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 I

The last week

I felt a little bad. Sure, it was hard to maintain the guilt while my dick was being slobbered over by an incredible vision. But I still felt a little bad.

The weeks that followed my incredible sexual education by my sisters and their boyfriends were as empty and virginal as the 14 ½ years before it. Nothing happened. I hinted and even outright asked Melissa and Stephanie for another chance with their boyfriends, but they dismissed it and told me to go find my own sexual playthings.

I jacked off a lot, naturally, with actual personal memories to call on for once. But having tasted the delicious fruit of sex, having nothing was really frustrating. At school, I tried to find a guy to continue things with, but I wasn’t that assertive, so trying to find a closeted gay freshman to fool around with wasn’t happening. It was my hand and some lotion and my memories that got me through the days.

But back to the little bad. Things changed a week ago. Lukas was in my sister’s room taking advantage of our parents being out at the movies. Knowing this image of perfection was down the hall, but not with me, frustrated me. I found myself in the hallway hoping for a partially opened door and a sneak peek. Stephanie’s room was closed up, but I could hear the two of them talking. Well, yelling. Loudly.

The argument was a little hard to follow. Stephanie was doing most of the yelling. Something about Lukas keeping secrets and not really wanting to be with her.  I moved right up to the door when it suddenly opened and Lukas slammed into me as he was storming out.

“Jesse, are you okay?” He helped me up and I pulled a little move from watching the World Cup: I faked an injury

“Ow! Yeah…just…help me to my room.”

Lukas supported me to me bedroom and helped me sit down on my bed.

“Where does it hurt?”

“My leg. How bad is it?”

Okay, I know this was pathetic. But if you saw Lukas, you’d realize you’d do anything to be with him. The perfect twink with his clear skin, earring, dreamy eyes.

Lukas rubbed his hands up my leg. I was so entranced by his touch that I forgot to fake a bruise.

“You seem to be okay.” He flashed that killer smile. To think that those lips had been around my cock once.

“What were you and Steph fighting about?”

“You heard that? Well, it’s not a big deal. Not sure why she thinks it is. It’s just when Steph and I got together she thought I had never done anything before, that I was a total newbie to sex.”

“I thought you were a virgin?” I was even more intrigued now.

“I was. But only with girls. I had been with a guy before. Well, guys actually.”

“But you acted like what happened that night in the house was weird and new.”

“I was pretending. To be honest, I was totally turned on. Shawn is a major jock. But that’s not really my type. I like them a little cuter and closer to my age. Like you.”

I swear I was going to shoot right there. But somehow I went on.  I didn’t ask Lukas details of his gay past – although I wanted to – but we talked about him and Stephanie. He said he loved her, but every since that night with all of us, he was reminded how much he liked guys before. Stephanie was an experiment to see if he was straight. He wasn’t sure.

Making a move was not my thing. I had tried once with Lukas. I knew I’d kill myself if I didn’t try again right now.

“Lukas. Maybe you need more comparison to figure it out.”

And that’s why I felt bad. That night, the two of us fooled around. And the next night. Then every day. Sometimes Lukas would still get with my sister and then come to my room. Sometimes we’d sneak around Stephanie. We also had to sneak around Melissa. And Shawn who was over a lot. And, of course, my parents. Lots of sneaking.

But my parents never imagined I was doing anything wrong, so I went to Lukas’ house a few times too when his parents were out. It was a week of pure blissful sex…with my sister’s boyfriend. She’d be mad if she knew. I felt a little bad. I decided she shouldn’t know. But I didn’t like that part.


Lukas had just finished fucking me. He was so slow and calm about it, it drove me nuts. I wish he’d be a little more aggressive like Shawn when he fucked. But he liked taking his own time.

I knew Stephanie was home, but she was in her room with the door closed. We’d have to sneak out. Melissa was also home, I think with Shawn. It was a weird vibe in the house with all three of us having closed doors and our parents out for the night.

With some of Lukas’ cum still in my ass, he dressed into his street clothes, while I put on just a pair of boxers. I stuck my head out of the door and determined the coast was clear. We walked down the hall together past Steph’s room and around the corner right past Melissa’s when her door opened.

“Tayler? Shea?!” I blurted out.

Two of my friends, fraternal twins Tayler and Shea, were exiting Melissa’s room. One could immediately see they were a little out of breath with their clothes disheveled. In other words, they looked like Lukas – someone who just finished having sex. My brain couldn’t connect the dots and all four of us just stood there.

“You guys need to go before Jesse…” Melissa, dressed in just a sexy bra and panties, swallowed her next words when she saw me standing in front of my friends. Now there were 5 of us frozen.

“It’s okay, the coast is clear. She’s in her room.” Shawn must have come lumbering out of Stephanie’s room without actually checking the hall. Melissa’s room was around a corner and he and Steph walked right into the mix. Stephanie was wearing one of Shawn’s football t-shirts and seemingly nothing else. Shawn was as disheveled as the other guys. Now there were 7.

“I think we all need to talk.” Melissa, always in charge, declared. Our silence was assent.

Melissa and I both threw on clothes and my two sisters and I sat in the kitchen while the 4 other boys hung out in the living room. Melissa made it clear that no one was to leave.

She turned to the two of us. “Let’s just be honest. It’ll hurt, but it seems we all have some things to admit.” Melissa was in charge.

Stephanie, so much more sensitive than our older sister, nodded and went first. “I’ve been having sex with Shawn ever since that night. Lukas wasn’t doing much and after having Shawn that night, I wanted him again. I wanted his big dick. And I really liked taking it in the ass.”

I looked over at Melissa who was steely-eyed and betrayed no emotion at all. She’d make a dynamite poker player. I decided I needed to speak next.

“For the last week Lukas and I have been fooling around. Every day. I am pretty sure he’s really gay. I know he is still your boyfriend, Steph. I’m sorry that…”

Melissa cut me off. “No. We are not apologizing or making excuses now. Just laying out the facts. Is there anything else?”

I shook my head.

Melissa breathed deep. She looked at me directly, which made me very uncomfortable.

“Since that night, Jesse, I have been having a thing for virginal boys. So, I’ve been taking the virginity of your friends.”

My head got light and confused. “How many?” I choked out.

Melissa thought for a second. “Including tonight, 11. It’s been a one-time thing with each of them so far.”

We sat in silence again. We had each been betrayed by a sibling. The depth of the betrayal was in the eye of the beholder. Melissa had a reputation of making boys who cheat on her suffer greatly. We had no history of how to deal with internal conflicts. For a sibling trio, we had always gotten along remarkably well.

“I suppose it was inevitable that our experiences that night would have negative results,” Stephanie lamented.

“I don’t think they were all negative.” I wanted to be clear that I regretted the lying and sneaking, but nothing else.

“Maybe we need to do something like that night. A punishment, a consequence. Each of us gets to name something the other must do as a result of our hurting each other.”

It seemed to me like pouring gasoline on a raging bonfire. But fueled by the possibilities, we said yes. Each of us thought for a minute and then called in the 4 boys.

Shawn looked bored, Lukas looked awkward, and Shea and Tayler looked terrified. Melissa explained the consequences. Everyone had to accept what was asked of them and that would make the slate clean.

“Shawn and Lukas, come back tomorrow. Our parents have theater tickets. Twins, you come back on Friday. And remember your need for silence doesn’t change even though Jesse now knows.”

The twins gave sidelong glances to me, but nodded and quickly left. Within 5 minutes, everyone was gone and the three of us were in our own bedrooms. Checking my email, I had notes from a couple friends. I couldn’t even look at them without feeling nauseous. I was asleep by 10 p.m.