Summer of My Discontent Pt. 02

This is the second part of the Summer Of My Discontent series. I recommend reading Part 1 first. It is located in the Lesbian category. Enjoy!

***

God, I hate myself. Here I was, doing it again. Curtains in my room- closed. Door locked. Lights off in the middle of the day, rock hard cock in my hand thinking about her. At least this time, I wasn't going to look at it. No way. I had to stop. It was becoming an obsession. Every time I closed my eyes for the past three days, she was all I could see. Those tits, that sweet pussy, that ass. It was bad enough that I had not touched any of these things for myself, but now I was thinking about them constantly. How would her nipples feel as they hardened from my tongue caressing them? What does her pink pussy taste like? Would she let me ease my cock into her tight little ass? Would she make a sound, or just turn around and give me that incredulous look, as if to say, "I can't believe you just put your filthy cock in my tight, clean little ass?"

Imagining that look was getting me there. I was close. And then, completely against my will, my left hand reached over and opened up my phone. I found myself looking at a close-up photo of my ex-girlfriend, eyes closed, licking my sister's shaved, pink pussy. Not just licking it. Savoring it, like it was the most delicious thing she had ever tasted. As if she wanted this moment to last forever. I had never seen that combination of lust, pleasure and contentment on her face when we made out. But she had it when she was licking my sister's perfect little clit. I erupted. Cum everywhere. I closed my eyes and imagined my cum spraying all over her ass. I had done this same thing countless times over the past three days. But what really bothered me was that in my mind it was not Rigby, my ex-girlfriend's perfect ass. No. It was my sister's. God, I hate myself.

Three days. It had been three days since Chelsea humiliated me by fucking my girlfriend. Ex-girlfriend. Soon to be ex-girlfriend. I hadn't actually broken up with her yet. To be completely honest, I hadn't even talked to her. For three days she had been trying to get ahold of me. She had been blowing me up. And for three days, I had sent her to voicemail. I had not even listened to the messages. Was she going to tell me what happened? Pretend that nothing happened? I didn't even know if she knew that I knew. But maybe the worst part of the past three days wasn't that she cheated on me. Or even that she cheated on me with my sister. Everyone is powerless against her wickedness. The worst part was the photo that my sister sent me at the moment of her ecstasy. Why do I still have it? Why do I keep looking at it? Why can't I stop?

Determined, I grabbed the phone and opened it up again. There it was. All I had to do was hit the delete button and rid myself of it forever. Seeing it again, moments after I had just cum, my penis started getting aroused again. Jesus. What is wrong with me? Why does the sight of my sister's engorged clit make me want to cover my room in cum? I clicked the phone off. But the picture was still safely there, undeleted, if I should need it again in five or six minutes. I got up, unlocked my door, hopped in the shower, and flopped back onto my bet. I should get up. I should do something. But why ruin my streak? Three days of hiding in my room. It was an impressive display of defeat.

My phone started buzzing. Rigby. Ignore. Just then I heard some talking in the hallway outside of my room. It was my sister, for sure. And my buddy, Darby?

"Hey, I'll see you there in August, right?" Yep. Definitely Darby. She was going to the same school my sister attends. Actually, Darb is my smartest friend by far. I think she got into every single school she applied for. Some really competitive ones too. In the end, she picked a state school not too far away from town because they made her an offer she couldn't refuse. (We watched The Godfather in my film class last year. Darby was in it too. Great movie. Had to get all the parents to sign off on the class watching it, even though I think the entire class was seniors. School. It is beyond absurd. Anyway, now we can't stop quoting the movie.) They gave her a full ride! Complete academic scholarship. So, she is following the money. I don't blame her.

"You are going to State? I thought were some genius?" My sister. Take a moment to appreciate her eloquence.

"Yeah, well I got a good deal. Maybe when I get there you could show me around?" Oh god. Darby, no. I have thought for some time that Darby was in lust with Chelsea. The weird thing is, I honestly didn't know Darby was into girls. Maybe she isn't- but she sure watches Chelse when she is near.

"I don't know. I guess, if have time. I'm gonna be real busy." Complete blow-off.

"Oh. Yeah. Sure." Darby gets it. But her voice sounded a little disappointed to me.

"You hear to see dumbass?" Again. A poet.

"Yeah." There was a slight pause. "He isn't, you know. Dumb. He is one of the smartest guys I know." It probably isn't true. Darby has a lot of friends. And she was like... third in our class. But I didn't care that she had to lie to defend me. I just thought it was damn decent of her to even try.

Chelsea said, "Yep. The little guy is a real winner. Do yourself a favor and don't ever make a bet with him." Then she sort of chuckled, and was gone. Half a moment later I heard a knock on my door. But I didn't really want to see anyone. So, I pretended I was asleep.

"What?" I said it like I was kind of groggy.

"Quit acting. You are terrible at it." She would know too. She is going to major in Japanese, with a minor in Theatre. She has been in plays all over town. She is good. Whenever I'm around and she tells someone what she is going to study in college, I always say in my best hick dialect "What are you gonna do with those degrees? Kabuki?"

To which she replies, "Noh." Ahhh! You get it? It's funny cause... You see, it's a... you know what? Never mind. We think we are hysterical.

"What do you want?" Still groggy. I wasn't ready to give up just yet.

"You are not asleep. I am coming in, so if you are naked, or worse, cover up." Darby gets me. What could be worse than naked? Actually, given my activities for the past three days, she was right. It could be a lot worse.

"Just talked to your sister for a second out here. Why does she always call you little? You are much taller than her."

"I think it is a swipe at my manhood."

"Oh. How would she know. Has she seen it?" I had never really considered it before.

"I guess she just assumes."Having given me enough time to make myself presentable, Darby opened the door and was surprised to see a fairly dark room at close to 3 pm.

"It smells weird in here. Like B.O. and Cheese Whiz had a kid." That is what I like about Darby. She is honest, but she is also sort of witty. I was really into her about two years ago. I tried to take it to the next level, but she "friend zoned" me pretty hard. I got over it. But Darby is cute. Short, black hair. Pretty small, just a little over five feet. I don't know what she weighs. I could ask her. She would tell me. I mean, she would make me tell her what I weigh first, but she would. She always looks great. Actually, I am not sure about her tits either. She usually doesn't wear form fitting clothes. She is kind of a sweatshirt and leggings girl. But I know she takes dance (for being in musicals and such) and when she was younger she took gymnastics, so she is probably still flexible. What am I trying to imply here? Mostly that I am a jerk. But Darby always looks great.

"Sorry, I haven't gone out much." I said. Darb came over and sat down on the edge of my bed.

"Yeah, I know. Nobody has heard from you since last week. What's up?"

"Let's just say, it hasn't been my finest week and leave it at that."

Just then my mom threw open my door. "Don't forget to..."

"Mom!" I cut her off.

"Oh, right. Sorry. Hi Darby!" She shut the door then knocked. My family is terrible about knocking. I am always jealous when I am at someone else's house and their parents always politely knock before they enter the room. Not mine.

I waited just a little bit before answering her. "Come in."

"Don't forget to mow the lawn. It looks pretty bad, and Chelsea's mom is coming Friday." I had completely forgotten that Chelsea's mom was gonna be in town. No wonder Chelsea was being particularly horrible the past few days. She always gets bent out of shape with anything to do with her mom. They don't see each other very much. Once every couple of years. Actually, the last time she came in town, I was out of town at a comic convention. (I can feel your judgement. But the people are fun loving and passionate. What more do you want?) So, it had maybe been five or six years since I had seen Mrs. Jankowski. That was her new name. She got remarried a few years ago. I remember Chelsea was not happy about that. Hates her new step dad. But she never really sees them, so who cares, right?

"I'll get to it." I said.

"I'm not kidding, I need that done. We can't look like the family that never cuts the grass and parks cars on the front lawn. You know how important it is to your sister."

"It's next on my list."

"Okay. How's your summer going Ms. Darby?" Why do people over thirty do that? Call you Mr. or Ms. and then use your first name? Is it me, or is that a little unsettling?

"It's going great Mrs. Abbey." Ha! How did Darby know exactly what I was thinking!

"Sassy. You know I have always liked your sass." was my mom's reply. In her defense, I don't even think she realized what she said. Or what it sounded like. But Darb and I did. Darb shot me a look, mouth agape. You know what I mean. I, on the other hand, could only plead, "Mom!"

As she was already closing the door we heard a "Bye you two." drift our way.

"I love your mom."

"Sold. She is yours. Take her when you leave."

"Alright. Enough. You are moping. I hate moping. You are going to tell me what is up with you right now, or I am not going to share my Sour Patch Kids." What can I say? She knows my weaknesses. But this was no idle threat. She was already reaching in her purse to pull out the package. Then she popped one in her mouth. And just sat there.

"You really aren't going to give me one."

"No."

"Please?"

"Nope."

"Pretty please." I tried my best to be seductive. Bedroom eyes. She was on to me.

"Don't even try. You lay there with nothing but a damp towel and your sexy wet hair, making your little eyes. Not going to work on me."

"Hey, you had your chance. You passed."

"I just told your sister you were smart. Don't make me a liar. That was years ago. You were still a boy."

"We are the same age!" I protested.

"And you were still a boy. Now stop stalling. I want to know what is going on." As a measure of good faith, she dropped a Sour Patch Kid on my chest.

"Thanks." I said. "But I can't tell you. I know we usually tell each other things, but not this time. It is too much. I wouldn't know where to start. And I feel bad enough now. If anyone knew, my shame and insecurity would merge into a singularity."

"Fuck me. Now I have to know. What is going on? Does it have to do with Rig? She told Emmy you had disappeared." I sat up. I thought about it. My room was still kind of dark, though both our eyes had adjusted. If there was anyone I could tell about this, it was probably Darby.

Before I could say anything she said, "Oh my god. Did it not work?"

"What?"

"...IT?

"What? No. It works. Oh my god. That is what you thought? Ewww. It works. I wish it would stop working." At this point, Darby had had enough. She pounced on me. Threw her body on mine. Kind of like we were going to have sex, with her on top. Only instead of grinding her pussy on me, she grabbed my chest with all her nails and dug them it. It hurt.

"Ouch. What the hell?"

"Tell me now or I strike first blood." That one wasn't from film class. We watched that in my basement a few weeks ago. She won't stop using it.

The thing is, I needed to get her off of me, fast. How can I put this? She was making my dick hard. It was quickly growing right were her pussy was inadvertently pressing against me through her leggings and my towel. I had about three seconds or she was going to know that I was aroused.

"Darby."

"Yes?"

"I'll tell you. I swear."

"Oh. Okay." And then she removed her claws from my chest and got off of me just in time. By the time she was back on the bed, I had a full-blown erection. She never knew. Meanwhile, I sat there, not knowing how to begin. I settled on direct.

"Chelsea fucked Rigby." There was a significant pause.

"That bitch." I didn't know if she was referring to Rigby for cheating on me, or Chelsea for deflowering my girlfriend. Or, now that I think about it, Rigby for getting to fuck Chelsea. Honestly, any of these might be correct.

"Are you sure? How do you know?"

"It happened."

"How do you know? Maybe it is just..."

"I watched."

"Holy fuck. Holy fuck. You watched your sister fuck your girlfriend.? Holy fuck. Holy fuck." She just kept saying it. But it isn't like it was an inappropriate response. More like it was the only appropriate response to the world's most inappropriate thing.

"Start over. Tell me everything. Don't gloss over anything. Even the smallest detail might be important."

"How would you even know what an important detail was or not?"

"Because I am a girl you dumbass! And from the looks of this room, I am the only help you have." I try to make it a point not to argue with Darby, especially when she is right, which is usually. So, I told her. I told her everything. The car keys. My misplaced confidence. The bet. My stupidity. The closet. Everything.

"Wait. Say that again."

"She took her dress off while she was facing me. I saw everything." A slight pause.

"What did she look like?" Did her voice just crack a little? By now Darby was laying down next to me in the dark. I started to tell her about my sister's body. What her tits looked like. At one point I thought I saw Darb lick her lips out of the corner of my eye. Maybe not. It was dark. It occurred to me that her intense interest in this part of the story might not be strictly to help me. In fact, by the time I got to describing Chelsea's bright pink pussy lips Darby reached down and acted like she was adjusting her leggings. But she wasn't. She just used that as an opportunity to ever so slightly rub her clit. It was most likely throbbing by now. I felt bad for her, mostly because I was in the very same position in the dark closet last Saturday night. Needing relief, but not being able to receive it. I was certain that that if I somehow vanished from the room, Darby's hand would be down her pants in a millisecond.

When I got to the part of the story where I started to rub my own cock, she looked up at me. Our eyes were six inches apart, and I could tell she understood. I finished the story. I told her everything. The looks from Chelsea. The text. The photo. Cumming harder than I ever have in my life. My shame. Everything. By the time I finished, Darby was sweating. The poor girl. I felt bad for her for two reasons. First, listening to a story about your pathetic friend being demolished by his sister can't be fun. The second reason was that I could see she was as turned on as she had ever been in her entire life by this story.

"Holy fuck."

"Yeah."

"What have you said to your sister? What are you gonna say to Rigs? What have you been doing for the past three days?"

"Not much. I haven't really even seen Chelse. Rigby has been blowing up my phone, but I haven't gotten back. Mostly I have just hidden in my room and masturbated. Sorry. But it is true. And that is the worst part of it. I can't stop thinking about the images. Most of the time, when I touch myself, I am thinking about... her."

"Her?"

"Chelsea."

"Holy fuck."

"I want to stop. I do. But I can't make myself stop looking at that fucking pic on my phone. It makes me cum so fucking hard."

"Wait! What? You still have the pic? You didn't delete it?"

In my shame. "I still have it." A switch went off in Darby. She stood up and walked over to the door. I thought she might run out of the room and confront Chelsea or something. Instead, she locked the door. Then she turned around and walked over to me, slowly like a cat stalking something. When she got to the bed, she sat back down facing me. Then she spoke in the most calm, deliberate manner I have ever heard her use.

"You are my friend and I love you. I do. I am going to help you through this. We will figure it out together. But right now, I need something from you. And you have to give me what I want, even if you don't really want to. I have never really asked you for much, so I am all in here. I need this. And you are going to give it to me."

"What do you want?"

"I need you to let me see that photo." Her eyes were begging. Pleading. If I had said no, I think whatever it is that makes Darby who she is might cease to exist. Still, sharing it seemed somehow embarrassing. Painful. I didn't know what to do.

Just then, Darby reached over and took my hand. Very slowly, she guided it down to her pants and pressed it right on her pussy. It wasn't a sexual move. She didn't want me to rub her. I could tell that. It was informational. She needed me to know something. It only took me a second to understand completely. Her pants were soaking wet. I don't mean a little damp. I mean wet. As wet as if I had poured a glass of water on her.

"I need to see that photo." I reached for my phone. Darby took a breath. It may have been the first breath she taken since I said I still had the damn thing. I opened my phone, found the photo and handed it to Darby.

"Should I just leave?"

"Why?"

"So... you can do what you have to do?"

"We are in this together. Stay. I am going to... touch myself now. It won't take long. If you like what you see, you can do whatever you need to do. No one will ever hear about this from me. It is totally our thing."

Then, without waiting for a reply from me she slipped a hand down her leggings and starting slowly rubbing her own pussy. Her eyes were closed. She looked like she was concentrating. But she wasn't looking at the photo of Rigby and Chelsea yet. She had the phone in her other hand, but it is was face down, like she was saving it for later.

After a moment or two, I could hear her rubbing her pussy. I must have been so wet because it was making tiny sounds. I was just lying there, not really knowing what to do when Darby suddenly stopped.

"This isn't right." She said.

"God. I'm sorry. Why don't I just leave." But I don't think she heard me. She got out of my bed and took her sweatshirt off. For the first time ever, I got to see my friend's tits. They were awesome. Holy shit, they were perfect. Again, no bra. Is that a thing? I thought all girls wore bras. She looked at me, staring right at her fantastic breasts.

"I usually wear a bra. They were all dirty. Besides, I thought I was just gonna hang with you for a few minutes." As usual she could read my mind. Or is it that I am just not nearly as complicated as I think I am? Someday, when I am trying to unravel the events of this summer with a therapist, I will have to ask them about that.

Then she stuck her thumbs into the elastic of her leggings. Oh wow. She wasn't kidding. She really was all in. With one last look right at me (did I detect of hint of doubt?) she arched her back forward and slid her leggings to her ankles. She stood up slowly, probably trying to decide if she had made the biggest mistake of her life.

Yeah, it was dark. But I had fully adapted. And I don't think there is enough darkness in the world to hide what I was seeing. My eyes were fully dilated. I was taking in everything. Darby was a ten. Who the hell knew? I knew she was cute. I knew she was brilliant and funny and for some reason put up with my mediocrity. But she was amazing. Her short haircut was perfect on her when you could see the entire picture. It was as if she picked the haircut specifically for when someone would see her completely naked. Black hair. Shapely, large breasts. Not as big at Chelsea, but still large. And perfectly proportioned. They were exactly the same size. I thought one was usually bigger than the other. Not on Darby. Perfectly proportioned. As my eyes trailed down her firm torso, I saw her pussy. She had dark hair, no surprise there. But it was trimmed. Kind of in a triangle. Not harsh. Just trimmed up. Like she didn't want anything escaping a bikini. Oh, my penis. Hadn't I had enough punishment lately?