18 - Choose Wisely ✔

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Stiles's Point of View

"So, your punishment is edging," he says.

"What no please no sir," I beg.

"I've already made up my mind and I will not change it but I do like to see you beg, pup," he says.

I sigh and drop my head. I can't believe I'm going to be edged. Sometimes it's nice but not for punishment. If it were for play because at the end you normally get to cum but I have a feeling I won't today. But I will not complain or even ask because maybe if I handle my punishment well then maybe he'll show me mercy. I hope at least.

"So, now that you know what your punishment is I want you to go to my closet and pick five items that you want me to use on you. If you pick items I deem too weak or not good then I will be putting it back and get two stronger items to use. Do you understand?" he demands.

"Yes, sir,"

"Good. Go to my closet and pick wisely," he says.

I unclasp my hands from behind my back and slowly push myself up from the floor. I go to his closet placing my hand on the doorknob. I look over my shoulder to him, silently asking for permission to open it. He nods his head in agreement. I turn the knob and push the door open. I walk in and I realize this is like a mini playroom. He obviously doesn't have every single piece of equipment from his club but he has most of the small things. 

I look around the small room taking in all the items hanging on the walls and the labeled drawers of the several dressers. I see floggers and whips hanging on the wall along with rope and other things I'm honestly not sure what they are. 

I look at the labels, some say dildos, vibrators, cock rings, handcuffs, butt plugs, cock plugs, and many more. I wonder if he would mind if I grabbed more than five things but he said five so I should probably follow his orders. I stand there looking around for the five things I'm going to choose. I have to be wise because I don't want him any more upset at me than he already is. 

Finally, I have chosen my five items. I pick my items from their places and bring them into the bedroom. 

"You can set them on the bed and I will go through them and determine if they meet my standards," he says.

"Yes, sir," I say and set them on the bed.

I stand a foot back from the bed clasping my hands behind my back standing up straight. Derek comes to the bed and starts looking through the items I picked. I hope they are up to his standard because I do not want to disappoint him. 

"So...," he trails off.

My breath hitches in my throat, I have no idea what he's going to say. I cannot read his face. He is keeping all expressions off his face which is making me so nervous.

"I like them, but I really like the cock ring and prostate massager," he praises.

"Thank you, sir," I respond softly.

"You picked handcuffs, a cock ring, a prostate massager, a dildo, and a flogger. Those are a really good choice but please explain them to me," he says.

"What do you mean, sir?" I ask.

"Why did you pick those items?" he asks.

"Oh um, I picked the handcuffs because I know that I will try to grab anything I can and I don't want to be in your way or interrupt you," I explain.

"That's kind of you to think of me but I know you just wanted to make sure you didn't get more punishment but no worries, it was good thinking," he laughs. 

I let out a small chuckle.

"Okay, next item,"

"I picked the cock ring because I know I have a hard time controlling my orgasms and I did not want to cum if you told me not too," I explain.

"Good. Next?"

"I choose a prostate massager because I figured it give you something to sexually torture me with," I smile.

"Okay, it seems like a reasonable explanation. Next?"

"I picked the dildo because it's a standard regular toy to play with," I say.

"Next?"

"And finally I chose the flogger because it was different than the others I chose and I know I enjoy some flogging. I mean I know I'm not supposed to enjoy this but I figured if I chose items I liked then it would be easier to edge me I guess," I explain.

"Good, good. I like that you put some thought into each item. It shows that you actually tried to pick good items and not just choosing the things you'd think would be easy to handle," he praises.

"Thank you, sir," I breathe out.

"You're welcome, pup," 

He walks towards me and runs his hand through my hair.

I whine.

"What's up, pup?"

"I like when you call me pup," I mumble.

"Good because I will continue to call you that," he says.

I let out a deep breath.

"Would you like to pick your position or would you rather me pick your position?" he asks.

"I would prefer to be on my back but whatever you want, sir," I answer.

"Such a good, pup. You always have the right answers," he praises.

I whine again.

"Oh, right. You're a praise slut," he whispers in my ear as he tugs at my hair tighter.

I moan in response. 

"Let's get you on the bed,"

He lets go of my hair and moves the items from the bed to the nightstand.

"Now, come over here and lie on your back, pup," he orders.

I do as he says.

"Put your hands above your head," he says.

I raise my hands above my head so I can touch the headboard. He grabs the handcuffs and places them around my wrists so they are handcuffed to the headboard. 

"Tug on them,"

I gently tug on the handcuffs.

"Is it too tight? too loose? just right?" he asks.

"They are fine, sir," I say.

"Good. If they ever become uncomfortable tell me and I will fix them, okay?"

"Yes, sir," I reply.

"Good. Now if you're ready, I am too, so let's get started," he smirks.

I have no idea what he is going to do with everything I chose and I have no idea how long he is going to tease and edge me. I hope he isn't too hard on me but I do realize that this is a punishment and not supposed to be enjoyable so I can't hope for too much mercy from him. I see him grab the flogger.

"I am going to warm up your skin a bit," he says.

This is going to be fun.






Number of Words: 1175

Published: June 15, 2020

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