A Misunderstanding Ch. 01

"No!" Shaun cried out in an automatic response as his mother cackled before him.

"We'll just have to see," Sierra shrugged. "Who knows, maybe you'll be too ashamed to ever ask mommy if she'll let you out of chastity. Maybe you'll just accept your fate and wallow in the humiliation and frustration of never coming to orgasm without your mother's permission again. Oh I do hope it doesn't come down to that though... Because mommy's really looking forward to telling you no for the first time... I honestly can't wait for the first time you get so hot and bothered in your little cage mommy has the keys to that you actually come and ask me if I'll let you masturbate. And if you aren't living up to mommy's expectations... if you aren't good and sweet and obedient to mommy and do everything mommy says at the snap of a finger... then mommy won't let you go touch yourself again. And without mommy's permission... without these two little keys you so generously sent mommy to hold onto... there is nothing you can do!" Sierra then burst into a fit of hilarity at her son's expense. "Nothing! Isn't that great?! Maybe not for you, but it's honestly my favorite part of this whole arrangement. That when you have to come to me and have to ask me if I'll let you go masturbate, there's absolutely nothing you can do about it when I tell you no. No, you have to just sit there and wallow in your frustration in that mean widdle chastity cage mommy keeps you all locked up in. I mean... I suppose you could just... y'know... try harder to convince mommy that you've earned yourself a little cummie. And maybe if I feel like you've done a lot to impress mommy, then maybe I'll consider feeling sorry enough for you to let you go rub one out. With mommy's permission of course," Sierra laughed some more. "Because that's your reality now sweetheart. There's nothing you can do about it. You agreed to mommy's terms of service and fully consented to putting the next orgasm you have into your mother's control. It's all up to me now. And if you don't want word of this trickling out to anybody besides your aunt Summer, I suggest you stay on your best behavior, and do everything you can to ensure mommy is happy. Because if you come to mommy asking if I'll unlock your chastity cage on a bad day, I won't hesitate to melt one of these keys down and make a fine piece of jewelry for myself to wear around as a reminder of the power I have over you. Maybe a necklace? A charm for an anklet? A nice set of earrings? Hell, maybe I'll make you give it to your aunt Summer as a birthday gift for her to wear. It'd certainly make for a nice inside joke between us, knowing that the set of earrings you got your aunt Summer are the melted remains of the keys to her nephew's chastity cage. Maybe your sister would like something too? A nice toe ring from her dear sweet little brother maybe? After all, I have two little keys here that aren't being used. Might as well give them another purpose, y'know?" Sierra cackled. "If they aren't being used by mommy to let my poor widdle boy have himself a widdle cummie someday, then they'll serve some other purpose. A charm dangling from your aunt Summer's anklet. A ring around your sister's toe. Both from none other than my poor widdle cock-locked son who wasn't a good enough boy for mommy to convince her to actually use them. Wouldn't that just be so unfortunate for you son? To have mommy keep your widdle dicklet all locked up in chastity forever?" Sierra couldn't keep herself from laughing.

Shaun was frozen. His mind was foggy to everything but the words his mother berated him with.

"So," Sierra concluded. "Now that you understand the stakes here young man, why don't you give mommy a kiss as a small example of what you're willing to do to convince me to use these keys mommy has to let you out of that mean ol' chastity device locked onto your boyhood." Sierra pointed a finger down to her open-toed high heeled foot. "Right here. Right on the tip of mommy's big toe peeking out of my stiletto. Give mommy a kiss right there on her big toe and show me you're ready to let me shape you into the young man I've always wanted."

Shaun quivered from his limbs to his lips as he peered down at his mother's red toenail poking out from her high heel. He knew this wouldn't even be close to the utter humiliation she was likely going to put him through. But with the power Shaun's mother held over him in those two little keys she held in her hand, Shaun knew that ignoring his mother's demands and going a lifetime without ever having an orgasm ever again would lead to unsatisfied frustration and humiliation that would build over for the rest of his life. So he lowered his face to the floor, closed his eyes, puckered his lips, and planted the first of what he feared to be many kisses onto the very tip of his mother's big toe peeking out from her open-toed stiletto.

"That's it," Sierra cooed. "That's a good boy. Mommy knew you'd see things my way. Now I suggest you keep up this obedience that has you literally kissing your mother's feet if you don't want your sister or anybody else finding out that your mother keeps you all locked up in chastity. That you aren't allowed to - or even able - to masturbate without your own mother's permission. If I let you that is," Sierra snickered. "Or I could skip the gossip and doll you up as mommy's personal little live-in French maid. I'm sure your sister Stella would get a kick out of that!" she laughed. "Now let's make sure mommy doesn't have to take her son shopping for his new maid's uniform or have to tell anybody that his mother keeps his dicklet locked in a cage by having you come rub mommy's feet for her. After that, mommy will show you how she wants you to shine her shoes for her every day. There are toe prints on the insoles of your mother's poor high heels here that have been steeping in there long enough that I don't even remember what the inside of these shoes looked like before I started caking on layer after layer of mommy's nasty workday foot sweat onto them! It's honestly nauseating to look at," Sierra laughed. "But don't worry son. Mommy will show you exactly how she expects you to keep her shoes clean for her. Every day. Every night when I come home from work after another long hard day in the office. That'll be your job son. But I'm sure you've seen enough of mommy's videos that you know how I'll expect you to clean them, don't you son?" Sierra laughed as she gave her son a playful wince and patted his head.

Unfortunately for Shaun, he was indeed well aware of how his mother made people clean her shoes for her in her videos. And much to Shaun's dismay, he always avoided those videos when browsing his - unbeknownst to him, at the time - own mother's pornographic content. Just not his cup of tea.