𝙎𝙬𝙚𝙚𝙩 𝙏𝙝𝙞𝙣𝙜
Jolly x virgin!Reader
Tags: first time, loss of virginity, breeding kink, praise, soft dom jolly, smut, P in V, fingering, age gap, cuddling, bathing, very sweet and wholesome, jolly being an absolute gentleman and consent king
9.2k words of pure filth
At some point, while drunk, you had texted him, asking him if he’d be willing to take your virginity. The next morning when you woke up, you wanted to cease to exist. Yet you couldn’t stop thinking about him, imagining him—his strong body holding you close, rough voice whispering filth into your ear as he ruined you. Pressing your face into the mattress, ruining your tight pussy, a calloused, tattooed hand wrapped around your neck. Or Jolly takes your virginity and it's all soft and sweet
Also available on AO3
A/N: I saw bad omens live and was standing really close to Jolly. It led to all of these thoughts. Seeing that man in real life altered my brain chemistry (sorry Noah). This is definitely the filthiest thing that I’ve written so far, I was literally writing this and kicking my feet in the air, giggling at how explicit it is. Can't believe that my longest fic for this fandom is just 9k words of pure filth. Hope you all enjoy it just as much as I did.
After months of texting, talking, sexting, the moment finally arrives. You stand outside Jolly’s front door, collecting yourself. No doubt he noticed your car pull into the driveway, but you don’t care. You need this moment of calm, a moment to collect yourself. You can’t actually believe that this is happening.
The two of you had first met months ago at some label party. Your uncle worked there, and so you had wriggled your way into getting an invite. Music was always something that you were into, and you dreamed of turning it into a career—but for years you struggled to get your foot in the door.
Still, you attended the party. Not just in hopes of being able to network your way into something (despite being much younger than everyone else there), but also to get a glimpse into the music industry. You don’t even know how it happened, but at some point you had ended up talking to Jolly. You were being almost too friendly, but he seemed to appreciate your enthusiasm. He didn’t mind spending the rest of the night simply chatting to you at the bar, answering whatever questions you had. Even though you eventually parted ways that night, you still managed to receive his phone number. He gave you a smile, telling you that he hoped to hear from you soon.
From then on, the two of you began texting regularly. Currently, you could confidently say that you trust him as much as your closest friends, maybe even more. He’s become an important person in your life, someone who you text daily, updating him on little things that are happening in your life. With the age difference between you two, you also see him as somewhat of a trusted fatherly figure. Almost. When it comes to making difficult decisions in life, or when you’re faced with an adult problem, Jolly is the one that you turn to for advice.
Over time, your relationship grew, and turned into something sexual fairly fast. Honest conversations at night turned into calls filled with gasps and moans of pleasure.
At some point, while drunk, you had texted him, asking him if he’d be willing to take your virginity.
The next morning when you woke up, you wanted to cease to exist. You couldn’t believe your audacity, the sheer gall to ask something like that from a man who was nothing more than a glorified friend-with-online-benefits. You hadn’t even seen him in person, apart from the first time that you had met. What made you think that he would want to meet up with you in order to get some sub-par sex from someone who didn’t know what they were doing?
Yet you couldn’t stop thinking about him, imagining him—his strong body holding you close, rough voice whispering filth into your ear as he ruined you. Pressing your face into the mattress, ruining your tight pussy, a calloused, tattooed hand wrapped around your neck. You had soaked your underwear so many times, humping your pillow and imagining it to be his strong, muscular, thigh.
You didn’t tell him about any of that, though.
You were mortified when you saw that he had read your message. You were even more horrified when he responded a few hours later.
I’d love to, sweet thing. It would be an honour. Let’s call later and talk it through, yeah?
You wanted to scream.
Still though, he held true to his word, calling you in the late hours of the evening.
You saw a new side of him. He had run to reassure you, telling you that it was okay, that what you had asked wasn’t completely out of the blue and wholly inappropriate.
“Honestly, I was almost waiting for you to ask me,” he chuckled, causing your face to turn red. Were you really that shameless and easy to read? You didn’t like how obvious it was that you wanted him to bend you over a table and have his way with you.
After some more talking and going over expectations, the two of you had settled on a time and place.
“God I can’t wait to ruin that sweet pussy of yours,” he groaned, sending a rush of heat straight between your legs.
Time couldn’t have moved any slower.
- - - - -
Nothing could have prepared you for seeing him with your own two eyes.
A black buttoned-up shirt tucked into his soft, black slacks. He’s taller than you remember—making him seem like he’s absolutely towering over you. Most of his hair flows down his back, while the rest of it is tied up into a tiny bun that rests atop his head. His facial hair is neatly trimmed, making you wonder how it would feel brushing against your bare thighs. A singular silver cross dangles from his ear, while the gold hoop in his nostril catches your attention, glinting as the sunlight lands on it.
He looks like the embodiment of sex itself. You don’t know if you want to lick him, or run away and cower in a corner.
His eyes light up as his stare lands on you. He smiles.
“It’s so good to finally see you.”
He pulls you in, crushing you in a hug against him. You get a small taste of how warm and firm his body is, and it immediately makes you feel a craving deep inside of you. So much for not getting excited too fast. He doesn’t let go of the hug until you do. Once you do, though, he pulls away and holds you by the shoulders, smiling down at you, clear reverence in his eyes.
“Let’s head inside.”
Jolly lets go of you, instead gently weaving his fingers with yours, taking you by the hand once you’re done taking your shoes off. He leads you into the house and over to the living room, and guides you to sit down on the couch.
“Would you like anything to drink?”
You look down at your shaking hands.
“Just a glass of water, please.”
Anything to occupy your hands and stop them from fidgeting.
As Jolly leaves the room, it gives you a chance to look around and admire his home decor choices. You can’t deny that from what you’ve seen so far, his house looks incredibly comforting. The walls are a soft, muted gray. Long, flowing curtains meet the ground, shielding the windows from the outside. A plush rug meets your toes, so unbelievably soft that you can’t stop yourself from running your feet along it multiple times. There’s various paintings on the walls, all depicting calm nature scenes. The couch is plush and sinks under your weight, decorated with various blankets and pillows. The shelves nearly buckle under the weight of books and various artefacts. Under the TV, there’s a beautiful brick fireplace, and it’s not difficult to imagine how it fills the room with warmth once it’s ignited.
“You’ve got a really nice house,” you say once Jolly returns. You mean it.
“Thank you,” he responds, handing you the glass of water.
If he notices your shaky hand as you reach out to grasp it, he doesn’t mention it. You take slow sips, the coolness of the water settling over your throat. It helps to calm you, if only a little bit. Jolly sits down beside you, bringing his legs up onto the couch and crossing them.
“Nervous?”
So much for not being obvious.
“A little bit.”
“That’s okay. It’s completely understandable.Thank you for being honest.”
He’s so smooth, so in control, that it makes you want to give into anything that he says.
“There are some things that I’d like to talk about, but first I want to set up some ground rules.”
“Okay.”
“Firstly. I want honesty. No lies, no bullshit. If something hurts or feels off, you tell me. If something feels even the slightest bit wrong or out of place, you tell me. If you want to stop, you tell me. If you want to do something, you tell me. I can’t read your mind or know what it is that you want. We can’t do this without honest communication. Understood?”
You nod, almost feeling lightheaded from his tone of voice. He’s not loud, demanding, or angry. He’s more so firm, solid, unwavering in his rules—yet still so utterly delicious.
“Words.”
“Yes,” you croak, your throat drying up. “I understand.”
You take another sip of water.
“Good. Every time I ask you a question, I expect an answer. A verbal one. Understood?”
“Yes.”
The word ‘sir,’ nearly leaves your lips, unspoken yet desired.
“Lastly, and most importantly, if you want to stop, you tell me. No bullshit, no lies, no fooling yourself that you should hold out. I’m here to help you enjoy yourself, not test you. Can I trust you that you’ll be honest with me, and tell me to stop if needed?”
You swallow. “Yes.”
“Do you have any issues with any of those things? Anything you’d like me to clarify?” His tone softens and his head tilts slightly, eyes understanding.
“No, it all sounds good.”
“That’s good. There’s some more things that I’d like to discuss with you, but I’d like to do that once we go upstairs, if that’s okay.”
“That’s fine with me.”
“Great,” Jolly stands up, his hand reaching out for yours. “C’mon.”
You place down your glass of water and instinctively grasp his hand in yours, his grip firm and unwavering. His hand is so warm, his calloused fingers radiating a soothing heat. His thumb subconsciously strokes against your hand, proving a soothing motion that you didn’t even realise you needed. Jolly leads you through the house, his hand constantly holding yours. He guides you into his bedroom, closing the door behind him. You step inside, and immediately notice the plush carpet that meets your feet.
Jolly lays down on the bed, sitting up a little, propped up against the headboard, as he pats the space beside him.
“Make yourself comfortable. Do what feels right. We’re not doing anything sexual just now, only talking.”
You hesitantly slide in beside him, laying on your side, facing him. Your heart is racing. Suddenly, this all feels so unbelievably real. The moment that you’ve been dreaming about for months, the moment that you’ve been planning for weeks, is finally about to happen. And so, your heart feels like it’s about to jump out of your chest.
Jolly must have noticed a change in your demeanor, because he speaks up.
“What’s going on in that pretty little head of yours?”
He must have already had an inkling of what exactly you were thinking. You hadn’t exactly held back from being honest during the months before this while you were texting him. You were honest about your fears, wants, desires—and what exactly kept you up at night.
“Just,” you swallow. “It’s a lot.”
“In what way?”
“I’m not too sure. It’s just a lot to process.”
Jolly stays silent for a moment, thinking about your words, giving them weight.
“And that’s okay. We’ll take our time. We don’t have to rush anything. There’s no pressure to even do anything remotely sexual today, not if you don’t feel up to it. I want to make this as easy and enjoyable for you as possible.”
His words settle you a little bit, helping calm your mind. Your body still feels like it’s fighting for survival, though, your heart overworking itself as it threatens to seize out of your chest.
“Can I touch you?” You whisper, the words leaving your mouth before you can stop them.
“Of course, sweet thing. I was waiting for you to ask,” Jolly smiles, staring down at you fondly.
You reach out, placing a hand on his arm. You can’t feel his bare skin, not yet, but still it helps to feel how warm and solid he is, firm and unyielding. It does something to you, feeling just how strong he is. You should be scared of his sheer strength—but you’re not. It only serves to make you feel protected.
“You can cuddle up to me, if that’s what you want. Make yourself comfortable.”
Jolly almost seems amused by your shyness and hesitation to touch him.
Once you’re given permission, you shimmy closer to him, your chest meeting his. God, his chest is rock-fucking-solid and so unbelievably warm. His leg curls around yours, pulling you even closer. One of his arms settles over your waist, his hand resting on your back, holding you. He’s so warm and steady, that it’s impossible to not feel safe and taken care of. His movements feel possessive, but not in an overbearing way. You sigh, melting into his touch.
“Is this okay?” He asks, chuckling at your reaction.
“Yeahhhh. Definitely okay,” you respond, nuzzling your face into his chest without even realising. He smells absolutely delicious. It’s not the scent of artificial cologne—it’s the scent of him, masculine and safe.
Jolly doesn’t comment on it. He wordlessly moves his free hand to begin petting your hair, gently massaging your scalp.
“Oh. That’s nice,” you sigh, eyes shutting at the caring touch.
There’s silence for a little bit as you bask in his touch, before Jolly’s hand retreats from your hair and instead reaches for your chin, gently guiding you up to look at him.
“I think we should talk a little bit more, yeah? About what you want and don’t want to do, boundaries, the stuff we talked about over the phone and all. What I really want to know is how you see today going, and what you’re expecting.”
You pull away a little bit, trying to clear your head and focus after that moment of pure bliss.
“Oh. Well—we’re going to fuck, right? I mean, that’s the end goal.”
“I know that that’s what you’re really here for, but it’s important to not get too caught up in the ‘end goal’. Most importantly of all, we’re here so that I can help you feel good. If we don’t get around to penetration, that’s fine. There’s always another time. I don’t want you to get too worried about that, or rush the process.”
“Okay,” you nod. “Makes sense.”
“I didn’t ask you this over the phone because I felt that it was a bit personal, but could you tell me about any past experiences that you’ve had? I know that you haven’t had many, or even any, but it would be helpful to know. You don’t have to say anything if you don’t want to.”
You think about it. It wouldn’t hurt to tell him.
“Well,” you start. “I messed around with this one guy when I was younger. That’s kind of it. It never went beyond making out or awkward handjobs. I didn’t let him touch me, if that’s what you’re wondering. It was entirely unsatisfying,” you sigh.
“Thank you for telling me,” Jolly hums in appreciation. “Is there anything specific that you know you like or enjoy?”
“Umm well, I think we both know by now that I like praise. A lot. Like, a lot. That’s kind of it, really. I mean, I’m a whore for possessiveness, like you putting a hand around my neck, or manhandling me how you want. That’s pretty hot.”
“Yeah?’ Jolly smiles. “You like being a good girl for me? All mine to do as I please?”
“You can’t use that against me right now,” you whine, very nearly bucking your hips as Jolly smirks.
“Anything else that you like?”
You think about it for a moment.
“Oh! I’ve been reading into this one a little bit, but I kind of like being… embarrassed? That’s not really the right word. Not humiliated or degraded, but just…exposed. I feel like—you feel like such a warm and comforting person, that you’d be able to pull it off really well,” you admit, tucking your face into his neck.
“Aww, you’re so adorable. The sweetest little thing, so eager yet so shy, hmm?”
You whine, hiding your face against his chest.
”You can’t just say things like that,” you complain, your voice muffled.
”How can I resist, though? You’re so unbelievably cute. You keep whining and making these soft little noises—you don’t even know how to respond to half of the things that I say. Yet it’s so obvious that you want me, want my touch. Does that sound about right?”
You nod, face still hidden against his chest.
Jolly pulls back a little bit, just enough to see your face and look into your wide eyes.
“I asked you a question, sweet thing.”
“Yes,” you let out, feeling so unbelievably exposed as your eyes lock with his.
“Yes, what?”
You swallow. “Yes, I want you. Want to feel you,” you whine softly, lowering your voice.
“Is that so?”
”Yes. Need to feel you against me. Want you to touch me,” you whisper.
”C’mon then. You want to start getting undressed for me?”
You nod shyly, staying still—you’re not quite sure how to go about this.
“Don’t worry darling, I’ve got you,” Jolly says as he helps you sit up. He guides you to the edge of the bed, where he kneels down in front of you. “Just going to take some of your clothes off, nothing else for now.”
He reaches for the waistband of your jeans, hands stilling as he meets the fabric.
“Is it okay if I take these off?”
He’s so unbelievably patient, looking up at you and waiting for a response.
“Yes. Please.”
Jolly nods at that, smiling. He unbuttons your jeans, fingers deftly working to unzip them. His hands are warm against your stomach, and you barely muffle a soft gasp when his skin meets yours. You ache to feel his touch somewhere lower.
He pulls down the waistband of your jeans just the slightest bit, enough to expose your stomach as your hoodie rides up.
“You look so soft,” he whispers, eyes dark as he takes in your sheer beauty.
He stills, for just a second, admiring, before resuming his action of taking off your clothes. He continues to take off your jeans, folding them and placing them aside once they’re off.
”God, has anyone ever told you just how beautiful you look?”
You feel so exposed beneath his gaze. If you felt that he could see through you earlier, well then that feeling is amplified at least a hundred times more. You’re not even naked yet, but you feel like you might as well be with how he’s looking at you. His eyes don’t wander down to your crotch, and you’re grateful for that. You’re very obviously wet, but you’re not quite ready for him to comment on it just yet.
“Can I take your hoodie off?”
“Please.”
He helps you with that too, ever so gentle as he moves your arms in order to take it off.
“So beautiful,” he whispers. “Can I take your shirt off too? Or would you rather keep it on?”
”Off, please,” you respond.
He removes your shirt, folding it and placing it with the rest of your clothes. You’re left in just your bra and underwear, shivering under Jolly’s lustful gaze. He’s still clothed—which makes you feel all the worse. Or better. You’re not too sure. His hands reach out, gently taking hold of your hips, his thumbs rubbing soft circles into your skin. His hands are so unbelievably warm against your skin—they emanate a heat that you’re certain has healing properties with how soothing they feel.
“Would you like to help me undress? You can take off just as much as you feel comfortable with, no pressure.”
“I’d love that,” you whisper, your throat dry.
You swap positions with him, standing in front of him while he sits down on the bed.
“Go on,” he encourages, knowing that you’re waiting for his approval.
You reach out for his shirt first—needing to feel the bare skin of his chest. You reach for the topmost button of his collar, fingers shaking a little bit. Your hands accidentally brush against his neck as you continue to the next button, and you can’t help but almost let out a little noise.
You continue to unbutton his shirt, taking your time, not wanting to seem too desperate—though Jolly can see right through you. Once it’s fully unbuttoned, you help guide his arms out of the sleeves. You place the shirt aside, uncaring of where it lands. Your hands reach out and run against one of Jolly’s arms. Photos online of how he looks when shirtless don’t do this man enough justice. His arm is firm beneath your touch, toned—yet his skin is unbelievably soft. You can see some of the veins that run along his arm, and it sends a shiver through you.
Jolly doesn’t say anything, letting you take your time. Your hands wander over to his chest, feeling the skin there. His chest isn’t overly toned, and his stomach still has a little bit of softness to it, which you love. Your fingers trace along his hips, memorising the heat of his skin.
Your hands move downwards, reaching for the belt of his pants. They still, as you look up at Jolly, waiting for his confirmation. He nods, and you begin to unbuckle his belt. Your hands tremble a bit. You hope that he doesn’t notice. Once it’s done, you pull it through the loops, placing it aside. You unzip his trousers, before taking them off of him.
His underwear are also black—boxer shorts that he has no right looking so good in. You stare at his clothed bulge for a little bit too long, zoning out until you hear Jolly softly calling your name.
“Someone’s a little eager, hmm?”
You blush, looking away. He reaches out, holding your hands in his.
“It’s okay. Be a good girl and lie back on the bed for me, okay? I’m just going to dim the lights and light some candles.”
He pulls away and stands up, and you watch as he dims the lights. His back is also toned, and he looks unfairly good turned away from you. This man will be the death of you. You sigh to yourself, sitting down on the bed. You lie back and position yourself how you were earlier, feeling a little bit less exposed under the now soft and subtle glow of the room. You take a few deep breaths, closing your eyes for a moment and willing yourself to relax as you hear the soft click of a lighter, Jolly lighting some candles.
Once he’s done he returns, and you can feel the soft dip of the mattress as he slides in beside you.
“You okay?” He asks as you open your eyes.
“Yeah.” You don’t elaborate, and he doesn’t force you to.
He trusts you to tell the truth.
Jolly lays flat on his back, and motions for you to come closer. You do, and he pulls you in until you’re lying on your side. Your head lays on his shoulder, and he presses one of his legs between yours, keeping it there. You nearly let out a squeak at the action. His leg feels so warm against you, it feels torturous. You cringe a little bit, knowing that you're dripping through your underwear, and he can most definitely feel it. He doesn’t comment on it, though.
One of his hands comes down and rests against your back, tracing soothing shapes and patterns against your skin.
“Whatever we do now, wherever we go from here, just remember that you’re the one in charge. If you say we stop, then we stop. I won’t do anything that you don’t want me to do. I’ll be slow and gentle with you, and I’ll take my time. But above all, I promise that I’ll take good care of you.”
You melt into his touch, his words once again so effortlessly confident yet reassuring. Jolly continues to pet your back with one hand, while the other begins to play with your hair, gently scratching your scalp in the way that makes you shiver. You butt your head into his hand, playfully asking for more attention.
“I’ve noticed that you react really well to physical affection,” he chuckles.
You nod slowly.
“I’m a really… touchy person? I really like physical touch. What we’re doing right now honestly feels like heaven,” you admit shyly, averting your gaze at the honesty of your words.
“Is that so?” Jolly asks, smiling, one hand coming up to cradle your face and rub along your jawline. You melt into his touch, almost making a little chitter of affection. “God you’re so adorable.”
You blush even harder at that, nuzzling your face into his hand in an attempt to hide yourself.
“Stop saying these things.”
He smirks.
“Why? Are you getting too excited?”
“…maybe.”
He moves his leg just the slightest bit, just enough so that you can feel the friction against your clothed pussy. The split-second of attention makes you so unbelievably needy, aching for more. You’re desperate to start feverishly grinding on his leg—yet you stop yourself. You don’t want to come off as too desperate, too needy, too inexperienced (even though, clearly, you were all of these things).
Still though, you can’t hold yourself back from letting out a little whine.
“You gonna grind yourself to completion on my leg? Just make yourself feel good?”
You nod desperately, hips beginning to move, seeking that friction that you so desperately crave. It feels so good—your clothed pussy grinding along his hairy, tattooed thigh. His leg is so firm beneath you, all strong muscle.
Yeah? Does that feel good?” He coos, voice encouraging, yet doing nothing to soothe the heat inside of you. “...or do you need something more than that?”
“Please,” you whine.
“Do you want to take the rest of your clothes off?” He suggests, waiting patiently. He doesn’t pressure you into saying yes.
“Yes. I need you,” you beg. “Need to feel you.”
You stare up at him with wide, pleading eyes. He can't even bear trying to tease or deny you.
Jolly sits up a little and begins to rearrange you, propping you up against the pillows so that you’re half sitting, half lying down. He sits to the side of you, one hand resting on your thigh, massaging light circles into your skin, before leaning down and leaving a soft kiss on your thigh. It makes your heart flutter, feeling his hot breath so close to your still clothed, aching pussy. He pulls back, and one of his hands runs over the edge of your bra, while the other traces the pattern of lace that adorns your underwear. It makes your breathing pick up, your breaths rushed and desperate.
“God, your thighs are so beautiful. Can I take these off for you, sweet thing?”
You nod eagerly, before remembering the rules and rushing out a desperate “yes”.
“So eager,” he comments, smiling, before reaching around to your back. You sit up a little bit, giving him some space to work with. With one hand, he deftly unhooks your bra, taking it off you and placing it to the side. He simply stares at you, adoring the sight.
“You look beautiful," he whispers reverently.
You blush, looking away. Jolly gently grabs your face, before guiding you to look at him. He leans in, placing a soft kiss on your clavicle, his breath warm and steadying. The action makes your heart flutter. His hands gently rub at your sides, grounding you. They trail down slowly, before his fingers glide under the waistband of your underwear. He looks up at you again, judging your reaction, making sure that you’re okay with this and fully comfortable with what’s happening.
You nod, sensing his need for reassurance.
Jolly continues, hooking his fingers into the waistband of your underwear and gently guiding it down your legs. He doesn’t stop, doesn’t look up at you until they’re off. Only then, does he look at your bare pussy, hidden by your closed legs.
“C’mon sweet thing, spread those legs for me,” he coaxes.
You blush, looking away, before doing as he says. You can feel him staring at you. You feel naked, exposed, embarassed—yet that still doesn’t stop the thrum of desire inside of you. Jolly moves so that he’s right in front of you, and repositions your legs so that he can easily access your pussy.
Only then, does he touch you. His hands start off on your stomach, gently massaging it before slowly moving down. His touch is gentle, patient, letting you grow accustomed to this new sensation.
His hands move down towards your pussy, and your breath hitches, awaiting his touch. Yet, his hands skip over it and caress the inside of your thighs, rubbing soothing circles while he smirks at you. You let out a little whine of displeasure, making your unhappiness with his actions known.
“I know, I know love. I’m just getting you warmed up a little bit. Can’t have you getting too excited, hmm?”
You buck your hips up a little bit, making a small noise. Jolly seems to finally relent on you, as his hands wander further up, finally touching your pussy.
He runs one finger along your center, collecting your slick. His motions are slow—exploratory, teasing.
“God, you’re so wet. All for me.”
You whine, stomach tensing and muscles shaking as finally, you’re being touched, receiving the attention that you so desperately craved. His finger retreats, as he brings it up to his mouth and licks off your slick, letting out an appreciative hum.
“You taste so good,” he praises, groaning.
His hands find your pussy again, this time spreading your folds and looking right at your hole. You can’t help but blush. You don’t even bother looking away, knowing that he’ll just make you look at him again. You’re pinned underneath him, his hungry and predatory gaze boring right through you. Still spreading you open, his thumb comes down, running along the opening of your pussy. He doesn’t press inside—he simply caresses it, teasing you in a way that only serves to drive you mad.
“There we go. There’s that sweet little pussy. You’re absolutely dripping for me, making such a mess.”
He leans in, and you feel his hot breath against your center. He’s so close to you that you stop breathing, awaiting his every action. His tongue darts out, leaving a firm lick against your pussy. The action, though quick and simple, makes you tremble.
“Need to breed this pretty pussy. Need to see my cum dripping out of it.”
You whine, bucking into his touch. His words are doing something unholy to you, and your thoughts are about ten steps ahead of his actions.
“Yeah? You like that?”
You nod desperately, unable to find the right words.
“You want me to breed your pussy? Fill it until it’s dripping and you can’t take it anymore?”
Again, you nod frantically. His fingers find you again, gently trailing along your folds, spreading the wetness. He doesn’t provide any more stimulation, though—just gentle, teasing touches, that simply aren’t enough to quench your desire.
“Please,” you beg, voice high-pitched and whiny.
“Please, what?”
You mumble out something unintelligible that he can’t quite catch.
“C’mon, sweet thing. You can tell me.”
“Don’t make me say it,” you whine, averting your gaze.
Jolly clicks his tongue, chiding you. “Remember what we talked about? You have to be honest with me—I can’t read your mind.”
You sigh, giving in. “I want you to fuck me,” you mumble, hoping it was loud enough.
“Okay, wow. Don’t get too enthusiastic about it.”
You laugh, the action making your chest feel the slightest bit lighter. You gaze up at him again, eyes wide, wordlessly begging.
“Okay, let’s move you around a little bit,” he says.
He sits up, and slots himself in behind you. He’s now sitting against the headboard, with you in front of him. Sitting with your back to his chest, Jolly’s legs wind around yours, moving them until his legs are pinning yours down, keeping them spread open. His hands wander along your bare thighs, softly rubbing them. You shiver, feeling so utterly exposed as he holds you open. You can’t even close your legs, and it sends a chill running through you.
“C’mon on, talk to me. I can hear your thoughts. Be honest. What are you thinking?” He mumbles into your ear as he continues to touch your thighs.
“I’m worried—I’m worried that it’ll hurt,” you admit weakly.
“Yeah?” He coos, giving you space to elaborate.
”Yeah.”
”Have you been stretching yourself out like we discussed?”
”Yes! I have been, over the last week. It’s a lot, though. My fingers are so much smaller than yours and I can’t even comfortably take more than two.”
Jolly thinks about it for a moment, staying silent.
“You’re in safe hands. I’ve got you. I’ll take care of you. I want to make this as pleasurable of an experience for you as possible. I promise that I’ll be slow, and stretch you out gently.”
You couldn’t help but buck into his touch at that. His respect and care for you turned you on more than anything. In his arms, you knew that you were safe.
“It’s okay, sweet thing. I’ve got you. I’ll help you feel good, yeah?”
You nod frantically, desperate for him to finally, properly touch you.
“Touch yourself for me.”
You hesitate, letting out a whine. That isn’t what you wanted.
“That wasn’t a question. C’mon, I want to see you play with your pussy.”
You whimper at his tone of voice—commanding yet effortlessly seductive. After looking back at Jolly and meeting his unwavering gaze, you reluctantly lower your hand down between your legs. The action makes your face burn. It feels humiliating—though you’re not quite sure why.
“There we go. Touch yourself, sweet thing. Make yourself feel good, yeah? We need to get you all nice and relaxed.”
You’re hesitant in your actions. You take it slow at first, not wanting to overwhelm yourself. Jolly’s soft praise and gentle words spur you on, though. Whispered words of “I’ve got you,” and “good girl,” are enough to encourage you to be bolder in your actions. Soon enough, you touch yourself the way that you usually would when alone.
It doesn’t take long for you to fall over the edge—not with Jolly’s thick fingers wandering along your thighs, his gravelly voice in your ear, his warm chest pressed against you. You know that he’ll take care of you, and so your body doesn’t hesitate in letting go, shaking and trembling as your orgasm washes over you.
“There we go, sweet thing,” Jolly coos. He brings two of his fingers down to swipe through your wetness.
After doing so, he looks at them, admiring your slick. You blush, looking away.
“C’mon, open that mouth for me.”
You don't hesitate to obey. His fingers glide past your lips and rest on your tongue. His touch isn’t rough or even demanding—his fingers simply stay there, allowing you to explore them at your own pace. You moan around them, moving your head slightly so that they rest a little bit further down your throat. This soon after an orgasm, the feeling is intoxicating. You feel thoroughly taken care of, your thoughts beginning to relax a bit, your heart not beating as fast anymore. Your head feels a little bit cloudy.
You’re not sure how long you sit there, letting out soft noises as Jolly’s fingers stay in your mouth. Eventually, he pulls them out slowly, and you whine, chasing them as they retreat.
He hushes you softly, bringing his hand down and touching your pussy. His touch is gentle, slow, checking to see if you’re still sensitive. His saliva-covered fingers feel so unbelievably good against you, warm and wet in the best possible way.
Despite having only just orgasmed, you still feel a deep need inside of you. Your pussy clenches around nothing, desperate for something to fill it. Jolly, noticing your squirming, teasingly rests a finger against your entrance. You try to buck your hips, moving as much as you can, but it’s not much use. His legs are still pinning you down, and his other hand wraps around your waist, holding you close. There’s not much that you can do, other than beg.
“Please,” you whine.
“Please, what?”
“I need you. Need you inside of me.”
“Is that so?”
“Yes,” you whine. “Need to feel your fingers. Please.”
Wordlessly, Jolly reaches towards the bedside table, opening a drawer and retrieving a bottle of lube. You watch, entranced, as he coats his fingers in the substance. Once he’s done, his finger rests against the entrance of your pussy, rubbing little circles against it, in the way that drives you mad.
“Relax for me, sweet thing.”
His finger slowly pushes in. It doesn’t take much effort. You can take one finger fairly easily—even though his fingers are much larger than yours. Your pussy is already so wet and relaxed, and along with the added lube, his finger slides inside without much reistance.
“God, your pussy is so soft. So tight and wet, all for me. I can’t wait to see my cum spilling out of it.”
Your brain is on overdrive, frying at the simple fact that Jolly now has one of his fingers inside of you. His thick, calloused, tattooed finger is slowly working inside of your pussy, gently moving, trying to slowly stretch you and simultaneously make you feel good.
Because he’s holding you against him, not a single movement of yours is lost on him. He can feel every squirm, every little jolt, every tiny gasp of yours.
And he wouldn’t have it any other way.
After working you open a little bit, and turning you into a whiny, gasping mess, Jolly suggests adding another finger. You nod frantically, a desperate “yes,” tumbling from you.
You tense a little bit as his second finger enters you. It’s much more of a stretch, no doubt about it, but Jolly comforts you through it.
“There we go. Just breathe through it, okay? It’s okay, you’ve got this.”
He’s so gentle in his touch, pushing his fingers inside of you ever-so-slowly. He takes his time, patient and calm, waiting and watching your reactions.
His two fingers are so much thicker than two of yours. You can feel a little bit of a burning stretch, but Jolly’s words softly soothe it.
Soon enough, he’s got two of his fingers nestled inside of you. He moves them slowly, crooking them and trying to find the spot that makes you gasp. They feel so deliciously good inside of you—filling you up in the best way possible. They make you feel a deep sense of satisfaction and fulfill a craving that your own fingers can never seem to achieve. You struggle to get your own fingers deep enough to where it actually fulfills your desire—they’re just not long enough to hit the spot that makes you feel good. Meanwhile, Jolly’s fingers are perfect—filling you up with how long and thick they are.
Still though, you ache for something else inside of you.
Jolly keeps working your pussy open, gently moving his fingers further apart, little by little. He keeps angling them against that one spot that makes you want to go boneless. It’s nowhere near enough to make you cum—but the pleasure is still very much welcome. It distracts you from the slight stretch that you feel.
After a while, you can feel a third finger rest against your entrance.
“Do you think you can take a third one?” Jolly asks, waiting patiently. He doesn’t push.
The idea scares you. Two fingers is a lot—but three? Realistically you know that his dick is much bigger anyway, and will be much more of a stretch than three fingers. Still, you can’t lie and say that the idea of taking three of his thick fingers isn’t scaring you.
Still, you nod.
“I need words,” he chides you gently.
“Yes. I can take three.”
He slowly removes both of his fingers from you. You whine at the emptiness, clenching around nothing. Jolly spreads some more lube on his fingers.
Jolly gently works the tips of his three fingers inside of you. You can’t lie—it does hurt quite a bit. Little distressed noises rise from the back of your throat, as Jolly rushes to comfort you. His hand around your waist holds you close, rubbing little circles against your side. He whispers praise and reassurance in between the kisses that he leaves along your neck and shoulder.
“I know it’s a lot, but I need you to relax for me. If you’re tense, it’ll just make it hurt more,” he whispers against your skin.
“It’s—it’s just a lot.”
”I know, sweet thing. That’s okay. But please, try your best to relax, okay?”
You nod, leaning your head back and letting it rest against his shoulder.
His fingers work you open, slowly but surely sliding further inside of you. It’s a long process, and it takes quite a while—but Jolly slowly works with you and your body. He gently eases his fingers inside, until finally, you’ve taken them fully.
“There we go. You’re taking my fingers so well, doing so well for me,” Jolly coos.
He moves his fingers around a little bit, trying to stretch you some more. You feel so unbelievably full, and his fingers moving inside of you only spur on that feeling. You’re not quite sure what’s going on anymore. Your mind feels unbelievably blissed out, completely gone from the present moment. Mentally and physically, you feel stretched beyond what you’re able to comprehend.
At some point, you notice that Jolly’s fingers are gone. You let out a whine, your pussy so empty that it feels wrong.
“Need you. Please,” you whine out.
“What do you need from me, love?”
“Need your dick inside me. Please,” you gasp, your hips bucking against nothing. It doesn’t help that you can feel him against your ass, his dick hard and aching for attention. You try to grind down on it, but Jolly has you in a firm grip.
“It’s okay love. I’ll take care of you.”
Jolly begins to reposition the two of you. He lays you down on your back, fixing the pillows behind your head so that you’re comfortable. He takes one pillow and slots it underneath your hips, positioning in so that you’ll be more comfortable. He moves between your legs, spreading them. He’s transfixed by the sight of your pussy, wet and begging for attention.
Only then does he take off his underwear. You watch, transfixed and curious at the sight of his dick. It looks painfully hard, and the tip is cherry red and already leaking. You can't deny that you’re flattered. You’re not concerned about the length of it—but the thickness of it makes it look like it could split you apart.
“See something you like?” Jolly asks, smiling as he uses one hand to stroke his dick.
The sheer size of it jolts you out of your stupour.
“I can’t—it’s too big,” you state firmly.
Jolly chuckles at that. His free hand reaches out to rub at your thigh, squeezing it in reassurance.
“It’s okay. I promise I’ll be gentle.”
And you trust him. You really do. He’s been nothing but sweet to you so far. But the idea of that being the first dick that you’re ever going to take is scary.
“It’s massive.” Your tone of voice leaves no room for arguments.
Still, Jolly laughs. “Trust me, it’s about average. I know it might seem scary, because you’ve never taken one before—but trust me when I say that this is nothing to worry about.”
“Promise you’ll be gentle?” You ask.
You know that he will be, there’s no doubt about it—but still, you need to hear it again. At such a vulnerable moment, you’re desperate for any reassurance.
“I promise. I’ll take my time with you, and I’ll make sure that you feel good. I promise.”
You nod.
“You ready?” He asks.
“Yes. Please. I need you so badly.”
Jolly spreads some lube on his dick, and gets closer to you. He rests the tip of his dick against the opening of your pussy, and you can’t help but gasp. It feels so wet, so warm, so intimate. His free hand grabs your hand, fingers interlacing. He uses his other hand to slowly guide his hard dick into your pussy. He slowly pushes into you, almost agonisingly patient. He only enters you the tiniest amount, eyes trained on your face and gauging your reaction.
“Is this okay?” He asks, reaching out and stroking a strand of your hair back from your face, tucking it behind your ear. He smiles down at you, looking unbelievably fond. He can’t help it.
You nod, letting out a tiny squeak of a ‘yes’.
“I’m going to keep going. Tell me if you need to stop, sweet thing.”
Again you nod, too overwhelmed to use your words. Jolly seems to understand it though, for once not pushing for a verbal answer from you. The stretch of his dick slowly stretching you feels so overwhelming. You can feel an undercurrent of pain, but you’re not surprised. You just hope that it goes away soon.
Jolly proceeds to slowly enter you, moving only the slightest bit deeper once he’s sure that you’re okay. Throughout it all, he whispers words of praise and reassurance, his tone of voice soft and patient. Despite the pleasure mixing with a slight pain, you still feel like you could cry, simply from how gentle he’s being with you.
Eventually, after what feels like forever, Jolly’s dick is fully enveloped by your pussy, his hips meeting yours.
“There we go, sweet thing. Just breathe through it. Slow, deep, breaths, yeah?” He says as he stills his movements, letting you adjust to the size.
“It's too big,” you whine. It doesn’t hurt too much, per se. It’s just a lot to deal with. The stretch feels overwhelming and unfamiliar, you’ve never felt like this before. It feels like his dick is absolutely ruining you. You swear you can feel him deep in your stomach. He’s filling you so thoroughly, in a way that you didn’t even know was possible.
“It’s okay baby, I’ve got you. I’ll help you take it, okay?” He reassures you, his free hand reaching down to your hip and holding it, rubbing soothing circles into your side.
You nod, mind clouded and train of thought foggy.
“Just try your best to relax for me. I’m not going anywhere. I won’t move until you’re ready. I’ve got you, love.”
Jolly keeps his word, staying still, not moving his hips the slightest inch. He’s so unbelievably patient, so tender and gentle with you, that it makes you want to cry. He’s too nice to you. This is a far cry from that one guy you messed around with when you were younger, and you’re so unbelievably grateful for this.
“I can feel you tensing your pussy a little bit. Try to relax her, okay? Let your poor pussy relax, she’s working so hard to fit me.”
You whine, barely being able to follow his instructions with how clouded your mind is. You’re floating, gone, barely able to think.
Jolly reaches down and begins to slowly stimulate your clit, rubbing soft circles. It turns you into a whining, gasping mess, trembling underneath him. Nonsensical words drift from your lips, your eyes fluttering shut. Soon enough, you’re clenching around him, your pussy spasming around his throbbing dick as he works you to your orgasm. He removes his hand from you once you start to make noises of overstimulation.
“Better?” He asks, smiling down at you.
“Feels so good,” you whisper. “Please move. I need to feel you. Been waiting for so long.”
Jolly slowly begins to pull out until just the tip is left inside of you, before beginning to push back in. He’s gentle, careful, watching and judging your every reaction.
It feels so blissfully good when he pushes back in, filling you up even deeper than you thought was possible. Listening to your moans, he slowly begins to speed up his thrusts, making sure to pay attention to every reaction of yours. It’s not fast or rough by any means—it’s a perfect pace that doesn’t force more than you can take, yet still leaves you gasping in pleasure.
“You feel so good, your pussy is so tight around me,” Jolly groans.
You move your legs behind him, pulling him even closer to you. This new angle allows him to easily hit that one spot inside of you, the one that makes you see stars whenever he brushes against it.
“Please breed me,” you whine, clenching around him. There’s nothing more that you want than to feel his warm cum filling you.
His thrusts get a little bit more frenzied, as he chases his release.
“I can’t wait to breed this sweet pussy of yours, see my cum spilling out of your tight pussy—“
It doesn’t take much longer after that. His own words seem to spur him on.
You can feel Jolly’s dick pulsing inside of you, filling you up with his cum. It feels so wet, so warm, so perfect. Through it all, he’s working your clit, and soon enough, you cum too, clenching around his dick and milking it of his cum.
Jolly nearly collapses on top of you, his soft chest pressing against yours. He tries to pull out of you, but you whine, locking your legs around his hips.
“Wanna feel you for a little bit longer,” you manage to gasp out. You don’t know how you find the strength to talk.
The two of you lay there, Jolly blanketing you with his body, as your mind comes down from its high. Your heart is racing, your breathing is unsteady—yet you feel blissfully at peace. Your eyes shut, basking in the peaceful moment.
It takes a few more minutes for Jolly to soften, at which point he gently pulls out.
“Hey there,” he says, staring down at you, a slight, self-satisfied smile on his lips.
“Hi,” you respond shyly, reverently gazing up at him. You feel so exposed, laid bare—yet still you look up at him in wonder. You can’t really think much, your head feels too clouded and foggy. Yet still, you’re filled with an overwhelming feeling of care and tenderness.
Jolly slowly leans down to kiss you, and you don’t try to escape. You melt into his touch, his warm lips meeting yours. His hands come up to cradle your face, his thumbs rubbing along your cheeks. It feels so right, so perfect.
He’s blushing slightly when he pulls away, the tips of his ears tinged red. It’s endearingly adorable.
“Was that okay?” He asks.
You’re not sure if he means the sex or the kiss. Either way, the answer is the same. “It was perfect.”
Jolly moves you so that your positions are swapped, with you lying on top of Jolly, facing him. You spend the next few minutes simply cuddling, basking in each other's heat. His bare skin feels so unbelievably good against yours, his body soft yet also firm. His hand comes up to your head, gently stroking your hair. You trace your finger along his tattoos, getting lost in the vivid designs. You can feel his cum beginning to leak out of you, but you don’t pay it any mind.
You feel your eyes beginning to drift shut, and that’s when Jolly notices it too.
“Hey sweet thing, don’t fall asleep just yet, okay? We gotta wash you, get you all nice and clean, yeah?”
“Don’t wanna,” you mumble, burying your face into his neck.
He lets out a soft laugh at that. “C’mon baby, we gotta get you clean. I promise that you’ll feel so much better afterwards.”
“You’re so evil,” you whine.
He smiles at that. “How about I run you a bath, and come get you when it’s ready? If that’s okay with you.”
You agree to that, yawning and nuzzling into his neck. Jolly slowly detaches himself from you, being careful not to jostle you too much. He pauses for a second, debating whether it’s a good idea to leave you alone, even for a little bit—but you snuggle right into the bed. He smiles. He retreats into the bathroom, and you can hear the sound of the bathtub filling up. You drift in and out of sleep, in a semi-conscious state that feels like pure bliss.
Eventually, Jolly returns. He pets your hair for a little while, until he sees your eyes flutter open. He then gently guides you to sit up, and you groan. You can’t deny the fact that your pussy hurts whenever you sit down or put pressure on it.
”Hurts?” Jolly asks, as you nod. “I’m so sorry darling, I should have been gentler.”
You shake your head, reaching out for him, making grabby hands. You leave another kiss on his lips. “You were perfect. Thank you.”
He smiles at that, his eyes staring deeply into yours. You swear that there’s an emotion in them that you can’t quite make out.
“C’mon, let’s get you washed.”
He doesn’t hesitate before picking you up, bridal-style. One arm behind your back while the other one rests underneath your bent knees. He brings you into the bathroom, dimming the lights so that it’s not too bright. He then sets you in the bathtub. You groan a little bit as the hot water touches your pussy. It hurts a little bit at first, but soon the heat only serves to help dissipate the pain.
Jolly removes his underwear, before sliding in behind you. He moves you so that you’re fully resting against him, your back supported by his chest.
“Can I wash your hair?” He asks. You agree, closing your eyes as you sink into the blissful feeling that envelops you.
You don’t remember much of the aftermath. You were tired, sleepy, and so utterly relaxed and content. You remember floating in the warm bath, Jolly’s soft chest supporting your back. Jolly’s hands working through your hair, massaging your scalp and sorting through the tangles. A warm, fluffy towel enveloping you afterwards, another one gently drying your hair. Jolly fetching a fresh set of underwear from your bag, helping you put it on, finishing it off with one of his soft, faded band shirts that smells like him.
Once the sheets are changed, the two of you crawl into bed once more. Jolly doesn’t hesitate before pulling you closer to him, holding you so that you’re secure against him. He acts as your personal heater, body emanating a warmth that you happily bask in.
Soon, you drift off, but not before Jolly places a soft kiss against your forehead.
“Thank you for trusting me,” he whispers.
lmk if you'd like to see more because i do have some other stuff planned out for these two!!!
Dividers: @/silent-stories
Taglist: @theservantbones @itsfarbettertolearn @pipidoll @lacy1986 @fadingangelwisp @concretejunglefm @oobleoob @english-fucker @sallyba3 @111amyyy @findinggodb3for3godfindsm3 @darksigns-exe @sleepycactus-offering
