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Published:
2022-07-20
Updated:
2025-09-19
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20/?
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A Series of (Potentially Unfortunate) Kinks

Chapter 20: H(edging) a Bet

Summary:

The random prompt was "edging"

Notes:

Unsure if it's too early to say "I'm back, baby"... But this is a lot from me all at once. Apparently the generic of one of my medications is the devil, and for the low, low price of $400 a month, I can write porn to post on the internet again...🙃

Also, I promise I am working on other (less smutty, more plot-y) things, but there's a lot of unfinished business in my google docs that I'm attempting to complete. Basically, there's a lot of half-written smut in my docs, because a prompt would give me a sudden burst of motivation, but then my brain would just fog-out half-way through🫠

(See the end of the chapter for more notes.)

Chapter Text

When Matt had threatened to edge her repeatedly, and to the point that she could no longer take it, she truly hadn’t believed him. Alex had believed that he would cave and fuck her before long, but he hadn’t. He had made good on his threat, leaving her writhing and begging and desperate not to be the first to give in...

Some time earlier

“I guarantee I could make you break before I ever would,” Matt wagers, a grin on his entirely too smug-looking face.

Alex just rolls her eyes back at him. “There’s not a chance you wouldn’t have your cock in me long before I’d ever give up. You may have good stamina, darling, but you are still a man.”

“Is that a bet, Kingston?” He asks, brow raised, and his eyes grow dark.

“It’s a promise,” she replies, feeling a little smug herself, because, after all, she is the far more experienced of the pair.

And that is how Alex finds herself naked with silk ties around her wrists. Her confident nature had allowed her to agree to such terms, but not without making some of her own. Matt isn’t allowed to touch himself either. He is free to do with her as he pleases, but he is to keep his hands off his cock.

“You tell me when you think you’re about to come, because any orgasms will be considered game over,” Matt tells her with intention. “Deal?”

“Deal?” Alex nods in agreement.

Matt starts slowly and gently, his fingers teasing her nipples into stiffened peaks before he takes them into his mouth and sucks until they turn from dusky pink to red. He introduces teeth to them as his right hand introduces itself to the opening between her legs that is growing more damp with each passing moment. 

His fingers glide through her folds, and Alex whimpers as he dips one fingertip just lightly inside of her, teasing her and causing her to lift her hips to try and get more of the digit to press inside. He pulls back, however, leaving her squirming and looking for his hand, but she finds it merely on her hip next, holding her down as his mouth switches to her other nipple. The other feels cool as the air hits the sensitive, saliva-slickened bud, and she moans as teeth bite down carefully on its sister before scraping along until it falls from Matt’s mouth.

“Remember, you tell me when you think you’re about to come,” he reminds her as he scoots back to kneel between her legs, and Alex simply nods in recognition, a little afraid what sort of begging might slip out if she opens her mouth.

Her mouth, however, ends up opening of its own volition as the pad of Matt’s thumb suddenly presses down onto her clit, and she lets out a long moan as her hips give an involuntary buck.

“Like that?” He asks, his thumb making circles over the sensitive bundle of nerves, and once again, all Alex can manage is a nod.

“Already so wet for me,” Matt voices his observation, his tone pleased.

“And you’re already completely hard for me,” Alex counters, but the breathiness in her own voice betrays just how far gone she already is.

She can already feel herself growing closer to her first edge, and she wants nothing more than to internally say ‘fuck it’ to herself whilst verbally saying nothing at all to Matt, already eager for an orgasm. She can’t and won’t give in that easily though. She isn’t a horny teenager. She can control herself. What she can’t control, however, is the way that her thighs begin to tense and shake, and she knows she can’t hold on for much longer.

“Oh god,” she breathes out.

“Close?” Matt asks.

“Yes.”

“How close?”

“Very,” she confesses, her voice strained from her efforts to hang on.

It isn’t but a few seconds later before she is jerking away and crying out, “stop! Oh fuck. Stop! I- I-”

Alex breathes out a conflicted sigh of relief as Matt’s hand pulls away. She has to fight her body’s instinctual urge to follow the path of the hand as it craves the miniscule amount of stimulation it needs to cause an orgasm. She has to force her legs to stay parted, and her heart is beating wildly, making her feel out of breath from such little physical exertion. 

“That’s a good girl,” he praises her softly, his hand coming up to stroke her cheek with the backs of his fingers. “That was perfect.”

He kisses her as he allows her to cool down from her first edge, merely tending to the embers between her legs without fully causing them to spark back into flames, and soon her breathing is somewhat normal again.

This time, Matt presses two of his fingers inside of her, and her inner muscles contract around the welcome intruders as she lets out a moan of contentment that is cut short by a gasp as his thumb returns to her clit. It is torture to feel his unmoving fingers inside of herself, but his thumb strokes those delightful little circles against her clit once more, and she feels herself climbing higher and higher until her thighs start shaking again.

Finally, a practised curling of Matt’s fingers has Alex yelping out an urgent, “stop!”

Matt hushes her whimpering with his wet fingers, bringing them to her lips. 

“Open,” he tells her, and then, “suck.”

Alex obediently opens her mouth and closes her lips around the slick digits as Matt moves them forward, happily tasting herself on his skin.

“That’s it,” he encourages her, the fingers of his unoccupied hand casually combing lightly through her curls.

He kisses her lips as soon he slips his fingers back out from between them, and he swallows her loud moan of pleasure as those same fingers plunge back inside of her wet opening. This time, however, they are anything but unmoving. They curl and thrust, and they drive her mad. It takes no time at all before she begins moving her hips, fucking herself onto Matt’s hand, desperate for more, and he gives it to her, pressing the heel of his palm against her. Alex cries out as her swollen clit is rubbed against it in turn, and she knows a third edge is just over the horizon. 

Her thoughts and movements are frantic, her mind begging her to stop and her body begging her to keep going. She needs to come so badly, but her staunch desire to win takes over in the end, suddenly attempting to scramble away from Matt’s hand.

She lets out a desperate cry of, “stop! Stop!”

Her heart is racing, and her breathing is laboured, the taste of a powerful orgasm practically on her tongue. This edge had hit her particularly hard and rather painfully, and her body is still shaking from it, feeling like one wrong move might push her over.

“You’re alright, sweetheart,” he murmurs, and though she knows it is alright, it doesn’t bloody well feel alright. “That was only three. You’ll have to manage quite a few more, because I’m nowhere near giving up.”

Alex groans, but ultimately knows she has the determination and willpower to take it for much longer.

When she stops shaking, Matt takes this to mean she can handle being touched again, and he enters her with three fingers this time, giving her just the slightest bit of a stretch that feels wonderful and delicious. His fingers feel incredible inside of her, and she moans as her cunt clenches around them without thought.

“You like that, hmm?” Matt hums. “You like my fingers inside you, filling you, stretching you? You like when I fuck you with my fingers, don’t you?”

“Yeeess,” Alex hisses out as fingertips curl and press against that perfect spot on her upper wall.

“I bet you’d love to come on my fingers right now, wouldn’t you?”

“Oh god, yes,” she groans, and at this rate, Matt will talk her right to the edge.

“Surrender, sweetheart, and you can come right now,” he tempts her, but Alex shakes her head firmly.

“It’s going to take more than that, darling,” she declares, her words sounding as unsteady as she feels.

Matt apparently takes her words as a challenge, beginning to thrust his fingers in and out of her cunt, making certain to caress her g-spot each time. His thrusts are hard and fast, and he uses the thumb of his other hand to stroke her clit. 

“Stop!” Alex sobs out. “Stop! Stop! Please stop!”

Her cunt is screaming when Matt does as she orders, and she lets out an agonised moan of disappointment and frustration. Her body trembles all over, and her hips lift up from the bed in desperation. She feels on the verge of tears already, but she can do this. She knows she can do this.

“You’re so fucking sexy like this, love,” Matt says with a groan, watching Alex writhe about helplessly before him, and she lets out a tiny whimper at his words.

Her body seems to refuse to calm down, still feeling like any small caress of her clit might send her into orgasm, and she forces her knees as far away from one another as she can get them. 

“No! Not yet!” Alex gasps as Matt’s hand moves to touch her between her legs.

“I think you’ll find that you’re at my mercy, and I’ll touch you when I please - unless you’ve got a particular word you’d like to say,” he tells her smugly, his hand continuing onward, and his thumb easily parts her swollen, slick folds, dipping just inside the opening they hide. “It’s your responsibility to not come and to tell me when you think you might. There’s no set time between edges. If one touch takes you right back to the edge, then you say so and I’ll stop. Understood?”

Alex nods, and as soon as she does, Matt’s wettened thumb moves up to her clit and strokes it gently. 

“Matt!” She gasps out, her hips jerking upward of their own volition, pressing the pad of Matt’s thumb more firmly against her most sensitive point.

It only takes a few more gentle strokes before she is begging Matt to stop, her hips jerking away this time instead. 

“It’s getting harder to hold off, isn’t it, love?” 

He smirks down at her as he asks, and Alex can’t possibly tell him just how desperate she is growing.

“I’m doing just fine, darling,” she lies, trying to sound as confident as possible, but Matt’s short sound of laughter tells her that she hadn’t been very convincing.

“Six edges - is that all you can handle?” He inquires amusedly.

“Not even close,” she bites back before she does her absolute best to steady and focus herself, willing away the nearness of her release.

She’s done surprisingly well, she thinks, pleased to not shoot straight into an orgasm as Matt’s hand dips between her legs once more, three fingers swiftly entering her and causing her to let out a loud moan of pleasure that grows even louder when the heel of Matt’s hand presses against her clit once more, stimulating her so fully.

Alex can not only feel but hear just how very, very wet she is, a seventh edge growing closer by the second, but it just feels so bloody good to be fucked by Matt’s hand. His long fingers are so wonderful and talented, and she thinks she could spend forever letting him do this to her. The only thing better is having his cock, but she isn’t going to get that any time soon more than likely.

Her edge sneaks up on her. She is fine one moment, but the next her eyes are flying open wide, her body is jolting away from Matt’s hand, and a shout of “stop!” leaves her lips as she hits the hardest edge she has ever experienced in her life.

Alex thinks she might actually cry at this moment, her every nerve screaming out in agony. She needs to come! She needs to come more badly than ever before, but she is left to continue denying herself the pleasure of release… unless she wants to give in and concede, but nothing can make her do that so easily.

“You’re alright, love,” Matt tells her soothingly, and Alex shivers as he rubs her thigh in an act of tenderness, even the most innocuous of touches threatening to set her off. “You’re alright… That’s it - just breathe. It’ll pass.”

She is incredibly grateful for his gracious nature as he allows her to rest and fully come down this time, continuing to murmur sweet words of encouragement as she does so.

Little had she known that Matt’s kindness would have an ulterior motive…

Alex frowns as Matt steps away to retrieve something, and she can’t help but allow her jaw to drop open in shock as she sees their vibrating wand in his hand, because surely he doesn’t mean to use that on her… right?

He does though, plugging the cord into the wall beside the bed.

“Matt, darling, there’s no possible way I’ll be able to take that thing and not come,” she protests indignantly.

“Well, that’s your problem now, isn’t it?” He smirks, turning the wand on to somewhere right in the middle of its range of speed. “Remember, sweetheart - don’t come.”

Alex’s expression of dumbfounded betrayal morphs instantly into one of pleasure as Matt presses the wand to her clit, the swollen bundle of nerves hypersensitive now, and it feels so good but is simultaneously almost too much. Her hips jerk and jolt and buck, uncertain whether they should move towards the toy or away from it. The only sounds in the room are that of vibrations and her continuous moaning.

Matt edges her repeatedly this way, the time between edges growing shorter and shorter, and Alex lets out a helpless sob as she hits a twelfth edge.

“Stop! Please stop!” She sobs out, her body quivering on the precipice of release, and Matt almost doesn’t move the wand away fast enough, leaving her system in shock of such an abrupt cessation of pleasure when it had been a millisecond away from what it needs most.

The quivering is practically a permanent side effect for now, never dwindling or relenting between edges, and Alex finds herself coming to the realisation, after number fifteen, that Matt is going to win this one. As long as he isn’t being stimulated, he can’t lose no matter how affected by the sight of her like this that he is. The game had been one-hundred percent rigged from the beginning, and logically, she had known that but still stupidly believed she could win. Her resolve is quickly leaving her, and she doesn’t know how she should proceed, her mind clouded in a hazy fog of pleasure and frustration.

It turns out that she doesn’t end up having to make a decision as Matt presses the wand to her once more, but he increases the speed of the vibrations, leaving her utterly speechless and unable to breathe or think at all. She feels the precise moment she gives up her fight, coming to the recognition that she is simply going to allow herself to come this time.

It feels incredible as she flies over the edge into what feels like the most powerful orgasm of her life. The repeated edging and prolonged state of arousal really pays off as she lets out a hoarse scream of pleasure, feeling it overwhelm her and grow as Matt increases the vibrations once more. Her first wave of orgasm barely relents before she feels a second wash over her, pulling her out to sea and trapping her in the harsh current that she isn’t sure she ever wants to escape from. She’ll go through this torture again and again if it means pleasure like this.

Finally, Alex slumps limply to the bed, the heavy rise and fall of her chest being the only sign of life from her as her mouth falls silent. Matt is quick to untie her after he sets the wand aside on the night table, pressing a gentle kiss to each of her wrists before then pressing one to her lips. 

“Well, you lasted longer than I expected,” Matt murmurs to her as he crawls onto the bed beside her, his straining erection pressing against her hip as he puts his arms around her and pulls her close.

“Excuse me?” 

“Around edge number ten, I really thought you were going to give up,” he answers. “Definitely lasted longer than I would have if our positions had been reversed.”

“That looked like a fairly spectacular orgasm,” he adds.

“Oh, it was,” she says affirmatively and with full conviction.

“Perhaps we should try it the other way ‘round - me tied up and you driving me mad.”

“Perhaps we should,” Alex concurs with a soft, tired smile. “Now, are you going to fuck me or not?”

“But you just-” Matt stammers out, not necessarily expecting her to want more, noting how exhausted she appears.

“Fuck me, darling,” she orders him, looking at him over her shoulder as she bends one knee and raises it, giving him ample access to do so.

His cock is beyond hard, and it aches horribly. There’s nothing he wants more than to fuck her, and who is he to deny such a cordial invitation? 

Matt presses the swollen head of his cock to Alex’s welcoming, wet opening, and he presses just the tip inside, loving that familiar first stretch of her body accommodating him. She is so snug and hot around him, and he finds himself unable to hold off for any longer, pushing forwards and sheathing his entire length inside of her with one smooth thrust.

They moan out in a chorus, each relishing of the feeling of being joined, and Alex quickly pleads with Matt for him to move and to fuck her. He curses under his breath against Alex’s ear, loving the sound of her eagerness, and he can’t help but to give her what they both want, his hips pulling back before they snap forward. 

His cock slams back into her, and Alex lets out a howl of pleasure. Her cunt is so sensitive and still swollen from their previous activities, and she feels everything so acutely. It isn’t a bad thing, though, quite the contrary actually. She loves the heightened sensation of Matt’s cock hitting her swollen g-spot each time he enters her. It feels wonderful, and her inner walls unconsciously contract and flutter, clenching and gripping at him, only intensifying the sensations for both of them.

Matt knows he can’t last, and somewhere in his haze, he has mind enough to reach behind him and retrieve the wand from the night table. Alex gasps when she hears the sound of the toy coming to life, and she ululates loudly in gratification when the vibrating head of the wand is firmly pressed to the ultra-sensitive nerve bundle between her shaking legs.

Alex cries out, her head arching back, and the scent of the product in her hair fills Matt’s nostrils as he finds his nose buried in her curls. Her hips jolt, unsure whether to jerk away from the intense, nearly painful stimulation, or to push towards it in search of the likely possibility of further pleasure. But Matt’s cock feels so good inside of her, filling her and offering the most delightfully familiar stretching of her inner walls as her body moulds perfectly around him.

Matt groans into her ear as the tormenting of Alex’s clit causes her body to squeeze his hard length so wonderfully and so unyieldingly tight that the rhythmic motion of his hips stutters against his will. It brings several expletives from his mouth, a tinge of desperation melded into each one as his breathing turns to panting.

“Alex, love, I- I can’t-” He pushes the words out with difficulty, his movement faltering further as he deeply inhales before letting out a long, steady exhale as he attempts to wrangle his body in, but his balls are tight and he doesn’t know how much longer he can hold off.

“It’s okay, darling,” she assures him, her own voice breathy, and a high pitched, nearly strangulated sounding little moan forces its way out of her throat when Matt’s thumb finds the button on the wand that increases the vibration.

He presses it twice, and Alex can feel the sudden impending orgasm entering her line of sight. She can practically taste it on her tongue as her body begins its tell-tale quivering.

The speed of Matt’s thrusts increase, and she knows he is at the precipice of his own release, so she brings a hand up to her own breast, fingers finding the nipple, and she pinches. She moans as she twists the sensitive little bud, and the display sends Matt over the edge with a grunt of her name in her own ear.

It becomes a domino effect; the sensation of him spilling into her as he comes sets off her own orgasm, her body writhing helplessly against Matt and against the incessant barrage of vibrations against her clitoris. It’s too much, bordering on painful even, but she hardly registers the tenderness through the overwhelming pleasure her body seeks like a drug.

Neither of them manage a word as they come down, both beyond spend and exhausted, particularly given the lateness of the hour. Matt only manages to turn the wand off and push it just out of the way on the bed, his cock still resting inside of Alex, having yet to soften, and they fall asleep sated, connected as one, and neither of them being a loser in the outcome of their bet.

Notes:

Thank you so much for taking the time to read! All comments and/or kudos are always greatly appreciated, especially while I'm attempting to find my footing with writing again!💕💕

Notes:

Okay, so nothing too out of the ordinary for me, but there’s nothing wrong with an ‘easy’ start. I guess the ‘easy’ bit depends on how good it came out…

Please let me know what you thought, and thank you for reading! 💕💕