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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Mallory is always very thoughtful and great at making you feel better. 5 stars are not enough – She is simply GREAT!
There is no doubt in my mind that I will be calling Aileen again! I would probably call her every day, Maybe even more than one time a day! She is that good.
I took advantage of an unexpected chance to call Vicky, and I am glad I did. She was fun, sexy, and naughty as always. Her Spanish whispers were intoxicating. She had me floating in some very exhilarating headspace.
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There is only one Goddess Aileen. There has never been a Goddess Aileen before. There will never be a Goddess Aileen again, although She is eternal of course. You need to experience the perfection of Goddess Aileen for yourself while you can. I love ❤️ my Goddess Aileen, and I worship Her, and I’m proud to be Her devout disciple.
Vanessa and Vicky are amazing by themselves, but you put them both together it’s double the fun! Especially when Vicky starts talking in Spanish when she is upset with you.
Vicky and Vanessa are amazing by themselves but you put them both together and it’s double the fun especially when Vicky starts talking in Spanish when she is upset with you.
Romi has a way with words. Spending time with her is more than I thought it would be! How could I have missed her all this time? I love that she likes to explore and doesn’t have boundaries on what fun can be. #1
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Scarlett is absolutely AMAZING! Her verbal and intellectual skills are unsurpassed! She takes my fantasy and runs with it! She makes it come alive! She is simply the BEST! HIGHLY SATISFIED AND RECOMMENDED!
Valerie was beyond amazing!! She may be new here but she definitely is not new to this world. She has taken me to heights of ecstasy that I have been only taken a handful of times. She is sensual, adorable, cock-draining!! If I could give more stars I surely would!! Definitely will call back for sure……omfg and her role play skills are unheard of!!