Sister Steals Brother's Virginity

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Sydney: "You should come and tan with me Jack, you're looking a little pale haha."

Sydney smiled flirtatiously, turned back over and layed down. Now completely nude wearing only her sunglasses.

Jack slid open the rest of the sliding door, took his shirt off, and walked over to Sydney.

Sydney: "You gotta be naked Jack, it's only fair."

Jack: "I was planning on being naked don't worry!"

Sydney smiled and pretended to pay no attention to Jack, but she watched and paid close attention as Jack slid down his pj's revealing his semi erection. Even at semi, Jack was rocking a 6 ½ inch thick cock. Sydney's cheeks turned red and she tried to hide her smile as she looked at Jack now completely exposed.

Jack slid the other sun chair over beside Sydney and he laid down. Sydney reached for the tanning oil and handed it to Jack. Jack squirted some into his hand and started to rub it on his body. He started at his chest, and then his abs, then went down to his groin.

He spread the oil around his cock and then he gripped his shaft and stroked it. Then be got his balls and down his legs. All while Sydney watched. Her breathing had become heavy and the mound of beauty between her legs was now wet. Jack's cock was now a full 8 inches. Thick, hard, and covered in oil.

Sydney: "You know I could use some more oil, wanna help me out?"

Jack: "Hell yeah!"

Jack got up and sat on the edge of Sydney's chair. He squirted some oil in his hands and started to rub it down Sydney's legs. He rubbed it deep on Sydney's feet and in between her toes, massaging them as well. Sydney giggled here and there but she loved it.

Jack moved up her legs and got to her thighs. They looked stunning, so thick, so big and tan and so juicy. He just wanted to stick his cock between them and fuck them hard. He ran his hands down Sydney's thighs and lathered them with oil.

Jack's muscular hands sent chills down Sydney's body and made her tingle with excitement. She bit her lip and smiled as Jack caressed her. He touched and squeezed every part of her legs, trying to savor the moment. Sydney twirled her pubes and played with them as Jack touched her so intimately.

Then he made his way up to Sydney's chest and her breasts. He cupped and squeezed her boobs. He teased her nipples and drizzled some oil over them. Sydney shivered and giggled. Jack played with her nipples and made Sydney moan with every squeeze.

Then Jack made his way down to Sydney's pussy. Her small, soft, tuft of hair was all wet. She opened her legs a bit, welcoming Jack's warm embrace. His fingers glided down the wet lips of Sydney's pussy. They felt heavenly to Jack and her clit felt even better. He rubbed it and played with it in a circular motion.

Sydney's hips started to gyrate because Jack's touch felt so good. Jack went up and down Sydney's body for a half hour. Then he told her she needed to turn over to get her back. Sydney giggled and hurried to turn over with excitement. Her gorgeous bubble but was now directly in front of him. So fucking juicy and thick.

Sydney laid her head on her arms facing towards Jack as he massaged her. Jack opened his legs and his dangling monster cock was now hanging for Sydney to see. The tip was covered in pre-cum and it was engorged. She never stopped looking at it the whole time.

Jack covered Sydney's ass in oil and caressed it ever so. He spread her cheeks revealing her tight, little butthole. It was clean, and just a slightly darker shade then her skin. And then Jack saw her beautiful pussy from behind. He rubbed his fingers down it and played with its wetness more.

Eventually, Jack stuck his 2 fingers inside of Sydney. She jolted and moaned with a feeling of pleasure. He fingered her in a curved motion, in and out, in and out, in and out, going faster and deeper. His fingers stretched Sydney's tight pussy and broke her hymen instantaneously.

Jack simultaneously rubbed Sydney's ass and fingered her pussy until she was leaning back on the chair and cumming on Jack's hand. Her eyes closed and her jaw dropped as she let out a scream of joy. She squirted all over Jack's hands and her ass jiggled with every movement. But Jack didn't stop, he kept fingering her and rubbing her clit.

Sydney was on the verge of tears as Jack was making her feel so good. Jack made her cum about 6 times. Each time, her inner muscles clenched around Jack's fingers and she squirted her juices all over the chair and his fingers.

Sydney lay back in the chair, exhausted and overwhelmed with pleasure. Jack sat back down on his chair and rested, his arm was tired. After a few minutes of heavy breathing and recovery...

Sydney: "Now I wanna return the favour..."

Sydney got up and similar to Jack, she sat on the edge of Jack's seat and started to stroke his cock. She leaned over him and put both her hands around Jack's massive cock.

She stroked it slowly and sensually, up and down, up and down. Sydney rubbed the pre-cum all down Jack's dick and then licked her fingers clean. Jack sat back and moaned at the touch of Sydney's soft hands. Sydney excitedly brought her head down and her little pink lips kissed the tip of Jack's cock, she licked it and slowly shoved it in her mouth.

She went up and down Jack's shaft licking and kissing. She took as much as Jack as she could in her mouth before she started to choke. Sydney started to slobber and suck Jack's dick very aggressively. She was able to take about 7 inches in her mouth before she choked.

Sydney sucked Jack for about 10 minutes before she finally took it out of her mouth, and sucked on Jack's balls as she stroked his shaft. She stroked him faster and harder and Jack was about to cum.

Sydney could feel Jack's balls clench as the cum rose out of his cock. Jack blew several loads all over Sydney's face and boobs. She kept stroking him all while he came on her face.

Sydney held Jack's now limp dick and licked the cum off it. She didn't miss a single bit. Then she scooped the cum from her face and swallowed it all. Sydney smiled and winked at Jack as she laid back down on her sun chair. Jack drifted off asleep as he lay there out of breath.

When he woke up he was just on the verge of a sunburn. Sydney wasn't beside him anymore. Jack got up and headed inside. Sydney was at the kitchen counter making a smoothie, still completely nude. Natalia, was on the couch looking at her phone.

Natalia: "Jesus Jack your dick's red! Looks like you two had fun haha."

Sydney: "We did...It sucks you weren't here!

Natalia: "We'll have some more fun tonight don't worry."

Jack got excited and his cock grew larger. Sydney and Natalia looked at each other and laughed. The rest of the day was pretty quiet. It was around dinner time that things started to get fun.

Jack had basically spent the rest of the day playing on his computer while the girls hung out. It was about 6:30 pm and Jack was in the middle of a CS:GO match when he got a text from Natalia.

Natalia: "Hey Jack you hungry? There's a number for pizza and money on the counter. Can you order some for us all, Sydney and I are in the hot tub. Thx!"

Jack: "Yeah I'll order it in a few."

Natalia: "Come join us in the tub after ;)"

Jack: "Kk :)"

Jack finished his round and turned his PC off. He stripped down and put on his bathing suit. Then Jack went to the kitchen and ordered a medium double cheese and pepperoni pizza from their favourite pizza place. They said it would take about 20 minutes.

Jack hung up the phone and turned to go outside. He stopped in his tracks and realized they girls were probably nude and he should just strip down completely. And sure enough, they were. Jack took his shorts off, slid open the sliding door and walked over to the tub.

Sydney: "Hey Jack what's up?"

Jack hopped in the tub and relaxed deeply in the warm water.

Jack: "Not much, what have you guys been up to?"

Natalia: "We've just been talking. Nothing that interesting haha."

Sydney: "Are we gonna tell him now or later?"

Natalia: "We can tell him now if you want..."

Jack: "Tell me what?"

Natalia: "When I was out today, I bought a joint from a friend. Sydney and I were gonna smoke it tonight, wanna join in?"

Sydney: "It'll be funnn"

Jack: "Oh hell yeah! I've never smoked but I've always wanted to!"

Sydney: "We don't smoke that often but when we do it's always interesting."

Jack started to think about all the possibilities of tonight. Would he smoke with them and would they all forget about having sex? Would he smoke with them and they come to their senses? Would he smoke with them and he ends up doing something he regrets?

And then he started to think more positively... would he smoke with them and he ends up having the best night of his life? Would he fuck them both and have the most memorable end to a vacation ever? Jack had no idea but he was hoping for the best.

Sydney: "God I love being nude in here! It feels so freeing."

Natalia: "Right? My boobs are just floating around haha."

Sydney: "Jack I'm sure your Megalodon of a dick is floating freely right now right?"

Jack: "As free as can be."

Natalia moved over to Jack's left and Sydney moved over to his right. They started to kiss Jack simultaneously and rub their hands on his chest. His dick started to throb and the girls could tell.

Sydney reached under the water and grabbed it. Natalia did the same. The girls sat and stroked Jack as he kissed both his sister and Sydney's boobs. He played with their nipples and bit them ever so slightly.

Natalia had started to grab Jack's balls, massaging and playing with them as Sydney stroked. Jack was about to cum, just as the doorbell rang. He liked to edge himself though so he hopped out and ran inside.

The girls started to play with each other as they waited for Jack to return. He quickly put his shorts back on, they did not hide his erection at all. Its size and thickness were clearly visible through his shorts.

Jack opened the door and handed the money to the delivery boy. He looked somewhat similar in age to Jack. He noticed Jack's cock in his pants almost immediately. He was shocked and excited but Jack paid no attention.

Jack was filled with adrenaline and was hurrying to get back to the girls. Jack closed the door, put the pizza in the oven so it stayed warm, and then practically ripped his shorts back off as he ran to the tub.

Sydney was fingering Natalia as Nat grabbed her boobs. Jack hopped in behind Sydney and started to play with her pussy from behind. Just as he had done hours earlier, he ran his fingers through Sydney's lips and massaged her clit.

Then he started to finger her at the same pace she was fingering Nat. It was a 3 way train of fingering and caressing. Both girls came aggressively. Their cum leaked into the hot tub water and they wanted more.

Sydney bent down so she could eat Natalia's pussy, leaving her ass exposed just out of the water. Jack took this opportunity to now eat Sydney's pussy. Even though Sydney was in the tub, Jack could still taste her natural juices and wetness.

He felt her body quiver and shake to the touch of his tongue on her labia and clit. Jack grabbed Sydney's ass as he ate her and Sydney held up Natalia's legs as she ate her.

Everyone was cumming, moaning, shaking and being filled with intense pleasure. Jack started to tongue fuck Sydney and she ended up squirting in his mouth again. As she came Jack took his hand and rubbed her clit and lips together as she squirted. He loved the way she tasted and Sydney loved the way Natalia tasted.

It was about 7:40 pm when they decided to go back inside and dry off before they smoked the joint. By the time everyone was dried off and in the living room, still very nude, it was about 8:00 pm.

Sydney's glowing face was the result of her many orgasms. Her hair was was partly wet and dry and it looked super sexy. Natalia lay on the couch as she rested her eyes. Her big boobs on her chest looked perfect and Jack wanted so much to suck on them some more.

Sydney reached into her purse and pulled out the joint. She grabbed her lighter and she lit it up. Sydney inhaled a big breath and then exhaled it through her nose.

Jack smiled in awe. Sydney handed it to Natalia and she took a small hit fairly quickly. Jack got the joint next and he took his time taking a hit because he didn't want to choke and look inexperienced in front of the girls. They passed the joint around until they all felt the high.

Sydney had started to touch herself gently. She rubbed a single finger up and down her slit just to feel how wet she was. Jack got hard again and began stroking his cock, Natalia was caressing her tits. They masturbated while all looking at one another, each getting more horny by the second.

Jack: "Nat your boobs look so fucking nice. Can I play with them?"

Natalia: "Go ahead..."

Jack stumbled over to her and sat facing her as he squeezed and played with her big breasts. They felt amazing to Jack because he was horny, but also because he was super high. He didn't notice but his boner was resting on his sister's leg.

Natalia giggled and Sydney just watched as she started to touch herself some more. Jack made Nat's nipples hard and was now flicking and rubbing them. Natalia was lightly circling the tip of Jack's cock to tease him.

Sydney was now full on rubbing her clit and tits with her legs up in the air, the sight before her was very erotic. All she wanted in that moment was to take all of Jack's cock in her pussy. She just wanted it inside her and to feel his cock stretch her insides. It's like she needed it, a craving for Jack's thick cock, and cum.

Sydney increased the speed she was rubbing her clit and she came again, leaving a wet stain on the chair. Sydney licked her fingers dry, then jumped up and walked over to Jack.

She kissed Jack on the mouth whilst pushing him back on the couch. She got on top of him and she moved up to his face. Her thick thighs and ass were wrapped around his head, and her pussy was in Jack's mouth in a matter of seconds.

Jack's view was incredible, Sydney's ass on his face, her cheeks slightly jiggling as he ate her out. Her hips gyrating fastly. Natalia leaned down and took her brother's cock in her mouth. She was able to go the full 8 inches and she did it without hesitation.

Stroking and sucking while getting more and more wet. Jack could feel his sister's tongue wrapped around his dick and it felt amazing. Jack blew a huge load in Natalia's mouth. She was surprised but she kept on sucking even though she was choking.

He blew several thick loads down her throat yet somehow was able to keep a full 8 inches.

Natalia: "Omg your cum tastes so good!"

Sydney: "Oh Jack I want you inside me! I want you to fuck my tight pussy hard!"

Sydney slid down Jack and turned around to ride him. She let her body down and rested her pussy on Jack's dick. She rubbed along its length, back and forth to lubricate it. She let out a few moans and finally, when his dick was wet enough, she took the shaft and shoved it inside of her wet pussy.

Sydney took the entirety of it in her and she let out a loud scream of intense pleasure. Her head tilted back and her jaw dropped as she began to ride Jack. His cock rubbed against Sydney's whole inside of her pussy.

Jack was speechless as he witnessed her bouncing up and down on him. Jack put his hands on her waist to help her ride him. Then he brought his hands to her boobs and played with them. Her pussy was so wet, it was dripping and flowing all over his dick and chest.

Sydney put her hands on Jack's hands and made him squeeze her tits harder, and let out a few more loud moans. They interlocked hands and held each other tight as all of Jack's cock went in and out of Sydney.

Sydney leaned down on Jack and kissed him as his cock went in and out of her. Natalia was watching from behind as Sydney's ass bounced up and down on Jack's cock. Her tan big ass bouncing aggressively. Jack wrapped his arms around Sydney's back and spread his legs so he could slam his cock into her.

He held Sydney still and started to thrust deeply into her pussy as Sydney's eyes rolled back. Sydney came, and came, and came, all over Jack's dick as he fucked her hard. Jack let out a big moan and emptied his load inside of Sydney.

His cum shot straight into her and leaked out as he slowed his pace. There was a pool of cum from both Sydney and Jack all over the couch cushions, and on each of them. Sydney leaned back up with Jack's cock still in her and rubbed her clit for a few seconds.

Natalia: "That was the hottest thing ever! Watching my brother fuck my best friend!! I'm so fucking wet right now omg Sydney taste me PLEASE!"

Sydney got off of Jack and spread Natalia's legs as she stared at her soaking pussy. Natalia pulled Sydney's head in and she tasted every drop of her. Every single lick and touch of Nats pussy was sending tingles and nerve racking sensations throughout her body.

Jack sat up and pulled Sydney's ass closer to him. Her ass was so beautiful in this position, her back arched, her big tan cheeks in perfect position for Jack to fuck, and she was eating his sister's pussy.

He took his cock and played with her pussy, then he shoved it all back in her. She let out a huge moan as she wasn't prepared for the same wonderful sensation again. Jack took ahold of Sydney's ass and pounded her hard.

His cock slamming into her pussy hard and deep every time, fucking her utterly breathless. She was so wet and so warm, filled with her cum and Jack's. Jack was gonna cum again.

He pulled his cock out of Sydney and blew his load on her back. Then he put his cock back in her and continued fucking her. He couldn't stop, this was all he wanted to do and now he was doing it.

Jack fucked Sydney non stop for about 30 minutes, all while Natalia played with Sydney, or she just watched and played with herself.

Natalia: "Okay Jack I want a turn! I want you to fuck your big sister."

Jack thrusted his cock into Sydney one last time and pulled it out slowly, before he leaned back and took a deep breath, as he was exhausted. Sydney got into the position Natalia was in; laying back on the couch with her legs spread for Natalia to eat her pussy.

Natalia then got into the position Sydney was in; bent over, ass up (doggy style). Nat started to lick Sydney's pussy, she could taste both Sydney's cum and Jack's. She loved the combined flavour. Jack gave his cock a few strokes and then slowly pushed it into his sister.

Natalia lost focus on Sydney and also lost her breath. She could feel Jack deep inside her and was ready for him to fuck her as hard as he fucked Sydney. Without a second thought, Jack started to slam his cock into Natalia. Deep and hard, just as he had fucked Sydney.

Natalia's boobs bounced as Jack fucked her. Nats ass wasn't as big and round as Sydney's but it was still super hot and perfect to grab. Jack spanked his sister and pulled her hair as he thrusted into her.

Something about Natalia really turned him on. Sydney turned him on more, but with his sister it was different. Jack was turned on by the shear sin of fucking his own sister. His own flesh and blood, his family.

The very sin Jack was committing, and the rush he was receiving, felt utterly amazing to him. He had seen his sister nude countless times growing up, especially since he started spying on her, but now he was fucking her. Actually fucking his own sister.

Natalia pussy wasn't as tight as Sydney's but it still felt great. She started to move her body with Jack and he ended up cumming in her. Just as he had came in Sydney, he blew his load straight into Natalia's pussy and it leaked out as he kept fucking her.