual, although Gwylan had been more than happy to lock it again.
It was funny. Once, a long time ago, Gwylan had asked you if you’d willingly leave Avery behind. You had agreed wholeheartedly at the time, before admitting it was still better than the orphanage. He had reminded you it was still a birdcage.
Wasn’t that what this was, too? Wasn’t his shop its own form of a birdcage?
“Pet! I’m back!”
You were brought out of your own introspection by his cheery voice. He seemed to materialize out of nowhere, although his bright grin died down a bit when he saw you were just sitting by a window. It was locked shut—escape was not an option. It never was.
“Do you want a walk?”
“I’m fine.” Your response was short, clipped. Going outside while leashed to Gwylan would hurt more than it did by being stuck in this shop. An illusion of freedom; a glimpse of what you could have, just out of reach.
He reached out and pet your head, an action that would have once soothed you. More often than not nowadays, it just soured your mood.
“I’m sorry I can’t give you what you want.” His voice was softer, this time. Understanding. As if he understood what exactly you were going through. He never would. Not truly. You didn’t even look at him, not until his hand moved from your head to your chin, turning your gaze towards him.
His eyes seemed to glow in the dim lighting of the shop. “I’m doing this to protect you, dear.” His voice was nearly pleading, begging you to understand him. Just as he didn’t understand what you were going through, you couldn’t bring yourself to understand his own actions in keeping you here.
“. . .” You didn’t know how to respond, knowing if you just pleaded with him or said the wrong thing, he’d take your voice away. He’d done it before. You knew he had no qualms about doing it again.
At your silence, he continued. “I trusted you to change out the wishing bones, and instead you got yourself hurt in the process. It’s not something I can ever reverse.” His thumb pressed against your lower lip gently, his gaze not once wavering from your own. It was as if he was staring into your very soul, able to see each and every thought and worry that flitted through your mind. “I can prevent anything worse from happening to you, though.”
He let go of your chin, only to pull you into a tight hug. He buried his face into your neck, and you hated how your arms instinctively came up to hug him back. It was second nature to you, and you didn’t even think it was the collar to blame. This was all you.
“I don’t want to see you hurt. I don’t want to lose you. Not you.” His voice was muffled slightly, his lips brushing against your neck as he spoke, but you still heard him perfectly well. “So just… continue to stay with me. Alright? I’ll keep you safe here. Stay with me.”
Warmth ran through you at those last three words. Your eyelids began to droop. It was as if your anxieties and concerns were ebbing away. You knew it was Gwylan’s doing, but you couldn’t find it in yourself to care that you were falling under his compulsion again.
You had betrayed him by not stopping Avery. It was a decision that would forever haunt you. Gwylan had lost his trust in you.
But just as you had betrayed him—he had betrayed you by taking away what was left of your freedom.
The orphanage, Avery’s mansion, here… They were all cages you had been trapped in.
Only this one, you’d never escape.
You slept alone most nights, now. Gwylan used to come crawling into your pet bed, but he hadn’t done that as of late. Not since the tower incident.
It was late—you had curled up into your pet bed, expecting another night by yourself. You weren’t sure when you had drifted off to sleep. Sleep came uneasily most nights, but recently he had used hypnosis on you to help the nightmares you had been having. You didn’t usually remember them, but that hadn’t stopped you from waking him up screaming for the past couple weeks.
Your sleep was dreamless, at first. You barely roused yourself as you felt your bed dip. Arms wrapped around you.
“Shh, pet… Go back to sleep.”
And so you did, not even thinking anything of it.
Your sleep was dreamless. You floated in a dark sea on a bed of clouds, oblivious to the world around you. But something was wrong.
Something was inside you.
You jolted, a low whine leaving you as you were more insistently roused from your sleep. In your bleariness, it took you a minute to piece together what was really happening. Your pajama bottoms had been tugged down, an arm wrapped underneath and around your waist and two fingers crooked deep inside you. Your breath hitched as they curled slowly, dragging against your walls. You were shushed once more as a whimper left your throat. For a moment, you were reminded of past assaults; times you had been touched against your own will. You instinctively reached down to try and pull the hand away—but your body went limp, your limbs suddenly not your own to move. His free hand came up to your throat, trailing a finger up the center of it.
“Let me take care of you.”
You were only soothed by the realization it was Gwylan’s voice. It was just Gwylan—certainly not some stranger assaulting you in your sleep.
Somehow, the knowledge it was Gwylan didn’t bring you as much peace as you would have hoped it would.
His pace was unhurried as he fingered you, your juices coating his fingers and making quiet squelching noises with each thrust into your tingling pussy he gave. He rutted shallowly against you from behind, and you opened your mouth only for no noise to come out besides another small whimper.
“Shhh.” You were shushed once more, not that it mattered—Gwylan had taken your voice.
It was hard to ignore the arousal that was building in you. Gwylan knew your body well by now, knew what exactly to do to make you orgasm. He began to work a third finger into you, another stifled whine leaving you. You had the urge to squirm, but not the leeway to move your body to do so.
The hand that had been around your throat dropped down to your chest, squeezing one of your breasts gently, his nails just barely digging into you through the fabric of your pajama top.
He crooked his fingers again; his nails lightly scratched you in a way that was more pleasure than pain. Then, he twisted his wrist, the movement having you arch into him, finally able to move your body somewhat as his thumb pressed down firmly onto your clit. The combination of him fingering you and toying with your clit and rhythmically squeezing your breast sent you careening over the edge, your first orgasm rocking through you.
Your thighs trembled as he fingered you through your high, stopping just as it began to feel too oversensitive. Your entire body tingled, his fingers making another squelching sound as he withdrew them from your pussy. You heard him suck on them, cleaning your juices off before he pulled back slightly.
The distance was short-lived. He rolled you onto your stomach, his hand gently pressing your face into the pillows beneath you. You could hear him adjusting his clothing with his free hand, and then his cock was sliding between your thighs. Not yet angled to thrust in; he was still taking his time with you.
“Just be a good pet and lie still for me… okay?” He was panting above you, and he thrust between your thighs a couple of times, catching your wetness onto the head of his cock before he re-angled himself.
No matter how many times you two had had sex, the initial stretch always seemed to hurt. Gwylan was just blessed with good genetics on how thick his cock was. Even with preparation, there was a slight burn from how he stretched your walls out. Normally, he would have started with shallow thrusts—this time, he thrust his entire cock into you in one go, bottoming out and eliciting another whine from you.
He stayed like that. Just for a moment. He panted above you, leaning over you as he rutted shallowly into you for a moment. His grip on your head loosened a bit, only for him to pet your head in an almost-condescending manner.
“Good pet… You’re always so good for me.”
You hated how his praises sent a new wave of arousal flooding to your core.
With your voice still gone, and your body sluggish, it took all you had to keep you from completely falling into the bedding as Gwylan began to thrust into you. He was no longer taking his time, and your arms shook as you tried to prop yourself up a bit so you didn’t get a faceful of pillow. His thrusts were hurried, and you could hear him pant heavily above you as he kept you down.
“You’re gonna cum for me again.”
It was a demand—one you couldn’t resist. As he reached around with one hand to play with your clit once more—his other hand still at the back of your head—you could feel the dams burst. You clamped down around his cock as you came, another whine leaving you. It was all you could manage without your voice.
You were becoming over-sensitive—not that Gwylan cared. He continued to fuck you, and you could feel his cock twitch inside of you, telling you that he was near release himself.
“One more time. You can do that for me again, can’t you?”
You didn’t want to. You didn’t think you had it in you to cum a third time in such a short time frame, but since when did he care what you wanted anymore? In your peripheral vision, you could have sworn you saw glowing green lights, dancing just out of your vision. The lights soothed you, worming their way into your brain and causing your entire body to jolt.
Your third orgasm was intense, your mouth dropping open but with no sound to release. You jerked down, and Gwylan followed you, his hand moving from your clit to your hip to keep you in place. His nails dug into your skin as you felt him cum deep inside you. He pushed deeper, your hole stretching slightly around him as he pushed his knot inside of you. His cum continued to spurt out, igniting a new warmth inside of you.
Your mind blanked out, just for a moment. White hot pleasure coursed through you at both your orgasm and the fact you had followed his command. When you began to become aware of your surroundings once more, your throat felt looser. You didn’t need to speak to know your voice was given back to you.
Gwylan thrust into you a couple more times, soft pants leaving him as he waited for his knot to deflate. Your pussy tingled, each small thrust sending a sharp jolt through you as pleasure turned into prickling pain from the over-stimulation. Soon enough, his knot was deflated enough for him to pull free of you, although little fluids leaked out of you.
Arms buckling beneath you, you collapsed back into the bed with a quiet huff. Gwylan giggled, crawling in after you and holding you close.
“Good pet,” he murmured, petting your head once more. It had been a long time since the two of you had been intimate with each other. No doubt he had been pent up. Despite your misgivings and unhappiness with your treatment, you had been a bit pent up, too.
“I’ll keep you safe,” he promised, tilting your head back so he could peck your lips. “Just go to sleep. I’ll be here.”
Despite it not being a genuine command, your lids felt heavy all the same. You were frustrated with Gwylan. What he was doing to you—it wasn’t right. All the same… There was nowhere you felt safer than here, and right now, perhaps that was really all you could ask for.
Leaning into his touch, you let out a deep sigh, before slowly falling asleep in his arms.
You could worry about everything else in the morning.















