Sitter



He heard the doorbell, looked at the clock across the room, was puzzled, for it was too early for his wife's boyfriend to arrive, he wasn't due for at least half an hour.

"Right on time," his wife said walking into the bedroom from the bathroom where she was getting dressed, a white satin robe over her bra, panty, garter belt, and stocking set.

His eyes went wide seeing her in her lingerie, she generally wouldn't show him what she wore for her boyfriend, left it up to his imagination. "Mmmmgggffff," he moaned through the cock gag secured in his mouth.

She paused, looked at him, giggled. "You're drooling, love," she said, watching the small drop of drool fall onto his stocking covered legs.

He watched her walk from the room, jealous that it was her boyfriend, not him, that she dressed for.

"You're right on time," he heard his wife say as she opened the door, still not sure why her boyfriend was early. "I was just finishing getting dressed, why don't you come back here so I can introduce you."

Introduce? What did she mean by that? He'd met her boyfriend before.

But it wasn't her boyfriend who followed his wife, it was a young woman in her early 20s wearing a shiny pink leotard, gold skin-tight boots, gloves, and carrying a crop.


"Lilly, this is my sissy, sissy, this is Lilly, she's going to be babysitting tonight."

"Mmmgffff," he moaned as the pretty, young woman walked up to him.

"Sorry?" Lilly said.

His wife stuck her head back into the bedroom. "Sorry, she's gagged," his wife said. "You can take it out after I leave if she behaves, or leave it in, it's your choice."

"It's not a ball gag?" Lilly said, looking closely at his face.

His wife smiled. "Angela said you were observant. No, it's a cock gag, she's on a training program." His wife ducked back into the bathroom.

Lilly moved closer, touched his stocking covered leg with her crop; he shuddered, mortified, not understanding what was happening. "Its caged?" Lilly called to the bathroom.

His wife walked into the room, dressed now. "Caged? Of course, semi-permanently now. Sorry, it has to stay on, my boyfriend holds the key."

"Naturally," Lilly said, reaching between his legs with her gloved hand. "I'd require it regardless. Where does it sleep?"

His wife giggle. "It. That's so mean. Cute, but mean. I have a schedule written out. Her...its... room is in the basement, it's locked, of course. The room, like everything. There's a cage, too, if she...it...misbehaves."

"And bedtime?"

"Ten, usually, but that's up to you, of course."

"It might be later, I like to play before bed, especially when when its caged."

His wife laughed. "Of course. I left the important numbers on the note on the table, my cell, my boyfriend's cell, and all that."

"And you'll be home..."

"I think he said Sunday before dinner," his wife said.

Sunday? He looked up. Sunday?

"Does that work for you?"

"Of course, that's close to two days, that should be enough. Oh, before I forget, when was its last release?"

"I milked her, let's see, five weeks ago. She's about due, but I assumed you'd want her on edge for the weekend."

"It's usually for the best," Lilly said, "they're usually nervous to be left alone with a sitter, I find when they're on edge, they're easier to control." Lilly reached between his legs again, massaged his caged penis. He moaned, started sucking on the cock gag again, drooled again. "Isn't that right, sissy?"

"Mgggmmffff."

"Don't worry, sissy, you won't have any release from me. I'm more of the teasing sort, the love to see a sissy beg sort."

"Mgggfffmmm," he looked at his wife.

"Don't look at me," she said, "this is your doing, not mine. She was all secrets when we got married," his wife explained to the sitter, "I found this stash of horrifying porn on her computer."

"A tale as old as time," the sitter said. "Or at least as old as the internet."

His wife laughed. "I'm just glad to have found a sitter, I hated leaving her home alone. Plus she could use the training."


Comments

  1. PLEASE! Expand this to a book! You just hit every one of my buttons at once...

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  2. I really like the idea of a babysitter. Often times, when stories involve leaving someone in bondage unattended, it breaks immersion because in real life, this would be quite unsafe. Leaving the sissy with a babysitter seems only logical. And the idea of introducing someone new to the helpless sissy is quite intoxicating. :)

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