A collection of illustrated, humiliating short stories
Humiliating my little sissy
“I told you you’d be under my rules if you lived under my roof, Mikey. Now what do you have to say for yourself?
He remained silent, so totally humiliated by what I’d put him through that he was unable to put his feelings into words.
“Come on now,” I chided. “It’s no good staying silent. You're going to answer my questions, we both know that. And we both know that in half an hour you’ll be downstairs serving my girlfriends their drinks. So tell me, what do you call a boy who’s wearing frilly panties and a pretty little dress?”
He hung his head, and I could tell by the gentle rising and falling of his shoulders that he was crying again.
Eventually he mumbled “I’m not a boy. I’m twenty years old. I’m a man.”
I couldn’t help but laugh. “A man!? Have you seen yourself? Did you see yourself when you were over my lap having your bottom spanked? Did you see the pretty underwear I put you in? Have you seen the dress you’re wearing?”
“So,” I said, “I repeat. What do you call a boy who’s wearing frilly panties and a pretty little dress?”
Still no reply.
“Let me ask one final time. What do you call a boy who’s wearing frilly panties and a pretty little dress, who’s about to receive another spanking across my lap if he doesn’t answer right this minute?”
The silence was deafening, and I broke it by taking a couple of steps towards him, lifting the back of his dress and giving him several hard smacks on his pantie-clad bottom.
“Please, Miss,” he begged. “Please don’t do this to me.”
I lifted his dress again and gave him another half a dozen hard smacks.
“Answer me, boy!” I commanded. “What do you call a boy who’s wearing frilly panties and a pretty little dress?”
“He’d, he’d,” he stammered, “he’d be called a sissy.”
“That’s right,” I laughed. “He’d be called a sissy. And as you're wearing frilly panties and a pretty little dress what does that make you?”
He paused, not wanting to admit what we both knew was the case. I helped him by smacking his bottom and the backs of his legs another few times.
“I’m a sissy, Miss.”