by Kinley Grey
Playing to Win
Kinley Grey
Table of Contents
The Drive – Dan
Returning the Favor – Carter
Wear Nothing – Dan
Back to Nature – Carter
Bacon and Pussy – Dan
Car Trouble – Dan
The Photo Shoot – Carter
The Drive (Again) - Dan
Girls’ Night In - Carter
What Dan Saw – Dan
A Few Small Repairs – Carter
Family Reunion – Carter
The Luckiest Bastard - Dan
Threesome - Carter
Afterglow – Carter
Game Over - Stacy
Shades of Grey, The Art of Kinley Grey
About the Author/Artist
The Drive – Dan
Stacy sat in the passenger seat of the RV, long legs propped up on the dashboard, looking over the map her step-sister had given them. “I think that's the turn up there.” She pointed at an unpaved road, practically a dirt path, and he slowed down and made the turn.
Dan surveyed the remote landscape through the windows. The words, “weekend getaway” didn't typically bring to mind an RV in the middle of nowhere, but he reminded himself that he’d have Carter all to himself for the weekend. Well worth the drive, he thought.
“Have you ever been out here?” he asked.
“Not since I was a kid. We used to go on family camping trips here, but that was a long time ago.”
Dan put a hand on her bare thigh, enjoying the smooth feel of it under his fingers. “It was nice of Stacy to set this all up.”
“Yeah it was. I wonder why she did it.”
“I don't know,” he said, though he actually did know. Stacy said that Carter was working too hard, and they needed to help her relax and have a little fun.
Secretly, Dan agreed with her. Carter had been working a lot of hours at the bank after a recent promotion, and things in the bedroom had become routine. Even a little boring, if he was honest.
He glanced at the small stack of envelopes in the space between the seats. Stacy had told him they were part of a game that would make this the best weekend of his life. He didn’t know about that, but he hoped Carter would play along.
If anyone could bring Carter around it was her step-sister. The girls were as close as if they’d been related by blood, although they couldn’t have been more different. Stacy was a vixen, the life of any party, while Carter was sweet and shy. They thought of each other as sisters and rarely told people they were only related by marriage.
Carter put away the map and picked up a stack of envelopes. They were sealed and one was labeled, “Rules.” The others were numbered one through four.
“What do you think?” she asked. “Should we open the first one now? Stacy said we should start the game as soon as possible.”
Dan glanced at the envelopes and shrugged. “What do you think it is? Trivia or something? The loser has to clean up after dinner?”
Carter shook her head, “No, she said it's more like truth or dare, something special for our weekend. She said she didn't think I'd be able to finish it though.” Carter snorted.
He hid a grin. The sisters were competitive, and he was sure that Stacy had delivered that challenge on purpose.
“Do you think it’ll be disgusting like that show Fear Factor? You don’t think she’ll make us eat bugs do you?”
Dan had his eyes on the road but he felt her shudder through the hand he still had on her leg. “I'll play if you want to, but we don't have to,” he said.
“We do have to.” she said, tightening her jaw. “I'm going to win this game of hers.” To his surprise, Carter was already ripping into the first envelope. She read the rules to him:
Every envelope contains a challenge. You must complete the challenges in order. Once you read a challenge you must complete it within one hour.
Carter said, “Doesn’t sound too hard. Want to play?”
Dan glanced at her. Her cheeks were flushed and her eyes sparkled. She loved a good game, especially when she played against her sister.
“Sure, I'll play.”
“All right,” she said, “I'm going to open the first one now. What time is it?”
Dan glanced at the clock, “5:30.”
“We've got 'til 6:30 then. I wonder what our first challenge will be.”
Dan could hear the smile in her voice and hoped the first challenge was a good one.
She unfolded the note and read it, then went deathly quiet. Dan glanced over at Carter, who stared at the paper in her hand.
He said, “The clock's ticking, what's it going to be? Do we need to pull over and look for something squishy with a lot of legs?”
When Carter didn't laugh he looked at her again. She was still looking at the paper she held.
Dan patted her leg, “Listen hon, whatever it is, we don't have to play. It's just a silly game. We can tell Stacy we didn't get around to it.”
Carter said in a shaky voice, “No, I'll do it, you'll just have to tell me how.”
“How to what?” asked Dan.
Carter held the paper over to him and he glanced down, reading it in a single glance:
1. Go down on the driver.
Dan's cock began to harden the moment he read the words. This promised to be interesting, considering Carter had never blown him. He joked to break the silence. “I'm sure glad I offered to drive first.” He hadn't offered though. Stacy had handed him the keys and told him to enjoy himself.
Carter gave a hesitant laugh, but she did laugh. That was a positive sign. He went on. “You don't have to do this, Carter. We can still have a nice weeke...”
Carter's hand on his cock cut him off mid-word. She'd unbuckled her seatbelt and was kneeling next to his seat. She touched the hard length of him through his jeans and said, “That can't be comfortable.” Then she undid his fly. The head of his cock was just visible above the elastic of his boxers and she leaned forward and gave it a tentative lick.
The RV veered as the electricity of her touch jolted through him.
“I hope this thing is insured,” he tried to joke lightly, but his voice sounded thick in his throat. Carter had pulled his boxers down to reveal his full shaft and she was close enough he could feel her hot breath on him.
He wanted to see her take him in her mouth. He glanced down and noticed her hesitate. She looked up at him.
“I'm really not sure how to do this,” she said. “How do I start?”
Dan imagined her mouth on him and said the first thing that came to mind. “Imagine it's a hot day and my cock is your favorite flavor of popsicle.”
“You're melting,” said Carter, eyeing his swollen cockhead, where a bead of pre-cum blossomed at the slit and dripped down over the crest. Carter caught the drip on her tongue, slowly licking her way back to the tip.
Dan groaned as she traced her path again, then lowered her face to the base of his erection. He felt her hot tongue at the root of his cock and he shuddered as she gave him a long lick. She did it again, this time moving her tongue back and forth as she licked from base to head.
“Now what?” she asked.
He had slowed the RV until they were barely moving, just inching their way down the road. He ached to have her mouth back on him, and his cock strained upwards towards her. “It's a hot day. You'll have to do more than just lick.”
As he watched, she looked up at him and closed her lips over the head of his cock, suckling him. His eyes drifted shut at the pure bliss of it, then snapped open as he heard the sound of tires drifting off the road.
He straightened out the RV and risked
another glance. Carter's sweet mouth moved up and down along the length of him and he shivered as he felt her teeth. “Careful,” he warned, but he didn't care. It was the first time she'd ever taken him in her mouth and he wasn't going to complain about anything.
“It's okay to use your hands,” he said. She instantly took hold of the base of his cock with one hand and moved her head up and down, taking as much of him in her mouth as she could, while squeezing and rubbing the rest of his length with her hand.
Dan trembled and gasped as he felt the orgasm building inside him. He moved his hips in time to her rhythm and with one hand reached into her shirt and massaged her breast. Her teeth nipped him again, as she increased the pressure of her lips around him.
His balls clenched up tightly, then sweetly released as he filled her mouth with his creamy load. Carter gagged and pulled off him, taking the next spurts in the face. She looked adorable with his cum all over her face. She leaned down and gave him one last caress with her tongue, making a show of licking up his cum and swallowing it.
She raised her wet face to him again and to his surprise she said, “Mmmm... cherry.”
Returning the Favor – Carter
Carter sat with the envelopes spread on the table in front of her. They'd found the campsite easily, and had just eaten dinner. Dan was doing the dishes, and when he finished they were going to open another envelope.
Carter mentally replayed the blowjob she'd given Dan in the car. She'd never blown a guy before. Stacy had shown her how once with a banana. She'd laughed at the time but thought it sounded kind of gross and unsanitary. She doubted she ever would have offered to do it without her sister's suggestion.
Now that she'd tried it though, she'd like to do it again. Dan's cock had been so silky yet so hard in her mouth. She licked her lips, remembering the taste of him. Stacy had said a guy would do anything for a blowjob and now Carter believed her.
Dan was almost finished with the dishes and Carter glanced down at the envelopes again. She wondered what might be in the next one. Maybe a role reversal? She raised a cool hand to her warm cheeks. She had never let Dan lick her there, though he'd tried. It just seemed... wrong somehow.
Now as she looked down at her body, her nipples tightened through the thin fabric of her nightie and she thought that maybe, just maybe, it would be kind of nice to be licked and kissed like that.
Carter glanced at Dan and almost laughed. “You in a hurry there?” she teased. Dan was rinsing dishes and putting them away wet. A look at his pants told her he was more than ready to see what was in the next envelope.
With a clatter of dishes, the final plate was put away and Dan joined her at the table. “I'd say you're the one that should be in a hurry. It's your turn now.”
Carter tore open the envelope, then froze as Dan leaned over and began to lick and suck at her puckered nipples through the cloth of her nightgown. He broke away for a moment to say, “You go on and read it, I'm just getting a headstart.”
Carter put a hand on Dan's shoulders, feeling his tight muscles as he suckled first one nipple, then the other through the sheer fabric. His tongue flicked repeatedly across the sensitive area and she arched towards him with a soft moan.
His lips were hot against her ribs and stomach as he trailed wet kisses down her length. Her nightgown only reached the top of her thighs and Dan had already lifted it and started kissing along the elastic of her panties.
Dan tugged at them with his teeth and a wave of moisture flooded out of her as he lifted her ass from the seat and slid them down. Then he pulled her hips to the end of the chair and buried his face between her legs.
Carter's eyes flew open as Dan's tongue entered her cleft, seeking out the throbbing button of pleasure at its core. He found it and circled it with his tongue, making her catch her breath and strain towards him. She caught sight of the paper in her hand and instantly read the next challenge.
“Wait.” she said, more weakly than she'd intended.
Dan paused, his mouth still on her sex, eyes meeting hers. They were frozen like that only a moment, then Dan closed his lips around her clit and sucked insistently. She melted into the floor. The paper forgotten, she closed her eyes and abandoned herself.
Dan flicked his tongue more firmly against her nub then pushed her legs wider with his hands. She spread them at his touch, and his fingers slipped easily into her pussy and begin to thrust in and out.
“Oh, please,” she cried softly, head thrown back and riding the waves of pleasure with each movement of his big hands. He licked faster and faster, pushing his fingers more deeply and firmly inside her, until she plunged over the edge of pleasure and came hard, shuddering and gasping her release.
Carter sat weakly in her seat, still panting softly, body trembling. Her hand shook as Dan took the paper from her. Without looking at it he leaned in and kissed her. She could smell her sex on his lips; she could taste it. His cock bulged obscenely in his pants just inches from her face and she considered giving him another blowjob, but she ached to have him inside her.
Dan read the next challenge out loud:
2. Have sex outside. Wear nothing.
“You little minx,” Dan said. “You knew what it said and you let me keep going.”
“I tried to stop you.” Carter giggled.
“Yeah, you tried real hard, didn't you?” Dan smiled too, teasing her. Carter couldn't resist any longer, and reached over and squeezed the bulge in his pants.
“Not as hard as you,” she said, and then walked towards the door of the RV, looking over her shoulder and indicating for him to follow.
Wear Nothing – Dan
Dan was sure he was harder than he'd ever been in his life, watching Carter practically prance ahead of him to the door. What had come over her? She had never been like this with him. She was doing things with him he'd never dreamed she'd agree to, and seemed to be having the time of her life. When they got back on Monday he owed Stacy big-time for setting this whole thing up.
As he walked by the table Dan glanced at the pile of sealed envelopes and wondered about the rest of the challenges. He caught a glimpse of Carter's bare ass as her nightgown fluttered in the breeze from the door. He imagined turning her over his knee and spanking her until her bottom glowed red and his hand burned.
Dan's blood pounded through his body. His cock ached at the mental image of Carter helpless and under his control. He quickly stripped off his shirt and pants, then stepped out of the RV. There she was, standing in the moonlight and shivering.
Her arms were crossed over her breasts and the cool air of the desert played with the hem of her nightgown, giving him tantalizing glimpses of her pussy. She must have shaved for the trip, because she was smooth and hairless.
As he reached to pull the nightgown over her head, he sensed her hesitation.
“Someone might see me,” she worried.
“Wear nothing.” he whispered in her ear.
The words were like magic. She raised her arms and in a moment he'd tossed her nightgown aside. He massaged her breasts, squeezing them tightly. Then his mouth was on them, sucking and biting and tasting. Carter gasped and cried out, but didn't pull away.
Back to Nature – Carter
Carter was in a paradox of pleasure. She was completely naked outside on a moonlit night. They were pulled just off to the side of the road and anyone driving by would be able to see her, yet all she could think of was the mouth on her breasts, sucking and nipping at them until she cried out in pain, wanting more. A gust of wind brought sand stinging across her back and she caught her breath sharply.
At the sound, Dan's eyes darkened and he ground his hips into her. His erection was against her stomach, and she caught sight of the shadowy length of him in the moonlight. Reaching down, she held him firmly in her hand and began to rub his head firmly against her clit, moaning as each stroke brought a wave of pleasure.
She floated away into the night on a sea of bliss. Dan's hands found her back, an
d traveled the length of her spine, grains of sand rough and scratchy beneath his fingers. He massaged her ass, spread her cheeks and fingered her tight opening.
Carter was back in her body with a gasp, fighting to get away from this intrusion. “Easy there,” Dan's voice whispered in her ear as he moved his hands to cup her bottom. He lifted her to his waist and held her suspended for one long moment, his cock at the entrance to her dark, wet pussy. Then he brought her down swiftly, impaling her on his full length.
She cried out, voice lost in the darkness as Dan sheathed himself in her, filling her. The moonlight danced across them as she rode Dan like a creature of the night. He rocked and pumped beneath her, each thrust bringing her closer to her limits, until her climax crashed over her and she screamed his name into the darkness.
Awash with pleasure and wonder, she opened her eyes and met Dan's hungry gaze. She could feel him teetering on the edge of his own release, yet she sensed his unmet longing.
“Fuck me hard,” she whispered to him, and Dan groaned. He carefully lowered her to the ground and laid her down. The gritty sand and rocks dug into her back and she bit back a yelp. The sound seemed to drive Dan mad.
He parted her folds and urgently drove into her. Carter watched his face as he pulled out until only his tip remained in her, then braced herself for another thrust. She couldn't stop her cry as he buried his length in her, the force of it pushing her roughly across the ground. Dan's eyes glittered in the darkness, and she knew what he wanted: her pleasure and her pain. His control was at the breaking point, but still he waited.