Work Header

Let's Try It: Stinging Pleasure

Work Text:

“Michael! Angel, where are you?”

Y/n threw his keys into the bowl besides the door, and placed his coat in the closet.


He was sure the angel would be home. 

Michael told him he had some sort of a surprise for him, after y/n had been away for a few weeks with the Winchesters again.

He walked up the stairs, figuring that was basically the only place Michael would be, seeing as that was where he was usually stayed in the house.

As soon as y/n entered the room, the world spun, and suddenly, he found himself looking up at the ceiling.

Attempting to move, he was pulled back to the bed, the ropes that were keeping him held down chafing his wrists.

“M-Michael?” y/n stuttered, getting slightly worried now.

Just as his mind began racing through the worst situations, his angel showed up, poofing in, right on top of him, naked, his cock hard.

“Told you I had a present!”

Y/n began objecting, claiming he never indicated he wanted to do this. 

Well-not today, anyway.

“I never said it was a present for you, did I?”

Y/n groaned.

He wasn’t the biggest fan of bondage and being tied down.

Sure, it was nice to have Michael fuck him hard.

But he hated the fact that he couldn’t get his hands on the angel’s perfect body, or hair. 

There was nothing for him to grip onto as Michael made him cum.

“Michael? Do we have to?”

The angel stood up, looking down at y/n and snapping his fingers, the ropes disappearing.

“If you don’t want to, of course we don’t have to”, he answered sincerely.

Y/n saw the tiny amount of disappointment in the angel’s eyes, and decided he’d do it.

Michael deserved a treat after not seeing each other for a while.

“Never mind. Just-don’t tease me too much. I hate when you do that”.

Michael nodded, smiling widely and snapping his fingers once again, y/n tied up and naked this time.

“You shouldn’t have agreed to that, baby!”

The angel turned, walking into their huge walk in closet and coming back out, a whip and flogger in his hand.

Y/n’s cock hardened instantly.

He was a slut for being punished.

Especially the way Michael would do it.

“Knew you’d like this. Knew you want me to mark you. Make your skin tingle with pain. You love it, don’t you?”

Y/n nodded, his throat dry, anticipating the pain and pleasure that he knew he was about to experience.

“Good. Now, I don’t want to hear a single sound from you. Is that understood?”

Y/n moved his head, barely even nodding, too desperate for Michael to make him feel the stinging burn of the whip and flogger.

Michael sniggered, walking towards the bed, his own cock red and straining, the precum beading at the slit.


Even before y/n had a chance to nod, Michael brought the whip down, across y/n’s stomach, y/n clenching his entire body, gripping hard onto the ropes as he attempted to remain silent.

“Good. You’re doing well. Get ready for more!”

He brought the whip down fast and hard, cracking in the air as he targeted the same strip as he did the first time, over and over, until he heard y/n let out a little whimper, tears in his eyes, the line red and heated.

“Did I just hear something?”

Y/n shook his head frantically, not wanting this to stop anytime soon.

“Thought so”.

Michael switched to the flogger, bunching the strands in his hand and pulling them, making sure they were strong and sturdy.


He climbed onto the bed, kneeling in between y/n’s spread legs and ran the flogger down y/n’s chest, running over the long red pelt that formed from the whip, y/n twitching slightly at the touch.

He continued running it down y/n’s body, until he got to his cock, swirling the flogger, making the strands of leather tickle y/n’s cock and balls.

Y/n smiled at the sensation, closing his eyes, but quickly jumped up when Michael smacked his groin with the flogger, stinging his balls especially.

“Don’t get too comfortable, baby. You’re not gonna be able to sit for a while, after I’m done with you”.

He snapped his fingers again, y/n turning, and now on all fours, his ass in the air, still tied to the bed.

Michael kissed y/n’s asshole, sticking his tongue in for a second, before pulling back.

He raised the flogger and brought it down across y/n’s left ass cheek, instantly turning it red.

Y/n bit his lip, piercing his skin as he tasted his metallic blood, making sure he wouldn’t make a sound.

Michael continued his mission, needing to see both of y/n’s ass cheeks completely red and stung.

It didn’t take too long, the leather strands leaving behind their rectangular imprints, covering y/n’s ass.

He lowered the flogger a little, and hit y/n’s ball sack, y/n letting out a loud moan.

“Shouldn’t have done that, baby!”

Y/n bucked up, jumping slightly when he felt Michael flog his balls again, his grace entering his ass, and stroking his cock, all at the same time.

He turned his head, pleading to Michael with his eyes to make this quick.

But the angel just shook his head, grinning darkly at him.

His grace twisted around y/n’s cock, pumping it slow and hard, gripping it tight, all while pumping in and out of y/n’s ass, pressing against y/n’s prostate, stroking and massaging it, y/n’s cock shining with precum.

Michael watched as y/n squirmed beneath him, trying to thrust into the grace, and also push back, so it went deeper inside him, failing at his attempts.

Michael swelled up the grace inside y/n’s ass, watching as the hole bulged slightly and stretched, loving the way it puckered around the invisible force.

Michael switched up his actions, his grace now holding the flogger and whipping y/n’s back, as he settled behind y/n, his fingers entering his asshole, rubbing at his prostate, his grace still stroking y/n’s cock.

“Yea, baby. I feel you getting tighter. You’re close, right? Gonna cum soon? Cum all over the bed? Suck my fingers further into your tight asshole?”

Y/n nodded, his head landing on the pillow, his nails digging into the ropes that were still holding him, arching his back every few seconds as the leather hit his sweaty skin.

“Quickly, baby! Cum for me, y/n. Cum hard. Make my fingers completely disappear”.

Michael rubbed faster on y/n’s prostate, his grace disappearing, not able to focus on controlling it, when he was solely trying to get y/n to cum right now.

Y/n began moaning, not caring about the burning on his back, stomach, ass and balls.

All he could think about was the way Michael was pressing down on his prostate, rubbing at it fast, and building up the pressure, until he couldn’t take it anymore.

His cock released his milky fluids, stringing down onto the bedsheets and leaving a wet patch.

Michael didn’t stop until he was sure y/n was finished, all his cum milked out of his cock.

“Good job, baby. Now, time for me to cum inside you!”

Y/n groaned when Michael sunk into him, his cock stretching his walls.

He was in for a lot more pleasure tonight.