Tiffany’s Sissy School & My Sissy Whore

He was questioning Tiffany’s sissy school ethics.

When could he remove the plug? Who the fuck cares when, just needs to know he can’t. Then, without warning, I stick one lubed finger into his tight asshole. He squealed a little. I could tell this was his first time being penetrated, so I went slowly while gripping his ass cheeks and slightly spreading them. Then, I inserted another finger while making a come-hither motion, which made him moan. “See, sissies are meant to have their little boy pussys fucked; you like that, don’t you, Mike?”

“Yes, mistress Tiffany,” he moaned. Then I sped up my pace while inserting a third finger and spanking him and gripping his ass with my other hand. I continue until I’m able to get my entire fist in, so I know I can get the butt plug in easily. I make sure it’s nicely lubed and begin inserting it into his ass which is still not as loose as I’d have liked it to be. He moans hard, then begins to relax into the feeling. The feeling of something he has never felt before.  But he clearly craves this feeling. If not why would he be in Tiffany’s sissy school? Today he will become a real sissy and get that cherry popped.

“Tiffany’s Sissy School offers pink or blue, which would you like?” I ask.

“Pink,” he responds. “Of course you do”. I go to my wardrobe and pull out a leather skirt over my leotard. Then I found a pastel pink mini dress and handed it to him.
He looks confused. As if he didn’t know that he signed up for Tiffany”s Sissy School. “Put it on and take off those fishnets; I don’t want everyone to think my sissy is a whore”. He begins telling me he’s not going out in this. I ignore it and grab a pink pair of heels and a blonde wig. He does as told and made a pretty decent looking sissy if I do say so myself. Then we were off to the boardwalk so I could show off my pretty little sissy. Sissy’s love when you show them off.

“Are you going to take the cage off, and can I take out the plugs?”

Then I turn off the lights and motion to the door. My dungeon is on a busy street in the downtown area, so I assume there’d be plenty of traffic. He clumsily walked in heels, and it was noticeable that this was a new experience for him. He was noticeably uncomfortable, and people were gawking, which was bothering him. “Everyone is looking at me,” he says. Yes, they are. They know you are a part of Tiffany’s sissy school. This is going to be fun breaking him in. To the sissy I demand him to be. If you want to be around me and in my school. You have to be willing to be the sissy whore I want.

Well, hey, at least they don’t know your cock is in a cage, and your ass is filled with an 8-inch butt plug.

You’re my sissy; if I’m not embarrassed to walk with you, you shouldn’t be embarrassed to walk with me,” I laugh. I can see that my words perked him up a bit because he straightened his posture and began walking with confidence. He can thank me for the sissy school training.“Good, now sway your hips with me, give ’em something to see,” I said as we continued walking down the street. I am very proud that has turned out to be a great sissy. But then again

He is the first student at Tiffany’s sissy school.

He has no idea what is in store for him today. That makes me very happy, knowing that he is ready and wants to please me in every way.  Today he will come the sissy whore. He has always dreamed about it. My job as his teacher is to break him and make him. The ultimate sissy whore and that means.  He will be a two-hole wonder for who I see fit. I will have complete strangers enter this sissy’s holes. Maybe even two at a time will be in this sissy’s holes. I want him bent over and have cock in both of these sissies at the same time.

Call Tiffany 1-888-964-8863