"We use me, no way his sister would make him hard." Emily teased with a matching grin.
"You are kidding right?" Tyler said a little taken aback.
The late afternoon sun bathed the backyard in a golden haze, its rays glinting off the pool's surface like scattered diamonds. The air buzzed with the soft hum of cicadas and the occasional splash of water. A small Bluetooth speaker played a summer playlist, the easy rhythm of the music drifting lazily through the air. On the patio, Tyler sat with his best friend John chatting. Their sisters, Emily and Chloe sat a little away and lounged in various stages of summer pool party relaxation.
Emily, Tyler's sister, lay sprawled on a pool recliner, the sun catching on her lightly damp skin. She had her arms behind her head and one knee lifted. Her swimsuit, to his disappointment, was a daring red bikini with thin straps and high-cut sides. The thin fabric over her breasts barely covered her nipples. Her thong bottoms were just as bad. More thin fabric that didn't cover enough. Her knee dropped to the side giving him a clear view, on either side of the strip of cloth he could see the sides of her pussy. It was something chosen to make a statement.
Her friend Chloe, John's sister, wasn't wearing much more, not that he minded. She floated nearby on a flamingo-shaped pool float, her neon yellow bikini leaving just as little to the imagination. Her laughter was bright, frequent, and contagious. Tyler nursed a cold soda, legs stretched out, sunglasses shading his eyes. He watched his sister and her friend banter, a small smirk on his face. John perched at the edge of the pool with his feet in the water, was the picture of mellow energy, sipping his drink, and occasionally tossing a pool noodle at Chloe to make her yelp. Now that Tyler thought about it, John's suit didn't cover much either. A red speedo that rode high on his ass, maybe intentionally so, and didn't do much to disguise the outline of his cock.
Tyler leaned forward and said with a grin, “You two sure these suits weren’t made for Instagram and not actual swimming?”
“Why? Feeling shy around all this skin, Ty?” Chloe teased.
John chuckled, “Careful, man. You’re one comment away from sounding like a dad on vacation.”
Emily sighed and said, “Just say you’re turned on and move on.”
Tyler held up both hands, laughing. “I’m just saying, bikinis like that wouldn't be legal on public beaches.”
Emily giggled, "Well we would take them off if you wouldn't get too hard to walk."
Tyler leaned back in his chair, a cocky smirk in place. "No way, I get hard when I want to." The other three laughed openly at him. "Really though, Chloe could be naked in my lap and I wouldn't get hard if I didn't want to."
"I want you to prove that," John said with a laugh as both girls moved to the chairs next to them.
"Sure thing," Tyler said, interested in the idea of getting Chloe naked.
"You'll fail. You already want to bang Chloe." Emily said with a grin. "I know, let's give you the best shot at winning."
"What do you have in mind?" Chloe asked with a wicked grin.
"We use me, no way his sister would make him hard." Emily teased with a matching grin.
"You are kidding right?" Tyler said a little taken aback.
"Hey man, you said 'any woman' remember?" John teased. "Plus I would love to see your sis out of that suit." Emily giggled.
"I know," Chloe added, "if you can last 3 minutes without getting hard then after I'll give you a blowjob."
Tyler considered that for a moment. This might be worth seeing his sister naked, not that it would be that bad. He had to admit his sister had a hot body. Maybe he could even work this into Chloe even having sex with him. "Five minutes," he said boastfully, "and my reward is fucking you."
"Deal." Chloe and Emily said in unison.
"This will be so funny with you fail man." John laughed. "So ladies, what are his rules? I'm thinking she lays back on the chair and he has to be between her legs in fucking position."
The girls giggled and nodded. Emily laid back and raised her knees, letting them drop to the side to make room for her brother. Tyler, feeling a bit weirded out by what he was about to do, moved toward her.
"Nope," Chloe said with a giggle as everyone looked at her. "Drop those trunks, we need to see that cock to make sure it isn't hard. Oh, and you lose if it is already."
Tyler rolled his eyes and let his trunks fall. He was glad his cock was soft and he knelt between his sister's legs. Emily smiled at him, clearly enjoying it as John grabbed his phone to time it.
"Hold on," Emily said, "He said naked." She reached up and untied the straps of her top. She pulled it off and tossed it away. Then she untied her bottoms and, lifting her butt, also pulled it off.
Tyler swallowed hard, he could tell this wouldn't be easy as John started the timer. He let his eyes wander over Emily's body. He had always wondered how she looked naked. He had even tried to peak a few times growing up, now he had 5 minutes to look. Her nipples were smaller than he expected and her clean-shaven pussy was a lot more inviting than he wished.
John called out the first minute. Chloe kept taunting him, telling him how he should just let himself go and fuck Emily. He thought about that for a moment as he watched Emily blush. She didn't seem against the idea and he had to admit, if he got hard he could be in her before she could stop him. The second minute was called out. He shook himself mentally. First, this was his sister. Second, he would never just go in, unless the woman wanted it.
His eyes trailed across her perky breasts and then down her firm stomach, noting the sexy way the water from the pool beaded on her skin, stopping at her pussy again. He could swear she was wet there. Not from the pool but from desire. The third minute was called out and Emily ran one hand down her belly and for just a moment rubbed her clit.
"Sorry," She giggled with a soft deep breath, "Just a little itch." She stopped as soon as she started and let her hand fall away but the damage had been done. He was close to losing and Chloe saw.
"OH! It's starting to get stiff! Come on Tyler! Just two more minutes and you can let it get hard for me to suck." Chloe said. Emily moved closer and he could feel the heat from her pussy. And that was all it took. Between seeing a sexy naked woman in front of him and the promise of a blow job, it was too much. Just as the fourth minute was called out his cock slowly, resolutely, began to stiffen and rise.
"Oh, that's a fail," Emily said.
"Dam bro, you did better than I would with Chloe there," John said setting down his phone. Tyler wondered why he would suggest Chloe instead of Emily.
"What will we do with him?" Chloe teased.
"Make him go into the front yard naked?" John suggested.
"His punishment had to fit the fail." Emily teased as she held him in place so his hard cock was still inches from her, now clearly wet and needy, pussy.
"Make him let me sit in his lap naked for the rest of the night but he can't touch me or his cock?" Chloe offered.
"Come on guys it isn't that big of a deal," Tyler said, trying to avoid thinking about how hard he was right now.
"I say," Emily said with a wicked grin, "we give him a chance to redeem himself."
"How?" John said.
"Well, there has to be some punishment involved too. So we make him have sex with the person here he would least want to bang. He has to last the same five minutes without cumming. If he wins we talk about a prize, if he loses he cums in that person. No pulling out, No stopping. No closing his eyes. He has to watch himself fuck them." She grinned wickedly at him.
"Who is that person then?" Chloe asked, "John?"
"Nope, we suck each other off a lot. Plus we have had sex like... eight times." John said thoughtfully.
"It's me." Emily said, "After all, who wants to fuck their sister?"
"Come on, no way," Tyler said as the others shouted their agreement. "You want me to fuck you to prove a point?"
"You boasted that you could control it. You failed so now you try not to cum in your sister!" Chloe giggled, "If you win you can fuck me anytime you want for the rest of our weekend here."
"Really?" Tyler asked with a bit of excitement. After all, five minutes of awkward sex for a whole weekend of the girl he wanted, could be worth it.
"Yup." She replied letting the p pop on her lips.
"She will keep that promise too," John said with a laugh.
Tyler was about to ask how John knew that but put it out of his mind as Chloe let her swimsuit fall off. Her breasts were bigger than Emily's B cup and her pussy wasn't clean-shaven like he thought. There was a cute little heart of hair just above her clit. He wanted to feel her around him, just needed to get something awkward but not altogether offputting out of the way. Even if she was his sister, Emily was still sexy as hell.
"Ok, I get you anytime I want for the next two days if I win." He confirmed. Everyone laughed and nodded their agreement. "Ok anyone got a condom?"
"There's a whole box in my room," Emily said coily. "But you can't have one."
"What?" Tyler said incredulously.
"It's a punishment remember?" John teased. "Now I'm not starting the timer until you start moving in her pussy and I'll pause it every time you stop."
"He fails if he stops," Emily said cutely. "and if he fails he has to cum in me. Even if that takes longer than five minutes."
"Unprotected sex?" Tyler said nervously, "You and me? You are on the pill right?"
"Nope." She said as she laid back and held her pussy lips open. "Now get in there.
"But-" He began.
"If you don't start soon you get nothing but shame." Chloe interrupted with a giggle and sat so she could show off her pussy to him.
"Could you at least not distract me like that?" He asked as he noticed she had placed herself where his choices were to look at Emily or her. Her answer was to slowly trace a circle around her clit as John sat next to her for a better view of Tyler and Emily. Chloe leaned on him as her breathing began to deepen.
"Better get started man," John teased after taking a long hungry look at his sister's actions, "If she cums before you are done she may not want sex right away."
Tyler shook his head and looked back down at Emily, she was watching him with an odd expression. Like all that mattered right now was what she asked him to do to her. "What will our parents say if you get pregnant? Worse if they learn it was from me?" He asked her.
"That's the punishment for failing." She leaned up and whispered in his ear. "And I'm really horny right now and I don't care who fucks me." As she laid back down she pulled him with her. Without meaning intending it, his cock slid into her. She let out a soft moan.
"Shit," He said as her hot slick flesh clamped around his throbbing cock. These five minutes might be a real pain.
"Incest for the win!" John shouted with a laugh. "But just being in doesn't count. You got to fuck. Once you start the timer starts and if you stop it's over." He waved his phone at them as Chloe let out a little louder moan than before. "Oh shit," John said looking down at his sister who smiled happily as she rested her head on his shoulder. "Think Chloe will last five more minutes? I don't know, you want to fuck her you better hurry."
Tyler tried not to stare at Chloe, though he did wonder how they were so casual about this. John now had his arm around Chloe, one of her legs was draped over his lap so she could spread her legs more as he held her up. He even ran his hand along her side. Tyler thought watching them might make him cum even if he didn't move so he looked down at Emily.
This wasn't much better. Her shy smile was as cute as ever and he noticed her blush ran most of the way down her chest. She winked at him and bucked her hips just enough to get his attention. The movement was torture and he knew it was about to get much worse. He nodded to her and pulled back until just his tip was in her, then slowly he pushed back in. He couldn't help but love the moan she made as he did.
"Sounds like your cock is just what she needed!" John teased.
Emily grinned as she moaned more with his second and third slow push. He was doing everything in his control not to give in to the instinct to go hard and fast. His body was begging for him to go balls deep and plant his seed in her fertile, unprotected, womb. He glanced up at John and Chloe for a moment to see that Chloe, while still pleasuring herself, had pulled John's speedo to the side and was actively jerking him off.
The sight both confused and aroused him. Seems they thought he and Emily shouldn't be the only ones engaging in incest. Emily's hands trailed down his torso as John grunted out that he had hit the two-minute mark. Emily looked back at the others, Tyler also looked up again to see that John's free hand was now knuckle-deep in his sister's pussy. While she had leaned over to suck his tip. Tyler could feel himself losing this fight so he closed his eyes and tried to focus on slow deliberate movements while reminding himself that it was his sister he was fucking. Of course, the taboo of it only made the pressure in his ball grow. The need to cum was building faster than he liked.
Emily's hand gently touched his cheek. "You have to keep looking. Either at me or at them." She said with a needy moan.
He opened his eyes and looked into hers. She was clearly on the edge and seemed to want him to speed up. He looked down to where his cock was plunging in and out of her tight pussy and saw she was rubbing her clit. He looked up at John and Chloe again to see Chloe trying to catch John's cum as it ran down her chin during a very loud moan. Seems the don't cum part was only for him. John smiled at him as he called out three minutes. Chloe shifted so John could play with her pussy easier but John responded by kneeling next to her. He guided her onto her side and lifted one of her legs onto his shoulder. Chloe seemed to be just as turned on by watching Tyler and Emily as she let John push his cock into her pussy. John was using his thumb to rub her clit as he started fucking her. She closed her eyes and let out a long delicious moan as her hips started bucking on their own. It was clear from the way John had positioned them that he wanted Tyler to have a full view of Chloe's body as her brother fucked her into an orgasm. Seems Tyler and Emily were the only ones who hadn't cummed yet.
Tyler decided he wanted to prove a point. He let himself pick up the pace a little, much to Emily's delight judging by her new moans, and gently pushed her hand out of the way so he could rub her clit with his thumb. The change in her moaning was not helping him keep his control but after seeing John make his sister cum on his cock, he was determined to do the same for Emily. This turned out to be a mistake.
He knew most women had different responses to their orgasms. He had just seen Chloe's hips shake wildly during hers. He noted as he looked up at them again, she was shaking again since her brother hadn't stopped fucking her. However, he wasn't prepared for Emily's. She suddenly tensed and her breath caught. He leaned into her more to push her over that edge. She kissed him hard as her whole body began to shake hard like his vibrating pocket pussy. John cheered out the four-minute mark. One minute to go. An eternity. Emily didn't seem to be coming down from her orgasm. Knowing he was going to lose Tyler tried to pull out.
Emily wrapped her legs around him and pulled him in deeper than he had gone so far. He tried to pull back again but it only meant that she could use her legs to slam him into her orgasm over and over. Still trying to stay in control he tried to go back to his normal pace. But he knew it was about to be over and before the time ran out. Deciding he may as well enjoy it he plowed into her hard and fast, reigniting her orgasm that was just winding down. Chloe cheered and he looked up at her. She was on her hands and knees watching them. John, still fucking her doggy style was counting down the last minute by ten-second marks.
Forty seconds left, Emily's moans were too much. Thirty seconds left, he hoped she had been kidding about being unprotected. Twenty seconds left, Chloe and John had stopped and moved next to them. Tyler noticed Chloe had been creampied by John and seeing her brother's cum run down her leg was all he could take. It was over. He buried himself balls deep in his sister and let out the entire day's with of pent-up cum deep into her. He slowed and stopped as his last pump of cum splashed inside Emily. Her orgasm stopped when he did and she lay there looking fully satisfied with what had happened. Chloe helped him stand up and even licked his cock clean of Emily's juices before diving into her pussy to lick up his cum. Emily giggled with a soft moan of approval.
"You got into it at the end. Nicely done." John said as he patted him on the back.
"I failed." He said flatly. "Also when did you two decide to fuck?"
Chloe leaned over and kissed Tyler on the lips. He tasted his own cum and Emily's pussy. "We have been doing that for a while. Also, your failing wasn't what we cared about." She said.
"They told me they had been having sex," Emily said as John smiled at him. "I didn't believe them until they invited me into a threesome. Then we joked about me having sex with you. John said you had talked about the idea before." She grinned at him.
"Well, that was hypothetical!" Tyler said incredulously. John moved up behind his sister and reached one hand around to rub her clit.
"Not for me it wasn't. I told you I would fuck my sister that week." John smiled.
"So this was all a ploy to trick me into fucking my sister?" He said flatly.
"Did anyone force you?" Emily asked.
"No." He replied.
"Did you like it?" She asked.
"Yeah, but, no condom." He suddenly felt very worried.
"Both girls are on birth control man," John said with a laugh. "If not they would both be having my baby."
"We kinda spent all day yesterday fucking each other," Emily said shyly.
"While I was at work?" Tyler asked, already knowing the answer.
"I wanted to fuck you too. I wanted us all to fuck. We knew that you and John had a causal thing for a long time and you never even tried to hide how much you liked Chloe." Emily said, laying back down with her legs still in their fuck me position.
"So," Tyler said slowly, "We spend the rest of the weekend having an incest orgy?"
"Not only," Chloe said, "I enjoy fucking Emily and I would love to fuck you too. Plus I want to see you and John fuck." She giggled.
Tyler thought about it for a moment, then shrugged, "Sure, You can have me next Chloe."
"Next?" She said slightly confused.
"Yeah, I liked this but I was focused on winning." He knelt between Emily's legs again. "Now I want to enjoy you." He said as he kissed her and pushed his cock back into her and his tongue into her mouth. They moaned sweetly together as he began with no hesitation this time.
He let out a very happy moan as he felt John push his cock into his anus. He looked back at Emily who seemed to be in heaven as she watched her brother get fucked while he fucked her. Chloe moved between them as Emily leaned back to lick her pussy entrance. John moaned happily as he sped up in Tyler's ass. Tyler matched his speed in Emily as he leaned forward to suck Chloe's clit. The pressure in his balls built again much faster than before. He didn't hold back this time but let himself cum hard and fast. The others seemed worried he would stop but he kept going. John gripped his hips and controlled the pace. Off of John and into Emily. Out of Emily and onto John. Over and over with a wonderful speed. Chloe gripped his hair as she orgasmed on his tongue and Emily's face. She pulled back to lie next to Emily and watch.
John grunted in a way that told Tyler he was almost done. He turned back and kissed John sending him over the edge. John pulled out and sat back to watch as Tyler finished with Emily. He bent over to kiss her again as she had another orgasm. Hers caused him to cum again. They stopped moving for a while after they finished, just staring into each other's eyes.
"This is going to be a very fun weekend," John said as Tyler pulled out of Emily. "Still hard?" He asked Tyler.
In answer, Tyler smiled and moved over to Chloe. She grinned and opened her legs to let him in. His first push into her was everything he had ever hoped it would be. Soft, tight, wet and so fucking hot. He wasted no time in pounding her as hard as he could. Emily's moans caught his attention. John had moved her into a kneeling position and was fucking her from behind. She was loving every second of it but seemed to be yearning for Tyler again. He wanted her again too. He kissed Chloe hard as she orgasmed. He kept his composure and kept going, hoping to make her cum again before he pumped his first load into her.
Emily moaned cutely and leaned closer to kiss Chloe. He watched as his sister kissed the girl he had always wanted to fuck while he was balls-deep in her. He glanced over at his best friend, who cum was leaking out of his ass, pumped a load into his sister to join the three he had already put there. He pushed in hard and deep, feeling himself hit her cervix as his cock relentlessly pumped his cum into her pussy. They all lay down in a heap of moaning and heavy breathing. Emily and Chloe switched places and cuddled up next to their own brothers. Tyler let his cock slide into Emily again but only held it there. Enjoying her feel. Chloe and John did the same.
"Let's take a break for a bit," John said.
"Yeah but only a bit." Chloe sighed.
Emily giggled and wiggled her butt. The sensation was delightful and he began to slowly move in and out. Emily seemed to be trying to hide that he was fucking her again so he joined in her little game. He kept his movements slow and slight as they all discussed how John and Chloe started having sex.
Seemed they had been on a family road trip and she had to sit in his lap for a trip on an off-road trail. They had all been in swimwear and his parents, both in the front seat of the jeep, hadn't considered how to pack all the things they wanted to bring. Chloe said she didn't mind sitting on his lap. He had agreed reluctantly. During a bouncy part of the ride, she had slipped down, dragging his suit off his cock in the process. She had bounced up into the right spot a moment later but his trunks didn't go with her.
Tyler felt Emily stiffen as he kept going very slowly. He was struggling to keep his voice steady as he asked them to continue.
Chloe hadn't noticed his cock was out so just kept sitting there. She also had been wearing a one-piece that was a little too big for her. The crotch was loose and tended to slip to the side. During another bounce, it did leaving her naked pussy pressed against his exposed cock. He had tried not to get hard but failed nearly right away.
Tyler laughed to cover Emily's escaped moan. "Looks like I'm not the only one who can't avoid getting hard from my sister."
"I told you that at the start." John winked as he kept explaining.
Chloe had turned to look at him with surprise as more bumps had his length rubbing against her, at the time, virgin clit. She tried to shift forward in an attempt to get his suit back in place but only succeeded in getting into the perfect position for his cock to slide in. She had moaned in shock, their parents asked if everything was ok. She surprised him by saying yes. She sat back, keeping him in, and looked to him for permission. He had nodded and they stayed like that for the rest of the two-hour ride. They had both orgasmed several times and the first one from Chloe nearly got them caught. But in the end, they had gone the whole ride in bliss while their parents hadn't known.
As their story wound down he hugged Emily. He thought about how quickly this all happened. He admitted to himself that he had been thinking about having Emily. John had put the idea in his head. They planned this for a while. He decided he liked the direction this week was going.