Tiffany’s Sissy School

My First Student

All kinds came to my sissy school. Nothing about him stood out to me. He was your average all-American guy. Work boots, Levi’s and a T-shirt. His physique was muscular, and his appearance was rugged. I could tell this was a hard-working “man’s man” which is fine by me. The bigger they are, the harder they fall, so to speak. I love a challenge; my preference is a sucker for punishment. He walked in with a very dominant and masculine energy. He casually introduces himself as “Mike” with an outstretched hand. My own arms remained folded just under my ample breasts. I’m dressed in a leather leotard, corset, fishnets, and 8-inch patent leather stiletto boots. Nothing about my demeanor could have led to any confusion.

We are not equals, he will know better than to approach me as if we are.

This is Tiffany’s sissy school ‘I let my hands fall to my side as I began examining him. “I am Mistress Tiffany. You will address me as such. There are no safe words; you will be pushed beyond your limits. If something hurts, it should. If you’re embarrassed, you should be. Do not interrupt. Do not speak unless you are spoken to. If I tell you to do something, make it easy on yourself and do it. Only a good little Sissy boy, you will thoroughly enjoy our time together. If you’re not – I will. Understood?”

“Yes, ma’am,” he replies. Great, I think to myself, he doesn’t listen well. “Excuse me?” I say, standing squarely before him, my heels bringing me just above his eye. He begins to stammer, “I’m sorry, Mistress Tiffany”. “Not a problem, but I do not repeat myself, nor do I accept apologies,” I say with a chuckle. “Now, Strip completely,” I demand.

Welcome to Tiffany’s Sissy School.

He looks as if he wanted to talk back but must’ve rethought his choices as he began stripping. Once, he was completely naked,  attempting to shield his cock from me. I pointed toward my leather bench and told him to kneel over it. He did as instructed. “Don’t worry; I’ll make a good sissy out of you, Mike.” I grabbed my leather wrist cuffs and fastened his wrists around the legs of my bench to prevent squirming. With that, I grab my firmest riding crop and begin. I trail the insides of his thighs with my crop and begin tapping his thighs and ballsack as he clenches.

“Now, do you remember my name, Mike?” I ask. “ Yes, mistress Tiffany”. He responds. “Good. Now, hopefully, we don’t need to repeat this”. “Mike, you came in looking a little too masculine; I don’t like my sissy in that attire. I actually like my sissy’s a little slutty, plus it’s part of the sissy school training attire. Have you ever worn fishnets?”

He chuckles while shaking his head no. I grab a large set of fishnets.

I believe it to be his size, then pull them on; once on, I give his tush a nice smack, which makes him wince a little from the sting. “See better already, you know what else I like? I like to stretch my little sissy’s pussy”. He begins to object, “No, no, I’m okay with just the fishnets and whip.” I chuckle as I pull out an 8-inch metal butt plug and lean to his face as I begin lubing my butt plug. Just then, I grab a cock chamber. Reminding him again this is Tiffany’s sissy school! “Oh, I’m sure you’re ok, but if I don’t show you how to be a good little sissy bitch, who will Mike?”  I ask. “No one, Mistress Tiffany,” he responds. “That’s right, no one, so I will”

 I rip the crotch and ass open so I can easily access him. Then I begin cupping his balls and giving walk around, trailing my gloved hand down his back. I snap the waist of his fishnets. Then mount me behind g his cock for a nice stroke. He begins to moan. “Oh, you like that, my good little sissy boy?” He loves to be here in Tiffany’s sissy school.  
While stroking his cock with my other hand, I ready my cock cage. Then I put his cock and balls in a latch lock. I pull out a necklace, put the key on, and place it around my neck. Letting it fall just between my tits. Then I walk back, leaning down so he can see the key around my neck.

“Try to be good sissy. If your cock gets too hard, it’s going to hurt.”

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