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Emily's Spanking and Chastity Stories

Erotic writer, focusing on transgender chastity, spankings, and all-around hot sexy things. I do commissions, and I'm always looking for new writing prompts. Feel free to reach out.

Maid for Service: Part 3


               Clara was clearly upset. She didn’t scream or yell or carry on, but Emily had learned to read her body language over these past weeks living with her. Her movements were a little too stiff, her voice a little too firm, her back a little too straight and her smile far too brittle. She was furious and Emily felt awful.

                “Emily; you will clean this mess up and then join us in the living room. Amy, please fetch Kim a fresh glass of wine and then I would like you to fetch my favourite implements from my room. A paddle, a strap, and a cane. You know the ones I want.”

                Emily felt the hot tears begin to well in the corners of her eyes and then roll down her cheeks as she quietly began to mop up the spilled wine with a paper towel. The evening had been going so well and she had ruined it. She was so useless! She deserved whatever she was going to get in a few minutes, and she vowed not to cause too much of a fuss. She was mad at herself and a little self-pitying to be sure, but more than anything she was devastated at letting down Amy and Clara. She finished mopping up the last of the liquid and threw the sodden paper towels into the bin.

                Carefully, she swept up the tiny shards of glass from the floor, trying to balance being thorough in getting all of the tiny sharp slivers off the ground with being quick enough that she couldn’t be accused of trying to drag it out to delay her punishment. Dumping the broken glass into the garbage with a tinkling rattle she smoothed her uniform as she took a last scan around the dining room. Satisfied that there were no errant shards of glass or droplets of wine she wiped the worst of the tears from her eyes, took a deep and shaky breath and walked into the living room.

                On first glance, she might not have thought anything was wrong. Kim sat on one side of the sofa, legs crossed comfortably with Amy kneeling at her feet blotting the wine stains from the legs of her jeans with a white cloth. Clara was perched on the arm of the other end of the sofa, glass in her hand chatting and laughing amiably with both Kim and Amy. If it weren’t for the array of painful looking spanking tools laid out neatly on the seat of the couch between Kim and Clara it would seem perfectly innocent. Clara’s eyes followed her into the room as she entered; she would be beginning Emily’s punishment soon, but there was something very important that Emily wanted to do first.

                Crossing the living room floor quickly, she sank to her knees, and hung her head. Clara and Kim’s conversation died out as Emily looked down at her bare knees pressed into the pile of the carpet.

                “I’m really sorry for ruining the dinner party, Clara. It really was an accident. Amy I know how hard you worked and how incredibly important it was to you that everything go smoothly. I’m so sorry for everything… I’ll take whatever punishment you feel I need, I just don’t want to feel like this anymore…”

                She could feel the tears starting again, and she felt a twinge of guilt at ruining the makeup that Amy had helped her with this morning. She could feel everyone’s eyes on her and she was sure she was going to be scolded harshly. She dug her fingernails into the palm of her hand, waiting for the stinging words she knew were coming.

                Instead, she felt a hand gently resting on her shoulder. She looked up to see Clara standing over her, a small smile on her face.

                “Apology accepted, Em. I know you didn’t do it on purpose, and if anything I am incredibly proud of how well you worked with Amy; everything was nearly flawless tonight. One broken glass doesn’t change all that.”

                Clara helped Emily to her feet and wrapped her up tight in a hug. She was almost the same height and weight as Emily, but she was surprisingly strong for her size. When she let her go, she had a mischievous smile on her face;

                “Apology accepted, but not entirely forgiven just yet; I think this could be an excellent teachable moment for you, and for Kim.” She turned to Kim, who was still seated on the sofa. “You’ve never really spanked anyone before, have you?”

                Kim blushed and laughed. “A couple times, at play parties, but never as a punishment, no.”

                “A first time for everything then!” Clara replied; her body language changing from gracious host to the controlling Mistress Emily and Amy knew so well. “As a first lesson; you can’t paddle a girl with a plugged bottom. If you hit the pug, you could cause real harm. Amy, would you please go and get Emily ready?”

                Amy rose quickly and took Emily’s hand, briskly walking her out of the living room, down the hall into the bathroom. Emily followed mutely, surprised by how quickly the evening had changed.

                “Take the plug out, and use the bathroom if you need to, I’ll be right back.” Amy said with a wink.

                Emily eased the plug out of her bottom, and washed it in the sink. She considered using the toilet, but she was too nervous to need to go. As she waited for Amy to come back she tore off a square of toilet paper and tried to fix her eye makeup in the mirror. She knew that very soon her tears would make this a futile exercise, but she wanted to look her best for Clara, and especially Kim.

                Amy was back in a twinkling, her face flushed; she must have run down to the room they shared in the basement, and all the way back up. She was holding a pair of Emily’s simple white panties in her hand. Laying the clean cotton garment aside, Amy stepped in close to Emily and gave her a quick peck on the tip of her nose. Emily blushed, easily flustered by Amy as always, and Amy took the toilet paper from her fingers and continued the job Emily had begun in fixing her makeup.

                “They probably won’t let you keep them up, but if Kim’s supposed to be learning, you may as well make her work for it!”

                Amy’s eyes were full of laughter and between that and the flush in her cheeks, Emily couldn’t resist. She wrapped her hand around Amy’s waist and pulled her in for a deep kiss. Emily was almost never the aggressive one, but her tongue probed deep past Amy’s lips, and after a moment’s shock Amy leaned into it and reciprocated. Emily felt her cage tighten as she slid her hand down, below the hem of Amy’s skirt and gripped her ample bottom.

                Amy was the one to break the kiss, though it lasted nearly five full delicious seconds; but she didn’t try to take Emily’s hand off her posterior.

                “Well that’s something we’ll have to explore later. There’s a whole side to you I didn’t know about before.”

                She looked like she was about to say something else, but instead she scooped up the panties off the counter next to the bathroom sink, and held them out to Emily.

                “Put these on, and we’d better get back before we’re both in trouble.”

                Walking back into the living room, they saw that Kim had moved from the sofa to a straight-backed, armless wooden chair. Both girls stomachs twisted a little seeing it – only Clara sat in that chair, and only ever for one reason. Kim sat up straight and uncrossed her legs as Emily approached; her face serious. Emily was nervously trembling as she laid over Kim’s lap, and she was surprised to find that Kim was doing the same; while this was a very familiar position for Emily it seemed to be a new one for Kim.

As she made herself comfortable, Kim slid the hem of her skirt up her back, and she heard Clara’s suppressed giggle at the sight of her panties. She expected she’d be hearing about that later, Amy likely would too…  She felt Kim’s hand begin gently stroking her bottom, warm and gentle through the thin fabric pulled tightly across her vulnerable cheeks; and Emily looked back with a smile of relief and gratitude. Kim returned her smile, both young women trusting the other and sharing a sense of nervous anticipation. Emily knew what was expected of her:

                “I’m sorry again, everyone. I didn’t mean to drop the glass. Kim, will you please help me remember not to do it again?”

                Kim began with a few hesitant and half-hearted swats with her open palm against Emily’s bottom. It didn’t really hurt, but Emily was extremely aware of all three pairs of eyes watching her. After about a dozen nearly inconsequential swats Clara stopped Kim; crouching down near Emily’s face, her voice was light and conversational.

                “That’s a good start, Kim dear. Now Emily; will you please tell Kim exactly how that felt?”

                Emily was a little taken aback. At home or at school her contributions to the conversation while she was over the knee tended to be limited to apologies, promises to never do it again, and then inevitably her begging for the spanking to end. Her skills as a conversationalist were… underutilized. To have Clara sitting on her haunches, inches away, ready to take hold of her wrists in time to prevent her reaching back, and making her an active participant in her own punishment was entirely new.

                “Er… It was…” Emily looked up, and saw the kindness and trust in Clara’s eyes. She couldn’t lie. Not to Clara. Telling the truth would hurt, but lying to Clara would be worse. “It was really light, even a warmup from my parents would be much harder.” Emily admitted. “I get spanked… a lot at home… and at school. You can spank quite a bit harder than that and I’ll be okay.”

                Clara reached out and gave her wrist a gentle squeeze. “Amy? Your thoughts?”

                Emily could hear Amy from over her shoulder; she must have been standing behind the chair, off likely off of Kim’s right shoulder where she doubtless had an excellent view. “Oh most definitely too light; I’ve seen her take a lot more than that… hard to tell if she’s getting pink at all with those panties in the way, too.”

                Emily saw the grin twist Clara’s lips as she looked up at Amy;

                “Yes… I wonder where she got those… but they can stay for now. I think another set for our naughty young lady, Kim.”

                The next dozen from Kim’s hand definitely stung, and the sound of her firm palm impacting Emily’s vulnerable bottom filled the living room as she received her second set.

                “Em? How was that?” Clara enquired.

                “I definitely felt that…” Emily conceded, and she twisted around slightly so she could see Kim’s face. “But I can still take it quite a bit harder than that. You won’t really hurt me with just your hand, Miss, my father’s a LOT stronger, and he’s never done me any real harm.”

                The next dozen was nearly as hard as what Emily’s parents would consider a warning: A sharp, stinging dozen over her panties for coming home a couple minutes past curfew or when they knew she had been procrastinating. A warning of a much worse punishment to come if she didn’t pick up her feet. The next dozen were harder yet, nearly on par with her mother’s hand.

                “My palm is tingling, Clara. I think Emily’s butt is tougher than my hand…” Kim laughed, her nervousness clearly fading... She was definitely enjoying this, but the palm of her hand was already pinker than the slight pinkness of Emily’s chubby bottom where it peeked out from her panties.

                “How was it for you, Em?” Amy had gone from passive spectator to active cheerleader and had taken the lead on this to a degree that Emily found a little surprising. Clara simply hung back and watched, sipping her drink and giving Kim gentle suggestions on her technique. To enjoy seeing someone else getting spanked instead of it happening to you was a sort of voyeurism that Emily fully understood, and the combination of Amy’s open delight, Clara’s gentle encouragement, and the gentle strokes of Kim’s hand between each set was making her leak into her panties.

                “That’s about as hard as my mother spanks me… with her hand. She uh…” Emily hated herself for admitting this “…she also gets a sore hand and switches to something else after a little while.”

                “Oh?” Clara was watching with delight from her perch on the end of the couch, her hand was resting in her lap, and Emily wondered if she was sneaking in a subtle touch now and then while she watched.  “What sorts of things?” Clara nodded to the small array of implements laid out on the couch next to her.

                “Err… well not the strap or the cane, not while I’m over her lap like this at least. My mom has a couple of paddles she uses, and the spoon; and my dad generally only uses his hand or his belt….” She hesitated for a moment, cleared her throat and then continued more quietly “At school, the Headmaster uses a hairbrush…” She had only felt it the once, but it had been one of the most painful experiences of her entire life. “…and I guess I get the brush pretty often at home too.”

                “Ah…” Clara smiled. “Amy is very familiar with the feeling of a brush against her little bottom. Small, simple, and viciously effective little things. For years I had Amy keep one in her purse in case she needed a little bit of an attitude adjustment while we were out of the house. Do we still have that one, Amy?”

                Amy flushed a little and nodded. “I… still use it for my hair, actually. Should I go and fetch it then?” Clara nodded and Amy scampered downstairs to retrieve the brush for her mistress.

                “Now then, while we wait, why don’t you give the leather paddle a try, Kim? It’s quite different from the hairbrush, but it will be good practice for you. I think the panties need to go, as well; you can’t really do that much harm with just your hand, but with the paddle you need to be able to see the effect you’re having.”

                As she had done countless times before for her parents, teachers, the Headmaster, and Clara; Emily lifted her hips up off of Kim’s lap, and allowed her to slide the thin protection of her panties down; leaving her whole bottom and her bright red cage exposed.

                Under Clara’s careful tutelage Kim laid down two dozen stinging swats with the leather paddle on Emily’s rapidly reddening posterior while she yelped and squirmed and when called upon, tried her best to give Kim helpful advice. Amy watched gleefully upon her return, turning the brush over in her hands and, Emily spotted ruefully, dripping out of her own cage as she enjoyed the view.

                Laying down the thick leather paddle, Kim rubbed Emily’s tender bottom as Clara gave her instructions on the correct use of the brush; her fingers were gentle and teasing as she soothed Emily’s inflamed skin. She stoked across her cheeks, then down into the cleft between them; whispering her fingers dangerously close to Emily’s little hole, then further down, skimming the metal ring of Emily’s cage.

Distantly, Emily she knew she must be making a terribly sticky mess of Kim’s jeans, but she didn’t care. She was sore, and the brush was going to make her a great deal sorer very shortly, but every time Kim’s hand moved over her skin she shivered in delight, and when she gave a little whimper Kim would reward her by gently tracing a fingertip over her hole. Emily looked back and showed her gratitude to Kim with a wide smile. Her bottom stung, certainly, but she was still having more fun than she would ever admit.

                “Now the hairbrush is a deceptive little implement. It seems so harmless, but with very little effort…” CRACK! Clara slapped the back of the brush into her own palm, and held out her hand to show Kim the rapidly reddening and inflamed flesh. “It can do a lot of damage. This is the first implement that you could really hurt Emily with, so be careful, let the weight of the brush do most of the work, and listen to what Emily tells you between sets.”

                Emily promised herself that she was going to be brave and not reach back as Kim tentatively tapped the cool wood of the brush against her sit spots; getting a feel for the weight of the implement. The first dozen weren’t too bad. Emily squeezed her eyes shut, gritted her teeth and pushed her hips deep into Kim’s lap but managed to keep herself from kicking or squealing. As soon as it was over, she felt Kim’s hand gentle stroking the small of her back.

                “A bit of a step up from the paddle, I see?” Clara had taken the lead again, and Emily looked up into her scrutinizing blue eyes.

                “I… I can take it a bit harder, Miss. Honestly, my parents always insist on a spanking lasting until I’m crying, so it’s a mercy if you spank harder and get me there sooner. A spanking should hurt, and you can let me have it a little more if you feel up to it…”

                Clara beamed down at her, pleased with her honesty, and looking off to her left she could see Amy smiling down at her as well. Despite the soreness in her bottom she tried to smile back in what she hoped was a brave manner.

                “Try giving the brush a little more of a snap with your wrist, Kim;” Clara suggested, demonstrating the technique with her own well-practiced arm. You’re using too much of your shoulder and not enough of your elbow and your wrist. The brush is surprisingly heavy and will do a lot more of the work for you if you flick it down with a snap.”

                It took 3 dozen more spanks with the brush before Kim managed the level of nearly effortless pain delivery that Clara was looking for. Emily was red in the face with tears just beginning to flow by the time it was over; her feet drumming against the floor as the pain built but she managed to keep from reaching back.

                “That set felt just about right, Miss. That’s the way I get it at home or at school: It hurts from the very start and the pain just builds over time, getting worse and worse until I can’t take it.”

                Kim rubbed her back gently between her shoulders, helping Emily relax and stay settled over her lap; “It feels like I’m barely doing anything at all!” she marveled “It really is just a flick of the wrist, and Emily is squirming after just the second or third swat.”

                Clara laughed “I’m sure it feels like more than just a flick of the wrist to poor Emily, but then she has this coming. She has been extremely cooperative with all of this, but I’m afraid for her that the next lesson is going to be a lot less fun for her. You need to learn how to manage a squirming, kicking submissive over your lap, and for that we are going to need to put our clumsy little friend into a great deal more discomfort.”

Clara left the sofa and knelt next to Emily’s face once more, cupping her chin in her hand; “Emily, I know you’ve been trying very hard to take your medicine like a good girl, but for this next part to work, I want you to imagine it’s someone else spanking you. I want you to kick and squirm and all the rest like you normally would. Kim, I want you to give Emily ten dozen good hard spanks with the brush without stopping. She can take it, and I’ll stop you if it’s more than she can handle; but you need to learn to manage a girl who is trying to interrupt a spanking.”

                Emily braced herself as Amy took up her usual position kneeling near her shoulders, ready to take hold of her wrists so she couldn’t reach her arm behind her to protect her bottom.

                “No, Amy. If Emily reaches back, Kim needs to deal with it herself; she won’t always have your help.” Clara was firm and clear, and she was taking this very seriously.

                Kim gave Emily’s bottom a final two gentle strokes with her hand before raising up the hairbrush and bringing it down with a WHAP!

                Despite Clara’s instructions Emily tried to keep it together; to not kick and squirm, but it was impossible. Clara was an excellent teacher and Kim had gone from rank amateur to delivering the sort of spanking Emily’s father would be proud of in a remarkably short amount of time. The pain went from burning to intolerable remarkably quickly, and before she had gotten the second dozen she had already kicked off her shoes.

                As her kicking worsened Clara instructed Kim “Spank the backs of her thighs until she stops kicking, and then move back to her bottom.”

                The sharp pain of the brush against the previously snowy whiteness of her thighs brought forth the first real sob from Emily all night and he did her best to still her feet; wrapping one ankle around the other and willing herself to stop kicking. Mercifully, a few seconds later the brush went back to pummelling her bottom and left her thighs alone for now.

                By the end of the fourth dozen, Emily was swinging her hips side to side and beginning the long form whining apology that she always lapsed into when she was being spanked.

                “I’m so sorryyyy! I promise I won’t do it… OW!... I won’t do it agaaaaaain! Just stoooop! I’ll be good, I’ll be good! I’ll be Goooooood!!!”

                Clara cleared her throat to get Kim’s attention. “This is an excellent time for some scolding. You have the girl’s full attention, and focusing on answering the questions will mean she isn’t focused on squirming away from you. Observe:”

                Clara leaned down so her face was close to Emily’s; “Are you sorry for what you did?”    

                Emily’s squirming subsided noticeably despite Kim not breaking the rhythm of bringing the brush snapping down into her scalded behind. “Yes Ma’am!” Emily wailed.

                “What exactly are you sorry for?”

                “For… OWIE! For ruining the dinner party, and breaking the glass, and getting wine everywhere, and letting Amy down and…. AAAAAHHHHH”

                “That’s a good enough answer, dear. Are we going to have to repeat this lesson?”

                “No… No! Never Ma’am…” Emily was sobbing her answers now, the pain in her bottom was reaching a crescendo and she was gripping the legs of the chair so tightly her knuckles were turning white.

                “You see? Highly effective and it confirms that you’re getting your point across. Any backsass now, any hesitation in offering a total apology and you need to add extras. But this helps reinforce the lesson, and ensure that the girl understands why she’s here. You try it now.”

                Kim looked a little stumped for a moment, but she didn’t break her rhythm.

                “Are you learning your lesson, Emily?” she began, lamely.

                “Yes Ma’am…. <SOB> I am so sorryyyyy!”

                “Is the hairbrush getting through to you?”

                “Oh! Oooooh! Owie! Yes! OW! Please just stoooooop!” Emily was having trouble talking now, and despite the scolding she was squirming to the point that Kim was having trouble controlling her.

                “Do we need to repeat this lesson in the morning before I go?” she was beginning to get it now.

                “No, Ma’am! PLEASE!!! Anything but that!!! Just stoop… I can’t taaaaake… I can’t take it anymore…..”

                “Be ready, Kim. You’re nearly at the critical moment.” Clara was leaning in, waiting. She saw the muscles in Emily’s arm begin to move even before Emily herself was aware of the reflex; “Now! Pin her arm!”

                Emily had finally cracked and reached back. She still had a little more than two dozen more spanks to take but she had both lost count and her final bit of composure. She reached her arm back, knowing that it wouldn’t stop the spanking any longer than a moment, but even a moment’s reprieve from the horrid hairbrush was more than she could resist. Her bottom was in agony, her thighs stung, and she was a very sorry girl indeed.

                Amy gripped Emily’s wrist and tucked her arm into the small of her back. A creditable effort for a first try and even Clara was impressed.

                “Alright, that’s the moment. She’s all yours now. Give it a little more snap just to drive the lesson home.”

                The last two dozen burned like acid being poured onto her exposed skin and Emily kicked and thrashed and begged for mercy, but with her arm tucked into her back Kim was in total control. Finally, with one last resounding SMACK her punishment was over and Kim laid the brush down.

                Emily was too sore even for having her bottom rubbed, but Amy petted her back while she sobbed out the guilt and embarrassment and shame, her tears dropping from her scarlet face down onto the carpet. After a few moments her sobs turned to gentle hiccoughs and Kim gently rested her hand on Emily’s bottom, which was very warm to the touch.

                “There, there, you did very well. It’s all over now…” Kim soothed her. Looking up at Clara she wanted to make sure; “Right?”

                Clara stroked Emily’s hair comfortingly. “It is. All over. I had been planning to get Kim some experience with the strap and the cane, but that can wait for another time. You did very well, Emmy. All is forgiven.”

                After a moment, Amy helped Emily up off of Kim’s lap and wrapped her up in a hug. Then it was Clara’s turn, and finally Kim’s.

                “I… have to admit that was remarkably stimulating. I enjoyed that more than I thought I would…” Kim admitted a little red in the face from a combination of wine, exertion, and excitement.

                “Oh?” Clara smiled, wrapping her arm around Amy’s waist. “Amy had prepared a special dessert, but if you’d prefer I’m sure Emily would happily escort you back to your room and spend the rest of the night making it up to you…”

                It turned out Kim wasn’t terribly hungry for dessert in the end, and she took Emily and her bright red bottom straight to bed.

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