From one of the smut days of the event, I used the below prompt for some of the teachers from Welcome to Demon School, Iruma-kun! It was such a fun ask and I enjoyed writing these, so I hope you lovely constant readers enjoy them as well. Where things didn't get too smutty, I didn't really feel the need to hide anything under a cut and hope that doesn't bother anyone.
SEND [LOSER] FOR THE CHARACTER’S REACTION TO YOU PLAYING THE WINNING HAND IN STRIP POKER
It was actually really damn hard to get Kalego to play strip poker in the first place. It’s not a game he would naturally be okay with playing – he thinks the whole thing is really stupid, something he makes clear at every single step of the game. You really only get him to play by striking blows against his ego and pride. While he took a couple blows to his ego, took a couple comments about how scared he must be about losing and having to show how inadequate he was, when the comments started getting more pointed and meanly stated, you know you’ve hooked him.
He’s a little scary and you’re really rather intimidated during the first few rounds. It’s why you kind of flub the first few hands. At least, that’s what you allow him to think. You want him to think he’s getting into your head, that he’s got you scared. You’re down to just your undergarments before you start your actual plan.
In truth, you’re kind of used to hustling poker games. It’s really one of your specialties. You know you have this in the bag, but you manage to keep the smirk off your face as you start winning hand after hand. It’s not long before Kalego is caught up to you in terms of states of undress.
You let him win a hand, take off your bra, get him a little distracted. It helps you win a little easier.
You throw down the winning hand, cocky smirk all over your face, teasing him as you demand he strip.
But it’s Kalego. Did you really expect things to be that easy?
Kalego’s surprisingly honorable. He’d never welsh on a bet, right? As much as it pains him, he’d strip and accept the loss and just harbor an insane grudge, right?
Thing you forgot about Kalego though…his crazy students and the sheer amount of trouble that seems to follow him around. Which is why, one moment, he’s there, and the next moment, he’s gone.
Meanwhile, Flufflego the familiar is really wishing Iruma had summoned him a little while back, when he’d been a bit more dressed. This is one time he hopes he gets to stay in familiar form for quite a while.
Raim is actually pretty easy to talk into playing the game. To her, it’s all good fun, especially as it’s a game she’s known to play really well. Most of the time, the more clothes she loses, the worse at the game her opponent becomes, distracted by the ample flesh exposed in front of their eyes and the sexiness displayed by her.
It’s extremely rare for anyone to beat her, which is why it was so important for your competitive nature to do exactly that. You’d challenged her before and lost, re-challenged her and lost, challenged her again believing the third time was the charm and lost.
But this time, this time you knew you would win. You were feeling lucky and you’d felt you’d learned all kinds of lessons in the previous matches, where she’d beaten you and taken your money every time.
Knowing just how much this meant to you, finding it cute, and honestly not minding a little extra pocket money (there was that gorgeous skirt she’d seen in one of the shops that she wouldn’t mind having), Raim readily agreed to the match.
Raim definitely doesn’t make the game easy on you. While not a very competitive person herself, just enjoying such things mostly for fun, Raim does have enough ego and pride to prevent her from taking it easy on anyone. If she’s going to do something, she’s going to do it to the best of her ability. She’s not going to just roll over and let you win – she is a teacher, after all, and no student learns by their teacher doing that.
So she uses her succubus skills and she teases you throughout the game, trying to shake you up, get you off your game. She flirts, tells you that if you wanted to see her naked so badly, all you ever needed to do was ask, plays footsy with you under the table, letting her foot trail up your thigh at one point until you almost jump out of your chair.
You’re doing every single thing you can think of, focusing so hard on the game, trying every trick you have learned to defeat her. You’d just about figured you were going to lose this one too though, just about abandoned hope, when you picked up just the card you needed.
You throw your hand down triumphantly, grinning ear to ear. You finally beat Raim and to say you’re thrilled is an understatement.
Raim takes it all in really good stride though. She’s honestly really happy for you because it’s obvious how much this meant to you. And the thought of stripping off all her clothes, of being naked, just really isn’t a bother to the succubus. She’d have zero issue with walking around naked all the time, if she was to tell the truth. It’s nothing to her.
She does have to give it her best try though. After stripping completely naked, making sure that there’s a little extra swing in her hips, that her tone is honied, oozing with provocation, she lays herself in your lap, congratulating you while asking if you’re quite sure you want the money from winning or if there’s not an alternate prize she can convince you to take…after all, that is her nail money for the week and she’s more upset about losing that than her clothes.
It takes every single ounce of determination in you because god damn, she is truly talented at what she does and god damn, do you want to take her up on that offer, but you reach behind her and take the money.
She holds a grudge more over that than anything else, but the grudge gets settled at the next game, where she makes sure to invite more of the teachers.
You’d been amusing yourself with a deck of cards one day when Robin stopped by your room. You’d asked him if he wanted to stay and play cards with you. Of course, he accepts happily. In Robin’s eyes, you’re the best of the best – you always find things to compliment him on, you seem to value his opinion and take him seriously as a teacher, you put up with his boundless enthusiasm and energy better than most do. He’s never turning down an opportunity to spend time with you. He’d have to be nuts to do that, is the only thing he can think.
It’s when you’re deciding what card game to play together that Robin shocks you. You make a joke off the top of your head about how the two of you could always play a round of strip poker, laughing to make it obvious that you’re just kidding around with him. Robin is instantly curious. The boy doesn’t seem to know at all what strip poker is. He admits to only having played regular poker once or twice and doesn’t get, at least at first, what strip poker is. How’s it different from regular poker?
You can’t do much other than just sit there, leaning back in your chair when he asks that. Your face is just slack, mouth a little open in disbelief and ‘huh?’ness. He asked such a stupid question, such an obvious question, so innocently and earnestly and you have to admit it was cute, though you really find yourself stuck as to how best to answer it.
You try to ‘no answer’ route, where you just sit back up towards the table, changing the conversation and hoping Robin will roll with that.
Eventually, just to get him to be quiet and to stop asking, you explain the nature of the game and all the rules. Robin’s eyes keep getting bigger and bigger as you explain everything and he’s determined and decided in the fact that the two of you are playing this game.
He does let you know, though, that if you feel too uncomfortable taking off you clothes after he wins, you can always chicken out at some point and he won’t hold it against you for doing so. Not one bit.
His little act of kindness wasn’t taken so well by you though. You got a little offended by his assumption that he’d win; it kicked your competitiveness up just a little bit.
Okay, a lot. As in, competitive enough to cheat the last couple hands. In your defense, Robin was killing that game, though he was claiming it was all down to beginner’s luck.
Some slight of hand though and you start catching up. Soon it’s not just you in your underwear and socks, but Robin too.
You’re careful not to arouse his suspicions. You let yourself lose your socks before you have a good hand, then your bra, before finally beating Robin, laying down the perfect hand for your last turn.
Robin takes it like a champ. He looks crestfallen at first, a little upset he hadn’t won, but he’s also a fantastic sport. He congratulates you on winning and tells you how good you did. He even asks if you’ll play with him some more sometime, teach him some tricks and tips so that he can beat you someday.
Once you promise to do so, you stare at him, waiting to see if he’d call chicken or not. He notices you staring, sees you watching him, and the moment just hovers there. He starts to blush and is red as a lobster by the time his hands go to the waistband of his boxers.
He’s careful about pulling them down. One of his hands slips under the waistband of the boxer and you realize, once he starts pulling them down with his free hand, it’s to cup his penis and testicles, to try to hide himself from you like a man would at the doctor’s.
It might have worked. It honestly probably would have worked…if he had been entirely soft. However, Robin’s sporting the start of a chubby, about at half-mast, and though he’s trying admirably, it’s just a little too much for his single hand to hide from your eyes.
For such a thin, tiny man, he was surprisingly endowed.
You have a real hard time keeping from staring until he calls you out on it.
Even when you think you have him licked, Robin seems to be able to turn the tables on you.
You’re not quite sure if you like that or not.
