Jane’s Little Sister

Ben (Previously Guy NY)
Quickies in New York
5 min readFeb 8, 2018

“Let’s make a promise,” she said later that afternoon, lying naked against me. I was playing with her hair and she was gently touching my limp cock with a sympathetic look.

“I’m not going to marry you,” I said.

“Fuck you, that’s not what I mean. It’s not that kind of promise. I just think that we have this one chance, do you know what I mean? I’m going back to school in the fall, and you’re going to get a job, grow up, and become super boring, so why don’t we have fun this summer?”

“I was planning on having fun this summer,” I told her.

“Yeah, but let’s do whatever we want.”

“What do you want to do?” I asked dreamily.

“You’re not listening.” She sat up and stared at me. She was deadly serious. “Let’s make a promise that we’ll do whatever we want. I mean, if you want something I’ll do it. And if I want something you’ll do it too. No matter what.”

“So, if I want to spank you until you cry, I can do that?”

“Yeah, if you want to be boring,” she said. “I mean anything, Jack! Like if there’s something you always wanted to try but were afraid of, then we’ll do it. Or we’ll make it happen. It doesn’t have to be just us.”

“You mean anything at all?” It was my turn to sit up and look at her. “Like if I want to fuck Rachel while you watch, then I should do it?”

“You don’t want to fuck Rachel, but yes. I mean, we don’t need to make a list, but if suddenly you want to fuck me on the street then you do it. If you want to piss on the subway track then you do it. If I want to blow the next bouncer who won’t let us in, then I do it too.”

I closed my eyes and tried to think of something to say that would shock her. It was a good idea, but it was a high school idea. It was one of those things you thought up at eighteen to make yourself feel like a rebel. It was like a bad game of truth or dare where all the players can think to do is kiss each other and feel like they’re breaking a rule.

“What if I want to fuck my ex-girlfriend?” I asked.

“Then fuck her. I get to be there though. That’s part of the deal. Everything we do, we do together.”

“So, you want to watch?”

“I don’t know. Maybe I want to hold her down as you do it. Maybe I want to beat her ass with your belt as she rides your cock, and then make her eat my pussy.” Jane was quiet as she said it, but there was a grin on her face that I loved. I pulled her closer to me until she was sitting on my lap facing me. Her legs wrapped around me, and I pressed my chest against hers before kissing her lips.

“I could push her head into your cunt as I fuck her from behind, and you could pull her hair.”

“I could fist her as she sucks your cock, or you could fuck her ass while I slap her face and call her a whore.”

“You are a very dirty girl,” I whispered as I felt myself growing hard again. “What do you want to do?”

“I want to fuck my senior year English teacher,” she whispered. “I want you to bring me to his apartment when his wife is away, and I want you to watch me fuck him until he’s just about to come. I want to stop when he’s almost there and then make him watch you eat my pussy on his bed without touching himself.”

“You’re mean, too,” I said, lifting her enough to drop her back down onto my now hard cock.

“You don’t seem to mind too much.” She circled her hips and kissed me again. “Now, what else do you want?”

I understood the game then, and that’s just what I thought it was. She was going to push until she found something I didn’t like, and I was supposed to do the same. It was foreplay or fantasy, and I could get as creative as anyone, but I had to step it up.

“I want your ass,” I said.

“Lame,” came her response.

“I want to fuck you in a cab while the driver watches,” I tried.

“Better,” she said, fucking me faster. “But still somewhat pathetic.”

“I want to steal your father’s suit and listen to you call me Daddy,” I said, this time digging my hands into her skin as I thrust up into her cunt.

“You’re almost there.”

“What the fuck do you want from me?” I yelled as I bit into her shoulder.

“Something better,” she said. “Something harder. Something true.”

“I want to fuck your little sister,” I blurted out. “I’ve never even met her, but I don’t care. I want to fuck her tight pussy until she cries.”

Jane began to come instantly. She wrapped her arms around me and screamed, and there was no holding back at all. I had only recently realized she had a sister, but that didn’t matter either. In this fantasy, I could do anything. She ground into me, scratching my back so hard that I screamed as well, and she bit my ear before whispering into it.

“I get to watch,” she said as she came around me. “Oh fuck, I get to watch you pound her tight little cunt and call her a whore and slap her face, and oh my God!” She screamed as she came, and I didn’t let go. I pulled her to me and thrust up inside her with all the strength I had left.

“I want to taste her on your cock when you’re done, and then leave her covered in your come on her pretty princess bed. Jesus, I want to taste her pussy on your dick.”

For a moment I thought she might have passed out. She wrapped her arms around me, her head on my shoulder, and her whole body spasmed. He arms and legs shook, and I could feel her heart beating against my chest. I started to come as well, and I couldn’t honestly say if it was her body or her words that did it. I kissed her shoulder as I held her, and my body was a complete wreck. Her breathing was fast and loud, and her nails dug into my back. When she sat up there were tears in her eyes which she brushed away with her hands before pulling her hair back in a knot.

“Are you okay?” I asked. She nodded before kissing me on the nose.

“Don’t get weirded out, but I think I love you.”

“Because that’s what would weird me out? Not that whole thing about…”

“Shhhhh…” she said, with a finger to my mouth. We sat for a long while staring at each other, and I’d like to say I was present. I’d like to say that my mind stayed there with the girl in whom I was slowly growing soft inside. I’d like to say I wasn’t thinking about a baby sister I didn’t know, and what it would feel like to push inside her cunt as I stared into Jane’s beautiful eyes.

(From The Yes Rule, the story of one very fucked up summer.)

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Ben (Previously Guy NY)
Quickies in New York

Previously Guy New York. Writer of books and taker of pictures.