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.
“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.
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 has no idea what is in store for him today. That makes me very happy, knowing that he is ready and wanting 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.
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Still getting to know Jamie, but our calls have been phenomenal. Jamie has “thrown herself” (I hope she laughs when she reads this) into my fantasy with both care and abandon. She listened to me carefully, ran the role-play exactly as I’d hoped, and then threw in her own totally appropriate and totally wicked ideas to take it up a notch.
There really aren’t many superlatives left for Avalon after so many calls, but perhaps she will appreciate this one. I never understood what a GFE was until I started calling Avalon. She is astonishingly good.
Karina is so attentive and detailed to my needs. She is excellent at listening and gives me the best experience. Call her!!
I love Sloane to the death! She has a great personality and is amazing at what she does!
Sloane is the best! She’s sexy, smart, a great conversationalist, and has a fiendish laugh that is infectious. She’s adaptable and is incredibly imaginative. Talking to Sloane is an experience in itself. You need to call her.
Eden is amazing! Her voice is soft and sweet, she knows just what to say and how to say it. The call was hot, sexy, and steamy. It was the perfect ending to my evening.
Jami made my Friday night! I couldn’t go out to play so she helped me out by providing me with exceptional role play. We agreed on the role play and she provided me with an exceptional experience. I wish I could chat with Jamie every day. She is a huge asset to PSK!
Vivian is Hot! She was a lot of fun to play with!!
Last night was once again extremely sexual. Gorgeous Romi lead me to an incredible orgasm. She was so relaxed and lead me into an incredible ending. She is so good and kind at what she does to me every time I call her.
Kali is downright amazing. She must be as beautiful as her voice is. I have had numerous abdl related calls with Kali as well as Mommy Megan and also calls with them separately. Kali is a must call. She will rock your world as both Kali and Megan have done for me numerous times
Gia is incredible! She is smart, sexy, naughty, and accommodating. She is genuine, beautiful, and has an inviting voice. She can adapt to any desire or genre. She really is outstanding. Do yourself a favor and call her.
Mommy Violet was a different kind of Mommy/abdl call for me. Violet is so creative and was almost like mommy dearest in some ways. Mommy Violet was like unwrapping a candy bar to be surprised with the filling or what is underneath. Violet at one point wanted to find a daddy for me at all costs but I rebelled and wanted Mommy all to myself. hehehe –