#their attempts to sabotage u only bring you closer together 💕💕💕

[diodellet]

keep the dress on (simeon x gn!reader)

i saw @devilllain's art of simeon in a maid dress and got possessed. (GIVE EM LOTS OF LOVE FOR THEIR ART GO OVER TO THEIR BLOG NOW RIGHT NOW!!) fucc man, i just love...men in fem clothing... the range,,, the POWER iT JUS BRINGS ME TO MY KNEES 😩😩 content warnings under the cut: nothing? it's just pwp ++crossdressing, dominant reader+giving oral sex, flustered simeon, mild jealousy and possessiveness from the reader, implied jealousy from the sinblings, praise kink, mild maid and master kink word count: 2.2k words minors do not interact

"Holy shit." Your gaze first settles on the sleeves of his dress. Seeing him in sleeves—puffy ones at that—was something that made you pause, where were his bare shoulders—You take in the way the longer ends were folded up to his elbows. He seems to have foregone his usual choice of gloves, settling for a shorter pair that leaves half of his palms uncovered. The front of his dress is neatly pressed, pristinely buttoned up, ending in a long skirt that reached below his knees. Not a single crease or wrinkle can be found, save for the frilly ruffles that adorn the edges of his sleeves and the dress' collar. The dress is complemented with a white apron layered atop it, you bet that the straps are tied into a simple bow at his back. Lastly, for his footwear, he only wore a pair of black shoes with square heels.

Your eyes tear up to see—oh, he was also wearing mismatching legwear, a thigh-high stocking and a knee-length sock held in place with a garter strap. You want to feel a hand up his legs—Simeon's serene smile falling at your words. "Language!" he scolds you. The tone he uses is enough to snap you out of your stupor.

"I'm sorry! It just slipped out!" you protest. Your fingers tug at the collar of your shirt, suddenly feeling heat creep upwards along the sides of your neck.

He never really admonished your predilection for crass language, but seeing as how you were in the presence of Luke and Solomon, you swallow back the reflexive curse that threatened to accompany your apology. Instead, your other hand fidgets with the hem of your shirt. Itching for a way to dispel the jitters that settled into your veins.

"Simeon! I'm not a kid anymore!" Luke huffs.

You spare a furtive glance to Solomon and Simeon, the former giving you an empathetic look while the latter's frown deepened. Sure, Luke might've been hundreds of years old, but Simeon would've had your head if you acted anything less like a decent adult in front of the younger angel.

"No, it-it's really my fault." The heat spreads to the tips of your ears, more out of shame than embarrassment. "I shouldn't have said that bad word, sorry, I'm sorry—What's with the getup, by the way?" You make a feeble attempt to divert the conversation.

An attempt which Solomon gladly extends an olive branch towards. "He's going to be helping the student council with a costume café this afternoon, didn't they tell you about it?"

"I don't think so?" Your head tilts to the side in confusion. You would've heard about it by now, knowing how much Asmo or Levi freely talked about their daily life on social media.

"I bet Lucifer cursed his brothers from talking about it." Luke says, crossing his arms over his chest. The gesture does little to emphasize his anger, on a normal day you would have poked fun at his expression. But there's a grain of plausibility to his words that strikes up a flare of jealousy inside you.

"Hm, maybe." Solomon shrugs, before giving you a knowing look. "But I don't think that's the only reason he'd do so."

A strangled noise erupts from your throat, which you try to play off as a cough. "Don't-don't ask me, I only found out today!" You hold your hands out in front of you defensively. Your cheeks were burning. This entire situation was unfair. You were going to get back at Lucifer. And your other pacts for not telling you about this.

To you gratitude (and simultaneous dismay), Simeon cuts in to say, "Well, you're still free to drop by later. My shift isn't until two, and it'll end a quarter to three."

And with that, the Purgatory Hall residents walk away. The sound of Simeon's heels clicking against the pavement grows fainter and fainter. You are left alone with that maddening polite smile and your less-than-savory thoguhts.

Taking out your D.D.D., you send a message to Solomon and march off in the direction they went towards. And they didn't even bother to tell you where it was being held, the nerve!

[...]

The first thing you do is back him up against the wall of the supply closet, pulling him into a feverish-open mouthed kiss. The surprised moan that tears itself from his throat sends you spiraling further down your need. Your hand hikes up to cup the back of his neck, you drink in every hitched breath, every plaintive whine.

Which he earnestly reciprocates, kissing you back with just as much fervor. One of his hands searches for yours and interlaces your fingers together.

That one hour of waiting was torture. Watching him move from table table, greeting cafe goers with a bright smile and hearing his pleasant voice call them 'Master.' It was an hour of agony, made worse with being pestered by the the demon brothers to try at least one of everything on the menu, to take pictures of everyone—which of course!—turned into painstaking group photos that were more effort to coordinate than they were worth taking.

But that was in the past. You can afford to let your jealousy dissipate, just a little bit.

Pulling away, you ask, "where'd you get the dress?"

There's a string of saliva connecting your lips to his, and you catch the way his throat bobs as he gathers his words. "Leviathan lent it to me... th-the shoes are from Asmo..." You feel him tense up as your other hand slips under his skirt, feeling up the side of his thigh.

You let out a low whistle. Silk. That meant everything else—the gloves and stockings—was his. "I bet they had fun dressing you up, didn't they? Probably spent the whole day trying on dozens of outfits, huh?"

"...there were a few, yes. I thought you...would like this best..." That meant someone from your pacts let this—that you were into this kind of thing—slip.

You have a few guesses as to who that could have been. "Mm, you thought right—will you hold your skirt up?"

He obeys, gathering the layers of fabric and hiking them up. Dropping to your knees you press your palms against his thighs, feeling them tremble. They're not shaking from exertion, the type of heels he was wearing guaranteed more comfort than wearing stilettos. Even if he was on his feet for almost an hour, you are sure that you're the reason he was shaking with anticipation.

You hear him call your name. Flicking your gaze up to meet his, your fingertips are hooked into the waistband of his underwear, a few scant centimeters away from freeing his cock. "Levi said he—" The edge of your nail grazes against the sensitive skin, eliciting another shiver. "—h-he wanted this returned...intact..."

You roll your eyes, leave the unrealistic expectations to the third-born. "Okay," you reply.

A bunch of the skirt falls against your face, Simeon's hand finds your shoulder. "I'm serious—" he warns.

You don't let him finish that threat, you were the one in control right now. Knocking his hand away, you yank his underwear down and lick up his shaft. "What'd I say about the skirt, angel?" It's a small gesture, but you have him so wrapped around your finger that his hips reflexively cant up to chase the sensation of your tongue.

"Hah—I-I'm serious..." His authoritative tone weakens as your tongue catches a pearl of precum leaking from the tip.

"I know, I know, just keep your legs spread and stand still." His skirt is pulled away from your field of view, granting you the sight of his flustered form. "And no more touching."

His tongue darts out to wet his lips. Growing fluster and mild irritation are warring in his eyes, but in spite of all that going on in his mind, you can feel him growing harder in your palm. Feel his navel rising and falling in trepidation. "Okay, no touching." His fingers flex, bunching up and creasing the skirt's fabric even more.

"What else did I tell you?" You lean closer, trace circles along his inner thigh with your fingers. Letting the puff of your breath ghost along his cock.

"To-to keep my legs apart..." More precum leaks from the tip.

Your finger swipes at his arousal, dampening the pad of the digit. "Mhm, go on..."

"And to—" You pull away right when he jolts at the feeling of your slicked palm gliding up and down his dick. What you would give to hear that needy noise again. "—keep still..."

"Yep, that's right....good." Your voice lowers and you finally, finally take him into your mouth.

The moan that spills from Simeon is downright sinful, you feel his knees about to buckle from the welcome stimulation. His breathing is growing ragged, but he's got his mouth clamped shut to stifle any more accidental noises. Your own arousal is building between your legs, but your focus stays on servicing Simeon with your hands and tongue. You can feel a mix of spit and arousal running down your chin, but you're too far gone to care, too mesmerized at the sight of Simeon falling deeper and deeper into pleasure.

When your jaw starts to ache, your hand curls into a fist to stroke the heated flesh. Making sure to catch the sensitive underside of his dick, to tease the tip with the flat of your palm. Every involuntary shake and twitch, every soft whine from him fills you with a heady mix of arousal. You have to give him credit for listening to you in spite of his growing impatience. "You're doing so well for me, angel."

His voice wavers. "I'm... ngh... getting close..."

Relaxing your throat, you swallow his length. Your palms brace themselves against his inner thighs. The gesture elicits a loud whine from him. His cock hits the back of your throat, and you feel your throat seize up in momentary panic. More drool slips down your chin, spilling onto your shirt. A hand cards through your hair in an attempt to soothe you. You glance up at Simeon and his hand pulls away a moment too late—

Didn't I tell you not to touch me?

You set a punishing pace against him, hollowing your cheeks and sucking hard. Your ears are filled with a litany of praises and gratitude, mixed with the sounds of his moans pitching higher and higher as he draws closer to release. Your head is filled with the thump of your heartbeat in your ears, the squelch of your saliva as you fellate him. His hips rut into the heat of your mouth, meeting the bobs of your head. "Hah... Master, I-I'm going to—"

A surprised moan escapes you when you feel his cock twitch before spilling his seed down your throat. Your nails dig crescent marks into the skin of his thighs.

Still, you swallow. You did promise that he would get to return the dress intact.

You pull away from his softening cock to catch your breath. Simeon looks utterly debauched, and you're sure that you look just as mussed up.

A beat of silence passes.

"So...'Master,' huh?" His head turns away to avoid your inquisitive gaze. You can't help the laugh that escapes from you.

Simeon weakly protests, stammering, "it just... slipped out, I guess..."

That didn't sound like an accident. You wonder if he merely put on the maid act in preparation for this event or if there was something deeper—perhaps subconscious?—behind his use of the title.

"I'm gonna ask Levi to let you keep this dress—no, scratch that. I'm telling him you're keeping it." Taking out a handkerchief, you wipe at your mouth, at some of the mess along his thighs and groin. You savor the reflexive twitch from his oversensitive nerves and the way his hold on your wrist tightens for a mere fraction, before helping Simeon stand. When you think that he can keep himself upright, you busy yourself with smoothing out his dress.

"Huh, why?"

He shudders again as you retie the straps of his apron. Your hands splay against his lower back as you consider your next words.

"Because I want you to fuck me while wearing it."

He meets your bluntness with a moment of stunned silence and fragmented words. "O-oh, um...okay—" His response tapers off into a surprised moan as your fingers press an appreciative squeeze into his waist.

From your position, you're lower than him, bending down to help fix the underlayers of his skirt. So far it seems passable, but he probably has to double-check in front of a mirror, make sure that there's no trace of your illicit activities before his second shift. At least, on his person.

Straightening up, you guide him to look at you with the tips of your fingers resting on his chin. Your touch is gentle, but your tone of voice leaves no room for argument. "Once Lucifer's stupid fundraiser café thing ends, you better come to my room wearing this. Got that, angel?"

You hear him audibly swallow. "Yes." But he still holds your gaze.

"Yes, what?"

The words are uttered in a low voice, you have to strain to hear them. "Yes, Master." His cheeks heat up underneath your palm.

"Good." He isn't one of your pacts, but that made his willing subservience all the more precious.

FOR ONCE FOR ONCE I CAN FINALLY SLAP DOM!READER ON THIS AS A TAG AAAHHH i'm still weighing if i have the spoons to put together a continuation? if i do, im gonna say right now that it won't be posted any time soon. devilllain's art was just powerful enough to draw out 2k-ish words for this lmao dont be afraid to rb and holler in the tags! any comment, no matter how simple, is enough to make my day💕💕