Tyler’s Game (str8, MF, Mdom, game/bet – 2.778 words)

Author’s note: I primarily post elsewhere – details in comments – but some followers suggested that r/sexystories might enjoy some of my stuff. Here’s one I hope works for this group. :-)

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**Tyler’s Game**
by All These Roadworks (2019).

Tyler had a competitive streak a mile wide. She was a smart-ass, and she hated to lose, and it got her into trouble. For instance, when her cousin Piers visited her in the week after her birthday.

“I got you a late present,” said Piers, handing her a small cardboard box. On the front it said, “Girl Challenge!” in big letters, and then, “No girl has ever won!” in smaller letters below.

“What is this?” she asked.

“So it’s designed for a couple of girls to play together, or you play with a boy and you make a bet,” said Piers. “Then the other person draws cards for you from the box. Each card has a challenge on it. You do two of the “Easy” challenges, two of the “Medium” challenges, then one of the “Hard” challenges, and if you complete all five, you win. They’re supposed to be easy individually, but they add up to become hard.”

“Okay,” said Tyler. “I bet I can do it, though. So if I win – um, I guess you have to buy me another present as well?”

“Sure,” laughed Piers. “You want to play?”

“Definitely,” said Tyler. “What’s the first challenge?”

Piers drew an “easy” card from the box. “Go find some clothes pegs. You need to attach a clothes peg to every item of clothing you’re wearing, but you need to keep your hands behind your head the whole time. You get to ask one favour from me, which can’t be to attach any of the pegs.”

“That’s an ‘easy’ one?” she said, wrinkling her nose unhappily.

“What, can’t you do it?” he said, grinning.

She frowned. “Fuck you, of course I can.” She ran out into the laundry, and came back with a handful of clothes pegs. Placing her hands behind her heads, she picked up the pegs one by one in her teeth, and carefully attached one to the cleavage of her dress, the hem of her skirt, and the strap of each of her high heels.

“And your underwear,” Piers said.

“Seriously?” Tyler complained. She sighed, pick up another peg in her mouth, and managed to hook it onto her bra strap. Then she looked down at her groin in dismay.

“Giving up already?” asked Piers.

“No,” said Tyler quickly. “I get one favour, right? So could you… um… take my panties off and hold them up so I can peg them?” She was blushing, but trying to pretend she wasn’t.

This was already going better than Piers had hoped. He knelt, lifted her skirt, and slowly peeled her pink satin panties down her legs, revealing her pretty shaved cunt. Tyler was blushing madly, and obviously wanted to cover herself or clamp her legs together, but her hands were stuck behind her head, and he couldn’t remove the panties if she didn’t keep her thighs parted. She muttered something, but it was unintelligible past the peg she had picked up with her mouth.

Finally, he had the panties off, and held them for her, and she clipped the peg onto the waistband. Then he knelt and slowly pulled them back up. He gave them an extra tug “accidentally” at the end, pulling the crotch between her labia in a lewd camel toe, and making the rear vanish between her butt cheeks. Tyler gasped, and clearly wanted to adjust herself, but also didn’t want to give him the satisfaction, so pretended nothing was wrong.

“What’s next?” she asked.

“Easy challenge two,” he said. “We should put down a plastic sheet for this.” (Which they did, finding a clean one in the garage.) He passed Tyler a can of whipped cream. “We put a blindfold on you, and you have to depress the spray button for ten seconds while waving your arm around, and then when I take the blindfold off, you have to lick up everything you’ve sprayed.”

“These challenges are weird,” said Tyler dubiously.

“Probably why no girl has ever passed them,” said Piers. “Girls are pretty lazy like that.”

“You ass,” said Tyler angrily. “Give me the can and the blindfold.”

He blindfolded her, gave her the can, and started a countdown. On the count of one, she started spraying – and he immediately ran to the next room, where she couldn’t hear, and used an identical can to spray whipped cream on his mouth, neck, and an extra helping on his crotch. He ran back in the room just as Tyler’s ten seconds were finishing.

He took the blindfold off and let her look around. She had sprayed whipped cream on the floor, and some of the walls and furniture. She’d also somehow managed to get some on her own chest, and it was dripping down into her cleavage. She looked at him, saw the whipped cream on him, and blushed.

“That’s quite an aim you have there,” said Piers. He looked at his crotch. “Look, it’s okay if you want to forfeit…”

“I’m not forfeiting,” insisted Tyler. She looked down at her tits, and tried to lick the cream off them. She couldn’t quite reach. Blushing, she pulled her breasts out of her top, trying to cover the nipples with her hands, and lifted them to her mouth, extending her tongue and licking each one clean in turn. Piers felt his cock stiffening again. When she was done, she put her tits back in her dress, and went around the room licking up the other cream.

Finally, there was just him. She came towards him, blushing, and leaned forward and began licking his neck. It was exquisite. He could smell her hair, and feel her breasts brushing against his chest. She licked all over his neck, and then moved up to lick at the cream on his mouth. Her tongue occasionally went between his lips. Only half done, she had to pull away, breathing heavily, her face flushed, and when she leaned in again, he leaned a little too, and suddenly they were kissing. She didn’t pull away for nearly twenty seconds, before finally licking up the last cream on his chin and stepping back again.

That left only his crotch. “Tyler…” started Piers.

“I’m not quitting,” said Tyler, and knelt before him, and began to lick at his hard cock through the thin fabric of his pants. She pressed her mouth hard against his dick, and he felt lucky he didn’t cum then and there. For long minutes she worked at his crotch, pushing his cock back and forward with her tongue, until all the cream was gone. Then she stood, face bright red.

“There,” she said. “What’s next?”

“Medium challenge one,” he said, and read the card. “Do a handstand for five minutes, no matter what happens.”

“That’s easier than the easy ones!” she exclaimed, and immediately went to the wall, put her hands on the ground, and raised her legs up into a handstand. Her shirt immediately fell downwards, revealing her bra-supported tits, and her skirt fell to show her panties, still wedged in a camel toe.

“No matter what happens, remember,” he warned her. He took his phone and started a five-minute timer. Then he tickled the soles of her feet.

“I’m not ticklish!” she said, a tone of triumph in her voice. “And you’re not allowed to just push me over, right?”

“I don’t think so,” he said.

“Then do your worst,” said Tyler.

“My worst?” he said, an evil note in his voice. He reached down and lightly ran a finger over the cleft of her pussy. She immediately squealed.

“Piers!” she shrieked. “Stop!”

“I absolutely will if you stop doing a handstand,” he told her. “But while you’re still handstanding, I assume you’re consenting.”

She didn’t stop the handstand. “I’ll get you for this,” she threatened. But her legs were still parted and her cunt was still pointed upwards.

He tickled her cunt lips again – then reached down, plucked the crotch of her panties, and moved it to one side, revealing her pussy completely. As he had suspected, it was quite wet.

“Piers!” Tyler said again. “You pervert.”

“Just admit defeat,” he told her.

There was no reply from her, so he pushed a finger into her fuckhole.

She gasped, and her body trembled. He pumped it in and out of her a few times. She moaned – but stayed in the handstand.

Piers laughed, withdrew his hand – and then slapped her pussy hard – one, two, three times.

She shrieked again, clamped her legs closed to protect herself, immediately began to wobble, and reluctantly spread them again. As soon as she did, he leaned down, pressed his face into her wet cunt, and began to lick.

She made a moaning, choking sound. Her pussy was sopping wet, and it tasted amazing. He chewed on her clit and pushed his tongue down her fuckhole. Her moaning got louder and louder – until suddenly he pulled away, and once again started slapping her cunt – ten times, this time, and hard. She yowled and screeched, but when he was done he started licking again and she quietened.

He went on like this, interchangeably beating her pussy and licking it, until the five-minute alarm sounded. He backed away, and she stayed in the handstand for a full further minute, hoping he might come back and keep licking, before finally, disappointedly, letting herself fall forward, landing on her knees in a crawling position, her still-exposed pussy pointing upwards lewdly at him. She stayed like that for a minute, then stood. He noted she had not bothered to adjust her panties.

“Piers,” she said, in an unsteady voice.

“We can continue what we were just doing if you want to forfeit,” Piers said.

Tyler looked longingly at his crotch, and didn’t answer for a minute, before finally saying, in a voice like she was trying to convince herself, “No. I’m not forfeiting.” And then, “Gross, no, you’re my cousin, you pervert.”

“Medium challenge two, then,” said Piers. “Go get me a hairbrush.”

Tyler ran off, and came back with a wooden one. As she handed it to him, she was idly rubbing her ass through her dress.

“I’m not spanking you with it,” said Piers.

“Oh,” said Tyler. She sounded disappointed.

“So the challenge is this. You have to get that hairbrush into the bathroom. But once it’s in there, it can’t be touching any of the walls, ceiling, floor, or any item of furniture. It can’t be held in the hands or mouth of a person or balanced on any part of them. In fact, no person can be standing or sitting on any part of the bathroom, or touching the floor. In addition, remember those pegs we put on your clothes back in easy challenge one? They can’t leave this room, and you can’t take them off your clothing. If you succeed, another player – me, I suppose – needs to take photographic evidence.”

“That’s complicated,” said Tyler.

“Want to forfeit?” asked Piers.

She looked at his cock again, but said, “No. I can do this.”

“Okay,” he said. “Go.”

She paused for a while, thinking. Then she blushed, and he knew she had a solution.

Moving quickly, not letting herself think, she started stripping, until she was naked, all her clothes – and their pegs – ling on the lounge room floor. She looked divine in this nude state, her nipples perky with arousal, her face flushed, and her pussy wet. She took the hairbrush from him, not meeting his eyes, and ran to the bathroom. He followed.

Inside, he found her solution. She was lying on her back on the edge of the bathtub – neither standing, nor sitting, nor touching the floor. She had her legs raised, and spread, and the hairbrush was sticking out of her pussy, its handle having been pushed up her slut-tunnel. There was a look of victory on her face.

“Do I win?” she asked, smugly.

“You pass the challenge,” he told her. “Well, once we have the photographic evidence.” He took out his phone and aimed it at her.

She was suddenly nervous. “Wait, you’re taking pictures?” she asked.

“Unless you forfeit,” he said. “Spread your legs wide. Let me see where you’ve inserted the hairbrush.”

“Piers…” she said, feeling genuinely a little scared and vulnerable.

“Do you forfeit?” he asked, more sternly.

“No,” she said, and spread her legs obediently. He took more than a dozen photos, filling his camera gallery with images of his cousin, nude and aroused with a hairbrush shoved in her twat.

“Okay, *now* you’ve passed the challenge,” he said, finally.

“Thank Christ,” said Tyler, sitting up and removing the hairbrush. “One to go, right?”

“One to go,” he said. He extracted the “hard” challenge and showed it to her. It was a sealed envelope. On the front it said, “No girl has ever won!” On the back it said, “Double or nothing? Do you feel like you will pass the last challenge? Why don’t you raise the stakes?”

“Of course I’m going to pass,” said Tyler. “Okay. Raised stakes. If I win, you have to buy me a piece of jewellery worth at least two thousand dollars. I know you can afford it, with your IT job.”

Piers laughed. “Okay, but if I win, you have to be my sex slave for a month.”

“Gross, Piers,” she said, but he noticed she flushed, and she clamped her legs together tightly, and her nipples stiffened.

“No girl has ever won, it says,” said Piers. “Are you sure?”

“Like I’m going to fucking fail,” said Tyler. “Whatever it says. Sure, your sex slave for a month if I fail, pretty jewellery if I win. Open the fucking envelope.”

He smiled, opened it, read the card inside, and then held it up for Tyler to read. She felt her heart sink.

It read:

“DON’T BE A SLUT. Let another player put a finger in your pussy. If it comes out wet, or if any player has seen your cunt be wet during an earlier challenge, you fail. Otherwise, you succeed.”

And then, in smug brackets, “No girl has ever won.”

Piers stepped forward, and sunk his finger into her fuckhole. It was flooded with slutty arousal. Tyler looked up at him despairingly.

He took his cousin’s hand and moved it to her pussy. “Masturbate,” he told her, and she did. Then he grabbed her hair, pulled her from the bath, and pushed her into a kneeling position on the bathroom floor. He took out his cock from his pants, and guided his cousin’s head down to it. She started sucking obediently, defeated.

“Don’t worry,” he told her. “I got you a second present anyway. It’s the next game up from this. It’s called ‘Whore Challenge’ and it starts from the assumption that girls who play are willing to fuck people and degrade themselves from sex. The easy challenges are things like not cleaning cum off your face for a day while doing things in public, or having a naked 69 with another girl in public. The medium are things like getting Google to offer “slut” or “whore” as an autocomplete when people type your name on the internet, or getting three different men to rape you on the same night. Do you want to play that one, Tyler?”

She shook her head vehemently, no, jerking his cock from side to side as she did as it was still in her mouth. It felt wonderful, and he laughed.

“That was a rhetorical question, Tyler,” he said. “You’re my sex slave now, and your opinion doesn’t matter, does it? Answer honestly.”

She kept sucking for a second, then wiggled his cock side to side again in a “No.” She learned quickly.

“One last question, Tyler. You’re my cousin and I love you and I’m not actually going to make you do anything you don’t want to do. If this has all gone too far, you can back out now, and we’ll call it quits. But if you don’t, I really am going to use you to fill some twisted fantasies, you know. So how about it, Tyler – do you want to forfeit?”

She looked up at him. She was nude, kneeling, masturbating, blushing, still sucking his cock. But a fire of defiant competition remained in her eyes, and he thought that she was smiling, as much as she could around a mouthful of dick. And slowly, deliberately, making sure he understood, she wiggled his cock one final time. And he immediately ejaculated down his cousin’s throat, because he knew the meaning of that message:

“No.”

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