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hellsslibrary · 8 months ago

Note

your twisted wonderland first time stories are so good! is it fine if i request you write about vil, rook, jade, leona, and cater next? i love top male reader stories but its hard to find ones about twisted wonderland :<

-🍤

»—> Vil's, Rook's, Jade's, Leona's and Cater's first time + Azul from another request.

#a.n. : my writer's block and problems in life are finally over and I'm writing again. An amazing sight, but still.

#cw/tw: top!male!reader, bottom!male!character, first time obviously, praise kink, fingering, teasing, and quite a vanilla sex in general, sex toy(Cater), riding(Leona), very little nipple play(Leona), dirty talk(Rook), Rook is a brat just a little.

This is definitely a planned action, simply from the fact that Vil more than knows about sex (I think Eric explained this to him as a child as needed). Therefore, it is at least planned on the part of your yes/no, preferences and the like.

I don’t know why, but it seems to me that it’s important for Vil that your first sex with him be vanilla and romantic. That is, so that this sex is not so much a show of your lust, but of intimacy, your trust in each other.

If you are not a virgin, by the way, you will think that you are a virgin. This guy will guide you as if he knows everything, where, what and why (although he didn’t go beyond jerking off, because he didn’t see the need for it).

But he will still give you control, almost completely, simply because... It’s more convenient for a virgin than to do it all himself.

“Mmm... Yeah, it feels good,” Vil mutters as your fingers poke into that sweet spot and his fingers curl into the sheets. “Please continue... A little slower, yes, like that.”

A quiet moan of pleasure escapes his lips as your fingers slow down ever so slightly, pressing with each slow but rhythmic thrust into him. He sighs shakily, his arms wrapping around your neck as he presses a chaste kiss to your lips.

"Vil? This..." You whisper, watching as he spreads his legs beneath you invitingly, a smirk blooming on his lips that turns into a smile of pleasure in a matter of seconds. "Too tempting for a virgin."

"In your opinion, I'm always tempting, no? Or do you think I don't notice your glances at my ass?" Vil asks, chuckling and making you laugh too and kiss his lips, in a deeper way, and push your fingers even deeper.

It is clear that the sensations will be strange. But he’s still pleased, and the main thing is that it’s you. And Vil is not one of those who goes back on his word, after all. And if he allowed you to fuck him, then you will do it (if you want, ofc).

Vil simply found some kind of peace in this first act. Slow thrusts, your hands touching his body, which has become like a continuous erogenous zone, your quiet voice whispering praises and compliments to him... It's wonderful.

“Ah, [M-Mc]... It’s so good, don’t stop, I beg you, my love,” Vil whispers, closing his eyes in pleasure, feeling the relaxed, slow tremors inside him; a whine escapes his lips as you lift his hips off the pillow, going deeper.

“So good... You take cock too well, handsome. Although it’s you, what else could I expect,” Your whisper is heard in his ear, and he melts at the sound of your hoarse laugh.

His nails dig into your back, creating crescent-shaped marks. His hips rock in time with your thrusts, meeting them. Moans and whines escaped his slightly reddened lips from the kiss, mixed with the sound of your name... Just perfect.

I'm honestly not sure if this was planned or not. Just from the fact that I can easily imagine something innocent with him developing into something obviously intimate and... I'll leave it up to you.

And you DO NOT need to discuss the main important things before getting into bed. He knows everything about you, which seems strange, especially if you have never even thought about it, but this is Rook... But he will tell you his boundaries and what he loves, yes.

He is absolutely calm before the penetration begins, absolutely. You even begin to think that he lied, that this was his first time. He's too... Stretched for a virgin. (Although let's be honest, I just think he was playing with himself. And I think he's one of the few people who did it with his hole, lol)

He doesn't moan at all before the penetration begins, like AT ALL. Rook just watches your fingers penetrate him with a satisfied smile and red cheeks and tells you all sorts of praise and some phrases that make you swear you want to simultaneously blush and hit him at the same time.

“Mmm... Your fingers are so good, Mon cher, it’s almost unbearably good. If you’re so good with your hands, then I can’t even imagine what it will be like when your dick is inside,” Rook whispers with a half grin, half smile on his face, his palms lie on your chest, drawing some invisible patterns there with his fingers.

A sigh escapes your lips and you lightly slap him on the back of his thigh, causing Rook to twitch slightly but only chuckle at your displeasure showing; his back arches when you make deliberate, harsh contact with his prostate.

“Rook, I ask you, keep quiet... Everything has its time. Have you heard of such a phrase?” You ask a rhetorical question, and a joyful glint appears in his eyes when he realizes that he has angered you just a little.

He's also calm when you finally insert your dick, it's like he's done this all before, seriously. Although moans are already beginning to escape his lips, he still does not stop these dirty conversations, they even intensify.

Although they soon turn into only convulsive declarations of love and praise when he approaches orgasm or this happens after the first orgasm.

"Ahh... You're so deep, it's incredible! Don't stop, please," Rook ululates as his face slams into the pillow again, squeezing it in his grip, causing it to tear pitifully.

“I didn’t plan on stopping, blondie, don’t worry,” He trembles when he hears and feels your whisper right next to his ear.

Your tender kiss behind his ear absolutely does not fit with the rough and rather sharp thrusts, creating a wonderful difference between roughness and tenderness... And damn, he can feel how his dick is getting hard again.

... No, I don't think it was planned, no. But this was not something wild too. It’s just that at some point you smoothly flowed into intimacy when there was the most suitable time and moment for this.

Although you have probably discussed similar topics with him many times before. I just think he's terribly curious when it comes to his partner, plus he probably doesn't have much of an idea of how sex works between someone who has legs.

An absolute mess. He gradually, but quickly enough breaks down under any of your actions, touch, word, even glance. He simply surrenders to these sensations headlong.

"Jade, are you okay? You haven't said a word since my fingers were inside..." A question leaves your lips as you watch Jade try his best to hold back any sounds that escape his lips, and he just nods, "Baby... Give me a verbal answer."

"Y-yes! This—... Th-this is so good, mmhmm... Plea-please don't, agh, st-stop!" Jade groans, barely able to utter the words, causing a chuckle to escape your lips, causing the moray eel’s already red cheeks to turn an even darker shade.

His body trembles, his hands grab at anything just to maintain a little sense of reality. His cheeks are completely red, his teeth are nipping at his bottom lip, his eyes are closed as tears stream down his face... What a charm, right?

You'll probably need to keep his mouth closed somehow when you finally enter him. He will no longer be able to control his moans, and he will moan so damn loudly.

He doesn't even feel discomfort, he just wants all of you. He wants you to go ahead and just fuck him like he deserves.

“Hush, precious, hush. You'll wake everyone up, these aren't soundproof walls after all,” You whisper as Jade's head is thrown back on your shoulder in pleasure, and your fingers are in his mouth, playing with his tongue to muffle him just a little.

Your other hand lowers and lifts his body on your dick, making him twitch and whimper every time. His thoughts are jumbled, if he can think at all right now. Now there is only you, him and your dick, which lies perfectly in him.

No, this is not planned. I think it was completely unplanned. For some reason, I imagine him sending you a repost of some video where there is something sexual and like, “Maybe we can do it too?))”

And if you agree, he is the happiest in the world. He expected that you would not agree and then he would have reduced everything to a joke, but since you agree...

He also probably once tried to finger himself, but he didn’t really succeed, because his fingers didn’t reach what he needed, so he maybe used toys, or didn’t touch his hole for the time being.

"Mmm, are you sure this thing is comfortable, pumpkin? Is everything wonderful?" You ask to make sure he's absolutely fine as he lies on the bed, fascinated by the toy below.

"Y-yes... It feels good, really," Cater whispers, moaning as the toy touches his prostate. It's just a prostate vibrator with a circle of rubber that attaches to the base of the penis... But he swears it's never felt as good as it does now.

An absolute mess when you penetrate him. He's quiet though, I guess. You feel so much better than anything in his life has ever felt. And... A real cock is probably more pleasant to have than rubber, glass or other materials.

And yes, he won't let you go. He will cling to you with all his might, but he will still hold on to you.

“Cater... Calm down, calm down. I’m not going anywhere,” You whisper as his nails run down your back for the hundredth time in these moment, leaving red marks there that will clearly make your tomorrow less rosy.

“So-sorry,” He sobs, wrapping his legs around your waist, practically hanging on you as you continue to thrust in and out of him at a slow pace, “You're just... So h-hot and wet inside... And twitching, too! Weird..."

I think this is more about presenting you with a fact rather than a planned action. He can just lie on your lap in the garden and then say something like “I want to have sex tonight” and start snoring a few seconds later, and you react however you want.

For the first time he is surprisingly active, I think. Really active. Of course, he doesn’t know how to do anything in practice, but if you want him to suck you off or something, he will do it. (And will still do it damn well)

Quiet asf. Just a few growls, maybe very quiet moans, but it’s hard to get him to other sounds. In general, I think that he is not particularly sensitive himself.

“Mmm, come on, herbivore... I'm not glass, damn it,” Leona mutters as you slip your fingers into him a little too slowly for his liking and he sighs contentedly when you speed up a little.

"Sorry, sorry. I just don't want to rush anywhere, okay?" You speak, specifically aiming for his prostate and he just makes some kind of guttural sound reminiscent of agreement.

He will ride you. Yes, you can fight me, I’m ready, but he will do it. Leona wants to control the pace of your first time, so he will do that.

Although, of course, when he gets tired, he’ll just lie on top of your chest and you’ll have to fuck him like that because it’s convenient for him, lmao.

"Ha... Leona, you look incredible when you're on top of me, you know?" You ask, looking at him riding your dick at a slow, but quite sharp pace, while his hands lie on your chest, sometimes squeezing it convulsively in his palms.

“Yeah, I always look incredible actually... But I'm glad you recognized my greatness in a position that no one else saw,” Leona whispers with a smirk, flicking your nipple lightly, chuckling as you twitch inside him, but then it’s his turn to moan as you lift your hips, meeting his bounce halfway.

Yes, considering him, this is planned. He was very nervous, thinking that something would go wrong, so he discussed it with you in advance and of course asked when, after the start of the relationship, you would feel comfortable taking this step.

He is absolutely nervous before starting, even if he has read a lot of educational literature on this topic. He thinks something will go wrong or you won't like something.

He... Something between quiet and loud, yes. The most common moans, whines and sighs. Although, if you overstimulate him or just bring him into some kind of faint state of ecstasy, he will sound like the girls from hentai, I swear.

"Azul... Relax, okay? You're pretty tight even for a virgin," You whisper, squeezing his thigh reassuringly, letting him know that you're here and you're not going anywhere.

He nods, wiping his eyes from the accumulated tears, although it didn't really help, because they almost immediately appeared again. Azul sighs deeply, taking one of his pillows and covering his face halfway as he continues to stare at you.

“Okay, sorry... It's just unusual, I didn't think people walking on two legs felt this way,” Azul mumbles, muffled by the pillow but surprisingly able to keep his voice unwavering, throwing his head back when you touch his G-spot.

The absolute prince of pillows, at least the first few times. It's not that he wouldn't want to do something. He's just embarrassed and has no idea what to do.

Definitely a very kisser. Firstly, to muffle his moans, which make him ashamed. And secondly, it seems to me that he has a sensitive mouth and tongue... And his throat too, if you have a long tongue.

Azul meets your lips with his own again as he lies on his back, his legs twitching on your shoulders from the thrusts inside him. His tongue slides awkwardly against you as you run the wet muscle over his teeth for the hundredth time that evening and then pull away.

“You're so cute, Azul... I had no idea you'd be so clingy,” He blushes when he hears you whisper against his ear and squeezes his eyes shut when you lick the shell of his ear.

“It’s not true, love... Don’t tease me,” Azul mutters, covering his face with his hands, although he immediately leans forward when you kiss him again.

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