Playing Around
Erotic Couplings Story

Playing Around

by Thomastam 18 min read 4.7 (17,100 views)
dare game secret strip teasing oral big tits play
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Playing Around

For Georgie,

She was so close.

Bella was reaching the edge of the horizon. It was the final push. She had almost crested the hill. Only a few more moments and dawn would flood over her. Her breathing was fast, her body tense, her mouth agape, her hand working overtime as her toes began to curl. And then...

Ring, ring. Ring, ring.

It caught Bella off guard. She stumbled. Her hand slowing as her mind flushed back to reality. She tried to push on, for a few more moments, but the momentum was gone. The bell kept ringing. The horizon faded away, as did the hill, and the faceless man she had pictured in her mind. Her body ached. She was left unsatisfied and annoyed. But she had no one else to blame but herself. She was beaten.

I'll get him back for this

, Bella thought.

Her doorbell continued to ring for a few more moments. She lay in bed, naked and sweaty, her breath slowly steadying. This was her fault; she had asked Charlie to come over when he was back from the gym. She didn't expect him to take so long, so she lay in bed and let her mind, and her fingers, wander. Now, Bella wished he had taken even longer. After a polite amount of time, he rang the doorbell again, and she threw off her covers and threw on a sports bra, a hoodie, some boxers, sweatpants, and mismatched socks. She was sweaty, but he'd be sweaty too, so she didn't care much.

She ran down the stairs, called out to tell her family she's leaving, and leapt through the door into his arms. When they were kids, she used to knock him over with that, but now they were older, he not only expected it, but could handle it. Charlie's arms were wide, catching her midair and swinging her around as they hugged. It had been nearly three years since they last saw each other in person, but their friendship had never died.

Charlie was back home for the summer and Bella had come home for the weekend. For the first time in forever their visits lined up and they were back in their hometown at the same time. Bella had arrived only this morning, but he had been doing odd jobs around town all day, and then wanted to go to the gym, so she had been waiting all day to see him.

After their hug, the lifelong friends made the long journey to his house, right across the street from hers. They had grownup as the only kids on their suburban street, their windows facing each other across the wide road. Their friendship was natural. They weren't the most interesting of people. She was a generic girl, him a typical guy, and that was really it. Sometimes all you need to get close to someone is to just be close by. They also didn't bother making many other friends, since they always had each other. They spent their childhoods watching videos on the internet, playing the old first-person shooter games, and chatting shit. There was nothing more to it.

As they grew older, they didn't necessarily grow apart, the world just took them to different locations. Charlie's parents divorced and he chose to go with his mother, only visiting his father and sisters occasionally, while Bella dropped out of school and went to college early, taking her away from home for most of the year. They kept up with one another on social media, sometimes talking every other day, sometimes every other month, but never falling out of contact. But now, they were back together again, and they were going to make this week last.

They hastily ran up the stairs to the sound of Charlie's dad telling him to take out the bins before sunset. They raced each other into his room. Bella got there first and leapt onto his bed. It was only as she bounced on it that she realised how small it was. Everything in the room seemed smaller, except them. They were adults now, though back together again, they didn't feel like it.

She inspected her old friend for the first time in years as he fell into his old and tattered, yet comfy, swivel chair. Charlie had short curly hair, black as night, and olive skin, freshly tanned from working out in the heat. His sweat gave him a nice sheen. He was much taller than he once was, and far more muscled. Even under his two shirts, she could see his chest heaving underneath it. It was funny to think of her scrawny little best friend as a hunk now.

He'd be my type

, she thought,

if I met him now and not when we were snotty little kids

. All her new friends at college fawned over him when she showed them pictured, but she had never seen him that way, she will never see him that way. He was like a kind of brother.

"Let's go for a classic one. And a classic map. You remember this one?" Charlie asked her, before putting on a voice and saying "Window!" Bella chuckled. To explain the half-a-decade old inside joke would take too long.

He turned on the console and brought out the controllers, sliding right back into the muscle memory of their youths. Bella pulled herself to the edge of the bed to face the huge monitor. It was then that she felt the humidity in the room, the sweat still on her face getting moist. She pulled the bottom of her hoodie up and began to wipe it away. It was then that Charlie held the slightly crappier white controller, keeping the main black one to himself. She wiped the last of the sweat off with one hand while she reached out with the other. Her eyes came up to his, and for a moment she thought he was looking at the controller, but then he blinked and turned away as she dropped the bottom of her hoodie.

Oh, right.

She held back an annoyed scoff. He had grown into a typical man. All she had done was accidentally give him a good look as her toned midriff, but it was enough to throw him off his balance. In a way, it was disappointing, but not surprising. Bella had changed in the years since they last met. She still had her long pristine blonde hair, her clear tawny skin, and her passion for good nails, good lashes, and good makeup, but she had also become a woman. Time had been kind to her. Before, she was a little wider and a lot flatter, now she had curves in all the right places. She had started working out when he did, and they shared their journeys together, though online she could never see where his eyes looked. Bella had become lean; her waist was tight while her glutes were thick, and her breasts were large. She had grown into the very stereotypical blonde that they had made fun of in school.

Charlie booted up the game and they began to play. She quickly realised that her pretty long nails were making it harder to play than when she was a kid, but luckily it seemed Charlie was entirely out of practice, leading to her winning game after game.

"I have an idea," she said after her fourth win in a row, "let's do a dare game."

Charlie groaned. He had always hated them. His ego had gotten the better of him whenever she asked and he agreed to it, only to lose set of games and have to do something embarrassing, like letting her send his crush a text from his phone, or spend an hour in a dog cage, or wear girl's clothes for the whole weekend. Each time, he'd swear off dare games, only to cave the next time she asked. She usually planned her questions to coincide with him winning a game or two, to lull him into a false sense of security. Today, it seems he finally matured, and he rejected the idea outright.

Moments later he won a game by a single kill and lit up like the stupid goofball he is, and asked if they could play the dare game.

"Since you're on a grand winning streak of one," she told him, "I guess I accept. Whoever wins best out of five games gets to dare the other to do anything they want for the rest of the evening."

"And if they fail to complete the task?" he asked her, no doubt thinking of the screaming match they had years ago when he stopped her from sending a text to his crush asking for nudes.

"Then the victor gets to issue an even harsher dare." Bella smiled, certain of her victory, as always, and wondering what humiliating dare she would inflict upon her best friend.

"May I add another rule?" he asked. She raised an eyebrow. "The length of five games is a long time," he continued, "it may get boring. We're adults, let's take this up a notch."

"I'm listening."

"Every single game won," he started, a cute smile crossing his face, "the loser must remove an item of clothing and keep it off for the rest of the evening."

This time Bella did scoff, followed by an incredulous laugh. Charlie only sat back and smiled.

He is like all the other men

, she realised,

and he is thirsty

. It was then that a revelation hit her. When they were kids, nudity was strictly off limits when it came to a dare game, due to Charlie's own rules. Her ideas of humiliating him were sorely reduced after that, but she respected it. Now, he had undone that rule in his horny idiocy. This was not an opportunity she was going to pass up.

The idea came to her head immediately. He had kept her from finishing earlier, albeit accidentally. That was annoying enough to make her want some kind of revenge. Her dare had to make him feel as annoyed and frustrated and embarrassed as she felt in the moment that doorbell rang. She was going to make him take off all his clothes and force him to take the bins out as his father had asked. While everyone else on the street was doing the same at sunset, he would be doing it entirely in the nude. The best thing about this was that this didn't even have to be the dare itself. All she had to do was win enough games to get him to take off enough clothes, and whatever state of undress he was in, he would have to take the bins out like that, because he had to take them out this evening. Bella considered that worth risking him seeking her midriff again. She accepted his rules. Charlie's giddiness was clear in his eyes. She couldn't help but laugh.

But that may have thrown her off balance. She kept giggling to herself and trying to think of more dare ideas that she didn't focus on the game, and his giddiness had turned to a drive she had never seen in him before. He won the next game, by a lot.

Bella sighed, "a deal's a deal." She pulled off one sock.

"Hold on a second. Both socks are one item of clothing."

"Clearly not, they are separate," she told him.

"Shirts, trousers, pairs of socks, accessories. Those are the categories."

Bella was about to argue back when she noticed something. Although he was barefoot, Charlie was wearing several necklaces, a few wristbands, two rings, and he had sunglasses in his pocket. She could win a dozen games and he'd be no more nude than he was now. She thought for a moment.

"Socks are a pair," she agreed, "but so are all accessories."

Charlie mulled it over, then nodded.

"And items of underwear are separate."

He chuckled and nodded again. "If we were at yours, I'd extend an olive branch and wear your old training bra, like that one time we played the dare game."

Bella threw her head back and laughed, remembering his first ever experience with a bra. Forty-eight hours he had to wear that thing, along with a bunch of other girl's clothes. She hadn't told him that girls don't really wear them to bed, but the discomfort was worth it.

With that, she pulled off her other sock and they got back to the game.

This time, Bella locked in. The status quo was restored, and she got twice as many kills as he did. "Come on," she commanded, "off with the overshirt."

Charlie didn't argue, it was the easiest to take off and revealed the least. He wore a tight t-shirt underneath the unbuttoned overshirt. Bella saw no more skin than she had a moment ago, and she was okay with that for now. It was a process. She felt a queer sensation as he threw it off. It was like she had an appetite for his body. Not in a sexual way, it wasn't lust, it was just an eagerness to get him naked, to embarrass him, but she was still wanting him naked, she was still wanting to see that sight. Picturing it in her mind, she couldn't help but feel excited.

I was denied a release earlier,

she told herself,

it's just leftover lust, the pent-up feelings that are still swirling about, it's nothing.

The next game was much closer, but she won it by just two kills. She had tried really hard, long fingernails be damned, and felt exhausted. Bella lay down on the bed as he slowly took his accessories off, one by one. She had a good look at him, the skin on his thick neck as he unhooked his necklace, the wristbands straining against his tense forearms, his fingers sliding back and forth as he twisted the rings off them. Her thoughts fell back to her own fingers, sliding back and forth inside her earlier. Soon enough, the faceless man she daydreamt of slowly became more and more familiar, until a thought brought her back to her senses. It had been gnawing at her at the end of the last game, as she was counting the kills. She had taken her socks off, one of the five games went to him. There were only two games left in this match, and he still had his shirt, trousers, and presumably his underwear on.

"After this dare game, these five games, can we go straight to the next match? So, I can have two dares I can use together, I mean."

He chuckled and asked, "what if I run out of clothes?"

"Nothing," she confessed, "each game after that, I stand to gain nothing but the extra dare at the end, you stand to gain a dare and the removal of my modesty."

Charlie smiled and agreed to her deal. It was a risky idea, Bella knew, but she really wanted to see him... to have his neighbours see him walking down his front lawn entirely in the nude.

The next game did not go as planned. He had lost four games at the start of their session, before the match began, but now he seemed to be getting better. He got a rocket off in through the window of the room she was camping in, right before she was about to headshot a bot. Not only did he get the last kill, but he killed her and beat her by just that one kill.

Bella almost threw the controller in anger. Charlie chuckled as he spun his swivel chair around to face her. "Hoodie or sweatpants?" he asked.

She scowled at him, resisting an annoyed smile. It was hard to get mad at him when he had that dorky look on his face. Bella stood up before him and decided to put on a fake smile. She swayed her hips as she slowly turned around, as if she were a dancer at a strip club. The last glance of Charlie's face made her giggle. He knew she was toying with him in some way, that some trick was coming, but he also could not resist hope and horniness. He was torn. Bella bend forward, her cheeks facing him, as her fingers went under her the strap of her sweatpants and began to pull down, slowly, slowly, and then fast.

"Oh, dammit Bella," he laughed. "Boxers?!"

Loose, baggy, black boxers. It was like she was wearing men's cargo shorts. Yoga pants would have shown off more. She had luckily chosen the least sexy underwear. Bella laughed and pulled her hoodie down, so it also covered her underwear, denying him the satisfaction even more. She sat down on the bed again and leant back on her hands, a coy smile on her face.

Charlie's eyes were still on her lower half. It seemed he still managed to find some satisfaction. Her legs were bare. They were tanned, smooth, and thin. They got thicker by the thighs, but the boxers and hoodie obstructed his view. Regardless, he saw enough. She scoffed and looked away.

An ankle would turn him on

, she thought, pouting.

Bella glanced back at Charlie. He was setting up the next game. Her eyes looked over him, and she noticed a change. For a moment she thought he had his phone in his pocket, but the shape wasn't quite right. Then it hit her.

How long has it been like that?

Bella wondered.

Had my ankle actually turned him on? Or was it just my legs?

Her eyes fixated on the crease in his trousers. It was long, and thick. She had never really thought about his penis before. She had seen it, when they were young and mucking about, but that wasn't sexual, they didn't know anything about that back then, and it looked nothing like it seemed to look now. She began to imagine what it would look like, to simply plan out her dare, of course. For a brief moment, she felt her throat go dry, and another place get wet. Suddenly the game voiceover was telling them to fight, and she was torn from her thoughts and thrown back into the warzone.

Her mind was a mess. No matter how hard she tried to focus, Bella felt almost drunk. She played an abysmal game, only gaining an atrocious third of the kills Charlie got. It was only after the end card came up that she realised the gravity of her situation. He had beaten her, not just to the game, but the whole first match. She felt the sweat turn to ice on her skin.

"Hoodie, or boxers?" he asked. After a moment, he cocked his head, seeing Bella's reaction, and then he leaned in and made a third option. "Or give up?"

She was taken aback by that. "What?"

"If you don't want to. If you feel we've gone too far. If you want to step back, put our clothes back on, and play games without any dares, or do something else, we can do that."

It should have been tempting. It was kind, thoughtful even. As a kid, he wouldn't have offered her that, she knew. This older Charlie, this hunkier Charlie, was a kinder Charlie too. That added to the queer feeling. But atop all of that, another feeling lingered. She had never been dared before, at least not like this, while he had faced dozens of her ruthless dares before. If Bella backed out after one, what would that say about her? Even if Charlie took this to his grave, it would still be more humiliating than any dare could be.

Fuck it

. Bella would take whatever he threw at her. And they will continue to play, into match two, and this time she will win, and he will be humiliated in her great comeback.

She stood up before him, grabbed the hem of her hoodie, and pulled it off in one clean motion. Charlie was still leaning in. Standing he was a foot or so taller than her, but with him sitting and her standing, his head was facing right at her chest. His eyes inspected her sports bra. She expected him to go wide-eyed, to start shaking, to maybe even hyperventilate, but he didn't. Instead, Charlie studied her figure with calm eyes. They danced over the curves of her waist, down to her thick hips before they disappeared under her boxers, and back up her side to the bands of her beige sports bra. They glided over her neckline, to her shoulders, and then up to her face. He smiled at her, it wasn't a creepy one, or even a goofy one. He seemed... content.

"Dare me." Bella said.

Charlie leaned back on his swivel chair and thought about it. For a moment, Bella feared he was going to skip this faux foreplay and dare her to go nude or do something sexual. She did not want that. But, without either of them speaking their wishes, he seemed to come to a kind of compromise.

"I dare you to sit on my lap."

"Excuse me?"

"Get up here, on the swivel chair, and sit on my lap. Kneel with your legs between my hips and the armrests, and your face towards my face."

Bella laughed and turned away. She felt her cheeks flush. "Cowgirl, you mean?"

"Except you get to keep your current clothes on. Until I win again."

"Fat chance."

"To the dare or the me winning again?"

Bella glared at him, but a smile betrayed her thoughts. It was bold, and it was a little funny. When they fought as kids, which was a lot, she would often get him into that position. It wasn't sexual then, of course, it was just the easiest way to dominate someone, to hold their arms and legs down.

I fear I might have awoken something in him back then

, she thought. "So," she said, "I sit on your lap, all cosy like, and we play another match?"

"That's it. For the rest of the evening, we simply sit close to one another, just like that. If you get off, that's the dare broken, and you know the rules."

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