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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 2:


Emily opened her eyes and stretched out in the narrow bed. Pale morning light streamed through the window set high in the wall of the small bedroom she had shared with Amy these past few weeks. The alarm Clara had set to rouse the two young women had not yet gone off, but Emily knew it would only be a few minutes at most. She could hear Amy’s deep, rhythmic breathing in the silence of the small room; she almost never woke up before the alarm, leaving Emily these few moments alone to herself.

                She hated to admit it, but the collar service hadn’t been all bad. It had its bad moments, like when she had badly burned one of Clara’s blouses during her early attempts at ironing and Clara had burned her poor bottom with a vicious narrow leather strap in exchange; but she had to admit that it hadn’t been nearly as bad as she had feared. A small smile tugged at the corners of her mouth as she thought about how incredibly generous a lover Clara could be. Once she had mastered the basics of pleasing her new mistress with her fingers and tongue, Clara had been more than happy to return the favour; pressing a powerful vibe against the hard steel surrounding Emily’s sensitive nethers and teasing her until she creamed in her little cage, or letting Amy drain her prostate with the strap on while she licked Clara to orgasm after orgasm.

                Admittedly, that was as far as it went. There had been no sign of her key, and neither a promise nor a threat in regards to her cage from Clara. For her parents, it had been a useful lever when she had been willful or disobedient:

                “Emily Black you will stop that right now or you will be old and grey before you ever see that key again!

                She had heard a variation of that threat countless times from both parents, and while it had been admittedly very effective, it had also promised that there would someday be an unlocking. With Clara, for all her generosity, there had been no discussion about unlocking her at all and Emily wasn’t anywhere near brave enough to ask. As she had so many times before, she unconsciously slid her hand down her body and squeezed the unforgiving steel in her hand, vaguely remembering how the silken caress of skin against skin felt. She felt her body stir briefly at the memory, filling the already-tight cage before subsiding. She had been locked too long for her body to still strain much.

                The shrill beeping of the alarm broke her reverie and she heard Amy sleepily moan and fumble for the snooze button. Emily wasn’t particularly tired anymore; she was looking forward to her workout and her day. The warm downy haze of sleep fell away as her feet hit the cold floor and she padded over to the small chest of drawers and pulled out a sports bra and a pair of running shorts. As she laced up her sneakers she paused suddenly. This was it. It was Saturday! They were going to have company for dinner!

                “Hey! Wake up sleepyhead!”

                Emily pulled the pillow out from under Amy’s still-drowsing head. Amy moaned and waved her arm out, grasping, feeling for the pillow without opening her eyes. Emily leaned in and gave her a quick kiss on the top of her forehead, dodging her outstretched arm.

                “C’mon! Let’s get going! We have company tonight!”

                Emily didn’t wait for a response as she jogged across the hallway to the home gym that took up most of the basement. Along with the small bedroom she shared with Amy, and the near-identically sized bathroom that doubled as a laundry room, the entire basement was given over to a well-appointed home gym. Punching her regular routine into the treadmill and putting her earbuds in, Emily tried to picture the night ahead:

                According to Amy, Kim was one of Clara’s best friends, if not her very best friend. Unfortunately, work had forced Kim to move to a different city about a year before, but she came to visit every few months. She was younger than Amy and Clara, who were closing in on 30, but at 22 she was only a couple years older than Emily herself; and according to Amy’s breathless descriptions, she was incredibly attractive.

Unquestionably a Domme, she was someone that Clara had taken under her wing as a student of the disciplinary arts at a play party, but that relationship had blossomed into one of deep friendship, love, and respect. Kim might not have Clara’s confidence or experience, but her desire to dominate was equally as strong, and from what Emily could see she most definitely had Amy wrapped around her finger already. Emily was excited, but also nervous; she knew that her performance, appearance, and attitude would reflect on Clara, and while she would do her best, she knew her training had really only begun, and she didn’t want to embarrass her new mistress.

                After her workout, she showered and carefully shaved, she knew that her appearance would be carefully appraised first by Amy and then by Clara long before Kim arrived. Shaving around the cage took a bit of practice but she took her time; Clara would be equally displeased by both stubble and razor burn. She had pressed her skimpiest uniform the night before, and taken peroxide to the lace trim until it was perfectly white, Amy standing over her shoulder to help if needed. A uniform that covered next to nothing, the tallest heels she could realistically serve in polished to a shine, no panties, makeup very carefully applied, adjusted and fussed over, her entire body shaved smooth, her candy-apple red cage polished, and her bottom decoratively plugged; she was as ready as she could be.

                Amy inspected her uniform before the pair headed upstairs; she was dressed nearly identically, though the cut of her uniform was slightly different, to accentuate her curvier hips and bottom. Amy’s hands moved over Emily’s body, tidying a bow here, adjusting her maid’s cap, and lingering a little on Emily’s sensitive nipples and exposed bottom. She tapped her nails against the base of the jewelled plug inside Emily’s bottom, and leaned in for a gentle kiss with just a little tongue. Not enough to ruin either girl’s lipstick, but as a well-earned reward for Emily, who had surprised her by being extremely prepared in getting dressed.

As Amy broke from the kiss, she looked Emily up and down once more, and with a smile she wiped the single dewy drop of pre-cum that had escaped Emily’s cage during her inspection from the inside of her pale thigh. She held it to Emily’s lips as sighed softly as Emily licked her finger clean; clearly Amy was nearly as excited for Kim’s visit as Emily was.  Amy gave her an encouraging squeeze and pat on the bottom before they separated to do their separate duties. Emily to begin preparing breakfast and Amy to awaken Clara; the sole duty in the household that remained exclusively Amy’s.

                Emily positively vibrated with excitement as she prepared breakfast. Clara must have been excited too as she kept Amy far longer than usual in her ‘wake up duties’ leaving Emily to prepare breakfast on her own. Finally, the pair joined her in the kitchen just as the eggs were coming out of the pan; Amy red-faced and flushed in her somehow still-immaculate uniform, and Clara languid and relaxed in the satin bathrobe she breakfasted in on the weekend. Emily smiled to herself knowing that Amy had already had a several course breakfast before reaching the table, and just how desperate she must be feeling, while Clara seemed extremely relaxed indeed.

                Emily served Clara first, then Amy, and finally herself. Clara liked a hearty breakfast on her days off; eggs two ways, bacon, French toast, coffee, fresh fruit, and roast potatoes. Emily herself was too nervous to be terribly hungry, and she mostly picked at her eggs and a bit of the fruit, more pushing her meal around her plate to give the appearance of eating than anything else.

                Clara smirked knowingly; “Excited to meet Kim tonight, Emily?”

                Emily’s stomach untied itself slightly; talking about it helped ease her anxiety. “A little, yes. Amy has told me so much about her.”

                Clara laughed and dabbed the corner of her mouth with a napkin. “I’m not surprised; Amy had quite a weekend the last time Kim visited. She barely left the guest room for two days straight.” She leaned across the table, her eyes conspiratorial; “Play your cards right and maybe you’ll be sharing the big soft bed in the guest room with Kim this time around. It’s Kim’s choice, and I did let her know that we had a cute new plaything staying with us; then again she assured me after last time that Amy was an extremely entertaining companion.”

                Emily’s cage tightened immediately at the thought. She didn’t want to take away from Amy’s fun, and she looked at her fellow maid a little guiltily; but Amy was focused on her breakfast, or more likely on her memories of Kim’s last visit. Amy was absolutely devoted to Clara, but theirs was an extremely open relationship; Clara openly took whatever lovers she wished and within clear limits allowed Amy the same freedom as well. The incredible closeness and intimacy of their relationship, combined with the total lack of jealousy always surprised Emily.

                Clara broke into both girls’ daydreaming with more practical matters. The house was already spotless, as Amy and Emily had spent the last week making it so, but Clara had a very particular menu picked out for Kim’s first meal at the house, and she made sure to review it with both of her maids point by point. Clara was very much a “big picture” person, and after listing each course it was Amy who instructed Emily on the details of the preparation itself. Amy was organized and thorough in a way Emily doubted she herself could ever be.

Emily did her best to listen attentively, but her cage was still dripping at the thought of an evening with Kim, and since she wasn’t wearing any panties she worried she might be leaving a bit of a mess on the chair. She squirmed a little, the plug pleasantly sinking a little deeper into her, though the cage remained as solid, unforgiving and as tight as ever. When she was absolutely certain Clara wasn’t watching she dabbed at her moist thighs with the napkin in her lap. Leaving a mess in the dining room before a dinner party would be a bad way to start things off.

                Kim’s arrival was heralded by the ringing of the doorbell. Emily stopped chopping onions at the sound, her ears straining for any sounds coming from the front door. Clara answered the door herself, and quickly showed Kim through to the kitchen where Amy and Emily stood cooking; Amy running the oven and 3 burners single-handedly, with Emily chopping, mixing, and stirring at the counter.

                Kim was… if anything, prettier than Amy and Clara had built her up to be. She had been described as “busty” but that was a laughable understatement; Kim was stacked. Emily, who aspired to a C-cup and barely filled out a B wasn’t sure there were enough letters in the alphabet for Kim’s bra size. Beyond that, she was stunning; deep brown eyes, generous hips, a surprisingly small waist, and in Emily’s own personal opinion; eminently kissable lips. More than that, she radiated some of Clara’s intense Domme energy; from her body language there was no hint that she was going to join in the cooking, she was here to say hello and give Emily her bag to carry up to her room. She was a little hesitant in her manners, her command for Emily to take up her bag nearly as much a question as an order, but Emily was submissive enough that it didn’t matter.

                After a brief introduction Clara spirited Kim out of the kitchen and into the living room, Emily’s eyes following the pair to fetch Amy’s bags. Laying the suitcase on the bed in the guest room she looked around, as it was the room Emily had spent the least time in. Amy and Emily slept in the maid’s quarters downstairs, and only rarely did either (or on some very memorable nights both of them) get to sleep in the king-size bed that Clara herself slept in. The guest room was little used and so required only light cleaning. It was a bright and airy room, with a chest of drawers and a tall wardrobe. Being Clara’s guest room there was a surprisingly large amount of both wardrobe and dresser taken up by toys both painful and pleasant, as Clara’s guests were always welcome to Amy’s, and now Emily’s services while they stayed over.

For the rest of the afternoon Amy got to wait on the pair only when Clara rang the tiny silver bell to call of more coffee or pastries, and Emily was frustratingly stuck in the kitchen. She heard her name several times come up in conversation, but she couldn’t quite make out what was being said, and Amy met all of her questions with the same knowing smile and frustrating silence. Emily fought a constant battle between trying to keep her uniform spotlessly clean, prepare the dishes assigned to her with the level of care and attention Amy demanded, trying to overhear what was being said in the living room, and leaking whilst fantasizing about the guest room upstairs.

                Dinner itself was an elaborate affair and required the full attention of both Amy and Emily. Between preparing food, waiting on Clara and Kim, keeping their mistresses’ glasses full, and cleaning up after themselves, by the time dinner was nearly finished the pair were spent. When the last dish went into the oven to keep warm and the salad was ready to be served, Amy had taken a final opportunity to adjust Emily’s clothing, hair, and makeup. Admittedly, a full day of preparing food and dripping quietly from her cage had left Emily in some need of sprucing up, and she was grateful for the help, which she returned by quickly brushing out Amy’s hair and scrubbing out a small grease spot from the hem of her uniform.

                As they brought out the entrees Clara motioned for them both to stay. Amy set the decanter on the sideboard, smoothed her uniform, and smiled; the meal had gone remarkably smoothly. Emily wasn’t the perfect assistant, but she had managed to keep up for the most part, and at a minimum hadn’t horribly fouled anything up. She breathed a deep sigh of relief; the meal was above reproach, Emily’s uniform remained mostly serviceable, the wine was breathing, and dessert was nearly ready to come out of the oven. Emily could be trusted to manage the post-meal coffee; both making it and serving it; she was competent enough for that… she was just regretting a tiny stain on the tablecloth when Kim spoke up.

                “So… Clara… I love the matching little cages you keep them in. I don’t remember Amy being so… decoratively adorned on my last visit.”

                Kim was still somewhat new to Clara’s particular brand of loving dominance, and while she had learned a great deal there was still a stubborn streak of nervousness that remained. On this evening the wine had been pouring freely, and while Kim wasn’t drunk a slight pink hue to her cheekbones spoke to a touch of liquid courage flowing through her veins, making her bolder. Questions like that were something Clara had no issue saying in front of her maids, but in Amy’s experience those sorts of questions were normally something Kim asked behind closed doors. Moreover, she was clearly interested in Emily, leaning in close to her, making all kinds of eye contact, and always asking for her specific assistance in refilling her glass.

                Clara for her part was clear-headed and keen eyed. She could see Kim’s obvious attention and was happy to revel in it.

                “Oh yes… I suppose we met some time after Amy still needed her cage, but she did her time in chastity training with me. She wasn’t locked when we met, you know. She was raised free, went to school free, she actually got to be inside me when we first started dating…”

                Emily looked over at Amy, who was beginning to blush. Amy? The perfect maid? Her role model had actually been INSIDE Clara? Her eyes widened with surprise until Amy caught her staring and shot her a dirty look. Clearly this wasn’t something that she was going to learn more about right now. Emily looked at her shoes to avoid Amy’s eyes while she pondered this new development. She would definitely be asking Amy about this the second the two of them were alone.

                Clara swirled the crimson wine in her glass with a smile, her eyes sparkling.

                “My darling Amy is blushing, but she shouldn’t be. I’m so incredibly proud of her. The cage tonight is partly for my own vanity; I do so love her and Emily matching… but really it’s not that I don’t trust Amy, it’s that I don’t trust Emily.”

                At this, Emily started and looked up at Clara, a protest forming on her lips. She looked straight into Clara’s piercing eyes, dancing with mischief. She was having fun baiting her. She was expecting a response from Emily who barely bit off her comment at the last possible moment. Clara almost looked a little disappointed, but her smile widened nonetheless.

                “Oh yes, Kim. Amy is entirely trustworthy. Ever since I broke her, body and mind, she would never even consider disobeying me by touching herself. Not that she can even get hard these days…”

                Clara leaned in towards Kim, her voice a theatrical stage whisper;

                “It’s just Emily has the softest, sweetest little mouth you can imagine, and the second I left those two alone I guarantee she would be practically begging to have Amy’s tiny little cherry in her mouth. Amy is a very, very good girl but she’s only human after all; she might not be able to get hard, but even a perfectly behaved girl wouldn’t say no to Emily’s lips wrapped around her. She’d try to resist, but eventually she’d be shooting her limp little load into Emily’s all-too-willing mouth night after night, which would begin all sorts of bad habits. The cage isn’t because I don’t trust Amy, it’s because I can’t trust Emily… yet.”

                Emily could see Amy flush scarlet down to the middle of her bared chest, and she imagined that in that respect it was much like looking in a mirror; her face burned with shame. Clara was… probably right, but she wanted… no NEEDED Kim to like her. Having Clara so expertly pick the two of them apart was a little sexy but it was also deeply humiliating to have her know them both so well. Amy was HOT; sharing a bedroom with her meant sharing a bed for an hour after light out more evenings than not, which was still incredibly fun, even with the cages. Emily had known on some level that her staying with them had meant Amy had to be locked again, and she couldn’t argue the logic, but she now felt a little bad knowing she was the entire reason why.

                Kim giggled. “They both look so cute. Matching uniforms, matching cages, matching eyes, matching hair… they could almost be sisters.” Kim took another sip of her wine, the glass nearly empty now; “I don’t know how can you trust Amy to be so well-behaved? If you left her free, why wouldn’t she just… you know… fuck Emily? I know I would…”

                Emily’s cage tightened as Clara laughed amiably, resting her arm gently on Kim’s forearm as if to restrain her. She and Amy stood rotted on the spot. Being spoken about openly and frankly as though they weren’t present was something they were very used to from Clara, but it was something new from Kim.

“Oh Kim… Amy isn’t capable of that anymore. She can’t even get hard without her little pills these days, on the rare occasions I let her have them…”

                Kim turned towards Amy, who stood nervously fidgeting, her cage feeling very conspicuous under Kim’s eager if slightly hesitant gaze. She was still learning the role of a Domme, and in times like this it showed. Clara has no hesitation in running her eyes over Amy’s body, or Emily’s. She didn’t mind staring at what she considered her property and she would get a good eyeful until she decided she was satisfied. Emily always got tiny shivers at the base of her spine when Clara looked at her like that, and she was quite sure that Amy did too.

                Kim on the other hand clearly found her attractive, her eyes running up Emily’s long, lean legs and lingering on the small breasts that poked out of the top of her uniform. Yet she looked away immediately any time Emily tried to make eye contact. It was cute, but Emily was hoping to earn an invitation to the big bed in the guest room with everything that such an invitation promised. Kim was frustratingly shy…

                Clara continued her explanation; “You see Kim dear; Amy’s training began a very long time ago when she first entrusted me with her keys. It was a very long and difficult process for her. She had to give up penetrative sex with me, then me touching her little clit at all, then even the feeling of her own hand as we moved to permanent chastity. All that within just the first 18 months.” Clara motioned for Emily to refill her glass, which she did, managing to not spill a single drop onto the table though she was hanging on every word.

                “After that, it was a simple matter of slowly sizing down the cage and letting chastity work its magic. A girl stops getting hard after a few years in a tight enough cage, you know. I waited and I teased and I watched. After about 3 or 4 years Amy’s cage stopped twitching no matter how much I teased her. I was so proud of her when that happened. Once a girl can’t get hard and she accepts that the cage doesn’t come off her mind changes too; her little cherry isn’t made for pleasure, except on the very rare occasions when I decide that it can be. She would never dream of touching it without my permission, and she is genuinely happier with other forms of stimulation. Once a girl loses not only the ability to get hard, but the desire to get hard as well, then the cage simply isn’t needed.”

                Kim was listening rapt, as was Emily. Amy was staring at her shoes. She was nearly as proud of her progress as Clara was, but having it spoken about so openly was still embarrassing. Kim held her glass out for Emily to refill. With Kim’s eyes so clearly fixed on Clara, Emily thought it wiser to simply take the glass from Kim’s hand and fill it herself.

                “Oh… I always have so much more to learn, Clara…” Kim chewed on her lower lip, regretting her relative inexperience. “What about Emily then?”

                “Well Emily is only here on a temporary placement for the summer. She’ll most likely be going back to Rattangrove in the fall. However, she is free to sign on with us instead, join our little household, and if she decides that’s what she wants to do, well then we will have a solid 4 month head start on breaking her little clit, as I won’t be unlocking her for the summer.” Clara locked eyes with Emily as she spoke;

“Ultimately, after 5 or 6 years, Emily will be just as limp and obedient as Amy, and she won’t need the cage either. She’ll be a wonderful addition to my stable alongside Amy, or…”  Clara’s eyes narrowed conspiratorially; “Maybe as your own first maid, Kim…”

                Emily felt her fingers go numb at the thought of being caged so long that she “broke” as Clara put it. Distantly she felt the glass, now filled with wine slip from her unfeeling fingers. It was halfway to the ground before her mind finally registered the danger, and she made a desperate grab for the tumbling goblet, far too late to arrest its’ fall.

                The glass practically exploded when it hit the polished floor, and one of Emily’s first thoughts was a twinge of regret at how long she had spent polishing it to the mirror-like shine, now ruined. The dark red liquid splashed over Kim’s running shoes and tight jeans, as well as across Clara’s pumps and up her calves. Small crystalline bits of the glass skittered and slid across the floor nearly to the threshold separating the kitchen and dining room, and the sound of breaking glass filled the room, leaving behind it a very still and foreboding silence.

                Emily barely dared to glance at Clara, whose eyes flashed menacingly once before she regained control and let out a breath slowly. To someone who didn’t know Clara well they might think her unperturbed, but Amy knew just how deeply upset Clara was by this.

                Clara stood, stepped around her chair, and slid the chair neatly back into its place at the table.

                “Amy dear, would you be so kind as to hold dessert for us? I think it’s time that Emily helped me demonstrate some of the finer points of my training regimen…”

                Emily swallowed hard. The night had been going so well up to now.

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