Summer Of My Discontent Pt 03

This is the third part of the Summer of My Discontent series. I recommend reading Part 1 and Part 2 before reading this. Part 1 is located in the Lesbian category. Part 2 is located in the Toys & Masturbation category. Enjoy!

*

God, I hate my life. I had fallen asleep by the time Darby knocked on my window. It scared the crap out of me. Why was she knocking on my window anyway? I mean, it was late, but not that late. And she knows we usually don't lock the front door until the last person goes to bed. I looked over at the closed door to my room and saw light coming in from the hallway. Someone was still awake.

"What are you doing?"

"I told you I would be back tonight." She was in a mood. I could tell instantly.

"Yeah, but I thought you would use the front door?"

"Then no one would think we have a secret."

"We want someone to think we have a secret?"

"Shut up and help me." Right. She threw one of her sexy legs through the window and then held her arms out at me to pull her up and in. She wasn't wearing her usual hoodie and leggings. What the hell was she wearing? A robe? She was wearing a backpack and a robe. She looked like a college student initiating into a cult. This kept getting weirder. Honestly though, I didn't care. I was glad to see her. My day seemed endless from the moment she left till now.

"What's in the backpack?"

"Not important. Here." She tossed me my phone. I wasn't sure I wanted to know the answer to my next question.

"Is it still on there?" She knew what I meant. The picture. She turned toward me. I got a good look at her. She looked beat. Her face was flushed. Her hair was matted down. It looked like she had come over here right after a serious workout.

"Yeah. It is still there. I'm not gonna tell you to stop looking at the picture of your girlfriend licking your sister's clit. But you know, you might want to start weaning yourself off of it. Believe me, I get it. But you might want to start."

"Why did you need it?"

"Clearly I needed to work some things out."

"Oh...how many times?"

"I didn't count."

"How many?"

"Five. Six if you count the first time here. I am sore and frazzled. None of them were as intense as this afternoon with you telling me the story. But I just couldn't stop all day. I basically haven't left my bedroom. I don't know what it is. But there is something about your sister's body that just..."

"I understand." I paused. Then I went for it. "Are you a lesbian?" She punched me. Not really too hard. In the arm. But she punched me.

"Don't be so...binary. I like guys. I like guys a lot. Sometimes I think about girls. When I do, it is almost always your sister. I have watched her walk by us on her way out of your house for years."

"You got me beat there. I never used to think about her. Until the other night. When she took off that dress and I saw everything, it was...something."

She looked sad for a moment. "I know," she said. "That was her plan."

"I'm pretty sure her plan was to take Rigby away from me. She has always loved taking my things. It was just a matter of time until she took something I really cared about."

Darb thought about what I said for a moment. "Look, I am sure you are right- and she always used to take your things. But I think Chelsea wants you. I think she has probably wanted you for the last year or so. I think she wants you so bad it is killing her. And I think she wanted to hurt you because she is angry and embarrassed about how much she thinks about you."

"For the past year or so? How the hell would you know that." Darby's eyes flashed with anger. She pushed me against my wall. She is stronger than she looks. She got right in my face.

"Because that is how long I have thought about you." I was at a loss. What? Darby made it clear she didn't want me years ago, and just today when we could have done anything together she doubled down on that.

"You...like me? But you are into my sister. That is pretty obvious."

"I want her, sure. More than I have ever wanted someone. But I don't like her. No offense, but she is awful. She is mean. Rude. Selfish. But the way she looks when she walks through the room. I think I might want her more because she never gives me the time of day. I have to get those tits in my mouth. I have to taste her. Seriously though, the thought of talking to her afterward is repulsive."

"If you feel this way, why didn't we do anything together today? It didn't seem like you wanted me."

"Well, not like this I don't. You are crushed about your girlfriend and obsessed with your sister. And I get that. I am too. So... forgive me if I don't want you in exactly the state you are in now." As usual, she made sense. I wouldn't want me like this either.

"Just- trust me, it was probably about a year ago when she started noticing you."

"I guess my life is really messed up." I said. She smiled. The anger was gone. She gave me a peck on the neck.

"I know. Now, we know what I spent my afternoon doing. What did you do since I left?"

"Not much. I had a long list of chores to do before Chelse's mom gets here Friday. I mowed the lawn, cleaned the pool. Crap like that. Oh, I did talk to Chelsea for the first time since...you know."

"Did you talk to her first, or did she talk to you?" Darby was getting intense.

"She talked to me."

"When?" I flopped onto my bed.

"When I was cleaning the pool. After I was out there a few minutes she came out and sat on one of the sun chairs."

"Does she do that a lot?"

"All the time. There was nothing unusual about that. Most days she lays out for a bit."

"What did she say?"

"She started with some general taunts. 'Haven't seen you in a few days? What closet have you been hiding in?' I just tried to ignore her. Then she asked about you. She asked where my little friend went this morning. That was a little unusual I guess. She doesn't usually ask me about my friends."

"I'm probably the reason for that. On my way out today, I kind of acted like we were up to something. When I left your room, I leaned against the outside of your door, like a little love-struck puppy. And then, I walked in a daze out the door. I didn't say anything to your family. I didn't even look at Chelsea. If anyone was paying attention, they definitely thought something was up." She kind of giggled. I think she was kind of enjoying this.

"What made you do all that?"

"I don't know. I was improvising. I guess I didn't want your sister to think you were hung up on what happened the other day."

"But I am."

"I KNOW THAT. But I didn't want her to think that. You know, if we are gonna do this, you have to start thinking more like her. Manipulative."

I was afraid to ask. "Do we have a plan? Or are you just going to keep improvising?"

"Sort of. During my...alone time...today I remembered something your mom said. She was talking about Chelsea's mom visiting, and she said how much it meant to Chelsea, right?"

"I guess."

"That is good for us. Chelsea actually cares about something. We can use that."

"How?" She took a breath. Paused. She looked right at me.

"I think you need to fuck Chelsea's mom."

"Pardon?" The words honestly made no sense to me.

"I think you need to fuck Chelsea's mom, while Chelsea watches from the closet. I'll probably be in there too, come to think of it."

"You have lost your mind. I think looking at that picture all day made you crazy. Even if we could somehow make those circumstances happen, I am not fucking Chelsea's mom."

"Why not?" she asked. A reasonable question.

"She is old." For one thing!

Chelsea just smiled. "When was the last time you saw her?"

"I don't know. Six or seven years ago?"

"So, you were like eleven."

"Or twelve maybe, why?"

"Because she isn't old. You were just...young."

"You need to see a doctor. You are not making any sense."

"Sure I am. Look, I friended Chelsea's mom on Facebook before I got here. Actually, you friended Chelsea's mom on Facebook. You never change your passwords, do you?"

"I don't go on Facebook anymore."

"But you know who does? Our parents. Chelsea's mom has an account, and she already accepted your request." Darby was already pulling out her phone and opening Facebook to show me.

"What is this going to prove?" I said. But Darby was finished arguing with me. She just showed me the phone. It was a picture of Chelsea's mom. Oh my. Chelsea didn't fall too far from the tree. Specifically, her peaches didn't fall too far from the tree. Chelsea's mom was hot as hell. Somehow Darby was able to locate a picture of Chelsea's mom at the beach, in a bikini. Thin and tan. The same tits as Chelse. The. Same. I was getting aroused. I pushed the phone back to her.

"That picture could be ancient. She might not look like that anymore."

"That picture was taken last Wednesday on a business trip to Los Angeles. I did a little Facebook research. She is thirty-nine. Chelsea is twenty-one. She and your stepdad must have been, like eighteen when Chelsea was born."

"He always talks about how "mistakes were made" in his first marriage. I guess that makes sense. But even if I could get Chelsea's mom to want to have sex with me, I see no possibility that Chelsea would watch from the closet. What kind of an idiot loser would ever agree to that. I mean, what would I say? Bet me your mom won't have sex with me? It is stupid. It won't work."

"Not like that it won't. You are playing checkers. We need to play chess. You have a piece on the board that Chelsea doesn't even know about."

"What's that?"

"Me dummy."

"Alright. Enough hinting. What is your plan?" I asked. And with that, she laid it out. When she finished, I just shook my head.

"Nope."

"What do you mean nope?"

"Nope. It won't work. I see why you want to try it." I said. She glared. "But realistically, I give it about a three percent chance. If that." Darby looked sort of crestfallen. Her gaze came to rest at her feet.

"You're right. Probably dumb." Hm. This might have been the first argument I actually won with Darb...ever. She is usually tenacious.

"We will have to fall back on your plan."

"I don't have a plan."

"I KNOW. So stop being a pain in the ass and let's get to work." She suckered me. She wasn't giving up at all.

"Fine. Let's do it. We are going to fail miserably. Your embarrassment will be moderate. Mine will be legendary. But what do I have to lose. I can't lay in my bed jerking off to a pic of my sister for the rest of my life."

"That's the spirit, I guess? And possibly one of the most messed up sentences anyone has ever said."

"Thanks. I'll see you back here tomorrow morning?" I said.

"Wait. We still have work to do. As I see it, I have one night to make sure you know what you are doing. And it isn't like I'm some kind of expert about this. But we can't have you humiliating yourself in the middle of the greatest revenge plot ever. So, get naked." But she didn't wait for me to get undressed. Instead, she dropped her robe, and I finally understood why she was wearing it.

She had nothing on underneath. My god, she was breathtaking. I almost forgot, even though it had only been since this afternoon. As great as she looked today, that was in a dark room. This time I could see clearly. My heart started racing. My palms started sweating. My cock was coming to life. I started taking off my clothes quickly.

"Are we going to do it?" I asked.

"Wow. Quite the romantic I see. No. But I figured that you might need to look at something to get you started. I am going to try to teach you how to last long enough to make a good showing." With that, she pushed me into my bed and laid down next to me. My cock was so hard it hurt already. I needed relief.

"I'm going to touch it. Let me know when you are about to cum so I can clear out." She reached down with her right hand and gently grasped my shaft. Her hand felt warm. And so freakin soft. She gently stroked it once."

"Remember, the goal here is to last as long as..."

"I am cumming."

"Ha! You are hilarious. But seriously, try to la..." That is all she got out before I exploded. It went all over her hand, of course, but also her arm and onto her beautiful little nipples.

"Are you serious? I thought you were joking. Fuck." My embarrassment was intense. And Darby wasn't exactly being understanding. I tried to make the best of it. Sort of turn it around with a joke.

"You know, I hear it takes lots of practice to learn these things." I was kind of grinning when I said it. Darby wasn't laughing.

"Look, I didn't ask for this, you know. My mom wants me to make a list of shit I need to buy from Target for my dorm room. That is what I should be doing. But I am not. I am hear, teaching my friend how to not blow his load too fast when he fucks his sister's mom. So, give me a break. This isn't for me. Now how long before we can go again?" Whew. You do not want to cum too early for Darby. She gets angry.

"I don't exactly know. It doesn't come with a manual. Usually doesn't take too long."

"Fine. While we are waiting, I need your help." She grabbed her backpack and pulled out a bunch of clothes. Jeans, shorts, t-shirts, a swimming suit. Actually, three different swimming suits.

"I brought every tight piece of clothing I own." I was kind of surprised. I didn't think she had anything like this. Honestly, I had never seen her in anything that showed off her body.

"At first I was thinking this?" She held up some cut off jean shorts, like from that old TV show. But I suppose she decided against that as she threw them on the floor. Next, she held up a little black dress. I bet she would have looked great in that, but before she could even try it on she reached for the swimming suits.

"Do you think Chelsea will lay out by the pool tomorrow?" My phone started buzzing. I ignored it.

"Probably. Most afternoons she does for a while."

"Maybe these are what we need." She started putting on a swimming suit. It was a one piece. Blue. It was nice. Her body looked amazing. The second was a two-piece. It had these lacy, frilly things on it. Again, not bad. I don't think Darb could look bad in a swimming suit. Then she tried on the last one. I call this last one a swimming suit because in the strictest sense, it was. But to put it more accurately, it is about a third of a swimming suit. It was the skimpiest thread of a bikini I had ever seen. Fiery red. It might cover her nipples on top, and just barely her bush down below. Good thing she is trimmed nicely there. Anyway, she put it on, and I have never seen a swimming suit so sexy. You know how some people say you have to leave something to the imagination. Well they would not say that if they had ever seen Darby in this bikini. Nothing to the imagination, and that is okay by me. Come to think of it, why did she even have this? I can't imagine her ever wearing it out in public? I made a mental not to ask her about that later. I realized there was no time to now.

"That is the one."

"Really?"

"Yep, that is the one. No question. Darby?"

"Yes?"

"I am ready to try again."

"Oh. Wow. That was fast. Good. Okay. Let's do this." I resumed my previous position on the bed. So did Darb. Then she grabbed me, down there, kind of rough. She looked me right in the eyes. She meant business. My phone started buzzing again. I thought about answering it, but the look in Darby's eyes told me that would be a mistake.

"The goal here is to last as long as you can. You have to try."

"Got it. We should be better because I just um... did... a few minutes ago."

"Well, that is helpful then. When we do this for real, make sure you rub one out right before things get going." I don't think I have ever been told to masturbate in my life. To be honest, it was the only part of the plan I was sure I could accomplish.

Darby started to gently rub me. It felt great. Her hand was so warm, so soft. Like they were meant for doing this particular thing. In no time at all I was fully erect and enjoying the experience.

"I have only done this a couple of times, so I am learning too here. But I am going to try some stuff."

"You have done this a couple of times? With who?" She was getting annoyed with me, but she did answer.

"Jeff Carlins, for one."

"Jeff Carlins! When did that happen!"

"Is this really the time?" Probably not. But strangely, Darby telling me about giving a hand job to another guy had only made my cock harder. Even if it was to a giant douche bag like Jeff Carlins.

I guess Darby was ready for a change of pace, because at that moment she switched the hand that was stroking me with and put her free hand down by my balls. Then she started rubbing the tender spot up underneath my balls. It was an amazing feeling. Do all girls do this? Or is this something only Darby has figured out? Either way, it was a keeper. I instantly started moaning. Then I realized that I was moaning loud enough to be heard outside of my door.

"Crap. I need to be quieter, but it feels so freakin' good." Darby got a devilish look in her eye and told me not to be quiet. It wouldn't be the worst thing in the world if Chelsea heard me.

"What about my parents?"

"They are probably in bed by now. Right?"

"Maybe." I said. Maybe. So I kept making sounds, although not as loud as before. It occurred to me that the touching Darby was doing on that sensitive spot felt like what I imagined she would do if she were touching herself.

"Show me." I said.

"Show you what?"

"She me how you play with your pussy." She thought about it for a second, and then slightly changed the way she was touching me. A little softer. I little more... intentional. The difference was slight, but it turned me on even more. I decided to push a little further.

"Show me what you want to do to Chelsea's clit." Just my question elicited a quick, shallow breath from Darby. She kept doing the same circular movement with her fingers on my spot (that is what I decided to call that place she was touching me, my spot), but now she was a little rougher. I little faster. As if she was excited by this too.

"Darb. I am getting close." She immediately stopped all touching. It was agony.

"This is it then. When you start to feel like this, I want you to act bored with what you are doing and switch positions. That will give you a chance to hold off the inevitable. And if you are really close, switch to a position that is all about her, where you aren't even being touched." Clever. I decided right then and there that I should ask Darby what to do with all of my problems in life. She is a problem solver. This just might work.

"Well this is one of those moments. I am really about to lose it. So, I guess we better switch to a new position and focus on you?" She saw right through me. I thought there was no chance this would work. But she just innocently looked up at me and said, "Okay."

I wasted no time. I got up and let her take my former place. I came around and put my hands on her knees. I looked at her one more time for reassurance.

"You sure?"

"Yes."

"Tell me if I mess up?" She started nervously laughing.

"You won't mess up. You can't mess up. Some things feel better than others. But you can't mess up."

"How do you want me to start?"

"Maybe just with some touching? Careful though. I am kind of sore."

"I can be careful. I can do that." I carefully guided her knees to separate, spreading her legs wide and revealing her vagina. I was in heaven. I reached my right hand to her and barely brushed my knuckles across the labia. She bucked a little.

"That is nice. Where did you learn to do that?"

"I'm making this up. A friend of mine taught me how to improvise." She smiled. Then I placed the palm of my right hand on her inner thigh just beside her vagina, leaving my thumb available to gently graze over her entire pussy, top to bottom and then reverse.