“No, I’m totally over him,” you say firmly, wishing just one of the brothers would believe you. “I mean, we didn’t talk at all over break, and I saw in Devilgram he got a back to school haircut. Everyone knows crushes don’t stay, especially after there’s been a haircut.”
“That is true,” Mammon nods.
“Well, not for me, of course,” Asmo sighs, putting his chin on his hands. “That just seems to make me more popular.”
“Well, this isn’t about you,” you say. “It’s about me! A me who is completely and totally over—“
“Over who?” Asks Simeon, sliding between you and Satan, all long-legged and sun-striped in the human realm’s sun. His haircut, you realize with a slow sinking horror as your cheeks start to heat, looks nice.
Belphie takes one look at your face and begins to snicker, hiding his face in Beel’s shoulder.
“I didn’t know you liked someone,” Simeon continues, looking at you earnestly. His deep brown eyes sparkle and he leans towards you, too close. You manage a nervous chuckle.
“Yeah, liked,” Mammon replies, emphasizing the past tense. “MC here really insists those feelings no longer remain.”
“Well that’s a shame for the lucky guy,” Simeon comments, and you can’t breathe for a moment.
“Ah, uh,” you say intelligently.
He chuckles. “Oh man, I missed you over the summer. We definitely should catch up. Maybe grab a bite to eat after classes.”
“T-together?”
“Hopefully together,” Simeon teases. “So, what do you say?”
The boys all share amused looks at your silence before Lucifer, of all of them, speaks up.
“MC agrees,” he says mildly, and Simeon beams.
“Great,” he says, standing. “I’ll catch you after school. My treat.”
As he lopes off, sending a fluttering wave to you over his shoulder, Mammon raises his eyebrows at you.
“Completely and totally over him?”
“I may have…regressed.”
leviathans-watching’s work - please do not copy, repost, or claim as your own
"love you, love you love you," simeon presses his head against your chest while you drive your hips to meet his, filling him up so well, "need- kiss, kiss me, please," he whimpers
"aw, my pretty boy can't cum without a kiss?" you tease. you know that that's the case. a kiss is like permission for him to cum, and he wouldn't dare do so without that permission. he sobs, tears brimming in his eyes as he nods.
he can hardly bring himself to speak with the amount of hot pleasure rushing through him, trying to escape the cage of his body. for someone with so little experience, you're surprised with how much control he has over his body. he babbles some nonsense, not able to grab onto the words he wants to say.
"sweet thing," you hum, continuing to rut into him. "you know how to ask."
"please!" he yelps, "need you- kiss- need to cum, wanna- ple-he-ease!" his voice is hardly anything more than a sob. his nails scratch down your shoulder blades.
finally, finally you smother his lips with your own. he's so lax, and he's covered in his own drool, he can hardly kiss back but he moans when you force your tongue into his mouth. he cries out thanks around you, under you, as he's finally allowed to cum, writhing and bucking and fucking himself harder onto your length. thick, creamy cum spills across his dark skin, cock spurting in time with his squeezing around you.
only when he's done do you pull back and look down at his debauched form. messy, covered in his own cum, hole stretched around you and drool trailing down his chin. he's your angel, and he looks the part even like this.
Head empty only thinking of Solomon eating you out...
He's got you push up on a desk, skirt pushed up to your tummy, your thighs around his head, resting on his cheeks. You're well aware anyone could walk by and see you two, but you're so, so horny for this, after putting up with Solomon's teasing all day, you don't even care if Lucifer saw the two of you.
He's messy. He drinks you and your wetness like it's the best thing he's ever tasted in all three Realms combined. His hands are gripping your thighs, almost desperately, keeping you closed and clenched around his head, bruises blossoming underneath pale fingertips. His tongue is absolutely a gift from someone, you can't tell if it's from Heaven or Hell, because the way it swirls around your clit is both euphoric and tantalizing.
The way he licks you, updown updown updown on your clit, teasing the sides of your labia, down to your hole, where he licks around it until you're begging him to just put it in, you need to feel his tongue in you...!
Your hands grip his white locks, nails running through his hair lovingly, and pulling not so lovingly when he teases your pussy too much and you tense up, clutching at his hair like it's your lifeline back to reality. The way he keeps flitting his eyes between meeting yours and watching your pussy get wetter and wetter makes you feel hot, a heat that intensifies when he presses his face harder against your cunt, like he's hungry for it, hungry for your sweet cum.
He drinks it. All of it. Licks it off you like a cat with cream.
And then he pulls back after you cum with that frusterating smirk you want to wipe off his face by riding him until he forgets how to make that expression.
"So," he says, a little too joyfully, "how'd I do?"
just under five weeks remaining! as a reminder, this event is open to all types of content: fics, art, moodboards, amvs, etc.! i so look forward to seeing what types of content is inspired and also highly encourage attempts to get out of your comfort zone and create something new!
again, here is the general info + link to prompts!
The Obey Me! Undateables + Making A Sex Tape Headcanons
Pairing: The Obey Me Undateables (MINUS LUKE) x Female! Main Character
Content Warning: NSFW (minors do NOT interact), sex tapes/filming yourselves having sex, oral sex (female and male receiving), vaginal sex, dirty talk, semi-public sex, third person, etc.
Word count: 1.1k+
Authors Note: Thank you for the request, anon! I didn’t quite pull out all the stops for the undateables as I did with the demon brothers, because I am 10000000% biased towards the brothers - but I hope you all enjoy it nonetheless!
Also, since this has gained quite some traction on both here and AO3, would anybody be interested in one shots of each individual making a sex tape with MC? Let me know if it’s something y’all would be interested in!
The Obey Me! Demon Brother’s + Making A Sex Tape Headcanons
Lord Diavolo:
Okay, let’s be real. For being the future King of the Devildom and ruler of all the demons, Lord Diavolo is a pretty cheerful demon who will do whatever the hell he wants just because it looks fun. Also, who exactly is going to scold him if anyone were to find out that he had made a sex tape with his star human exchange student? He wouldn’t care one way or another.
He would respond so cheerfully to you asking him too, as he usually does to anything that sounds pleasing to him.
“You want to make a sex tape, darling? Of course! Anything to please you, my dear. Come with me - we’re doing this right now, princess.”
So, where do you want to do it? Did you want to get railed in his larger-than-life office against the biggest desk in all of the Devildom with your phone propped up against a pile of paperwork? Did you want to get fucked against every golden wall in the Demon Lord’s Castle by a video camera? How about a video camera directed on the Lord’s king-sized bed while you ride his cock?
He would show absolutely no mercy on you, either - and the sex tape would be proof of that. Just because the Lord of the Devildom just so happens to be a happy and cheerful demon doesn’t mean that he doesn’t know what he’s doing in the bedroom, and while you’re cumming all over his face and dick, he’s got all your screaming and crying on video to hear whenever the hell he wants.
“Euh! That’s it, princess, cum all over my cock - just like that. I’m gonna breed you so full of my cum for the camera - just like you asked.”
Also… don’t you dare think about Lord Diavolo asking Barbatos to film it for all those filthy close-up shots of you swallowing his cum or taking his cock like the good girl you are. Lord Diavolo would at least ask Barbatos, at the very least.
Barbatos:
I mean… any wish is your command, right? I can’t see him actively wanting to make a sex tape with you, but he also wouldn’t see the harm in it either. Like, yeah… something new the two of you can do in the bedroom. Sounds good to him!
“Oh? Do you want to film this, my love? Very well, anything for you then - hand me your phone and I’ll take care of the rest, my dear.”
Any sex tape with Barbatos would be so soft and loving - like perfect, aesthetic porn. Despite being an all-powerful demon, I genuinely don’t think that he has a rough bone in his body when it comes to his lover. That’s not to say he doesn’t know how to make you cum all nice and pretty for the camera, however.
He would make it such a nice experience for you, too. Like candles all over the room, and soft music playing, while needy hands run up and down your sides while you sit pretty on his lap and ride him like it’s the whole reason you’re in the Devildom.
“Yes, sweetheart - so good for me. So pretty for the camera. Now lay down and let me be at your service, my dear.”
A sex tape with him would be so sweet - 10/10 recommend asking him to make one with you.
Simeon:
Simeon would most likely be the most against making a sex tape out of all of the brothers and undateables. Simeon has strict morals and is a literal angel of the Lord, so I feel like filming the two of you having sex just wouldn’t be a thing for him. However, since it wouldn’t be very fun to write about how much Simeon wouldn’t make a sex tape with you - let’s say he’s totally down to make one with you.
So, let’s paint a setting here - Simeon finally got to see you again after you both departed back to the human world and the Celestial Realm respectively. His time with you is so limited, and you both can’t wait to be in each other’s arms again - so why not film it so the two of you can look back on it again when you’re missing each other? You recommended a sex tape to mark your little reunion.
Just like Barbatos, I think that any sex tape with Simeon would be sweet and loving. I can’t imagine that an angel of the Lord would ravage you as Lord Diavolo would - but Simeon knows exactly how to make you cum like the good little angel you are.
“Yes, my Y/N - show me how much you missed me. Cum with me - let’s do this together, my love!”
Simeon would also be someone to go out of his way to make this a memorable experience with you - you two would film your sex tape after a nice date with wine, a nice hotel with the prettiest view, and he’d be bringing you to orgasm so hard that you wouldn’t even need a sex tape to remember the night.
Solomon:
Oh, he would be SO down to make a sex tape with you - I mean, what better way is there to prove that out of all the demons and angels and humans in all three realms pining over you, that you chose him?
Solomon is overall a pretty confident and powerful human - he’s going to make you irrevocably his all over video. You can’t convince me that Solomon isn’t a little bit of a freak, and I feel like he would be no different in bed.
Picture this - it’s the end of the day at RAD, and the two of you are about to leave the classroom, the two of you being the last ones to leave. As you’re trying to leave, you can’t get the door open, and it doesn’t take you very long to figure out that Solomon used magic to keep anyone from entering or leaving - long enough to fuck you on a school desk with his phone propped up on the teacher’s desk.
With your arms wrapped around his waist as he fucks you hard into the desk, kissing you to stifle your loud moans - you hardly have time to consider the repercussions if Lucifer found out.
“Shh, be quiet for me, Y/N. You wouldn’t want to get caught and have me stop, would you? Ugh, that’s it - take my cock, baby!”
Solomon would make multiple sex tapes with you, too. It would become a thing between the two of you - each one being filthier than the last.
