My Sisters’ Boyfriends 2

By DerekGuy17

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.

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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 Friends:

Shea – 14, Freshman (Tayler’s twin brother)

Tayler – 14, Freshman (Shea’s twin brother)


Part II

The Next Night

Melissa reiterated that everyone had to comply. Lukas nodded. Shawn yawned. The hot football player had no trouble finding pussy. But Melissa was the most sexual thing around. And her sister was very hot. Both of them liked it backdoor, too, which he especially appreciated.

“Here goes,” Melissa began. “Shawn, you cheated on me. You know how I despise men who cheat on me. You need to have a consequence.”

Shawn was clearly not concerned with his punishment. What could she ask him that he had never done?

“Further, I wronged Jesse. I never should have touched your friends. That was a selfish thing to do. I have betrayed you and I don’t know how to make it all go away. But at least, I can do something nice for you to show that I now realize I was wrong and how sorry I am.”

I willed myself not to cry, but I was losing out. ‘Lissa needed to name her consequence now.

“So, I want Jesse to fuck Shawn.”

I was blown away. The adventuresome night, I had longed to do that, but it never happened. Shawn was reluctant to do anything gay, although they had done quite a bit.

“No fucking way,” Shawn stated. “No guy is fucking me.”

Melissa stared him down. “Do you remember what I did to the last guy who cheated on me?” I had trouble remembering which situation that was. It might have been the one where she fucked the boy’s father and ruined his family. Oh wait, that was when she took revenge on Steph’s ex-boyfriend. Was it Ned Jenkins? She had fucked Ned’s brother Connor. Connor was my friend and I guess that was her first de-virginizing of my friends.

Given the deadly serious expression on Shawn’s face, it seemed to be something else. He whispered, “Okay.” There was no more discussion.

“What about me?” Stephanie sounded pained and desperate. “What’s my punishment?”

“Nothing,” Melissa shrugged. “I cheated on my boyfriend. You cheated on yours. That you cheated with my boyfriend is his issue, not yours. I love you and forgive you and forget it.”

“Well, I still feel bad and that’s my punishment.” She turned to her about-to-be ex-boyfriend. “ Lukas, you are amazing, but it’s clear we’re not meant for each other. I want you to do something for me and then we can end things. Maybe it’s the last time you’ll be with a girl.”

Lukas rolled his eyes and was looking for a way to protest, but then didn’t.

Stephanie continued, “Lukas, I want to you to do a major orgasmic eat out session on Melissa. At least this way I can do something nice for her too.” Lukas, despite his gay leanings, had a great tongue for pussy, Stephanie had told them previously. Lukas said nothing.

“What about me?” I asked, hoping Steph would forgive me the way Melissa forgave her.

“Your consequence will be dealt with on Friday,” she said with certainty and would say no more. I had nothing more to say. Melissa’s consequence was much better than the idea I had to get back at her. I was fine. At least until Friday.

A short while later, the group broke up. Melissa and Lukas headed to her room. Unlike our last adventure, this was not a public performance. When their now ex-lovers departed, Shawn and Stephanie looked at each other and slipped off to her room.

Standing alone like a dumbass, I shuffled back to m bedroom. I sat down at my computer and made a list of all my friends I thought might have been involved with Melissa. I wrote a somewhat bitter, somewhat vague email.

“Dear friends. It has become clear to me that some of you have been driven by your lust and have betrayed me. I am very saddened by this and know that efforts must be made to repair the situation. – Jesse.”

I was just about to hit send when I saw my friend Ian had come on. We started to chat and I shared what I had learned honestly. Surely, Melissa would have chosen him – he was good looking and had a great smile. But he wrote nothing back. I wrote a version of my as-yet-unsent email to him. There was a pause. I could see he was typing, but it stayed that way for at least two minutes. Then a message appeared.

“And you wouldn’t have done it with my brother?”

Ian’s older brother Joel was a beautiful junior. I thought about it and realized Ian was right. I would have sex with Joel if he approached me even though he was my friend’s brother. I was upset because they had an opportunity I didn’t have.

I started to type and then realized something else. Ian wrote as a casual fact that I was gay. He didn’t qualify it or anything. Melissa and Steph told me that everyone knew I was gay. I didn’t know that applied to people my age. Finally, I wrote.

“I guess your right. Would you ask Joel if he wants to fool around?”

All the tension was broken between us. I decided I wouldn’t send the email, but would talk one-on-one with my friends. If I was to stay friends, we had to get it out in the open – both the situation with Melissa and my being gay.

I went to get something to drink and passed Steph’s room. I could hear the two of them moaning inside. It seemed despite the revelations and Melissa’s potential anger, the two were unable to stop their time together. I pushed on her door, but it was truly closed. So I opened it quietly. I had been sneaking peeks on my sisters for a couple years and knew just how to manipulate the doors to not squeak.

I opened it wide enough to see the beautiful naked forms of Stephanie and Shawn. He was on the bed with his giant dick planted inside my sister’s tight ass as she raised it from the floor. They were covered in sweat and pounding hard. I quickly closed the door.

Coming back up from the kitchen, I heard Melissa moan as I passed her room at the top of the stairs. I had heard her moan many a time, but this was something new. It was loud and repetitive. She kept saying words over and over, “Yes! Yes! Yes!” “More! Mooooooore! More! More!” and so on. Again, I gently opened the door to see Melissa, still mostly dressed, with her legs spread wide, lying on the floor. Lukas, fully clothed, was between her legs and moving around quite a bit. I didn’t want to look closely as the vagina is gross. Just thinking about licking one made me queasy. Melissa began to pound the floor with hand while returning to “Yes!” as her repeat word. I closed the door.

While I waited, I spoke to two others friends online. One had heard something from Ian. The other had heard something from the twins. We all worked past it quickly. I was in no position to judge or berate. My second friend wanted to know what was happening to Shea and Tayler on Friday. I told him it wasn’t anyone’s business and he could ask the twins on Saturday if they were telling.

I played some COD and blew things up waiting for the others to be done.

Later The Next Night

Melissa knocked on my door. It was already late, but we knew our folks weren’t getting in until midnight. “It’s time,” she said in a hushed tone. She looked like she had been jogging – flushed, but with an afterglow.

Shawn walked into the room being pushed a little by Steph. Lukas was behind them. I had fucked Lukas a bunch of times now – the only boy I had fucked. I had been fucked by Lukas and Shawn. I wasn’t experienced, but I figured I knew what to do.

Slowly Shawn removed his clothing, His muscles looked huge especially when I stood near him. He was about 9” taller and more than a hundred pounds heavier than me. Melissa handed me some lube and I began to apply it to his hard, hairy ass. I saw his dick was totally soft. He really was straight.

My getting hard took a millisecond and soon I was pushing in. Although I was so small compared to Shawn, his body was automatically expelling anything trying to enter his butt. It had been 1-way his whole life and didn’t change directions easily.

Melissa stroked his face and relaxed him. Stephanie looked uncomfortable but never stopped watching. Lukas had his hand in his pants and was lightly stroking himself. “This is hot,” he stated to no one on particular.

While it been briefly discussed that Shawn might lower himself on top of me, I refused. He’d crush me. Doggie style was the consensus. After a few minutes, and some additional lube, Shawn started to relax. As I didn’t have so much to insert, it wasn’t painful to him. I doubt he got any real pleasure either. He was a hole I was fucking. But I was going to fuck this senior football star.

How I wish someone had taken a picture so I could show future generations that it really happened. I offered my most energetic and active fuck. Lukas would never have accepted such an energetic pounding. Shawn could have been texting someone for all I knew while this was happening.

I lost track of time, but it was probably only 5 or 10 minutes at the most. I debated where I wanted to shoot my load. While spraying his back would be appropriate considering he had done the same to me, I figured if I could get off in his ass, I would.

I could. It just happened. I was fucking him with all my strength one second and then shooting my cum up his crack the next. Who knew how many people he had deposited his seed inside? I wondered if he was a secret top. Never touching others’ cocks, but happily letting guys suck him or fucking them. As I came, I grunted for effect and then collapsed on top of the barely sweaty boy in front of me. It felt good to grab his big, muscular body. My dad wasn’t very touchy-feely and with no brother, I had little chance to roughhouse or engage in brotherly touch. I knew having my dick in someone’s ass wasn’t the typical form of affection, but Shawn let me rest my tired body on his solid one for a few minutes before getting up.

He cleaned up, got dressed, nodded at me with a “see ya’, Sport,” and a kiss to Melissa, he left. Steph looked more nauseous than before. Lukas followed afterward with no particular goodbyes to any of us. This wasn’t like last time at all.

Melissa, Stephanie, and I talked briefly over cookies and tea (I had milk). Stephanie asked Melissa why she liked fucking such young boys. Melissa said it was a power thing. With Shawn, he directed so much of the sexual experience. With my friends, they gratefully did whatever she asked.

Stephanie said it wasn’t so different with Lukas when they started going out. While she thought he was almost a complete newcomer to sex, he still was a virgin with girls and was so hopeless at first. Steph then compared the difference between a freshman and a sophomore. In 9th grade, they hadn’t done anything and were really still little boys. In 10th grade, most of the boys had some limited experience. Certainly they had kissed a girl or maybe more. But few of them had done anything of substance and almost all of them were virgins. Plus, they were more like young men in body.

“Hey!” I shouted. But I knew it was true. Most of my friends were hairless and without much definition, I even knew our dicks were mostly small from sleepovers, showers, and occasional conversations. Lukas’ friends, just a year older, were already taller, had started working out, had grown some hair, and, if Lukas was an example, were doing fine in the dick department.

“I could give you some names if you want to pursue some of Lukas’ friends instead of Jesse’s,” Steph concluded.

They kept talking for a while. I started to doze off, but I did hear Steph tell ‘Lissa that she’d like to start going out with Shawn if that was okay. Finally, ‘Lissa helped me up to bed. Like when I was a little kid, she got me undressed, helped me brush my teeth, and tucked me in. She kissed me on one cheek and then the other, Then she planted a kiss right on my mouth with her tongue exploring my surprised lips.

“Good night, Jess,” she whispered and turned out the light