The Collaring of Chloe Ch. 21

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Chloe shares a little of herself with their sissy-maid.
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Part 21 of the 42 part series

Updated 06/12/2023
Created 03/18/2017
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The Collaring of Chloe

Chapter 21 - Wise Sissies and Quilt Burritos

**Characters and text are protected under copyright law

"Oh fuck, oh fuck, oh fuck!" Mittens wailed, her voice pitching higher with each repeat, approaching the point of a shrill shriek. Her back was arched so heavily that her torso had lifted up from the sofa, pawed hands clutching the side of the couch above her head so hard Chloe was worried she was about to hear the wooden frame crack. "Imma gonna CUM!!"

"She's about to cum." Chloe reported tauntingly, voice a little breathy from her vigorous work with the bright pink dildo she was rapidly abusing her sister submissive's vagina with. She grinned over at Shawn, dressed in his little maid's outfit, who was trying to keep his attention on applying furniture polish to an end-table, though the way his lace-gloved hand was gripping the rag, she was certain he was wanting to polish something else.

"OH MY GAWD!!" Mittens howled, body exploding into convulsions of climax. She bucked so hard that Chloe could barely keep her rhythm, but still managed to keep her speed, enjoying making Mittens orgasm in general and hoping to get several in a row from her. Making her do it in front of Shawn just made it more delicious, as he was already bright scarlet about the cheeks.

"I didn't say you could look!" Chloe playfully snapped at him, huffing through the words. "Keep your eyes on your work, sissy!" Shawn quickly looked away and back to where he'd been polishing open air for the last couple of seconds. "If you're hard, I'm going to spank you, pervert!" She added, trying to make her eyes flash threateningly, but was sure her goofy grin and the laugh in her voice gave away that she had all the menace of a stuffed mouse.

"Yes, ma'am." He said, cowering despite her lame attempt at being 'dominant'.

"Oh, FU-uh-uh-uh-CK!!" Mittens warbled, her orgasm still thundering through her, sounding almost like she was in despair, though Chloe knew much better. Mittens was a deeply emotive climaxer, usually verbalizing with all kinds of emotional reactions from hysterical laughter to outright weeping, but it was all just explosive pleasure. She grinned at the sight of Mittens' eyes crossing, tears streaming from the corners of them.

"Sissy!" She said suddenly, waving towards him. "Mop her face!"

Shawn looked at her with a note of real apprehension. He seemed almost afraid to get too close, as though he feared Mittens, as sexually lathered as she was, might grab him if he got near enough. When Chloe slowed her sawing motions to just an easy rocking and Mittens' back relaxed back to the sofa cushions, he finally chanced complying. Mittens giggled as he reached out from as far as he could to pat at her tear-drenched face.

"I bet...bet he's hard...as a rock." Mittens panted out, her grin so wide that all four of her pointy cat teeth were visible. "We should...make him...show us!"

"No sucking on the sissy." Chloe admonished, which made Shawn take a step back, eyes widening in terror. "Though if he is, we need to spank him." She looked at the sissy maid and raised an eyebrow. "Well?"

Shawn demurred instantly, shrinking away with a look of panic. "I-I-I...I need to go...um...vacuum..." He stuttered, quickly trying to make an escape.

"Nope!" Mittens burst out breathily, though it was accompanied by too much of a giggle to sound any more menacing than Chloe's own attempt to be intimidating. "Skirt up, sissy!" She vigorously waved a paw in an upwards motion at him to accentuate the 'command'.

With an audible swallow, Shawn timidly reached down to lift up his short skirt, revealing pink silk panties and a lacey black garter belt that held his stockings in place. As expected, his panties were only barely managing to contain the erection he'd formed. "I-I-I couldn't help it, ma'am."

"Well, that's a spanking anyways." Chloe said with a chuckle.

Shawn winced, but didn't argue. Of course, spanking Shawn was a tradition and the girls always loved finding an excuse for it. Chloe was pretty sure neither she nor Mittens were at all able to make them actually hurt, but he always acted as though they were excruciating. "Yes, ma'am." He whimpered. He began to turn and lean forward, preparing for them to swat his butt.

Mittens started to rise, but dropped suddenly back to the cushions, tongue lolling and eyes swimming. "Ooooo...I dizzy. Chloe, you brokeded me!" She whined, though a twinkle in her eye told that she loved it. "I needs a glass a water..." She rolled her eyes comically, cute pink tongue wiggling just below her lower lip.

"I'll get it!" Shawn quickly volunteered, looking hopeful.

Chloe eyed him with mock suspicion. "You just want to get out of your spanking."

"Ma'am needs water." He said in a dutiful tone. "You wouldn't want her to faint." He ventured hopefully. His eyes pleaded for escape, looking just as comical as Mittens.

"Get the water." Chloe relented. "But you're still getting punished!" She called after him as he practically ran from the room, causing both girls to collapse in giggles.

An hour later, Chloe sat waiting on the same couch, a long tee-shirt pulled over her mostly naked body, clad in only a garter belt and stockings of her own and a pair of silky arm-length gloves, other than her slave collar. She'd actually intentionally worn the exact same garter and stockings as Shawn had been wearing, just so she could playfully tease him about rooting through her underwear drawer like a pervert.

Shawn had blanched bright pink at that, a sign that the idea had been a good one, as it was the humiliation that he craved. Over the last several visits from him, she'd grown more comfortable and creative with playing tormenter, now feeling more secure that he was actually enjoying himself. Still, she couldn't fully overcome a wash of guilt by the time he'd finished and changed back into his normal clothes. Cuddling with him on the couch afterwards had become a sort of ritual for her now, usually getting permission to throw on something first so to make it more casual.

In a lot of ways, she felt she owed him a lot more than just some snuggling, with all she'd put him through over the last few weeks, but he'd never once been anything but polite and careful with her. No matter how much they might have titillated him and teased him through the day, he remained ever the gentlemen during their aftercare cuddles. She'd honestly thought about trying to encourage him to cop a feel, at least, or even just ask for a kiss. She would have happily put that kiss ANYWHERE he wanted.

Still, there was something kind of wonderful about his self-control and well-behaved manner. In some ways, he had come to feel almost like a big brother that she lovingly picked on sometimes. They'd actually formed so much of a bond that she'd noticed that Master and Mittens had begun letting her aftercare with him be just the two of them. Their own private thing.

Shawn entered, once again in a Henley pull-over and jeans, a deeply amused smile on his face. "You just had to get Mister Brooksend to come give me the spanking." He laughed. "That was so mean!" It was obvious that he'd loved it though, he seemed to be glowing.

"Master gives the best spankings." Chloe explained, shrugging as though that made perfect sense. "I have noodle arms."

Shawn gave another laugh as he dropped on the sofa with her and she immediately rearranged herself against him, arms snaking around his broad and chiseled torso. "It was a good move." He admitted.

"Just as long you enjoyed yourself." She said, something she had found herself repeating almost every week. "I don't—"

"I'll let you know if you ever go too far, Chloe." He interrupted, tousling her hair. "You've never even gotten close. I don't think you have it in you to do anything that would really cross a line. Mister Brooksend is a LOT more evil than you are and I've never had to use my safeword with him either. He actually made me put in a butt-plug once."

"Seriously?!?" Chloe goggled at him, actually a little shocked. "And you...?"

"Bent over and let Mittens insert it." He said, blushing at the admission, but grinning profusely. "One of the more interesting days, to be sure. I'm half afraid of him demanding it again, half wishing he would."

Without thinking about it, Chloe kissed him on the corner of the mouth. It seemed to catch him so off guard his face went blank and, for a terrible moment, Chloe though she'd actually managed to cross that line. However, a moment later, a bashful smile came across Shawn's face and he blushed.

"Sorry." Chloe said demurely, half hiding her face in his shoulder. "I just had-."

"It's okay." Shawn said pulling her a little closer against him and brushing his fingers through her hair. "Just surprised me. You've never kissed me before."

"If you'd rather I didn't..." Chloe began, fidgeting a little, feeling a little awkward and shy suddenly. "I mean, you are always so—"

Shawn cut her short by planting a firm kiss on the center of her forehead. "I just like to keep things simple." He said with a soft chuckle. "This is where I come to get my kink. If I get too intimate with you or Mittens, it...changes things. It's not because I don't find you both really attractive, I mean, obviously I do." He gave another chuckle, cocking an eyebrow.

"But having that with one of us makes it feel less embarrassing when you're being tormented." She finished for him, getting the idea pretty easily. It wasn't too far afield from her own recent feelings regarding her status as a slave. They both wanted this to be pure.

"Still, some cuddles and affection won't hurt anything." He added. "Just nothing more than that."

Chloe fixed him with a warm and understanding smile, feeling even more akin with him than ever before. It didn't make her feel any less like she wanted to show him a lot more attention than hugs and cuddles, but it made her feel more comfortable with it being only that. For a few moments, they sat there, snuggling and enjoying the feel of each other.

"Did you hear about the girl at the munch who challenged my standing as a slave?" The question seemed come out of nowhere, bubbling up out of Chloe like a toxic fume. She'd found herself being suddenly stricken by the thought of PinWheelSoul's comments and the emotions they'd stirred up at random moments for the last several days. She could be thinking about anything else and have them seem to suddenly emerge from nothing.

Though the event had led to her talk with Master and the two of them reaching a new milestone in their connection as owner and slave, she'd found herself growing ever angrier over the confrontation. Each time it came back to her, she felt a little more attacked by what the woman had said. A little more insulted by the suggestion she wasn't a real slave. And always guilty about not standing up for herself as a true slave.

"No. What happened?" Shawn asked, looking concerned.

"Master, Mittens, and myself took our new friend August to a munch." Chloe began, already picturing the foul woman's face, which seemed to get uglier every time she remembered it. "August is...um...kind of my new...um...we're fucking." She blurted bluntly, suddenly finding this point a little uncomfortable.

Ever since the little show she and Master had put on, August's relationship with Chloe had taken a turn to something definitely more intimate. She'd slept over that night and the two had stayed up late drinking tea and talking earnestly. Chloe had been too drained to do much more than cuddle and kiss when they finally retired to her bed. However, the next time August had come over to visit, less than a half hour had passed before August had her face buried between Chloe's thighs.

It had felt wonderful and scary all at once, finally taking that plunge. Still, Chloe couldn't decide what August actually was to her. She found herself unable to make herself call August a 'girlfriend' or even a 'lover', always feeling a strange sense of guilt whenever she tried use either word. However, it hadn't stopped her from diving head first into the sexual side of whatever they were to each other. August had been over multiple times since the munch and was even supposed to be coming by this evening.

"Anyway, we took her to this munch and August was asking questions." Chloe continued, trying to get back to her original point. "She asked what the difference between a slave and submissive was and this woman who goes by PinWheelSoul pipes up. She starts going on about how there isn't any sort of difference, getting more and more insulting as she goes. Before long, I began to really get the sense she was specifically attacking me."

The look on Shawn's face was hard to read, seeming as though he were trying to remember something, but also making effort to actively listen. When she didn't immediately continue, he asked. "Did you set her straight?"

Chloe gave a sigh, half-burying her face in his arm. "That's just it, I sort of did, but not the way I feel like I should have. I more answered August's question properly than tried to argue with PinWheel. Basically, told her what the answer...should be, I guess. That a slave-Master relationship is based on more of a sense of absolute trust, yadda, yadda."

"Which sounds like a good answer." Shawn said supportively.

She heaved a sigh, frowning a little. "Yes, but I didn't actually defend my real feelings and that bothers me. Like I said, it really felt like she was targeting me in particular for some reason. Like she was questioning MY role as a slave, not just dismissing the idea in general. It felt, I don't know, personal."

"And it got to you." Shawn surmised, petting her sympathetically.

Pulling away a little and turning to more fully look at him, Chloe's face tightened. "What she said didn't, not really. What really bothered me was that I didn't correct it from that personal level. I'm not just a typical lifestyle 'slave', I am a REAL slave. Master doesn't just 'technically' own me, I am literally his property to do with whatever he wants. I feel like I should have rubbed that in her face."

"Except you were worried she'd turn it around on you and make you look like a weirdo or something." He said it as a fact, which she knew was true. Even Master had said something similar. Had she pointed out her true station as a real slave, it would have given the witch exactly what she'd wanted.

"Yes, okay, that's true." Chloe conceded, giving a weary nod. "It still sold short my own commitment to being a slave. A REAL slave. The fact that I didn't establish myself as such because it might 'look bad' felt like I was betraying it. Like I was admitting that it was...wrong."

She sagged against him, feeling that same wash of self-disappointment and guilt that seemed to be constantly coming at her from too many directions lately. Master had given her a pass, but she'd still denied her own convictions just to save face. She couldn't fully reconcile that with herself.

"The fetish community is a pretty judgmental and opinioned place, Chloe." Shawn said, his voice brotherly. "It's kind of sadly ironic, considering that it's supposed to be a place where people can express themselves in ways that mainstream would judge harshly, but there it is. Padding that truth, especially while spreading a good message of how it would normally work, isn't a bad thing. You didn't 'betray' anything, just avoided drama."

Chloe frowned at him. Obviously, he didn't quite get it either. Nobody, really, seemed to fully understand why this bothered her so much. Master seemed to get the idea, but didn't seem to really understand. August had been completely lost on the subject, but generally supportive. And now Shawn seemed to shrug it away too.

"It just...bothers me." She said, finally putting her face back into his shoulder. "I came to Master a true slave, was prepared to give up everything for whoever it was that had bought me. It was important to me that this be more than just me declaring myself a 'slave' of whomever I was dating. I wanted it to be...well, like with your sissy-play. I wanted it to be pure. To be a true slavery. To have no say, no rights, completely at the mercy of whoever I'd been sold to."

She fiddled a moment with the hem of her shirt, feeling a little adrift emotionally. It had all seemed so...simple when she'd thought it up. Like an adventure. Now it seemed so much more complex, so much more sacred.

"Why?" Shawn's question caught her completely by surprise.

"Huh? Why what?" She blinked at him like she was coming out of a trance.

"Why is it so important that you are a 'real slave'?" There wasn't anything negative in his voice or expression. No sense of judgment, just compassion. He was asking to understand. "I mean, I get the point of wanting a fantasy to be as complete as possible, but why do you need it to be that complete?"

Chloe opened her mouth, feeling a little grateful for the chance to really explain it. Then she closed her mouth, feeling suddenly uncertain. For the first time, she realized that she actually didn't know why she wanted it so badly. Wasn't actually sure why it was so important to her. Why it felt so sacred. The lack of having a real answer left her dumbfounded.

She looked up at Shawn with a lost and helpless expression, her growing confusion at coming up so empty on her own motivations showing so plainly that it brought a deeply sympathetic look to his own features. He reached down and drew her up into a fully embracing hug, holding her tightly in his strong arms. In the next second, as she'd done with Master, Chloe broke into a fit of bitter sobbing, crying in his shoulder.

It didn't last very long, less than a minute, but the burst of tears seemed to release the tension in her. She gave his neck a soft, heartfelt kiss. "Thank you." She said softly into his ear, sniffling a little. "I guess I needed that."

He relaxed his hug, half-helping her settle back into place, but his posture with her was now much more tender and caring. He gave her face a gentle caress of compassion. "It's obvious that it DOES mean something very important to you, Chloe. And that it means something significant, period. I think you might should try to figure out the answer to that question. It might help you to understand your own needs better and help you come to peace with why what she said bothers you much."

Chloe looked up at him with her wet, slightly raw, eyes, seeming to really see him for the first time. He seemed almost angelic in demeanor, his expression showing nothing but kindness and sympathy. "You really are a great guy." She said, a warm smile blossoming on her face. "Even if you are a sissy." She added playfully after a moment, her smile turning into a broad grin.

The two broke into sincere laughter, falling over each other, less from the remark than just the need for it. To make matters even better, the sound of laughter seemed to summon Mittens from out of nowhere. She jumped on top of them both and instantly joined in the laughter, without even knowing what had been funny, but laughing with just as much sincerity as they were.

Though they sat for a while longer, now three, Chloe said nothing more about the previous subject, just enjoyed the company of her dear, brother-like, friend and her deeply beloved sister submissive. When Shawn finally took his leave, Mittens walked him out, then rejoined Chloe on the sofa.

"I love you." She said sweetly and suddenly, seemingly for no reason at all.

Chloe snuggled up against her and sighed contently. "I love you too." She brushed a lock of dark hair from the catgirl's face and kissed her, deeply, tenderly. A sudden urge to do more struck her heavily, born not from lust, but emotional need to express her love physically. However, she resisted the urge and just cuddled a little more into Mittens.

12