Summer of My Discontent Pt. 01

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A sister. A bet. Regret.
4.8k words
4.46
14.1k
14

Part 1 of the 3 part series

Updated 06/09/2023
Created 06/12/2019
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God, I hate my sister. I mean, she isn't really my sister. Technically she is my step sister. But when my mom married her dad I was like seven and she was nine, almost ten. She made sure I knew that right away. Anyway, we have never gotten along very well. The first time we met she stole my Matchbox car. Seriously. It was a Batmobile replica Matchbox. It looked just like the Batmobile from the movie. I loved that thing. Some kids liked Hot Wheels, but I was a Matchbox guy. I guess that is beside the point. I was playing with it, minding my own business, and she walked up and took it. I told my mom, but she said I should just let her have it.

"It would be a nice thing to do for your new sister, don't you suppose?" I did not suppose. But I let her have it anyway. You might think things could only get better from there. You would be wrong.

Growing up she got everything. She could stay out later than me. She was popular, in that mean girl way. She got a car when she was sixteen! Guess when I got a car? Right after I graduated. And I had to pay for half of it myself. Fair? No. But that is how it is with Chelse. Did I mention her name is Chelse? Actually, it is Chelsea, but everyone shortens it to Chelse. Sounds like a cute, spunky name, right? Don't be fooled. I mean she is cute. Every single friend of mine has confessed to me at one time or another that they are in love with her. But that is the thing. On the inside, not so cute. She is only gorgeous on the outside. Five foot five. I don't even know what she weighs. Not a lot. Except for her top, which is heavier than it has any right to be, on account of her extremely large breasts. All my friends think they are fake. They are not. Firm? Yeah. Large? Absolutely. Fake? Nope. If you want fake, you are going to have to get to know her personality. That is where it gets fake.

She likes to tease my friends. I don't mean make fun of them to their face. I mean tease them because she knows they all lust after her. She will make sure she walks by us on the sofa dressed in whatever skimpy outfit she is wearing when she goes out with her friends. It is always something short and tight. It is disgusting. My friends have no chance. One of my best friends is a girl. Darby. I am pretty sure I have even seen Darb check out my sister. For a while each of them thought they had a chance. I tried to tell them it is not going to happen. They are all like me- into movies, video games, you know what I mean.

None of us are super smooth. So what? I have other decent qualities. I'm a good friend. Unlike most of the people I graduated with, I can keep a secret. My grades are pretty good. Not Valedictorian good, but...you know. Magna Cum Laude good. I got into the college of my choice. What a stupid phrase people tell you all the time. "The college of your choice." Yet somehow, all of those good qualities never helped me find a girlfriend.

I spent most of school crushing on girls that never seemed to notice me. Don't get me wrong. I don't blame them. I was pretty forgettable. And it isn't like they owed me anything. But I always wanted a girlfriend. I guess I was jealous of all the couples I saw. They seemed happy. School is kind of like that. The qualities that make you unique are often not appreciated in school. That is what Chelsea's dad told me one time. Oh yeah, did I tell you? Chelsea's dad is okay. Surprising right? His daughter is the worst, but he is a pretty good guy.

Anyway, that was how life was for me. Sister with everything. Me with nothing to complain about really. I just wanted more. Which is what made the past year so amazing. I guess I had one last growth spurt. That is what my mom said. Because going into my senior year, I grew a couple of inches. Topped out at six flat. I let my hair grow a little longer. Last summer I started running. Nothing too competitive, but I hear the fresh air is good for you. Turns out there is a world outside of my basement. And about three months ago, I met a girl.

Okay, I didn't really meet her three months ago. We went to school together since she moved here in third grade. But we never really knew each other. We had a couple of lecture classes together over the past few years, but never talked or anything. Then, the last semester of our senior year of high school, we both took an astronomy class. The class required these late-night labs at the park by the school where we were supposed to meet and learn to use telescopes, watch for meteor showers and stuff. We started talking at one of the labs, and the next time we had a lab, I noticed she just happened to join my group. It was awesome. We talked. She smiled at me. Rigby. That is her name. Cool, right? Her parents are kind of hippies I guess. They love The Beatles.

She is so good looking. My friends like to say she is out of my league. Dark, naturally wavy hair. At my school, blondes are everything. All the guys are crazy about blonde girls, even when they are not that nice. Come to think of it, maybe that is why Chelse was always so freakin' popular. I think that is stupid. Pretty is pretty, regardless of the what color a girl's hair is. Sorry- back to Rigby! Dark hair, sort of a creamy complexion. She is energetic and funny. And forgive me for being crude, but she has the best ass I have ever seen. Seriously. It is perfection. Her breasts are medium. Not too small. Proportioned. She is gorgeous. For the past three months we have been pretty inseparable. Which brings me to last week.

Chelsea was back for the summer. She goes to a state school a couple of hours away. She blows into town whenever she needs something. Or when she is board. And for the summer. This summer I had not seen her very much. Mostly just coming and going. I have been out doing things before I head to college. And Rigby has been right there with me. But last Tuesday Rigby had a family thing. Her Aunt was in town, and she had to go out to dinner. I asked if she wanted me to come, but she said her Aunt was a nightmare, and she didn't want me to go through that. I was relieved. But now, I wish I had gone with her.

Instead I was hanging out at home. I was actually in my room reading. (Sue me. I like to read.) Chelse burst into my room, without knocking as usual, stormed over to my dresser and grabbed my keys. On her way out of the room, she snarled that she was taking my car. (I guess hers was in the shop.) Now any other time since I was seven I would have engaged. I would have yelled "No you are not!" or something stupid like that. We would have yelled and screamed. Finally, my mom would have ended it by telling me to let my sister have the car. I lose. The end. But not this time. Because the only way to win the war, is to not fight it. I think Sun Tzu said something like that. I told you, I read.

Anyway, I just sat there on the bed, and as she left the room I think I said "Sure. Have fun." She poked her head back into the room.

"What?"

"Have fun" I said. Not a hint of sarcasm. Hey, I was in a good place. Life was good. She needed the car.

"What's your deal?" she said.

"Nothin. I don't need it. Have fun."

"Wow. So grown up." she said, dripping with sarcasm. "You don't mind if I take your stuff?"

I said "Honestly, no. Go ahead. I am good." She somehow knew exactly what I meant.

"You finally get a girlfriend and now you are...what? Zen master?"

"No," I said. "I just don't want to fight with you. If you want the car, take it." She glared at me out of the corner of her eye.

"I will take it. I'll take anything I want." She meant it too. And that is when I made a mistake. I should have kept my mouth shut. I didn't.

"As it so happens, the only thing I want is what you can't possibly have." And there it was. My mistake. Did you hear it? Pride? Confidence? Stupidity. Chelsea heard it, loud and clear.

"You don't think I can get her? Your dumb little girlfriend with the ass?" She noticed my girlfriend's ass?

"She isn't dumb, and no. You can't. You can take the car." She laughed a little. It was a weird laugh. I think she was caught off guard. She left, squealing the tires a little for my benefit as she pulled away.

I fell asleep reading, only to have my door burst open sometime around 2am. It was my sister. She came storming in. I thought she was going to apologize for being such a shit earlier. Will I ever learn?

"You don't think I can do it, do you?"

"Do what?" I said.

"Take this little girl from you. What's her name?"

"Her name is Rigby."

"Rigby? Stupid fucking name. Well little brother, I have one last lesson for you before you go to college. I am going to fuck little Rigby."

"What?" I was still groggy. Seemed like Chelse had been drinking.

"You heard me. I am gonna fuck her so good. She is going to eat my pussy until I cum all over her mouth. That same mouth you kiss. And there is nothing you can do about it." Nice, right? My sister. By now I was waking up. But I decided not to fight again. In retrospect, that was probably what was bothering Chelsea so much.

I just said "Okay. You're right. Goodnight." That was when things got nasty. She got right up in my face.

"I'm serious. I am gonna do it."

"No, you are not. It isn't even up to you. Or me. It would be up to Rigby."

That is when she looked at me right in my tired, heavy eyes and said, "Bet."

"What?"

"Bet me."

"No."

"Because you know I can do it. That is why you won't bet me."

"You can't take her because she isn't a thing."

"Fine. Use whatever word you want to use. I'm going to fuck her either way, but if you don't bet me then you will never know the truth." I gotta hand it to her. She knows how to push my buttons.

"How will me making a stupid bet- that I would win, by the way- help me know the truth. You could just lie. We both know you lie." She was actually quiet for a minute.

"You can watch."

"Watch what? You making a fool of yourself?"

"If I lose, yes." Damn, she kind of had me. I would love to watch her humiliate herself.

"Fine. How do you want to do this?" She thought for another minute. It looked like she was going to say, "just kidding" and leave the room. That is totally a thing she would do. But she didn't.

She said, "This weekend your mom and my dad are gone, right?"

"Yeah. Just one night though."

"Saturday? Perfect. Saturday night, at midnight, be in my closet. And turn your fucking phone off. You can't make a noise. Not a single noise." With that, she left the room.

At breakfast the next morning, she seemed her normal, obnoxious self. I almost thought she forgot about our conversation completely. But right in front of my mom, she leaned over whispered in my ear "Saturday. Midnight. Not a sound."

I would be lying if I said I was not worried. However, I still thought it was a real longshot. First, Rigby likes me. We have not said the "L" word yet, but I think she is as into me as I am into her. Also, she is cautious. We have made out a thousand times. But we have not gone too much further. I have touched her a lot- over the clothes. Whenever things get a little hot, she always pulls away and says we are going a little too fast. So even if my sister was convincing, I still didn't think she would be able to get very far. That was my ace in the hole.

At about 11:30 pm Saturday night I went into my sister's room. It was clean for once. The bed was even made. I went into her closet. There was a stool waiting for me. How thoughtful. The closet has louvered doors, so it is not that difficult to see most of the room. And I actually had a good view of her bed. The bedroom was lit, but the closet was not. So, I imagine anyone in the room would not be able to see me. Sitting there waiting I started getting nervous. Earlier in the day I asked Rigby what she was doing that night and she said she was going to hang out with a new friend. When I asked her who, she only said she would tell me later. I begged. She said that it was a secret for now. How my sister manipulated Rigby into keeping their evening from me, I don't even want to know. After a few minutes in the dark, I heard giggling from down the hall.

The door flew open and my sister was the first thing I saw. She was wearing a form fitting sundress. It was tight around her tits. Surprise there. She was laughing as she came in and flopped on the bed, looking at her phone. A moment later Rigby appeared at the door. She was laughing too. Rigby looked amazing. She was wearing jeans that fit so perfectly. She had a small black t-shirt on. Form fitting, without trying too hard.

"Come on in," my sister said.

"I've been over here a bunch, but never in your room."

"Well, here it is." Rigby sat on the corner of the bed at Chelse's feet. Just as Rigby sat down, Chelsea put down her phone and looked straight at me. Well, not necessarily at me. At her closet. So, yeah, right at me. She was smiling right at me. She was enjoying this already.

"Thanks for inviting me out with you tonight."

Chelsea, looking right at me said "I thought it would be great for us to get to know each other."

"That is what I think too."

"My idiot brother thinks I don't like him, but I only want the bet for him."

"You mean the best?"

"Yes, the best. I must have had one drink too many!"

Rigby got up and started looking around the room. There were a couple of bottles of perfume on my sister's dresser. She held one up to her nose and said, "I like this one."

"Me too. I have been wearing it all night. Here, come smell it on me."

"Oh, um, okay." Rigby was already pulling back. Chelsea was too blunt. Too strong. But to my surprise Rigby did go over sit next to my sister. My sister sort of leaned in and offered her neck to my girlfriend. Rigby met her half way and took a long breath in. It was the first time they were in each other's space, and I admit I thought Rigby seemed attracted.

"Isn't that nice." said Chelsea.

"I like it a lot!"

"I know right. You can borrow it. It would smell great on you. Are you wearing anything?"

"Yeah, my perfume is a little more...subtle than yours, but I like it." Without being invited, Chelse grabbed my girlfriend on both shoulders and pulled her close, inhaling deeply.

"You are right. It is subtle, but fantastic. I bet guys like that. I have to admit, it turns me on!" And at that moment my sister kissed my girlfriend.

It was on the neck. It was a soft, gentle kiss. I wouldn't have thought my sister was capable. It almost seemed like it had actual, human emotion behind it. But then, just as it began, my sister pulled away. She looked at Rigby and started shaking her head.

"Oh my god, I am so sorry. I didn't mean to do that." Rigby was caught off guard, but she is such a nice person that she didn't want my sister to feel bad or embarrassed. Can you believe that? She tried to make my sister feel better. I actually made a sound. It wasn't loud. I think I exhaled in disgust. I doubt that Rigby noticed. But Chelsea did. She got up and walked over to the closet, like she was turning her back on Rigby, but it was really to give me a look. I knew the look well. She had given it to me a thousand times. Shut the fuck up. That was the look.

Rigby came over to her. She turned Chelsea around so they were face to face.

"It is no big deal. You probably did have one drink too many. No-one will ever know." Chelsea gave Rigby the biggest hug. They were about two feet away from me. When she pulled away, it was slowly. Their faces were right next to each other, staring into one another's eyes. And that is when it happened. Chelsea just stayed there, looking hurt. Wounded. Big eyes. Longing. They were so close to each other. Then Rigby kissed her. Not the gentle peck on the neck Chelse did. No. This was forceful. On the lips. There was tongue. My evil sister and my gorgeous girlfriend were making out. I was horrified. Angry. But I couldn't take my eyes off of it.

Chelsea guided Rigby over to the edge of the bed and set her down. Then, Chelse got on her knees. Although she couldn't see me, Rigby was looking right at me. All I could see was my sister's back, but it seemed clear to me that as they were kissing, my sister's hands were covering a lot of ground. They finally focused in on Rigby's tits. And then Chelse started pulling Rigby's t-shirt over her head, revealing a little black bra. Two seconds later, the bra was undone and slipping off of Rigby's sexy shoulders. Jesus, that was fast. How many girls had my sister seduced? She always had boyfriends. So confusing.

Believe it or not, this was the first good look I ever had of my girlfriend's tits. They were awesome. Relatively small, dark nipples. What her breasts lacked in size, they made up for in perkiness and shape. They were exquisite. My penis started getting erect fast. Meanwhile, my sister started licking her tits. Rigby started to make little sounds. Moans? Just little ones that told me that she was enjoying my sister's tongue on her nipples, which were already extremely hard.

At this point, my sister was already getting restless, because she started working on the button and zipper on Rigby's jeans. And here is where Rigby stopped her cold.

"Wait. Wait. We can't do this."

"Why?" Chelsea sounded hurt. Rejected. Believe me, it was a total act. As excruciating as this whole thing had been, I was about to win.

"I have never gone this far."

"Seriously? Not even with..."

Before she could finish the question, Rigby said "Not with anyone."

"Well, that is okay. I would like to teach you. Can I teach you?"

Say no. It is easy. Just say no. SAY NO! Okay, I wasn't really screaming. But I was in my mind.

And then, to my horror, Rigby said, "Okay."

"Okay what?" Chelsea said with a sexy grin.

"You know."

"No, I don't know anything. Okay what?"

Giving in, with an embarrassed smile; "Okay, please teach me." Crap. I was going to lose.

Chelsea held her face in both hands and gave Rigby a deep, long, draining kiss. If Rigby had been standing, her knees would have gone weak. And with one smooth move my girlfriend's jeans and panties were resting at her feet. Another first for me. It was the first time I had ever seen her pussy. Dark hair. Not too much. The folds of her skin were, how can I put it? Dark. I am not real experienced, but I thought her dark pussy lips were sexy as hell. As my sister slipped the jeans and panties off of Rigby's feet, she turned to throw the discarded clothes in the corner of the room. It was just an excuse to face me. She was smiling. She knew that she was about to touch my girlfriend in ways I had not. FUCK! I hate her so much. If you could have seen the look on her face, you would hate her too.

Chelsea came back to Rigby's feet and spread her legs wide. I could just barely see Rigby's pussy as it opened, revealing the pink folds beneath the dark edges.

"I'm scared."

"Don't be. I am going to make you feel so good." And with that, my sister began to eat my girlfriend's pussy. Slowly at first. I think I could tell the exact moment Chelse's tongue touched Rigby's pussy because Rigby's eyes rolled back into her head and she let out a gasp. I guess it felt pretty good. Soon my sister was working her tongue quicker. Rigby's breathing went from even, deep breaths to short, faster ones.

"Oh god. Oh god. That feels really good. Have you done this a lot?" My sister's hand came up to Rigby's mouth and shushed her. Then she reached up with both hands and started rubbing Rigby's nipples between her thumbs and forefingers.

Apparently, this was just the right move, because Rigby started moaning loudly, involuntarily groaning as she ground her pussy on my sister's mouth. And then, all at once, Rigby's toes curled, and she flexed every muscle in her body at the same time. Then again. Then again.

Finally, she said "Stop. Stop. Oh my god. It is too much. Stop."

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