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.

Comments, suggestions, and helpful feedback are welcome – e-mail me at

Check out all of DerekGuy’s other stories on Nifty at:




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 III

Friday Night

Shea looked nervous. He was the younger twin by 2 minutes. He had short brown hair, skin that looked like he just came back from the beach and adorable dark eyes. Tayler would be described the same way, but he only sort of looked like Shea. You could tell they were brothers, but other than their age, it wasn’t obvious they were twins.

I was closer friends with Shea. While both played video games online with me, Shea had always felt more like a kindred spirit. We had both been into Pokemon at the same time and both had been into X-Men at the same time years ago. In school now, I sat next to Shea in Biology and we were in gym together. Tayler sat behind me in Math and a few seats away in History. They weren’t my closest friends, but I liked them both a lot, especially Shea.

Melissa wasn’t around, so it was just the twins, Stephanie, and me. She looked hot. She was wearing a really tight black dress that was too short on the top and the bottom. If Mom ever saw here wearing that, she’d kill her. But Mom and Dad were helping Aunt Susan with something for the night. Since Mom believed us that nothing happened last time, she promised not to call more than once or twice. The rule of no guests in the house still applied. We ignored her as usual.

“Here’s the deal, boys. Jesse, even if Lukas and I weren’t meant to be, that doesn’t mean you can have sex with my boyfriend.”

At this, Tayler giggled. I guess he was one of the kids who didn’t realize I was gay.

“So your punishment will not be too bad, but you’ll have to earn back trust with your actions.”

I still had no idea what she meant, but I knew she’d take care of me in the end. Little did I know.

“As for you boys, sneaking around and having sex with your friend’s sister is no way to live life. Therefore, you boys will help me with the consequence, but I don’t think it’ll be too bad for you.”

“Yeah, but other guys did it too. I mean Chuck, Ian, Devin…” Tayler had always been a bit of whiner.

“Shut up, Tay!” Shea hissed.

Stephanie was not interested. “But you got caught. They didn’t. That’s one of the most important lessons in life. Don’t be the one who gets caught.” She let the words settle. Shea was more ready to go, expecting it might mean he’d get a chance to touch Steph’s boobs. Tayler was generally apprehensive about many things.

Stephanie concluded. “Jesse you are going to be a sandwich for the twins.”

“No way.”

Shockingly, it was my voice that said that. I had already been the meat in a 3-guys sandwich and it was awesome. I would happily further my friends’ sexual education. But something about the moment told me that the best path was to play a little difficult. Tayler wasn’t going to into this lightly.

“We’ll do it if Stephanie fucks us.” Shea was so bold, unusually confident and direct.

Stephanie shook her head. “Suck us?” Shea tried negotiating.

“You’ll fuck and be sucked by Jesse.”

“But we’re not gay,” Tayler feebly offered.

“What decade are you living in?” Stephanie dismissed him. “I don’t care if you are gay, I’m asking you to get your rocks off. Close your eyes if you have to. Did you do a sandwich with Melissa?”

The boys both nodded. I would have loved to see that.

“Then get to work. One at each end.”

“But where do we stick our…” Shea wondered half-outloud.

Even Tayler looked at him as if he was a dumbshit. “Oh,” was all Shea could muster.

Stephanie, to help things along, undressed both twins. She rubbed herself against them a little and let her hand brush their cocks briefly. Like most 14-year-olds, that was enough. “But boys,” Steph whispered in the tone I recognized that she reserved for lying, “if I like what I see, you never know…”

Using those twin powers, Tayler and Shea shared their preferences. It seemed Shea wanted me to suck him, while Tayler was interested in exploring anal sex. I preferred this arrangement, as I’d get to be more personal with Shea. The three of us were soon all in the buff.

They had nice little dicks. Smaller than mine, even. Having been with only two boys, both them older and much larger, I smiled. This would be more about pleasure. I dropped my briefly-lived façade of same sex dislike and dove in.

Shea got rock hard quickly. It only took another touch from me as I guided him into my mouth. His dickhead poked out and then got his shaft stretched to its maximum position.

Tayler had some trouble getting things started. Finally, Stephanie walked over from the chair she had planed to watch the action. She reached a hand in to get it going Having had Shawn’s monster us my ass, Tayler’s was like a starter kit. He stumbled in his attempts to push in and out. His cock fell out over and over. But he seemed to like it. I wanted something consistent. He was happy just to be in the game.

Shea kept making eye-contact with me. He was very natural and at ease to have me blow him. Sharing a guy with his brother, on the heels of sharing that guy’s older sister, didn’t seem to be an issue at all. I knew that we could do this again – and more. My future options seemed so much brighter than just a week ago.

As much as I loved being the meat for their sandwich, I wasn’t feeling that intense. My dick was half-hard and I was imagining possibilities with Shea and Ian and other classmates. I wasn’t even thinking about Lukas or other older boys as I usually did. Maybe Melissa ultimately did me a favor with her exposing my friends to sex. The pleasured look on Shea’s face as sucked his cock might make it all worth it.

Behind me, Tayler was still struggling. He was now standing pressed up against me with his dick entirely in my ass. His movements were small, preventing a pull-out that caused his dick to fall out again. He also lacked rhythm or the understanding of it. I thought any boy would have learned that after masturbating, but I didn’t know what went on behind closed doors with him.

Stephanie was sitting in her chair watching us. I could just make her out through my peripheral vision. She had a neutral expression, I think, as she watched three 14-year-olds share their cocks. She looked like a panther waiting to pounce. But on which one of us?

Shea came first. He had pulled out at some point and began furiously rubbing himself. When the moment came, I didn’t let him go, but yanked him back into my mouth and wrapped my lips around the exposed head, swallowing his cum. I did this less to excite my friend and more to prevent him from soaking my hair and face.

Tayler pulled out soon after and jacked himself onto my ass. He grunted loudly as he moistened my lower regions uncomfortably. Nothing I could do about that.

Stephanie stood up suddenly startling all three of us in the moment. She looked at the naked twins and ordered, “Now you both – suck Jesse. Right now.”

Both boys responded to the command quickly. Perhaps they anticipated some sort of reciprocation from her if they did so. I moved to knees, so they dropped to the floor. I flipped onto my sticky back, the cream on my ass making me slide a little. Shea, naturally, was first. He mimicked my actions without much hesitation. After a minute or so, he pulled off and somehow mentally willed his brother to copy him..

Tayler had been blown once in his life – unexpectedly by Melissa earlier that week. He never imagined that would happen. He anticipated he’d be sharing a cock with his brother a few days later even less. To my delight, he went for it. I offered a prayer that twin suckings were a regular part of my future.

The twins shifted back and forth for about three minutes. They weren’t very good at and I felt compelled to stay silent rather than offer advice. But they had me good and hard. An orgasm was an inevitability.

Suddenly Stephanie popped up again. “Stop now. You ever speak of this to anyone and I’ll destroy you. Get out right now. Now!”

Tayler and Shea left in under a minute as they learned you can pull on your clothes and run at the same time. Meanwhile, I had barely noticed Stephanie was on her knees stroking me.

“Lukas and I are totally done. You can have him as much as you want. But first, I want something. Then we are even.”

She leaned in and took my dick. I was pretty keyed up already. I had been close when she stopped the twins, so having an experienced mouth on me jumped my climax forward. Before my brain could fully comprehend what was happening, I felt a wave of energy pulse through my body and began to shoot in Melissa’s mouth. While I had come to feel important and manly shooting off in Shawn or Lukas’ mouth, I felt like a little boy shooting in my sister. When I finished, she gently licked me clean, more like a lioness cleaning a cub, and then she tried to kiss me on the mouth. I turned and she only got me with a semen stained kiss on the cheek.

Stephanie got up, smiled, and slipped out the door.


I knew it was my mom. She was late. Usually, she interrupted at the worst possible moment. I dragged my sweaty, partially clothed, cum-covered ass to get the phone.

Two Weeks Later

Sam and Lionel looked confused. They weren’t sure why Melissa had asked them over to the house on this Saturday night. They knew Melissa was Stephanie’s sister. Stephanie was that hot girl who was dating the metrosexual skateboarder and was now with the football captain.

Everyone knew Melissa. She was one of the girls regularly tagged “hottest girl in school.” As a cheerleader and the (now) ex-girlfriend of that same football player, she was known to be easy. There were lots of stories about her. I assumed that only made them both more nervous.

I showed them to Melissa’s door. In recent days, she had welcomed a bunch of tenth grade virgins to her room – solo and in pairs. They were different than my friends, she told me and Steph in one of our evening chats – one year did make for a change. But she was growing tired of playing teacher every night and might just turn her attention back to the football team. First, she had promised herself that she’d be a more diverse individual. Sam was Asian and Lionel was black. Tonight she completed some cultural diversity.

As Melissa’s door closed, I smiled. Two virgins would be losing that status in the next hour. As I walked back to my room, I could once again hear Shawn and Steph being loud, aggressive, and athletic. Every chance they got, their sex was some of the most exhausting I could imagine. But Steph seemed happier than she had with Lukas. And it had freed my almost Abercrombie model to spend time with me.

Lukas and I had continued fooling around here and there. Sports, school, other friends kept it occasional. But when we made the time, it was reciprocal and loving. We often cuddled and talked more than we made out. Without the sneaking around, it lost a little of the excitement. We both said we didn’t want to date. We both were still learning so much. Lukas was also not officially coming out at school and had started officially seeing a hot cheerleader.

I had been nervous about going back to school. I avoided everyone all weekend after Shea, Tayler, and my threesome. On Monday, a couple of the guys I knew or assumed had been with Melissa avoided eye-contact with me. Later in the day, I approached each of them and simply acted like old times. No, not exactly. I was more outgoing and assertive than usual. I was more comfortable just being me. We set up plans to play Rock Band or hang out. When my friend Chuck showed some apprehension at coming to my house, I told him Melissa would be at cheerleading practice and that was all water under the bridge.

My social calendar was fuller than ever. I especially started hanging with Ian, often at his house. His eye-candy older brother Joel usually wasn’t home though.

Having dropped off Melissa’s final 10th grade toys and confirmed Steph was well taken care of, I returned to my room this particular Saturday evening. I had an evening planned myself. I returned to my room and got back to business.


My cell phone was in reach and I glanced at the screen. “Hey Lukas!. Yeah, we’re still on for Monday afternoon….Right now?, I can’t now. Hanging with a friend.”

I hung up and looked down at an annoyed Ian who was doing his best to service my cock. He didn’t like that my attention was diverted. I smiled at my good friend, who had become a much better that first afternoon at his house.

As he continued pleasuring my dick, I smiled. For once, I got to turn down a night with sister’s ex-boyfriend for a night of my own.