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It is fortunate for Astarion that for all of his intelligence and cunning, Gale Dekarios, multiple PhD holder and CEO of Waterdeep Holdings, prefers to secure his office through a traditional lock and key. It makes breaking into the man's office after hours much easier. Although, he did make a note to drop a tidbit about increasing security to the man– it had been laughably easy to gain entry to the building.
The door shuts behind him, the lock engaging with a click . He turns to survey the room, locating a bookshelf to slide the video camera on in the shadows, making sure that the red glow of the camera is not too obvious from the desk. Satisfied, he plops down on the large executive chair. He shudders as the movement jostles the plug in his ass, making him gush a little onto the leather surface. Mr. Dekarios keeps his office tidy, which Astarion knows is for show, if his home office is anything to go by. Briefly, he considers rifling through the desk drawers, but knows that the toy would keep him from returning everything the way he found it. Cazador will be disappointed, but his adoptive father can shove it.
He props his legs up on the mahogany desk, pulling his cell phone out to try to pass the time with Candy Crush. The messages from Cazador go unanswered, although Astarion does read through them. The last one is a warning that Mr. Dekarios has left whatever fancy awards ceremony the Counting House was hosting.
Anticipation curls in Astarion’s belly, a low heat that builds to a raging inferno. Mr. Dekarios is not a bad-looking man, certainly not the worst target that Cazador has sent Astarion to seduce. With a low groan, he rocks back onto the seat, catching the base of the plug and shifting it within him. He can feel it hitting his G-spot through the thin wall between his ass and pussy, sparks of pleasure shooting up his spine. His hips continue to gyrate, faster and faster, soaking the surface that results in him sliding a little too far forward and crashing onto the floor.
It’s unfortunate timing that the door opens at that moment. From Astarion’s spot on the ground, whoever just entered cannot see him and for that, he is thankful.
“Who’s there?” Astarion recognizes the deep voice as that of Mr. Dekarios, the man of the hour.
He draws himself up, dusting himself off to lock eyes with his target. “Good evening, Mr. Dekarios,” he purrs out, hoisting himself to perch up onto the desk, turning to look at Gale over his shoulder.
Gale’s eyebrows furrow in confusion. “You are… Cazador’s son?”
“I do love a man with a big brain. You know what they say about that, don’t you…?”
“I don’t understand. Why are you in my office at…” Gale checks the watch on his wrist, which Astarion can see is some horribly overpriced hideous junk. “9 PM on a Friday night?”
Astarion has to suppress an eyeroll. Why else would a hot piece of nineteen year old ass like himself be in a place like this dressed in a mini-skirt and a crop top? It’s every man’s wet dream come to life, is it not? “I heard you received an award… and wanted to deliver my congratulations… personally.”
He hops down from the desk, taking a moment to admire the wet spot he left, before trailing his fingers through it and approaching Gale, who looks thoroughly spooked. “I’m ah… not sure this is entirely appropriate, Mr. Szarr.”
“Ancunin,” Astarion replies, harsher than intended and mentally curses the slip up. “My name is Astarion Ancunin. But you can call me Astarion, darling.” Coming to a stop a few feet from Gale, he notices that they are roughly the same height, although where Astarion is slender, Gale is broader with both muscle and fat. It is not a bad look on him, not when whoever tailored his dinner jacket was clearly a professional.
He brings his fingers up to his mouth and licks them clean, the tang of his own pussy sitting heavy on his tongue. The choked gasp that action elicits makes a smirk spread across Astarion’s face. “Mr. Ancunin,” Gale says in a strangled voice. “I'm going to have to ask you to leave.”
So, a man who thinks he has morals. Astarion does love to break them. “But Mr. Dekarios, I came all this way. Surely you wouldn't turn me away without at least trying a taste?” Another step, bringing him within arms reach. He raises a hand to run it teasingly down the front of a pristine button-up shirt. “After all, I’m positively soaked for you,” he murmurs, dancing his fingers down the front of Gale’s pants, where there is a sizeable bulge that makes Astarion’s mouth water.
All of the business meetings, all of the subtle flirting, the innocent and shy act that he put on around Gale whenever he manufactured a reason to talk– he is not blind to Mr. Dekarios’ interest in him. And it is all paying off now, as he finds himself yanked in, searing lips closing over his. Fuck , the old man is a better kisser than Astarion thought he would be.
“You’ve been doing it intentionally, haven’t you?” Gale growls when he draws back, the normally kind brown eyes dark with lust and desire. “Driving me absolutely insane for the last few months, you little minx.”
Astarion laughs, the sound fake and slightly hysterical to his own ears. “You are a very attractive man, Mr. Dekarios,” he compliments, deftly undoing a button with one hand. “And I do adore a man who takes what he wants. Can I count on you for that?”
It’s a challenge, one that Astarion knows will press Gale’s buttons. There are very few men at the top in the corporate world who would not take that offer when presented to them on a silver platter. Or in this case, in a very short mini-skirt that barely covered the bottom of his ass cheeks.
Something flashes in Gale’s eyes. “On the desk, Astarion.”
Astarion does as he’s ordered, stretching languidly so that his top rides up a few inches. He sees Gale’s gaze flash towards the surgery scars at the bottom of his chest. That’s his cue to spread his legs, rucking the skirt up to give Gale a full view of his cunt. “Like what you see, sir?” he asks, coyly.
“I…” Gale hesitates. “Are you… open to being pleasured there?”
The question catches Astarion off guard. “What?”
A blush is beginning to form on Gale’s cheeks. “I want to make sure that you are… comfortable. If your– ah… if that is off-limits.”
It takes a moment for his brain to catch up with what Gale means. It’s sweet, in a way that Astarion is not used to and makes him a little uncomfortable. To combat the sudden rapid pounding of his heart in his chest, he arches an eyebrow at him. “My cunt is all yours for tonight, darling.”
For a moment, Gale is shell-shocked, likely processing Astarion’s crude words. Then, he nods and drops to his knees in front of Astarion. “You can grab my hair if you need,” is the only warning he receives before he is being slid across the desk surface and a tongue is circling his cock, making him shudder and cry out, a deep seated roil of pleasure starting from the base of his spine shooting upwards.
Gale eats pussy with the same determination that Astarion imagines he displays in the boardroom, with single-minded focus. No one has ever done this for Astarion before, and he can’t help but to roll his hips forward, cries falling from his lips.
The oversensitivity of his dick causes him to curl his fingers into Gale’s hair in a fruitless attempt to pull him away. Gale does not let up, instead, moves downwards to curl his tongue into Astarion’s cunt.
He whines, squirming and wanting something bigger. Gale seems to know exactly what he is doing, as he returns to Astarion’s dick, applying suction at the same time that he slides two fingers into Astarion.
“A-Ah!” Astarion shrieks out at the sensation of the fingers pressing ruthlessly up against the wall of his cunt, curling upwards and making him grow even wetter. He doesn’t know if he wants to beg for mercy or for more.
The wet sounds of Gale fingering him fills the room, an accompaniment to the lewd sounds Astarion is making. After a few more beats, Astarion is forced to let go of Gale’s hair to support himself on the desk, just barely keeping himself up from how hard his arms are shaking.
“I’m ah– close, darling,” he gasps out. His intent is to get Gale to stop.
He does not, instead, he intensifies his efforts on Astarion’s pulsing clit, sliding a third finger in, curling them upwards over and over in a rapid staccato.
Astarion comes with a scream that absolutely wrecks his vocal cords, gushing everywhere, soaking Gale. His upper body collides with the hard surface of the desk as his arms give out and all he can do is lie there twitching, whimpering.
A shadow falls over him. In spite of the smug expression on his face, Gale's lower face is shining with Astarion's slick, a reminder that makes Astarion moan weakly as his cunt pulses again, squirting a little more.
“These clothes were not cheap, Mr. Ancunin.”
“You!” Astarion manages to get his elbows under him so he could at least angle himself to glare up at Gale.
“No matter.” He sheds his jacket before starting on the buttons of his white shirt, now transparent with how wet it was from Astarion squirting all over him. Gale is tanned all over, with body hair that is immaculately maintained that Astarion wants to run his hand over. “I'm sure you can afford to pay for the dry cleaning, being on your father's payroll.”
The unbridled lust gives way to an instinct to punch Gale at that comment. By the skin of his teeth, he manages to pull that down in favor of sneering up at him. “Getting to fuck me should be all the payment you need.”
An amused snort. “And yet, you're the only one who has come thus far. Quite spectacularly, I might add.”
Astarion feels himself flush– with his pale skin tone, he knows that the red will spread through his entire body. “What are you waiting for then?” He lies back down and brings his knees to his chest.
“Hmm.” Gale steps closer and looks down at Astarion, almost imperiously. There is pressure on the base of the plug that makes Astarion's entire body seize. “You came prepared.”
“I like to– ah!” Gale has a firm grip on the toy and is corkscrewing it in and out, withdrawing it just before the widest point, making it incredibly difficult to think. “-- be prepared, s– nngh , sir.”
“Unfortunately not quite prepared enough to not make a mess. Maybe next time you’ll learn your lesson.”
The swoop of arousal in his stomach shocks him at the promise of a next time . He never does repeats, not unless Cazador orders him to. “I'll hold you to that,” he replies.
Gale holds out one arm in front of his face. “Cufflinks, Astarion.”
Astarion reaches up to tug at the small metal adornments on Gale's sleeves. He sees that they are tri-colored, yellow, white, and rose gold intertwined on either end of the cufflink. His hands feel clumsy post-orgasm and it takes him longer than he would like to undo just one, even longer to do both. He holds them out to Gale, who plucks them from his grasp before tugging his crop top further up, over Astarion's head and discarding it on the floor.
The cold bite of metal against his chest makes Astarion hiss and he looks down to see Gale holding up the cufflinks to his nipples, studying them. “Gorgeous,” he praises, before dropping them carelessly on the desk next to him and removing his own shirt. “Up against the window, if you please, Astarion.”
Something about Gale's pointed use of his name made Astarion squirm, the need to please the older man wiggling to the surface of his brain. He scrambles off the desk to brace his hands against the window, where the lights of Waterdeep glow beneath them.
Smack . The hand whipping across his ass brings both pain and pleasure, and he cries out in surprise , pitching forward to collapse against the window. The slap shifts the plug within him, the dull pleasure from the movement a reprieve from the intensity of his previous orgasm. A heavy weight drapes over his body, teeth sinking into the juncture of his neck and shoulder as something large ruts against him, the slick from his cunt easing the slide in between his cheeks.
“What a good boy for me.”
A cock, thick and heavy, slides in between his folds, collecting up more of Astarion's natural lubricant. Astarion looks down, attempting to see just how large Gale is, but the miniskirt hitched up above his hips is in the way.
The movement of his head does not seem to escape Gale's notice, and Astarion finds his hips yanked back by a tight grip on the skirt, flattening it out at the front and giving him a front row seat to the monster currently moving in between his thighs. Gale is enormous . Astarion should be frightened, but in the face of one orgasm, he is not. In fact, all of his wants and needs in that moment boil down to one thing: getting absolutely railed by Gale Dekarios so hard that he will not be able to walk tomorrow.
Gale's other hand presses down on Astarion's lower spine, forcing him to arch his back. Presenting himself to Gale. “Deep breath,” he murmurs, before shifting his hips to catch the thick head at Astarion's dripping hole.
The slow slide is worse than if Gale had thrust in all at once. Astarion can feel everything , how Gale takes up so much space in his cunt that the plug moves. Finally, he bottoms out and Astarion swears he can feel the tip kissing his cervix.
“Fuck, you're tight,” Gale curses, his voice slightly breathless.
“M-move,” Astarion demands, pushing his hips back. He's never had both of his holes filled before and he can feel himself clenching helplessly around both the toy and Gale.
“ Hold on ,” Gale growls and begins to snap his hips like a man possessed, each thrust reaching the deepest parts of Astarion, pulling out the most sinful moans. “Do you like being on display like this, Astarion? Knowing that anyone could see you?”
Gale is filling up so much space in him that there is no space for words– he thinks he might be drooling, fucked out as he is.
“Ah, but you don’t care.” Astarion should hate how composed Gale is in this moment when all of his higher functions have been replaced by the need to keep Gale’s cock in him. He would be so good for Gale, keep that glorious dick warm, whether with his cunt or mouth, he didn’t care. “Shameless. Lucky for you, I like that.” Large hands grip Astarion’s hip in a tight bruising hold as Gale speeds up.
Astarion yelps as he loses his balance, and he finds the entire upper half of his body pressed against the glass, the arch of his back straining his muscles. His stomach clenches and he begins to convulse, the impending signs that he’s close.
“Stay there,” Gale hisses, continuing to pound into him, but somehow managing to have the focus to reach down and yank the buttplug out. The feeling of the widest part of the toy stretching him sends Astarion over the edge and he comes. To his shock, he squirts again, this time drenching the carpet with a darkening stain.
“ Fuck!” he cries out. It feels endless, the stimulation of Gale’s cock continuing to nail his g-spot prolonging his orgasm.
His trembling legs begin to collapse under him, but before he can go down hard, he is pinned in between Gale’s body and the window. “Do you think you can give me one more?” Gale whispers hotly in his ear, stilling his hips.
Astarion wants to say no, his wrung out brain overstimulated just being speared open on Gale’s cock. But he finds himself nodding and replying with a hoarse, “Yes.”
“ Good boy .” In a split second, Gale has pulled out of his cunt and is pressing into Astarion’s asshole, lubricated by the copious amounts of slick Astarion has produced.
The plug is one of Astarion’s bigger ones, but the girth is nothing compared to Gale’s cock bullying its way in. When the older man bottoms out, he feels it in the back of his throat and he has to take a deep breath, pressing his forehead against the cold glass and closing his eyes.
He is not given a reprieve, as Gale immediately begins moving, drawing out almost all the way before driving back in. “Touch yourself,” he commands. Astarion can feel the cock in him growing larger, as Gale gets close. But an order is an order, as he reaches down to rub at his cock with two fingers, in the precise, almost military way he knows will get him off. His cunt clenches around empty air, weeping to be filled, and for a moment, he’s afraid that he will not be able to come. The threat of disappointing Gale makes him redouble his efforts on his dick, and he is able to come once more, this time with a wrought-out wail as everything seized up. His vision goes white.
“Fuck!” Gale roars out, slamming his cock in as deeply as he can. Spurts of warm cum spill into him with every twitch and all Astarion can do is take it, feeling like a marionette with its strings cut.
After what feels like an eternity, Gale pulls out, supporting Astarion with an arm against his back. In the window, Astarion can see Gale looking down, likely admiring his work.
“You’re very open.”
“You would be too if you were fucked by a soda can,” Astarion snaps back, although it comes out slurred. He glances back at Gale.
“Hm,” he murmurs appraisingly. “Makes it easier to do this then.”
The plug slides back into Astarion’s hole, keeping him plugged up and full of Gale’s cum. Hot, in a way that he has never considered.
“Come, let’s get you to the couch.” An arm wraps around his torso to support him on the walk over to the dark purple sofa in the corner of the office. Astarion carefully makes sure that his skirt is tugged down as much as he can to avoid dirtying the fabric surface. “Do you need anything? You came a lot, you must be dehydrated.”
Astarion chokes on his own saliva, devolving into a coughing fit, which leaves him wheezing and gasping for breath. “You’re funnier than I thought you would be, darling.” He chances a glance at the clock. “I must be getting home soon, though. A taxi may be the least you could do?”
Gale slowly nods. “You’re welcome to come home with me, if you’d like. Uhm. Let me take care of you. I… did do a number on you.”
The shyness is a stark contrast to the rough way Gale had treated him just moments before. It’s endearing, in a way. Astarion gives him a crooked smile. “A little early to be asking me on a date, don’t you think?”
“I don’t… usually do this.”
“What– fuck the over-half-your-age sons of your competitors?” Astarion couldn’t help the deranged laughter that follows the absurd question as he shoots out the reminder of their age difference. Nineteen to Gale’s forty-five.
Gale winces at that but shakes his head. “Fuck someone that I find intriguing before taking them out on a date.”
The serious response stuns Astarion into silence.
“Let me make it up to you. We both know that you would be returning to an empty house.”
That stings, but Astarion couldn’t deny that was the truth, and maybe that’s what makes him nod. “I suppose… I can keep an old lonely man company for a night.”
Gale’s face brightens, as if he is actually excited to take Astarion home. Usually he gets kicked out immediately after the sex, not… whatever this is. It’s unsettling.
But maybe that is exactly what makes him crush the memory card under the heel of his boot on the pavement outside, grinding it to bits, before accepting Gale’s helping hand into the car.