Note: This story series includes depictions of gay and straight sex between teenagers. If that's not your thing or if it is illegal for you to read this story, then stop. This story is completely made up and does not depict anything true.
Comments, suggestions, and helpful feedback are welcome - e-mail me at DerekGuy17@gmail.com
Characters: Me: Jesse - 14, Freshman
My Sisters: Stephanie - 16, Sophomore Melissa - 18, Senior
My Sisters' Boyfriends: Lukas - 15, Stephanie's boyfriend, Sophomore (the twink) Shawn - 18, Melissa's boyfriend, Senior (the stud)
My Sisters' Boyfriends - Part 1 Saturday 2:53 p.m.
I was such a naive innocent. But that was my selling point that rainy night in December in Illinois. It was actually December 20. I remember it clearly, because my half-birthday was December 19. And when winter break had just begun I had just turned 14 and a half. Our folks had left in hurry for an emergency with my mom's sister Susan - they were decidedly vague on the details. Aunt Susan lived four hours away by car, so they were gone at least until mid-morning. This left the three of us - Melissa, Stephanie, and me - home alone for the night. At 18, Melissa was in charge and was told "stay home, no visitors, take care of your brother." She actually did 2 of the 3.
My sister Melissa was 18 and a slut. I know it isn't a nice thing to say, but the truth is the truth. I can't tell you much about when she started fucking around - I must have been 10 or so - but for as long as I knew something about sex, I knew my sister was doing it. She didn't simply sleep around. She wasn't that kind of slut most days. But she would date a guy for a while and engage in frequent, loud, and sometimes public sex. I came across her and several different guys doing all sorts of things in the living room, porch, her bedroom with the door open, once even in my bed. Ewww.
I guess that's how I knew I was gay. I mean, it is normal not to look at your sister, even when she has giant breasts flopping around like Melissa. But I was always staring at her boyfriends. Especially their hard cocks.
Melissa was quick to bed, but also quick to anger. Any guy that betrayed her was dumped. But if you cheated on her, you would suffer her wrath. Melissa's revenge varied, but it was harsh. And she had patience. She might make sure to break up the ex-boyfriend and his next girlfriend through some embarrassing rumor. She often would go to a dance or party with his best friend and make sure his friend got lucky in front of him. And sometimes she would do even more. When Ned Jenkins dumped my sister at junior prom in front of everyone, Melissa found her way into his house and took the virginity of his 13-year-old little brother Connor. I know because Connor is a good friend of mine. My sister is a slut.
My other sister Stephanie is well on her way to following our sister's lead. 6 months ago, Stephanie was a pretty reserved high school sophomore. But then "poof" - these magic lumps appeared "late" on her chest and a bra size or two later, she was a very popular young woman. She fell hard for a good looking senior named Andrew who thought he was tough and called himself Acid. Really, he was just Asshole. He treated her like garbage and one day kicked her out of his car in the middle of nowhere. Melissa then stepped in. Over her tears, Stephanie tried to talk her out of it, but older sister Melissa was livid. "Acid" really was part of a typical suburban family. With no younger siblings, Melissa did something totally new. Simply put: She fucked Acid's dad, intentionally got caught by his mom, claimed to be Acid's girlfriend, and implied that the Dad had fucked all of his son's girlfriends. Of course, it was all a lie, but the parents went at it and were now in horribly messy divorce proceedings. Ruined the whole family. A high price to pay for dumping your girlfriend on the side of the road.
A few months have gone by and my sisters are dating two nice guys. And that's my problem. I am so obsessed with my sisters' boyfriends. Both of them are really hot and friendly to me and seem normal and both feature heavily in my fantasies in my regular spank-a-thons.
Melissa and Shawn have been together for a couple months. He's 18, a senior, and major athletic force at the school. He has an outdoorsy look - the kind of guy who might drive a pick-up and chew tobacco if we lived in the south. He's well-defined, always smiling, and has let his medium brown hair grow a bit too long. Based on the sounds I hear, he liked rough, physical sex and based on rumor, he has an incredibly big dick.
Stephanie and Lukas have only been together a month, but I know they are already having sex 'cause I walked in on them accidentally (sort of). He is 15, a few months younger than my sister, but also a sophomore. He has soft, huggable looks, but a smile that when he turns it on you, makes you melt onto the floor. I know from seeing him "in the act" that he is mostly hairless, but has wavy hair that I think he should grow longer.
My parents hade been clear that they would be calling to check in several times and would want to speak to all three of us, so we better all be home. All of us complained to be in on a Saturday night although I had nowhere to go. The girls decided to make the most of having a parent-free house and invite their men over for some unpressured evening physicality.
"What do I get out of it?" I whined when told I'd need to stay out of the way and lie to our folks.
"Come on, Jesse. I'll look out for you," Melissa stroked my hair.
"Just help us out, Jess?" Stephanie had on her "puppy dog" look.
To be honest, my sisters were always great to me. They really looked out for me and tried to make my life easier. We rarely fought and I was a willing accomplice in their crimes because they were so good to me. I also knew that some of my popularity over the last couple years was my friends lusting for sisters. Melissa's deflowering of Connor only helped feed that fantasy.
Saturday 6:00 p.m. The boys arrived and we all ate pizza, Shawn drank a beer, they watched some TV, and hung out. Since they had the time - and since the girls couldn't leave the house anyway - they decided to just have fun and play Taboo. They even invited me play, but I was busy with our Playstation. I tuned them out for a while, but the tone of their conversation changed and made me perk up and eavesdrop.
"So what's the prize for winning?" Lukas asked seductively.
"What sort of things are you looking for?" Stephanie cooed back.
"Well, if we were already going to get it then it isn't much of a prize," Shawn declared. "I know what was coming tonight 'cause I brought my toothbrush. So it needs to be something extra. A bonus."
Melissa punched him and muttered something about not taking anything for granted. "Extra? Like what? A girl has limits..." Melissa retorted playing like she was Scarlet O'Hara. My sister has no limits and I tried not to laugh.
The boys whispered quietly to each other. I peeked over. They made an odd combo. Shawn was such a jock, while Lukas was twink-in-training and looked so much younger. But they shared a love of sex with my sisters and that was their decision.
"Promise you won't get mad," Lukas began.
"We won't," was the hesitant reply from his girlfriend.
"If we win," Shawn picked up the thread. "We switch sisters for part of the night. I go with Stephanie and Lukas with Melissa."
The girls both feigned shock. I know it was fake because I'd had seen them lie so many times in our lives and recognized their bullshit face. I knew they were both delighted with the perverse prize.
I turned back to the video game. Who cared who was fucking whom. Sluts. But then my name pulled me back into it.
"Jesse will go for it. He'd prefer it," Melissa was explaining. "Since we have you both at our mercy tonight, it has to be a prize we'd enjoy, but you might not want to do it."
"And besides," Stephanie concluded, "if it isn't Jesse than you have to do it with each other and we can make that a long night for sure."
"Both of us?" Lukas clarified.
"One of you tonight, before our fun begins, and the other later tonight or tomorrow morning."
I tried to work out what was going on. But as I was lost in the possibilities, Stephanie was suddenly by my side pulling me to the game. I was to serve as referee. Apparently, they weren't going to tell me the bet saying I had to be impartial.
The Taboo game was quite close. I figured my sisters were willing to swap partners regardless of the game's outcome, so they were better off winning, getting their prize (whatever it was) and claiming the boys' prize as well. They boys played hard. It was unclear if it was to win or not to lose, but Taboo works best when one is calm. Since the girls didn't lose either way, they had less pressure.
I had to settle a few disputes, but I was even-handed and fair. The boys had a small lead at the end when Shawn blurted out, "You know, Stephanie, if we win, I'm going in the back door. I want to be the first."
Stephanie and Lukas both got uncomfortable, but Melissa retorted, "And when you lose, you're going to be first on our prize. But think of it - you'll be the first."
Everyone but Shawn laughed. Melissa pressed on, turning to Lukas and saying, "And I expect a special treatment from you. Steph tells me you have a talented tongue. If you win the game, you better be prepared to get between my thighs." I just stayed quiet. It was better that way.
The game continued. Stephanie, who was giving the clues, went on an awesome run of getting Melissa to guess 8 cards and put them back in the lead. The boys couldn't catch up. They devolved into argued with each other over bad clue-giving, but the girls won by 9 points.
The phone rang. It wasn't our mom, actually, but our grandmother, also checking up on us and worried because she couldn't reach anyone at our aunt's house. We calmed her down (Melissa had a gift for that) while Stephanie served everyone ice cream with a happy smirk of victory.
To be continued...