Prince

"...Prince!" Jeff puts the package in your hands.

You take one look and almost gasp. "S-sir! this says Hot Princess! I can't wear this!" The picture on the front only vaguely resembles a princess, in that she's wearing mostly pink, and has a tiara and white opera gloves. But the 'gown' is a skimpy mini-dress and she's wearing a pink choker necklace that says 'Save me! <3' on it. It also had pink boy short panties that had the words “Daddy’s Princess” written on the butt.

Jeff looks completely unmoved by your **** outcry, despite the fact that your face must be as red as a tomato. "Hmm? Oh, I guess I grabbed the wrong one. Ah well, it's Halloween. Nothing we can do now. Just try it on - I'll bet it still fits!"

"B-b-but, Sir! It has a skirt!" You're practically pleading at this point. He could not be serious. There's no way he would make you cross-dress just for some dumb office Halloween thing. And right after shaving your legs... "Please, Sir! Can't I just go as, like... an anime character or something? I'm pretty sure I have a Goku shirt that still fits..."

Jeff laughs. "Don't be a baby, Aiken! It's just a costume. You don't even know anyone from my office. AND it's Halloween - you're supposed to dress up as something weird! And do you really think anyone from my office will know any of your little anime characters? I already paid for a perfectly good costume, so you're wearing it. End of story."

"But-!"

"Aiken! Do you want a spanking?" Jeff raises an eyebrow and puts on his stern voice.

You hate how easily you cave under the threat of being spanked, but you could still remember the feeling of the first time in vivid detail. You shiver and bite your lip. You feel like crying, but all you can say is, "No Sir... I'll wear the costume..."

Jeff nods, placated for the time being. "Good boy. Your mom has some heels in her closet. You can put a pair of those on when you're done changing."

What?!?