Alyssa Milano

Perhaps someone is wondering how the retribution for bad behavior begins.

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At an elegant restaurant, nestled beneath the table, the snow-speckled leather of her high-heeled boots faced you, alongside the polished pair of another man’s boots. The trace of grit on her heels and the remnants of snow were all you needed to know.

You didn’t need her command. As her devoted cuck, you leaned forward, your purpose clear: to lick their boots clean, humbly and without hesitation, while they ignore you while they kiss

Again

When you see a hot girl in public you need to immediately focus on her shoes. No matter how clothed she is, you do not deserve to look anywhere else!

Trust and respect: When using a chastity cage, build mutual trust and respect, avoiding any behaviors that exceed each other's comfort levels.

Heart-Shaped Box

“Wow, this is so nice! I’m so impressed, cutie!” your babysitter said, “Did you set this all up by yourself without your Mommy helping?”

Your heart sank. All you wanted was to show Claire you weren’t a baby—you were an adult!

Claire was your newest babysitter, though you hated that term. You were so sick of these babysitters seeing you as nothing but an overgrown toddler.

So, you were determined to break the cycle with Claire. Determined to show her you were a man. And what better way to do that than a picnic date?

Sure, Mommy helped you prepare the picnic. You needed her help putting things together.

And sure, there were some setbacks to your plan. Like the messy diaper change lesson Mommy gave Claire the first day you met her. And then you listened to Mommy tell Claire all about your infantile rules and needs right in front of you.

But it didn’t matter. You’d prove to Claire you were more than some adorable, helpless pamper packer. She was so beautiful. So cool.

You had to show her you were an equal.

“You know, I’m not some helpless baby, Claire. I’m two years older than you. I can handle myself!” you said confidently.

Claire stared at you for what seemed an eternity, clearly bemused. You could tell she was searching for the right words.

She sighs deeply. “Look, Benny, don’t make this weird. This is nothing more than a fun activity with your babysitter, okay? This is not a date.”

You were prepared for this; you already practiced the perfect response. “Then why did you agree to a picnic with me? Babysitters don’t go on romantic picnics, do they?”

“Romantic? Do you really think this is romantic? Sweetie, there is nothing romantic about this! I’m not here because I’m interested in you. You know that, right? Your Mommy is paying me to be here!”

“Who cares!” you retort, brushing off her comments, “You agreed to the picnic! Obviously, you want to be here. If all you wanted to do was “babysit” then why didn’t we stay home?”

“Fine,” she hissed, “If this is how you’re going to act, then I wont feel bad telling you the truth. Want to know why I agreed? Because I pitied you. You’re 26 but you live like a toddler! I mean, come on, dude! You’re in diapers and have a Mommy!”

“But that’s just…pretend! It’s not real! I’m not an actual toddler.”

Claire laughs wildly. “Not real? Seriously? That diaper between your legs is real. The poop your Mommy wiped off your tush was definitely real. The money your Mommy is paying me is real. The list of rules and punishments I was given are real. You are a real toddler to me!”

“That’s not what I meant!” you whine.

“Honey, I don’t care what you meant. Did you honestly believe I could see you as anything else? I watched your Mommy lay you on a changing table in nothing but a poopy diaper, rip open your diaper, wipe your poop off you, sprinkle baby powder, and put you in a new diaper.”

“The whole time,” she continued, “You sucked on a paci and giggled when your Mommy told you were her ‘perfect little pamper packer.’ You squealed—literally squealed in delight—when your Mommy blew raspberries on your tummy. And then thanked your Mommy for the clean diaper.”

“I have never seen anything that pathetically adorable in my life. I cannot fathom anything less sexually attractive than that. Don’t get me wrong—it was adorable—but adorable in an ‘awwww, how precious!’ way. The only thing difference between you and a toddler is your size.”

“So, no, sweetie. This is not romantic. It’s sweet and thoughtful, yes. But in the same way a toddler I’m babysitting brings me a dandelion he picked. You’re the sweet toddler handing me a dandelion. I’ll coo and tell you I love this, just like I’d tell that toddler. But I would never, ever, consider it romantic.”

She stopped as suddenly as she started. Her words hung in the air.

“Oh, honey,” she said, rubbing your shoulder, “Don’t pout! I didn’t mean to be mean! I just wanted to be honest. Our time together will be much more enjoyable when you accept that I am your babysitter and you are the baby. Nothing more, okay?”

You try to say something. Anything to save your dignity. “B-but…”

“No buts, little one. All I want to hear from you is ‘Yes, Miss Claire!’ Got it?”

You feel your face burning in shame. “Y-yes, Miss Claire…”

“Good boy!” she cheers, “Now, let’s forget all about that, okay?”

“O-okay, Miss Claire.”

“What a cutie! Now, let’s see what your Mommy packed to eat!”

Claire opens the picnic basket, pulling out its contents. “Oh, look! Peanut butter and jelly sammies!”

“I helped make it!” you said proudly.

“Wow! Mommy’s little chef huh?”

Claire handed you a sandwich. You both ate excitedly, with Claire assuring you it was the best PB & J she’s ever had in her life.

“What do you wanna do now, cutie?” Claire asked sweetly.

As you looked up at her, all you could think about was how beautiful she was.

“Ummm,” you mumble.

“Oh, look!” Claire interrupted, “Your Mommy packed us some cake! Want some?”

“Yes please!” you answer, reaching out for the plate of cake.

As you do, a loud toot breaks the silence. Your eyes go wide in terror as you feel the unmistakable churn of your tummy.

“Uh oh!” Claire says, “Do you have a rumbly tummy, Benny?”

Your body answers for you. You grunt loudly as you push, leaning forward unconsciously to better aid the process. You feel the first wave of mess fill your diaper.

You can feel Claire staring at you. You know you’re proving her right—you’re exactly what she said you were.

“Don’t worry, Benny! Just push!” Claire says, rubbing your back, “Push all the stinkies into your diaper. That’s what it’s there for. I have everything I need to change you when you finish.”

You continue to push, struggling to empty your tummy. Finally, with one last grunt, it’s over.

“All done, Benny?” Claire coos.

“M-mhm,” you answer sheepishly.

“Benny, don’t be embarrassed! I know you can’t help it! That’s why I’m here! I’m your babysitter! And babysitters take care of poopy diapers!”

You don’t answer, face burning red.

“Oh, come here, honey,” Claire says, pointing to the changing pat laid out, “Lay down and Miss Claire will get you alllll clean!”

You obey her, feeling your mess smush against the ground.

“What did I say, Mister?” Claire said in a mock angry voice, “Don’t pout over poopy diapers or I’m gonna—” Claire starts before pulling up your shirt and blowing a series of raspberries on your tummy, “Gonna give you the giggles!”

Claire blows more raspberries. Despite every fiber of your pride resisting, you giggle. Slowly at first. But as she blows a loud raspberry, tickling your sides, you burst into uncontrollable laughter.

“There’s my happy boy!” Claire says triumphantly, “Now let’s get you out of this icky diaper!”

A forced orgasm through a metal chastity cage isn't very satisfying for you, no. But knowing there is no real NEED for me to ever unlock you, that I can do whatever I want to you, well. It's pretty fucking satisfying for me.