"Hey there, sweetheart. I've decided that today is the day you'll go out dressed as a girl for the first time."
Marcus stared at the message from his ex-girlfriend - now his mistress - in shock.
"I'll be there in two hours, so you'd better start getting ready. I want you to be wearing a full face of makeup and the sweetest, girliest outfit you can find in your new wardrobe when I arrive. If you don't, your little clitty will stay locked away for good. But honestly, this task shouldn't be too hard for you, since we've been practicing your makeup skills and your girly manners for so long."
Marcus had no choice but to comply. He never wanted to be a girl. He was a straight man! But ever since his ex-girlfriend had put that chastity cage on him a few months ago, she had emasculated him in so many humiliating ways that his masculinity seemed to slowly fade.
So he began getting ready by picking out the girliest outfit he could find and applying a thick layer of foundation, followed by an entire arsenal of makeup products, until his face looked flawlessly feminine.
"Ooooh don't you look fabulous, sissy!"
His ex-girfriend said as she spotted him putting on the finishing touches of his makeup.
"I absolutely love the outfit you chose for your first time in public!" She continued.
"But I really don't understand why you decided to wear those boring sneakers instead of a pair of high heels."
"I-I don't know, mistress, I just thought..." Marcus stuttered.
"I'm sure it must be because you couldn't find a pair of heels among the ones you already own that you thinks looks good enough - and not because you didn't bother practicing walking in them like I told you so many times." She said while raising one eyebrow with a look of playful suspicion.
Marcus could barely breathe. Of course he hadn't practiced walking in heels. It was simply too humiliating to wear them on his own.
"But don't worry, girlie. I've got just the perfect task for your special public outing day: you'll be walking all the way to the mall to buy yourself a pink pair of high heels to match your cute outfit. After that, you'll get rid of those nasty flat sneakers and walk home in your new pair of heels. The five-mile walk shouldn't take you too long, since you must be a pro in heels by now."
Marcus couldn't believe what he was hearing. There was no way, he'd be back before it was dark outside. How would people react to him, wearing such a revealing outfit in the dark?
His mistress made him pose for one last picture before she sent him on his way, a satisfied smile playing on her lips.
"Have fun sweetheart! For every ten minutes you take for your little shopping task, I'll be discarding two items from your male wardrobe. So you'd better start walking now, sissy. You wouldn't want to go to work wearing a dress and heels instead of regular clothes, would you?"
Marcus could barely hold back his tears as he reluctantly began his humiliating walk to the mall, silently praying that not too many people would notice him on his way there.
@alwayscute I hope you like the post I made for your caption challenge 🙈🫶🏻
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