Sister Steals Brother's Virginity

Jack moved his hands to both of their pussies and ran his fingers down their slits. Up and down his fingers went as he teased the girls. He then started to rub their clits with a circular motion, the girls started to squeeze their breasts and moan with pleasure.

Finally, when Jack's fingers were wet enough, he stuck 2 of his fingers on both hands into each girl, and fingered them intensely with a curled motion, in and out. He continuously fingered their pussies and hit their g-spots. He knew where it was because one of his ex gf's showed him.

He made the girls scream with intensity, literally scream. They covered their mouths but that barely helped as the girls came on Jack's fingers. Their backs arched and their bodies shook as he made them orgasm.

The girls smiled at Jack and they hopped back in the water. Jack got on the ledge and the girls gave him a handjob. They took turns stroking his shaft to playing with his balls. After 10 minutes, Jack felt the cum rise out of his cock and he came all over.

Jack's cum got on Sydney and Natalia's face and on both of their tits. Natalia kissed Sydney and licked the cum off her face and Sydney did the same to Natalia. Then the girls rubbed the cum all over their tits until it was dry, and kissed Jack once more before hopping out.

Jack lay back on the concrete, breathless, and breathing heavily as he watched Natalia and Sydney stroll across the grass and back to the house. Their asses and boobs bounced and jiggled as they walked.

Jack closed his eyes and smiled as his cock lay limp and lifeless on his chest. This was the best day of his life, so far...

Saturday

It was the middle of summer and Jack hadn't been playing any sports, so he would go on frequent runs in the morning to stay fit. He woke up at about 5:30 am and changed into a t-shirt and shorts. He crept down the stairs as to not wake the girls and went out the door.

As Jack ran, he watched the sunrise over the neighborhood. It looked absolutely stunning because the sunlight put a nice warm coat of light on almost everything. Jack liked to watch the trees in his neighborhood when the sun rose because he liked the way the light moved through the leaves.

It brought him peace and clarity and he would often do his most deep thinking on his morning runs. Today specifically, the only deep thinking he did was think about Sydney and Natalia. He had no idea what was going on with them, or more importantly what was going to happen when his parents came back.

Jack didn't want to think about that right now though, because he didn't need to. So he decided to just enjoy everything that was happening and to make the most out of it.

When Jack came back to the house, it was about 7:00 am and he was drenched in sweat and was trying to regain his breath. Jack walked through the front for and kicked his shoes off out of exhaustion. He walked to the den where Sydney and Natalia were watching TV and he face planted on the couch.

Natalia: "Morning Jack"

Sydney: "Good morning Jack, looks like you had a fun run!"

Natalia: "He looks like he's about to pass out haha!"

Jack: "I am about to"

Jack rolled over in pain and took a deep breath out as he rested his eyes.

Natalia: "Did you have any water today Jack?"

Jack: "Nuh uh"

Natalia: "Oh my god. Hold on I'll get you some you dummy."

Sydney laughed and put her attention back to the TV. Natalia got Jack a glass of water and she poured a bit out on Jack's face just to mess with him. Surprisingly, Jack wasn't mad.

Jack: "I don't even fuckin care, it's too hot and I'm way too tired to get you back for that"

Natalia: "Well Sydney and I were gonna ask you if you wanted to go for a bike ride but I guess you're too tired now huh?"

Jack: "Oh so that's why you guys are up so early, but yeah no I'm way too tired."

Natalia: "Haha alright."

Natalia now turned to Sydney.

Natalia: "Do you wanna go leave after you're done eating babe?"

Natalia immediately realized what she had just said in front of her brother. There was a worried look on Natalia's face, Sydney looked a little shocked, and Jack was confused.

Jack: "Nat, did you just call Sydney 'babe'?"

She didn't respond at first because of how stunned she was at her own mistake. She didn't know what to say.

Natalia: "Umm yeah I did. It was- it was an accident though I didn't mean to!"

Jack: "Oh, ok."

*Silence*

Sydney: "You know what, no. Jack, your sister fully meant to call me babe. Nat and I, are in a relationship now. We both realized we love each other much more than any friendship."

Sydney smiled at Natalia and got up to kiss her. The girls said goodbye and went to the garage to get their bikes. Jack sat on the couch, not knowing how to process this information at all.

Jack had more or less come to accept the fact that they were a little freaky, like sexually. But his long time crush, the person he thought about the most, was now dating his sister! He couldn't believe it, and as he felt all his feelings come up he couldn't help but get mad at his sister.

He knew he shouldn't be mad at her at all, but Jack couldn't help it. The real anger was about him not being able to shoot his shot at Sydney, his chance at asking her out. Jack assumed after this little "vacation", it would be a for sure yes from Sydney if he were to ask her out.

Jack sat on the couch the whole time the girls were biking. He couldn't figure out how to think about their new relationship. So many emotions were coming out very fast. Then he heard the front door open and Jack was still on the couch...

*30 minutes before, immediately after the girls left the house*

Natalia: "I'm sorry I denied calling you babe Syd, did I offend you?"

Sydney: "Oh don't be sorry Nat! I'm not mad at all, I just think it's stupid to try and hide our love. All I want to do is tell people about you and us."

*Sydney said with a heartwarming smile"

Natalia: "I love you!"

Sydney: "I love you too! Come on baby."

The girls hopped on their bikes and rode down the driveway, onto the empty morning streets.

The front door opens and Jack is still on the couch. Still not knowing what to say or do, Jack stands up, walks into the hallway and sees Sydney and Natalia un-tieing their shoes. Natalia says hey to Jack and Jack interrupts her and speaks to Sydney.

Jack: "Sydney, I, I love you. I really do, I love you, and I have for a long time I genuinely think you are the most beautiful woman I've ever seen. I think you are so unique Sydney, and I mean that in every way. Your voice is angelic, I think that slight lisp you have is absolutely adorable. Sydney you have the kindest smile and the most gorgeous eyes. Your hair is such a perfect mix of blonde and brown I love it. I love the way it sways when you walk and I love whenever you put it in one of your messy buns. Whenever you smile it lights up a room and whenever you talk my heart melts. You are so god damned pretty, you're beautiful. Words can not express it, they really can't. You make me so happy, so fucking happy Sydney. And it's not just you're gorgeous self, I love you for you. Sorry if that made you guys feel weird, but I had to say it."

Jack took a feel breath out, and then walked upstairs to his room. He felt proud of himself for saying what had been in his head for years. With a smile on his face and a killing headache, he laid back on his bed and drifted off to sleep...

Sydney and Natalia sat in awe on the floor, with their shoelaces still in hand, they had trouble finding any words at all. Sydney had started to tear up halfway Jack's speech. She wiped her eyes and sniffed her nose and she finished untying her shoes.

Natalia: "I, I'm at a loss..."

Nat stopped as she noticed Syd crying. She sat up and ran to Sydney and embraced her as the 2 hugged each other tightly.

Natalia: "Are you ok Syd? Do you wanna talk about it?"

Sydney: "That was probably the nicest thing anyone has ever said to me. I mean, I never knew he thought that about me."

She said as she started to cry again. Sydney's cries were a mix of happiness and sadness. Happiness because of Jack's heartwarming words, and sadness, because of Jack's heartwarming words. She knew Jack and hers relationship was now completely different and possibly even ruined.

Natalia: "Yeah that was super surprising, I mean he had that memorized!"

Sydney chuckled in Natalia's arms and she felt a little better.

Sydney: "If there's one person I need to talk about this with, its Jack. I need some time to gather my thoughts and myself together. Do you mind if I have some alone time Nat?"

Natalia: "Not at all I understand fully! I hope you guys can sort this out."

Sydney and Natalia let go of each other and Sydney's tears had just about dried up, her eyes remained wet and her cheeks red.

Sydney: "Thank you Nat, I love you so much."

Natalia: "I love you too baby."

They hugged each other once more and Natalia left Sydney alone for a while. Sydney went to the living room and sat on the couch. Natalia went up to her room and shut her door. Sydney buried her head in her hands and she began to think.

Sydney loved Natalia, she really did. So either way she's still going to be with Natalia in the end. She knew she had to be sympathetic to Jack and handle the situation lightly, but she didn't know how!

She first sat down at about 7:40 am, and didn't get up till about 2:30 pm. She hadn't eaten lunch and she had a killing headache, but she had finally pulled herself together and was ready to talk to Jack.

Sydney sat up, drank a glass of water and headed upstairs. She was sad and nervous, and her feet felt heavy on the floor. When she got to the door, she knocked and waited for an answer, but there was none. She knocked again and there was again, no answer.

She opened the door and peeked in, Jack was still asleep on his bed. Sydney tip-toed to his bed. She sat down on the edge and nudged Jack awake.

Sydney: "Jack, Jack wake up."

Jack: "mmm, what, what's going -"

He stopped as he saw Sydney at the end of his bed.

Jack: "Oh, hey Syd."

Sydney: "Hey Jack, can we talk?"

Jack: "Yeah, of course."

Sydney: "Jack, I've had lots of boyfriends, and I've befriended lots of guys. Most of them were pretty nice, and pretty normal. I've loved a lot of them too, obviously not that much cuz we're not together still. The point is, none of them have ever said, anything as sweet as that. I mean, after you left I cried because it was so nice! You made my heart so warm, and so full Jack. But I also cried because of us, and Natalia. I've known your sister a long time, since we were in kindergarten! Since then I've gotten to know her very well, I've developed a love for her, and since these past few days I've realized that that love is real, and it's not just a friendly love. Your sister is amazing and all I want to do is love her. I can't explain it, but she just means everything to me. But I love you too Jack, not the same way, but I still love you. You're one of my best friends believe it or not. You've always been so nice to me and I can tell you're a genuine guy. I actually had a crush on you not too long ago. Jack, I, I want to be with Nat, she means the world to me. I'm sorry Jack."

There was a long pause in the room. Finally, Jack spoke to Sydney.

Jack: "You don't have to be sorry Syd. I understand."

He didn't feel like talking and Sydney had sensed that. She got up to leaved but she stopped, and turned to Jack and kissed him on the cheek, she whispered in his ear..

Sydney: "I promise you and I will have some more fun before I leave, might even get your sister involved..."

Jack's face lit up and Sydney smiled and walked out of his room. She went to Natalia's room where Sydney found her reading at her desk.

Natalia: "So how did it go? Are you guys-"

Before she could finish her sentence Sydney had leaned down and kissed her. Nat could see the happiness in her eyes.

Natalia: "What was that for baby?"

Sydney: "Nothing I just, I really love you Nat."

Natalia got up and hugged Sydney for a long time.

Sydney: "Hey, would you be down to, fool around some more, with your brother? I kinda promised him we would, or I would at least."

Natalia: "Yeah sure, that'll be super hot!!"

Sydney: "Oh great I can't wait!"

That night the girls had planned to watch a scary movie. They got on their pj's and made some popcorn.

Jack came down the stairs and asked what was going on. He was still sad, but he felt a little better. The girl he liked for years basically just rejected him so he wasn't feeling too great.

Jack: "What are you guys up to?"

Sydney: "We were gonna watch a scary movie, wanna join us?"

Jack: "Sure, which one?"

Natalia: "Scary movie, you know the remake of scream? "

Jack: "Oh haha"

Ever since Sydney whispered in Jack's ear, he was constantly waiting for "the fun" to start. Sydney and Natalia sat on the couch and cuddled up next to each other, while Jack was in the big chair.

The movie started and all of them were watching, laughing, and enjoying themselves. The movie got to the scene where the girl in the beginning is running through the sprinklers in her underwear. Jack got turned on and he had an erection poking at his pants.

Natalia noticed Jack's boner and nudged at Sydney to look at it. The girls looked at each other and giggled. Sydney gave Natalia a nod and the two girls lowered their blanket and started lightly caressing themselves. They squeezed one another's boobs and thighs, they kissed each other's necks and lips.

Jack heard a few moans and kisses, so he looked over at the girls and they were making out. Natalia's hands were on Sydney's boobs and Sydney's hands were between Natalia's legs. Jack turned his body and repositioned his legs so he could squeeze his cock.

He watched and teased his cock over his pants as the girls made out. Sydney looked over at Jack and she smiled at him with a sexy face.

Natalia also noticed Jack and when she did she immediately pulled Sydney's shirt up. She wasn't wearing a bra so Sydney's perfect breasts popped out. Her nipples were hard and her chest was sweaty.

Natalia started to lick Sydney's boobs up and down. She bit them and played with them in her mouth with her tongue. Sydney had begun rubbing Natalia's clit over her pyjamas and now both girls were moaning quite loudly.

Jack decided to slide his pants down to reveal his now harder cock in his boxers. He rubbed his dick thoroughly over his underwear to Sydney and Natalia. Natalia couldn't take it anymore, so she got up and slid her pyjamas and panties off, revealing her dripping, shaved, lips and mound.

She sat back on the couch and then Sydney took her pyjamas off as well, leaving her pink panties on tho. They were very wet. Sydney leaned down over Nats legs and started to lick her pussy. She brought her tongue up and down Nats wet slit, playing with her pussy lips and licking her clit.

Natalia's pussy lips were radiating with warmth and they welcomed Sydney's hot tongue. Nat grabbed Sydney's head and pushed it further down between her legs.

Jack loved the sight of Sydney's round, cute, big sexy butt facing him as his sister moaned loudly. Sydney now had one knee bent on the couch, between Natalia's legs, while her other leg was stretched straight to the floor. Sydney's ass cheeks were very appealing in this position.

Jack had pre-cum soaking through his boxers so he slid them off and started to stroke his cock. Natalia's head was bent back over the couch as she was nearing climax. She bent it back over and when she saw Jack's massive cock out, being stroked, she came. She came hard, climaxing in Sydney's mouth.

Her pussy squirted a bit and she rubbed her clit as more and more came out. Natalia legs and pussy were shaking and quivering as she pushed Sydney's head up because she couldn't control herself.

Sydney sat up and slid her panties down, her thick thighs and tan legs matched with her wet little pussy were to die for. Sydney used her finger to soak up her cum and she motioned for Jack to come over to her.

Jack jumped up and leaned down between Sydney's legs. She ran her hands through his hair as he tasted and licked her supple pussy. Jack licked and ate out her pussy, making her moan loudly.

Jack's tongue made its way into her and played with every part of her pussy. Sydney squeezed her legs together and pressed Jack's head together with them. Jack continued to lick her clit and tongue fuck her.

Natalia was focused on Sydney's nipples again. They looked so perky and sexy. Jack had began to rub his cock against the couch as he ate Sydney's pussy, he was humping the couch now because it felt so good.

All he wanted to do was stick his cock in both of them. Jack felt Sydney's muscles tense up and he knew she was about to cum. Sydney squeezed her tits and arched her back as she moaned with pleasure. She too, had squirted in Jack's mouth. But Jack didn't mind, he loved it even more.

Jack couldn't take it anymore so he stood up with Sydney's cum dripping from his mouth and with a few strokes of his throbbing cock, he came all over Sydney. He blew his hot load on her. He had gotten cum on her face, her boobs, her chest, and her pussy.

Sydney laughed with excitement at how much was on her. Natalia leaned down and licked the cum off of Sydney's face, and breasts. Sydney had rubbed the cum on her soaking pussy into her. She was on birth control though so there was no worry.

Jack stood over Sydney and Natalia with his cock still dripping with cum, trying to regain his breath. Sydney sat up and gave his dick a quick lick and kiss to get the cum off. Jack looked at her and was super excited at this because it was the closest thing he had gotten to a blowjob.

Jack: "Sydney you taste amazing!"

Sydney: "You're sister tastes amazing too!"

Natalia: "Jack you can taste me tomorrow, you know, before you fuck us..."

Jack went to bed with another boner, he couldn't wait to have sex with both girls tomorrow. Sydney and Natalia went to bed naked again, spooning and holding each other just as close as the first night...

Sunday

Jack woke up well rested. It was about 12:30 pm and he was still pretty tired, he had a fun night. Jack stretched his body and let out a long breath. He hopped out of bed and opened his curtains. Jack stood in the window with his jaw dropped and his cock growing.

Sydney was outside tanning on the deck, topless. She was laying back in a sunchair in nothing but sunglasses and a bikini bottom. Her phone was playing music but it sounded muffled to Jack. Sydney looked absolutely perfect. Her tan boobs and her little brown nipples were glistening in the sunlight. She had oiled up her body before laying down.

Sydney's sexy legs and thighs were stretched down the sun chair. Her thighs looked extra thick pressed against the chair. Her dirty blonde hair was in her classic messy bun, her one arm was resting against her side while the other was on her toned chest.

Jack stroked his cock over his pyjama bottoms as he watched her. He wanted to take things slow today sexually, because he wanted to blow a big load for Sydney and Natalia.

Jack walked out of his room and downstairs. He went to the sliding glass door and peeked his head through. He recognized the muffled music as Lana Del Ray's "Doin time". A perfect summer time song.

Jack: "Hey Syd, where's Nat?"

Sydney didn't flinch or even try to hide herself. She sat up and leaned on her side to turn the music down.

Sydney: "Good morning Jack! Nat went out to get some groceries, she'll be back in a few hours!"

Sydney could see Jack checking her body out as he listened to her. She brought her knees up and slid her bikini bottoms up and down over her knees, then she grabbed them and flung them in Jack's direction as if she were flinging a rubber band.