WHEEL SPIN CHALLENGE #2 | Cupid x Rupert

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"You mortal mortal creatures are such fascinating things..." Cupid commented, running his smooth hand down Rupert's chest, his free hand trailing to the restraints on the imp's wrists to make sure they weren't coming loose.

The smaller of the two shivered, letting out a shakey breath, squirming around a little before his hips were pinned down.

"Stop squirming," The demigod ordered in a low voice, retracting his hands. "I'll be able to tell if you do again."

"S-Sorry, sir~..." Rupert whimpered, obediently stilling.

"Good boy."

Cupid went back to what he was doing, running his hands across Rupert's skin, taking note of every little reaction. Everytime he'd touch a spot and see the other react positively, he'd do it again, and take notes of the spots he shouldn't touch. He hummed a little to himself, continuing with his torturous pace until he got to Rupert's upper-thighs. Cupid tilted his head and gently rubbed at the smaller's erection, cracking a small smile at how the imp bucked his hips up for more in response.

"Noted~..." Cupid said aloud, shifting a little to press his own thighs together as he felt a flutter in his lower stomach. How odd...

"C-Come on, man! Y-You're practically torturing me n-now!" Rupert whined out, squirming in desperation.

Cupid hummed a little. "Your reactions are... Quite fascinating~..." Rupert's face flushed, more than it already had been, at that. He looked away, gulping. "Adorable~..." The demigod commented quietly.

He shifted to kiss at the imp's neck, sucking dark marks into his flesh and biting down every so often. With his free hand that he hadn't been using to navigate Rupert's body, he wrapped his hand around the smaller's erection, slowly beginning to jerk him off, humming against his skin. He smirked when Rupert let out a moan, attempting to buck his hips upward.

"G-God, please! J-Just fuck me already! J-Just do s-something!" Rupert begged, squeezing his eyes shut. "P-Please, Cupid!""

The demigod hummed a little at that, pulling away and nodding a little. "Fine then~..." He slid his hands down to unbutton his jeans, his wings sliding off his shirt for him. He tugged his pants and underwear down a little to expose his erection, tilting his head when he sensed Rupert shuddering in response.

"Something wrong~?"

"N-No, it's just... K-Kind of big..."

"Is... Is that... Good..?"

"H-Hell yeah~..." He breathed.

Cupid's face flushed more than it naturally was, him grabbing Rupert's hip with one hand, using his other hand to guide himself to be lined up. He let out a shakey breath as he pushed into him, nails digging into the imp's skin a little. The smaller of the two let out a groan of pleasure and pain, a shiver running down his spine.

"F-Fuck~..." Rupert breathed, tugging at his restraints. "M-Move... P-Please~.."

Cupid smirked again, tightening his grip before thrusting into him, starting slow but rough, then beginning to speed up.

It was times like this that the demigod wished he could see. He would love to see what Rupert's facial expression was... Then again, he did have the sounds of the imp's moans and he could sense the other trembling ever so slightly from the pleasure. That was enough for him.

He continued like this for a while, before feeling Rupert start to shake harder and mosn a little louder.

"C-Cupid! I-I'm gonna-" Rupert gasped out, before his eyes widened when Cupid completely stopped. "W-Wait! F-Fuck- No!" He whined out desperately, moving his hips to try and fuck himself on Cupid's length again, but to no avail.

"Hm~?" Cupid tilted his head a little in curiosity. "You're going to what?"

"C-Cum! I-I'm gonna cum! P-Please let me~!" The imp practically begged, back arching a little.

"Fine, fine... Calm down~..." He let out a chuckle, starting to roughly thrust into him again, relishing in the high-pitched moan the other let out in response.

After a few seconds, Rupert gasped out and arched his back, climaxing and releasing onto Cupid's stomach. The demigod raised his eyebrows in surprise and confusion, halting his thrusts for a second, reaching down to gently touch at the sticky substance and delicately sucking some off his fingers.

He let out a small hum before going back to thrusting into Rupert, eventually climaxing inside of the imp, his wings puffing up a little a shuddering as he did. He then pulled away, tilting his head to the side.

"That was... Interesting... Do you suppose you wouldn't be opposed to doing this again sometime?" Cupid tilted his head to the side as he asked.

"M-Mngh... I-I'd love to~..."

...

"RUPERT YOU LITTLE BITCH WHERE'S MY-"

Cupid quickly covered Rupert with one of his large wings, looking over to lock eyes with the intruder.

"Uuhhhhhh-" Lucifer glanced in between them, before doing finger guns as he went to back out of the room. "You know what? I'll just come back later-"

He then closed the door.

"Good riddance." Cupid commented.


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