Chastity Caption.

Of your three “regular” babysitters, she was undoubtedly the nicest. She at least did the least to humiliate or tease you.

One babysitter used her time with you to let out her inner Domme. She was exceedingly strict and any disobedience, even if it was a miscommunication, resulted in punishment. And she was extremely creative with punishments.

Your other babysitter loved nothing more to tease and humiliate you. Whether it was inviting her friends over to taunt the “diaper boy,” or just spending the entire night in Gryffindor-colored bra and panties, with thigh-high Gryffindor socks, making you wish you were a man, she left you would be positively aching down there with insatiable arousal.

But she was different. She wasn’t mean. She didn’t tease you. And, for some reason, you weren’t sure if that made her the worst.

If someone made an audio recording of her time with you, they would be convinced she was babysitting a toddler. It drove you crazy. It was one thing to be bossed around or teased. At least those babysitters acknowledged you were an adult, even if you were just a diaper boy.

But not her. Nothing she did, nothing she said, ever made it seem like she knew you were an adult. It was so convincing, so authentic that you honestly weren’t sure if it was an act.

She had never broken character once in the last five years. You tried everything you could think of to prove you were an adult, to force her to recognize—even for a second—that you were actually an adult.

Your attempts rolled off her like water on a duck. As far as you could tell, you were a toddler to her. She never let you out of her sight, except for your naps and sleepy time of course.

You had absolutely no dignity around her. She dressed you as she wished, checked you when she wished, and changed you when she wished. She blew raspberries on your tummy like it was completely normal.

You watched educational baby cartoons on a non-stop loop. And she always, always encouraged you to answer along and was just so proud of you for getting the right answers.

And nothing entertained her more than having you sing along with her to your “favorite” songs. You could never convince her you didn’t love singing and dancing to Baby Shark in nothing but a short T-shirt and soggy diaper.

All this because your bladder stopped working like it used to. All this because your girlfriend couldn’t handle your diapers but couldn’t break up with you.

But as you hear “The Wheels on the Bus” play for the 100th time, you know you need to start dancing…

Medical Restraints

I’m making a medical restraints (padded cuffs, straight he keys, etc) whump list so if you could reply with all your favorites I can add them to what I already have and making as complete a list as I can.

I don’t think I could ever do this pic justice.

Oh my word, I love everything about this.

Him, hooded, collared, tied, gagged - only the holes under the nostrils making the difference between being vulnerable and suffocating. He can hear his own heartbeat, the blood rushing through his veins, his scarce bodily hair standing on top, his skin, damp from sweat, registering every movement of air.

He is exposed, so exposed, so vulnerable.

He stirs under my gentle touches, under my fingertips brushing up and down his thighs, sometimes “accidentally” touching his cum filled balls. That’s when his cock, my cock, twitches manic in its cage.

I will claim him as my bitch, my slut, my whore, fuck his tight arse with my strap on. He knows this, because we both crave the same thing - my conquering of his body as much as his mind. My fucking and stretching of his boy pussy, with my fingers, my hand, my girl cock. But not yet. Later. When he thinks I’m done with him, when he believes I have forgotten about it. Later.

First, his nipples. His beautiful pink joy buds. I circle them with my fingers for a while, pinching lightly before adding little bites. I can tell from his muffled moans and his leaking cock how much he likes this. But it’s not enough, today I want to overload his senses. It’s time for the clamps, and to be honest with you, I almost feel physical pain myself when their little teeth bite into his sensitive skin. He will take the pain. For me. And maybe because he’s a little pain slut. It does not matter, because I decide when, where and how. My rules.

As the clamps dig into his flesh and he realises what’s happening to him, his body convulses. I give him a few seconds to adjust, slowly caressing his face over the hood while blowing cool breath on his nips.

“Are you ok my love?” I ask, my lips almost touching the leather of his hood. He can hear me and nods. “Talk to me my boy” … “Yff, yff m k” - I have learnt to understand what he says into his gag. I caress his hood again, kissing it on the forehead, both cheeks, over the gag. We love this intimacy.

My lips close around his nose and immediately his body tenses. So vulnerable. Then he realises I’m breathing for both of us and starts inhaling my breath. He is now literally clinging onto me for sheer life. So much responsibility. So much trust. So much intimacy. I got you, babe, don’t worry.

As he calms and eases into my rhythm, my hands find the clamps and start toying with them - more distraction, more sensual overload for him. He sucks the air out of me, breathing heavily as I slowly start pulling the nipple chain.

More cage twitching, more leaking. I smile, happy and proud, and release my lips from around his nose. I grant him a few seconds of fresh air supply.

“You are a good boy, aren’t you?” He nods “yff, yrs” (“yes, yours” - sweet, huh?) “And do you like being at my mercy like that?” Vigorous nod “yff, yff I d..” More caressing of his face through the leather hood, more slight pulling of the nipple chain. Instant reaction in the cage, rivers of delicious cock tears oozing out of the metal bars restraining his erection. “I will show you what truly being at my mercy feels like …”

And with that I place the palm of my hand under his chin, pushing his lower jaw upwards, harder into the gag inside the hood, while my fingers close around the nostrils and block all of his oxygen supply off.

I can see his internal fight to remain calm. He has literally no way out of this if I don’t let him.

At my mercy - he now understands the full impact of these three words.

“Ssshhh, calm” I reassure him. “You’re mine and you’re safe!”

Was it blackmail? Yes. The brat knew she had you by the balls and she intends to milk you dry in every way.

If only you kept your hands to yourself.