[NSFW] Obey Me - fem!MC first time with Diavolo
m.list
TW: nsfw, first time sex, loss of virginity, swearing, Characters: Diavololo Writer: ahegato
Context: The MC would probably be pretty nervous since it’s the first time and stuff like that. Idk I lost my virginity when I was like 17 and now I’m really old, so I barely remember it. I just recall worrying about the pain while also knowing it was common, that’s about it lol
You/your pronouns, so basically gender neutral, bUT MC will have female bits.
lucifer (cumming soon) | mammon | leviathan | satan | asmodeus | beelzebub (cumming soon) | belphegor (cumming soon) | diavolo (ur here) | barbatos (cumming soon) | simeon (cumming soon) | solomon
DIAVOLO:
another big boi. bigger boi, in fact
naturally, he’s very worried that he’ll hurt you
and while Beelzebub which you don't know yet because I haven't finished writing it adksjfknsj felt better once you promised to speak up, it doesn’t quite ease up Diavolo’s concerns
what if you pretend to be fine to make him feel better? he doesn’t want that!
this man sits you down and literally makes you decide on a safeword because he’s so scared
“sweetie it’s only the first time”
“y-yes but what if-”
he’ll ask if you’re sure at least five times before he even takes his pants off
and then he says it a few more times afterwards for good measure
eventually you have to tell him to just shut the hell up, and that you’ll let him know if you change your mind
most of the foreplay time is spent on preparing you for his size
the slow increase from one finger to two and then three has you melting
diavolo is dead-focused on stretching you out as gently as possible, constantly looking up at your face to see if you’re okay
thankfully, every single time his gaze meets yours, you appear to be even more in bliss than before, and it does a lot to ease his worries
probably ends up making you finish before he’s even entered you because of how much he’s stimulating you
he asks you to go on top, because he doesn’t want to trap you underneath him if it gets too much
The moment his member is free from the restraints of his clothes, you understand why he was so concerned earlier. He’s absolutely massive.
Your eyes go blank as you slowly sink down onto his length. It feels like you’re going to be split in two, your insides are burning and tears threaten to spill from your eyes. Diavolo tries to voice his concern over your reaction, but you quickly hush him, telling him to shut up and that you’re trying to focus on relaxing. You move a hand down to rub your clit, giving you another feeling to focus on as you take deep breaths. It felt like there was no way you’d be able to handle it, but to your surprise, you slowly felt yourself adjusting to his size.
Diavolo didn’t move a single muscle underneath you, he barely dared to breathe. He tried to not let it show how good it felt, just in case the pain was too much and you had to stop it completely, the last thing he wanted was for you to try to sit (hah) through it just for him.
As if you read his mind, you spoke once more. “If I can’t handle it, I’ll stop.” and he finally has to trust your decision.
Finally, you’ve sunk all the way down, your hips meeting his, the both of you overwhelmed by the sensation.
It stings but fuck, it also feels so good, you can’t stop now.
You’re squeezing him so fucking tightly, he’s not sure if he’s ever felt this good before, and he can’t help the moans that slip out between his heavy breaths despite his attempts to stop them.
And even though he’s absolutely terrified of hurting you, he would be lying if he said the huge size difference wasn’t also turning him on even further. The fact that your much smaller body is taking on someone as large as him is incredibly hot to him, it makes him want to see how much you could actually handle. The thoughts make him bite down in his lip, trembling as he struggles to keep it all to himself. He doesn’t want to scare you.
But then you pipe up and say, “I feel so full…”
…making his eyelashes flutter as he groans, cock twitching inside you.
You roll your hips experimentally and his grip on you tightens.
As you notice the pain having receded, you start to move, setting a steady pace.
“You’re shaking, Dia.”
“It feels so good… my body wants to move…but I don’t want to hurt you…” he whispers slowly between heavy breaths, voice trembling.
“Go ahead. Move me. I promised I would tell you if it got too much, so move.” you coo softly, and it’s near impossible for him to refuse that voice.
He gives in, his hands on your waist as he gently starts to move you up and down. As you wrap your arms around him and rest your head on his shoulder, moaning his name against his ear, he gets egged on even further, speeding up his movements.
“Are…are you really okay?” he asks between pants, although not letting up.
When all you respond with are moans and whimpers of praise and his name, his worries dissipate, and he starts to really get into it — he lets himself fully enjoy it, endless groans slipping past his lips as he bounces you on his cock.
As he nears his limit, he buries his face in the crook of your neck, whispering, “Love, I’m about to cum… where should I…?”
If you want it inside, his hips will roughly stutter before increasing the pace. The way he hits your cervix at every thrust turns you into mush in his arms, and you find yourself not caring in the slightest that it hurts a little. His cock abuses that particular spot inside of you, forcing you to the edge at a hell of a speed, making you scream if he hasn’t already caught your lips with his own. As you clamp down on him tightly through your orgasm, you quickly send him hurtling towards his own release as a high pitched moan is forcibly torn from his throat.
If you want it outside, he’ll pull out and stroke himself until he releases all over your back or your torso. If you let him cum on your chest or on your crotch, he’ll let out a low groan as he holds onto you possessively.
You will be sore afterwards. It doesn’t matter how much you guys prepared beforehand, you’re gonna feel that tomorrow, buddy. Diavolo is of course very understanding, he’ll make sure you get meals brought to you as well as some school work so you don’t get too far behind. And if you’re staying at his castle, he’ll come by to snuggle with you whenever he can.
✦ 30/11/2023 (*hides in corner out of embarrassment*) - 31/08/2025 ✦ ahegato ✦













