Chance/Parker/Diceplay
Sugar Daddy Headcanons
I must confess, I love the concept of sugar daddies/mommies. However, only the concept. Not in practice.
These are NSFW, no minors!
Chance
He became a millionaire after growing a very popular G&G streaming channel. While he donates a good chunk of the money, he has no idea what to do with the rest. The most frivolous he is is when purchasing nerdy merchandise. Otherwise, he lives fairly modestly. A nice two bedroom apartment on the outskirts of a major city.
Eventually he finds you. Looking stunning in your costume during the local renaissance fair. He himself was also dressed up, a bit brooding and mysterious beneath that hood. Discovering you both attended the festival alone, he asks to join you for the day.
“Ho! Fellow traveler!” He says with a nervous lilt to his voice.
“Hoe?” You question.
“N-not like that!” He raises his hands up to show he isn’t a threat.
Snickering, you shake your head.
“I’m fucking with you, dude.”
“Oh! Ah, I see!” He chuckles awkwardly. “I hope this isn’t weird, but I noticed that you are on your own.”
“That obvious, huh?” You try to get a look at him, but his hood has much of his face in shadow.
“A bit, but fear not! I am alone as well!” He twiddled his fingers nervously. “So, would you like to go about the fair together?” He asked, voice soft.
“Sure! But before we continue, could I see what my fellow traveler looks like? And maybe get their name?” You gave him a soft smile that had his heart swelling.
“Why of course!” He pulled off his hood, revealing quite the handsome face. “I’m Chance.” He offered his hand.
You took it, giving him your name. He said it back to you, making your cheeks flush. Oh, you’d love it if he spoke your name some more.
“Uh, shall we?” He motioned for you to move along with him.
“We shall!”
Both of you wander the festival talking about everything and nothing. When you get peckish, you stop for a meal. Chance will not let you pay. Whatever, you’ll cover the next time. However, you never get the opportunity. You try to purchase some jewelry? Chance has got it. You eyeballed a leatherbound journal? Chance hands it to you like it’s nothing. As the day progresses, Chance realizes he really likes this. He really likes you, and seeing the sparkling adoration in your eyes when he procures an item for you makes him feel… good.
During your conversations, he finds out how you’re a broke student trying to finish your masters. While you greatly appreciate his generosity, you couldn’t accept all of this. However, he insists.
When the day ends, you find yourself heading home safely in an Uber (paid for by Chance), a pile of gifts, and his number tucked into your pocket.
It takes a few days, but you muster up the courage to text him. When you do, he is ecstatic. Immediately asking you out on a date.
Of course, it’s very fancy. While Chance doesn’t think you’re a golddigger, he does not have much experience in the dating department. People like fancy restaurants, right?
When you meet him at the restaurant, you are extremely overwhelmed. Trying to figure out what you can afford to order. You never let people pay on the first date. Chance realizes this and reassures you. Telling you to get whatever you want. Anything at all. There’s a glimmer in his eyes when you accept and order something appealing.
While you’re not the most comfortable with it at first, you eventually get used to Chance treating you constantly. Anything and everything you want is yours.
“I saw you eyeing that book in the store, do you want it? I think it’s a series. I can get you all signed copies!” He exclaimed, that familiar gleam in his eyes.
The man turns what would be a $20 purchase into a $500 one. If he spots that you like something, it will end up in your hands at some point. He will also do a lot of research into some of his gifts for you, making sure you end up with only the best. It’s not a hassle for him, in fact, he likes it. Almost like he’s been given a challenge.
Of course, you indulged in his wants too. The man loves his roleplay, and with his funds, you can become anyone he wants you to be. Royalty locked in a tower ready to be saved then ravaged by their knight in shining armor. A seductive assassin needing to woo the wealthy nobleman. A kidnapped innkeeper on a pirate ship. The possibilities were endless and always came with a well crafted costume and story.
You can’t say you didn’t enjoy it as well. It seemed like Chance’s sexual satisfaction came from you joining in on the roleplays. When it came down to business, the man worshipped you like a god. (Which just so happened to be one of the roleplays you partook in).
That man love, love, loves to go down on you. Telling you how he could spend days between your thighs. Licking and sucking away at your overstimulated sex till you’re babbling incoherently.
The way he fucked you depended entirely on how you were playing in the bedroom. He loves to manhandle you when you play as royalty. Taking you from behind with a thick hand around your throat. But, he also loves when you ride him like no tomorrow. Whimpering and begging for you to let him cum.
Then there are the times you make love. No scenario planned out. Just the feeling of warm hands sliding up your thighs. Soft kisses pressed to your jaw as sweet nothings were whispered in your ear. Before you knew it, you were beneath him. Cock stretching you out deliciously slow. Every thrust making you shiver and moan. The man awestruck as he watched you fall apart beneath him. Absolutely in love with a person like you that would have him. Just hearing you say those three simple words has him cumming inside you.
While he tries not to show it, he can be a bit possessive. When someone looks at you the wrong way, he makes sure you know who you belong to. He has a bit of a thing for marking you up to lay his claim. Not that you mind. Once or twice, he’s caught you appreciating the bruises that litter your neck and chest.
Since he’s relatively famous in the nerdy-sphere, he’s always reassuring you that he’s yours all the way. Honestly, it doesn’t really bother you that his fans try to flirt with him, but it bothers him. He wants to make sure that you know where his loyalties lie. After he comes back from a convention or fan event, he’s making love to you. Needing to share his unwavering affections for you to make sure you’ll never forget. And you never do.
Parker
He owns a game company that gained quite the notoriety and subsequently earned millions. Though he’s not one for the constraints of capitalism, so he tries to get rid of the cash. Whether it’s through charities, or donating to research efforts.
Parker stumbled upon you when you were working your part-time job at a local game store. He spotted you putting out some new games that just so happened to be ones that he had a hand in creating. When he sees you, he’s enamored. Immediately, he decides he needs to get to know you.
Sidling up to you, he tries to get your attention. You eye him out of your peripheral, asking if he needs anything.
“You play this before?” He asks, pointing at the stack of game boxes in your hands.
“Uh no, we just got it in.”
“Cool, cool.” He attempts to nod nonchalantly. “I’m Parker!” He introduces himself with an extended arm, then realizes you have no way to shake his hand.
“Cool…” You look around you, wondering if someone is trying to prank you.
“I made that game.” He said, pointing at the stack again.
“Neat.” This was becoming very awkward. “I’m sorry, do you need help with anything? I really need to keep restocking.”
“S-sorry. Gosh, I’m so bad at this.” He stuttered nervously, face red. “You’re like, really hot.” He clamps his mouth shut at the confession.
Your face turns red, as you take in the man before you. Cocking your head to the side, you realize, he’s pretty good looking himself.
“Uh, that probably came off super creepy.” He let out a long breath.
“Just a bit.” Leaning the boxes on your hip, you pinch your fingers together for emphasis.
“Can I start over?” He asks, eyes pleading with you.
Shrugging your shoulders, you give him a nod.
“Thank you.” He breathed out in relief.
“Hi, I’m Parker.”
You give your name to him.
“You are a very attractive person, and I would like to go on a date with you.”
“Are you asking me out?” You question, now amused at the situation you have found yourself in.
“Yes, I am.” He blushes.
“Okay, Parker. I’m off at seven.” You give him a coy smirk, and wave him off.
He’s right on time when you're off. Nervously tapping his foot when he sees you exit the store.
The impromptu date is fun. You grab ice cream, go on a walk around a park, he tells you terrible jokes, it’s nice. Then he invites you back to his place, not to sleep with you, but he has a ton of games that you guys could play.
Based on his appearance, you assume he’s taking you to a studio apartment of some sort. Little do you know, he lives in a fucking penthouse. The kind that has an elevator that goes directly to his apartment, making you realize he’s got MONEY money.
Walking into the apartment, you gaze around in awe. It was huge, with very tall ceilings. It’s oddly decorated with various knicknacks, antique games, and colorful furniture. All of it clearly fit Parker’s style.
He invites you to his game room. A space with shelves filled with all kinds of games. Although you work at a game store, the amount is overwhelming. He asks you to pick a game, so you go for something simple. A classic like Uno or chess. It doesn’t matter what you pick, Parker’s just ecstatic that you’re playing something with him. He is falling even harder when you beat him at whatever game you’re playing. Insisting that you’ll have to keep playing against him.
Before you know it, you’ve spent a few hours just playing with him. Each of you sharing bits about your lives as you draw cards or move game pieces. Parker is loving every moment of it. When you eventually mention the kind of life you live as a broke, single person, gears start moving in his brain. Perhaps he could assist you, it’s not like he needs the money.
When he starts to aid you financially, he discovers he really likes it. Eventually, you find yourself barely lifting a finger. Your rent? Paid for on the dot every month, until he decides he really wants you to move in with him. When your phone breaks? You’ve got a new one, plus you’re on Parker’s plan now. If you even mention wanting something, you’ve got it.
You don’t know how to handle all of this at first. Parker is pretty forward with everything that he does, and when he discovers he enjoys something, he’s enjoying it to the fullest. So treating you is honestly treating himself. You can try to get him to ease up, but the most that’s going to do is keep his enjoyment on the down-low. Yeah, you’re not getting out of this easily, so it’s best to just accept it for what it is.
“C’mon sweetheart, you know how much I love treating you. Just enjoy it, I know I am.” Parker says as you watch him sign a check for a brand-spanking new car just for you. “I’m tired of you driving that lemon anyways. So, just accept it.” He smirks as he presses a kiss to your lips.
Parker doesn’t expect anything in return outside of seeing you happy. However, if you wish to give him some sugar, he certainly won’t mind. He loves getting you on your knees before him, and enjoys when you praise him or give him “thanks,” especially when you do so with that pretty mouth of yours. Whispering a “thank you” practically has the man cumming immediately.
I think Parker is the type of guy that likes to show you off. I don’t know if he’s necessarily possessive, but he does like knowing that you’re his. The man does like to bite, and will make sure the world sees those lovely marks he presses into your skin.
In terms of actually fucking you, he’s a desperate whiny mess. Running a business does keep him busy, so when he actually has time with you, he’s using it. Oftentimes that ends up meaning he’s using you. Letting out all that pent up frustration from dealing with bureaucrats and upper management bullshit. You’re getting absolutely railed if it’s been a particularly stressful day. Don’t worry, he makes sure to let you know he’s not mad at you. When he’s done he’s giving you the sweetest aftercare. Pressing soft loving kisses to your skin as he showers you with praise and adoration. Exclaiming how lucky he is to have someone like you putting up with the likes of him.
Diceplay
Parker and Chance run a YouTube/streaming channel that has gained huge notoriety within the last five years. What started as a gaming channel in their old apartment has turned into a studio run conglomerate headed by the two of them. So, at this point, they’re loaded.
In walks you, a journalism intern for a local station here to interview them about the success of their latest charity stream. Parker and Chance have a fairly lowkey, but public relationship with each other. They weren’t looking for a third, but they also aren’t necessarily opposed to it either. Especially not when someone like you walks into their studio. Absolutely stunning with a lovely personality to boot. It’s clear from speaking with you what your position in life is. A throwaway thought about the lack of pay from your job has them raising their brows and shooting a knowing look with each other.
When the interview is over, they invite you out for a drink at a nearby bar. After a quick sidebar conversation, they both confirm their shared attraction toward you and wish to see where this could go. You accept their invite and they drag you along with them to a small spot just down the road from the studio. Who wouldn’t say “yes” to such a famous couple? Plus, they were quite attractive. Not that you thought you had the chance, but still…
“So you have another job as well as the internship?” Chance asks you before taking a sip of his beer.
“Yeah.” You let out a sad sigh. “Just a sales associate at a clothes store as I try to get through college. Nothing special, but it does pay the bills. Just barely.”
Again, Parker and Chance share a knowing glance. It’s as if you had come to them at the perfect opportunity.
“You know what you’ll be doing once you’re done with school?” Parker asks.
“Hopefully this internship will get me a position at the station, otherwise I might move back home while job hunting. I’ll have to pay off my debt somehow.” You let out an awkward chuckle.
Like these guys would know or care about student loans. That would be chump change to them.
“What about you guys? Got anything new and cool coming up. Off the record, of course.” You let out a small chuckle.
Gosh, weren’t you just the cutest thing. The two share a polite chuckle as well, allowing themselves to divulge one new thing they’re planning. Though they had a feeling they’d be informing you of much more very soon.
“We should get going, but it was truly lovely to meet you.” Chance says, lifting your hand to his lips. Pressing a soft kiss to your hand, he smirked as he spotted the red dusting your cheeks.
“I’m more of a hugger.” Parker said, opening his arms in an offer. One that you took, and he pulled you into a tight embrace. Again, your cheeks darkened.
“Hope to see you soon. You should give us a call or shoot us a message to meet up sometime.” Parker says after writing down his and Chance’s numbers on a napkin.
You hold the item delicately with wide-eyes, as if the object in your hand isn’t real.
“Seriously?” You ask with a confounded expression.
“Of course. We like you.” Chance says it so nonchalantly, you again feel as if this interaction is merely a dream. “Talk to you soon.” He sends you a wink before he and Parker leave the bar.
The two of them had collectively decided they would have you. When you don’t text them right away, they take matters into their own hands. Speaking with the admissions and aid office at your school, they use their connections to pay off any of your bills and your student loans. When you go to pay, you find your balance at zero. As you wrack your brain as to how that could happen, your mind immediately goes to the two men. Finally, you decide to call them. Asking if they were the ones to pay off your loans.
“That depends, would you be willing to go on a date with us?” You could practically hear Parker’s smirk through the phone.
“I thought you and Chance were dating.”
“We are.” Parker chuckled. “But we also both like you.”
“Are you telling me you paid tens of thousands of dollars just to ask me out?” You don’t know if you should be concerned or flattered.
“You didn’t answer the question.”
“Yes. I would.” You decided to go with flattered.
The two take you on quite the extravagant date. Renting out an amusement park just for their workers and the three of you. It feels odd, allowing yourself to enjoy something as big as this, but they both reassure you that you deserve to be treated in such a way. After all, you are such a hard worker.
It becomes a common occurrence, the men taking it upon themselves to pay for you. You find that you are barely paying for any of your necessary expenses. Finding that Chance and Parker set up to cover your rent. Then they randomly offer you a black card telling you to “go have fun.” Both revel in the shiny nervousness in your eyes as you trail out a ton of questions. None of which they answer.
“Just get whatever you want, sweetheart.” Chance says. “Just as long as it’s legal.”
“And even then, I can easily get you out of trouble.” Parker shoots you a wink, to which Chance shakes his head and groans at.
You don’t use the card at first. Leaving it on the table by your front door. When they realize you haven’t touched it, they will insist. Eventually you start to, but just for bare necessities. Groceries and gas, maybe a sweet treat every so often.
It’s not enough to their liking, so you’re being dragged out on a shopping spree. Your entire wardrobe is being refurbished, and they’re making sure you use the card for it. You’re going to get that expensive dinner, and you’re going to use that card on it. They will not be satisfied until you have spent at least thousands of their money. It’s both nerve wracking and exhilarating. You kind of like giving them that control. They clearly like giving you control over their bank accounts.
Once you finally get more comfortable, the two are ecstatic. Anything and everything is yours. Of course, you’re moving in with them. You can get that journalism job you want, but you know you don’t need it. The freedom allows you to fully put in your passion for your work, and the men love to see you thrive.
Then, there’s the sugar. Again, they don’t necessarily need it from you. Part of them gets off on the fact that you’re using their wealth. However, when you do provide, they are taking everything they can get from you.
Out of the two, Chance is the sweetest. Offering you praise, worshipping your body. Soft kisses and sweet love bites are trailed over your sensitive skin. Going down on you for so long, it’s almost concerning. He loves to please you, and make sure you get everything you deserve. So he will not be satisfied till he knows that you are completely satisfied.
When it’s just the two of you, Chance enjoys his roleplays with you. Having both of you dress up and reenact sexy scenarios. Sometimes Parker joins in, but that’s not really his scene.
Sometimes, Chance will get more pent up. Especially after he has to travel for work. Once he’s finally alone with you, he’s making sure he gets his fill. Absolutely ruining you, pressing you face down on the bed till you’re crying from overstimulation. Oh, but he’s not done with you yet. He will fuck you till he cums dry, then he’ll be back to his sweet and caring self. Kissing you oh so softly as he tells you how good you were for him. Apologizing if he was too rough, knowing damn well he’s going to be doing it again in a few weeks time.
Parker is the tease, sometimes almost too mean with it. He really likes to rub it in your face everything they do for you. Forcing you close to the edge over and over again, asking if you truly think you deserve to cum. It’s only when you are practically screaming as you beg when he’ll finally give you the relief you’re looking for. Then he’ll start it up again, but this time, he’s using his cock inside your desperate hole. He wants to make sure you are a cockdrunk mess that’s fucked absolutely dumb when he’s done with you.
There are times when he is sweet. After particularly rough days, you’ll find him fucking you as you spoon. Parker softly huffing moans and groans as he kisses and bites into the crook of your neck as he fucks you slowly from behind. His fingers working at your sex as he thanks you for being so good to him.
When the two of them fuck you together. You are an absolute goner. Do not expect to be able to walk when they are done with you. It’s almost like a good-cop/bad-cop situation with them. Chance being the sweeter one while Parker teases you. Don’t get it twisted, their roles can easily be swapped. They might even work together to tease you into desperation. Chance’s face between your thighs when he goes down on you. Parker will talk him though it as his hands run over your body, lightly tweaking your nipples. When you get close, Parker stops Chance, making you groan out in frustration. It’s only when you beg that they will finally grant you release.
Parker loves to just sit and watch you and Chance go at it. Fisting his cock to the timing of Chance’s thrusts in and out of your sensitive hole. He’ll edge himself as Chance brings you to your climax over and over. When Chance has fucked you dumb, Parker will take his turn. Making you become a gooey overstimulated mess, only able to moan as the men continue to use your body as they wish.
The two will also make passionate love to you. On days where one or more of you is feeling down, a session of pure lovemaking is in order. Soft caresses and kisses pressed all over each others’ bodies along with praises and confessions. They love it when you tell them you love them. It’s an easy way to get them to finish as their bodies shudder from your words. Chance is more of the sappy lover though, sometimes finding himself crying from the mixture of pleasure and the swelling of his heart with adoration.
Regardless of the type of sex, you all receive lovely aftercare. Sometimes it involves running a bath in the giant tub that can fit the three of you. Other times it’s just soft touches and words of affirmation as you drift off in each other’s arms.