My Best Friend’s Sister and I Cross a Line

I’ve been friends with Daniel for nearly 15 years. We’re both 26-years-old now and still see each other once or twice a month. We both have jobs and live 45 minutes away from each other, so getting together once a month is an amazing feat. I love Daniel like a brother. His family has always been so lovely to me. I actually stayed at their house for nearly three weeks in high school when my mom suffered severe depression following a nasty divorce. They are good people.

I tell you all this because I feel like a complete douchebag right now. Daniel has a sister named Emily. She’s 20-years-old and still lives at home. She works part time at Sephora and goes to a community college in town. I know it’s customary to add the “stats” of the woman in the story, but who really cares how tall Emily is? I feel like that’d only be relevant if she just so happened to be the tallest (or shortest) woman in the world. What you do need to know about Emily is that she’s magnetic. She has so much energy around her. It’s difficult to explain. It’s like she’s walking through life in her own little musical.

It’s hard for me to describe her sexually, ’cause she’s always been like a sister to me, but uhhhh…things are starting to change.

Daniel and Emily’s parents had a BBQ at their house this past holiday weekend. It’s a tradition. They have a beautiful backyard with palm trees and shit. I was always jealous of their house growing up. I spent most of my life in a dilapidated apartment building, so I didn’t really have a backyard. It’s always a good time going to their house, drinking a little bit, snacking on some food and sharing stories with everyone.

As the sun went down and Daniel’s extended family left, I was prepared to leave too, but they insisted that I stay because they wanted to have a “board game” night. Yeah, they’re THAT kind of family. Basically, Daniel is Cory and I’m Shawn. I won’t bore you with the details of board game night, but it was a surprisingly fun time. I personally think board games are underrated. REAL HOT TAKE, I KNOW!

After Daniel’s parents went to bed, the three of us talked for 30-40 minutes and then Daniel announced he was going to bed. I usually sleep on the couch while staying over, so I went to the hall closet and got out a blanket and pillow to prepare for bed as well. Emily was still hanging around though. She helped me spread the blanket over the couch and we talked some more. Somehow, we ended up talking about the poetry that she writes. This led to her saying, “Actually, you know what, come up to my bedroom and I can show you a few. They’re too embarrassing to say out loud.”

So I followed her upstairs to her bedroom. She plopped herself haphazardly on the bed and then reached under the other side to pull out a stack of index cards. She took off the rubber band holding them together and started going through them.

“Sit down, make yourself comfortable” she said. She was half on her side/half on her stomach, with her ass sticking out toward me. She wore a pair of black pajama pants. The way her ass stood out was fucking with me. I just stared at it the whole time she was going through her poems. At some point, I must have slipped into an ass-induced coma because when I snapped out of it, Emily was nudging me with her leg.

“Are you okay?” she asked me.

“Yeah. Must have spaced out,” I laughed.

“Looked like you were staring at my ass.”

“What?!?” I said, acting completely shocked she’d think such a thing.

“It’s okay if you were.”

“I wasn’t.”

It was at this point she started to jiggle her ass. I tried not to look, but I’m just a human.

“Okay, I was looking. Can you please stop…”


“It’s distracting”

“Show me what it looks like from your view”


“I want to see why it’s so distracting. Take a photo and show me.”

I waited for a minute, thinking she’d be like, “JUST KIDDING” but she didn’t say that. Instead, she pulled my phone out of my pocket and basically placed it inside my hand. Reluctantly, I opened it up to the camera and took a photo.

I then handed her the phone so she could look, “Wow,” she paused. “That is pretty distracting,” she had stopped looking through the index cards a few minutes ago. She was just staring at me now. Her eyes went down to the bulge in my pants.

“Let me see it,” she demanded.


“Emily what? Why can’t we have a little fun?”

“Daniel’s my best friend. We’re basically family.”

“But we’re not, so let me see it,” she started to jiggle her ass again. I could no longer pretend not to be interested. I slowly unzipped my pants and pulled them down (along with my boxer briefs) just enough to reveal my hard cock.

“Holy shit you have a beautiful cock,” she said. It was the first time anyone has ever called my cock beautiful.

I started to pull my pants back up, but she stopped me by grabbing my hand. “Noooo. Cuddle with me.” She reached behind her and slid her pajama pants down to her ankles, revealing her bare ass. She then grabbed my pants and pulled them down before turning back on her side. I positioned myself directly behind her and nearly moaned as my cock pressed against her warm ass. I wrapped my arms around her and pulled her in close.

“We’re not fucking,” I warned her.

“Okay,” she said quietly.

We didn’t move for the first five minutes or so, but then she slowly started to grind her ass against me. My cock slipped between her cheeks. She moved her ass up and down, stroking me between her cheeks. My left hand found her breast through her shirt and squeezed it roughly. Our breathing started to increase at this point. I moved in closer and started to kiss her neck lightly. She continued to stroke my cock between her cheeks. Occasionally, my dick would slid down to the lips of her pussy. She moaned every single time it happened and pushed herself against it, but never let it slip in.

“Suck on my fingers,” I instructed her as I slipped two fingers inside her mouth briefly, just long enough to get them wet. I slid my hand down her stomach to her clit. I rubbed it gently and started to thrust against her ass with my cock. The head of my dick brushing against her asshole.

“Mmm,” Emily moaned as I continued to rub her clit, “I want your cock” she whispered breathlessly.

“We’re not fucking” I told her again. She let out a moan/grunt of frustration and went back to focusing on me rubbing her clit. Her movements against me, which were once methodical, were now sporadic as she moaned in pleasure. My cock once again slid down to her pussy. This time I allowed the head to press against her opening just a little, and before I had time to move it away, she backed herself against me and my cock slid inside her warm pussy.

“Oh, God, yes,” she moaned. There was no turning back. No way I was going to refrain from fucking her now. I kept my fingers on her clit and rubbed it gently as I slowly pushed my cock deeper inside her pussy. After all the teasing, this was pushing us both over the edge. I could feel her start to squirm as she reached out her hand and squeezed her pillow.

“Fuck, fuck,” she cried out as she came all over my dick. I could feel the warmth intensify around my dick. That was all I needed. I quickly pulled my cock out and stroked myself over her ass. Shot after shot of cum covered her ass as she moved it from side to side. She then grabbed my cock and used it as a paintbrush to smear the cum all over her ass.

“I guess we are fucking, huh?” she laughed.