Chapter Text
A general sense of spookiness has descended upon you, your mind filled with the thoughts of ghosts and ghouls. Alongside these are the usual suspects of pumpkins and costumes, a telltale sign of a certain holiday. Halloween.
The only question is, how to spend it?
Ah, you're fairly certain you know of someone more than willing to dress up for the occasion. A little something more, too, you suspect...
- - -
The day has finally come to a close, and you feel nothing but relief as you let yourself inside your home. Relief that quickly fades as you hear you effeminate partner.
“Master!” Astolfo dutifully calls, his footsteps growing louder and louder, before he comes to a stop before you. To say he steals your breath away is an understatement.
There he stands, his usual, slender frame on full display. Literally. He wears nothing but a tight, red pair of panties. Well, and a red cloak. One that's wide open. The carefree smile he shoots your way tells you he has no idea what it's doing to you.
Ah, until her arches his back and throws up peace signs, even going as far as sticking out his tongue.
He knows exactly what he's doing. By the swelling bulge in his panties, it's affecting him damn-near as much.
“Like my outfit? I got it special for Halloween!”
“Did you?” you ask, shuffling in place in a pointless attempt at hiding your arousal. “I doubt they sold that just anywhere.”
He sniggers, standing straight as his eyes fall to your crotch. “I might not have put it all on.”
Ignoring the obvious, you push on. “So, who are you meant to be?”
“Can't you tell?”
Someone known for wearing red, but it doesn't narrow it down all the much. “Uh, not really.”
His pout is almost painful with how adorable it is, never mind the bratty stomp of his foot. “Red Riding Hood, Master!”
Oh. In hindsight, that should have been obvious. “Perhaps if you had a picnic basket, I would have got it,” you playfully tease.
Just like that, he perks up. His usual, cheery self again. “No need for that,” he points out, proudly striding towards you. He so easily draws a gasp from you, grabbing your crotch as he does. Sensual, at first, squeezing just a little as he fondles you. “I've decided I want something meatier to eat.”
“A little cum-starved, are we?”
“You've been so busy lately,” he admits, looking up at you with puppy-dog eyes. “Not too tired for me this time, right?”
“Astolfo, you only had to-”
“Good enough for me,” he cuts you off, all too happily dropping to his knees.
What can you do? Nothing but watch as he fishes your cock free of its confines. Hard and ready, his eyes light up as he strokes you. One, two and three, teasing tugs. His lips close in, planting a cute, loving kiss against the tip.
“Tastes so good,” he practically purrs, free hand reaching between his legs.
Before you know it, he frees his cock, stroking himself in time with you. Slow, loving strokes grow faster, becoming almost rapid pumps. Pre leaks freely from you, humming in delight as you surrender to his grip.
A moan comes freely as he licks you, playfully spinning his tongue around your tip. Like a hungry whore, he laps up your pre, replacing it with spit. Parting his lips, he dives deep, taking half your length with ease. Masterful tongue work swirls around your girth, massaging every inch he can. Then, without warning, he pulls free.
He looks up at you with such loving eyes, taking several deep breaths. “How long do you think you can last, Master?”
“Depends on how deep you go,” you answer, almost honestly. Truth be told, you have no interest in holding out, wanting to see him choke on your cum as much as he wants to taste it.
Astolfo answers with a wink, stroking his cock slowly as he inches forward. A loud gulp fills the air as he takes you in his mouth, tongue pressing against the underside all the way. Hints of a gag are barely suppressed as you reach his throat, sucking hard on you as his own strokes grow rapid.
Seconds pass by in bliss, the deep breath from his nostrils music to your ears as he pulls back. A few playful licks of your tip are all he offers; before diving back down! Burying his nose against your crotch, he bobs his head just a little, teasing your tip with his throat.
“Astolfo,” you manage through a moan, grabbing him by his hair.
He knows exactly what's coming, not fighting as you hold him in place. Your balls tighten as a torrent of cum blasts from you. Subtle thrusts of your hips have him choking, desperately swallowing as more and more of your seed pumps down his wanting throat. Despite the almost panicked gags, he manages to tough it out, breathing deep the moment he's released and free from your cock.
Sticky with cum and spit, you twitch at the sight and sound of his gasps for air. Yet, with a smile ever present on his face and still rapid strokes of his cock, you know damn well he enjoyed it.
“Good boy,” you praise, ruffling his hair.
It takes a moment for his words to return, breathing back to normal as he slows his stroking, barely teasing himself. “Not good,” he says.
“No?”
He shakes his head. “I stole something from the Big Bad Wolf.” As he speaks, he leans in close, almost as if speaking to your cock. “I think he wants to punish me.”
It doesn't take much for you to cotton on to his meaning, forcing him to look you in the eye with your finger suddenly beneath his chin. “Yeah? How would he do that?”
Almost whining, Astolfo gets to his feet. “Making Riding Hood his bitch!”
Your hands immediately dart to his hips, a squeak filling the air as you lift him off the floor. He's not all that heavy, and you bring him to the sofa. Not a word is spoken, only gasps for breath and slutty wails as you put him on the floor. His soft skin has your cock twitching with desire as you turn him around, making a show of forcing him to bend over. Something he does all too willingly.
“P-please,” Astolfo whines, all the while wiggling his behind. “I'll give it back!”
Taking your sticky cock in hand, you give yourself a stroke. With the other, you spread his cheeks. “I don't want it back,” you answer with a slightly gruffer voice, doing your best to stay in character. “I'm going to take it out of your ass.”
“N-no!”
His mock protests fall on deaf ears as you bring your cock to his ring. A gasp and grunt echo through your ears as you force yourself inside! Hot and tight, his insides practically fight to keep you out. Not that you let him, driving forward with all your might until you're balls deep!
“M-my innocence!” Astolfo cries between moans, walls so very tight around your invading cock.
“Mine,” you growl, leaning into him, fingers digging into his hips as your grip tightens.
Any pretence quickly fades. “F-fuck me, Master.”
Gladly.
Pulling back your hips, his grip on you damn near keeps you in place. You're strong enough to relish his tight hold on you, his cock and balls bouncing as you fill him anew! Swimming in pleasure, you relish each of his lewd wails, a constant chorus of absolute ecstasy as you take him time and time again.
Somehow, his insides squeeze all the tighter around, suddenly flexing again and again. Pure bliss surrounds his wails of delight, hot, mighty spurts firing from his cock as he shoots his cum harmlessly on the floor. His legs lose most of their strength, as you suddenly hold him up as you pound away, his climax only fuelling the fires of your pleasure.
Spent as he is, he endures with meek moans and needy whines. You don't stop fucking his tight hole until you crest that same summit, pushing his face into the sofa with a final, mighty heave with your hips! A cool, calming wave of pure carnal euphoria washes over you, mighty loads pumping straight into his ravaged hole. You hold him in place until you fill him with your final dregs, slipping out of him without fanfare as that familiar haze descends.
“Debt repaid, little red bitch,” you declare as he turns around, eyes closed as he stills swims in the remnants of his climax. You can't help yourself, bringing your spent cock to his face and wiping the remnants of your seed on his cheeks.
“N-no fair, master,” he complains with a pout, only to laugh.
“Very fair, look how much of a mess you made.” As if emphasising your point, you give his cock a playful stroke, earning a whine in protest.
“S-should use me like this more...”
Getting on top of him, you let your spent cock rest against his as he squirms. “Anytime, Astolfo,” you promise, rocking your hips as you grind your cock against his. “Or do you prefer Little Red Riding Bitch?”
Astolfo shivers, moving with your slight grind and cementing his new role. Should he ever choose to don it again...