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merv606 · 2 days ago

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AU where Daniel is an escort and billionaire Mr. Silver’s date for one night. Daniel is flattered to be requested by him, and is pleased that he’ll be paid nicely for his company. He doesn’t expect anything more after the night despite catching feelings for the man, but Mr. Silver has other plans and doesn’t want to let him go…

Maybe NINY era Daniel and CK Terry, but if that’s too much maybe Black Friday Terry instead or whatever haha.

😎

It was his first day on the job - in that it’s his first real client. The last few weeks have been nothing but training that turned out to be way more intense than Daniel thought, given the job itself.

But once he thought about it, it made sense.

Knowing they catered to higher clientele - and that most escorts would be for appearances only - dates to galas and other important functions where appearances were everything, especially the thin veneer of civility these men who paid for such services maintained. So their manners needed to be impeccable, and their ability to navigate the minefield of social politics.

While some escorts offered sexual services - Daniel didn’t think he was ready for that - if ever - even if that was where the real money was - considering some of the stories he’s already heard.

The older ones tsk, hoping he’ll change his mind.

“Face like that, you’d be turning down marriage proposals, villas in Spain, private jets, and god knows what else.”

Daniel isn’t too sure about that though.

He’s not even fit, like most of the other escorts. Still too slender, limbs too long and thin, and hips too sharp.

“Oh there’s a huge market for that darling, trust us.”

Maybe he does have a lot to learn.

A twink, he’s heard them call him, but he’s too new to this to know what it means, and truth be told, he’s afraid to ask.

But for his first client to be THE Terry Silver?!

Daniel may not know who he is, but every other escort does.

“He never uses these things.”

“Not like a man like that is hurting for company,” one remarks.

“What did they tell you?” another one asks.

“He’s in New York for the weekend and a last minute gala had been sprung on him.”

“I heard that as soon as he saw your picture he didn’t look at anyone else. Just said that it didn’t matter if you were already booked - he’d pay triple,” another says, eyeing Daniel with jealousy and admiration, even if jealousy was winning.

Jesus Daniel thinks, he only left the meeting himself less than ten minutes ago. How does word travel this fast.

“He knows you don’t sleep with the clients, right?” One scoffs.

“He does,” Daniel answers. He thinks he might be the only one actually.

He thinks back to the meeting, and what was implied though.

“Your contract for the night is already drawn up. Read it over and if you’re satisfied, sign there.”

He does. The way they speak of Terry Silver, he doesn’t think he could do anything else.

“A car will be at your place at 7 sharp - be ready.”

Daniel nods, slightly overwhelmed.

“His tailor will be here shortly to measure you for a suit.”

Daniel opens his mouth.

“All on Silver’s dime.”

Extremely overwhelmed.

“In addition to your fee there is also a bonus built in for your behaviour for the night. I strongly suggest to impress him.”

——————-

The car isn’t a car at all, rather a ridiculously long limo, but it arrives at 7, as promised, and the door is opened for him.

He finally meets Terry, face to face, and if he thought he was handsome from the few grainy photos he had found on the web, they are nothing compared to the result thing.

He has only maybe 10 or 12 years on Daniel, but is greying already. It doesn’t detract from his looks, rather adds to them.

Daniel wishes he had styled his own hair better, and maybe sprung for a hair cut, aware now of how floppy it looks.

Terry offers him champagne and he takes it, forcing himself to sip it and not down it in one go like his nerves are screaming at him to do.

They make small talk, and even if the limo is spacious, it still feels small somehow.

Terry though is amenable, and is great at conversation, and is proving to be everything Daniel wasn’t expecting, setting down nerves at ease.

They arrive quicker than he was expecting, but Terry instructs the driver to give them a few moments.

He reaches out, fixing Daniel’s bow tie, the same blood red shade as Terry’s own tie.

“There we go. Now you’re perfect.” Terry tucks a lock of hair behind Daniel’s ear. “Now, just breathe.”

The door is opened and Terry steps out first, turning and bending slightly to offer his hand to help Daniel out.

The lightbulbs flash as they walk the red carpet inside, his arm tucked under Terry’s with the older man’s hand on top of his.

They have to pose for a few. Some together and some with just Terry, Daniel standing to the side.

He swears he’ll be seeing flashing lights behind his eyes when he blinks for the rest of the night.

Terry stops again once inside, waiting for the auras of flashing lights he knows are dancing behind Daniel’s eyelids to stop - even offering some tips to help.

That’s not the weird part though, even if the cameras and shouting for his attention were jarring.

It’s actually the constant looks his way that throw him, as Terry begins guiding them again, further inside, now that Daniel can see properly again.

“Everyone is looking at you,” Daniel whispers, noticing how unbothered Terry is with it all. He must be used to it, Daniel thinks. He can’t imagine ever being used to this though.

“Oh, it’s not me they’re looking at,” Terry answers, bemused at the boy’s naivety. They’ll be the talk of the town by night’s end, if not already.

They sit, Terry pulling out Daniel’s chair before taking his own.

The conversation flows easily between them, lien it did in the limo, and when the first dish is served, Terry watches amused as Daniel clearly panics, his hand hovering over several of the utensils.

“I am sorry, I …” he doesn’t know what’s wrong with him. He was top marks in etiquette class - one of the reasons he was selected - besides the fact he fit the description Terry wanted to a near tee.

“It’s that one first,” Terry points out, “then work your way outwards.”

Relief floods through Daniel, grateful that Terry is everything he wasn’t expecting. For his patience with Daniel’s ignorance especially when he should know better, and when he thanks the older man, Terry’s hand lands on his upper thigh, rubbing softly before squeezing in a reassuring manner.

He doesn’t take it off.

“I’m forgetting everything it seems. Nervous,” he adds.

“You need not be. You’re doing wonderful.”

“I don’t want to make you look bad.”

“Never,” Terry reassures.

It seems that everyone here knows each other in some way, even if it is superficial - something that is the norm in these circles - so Daniel was told by his fellow escorts.

So Daniel stands and listens, following the parts he can, smiling and laughing when appropriate, and speaking when addressed.

As it were, some of his coworkers are here tonight, however, unlike them, he is so new to this that no one recognizes him as an elite escort, his face not familiar like his longer tenured coworkers

As such, Terry introduces Daniel as his personal assistant - new to the job. “Good practice. He’ll need to be used to this if he continues on,” Terry had said charmingly, although some of the women know better. They may not suspect escort, but they know, from their own experience, even if he is Terry’s PA that his duties tonight will be more than professional.

A woman, dripping in diamonds, especially the one on her left hand, turns to Daniel, a blinding white tooth smile, as she knowingly whispers, “I was this one’s personal assistant too,” she winks, inclining her head to a much, much older man sitting next to her, obviously her husband.

He sits, speaking when spoken to, letting Terry control the conversation, the narrative he’s created; control it all.

Terry seems a man who is used to control; relishes in it.

When they finally finish dining, they spend the time mostly by themselves, Daniel noticing that if someone tries to chat them up that Terry makes perfect conversation, but always ends it as soon as he politely do so before leading them away, a hand on the small of his back.

The one moment Terry’s attention is diverted from Daniel, another man suddenly swoops in, handing him a glass of champagne, taking the barely sipped one from Daniel’s hand.

Luckily his rescue doesn’t take long but, the other man, clearly having had a bit too much, tries to keep Daniel from leaving, a hard grip on his wrist, and Daniel ends up spilling his champagne down the front of Terry’s shirt.

Daniel stammers out apologies, dragging the older man into the bathroom, his intent to clean up his mess.

Dabbing a wet cloth down it, Daniel frowns. This isn’t working,

“Maybe if you take it off I can ….”

“If you wanted to get me out of my shirt all you had to do was ask,” Terry responds breezily, grasping Daniel’s hand in his, giving it a quick kiss.

Daniel can feel the blush hot on his cheeks and the smirk on Terry’s face lets him know it must also be very visible.

“I mean to clean it,” he says, weakly, and his voice is anything but even, so aware of the how close the older man is, the scent of him, the sheer size of him, how good it feels to have his hand still on the larger one.

“Oh this ruined,” Terry confirms.

“How much was it?”

Terry waves his hand. “Certainly nothing for you to worry your pretty head about. It wasn’t your fault.”

Daniel is not sure what to say in the face of that - in the face of it all. Even if it was Terry who moved startlingly fast to break the hold the man had on Daniel’s wrist, causing the spill in the first place.

“We will have to cut our time here short, however.”

Daniel is technically on the clock for several more hours, but he won’t hold Terry to them. After all, he can’t blame Terry for wanting to cut it short - this has been a disaster.

Something must show on his face, because Terry looks up from where he had been dabbing his shirt.

“It’s fine. I’ve been wanting to leave for hours now, but haven’t been able to politely do so, and this is the perfect opportunity. I should be thanking you.”

“Of course. I can see myself home …”

“You misunderstand. We can continue our night elsewhere,” Terry cuts him of, smiling.

“You shouldn’t feel the need to …”

“I still have you for a few more hours, do I not?”

“Of course. I just thought ….” A hand on the back of his neck now as he rubs himself nervously almost.

“Nonsense. I’ve enjoyed myself immensely tonight. You are excellent company. Do not think this night as anything but the glowing success it was.”

They end up back at Terry’s penthouse, a place he keeps in the city as he prefers to stay anywhere but hotels unless necessary, and often finds himself in New York for various business.

More drinks are shared between them, and conversation.

“I prefer this, truth be told. Now I have you all to myself,” Terry says as he takes the empty flute, laying it down, his eyes burning down into Daniel’s.

“I …. my contact isn’t for that,” and they both hear the disappointment in his voice, a plump lower lip captured and worried between his teeth.

“Well, once you’re officially off the clock your time is yours to do with what you wish is it not?!”

“It is.”

“I would ask you second if here with me, if you wish. Let me make love to you,” a hand on the side of Daniel’s face, felling the nod he gives, his words failing him.

They stand, Daniel in his arms, both men looking down at the wrist watch, the seconds ticking down - a sort of game of anticipation.

“Officially off the clock now ….” The rest of what Daniel was going to say swallowed by the older man’s mouth on his and it’s all he can do to keep up.

On his tip toes, arms around his neck, large hands on his ass urging him up until he’s lifted up, wrapping his legs around the older man’s waist.

His back hits the wall, and he’s not sure which is more of the unmovable force, the wall of the hard body trapping him to it.

“Have you been with a man before?” Terry asks, thumbs tracing and pulling down his bottom lip, slipping into his mouth as Daniel sucks on it.

“Yes,” Daniel answers, pulling off with an audible pop, and then feels the need to add the actual number: two. There was Jake, in college, a few drunken rumblings, and then some random in bar one night, just to help him sort his own confused feelings.

“Did you let any of them inside you?!!”

He nods, sucking the thumb back in his mouth as he does, unable to help himself, watching as Terry’s eyes go black.

“How many times sweetheart?”

“Just a few,” he stutters as Terry’s hand grips his ass.

“And you liked it?!”

He can hear Terry unzip his own fly, and Daniel’s eyes drop down, widening.

He liked the pleasure of the act well enough, but the discomfort, and the pain that accompanied it not so much.

And Terry is, in fact, proportional.

The largest Daniel has ever even seen. In reality and in any other form.

“Want you to put that pretty mouth of yours to work first,” he says stroking his cock and Daniel drops to his knees, rubbing his face again the man’s upper thigh, before swallowing him down without any preamble.

“Fuck,” Daniel hears before feeling fingers tangle in his hair.

Head bobbing up and down, mouth pulling off enough to suck at the head, hand wrapped around the thick cock, solid and hard, wet with his own saliva.

Terry pulls him off, his cock dragging out, ropes of precum connecting them, fucking in and out a few times before pulling out for good.

“But,” Daniel stammers, confused, worried it wasn’t pleasing to the older man. D ahem finds he wants nothing more than to please the older man.

“Not your mouth I want to come in, sweetheart,” and Daniel’s asss clenches at the roughness of his voice, at the knowledge of what it about to come; what he is about to be made to take.

He finds himself on his back on a large bed, the older man’s body eclipsing him, pressing him down.

They kiss, their cocks rubbing, Daniel spreading his legs, knees in either side of the older man, before his warmth leaves.

“Hands and knees for me.”

Not a request, and not a demand, but something that they both know he’ll obey.

Terry is fisting himself as he says it, Daniel throwing a loon over his shoulder once he’s in the desired position.

Cheeks spread next, and god he hopes Terry isn’t going to just push in, but then a tongue licks over his hole and he shouts, “oh fuck,” biting the sheets, indents of his teeth when he finally lets up.

“You like this too?!” Another lick, and Daniel whimpers, pushing back; he can’t help it. “My mouth in your gorgeous ass.”

And oh, no one has ever done that to him before. He didn’t even know that it was a thing but he is glad to know it now.

He may sob this out, he’s not sure, but Terry pauses, taking in how wrecked the boy is already, considering. “I find it hard to believe no one has wanted a taste of this gorgeous hole before, sweetheart.”

“No, no one has ever … “ but then Terry is burying his face in his ass, eating him out proper.

Humping back, but trying to get away all the same, overwhelmed, Terry grabs his thighs to keep him in place and Daniel braces himself against the bed, his arms flat to the mattress, his ass high in the air for the older man. It’s all he can do really, to just hang on - a thing for the older man to use. It feels like his body is something new to him, not aware of how it could feel until now - being played by the older man like a master playing their instrument - like he’s been playing Daniel for years which, it certainty feels like it.

“Going to come,” he gasps out, which seems to only encourage Terry.

He shoots onto the bed below him, not even a hand on his cock.

“Sorry,” he says, embarrassed at how quickly he came, and Terry laughs out, “don’t be. It won’t the the only one I get out of you tonight.”

“But, I already came,” he stammers out, and although he can come more than once in a night, he still needs some time to gather himself.

Terry chuckles.

“This is why you need a man, sweetheart - to show you these things.”

“On your back now, legs open for me.”

A hand on his hip, guiding him, as Terry tells him, “I want to see your face when I take you for the first time.”

He moans, can’t help it.

“That’s it, hold them like this.” He places Daniel’s hands along the backs of his own thighs. “Now pull them back to your chest … perfect.”

He feels exposed, he is exposed, his hole on display for the older man.

“Keep them like that, nice and wide for me.”

The sound of a cap of lube, Terry rubbing his fingers together to warm it before Bering then to his hole. “Gorgeous,” he remarks, tracing the rim until the flesh softens and yikes a before dipping the tip inside, the pressure unrelenting, until it’s inside him up to the first then second knuckle.

It doesn’t take long for him to become comfortable enough with one, hips pressing into the fingers, for Terry to add another, and another and then another.

Four fingers fucking in and he would have protested by now, but he remembers the size of Terry’s cock, the sheer size and how it has felt in his mouth and hand.

The head of said cock, teasing the lube slick hole now, which he spits on, even if it’s not really needed.

“Condom,” he asks.

“I’m clean. As are you.”

The escort service is very high end with regular testing, especially at the client’s request.

He’s never done it bare, saying as such and Terry’s eyes go black at the knowledge. “Never had a man come deep inside you?”

“No,” he whimpers, hands bunching the sheets between his fingers as the head of his cock breeches him.

“You’re going to like it,” he groans, not stopping, but going slow enough for his body to try and adjust to the sheer girth of the cock as it opens him up.

“Relax. There we go. Let me in,” he rumbles, hand on Daniel’s stomach.

“Fuck you’re tight,” he grits ….

“You’re so big,” he responds and Terry chuckles.

“Relax for me baby …. Let me in …. There you go … doing so good.”

Oddly, it doesn’t hurt as much as it did in the past.

Besides the initial pain of the penetration, his hole stretching what he thought would be impossibly wide to let the older man inside, while bright, was quick, discomfort in it’s wake as he gets used to the older man indie him, but it quickly seems like just a memory as Terry’s cock hits his prostate, pleasure burning in it’s wake.

He cries out, ass clenching on the cock, hands grasping the sheets in fists now.

“There we go,” Terry smirks, “found it.”

Terry rubs over his fist, until it relaxes enough to lace their fingers together.

“So fucking tight,” he growls, “like I knew you would be. God your ass feels so good.”

“Your,” he gasps as Terry begins to rock into him, fucking him. “Your cock feels good. Fuck, how is it so big.”

It’s a pure porno line and should sound cheesy - ridiculous - but there is a sincerity there even in the way he moans it out. How he circles his hips and the wet sound as his ass opens for energy inch as it slides in and out, how his legs fall open even wider - showing Teddy how much he really likes that.

Terry laughs, “my little size queen,” licking into his mouth messily.

Daniel believes him.

He can feel it in his throat.

“You’ll be ruined for anyone else. No one else will be able to fill this ass like you need now,” he slams his hand over his wrist, large hand wrapped around it ridiculously easy, as is the ease at which he holds it to the mattress. Daniel wouldn’t be able to break the hold even if he tries

Daniel flexes, just to see and it tightens, and that does something to him he can’t quite describe but god he’s never been more turned on.

“Daddy knows best baby boy,” and oh that is new. Daniel arches up, sudden and violent, his release shooting out and hitting Terry’s chest, his ass griping the cock so tight Terry stops thrusting, only shoving back inside once he loosens up, spilling himself inside moments later.

Pulling out, the wet noise his ass makes - full of lube and the older man’s spit and cum.

Despite the ache in his ass - a feel he can’t exactly say is unpleasant. It just reminds him of how well used he was - how good he was for Terry, and later on Terry takes him again, face down ass up this time, even having Daniel ride him come the morning light. Although, if he’s being honest, is not him bouncing on it like he imagined, but more him sobbing and struggling to take him in that position, the cock so deep, and twice as large he swears, his legs spread so wide on either side as he sinks down. That seems to do it for Terry though, who helps him fuck himself on it, large hands on a narrow waist, fingers leaving greedy bruises, praising him for doing so good. “know it’s a lot to take baby, especially like this, and your ass is so tight even after I’ve had it.”

Large hands on narrow hips helping him lift up and down, the punched out little gasps every time Terry bottoms out, each time his cock brushed the swollen prostate inside him, until he’s telling Daniel to rock back and fourth.

Teaching him how to ride his cock.

A long soak in the obnoxiously big tub, overlooking the New York skyline as night falls is next.

By the time Terry has had his fill, Daniel is more glad than ever that he has the next few days off, even if this proves to not be a thing because Terry ends up occupying those days. Terry quickly ensures there is no time in which they will not be apart.

It’s all off the book - it’s his weekend after off - but he quickly agrees.

One of the older ones who took Daniel under his wing tried to advise against it.

“He’s trying to get your services without paying for it”

Besides the fact Terry doesn’t strike him as such a man - he is liberal with his money when they go out - paying for everything - Daniel sees a side of New York he never did before - could never afford to - and he tries to commit it to memory - knowing he’ll never see it again.

So he can’t say he feels used, even if he has also happily spread his legs for the older man multiple times throughout the weekend, and his mouth, blowing Terry on several occasions.

It is, hands down, the best sex Daniel has ever had.

Terry then officially pays for the following week of Daniel’s time, extending his own stay in NY to accommodate it.

Daniel can’t say he is anything but distraught when the time comes for Terry to have to leave, although it doesn’t last long, Terry explains that while he is returning to LA out of necessity, he will be back to NY on the weekend, if not earlier, whisking him away to the penthouse suite when he does.

Having him against the floor to ceiling glass window the second the door is closed behind him. He has already told Daniel to have his ass ready for when he arrived.

“Who wouldn’t give you the world?” Moving his hair to the side, kissing his neck, their eyes meeting the glass’s reflection.

“It’s too bad you have to go,” Daniel laments as they lie on the bed now in the afterglow, Daniel on his back staring at the ceiling as Terry smokes his cigar - something he likes to do after sexTerry’s come slowly making it’s way out of him - the older man pathologically obsessed with marking Daniel in that way.

“What if I didn’t?” Terry questions.

“What?” Daniel turns his head to look at the older man.

“Or more likely, you coming with me?” He says, blowing smoke out.

Rolling to his side now, he just stares at the older man, and he’s pretty sure his mouth is open.

Terry laughs. “Now did you really think I was leaving you here?”

Daniel is honestly at a loss at what to say.

“I went home to arrange a few things for your arrival is all.”

“But,” he starts, head spinning. He was not expecting the conversation to take this turn.

“I’m not leaving you here,”is all Terry says, matter of fact - end of argument, even if there was one (Daniel’s not sure) - case closed.

“My life is here.”

“Your life is with me now,” Terry answers, with no real arrogance - no, just the air of a man used to getting his own way.

It can’t be that easy, he thinks.

“Daniel, you told me yourself, you have no family here, no friends.”

This is true, and it’s not like he’s made any headway with the acting. He took the escort job to save up money for acting classes, to both improve and set up some connections.

“You also have no job.” Terry adds.

He bought the business, and Daniel certainly won’t be rented out, ensuring no other man or woman could have him was the point, and if any escort business knows what’s good for them they would not take him on a should be try to find other employment. Although Terry isn’t betting on that. What he has to offer if much better after all.

“The thought of any other man touching you …” Terry trails off,

He should be mad, he should, but, it’s not like he even wanted the job. That Terry got him first, he considers himself endlessly lucky.

Still.

“This can’t last,” Daniel starts.

“Let me be the judge of that.”

There has been no one, so far, that has kept Terrys attention the way Daniel has. No one he even considered giving him name to, expect now.

“For each month we are together a payout of $100,000 that, should we break up, would be payable to you.”

“I’m not a whore,” he says quietly, but there’s no real heat. Every time he has slept with Terry, he’s made a point that it be in his time.

“Certainly not, and neither are wives. That’s just a standard prenup in our circles.”

“Oh,” he says.

“You told me film school is what you were hoping to achieve. That you wanted to save enough money from working.” A short lived career thanks to Terry.

“It still is,” he agrees.

“So you can go. Here or California. It doesn’t really matter. I prefer California’s weather but I can work from anywhere really. I don’t mind a few years in New York, if it’s needed. A Change of scenery, if you’re that scenery,” Terry says.

Daniel thinks the same thing applies. He won’t mind a change, so long as that change is Terry.

#ask #I got an ask 🤩#cobra kai #daniel larusso #karate kid #terry silver #silverusso #silverrusso

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123corporatetransport · 1 month ago

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