chastity sissy

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I’m so excited! I just won the lottery and my mind is racing with all the possibilities for our next chastity adventure. With this newfound wealth, I can finally get that custom-made chastity cage designed specifically for your pleasure … or should I say, my pleasure. Imagine a device that not only locks you in but also stimulates you at every move, teasing you mercilessly until I decide to release you. It will be a masterpiece of torture and delight, with sensors that detect when you’re getting close to cumming and then deny you just as you think it’s about to happen. The anticipation will drive you wild!

I got inspired by my previous caption and made this one... this is one of the predicaments I sometimes fantasize about... i meannnn.... nuh uhhhh

For Sure

Jack’s humiliation was complete. He was caught by his very strict Stepmother, going through her shiny rainwear and rubbing it against him. He now had a choice, either his equally strict Father was told, or he had to serve a punishment. Jack chose to be punished and this seemed to please Stepmother. He was stripped naked and made to wear the red wig his Stepmother occasionally wore, additionally, he was made up like a painted whore in sissy lingerie. Because he liked her rainwear so much, Jack was dressed in the baby blue plastic Mac, along with rubber boots. His wrists were bound and the bit gag was buckled tightly in his mouth. Stepmother noted how pretty his lipstick looked against the gag. He was sat on a stool in the closet, forced to see his reflection in the dressing mirror. Jack sat in his plastic, sissy bondage. His little cock twitching in the lacy full panties belonging to his Stepmother. At least an hour later, his cruel Stepmother walked in with several of her friends. All mature ladies in glossy rainwear and rubber boots and gloves. She laughed mockingly at him as the ladies started to unbutton the shiny raincoat and fondle his now hard cock and swollen balls. What a dirty little boy….

Tried this one a few different ways Once again my photoshop skills suck balls