I love my sissy boys, but I love dressing them up even more. My sissy boys would often come over to chat and make sure they were being as feminine as possible. Of course, I would also dominate them when they were all prettied up. It makes my own silky panties wetter when I have a grown man wearing lacey panties and silky thigh-high garters, especially if I have them crawling around begging for mercy! As soon as they come over to my home, I guide them to my sex room and pull out my whip, yelling, “DRESS UP, SISSY BOY!”
Oftentimes, I dress up with my sissy boys; they’re like my pretty friends. I try on clothes with them and help them choose their outfit. But today, I’m getting rougher with this new sissy boy of mine, I call him Ava now. As soon as he comes over, I pull him inside and order, “Dress up, sissy boy!” I pull off Ava’s clothes as I smack him around. Dressed in leather and studs, I stand tall in my platform heels as Ava takes my hits. With my free hand, I strip him naked. My sissy boy loses his masculinity by the second. I lead my sissy to my sex room where all my sissy’s boys’ attire is hidden away. Once we got there, I was ready to say the magic words:
Ava runs over to the closet and pleads, “Please Miss, may I wear the crotchless panties under my slutty dress?”
I smirk and reply, “Only if you kiss my heels.” Ava gets back on all fours and crawls to my feet. She kisses my heels and makes sure to slobber his tongue like a dirty whore. I make my sissy slave get back up and grab the red bodycon dress. “Time to dress up, sissy boy. We’ll be late for our night out if you don’t hurry.”
As my sissy boy is putting on his bra, panties, and thigh-high stockings with garters, I call the cab. Before we leave, I make sure my sissy boy knows we will have company tonight.
I ask my Ava as we get our drinks paid for at the bar by the strapping young men. I smile as I tell my sissy that I’ll make sure her boy-pussy is properly fucked tonight, but only if she behaves and obeys. She’s allowed to drink prosecco only and must ask my permission if she wants to leave. As the drinks flow, my sissy boy begins to make eyes at her arranged date.
Ava asks submissively, “Can I leave with him? I can tell he has a big cock, I can see it tenting his pants.” Oh dear, my little dress-up sissy boy wants her boy-pussy fucked, and it’s not even 11 pm. I can’t have her do this alone!
“Only if I can come with you, I need to make sure you open up my Ava’s holes correctly.”
When we get to the hotel, Ava pulls up her dress to show off her garters. Her bottom is red from all the spanking that her arranged date and I gave her. I spread her cheeks wide as Ava’s date penetrates her boy-pussy. Ava shouts how good the cock feels in her tight asshole. My dress-up sissy boy was taking that cock like a seasoned whore. When Ava’s date starts moaning, I make my sissy turn around and open her bright red lips. Ava’s lipstick stains that big cock as her date blows his load into her mouth. I smack Ava’s face and order, “Swallow it, gorgeous!” She obliges, of course, and I take my sissy home and slip off her feminine clothes. “See you next week, my sissy bitch.”
Get your panties on and silky stockings up! Then call Kiera and check out more cock training too!
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