I love to humiliate my pets by requiring them to wear women’s clothes and taunt them about what would happen if they are caught crossdressing.

I never expect them to actually get caught crossdressing, of course, but I can’t be held responsible for dumb bitches that have no idea how to keep things on the down low.

Case in point: one of my CEO sissy boys confessed his love of all things girly to me, adding that he hadn’t ever had the nerve to actually wear any of his frilly sissy panties or stockings outside his house. Of course, as far as I was concerned, that assignment made itself!

I told him to go get a sissy manicure and pedicure, have his toes painted a lovely dark red color, and wear pantyhose (without socks) to work every day for a week. I thought he was going to faint after I gave him his assignment, but to his credit, he promised he’d do as I demanded.

Everything went fine at first, but one day, his assistant surprised him while he was walking around his office in pantyhose without shoes!

Busted! He told me he was absolutely sure she saw his red toenails and nude pantyhose. He said she looked down for a few seconds, then tried to cover up how flustered she was seeing him in such a state. Later, he overheard her talking to her colleague’s assistant. They were urgently whispering and giggling.

“Oh my goodness! He was standing there in pantyhose with his toenails painted bright red! Do you think he’s one of those cross dressers, or do you think he’s gay?”

The two women laughed and joked that he probably had on a matching bra and panty set! He was completely humiliated that he had gotten caught crossdressing. The only thing more humiliating than hearing them laugh was the fact that he dove into his private washroom to indulge in some crossdresser masturbation thinking about what they had said about him.

Of course, this was only the beginning. After this, I began planning our next attempt to get him caught crossdressing!

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