A Misunderstanding Ch. 01

"I just never anticipated anything like this to happen," Sierra said on the phone to her sister Summer, "I'm... I'm in absolute disbelief! Like... I dunno... I just needed to get it off my chest to somebody..." Her sister didn't respond right away causing Sierra to ask, "Summer? You there?"

Summer had muted her phone upon bursting into laughter after hearing her sister's unexpected admission. The deep breaths of laughter toning down ushered the conversation to continue. "Oh my gosh!" Summer said, still fighting off chuckles. "Sorry, are you serious?!" Summer had to let a few more laughs out as they forced their way out of her system,

"Summer!" Sierra scolded, somewhat playfully. "This isn't funny!"

"Are you kidding me sis?!" Summer replied as she wiped tears from her face. "This is hilarious! Your son seriously saved up a grand mowing lawns so he could lock his dicklet into a chastity cage and actually pay a domme to keep the keys out of his hands?!" Summer had to let out some more laughs before she got to the real root of the hilarity taking place: "And little does he know, that domme is you?! His own..." she let out another chuckle, "His own mother!?"

"Summer!" Sierra struggled to hold back her laughter as well as she looked down at the two little keys in her hand; the keys to her own son's chastity device that kept him completely unable to pleasure himself in any way. She'd already let out the bulk of her hilarity when she first opened the package and realized whose keys she'd just received in the mail thanks to the pictures she demanded for her online services as a masked domme.

This side hustle of Sierra's started in college, and blew up near instantly. Summer was the only person who knew her sister's online secret. Despite her business degree scoring her a job that she didn't feel the need to hide her face from, Sierra's online success as a masked domme sometimes surpassed her 9 to 5 paycheck. She never made her identity known, and mostly made solo content with the occasional guest star during her supposed "business trips" away from her two kids; Shaun and Stella. Even with these infrequent "business trips" to go dominate a high-paying sub and reap all the earnings from the content she created,,Sierra always kept her true identity hidden behind the veil of a black eye mask.Usually the men who paid for her keyholding services were regulars who paid for a chat with her fairly frequently. Far less frequently would she receive a thousand-dollar request for her keyholding services out of the blue like what happened with her son, but it happened often enough that she didn't bat an eye.

Shaun created a fake email address that he only used for his pornographic hobbies to reach out to (unbeknownst to him) his mother, Sierra; the masked domme. Upon finding out her P.O. box was in his hometown, he hoped to grab this mysterious domme's attention with the fact that he was a local in her area. Sierra never paid any mind to the sender so long as they agreed to her terms of service and paid her the money, which Shaun had done. And even if she did take note of the sender, it's not like Shaun used his real name when contacting (unbeknownst to him) his own mother to be his keyholder.

As SIerra's laughter subsided alongside her sister's over the phone, Summer chimed back in to prove her point: "See? You gotta admit, it's honestly hilarious! Poor Shaun goes looking to fulfill some kinky fantasy of his only to have the keys to his little chastity cage land in own mother's possession. And he doesn't even know! That's the best part! You've got a golden opportunity in your hands right now sis! Do you even realize that?"

"Oh?" Sierra's attention perked up at her sister's point. "You think so?"

"Absolutely!" Summer insisted. "Think about it, you've told me Shaun's had no direction since he graduated high school. Poor thing fresh into adulthood without a plan for his future. And given how much time he's spent mowing lawns for all the wrong reasons, it sounds like he didn't really have his focus in the right place. Does he still not have a job yet?"

Sierra scoffed at her sister's question, "No. I can hardly get him to tidy up the place while I'm at work. He just sits on his ass all day doing who-knows-what."

"Well I know one thing you don't have to worry about him wasting time on anymore," Summer chuckled.

Sierra let out a laugh in return, and felt a sense of comfort at the point her sister made.

"Does his little online girlfriend know?" Summer asked.

"I don't know!" Sierra blurted out as if it were obvious. "How am I supposed to know?!"

Summer didn't miss a beat when she moved on: "You should tell him."

Sierra went quiet. This has been the dilemma she's been grappling with all day. "Do you think I should give him the keys back? And the money?"

"Hello no girl!" Summer said defiantly. "Those are yours now! He wanted you to have them!"

"Well..." SIerra felt the need to point out. "He wanted an online domme to have them... not his mother..." She struggled to hold back her chuckles.

"So?" Summer said with a shrug in her tone. "That's on him. He shouldn't go locking his pecker into cages and sending the keys to women he doesn't even know online. If anything, he should feel lucky that of all people who could've gotten those keys from him, his own mother's the one keeping them safe and sound and out of his hands, keeping my little nephew from shutting himself in his bedroom all day jerking his little boyhood."

"Summer!" Sierra said with a laugh and disgust.

"What?! It's true!" Summer pointed out. "He can't masturbate anymore unless his own mother is generous enough to give the keys to his cock cage back to him! You know how quickly he'll turn to putty in your hands sis! And with that piece of shit abusive father of theirs out of the picture, you need a man to pamper you the way he shouldn've. Better that Shaun turns to putty in your hands than some online domme. Am I wrong?"

Sierra seriously considered her sister's points. She didn't disagree with any of it. And she didn't see many downsides to keeping her son's chastity keys in her possession other than his own discomfort. The only decision she struggled to make was, "You really think I should tell him I have them?"

"100%!" Summer insisted. "He made his decision to give up that freedom. You're under no obligation to give them back. Take the money. Take the keys. Mold your son into the perfect little obedient angel you've always wanted."

Summer's point about Sierra gaining something she's "always wanted" really resonated with her. After years of being an online domme, the thrill of ordering a man around to do her bidding swelled up into a desire; a goal in life. These infrequent "business trips" she took to dominate some high-paying sucker became an ever growing fantasy she'd always wanted to bring home with her to wait on Sierra hand and foot in her own abode.

The front door opened, catching Sierra's attention. She knew it was her son returning home from seeing a movie with a longtime friend of his. The walls between the kitchen and the foyer were open enough for her to hush her tone to let her sister know, "He's home!" almost giddy in her tone.

"Keep me posted sis," Summer replied. "Tell me all about it asap!"

The call ended and Shaun entered the kitchen to greet his mother.

"Hey mom," Shaun said with a forced smile, adjusting his crotch for reasons his mother was completely aware of.

Part of Sierra hesitated. Was she really about to do this? "Hi honey!" Sierra said with an unsure quiver.

Shaun noticed his mother's awkward mood right away. He thought she might've just gotten off a phone call bringing bad news. "All good mom?"

Her son's simple question stirred Sierra's mind to consider, was she "all good?" Regardless, she realized she held the power for things to be better for her in the palm of her hand. That's when she realized, she was holding back; trying to silence the dominant beast of a woman inside of her always wanted the reins of her being. Sierra felt her inhibitions unhinge, as if the keys she fidgeted with in her hand unlocked more than her son's ability to ever masturbate again.

The scrape of the two keys in her hand caught Shaun's attention. Given his situation in being truly cock-locked for the first time in his life, the sound of keys at any decibel made his heart sink. "What... What's that?"

A slow half-wide smirk stretched across Sierra's face as she gazed at the two little keys in her hand that gave her so much power. "What?" Sierra asked her son rhetorically.With pride in her pinch, Sierra dangled the two keys to her son's cock cage up for him to see. "These?"

With how recently Shaun had sent the keys to his cock cage to the masked online domme he fancied, seeing a set of two small familiar looking keys dangle in his mother's grip absolutely mortified him. The dots connected at light speed. His disbelief stirred him to jump right into asking: "Why...Why do you have those?"

"Do you know what these keys are for son?" Sierra asked, letting her smile relax to stretch further across her face, flashing her white teeth so proudly.

Shaun gulped and trembled at the thought. He felt like he was lying to himself when he tried to brush away the possibility that those were indeed the keys to his chastity device in his mother's grip. "I... I..."

Sierra decided to have some fun with her son's discomfort. "I got them in the mail today," Sierra explained as she swung the keys back into her palm and studied them up and down. "And I have a hunch as to what these two little keys go to..." Sierra let the tension simmer before asking, "Why?" and holding the keys up to her son's face from across the kitchen island. "Are they yours?"

Shaun was almost too afraid to answer, "Y-Yea-"

"Oh?!" Sierra cut her son off. "These are your keys now, are they? Huh... That's funny..." Sierra took out her phone and began tapping about to find something. "Because I'm pretty sure that the person who sent mommy these keys agreed that..." Upon finding the terms of agreement Sierra makes her keyholding clients sign, she read aloud: "The client agrees to surrender all possession and ownership of said keys to the keyholder for them to do with as they please and see fit."

"What are you reading?!" Shaun asked, nearly shouting in horror and disbelief. "H-How did you get those?!"

Sierra looped her thumb into the ring to let her son's chastity keys dangle as she brought her flat hand up to her eyes and spread two fingers apart to peek through at her son and show him the identity of the woman he'd just sent the keys to his chastity cage to, and whom he'd been masturbating to all this time for years and years and years. "Surprise!" Sierra said almost playfully, as if she felt her son should be excited as she slowly sauntered around the kitchen island.

"No... No no no..." Shaun muttered as he backed away from his mother.

"Now, I have to admit," Sierra said as she herded her son's back to the kitchen table, stopping his nearly paralyzed escape. "Mommy's rather disappointed that her little boy would even consider sending the keys to his little dicklet to some strange mysterious woman on the internet he's never even spoken to." Sierra leaned her body into her son's and felt the hard plastic bump of his cock cage against her thigh. "You should feel lucky that that woman was your mother!"

Shaun was sniffling back tears of shame and utter humiliation. "M-Mom... I'm... I'm s-so sorry! I... I don't know what I was thinking!"

"Really?" Sierra scoffed as she leaned in closer, intentionally pressing on her son's cock cage and slowly stabbing a glare into him as she dangled the keys over his head. "Because mommy knows exactly what you were thinking..." Sierra then raised herself upright, still keeping a firm knee on her son's caged up libido as she brought her hand to her son's cheek to aggressively cradle it as the keys dangled from one of her fingers. "You clearly were looking for a woman to take control of you... to make decisions for you... And as a poor horny young man, you knew - like all the rest - that the way to a man's obedience and through his libido. All this time, mommy wondered why you lacked any ambition in life, and now I see why... You just want to live under the thumb of a powerful woman for the rest of your life. Don't you son?"

"N-No mom..." Shaun honestly didn't lie; the truth coming out once his fate felt cornered.

"No?" Sierra scolded gently as she grabbed a tuft of her son's hair with one hand and took out her phone with the other to dig up more unfortunate dirt that her son provided her. "But that's what you told mommy in your email," Sierra said as she turned the phone to show her son the exact email he'd sent to his mother's dominant online masked persona.

And there it was, word for word, in an email Shaun typed up himself and sent to - of all people, unbeknownst to him - his own mother: "I just want to live under the thumb of a powerful woman like you for the rest of my life, goddess."

Shaun tried to lie his way out of this; "That... That wasn't me!"

"No?" Sierra questioned as she welcomed herself to her petrified son's pockets to pull out his phone. She held the locked screen up to her son's face and demanded that he, "Unlock it if you ever want to get these keys back from mommy now."

To which Shaun obliged, only digging his guilty hole deeper confirming how desperate he was for the keys his mother dangled before him.

Sierra hummed as she tapped about her son's phone to find, "Aha!" the exact account Shaun used to email the woman he thought was just some masked online domme, and not his own mother. "So, you were maid-boy-420@gmail.com, huh? Wow... who woulda thought... My own son wants to be mommy's prissy little sissy French maid," Sierra teased. "You want mommy to dress you up in a frilly little emasculating skirt with petticoats and frilly aprons and dainty headpieces like I make all the other boys online do for me? Hm?"

"P-Please mom..." Shaun literally begged. "No... No I don't want that... Please!"

"Well..." Sierra then pulled her son up to her eye level by his shirt collar. "You just be a good little boy for mommy and maybe I won't make you into my own little live-in French maid."

"P-Please mom..." Shaun begged. "You- You can't do this to me!"

"Oh I most certainly can young man," Sierra explained. "It's all in the terms of service you agreed to when you signed up to have your own mother decide on when and if you get to masturbate ever again."

"Mom please..." Shaun begged, letting the tears loose in his eyes.

Sierra then let go of her son, sending him to his knees on the floor before her.

Shaun cupped his hands to beg to his mother from the floor. "Please mom... I- I made a huge mistake! I can't... I don't want to be a French maid mom... What- What if Stella sees me?! She'll tell everybody we know! Almost everybody we went to school with goes to Stella's university mom! Please! I'll do anything! Just don't make me dress up as a maid... Please... Please don't tell anybody about this..."

"Well..." Sierra shrugged, almost indifferent to her son's embarrassment. "I already told your aunt Summer."

"What?! Aunt- Aunt Summer?!" Shaun cried out, humiliated.

"Oh lighten up son," Sierra shrugged. "She's the only other person who knows about my online domming. I just had to tell her whose little chastity keys to somebody's poor widdle locked up boyhood I just got my hands on," she laughed. "Boy, you should've heard how hard she was laughing when I told her. She had to mute the phone!" Sierra chuckled. "I mean, it is rather humorous if you think about it. A young man fresh out of high school, ready to take on the world, ready to mingle with the single ladies and find a nice woman to settle down with... can't even so much as have an erection without having to come to mommy and ask her if she'll let him," she laughed.

"Mom..." Shaun cried as he hugged his mother's shins in desperation. "This is so humiliating... Please... Just please don't tell anybody else about this... I'll... I'll do anything... Anything!"

"Does that little online girlfriend of yours know?" Sierra asked.

With shame in his tone, Shaun answered, "No..."

"Tsk tsk tsk..." Sierra clicked in a gentle scold. "What a shame... Poor girl doesn't even know that her boyfriend on the other side of the country has his pecker all locked up by his own mommy," she cackled. "Sure would be a shame if she found out."

"Please mom!" Shaun begged some more, lowering himself to his mother's open-toed high heeled feet. "Please don't tell Melody! Please! I don't want anybody else finding out about this! This is so so humiliating mom! I'm sorry!"

Sierra let her son beg for a bit as she stood there above him reveling in the power she held over him, kneeling before her so helpless and desperate. "Alright," she decided. "Mommy won't tell anybody that you sent her the keys to your chastity cage."

"Thank you..." Shaun wept. "Thank you..."

"But you aren't getting them back anytime soon," Sierra explained.

"What?" Shaun whimpered, more so to himself. He truly thought his mother was toying with him to teach him a lesson. That this would all be over after he expressed his deepest regrets. Little did he know she plans she had in store for him.

"You heard me," Sierra explained. "Mommy's going to keep the keys to your chastity cage for as long as I see fit. So if you ever want to get out of that thing to touch yourself again, you have to come to mommy and ask if I'll let you masturbate."

The sheer thought of humbling himself to such a degree before his own mother turned Shaun pale and nearly froze his once trembling body. "But..."

"That's when I'll know that I finally instilled a sweet sense of humility in my little boy," Sierra said with pursed lips as she pet his cheek at the floor with the inner-side of her high-heeled foot. "When he's finally been brought to a point of desperation that he needs to cum bad enough that he'd actually be willing to cross that ever so emasculating bridge and go ask his dear sweet mother if she'll be generous enough to let him have a little cummie. Y'know, unlike other boys your age who have the freedom to shut themselves up in their bedrooms and stroke stroke stroke to their heart's content without their mother's knowing. Oh you poor thing... The day mommy finally lets you touch yourself won't even come with the luxury of privacy! No, you'll have to hurry up to your room with your untouched cock finally getting to stretch to an erection for the first time in who-knows-how-long and stroke your little boyhood knowing that your mother is completely aware of what you're doing in there. Touching yourself. Masturbating. Knowing that outside of that bedroom door of yours, your own mother has you on her mind knowing all about what you're doing in the so-called privacy of your bedroom. Gosh... That must be so humiliating for you, isn't it son?"

Shaun didn't even have the capacity to answer.

"Tell me son... What was the last thing you masturbated to? Hm? Was it one of mommy's videos of me bossing boys like you around?" Sierra asked rhetorically with a cackle.

Shaun felt sick to his stomach realizing she was absolutely right.

"Oh that's rich!" Sierra laughed. "My own son creeping online and watching his own mother's content to masturbate to! And you didn't even know it! Ha! That's the best part about it! That you didn't even know it was me you were jerking off to all this time! Oh you poor thing... Hopefully I didn't end up losing myself a subscriber over all this," she chuckled. "Maybe you will end up going back to jerking that little dicklet of yours to mommy's videos again next time I let you out. Maybe you'll get so used to having to ask your mother for permission before you can masturbate that I'll be the only woman you can get off to!"