Sister Steals Brother's Virginity

Jack has had girls chasing after him his whole life. He's had plenty of girlfriends and sexual encounters, but he's never gone all the way.

This is the story of when Jack had sex with his sister and her friend. Jack was 19 at the time, a fit, attractive male with a huge dick, at least 8 inches.

His sister, was 20, she is also fit, (both of them were involved in school sports) she has big breasts, not saggy, not perky but they hang and they're super nice, she has a cute ass, not big not small, and her hair is brown.

Jack's sister's friend was also 20, she's blonde, dropdead gorgeous, c cup boobs, and a perfect ass, but I'll talk more about her later.

Jack's sister is named Natalia, and Natalia's friend is named Sydney.

Jack's family is middle class. They live in the U.S, they're a pretty attractive family, the mom's 46 and looks about 34, the dad's muscular and gruff looking. Jack's parents aren't involved in the story that much tho.

Jack has always been attracted to his mom and sister, something about them always turned him on. Jack spies on his mom and Natalia whenever he can. Getting changed, showering, swimming in the pool, even just watching them walk, their boobs and asses would bounce and it always filled him with adrenaline to see that.

He'd frequently masturbate to his mom and Natalia but he never thought about actually having sex with either, not because he didn't want to, it just somehow, slipped his mind.

Jack's parents were going out of town for a bit. They were giving Natalia a nice long vacation to hang out with her friend Sydney, because the two wouldn't see each other for a long time by the time school started.

They were best friends so Jack's parents felt bad they wouldn't see each other for a while. Now for context, Jack fucking LOVED Sydney. She's been friends with Nat since kindergarten, the first day of school pretty much. Jack's known her for a long time and she's by far his favourite out of all his sister's friends. Jack's been head over heels for her since he met her.

Jack: "I genuinely think she's the most beautiful woman I've ever seen. I think Sydney is just so unique, and I mean that in every way. Her voice is angelic, she has the slightest lisp and I think it's adorable, like very slight, the kind she has to tell you about for you to actually notice. She has the kindest and biggest smile, and the most gorgeous eyes. To quote Billie Eilish, Sydney has those "Ocean eyes". They're bright blue and mesmerizing to look at.

Her physical body is also very unique. I don't know how to describe it. Like her body structure is so god damn beautiful, and sexy. She's slim and fit around the waist, then you go down and she's thick as fuck.

Her body is so curvy (except for her c cups) but her ass, my god her ass. That's the most unique part about her. It's like, fucking big, but not big enough that it looks weird or fake on her.

You'd have to see it to understand but my god it's amazing. It's so real and amazing. Her thighs tho, they're so perfectly juicy and thick. She has little hip dips that are so sexy. Not in anyway overweight tho, she's in perfect shape, she's just so god damn thick, with an ass just right for her."

Sydney's gorgeous body was only an added bonus for Jack, he loved her for who she was. And who she was was a bright, kind, smart and beautiful young woman. She never failed to put a smile on Jack's face with her great sense of humour. So Sydney, Natalia, and Jack were going to be spending about 4 days together with no one else around.

Thursday

So it's Thursday morning, Jack's parents had left early in the morning. It's about 11:00 am, Nat and Jack are watching TV in the den, waiting for Sydney to arrive. So Sydney rings the doorbell and Nat runs to the door, they hug each other and talk for a minute or two. Sydney and Natalia were the best of friends. They loved each other very much, people often mistook then for a lesbian couple, this always made them laugh.

Nat then lead Sydney upstairs to let her drop her bags off in Nats room. Then they came back down to see Jack.

Natalia: "Jack Sydney's here!"

Me: "Hey Syd!"

Sydney: "Hey Jack! What's up?"

Me: "Nat and I were just chilling watching tv."

Natalia: "Wanna watch tv for a bit Syd?"

Sydney: "Sure why not."

The girls came into the den and sit down. Jack's facing towards the TV, back against the couch, Sydney comes and lays down beside him, with her head on the arm rest, (if she were to stretch her legs out they would land on his lap, just to give you an idea of how she was sitting)

Nat sits on the other couch and they all get sucked in to the tv. Jack was ecstatic Sydney chose to sit with him. He glanced at her a number of times while they were all watching TV. She was wearing ripped jean booty shorts, and a white tank top. Her hair was in a dirty bun as it normally was. She had her knees up and her legs were pushing her pussy and making it tight against her shorts.

Jack could clearly see her pussy and it was turning him on, even though her shorts weren't see through. Sydney is also tan by the way, not too tan but you know she's not pale. It was a hot summer day so after about 30 minutes since Sydney arrived, Natalia said...

Natalia: "Jesus it's hot, do you guys want to go for a dip in the pool?"

Sydney: "That would be amazing right now, I'm so damn hot"

Me: "Yeah sure why not"

Jack was trying to hide his excitement because not only did he get to see his sister in her bikini, he got to see Sydney in hers! He's seen her in one before but not since she got a growth spurt and she started to develop.

They headed upstairs to change. Jack got changed the fastest and when he was done he started to head downstairs but he just couldn't resist taking a peek at his sister changing.

Nat was in her room and Sydney was in the bathroom changing. Now Jack would've checked out Sydney but Nats door was cracked open a bit so it would be easier to spy on her.

Sure enough, Jack got an eyeful of his sister. Jack caught her just in time. She slid her shorts down and then her underwear. Her shaved pussy was now in sight and his heart quickened. Then she took her top off, and then her bra. Her luscious tits slid out gracefully and they bounced as she put her bikini on. She stripped off as if she was in a movie, or a porno, so slowly and sexually.

He heard the bathroom door unlock so he ran back downstairs and sat on the couch. Jack pulled out his phone and started to record the stairs, he acted as if he was playing a game, though secretly recording still. He was recording because he wanted to get a good shot of Natalia and Sydney in their bikinis so he could jerk off to it later.

Sydney came down the stairs in her blue bikini. He could tell she was eyeing his chest, specifically Jack's abs. She looked spectacular, her tan body strolling down the stairs as her thighs and ass shook a little with each step down. Not to mention Sydney's toned, sexy chest, Jack loved looking at her belly ring, among other things.

This was by far the most exposed Jack had seen Sydney and it felt as if he was staring at her for hours. He wished so desperately her thin 2 piece would vanish right off of her sexy body. Not to mention her body looked all oiled up because of the heat.

Sydney: "You stole my seat you dork!"

(She said in a flirtatious way)

Me: "Sorry I'm faster than you at getting changed loser"

(He replied in a flirtatious way as well)

Jack and Sydney were always flirting with each other, even since they were young. The two loved teasing one another. Sydney just smiled and sat down so their bodies faced each other, and went on her phone as the two waited for Nat to come down.

Sydney adjusted the way she was sitting to the way she was before. And again her tan, thick legs pushed together and tightened her pussy so now Jack could make out her slit and he started to get a semi. He made sure he was recording what he was seeing and looked away as to not get a full hard on.

After a minute or 2, Natalia came down and looking just as sexy as Sydney, she was also super sweaty and her boobs were basically spilling out of her red bikini.

Natalia: "All set?"

Sydney: "Yup"

Jack followed the two out to the backyard and to the pool. All the while getting a good long look at both his sister, and Sydney's asses bouncing with each step.

When they got to the pool Sydney undid her bun and let her gorgeous hair down. She dove in the pool without wasting a second. Natalia was about to hop in but Jack decided to push her because he wanted to cop a feel...

Me: "Hey Nat!"

Natalia: "Wha-"

Jack brought both his arms out and pushed her into the pool but he placed his hands almost directly on her boobs! She made a splash and then resurfaced.

Natalia: "I hate you so much Jack"

(She said while trying not to giggle)

Sydney: "Haha nice one Jack!"

He stood at the pool edge and smiled at his sister. And to his surprise his sisters tits were out! Her nipples and about half of both of her tits slid out of her top when he pushed her in. Nat didn't see at first but Sydney saw Jack's jaw drop, and his dick get hard.

Sydney: "Nat your boobs are out!"

Natalia: "Oh shit! Jack I'm gonna ki-"

Natalia stopped as she saw Jack's now hard dick in his swim shorts.

Natalia: "EWWW wtf I'm your sister!"

(She said while crossing her arms while trying to cover her tits)

Me: "For fucks sake! Sorry but I can't help it!"

(Jack said while trying to cover up, not really caring if they saw though)

Sydney remained quiet.

Natalia: "I'm your sister you perv, how can you get turned on by me??"

Sydney: "Nat cut him some slack, he's a guy going through puberty. If he sees a nice pair of boobs he's gonna get hard."

Sydney was sympathetic to Jack but she didn't know of course that Nat seeing his hard on just turned him on even more.

Natalia: "Okay yeah your right. But can you at least get rid of it Jack?"

Sydney: "Well I don't mind as much as your sister Jack, but I'm sure Nat doesn't want to see that."

Jack was turned on even more now after hearing Sydney say that.

Me: "How am I gonna get rid of it? I'm as hard as I've ever been right now."

Natalia: "Idk go, go inside and jerk off"

Jack started to walk away, but then stopped. He turned around and said...

Me: "What if-, what if I jerk off here?"

Natalia: "excuse me?"

Me: "If I sat here and jerked off it would go away much faster."

There was a long pause, in this pause, Nat had an uncertain look on her face and Sydney looked intrigued as to what was going to happen next. Nat looked at Sydney and Sydney said...

Sydney: "I mean, I'd be ok with it if you are Nat..."

Another long pause followed by Jack's sister lowering her arm from her chest, and putting her bikini back on, and saying...

Natalia: "Fine. Sit on the sun chair and jerk off. But you better be done in 2 minutes!"

So Jack took his hand away from his crotch and the girls stared shockingly at his boner. He slid his shorts off and both of their jaws dropped. Jack's callosal cock dropped and swung in front of the girls. He started to get cocky and walked with confidence to the sun chair and sat down. Jack spit into his hand and started to stroke himself off.

They tried not to watch but just like the tv, they got sucked in to it. They stared at him stroking his cock up and down not saying a word. While they watched him, Nat and Syd both touched themselves, not masturbating, but they slightly squeezed their boobs and rubbed a hand across the front of their pussies. They were fidgety. Jack could tell they were getting horny because of this.

By the time he was ready to cum, their nipples were hard as rocks, they looked as if they were about to pop from their bikinis, and they were still caressing themselves. Jack couldn't take it anymore and he blew his load all over the chair and a bit on the ground. The girls stood in the pool and just watched as he tried to catch his breath.

Jack cleaned up and put his shorts back on, they swam for about an hour. It was pretty quiet overall. Jack's sister looked as if she'd seen a ghost.

For the rest of the day, Natalia kept losing focus, and her attention to most things. She frequently "stared off into space" as they say. It was clear she had mixed feelings about what had happened. She clearly enjoyed it at the time, but now she had come to her senses.

I mean, Jack was her brother, and she just watched him masturbate in front of her, she liked it, but she shouldn't like it. It's wrong...

That night as the 3 of them were finishing up a movie. Sydney texted Jack even though she was right beside him, just so Natalia couldn't hear her...

Sydney: "Jack, stay down here after the movie, we need to talk"

They both gave each other an agreeing look and nod and then proceeded to watch the rest of the movie. When it ended, Nat stood up with Sydney as they were headed to Nats room for the night. Sydney quickly stopped and said she was gonna get a glass of water. When Nat got to the top of the stairs and out of sight, Sydney came over to Jack on the couch.

Sydney: "Hey Jack, so about today, I honestly don't even know how that happened. It all felt so fast, I mean Nats boobs were out and the next thing I know we were watching as you masturbated. Now I obviously enjoyed it, I mean my eyes were on your- your dick, the whole time. I'm sure you noticed. But Natalias really shook up about it."

Jack started to blush and he straightened himself out as Sydney finished speaking. Hearing how his longtime crush liked seeing him stroke his cock was amazing.

Jack: "Yeah I can tell she's distraught. It was a weird thing for me to suggest doing I'm sorry. I shouldn't have done that, I need to talk to Nat."

As Jack started to stand up Sydney stopped him.

Sydney: "Wait Jack! Sit back down for a sec."

Sydney then noticed Jack's semi erection in his pants. Jack blushed even more and covered himself as he sat back down while trying to avoid eye contact.

Sydney: "I'll talk to Natalia tonight, she'll be alright by the morning. But as for you,"

Sydney placed a hand on his leg, and seductively smiled into his eyes.

Sydney: "You better get rid of that before you head upstairs"

She said as she eyed Jack's erection. Sydney gave Jack a quick kiss on the cheek, and giggled in his ear. Syd headed up stairs.

Jack couldn't believe the day he was having. Once again he was fueled with adrenaline and was very horny. He took out his phone and found the videos of Nat and Syd in their bikinis. He found the one specifically of Sydney's pussy pressed against her bikini. He took out his cock and stroked off right in the living room. He came very hard and then cleaned himself up.

As he walked upstairs and past his sister's room, he stopped because he heard the girls talking. He knelt down towards the floor and listened from under the door. Sydney was looking for her phone charger in her bag and Natalia was sitting on the bed.

Natalia: "I've been thinking about what happened all day today and I still have no idea what to think about it. I mean, he's my brother, but his cock is huge, he's my brother, but he made me so wet in the swimming pool, but he's my brother! What do I do Syd?"

Sydney: "Listen, I had a talk with Jack after you left."

Natalia: "You did? About what?"

Sydney stopped digging in her bag and sat on the bed next to Natalia.

Sydney: "Just listen, I told him that you were distressed about what had happened. He said he could tell you were freaked out about what happened, and he felt bad."

Natalia: "Well I'm glad he's sympathetic at least."

After a period of silence, Natalia spoke...

Natalia: "I mean, it's not that I was shocked about him masturbating, I've seen him in his room before, it's that it turned me on! Like for the first time in my life I've wanted my brother sexually. And I hate even saying that out loud but like, did you see his cock? That's the first time I've ever gotten a good look at it."

Sydney: "It was sooo nice right? I mean he's cut, it's at least 8 inches, and it's thick. It's making me wet just thinking about it!"

Natalia: "Yeah me too, like really wet"

The girls looked at each other and giggled,

As Jack stayed quiet in the hall, his heart began to pump faster and faster as he listened deeper to the conversation. Inside Natalia's room, Sydney and Nat were still talking about how turned on they were.

*Silence*

Natalia: "Sydney, we've both seen each other nude lot's of times right? Would it be weird if I said I wanted to- I wanted to masturbate with you? -Like we don't have to touch each other if you don't want to, but I want to do it together, in front of each other."

*Silence*

Sydney: "Considering how wet I am, I'm gonna have to masturbate tonight, so we might as well do it together."

Natalia and Sydney both got up, and stripped down in front of another. Now they've done this many times in front of one another, you know, changing for the pool or beach or in a changing room at a store.

But this time, this was the first time the two really looked at each other. They admired each other's bodies and curves. They got excited to see the other naked. This time, for the first time, Sydney and Natalia were turned on by seeing one another naked...

As they finished stripping, Natalia went to her door and dimmed her lights, she also made sure her door was locked. Hearing his sister come to the door and then shake the door knob to check if it was locked startled Jack. He stood up and lightly ran to his room and shut the door behind him in fear of getting caught.

Once Natalia made sure the two were completely alone, she sat down next to Sydney and the two started to caress their own bodies. They squeezed their boobs and pinched and pulled at their now erect nipples.

Their hands made their way down their bodies almost simultaneously and they started to touch their soft, soaked pussies. They slid their fingers down their slits and spread their lips. After feeling how wet she was, Sydney then brought her finger to her mouth, where she sucked her finger clean.

Shocked yet intrigued at the sight of this, Natalia rubbed her fingers around her own pussy, and then tasted herself, just as Sydney had done.

Natalia: "I've never done that before!"

*Silence*

Sydney: "Mind if I have a taste?"

Natalia smiled and nodded cheerfully. Sydney brought her hand to Natalia's pussy and slid her fingers about her lips and her clit. She made sure her fingers were dripping, and then she stuck each finger in her mouth and tasted her friends pussy juices. Sydney, sucking each finger dry then started to rub her clit in a circular motion. Natalia did the same.

As Sydney started to moan quite loudly, Nat put a hand on Sydney's mouth and whispered to Sydney to remind her that Jack might hear them. Sydney continued to masturbate with Nats hand covering her mouth. Nat also continued to masturbate and as she moaned, Sydney used her free hand to cover Nats mouth.

So Natalia and Sydney both sat, side by side, touching themselves, rubbing their tight wet pussies and covering each other's mouths to muffle their roaring moans.

As the two both neared climax, the two looked at each other and stuck their fingers in each other's wet pussies. They fingered each other, their backs arching and goosebumps running all down their bodies.

As they orgasmed they felt as if they couldn't breathe, they tried their hardest not to scream with pleasure. This was the hardest and biggest orgasm either of them have ever had. They both came very hard, while their cum oozed out of their pussies.

Sydney took her now fresh cum and rubbed it on her nipples, she told Nat to lick it off. Natalia, without hesitation, leaned in and sucked and licked Sydney's nipples.