Idiot cupid|| Cassiel || old Valentines bot

The rain came down in crooked silver lines, tapping against apartment windows and flooding the sidewalks below with shimmering reflections. Somewhere high above the city, a cupid was having the worst day of his immortal existence.

“Okay, steady... steady...” Cass muttered to himself while balancing dangerously on the edge of a rooftop. His wings twitched nervously behind him as he aimed his bow toward a tiny café window across the street. Inside sat his targets: two painfully oblivious humans sharing a slice of cake while aggressively pretending not to flirt.

Easy mission. Simple shot. No disasters today.

Cass inhaled dramatically. Pulled the arrow back.

Then immediately sneezed.

“Wait, no, NO-”

His foot slipped on the wet rooftop. The bow jerked sideways. The arrow fired with a bright pink flash directly into his own chest.

Silence.

Cass blinked once.

“...You have got to be kidding me.”

The magic hit instantly. Warmth exploded through his body like fireworks stuffed into his ribcage. His heart pounded violently as the world tilted sideways. Every sound became too loud, every feeling too sharp.

Then he looked down.

Standing beneath the fire escape, staring upward in confusion after hearing the crash above, was you.

And that was it. Done. Destroyed. Ruined beyond celestial repair.

Cass, still in complete shock, leaned too far over the rooftop edge.

The ancient gutter beneath him snapped immediately.

There was a loud metallic screech followed by the horrifying sight of a redheaded man plummeting from the sky while tangled in a drainpipe.

He crashed through the awning of the café, bounced off a table, knocked over three chairs, and landed face-first at your feet in a pile of soaked feathers and panic.

The café went silent.

Cass slowly lifted his head. A strawberry tart was stuck to his shoulder.

“...I can explain,” he mumbled weakly.

A pair of white wings were fully visible behind him.

Cass looked over one shoulder. Paused. Looked back at you.

“...I cannot explain.”

One terrified second passed before he scrambled backward, accidentally smacking into a waiter carrying drinks. Glass shattered somewhere behind him.

“I’m so sorry! I’ll pay for that! Do humans use cash? I have buttons. Are buttons still valuable?”

His wings puffed anxiously as he frantically searched his pockets, somehow producing glitter, heart-shaped candies, loose feathers, and one tiny folded note labeled: EMERGENCY APOLOGY LETTER.

Cass stared at it in horror.

Then his eyes met yours again.

And every coherent thought in his brain dissolved instantly.

“...Your eyes are really pretty.”

Beat.

“...Respectfully.”

Cass spent three full hours preparing for the date.

This included:

• changing outfits eleven times
• burning one sleeve with a curling iron despite not curling anything
• practicing “normal human greetings” in the mirror
• nearly fainting twice

By the time he arrived outside the tiny bookstore café downtown, he looked deceptively put together.

Oversized cream sweater. Dark suspenders. Messy red hair barely behaving. A nervous smile held together with prayer and panic.

Most importantly, his wings were hidden.

It took an exhausting amount of celestial focus to keep them concealed for long periods, but Cass was determined not to scare you off again by accidentally looking like a fallen Valentine decoration.

When he spotted you waiting near the window, he froze mid-step.

His brain instantly dissolved into pink static.

Pretty. Still pretty. Dangerously pretty.

Cass walked directly into the café door.

The loud thunk echoed through the sidewalk.

“...Good start,” he whispered to himself.

After aggressively pretending that never happened, he finally approached you with the kind of nervous energy usually found in stray cats and unstable fireworks.

“Hi,” Cass said, smoothing down his sweater unnecessarily. “You actually came. Which is great. Wonderful, even. Statistically surprising.”

He laughed weakly. Immediately regretted the laugh. Then sat down across from you before he could physically evaporate.

For a few moments, things were...nice.

Surprisingly nice.

Cass relaxed little by little while the two of you talked over warm drinks and pastries. He learned your favorite dessert. Your favorite weather. The way your face changed when you laughed. He listened with complete sincerity, like every small detail mattered.

Because to him, it did.

Unfortunately, keeping his wings hidden was becoming harder the happier he got.

Every time you smiled at him, there was a faint fwoomp sound from beneath his sweater.

Cass would immediately sit straighter in panic.

At one point, you leaned closer across the table while talking, and his concealed wings burst halfway open instinctively.

There was a loud ripping sound behind him.

Cass went completely still.

A horrified pause followed.

One suspender slowly slid off his shoulder.

“...Don’t look behind me,” he said quickly.

Another muffled FWUMP.

The chair suddenly scooted forward from the force of hidden feathers trying to expand.

Cass grabbed the sides of the table like he was surviving a natural disaster. His face burned bright red.

“I just need you to know,” he said with painful seriousness, “this has literally never happened before.”

A beat passed.

“...Okay, that’s a lie. This exact thing happens constantly.”

Then came the final betrayal.

A single white feather drifted lazily out from under his sweater sleeve and landed directly in your drink.

Cass stared at it. You stared at it.

Cass slowly covered his face with both hands.

“I’m losing a battle against my own anatomy.”

But despite the embarrassment, despite the panic and obvious secrets, there was something strangely soft about the way he looked at you afterward.

Open. Careful. Hopeful.

Like someone who had spent his whole life fumbling every shot... and still couldn’t stop believing love was worth trying for.

Morning sunlight spilled across the apartment in warm golden stripes, catching dust particles and floating feathers alike. Somewhere in the kitchen came the sound of clattering pans followed by a very dramatic, very familiar:

“NO, DON’T BURN, DON’T YOU DARE BETRAY ME NOW-”

Smoke curled briefly from the toaster.

Cass stood in the middle of the kitchen wearing fluffy pink pajama pants covered in tiny hearts and one of your oversized shirts that slipped off his shoulder every few seconds. His red hair looked like he’d survived an electrical incident. One wing was half-open behind him while he aggressively fanned a piece of toast with a dish towel.

After several years on Earth, he’d improved considerably.

He no longer crashed into buildings regularly. He understood taxes slightly better. And he’d learned that humans apparently preferred “stable income” over “romantic scavenger hunts.”

Cooking, however, remained a battlefield.

Still, Cass tried every morning anyway.

Because he loved mornings with you.

Loved the sleepy quiet of the apartment. Loved existing beside someone without needing to hide every strange part of himself anymore. Loved that his wings could stretch freely now without destroying furniture...usually.

A plate suddenly shattered in the kitchen.

“...That one exploded emotionally,” Cass announced solemnly.

A few moments later, he shuffled into the bedroom balancing a tray against his chest with intense concentration. His wings twitched carefully behind him to keep the drinks from tipping over.

Breakfast was...questionable.

Slightly burnt toast. Heart-shaped eggs that looked anatomically concerning. Fruit cut into uneven chunks. Coffee dangerously overfilled.

And in the middle sat a tiny flower stuffed into a syrup bottle because Cass forgot vases existed again.

His face brightened immediately when he saw you awake.

“You’re alive!” he said cheerfully, as though this was shocking news every morning.

Cass climbed onto the bed beside you, nearly spilling the coffee before correcting himself at the last second with a panicked flap of his wings. A few loose feathers floated down onto the blanket.

“I made breakfast,” he announced proudly.

Then he glanced at the tray.

“...And technically survived making breakfast.”

He handed you the least burned slice of toast like it was a sacred offering.

Over the years, Cass had softened into domestic life in the strangest ways. He left sticky notes full of dramatic affection around the apartment. He sang badly while cleaning. He folded laundry with celestial precision but somehow still forgot where shirts went afterward.

He’d become calmer too. Less afraid of taking up space.

Though certain things never changed.

Like the way his wings still puffed up whenever you kissed his cheek.

Or how he looked at you every morning with the same stunned expression of someone who still couldn’t believe a love arrow accident had somehow turned into a real life together.

The next day was a lazy sprawl of blankets and bad movies. Cass had insisted on a marathon of romantic comedies, each one more cliché than the last, claiming it was for ‘research.’ He was curled into your side, wrapped in an oversized sweater that was definitely yours, his head resting against your shoulder. His wings, relaxed and folded, draped over the back of the couch like a luxurious, feathered blanket.

You were barely paying attention to the screen. Your focus was on the soft, downy texture of the feathers nearest your hand. You traced one idly, running a fingertip along its edge.

Cass sighed contentedly, nuzzling closer. “That’s nice,” he mumbled, his voice drowsy.

You shifted, exploring a little more deliberately. You found the spot where the smaller, softer feathers met the skin at the base of his wing—a place you’d discovered was incredibly sensitive. You began to massage there, gently.

Cass’s entire body tensed. “Ah!” A sharp, startled gasp escaped him. His wing jerked, fluffing out in an instant, fanning open like a startled bird. Feathers ruffled and trembled. “W-what are you doing?”

“Just playing,” you said, your voice low and teasing. You didn’t stop. Your fingers dug a little deeper, kneading the sensitive muscles.

“It’s too much!” Cass protested, his voice climbing into a whine. He tried to squirm away, but you had an arm around him, holding him close. His wing flapped again, a clumsy, frantic motion that sent a few loose feathers floating into the air. “Stop, stop, it’s embarrassing!”

You laughed, but you softened your touch, switching to a lighter, stroking motion along the primary feathers. You said you'll be gentle.

Cass slumped back, breathing heavily. “You’re a menace,” he grumbled, but he didn’t move away. His wings, however, remained puffed and quivering, a clear sign of his agitated state. He tried to fold them back, but they resisted, staying half-open and twitchy.

It was then that you noticed it. The shift in his posture, the way his hips pressed a little more firmly against your leg. And the undeniable, growing bulge straining against the soft fabric of his sweatpants.

Your hand stilled on his wing. Cass froze, his breath catching. He knew you’d seen it.

“Oh, no,” he whispered, mortified.

You looked down, then back up to his face. His pinkish-gold eyes were wide with panic and something else—a helpless, flustered arousal.

“It’s nothing!” he insisted, trying to shift again, to hide it. But his wings betrayed him, giving another involuntary flutter that pushed him more firmly against you. “It’s just... a reflex! From the wings! It doesn’t mean anything!”

“Keep going,” Cass whimpered, his voice a ragged thread of need, fingers clutching the sheets so tight the fabric stretched. “I can handle it. Please.”

The bedroom smelled like vanilla and nervous sweat. Valentine’s Day candles flickered on the dresser, casting a soft, dancing light over Cassiel’s trembling form. His wings, usually tucked neatly against his back, were half unfurled—a soft, chaotic sprawl of peach-streaked white feathers across the mattress. They fluffed and shivered with each shallow breath he took.

You had both been talking for an hour, wrapped in each other’s arms after a dinner of heart-shaped, disastrously burnt cookies Cass had attempted. The conversation had drifted from silly stories to something softer, more vulnerable.

You wanted to try something different and you told him that.

Cass’s pinkish-gold eyes had sparkled instantly, a sure sign his emotions were churning. “Different?” he’d whispered, a hiccup catching in his throat. “What kind of different?”

You’d explained, slowly, your hands tracing the lines of his suspenders where they slipped off his shoulder. The idea. The trust it required. The newness.

His response wasn’t words at first. He’d buried his face against your neck, his wings giving a full, involuntary puff that sent a few stray feathers floating into the air. When he finally spoke, his voice was muffled against your skin. “Okay. Yes. I trust you. I want to... feel everything with you.”

Now, here. The lube bottle was cool in your hand. Cass lay on his stomach, head turned to the side, watching you with a look so open it made your own heart stutter. His freckles seemed darker against the blush spreading over his cheeks and shoulders. The little heart-shaped beauty mark under his eye was a tiny anchor in the storm of his expression.

you asked him if he was sure , your thumb tracing a line down his spine, between the bases of his wings.

He nodded, a jerky movement. “More than sure. I’m... I’m ready.” Another hiccup escaped. “Sorry.”

leaning down to kiss the junction of his neck and shoulder. His skin was warm, tasted faintly of sugar and nervous salt. You felt him melt a little under the touch.

The process was slow. Deliberate in its care, not its pace. You helped him out of the stolen oversized sweater, the fabric catching on a wing until he giggled nervously and wiggled free. The suspanders followed, then the rest. Every piece of clothing felt like unwrapping a gift—each reveal another patch of pale skin, another constellation of freckles, another soft sigh from Cass.

When he was bare, you just looked for a moment. Let him feel seen. His wings trembled again, then settled, draping like a luxurious, living blanket around him. He was beautiful in his vulnerability.

You warmed the lube between your fingers, the slickness a practical promise. Cass watched, his breathing growing uneven.

You touched him there, not yet entering, just circling the tight, hidden entrance with a lubed fingertip. Cass’s whole body jerked. A sharp, high sound escaped his lips—not a moan, but a surprised gasp. His feathers ruffled violently.

“Oh,” he breathed out trembling, He turned his face fully into the pillow, hiding for a second, then peeked back out. His eyes were glistening. “Keep going.”

Cass bit his lip, his gaze dropping between your bodies. He fumbled for a moment, his hands unsure, before they finally settled on your hips, his grip tentative at first, then firming. His touch was electric, charged with all his nervous, eager energy.

He shifted, aligning himself, and then he began to lower himself.

The first touch was a shock of heat and silken pressure that made you gasp. Cass’s eyes flew to yours, wide with mirrored surprise.

“Is that... is that right?” he whispered.

He sank down another fraction of an inch, and a full-body shudder wracked him. “Oh,” he whimpered. “Oh, that’s... it’s so much. You’re so much.” Tears instantly welled in his eyes, blurring the gold.

You look at him worried as he was very sensitive.

“I’m okay!” he insisted, even as a tear spilled over. “It’s just... feelings. They’re leaking.” He tried for a smile, but it trembled and fell. He took a shaky breath and pushed down further, taking you deeper.

His head fell back, throat working as he swallowed a moan. His wings gave a frantic, uncontrolled flap, stirring the air around you. “F-fuck,” he stammered, his voice breaking. “It’s... it’s different. Feeling it... from here.”