The Kink Retreat

I jerked up in shock to the sound of my cage opening, Master ushering me out. Still groggy, clit straining from the morning excitement, he sat me down in the bathroom, brushing my teeth. My own hands stolen from me by the jacket, I simply sat still as he helped, feeling silly and embarrassed. Master gently brushed out my wig, giving my face a light wash, one final look over his sissy. Happy, he told me Miss Anna was expecting me in the service rooms, and I best not be late.

I gasped, pleading to be let out of the jacket, or at least something to cover my clit. But Master denied both, pushing me out the door and closing it, soon finding myself in the hallway completely exposed. I didn't even know where the service rooms were! Cursing lightly under my breath, I made my way towards the lobby, blushing deeply at the smiles and snickers of each person I passed.

Relieved, I saw a maid at the hotel, the baby blue dress similar to the one I had seen yesterday. I blushed deeply when I realised it was the same maid I had seen yesterday, her cute smile and outfit turning me a deep shade of red. Still embarrassed, I asked where I could find the service rooms, telling her I had to meet with Miss Anna. Giggling at my attire, she beckoned me to follow with a finger, turning around with confidence as I obediently trailed behind. She led me through a maze of hallways in the back of the resort. so thankful I had gotten help, knowing there was no way I would have found it on my own. A mischievous smile on her face, she cupped my clit with a hand, forcing a moan from my lips. Squeezing and tapping, she whispered that she'd find me later, so that I could properly thank her.

Excitement rushing to the surface, fueled by Master's denial from the previous night, I was left in front of the door as she walked away, clit straining hard in its cage. Miss Anna opened the door to my frustrated self, eyeing me up and down. Tutting, she scolded me for being so excited this early in the morning, shushing my explanation as she led me inside. Blushing, pouting from being teased, I sighed as she let me out of the jacket.

Showered, I followed Miss Anna to what looked like a seamstress workshop, strips of baby blue and black all over. I curtsied to the uniform manager, quickly fitted into my own maid dress, clit betraying my excitement to wear it. Tight on my waist, a perfect fit, I giggled as I swished the skirt of the dress back and forth, petticoats pushing it far off my body. A light spank made me squeak, apologising as I stayed still through the finishing touches. Bow in my hair, solid white nylons and heels slid on, and the apron secured around me. Miss Anna returned to inspect me, smiling at the results.

On my knees in front of her, she discussed the rules of today, as well as what was expected of me. I would shadow another maid for the day, to learn the ins and outs of being a maid at The Kink Retreat. Hooking a finger in my baby blue collar, she told me to respect the colour my Master had chosen for me. Nodding, telling her I would be a good girl, Miss Anna said there was just one more piece to my uniform. Bent over, my panties and tights pulled down, I softly moaned as she slid a plug inside of me, snugly fitting against my g-spot.

Showing me her phone, Miss Anna told me that management as well as some choice guests had access to that plug, and that the more I behaved, the nicer they'd be with it. Set to a teasingly low setting, she smiled as I was sent out, my first day as a resort maid under way. Focusing on walking in my heels, desperately trying to ignore the vibrations currently coursing through me, I made my way to the room I was assigned to, immediately groaning as I saw the girl I would be shadowing for the day.

Smiling ear to ear, Rachel, the evil maid who had shown where to go earlier that morning, laughed as I curtsied, explaining the situation. Eyeing me like a present, she playfully fluffed my dress, complimenting how adorable I looked. Blushing, I thanked my tormentor with as much sass as I could muster, being quickly put to work. She taught me how to undress the bed, fold towels, what needed to be cleaned; all the duties that came with each room. Rather enjoying this unsuspected sense of power, Rachel sat back as I did all of her work, scolding and spanking each time I got something wrong.

Among the tasks she directed me in, the tell-tale curtsy all maids knew was the first. A slight pinch on each side of our dress, holding the fabric perfectly as we curtsied. One leg to the side, bend of the knee, smile on my face, looking ahead but no direct eye contact. Rachel had me hold my pose for five minutes, making minor adjustments. Over and over I curtsied, until she was convinced I had it right. Through it all my plug pulsed away gently, a constant stream of whimpers escaping my painted lips.

Her wandering hands kept me excited all day as we moved from room to room, rubbing my clit and plug. I could barely focus on simple tasks, my frustration building with each teasing touch from my "mentor". Focusing intently on folding each towel to have a perfect point, I softly moaned as Rachel's fingers traced over my excited little clit. Dress lifted, unable to escape her pressed against me, I whimpered as I desperately tried to ignore the strain in my cage. That familiar ache that came with being a chastised sissy was often something I looked forward to, but in the hands of this cute and evil woman, I nearly begged for mercy.

Teasing that I would get in trouble for the growing wetness in my tights, Rachel smoothed out my dress as I was released, continuing to clean. As we were stripping the bed, the owners of the room came back from a late brunch, smiling ear to ear at the maids currently residing in their room. Dresses in our hands, we curtsied wordlessly, just like how I had been taught. Female hands adorned my shoulders, pushing me to my knees, soon finding myself staring up at a set of excitable eyes.

Without looking away, seeming familiar with Rachel, the woman talked back and forth with her, finding out information on the new maid in the resort. Nearly sneering, Rachel happily told them all about me, how she found me this morning, about my Master, and my role for the day. Her husband gave Rachel a friendly hug, showing dominance but not over stepping the casual atmosphere in the room. Mischief returned to his wife's eyes as she stared down at the baby blue sissy before her, knowing they could have a little fun before sending the two maids on their way.

Taking out her phone, Miss Amelia, as I was directed to call her, quickly found access to the plug gently vibing inside of me. I gasped as it roared to life, firmly snug against my g-spot, pulsing through my entire body. Shaking, feeling my clit instantly trying to cum, I whimpered as her hand cupped my chin, holding my gaze as she smiled, enjoying my attempt to withstand the aching desire to cum. After all, I was a collared sissy. Regardless of who owned me, no collared sissy cums without permission.

Ensuring she had my full attention, Miss Amelia informed me that she would turn off my plug once I made her husband cum. Gulping, already feeling that familiar build up, I nodded, quickly shuffling in front of him, unzipping and fishing out his cock. Rachel knelt in front of Miss Amelia, hands playing with her hair, while they both watched my lips eagerly wrap around the task at hand. I spared one glance at the eagerness in Rachel's eyes, before focusing on his gorgeous cock.

Whimpering, knowing if I didn't get that plug turned off soon I would explode, I slid all the way down his shaft, like the good sissy cocksucker I had been trained to be. Hands gripping my petticoats for support, I moaned as I moved up and down his cock, a chorus of groans above me urging my movements. The irony wasn't lost on me that I was so desperate to make this man cum, in order to prevent my own orgasm, when all I desperately wanted was to feel my own release. It had been years since I'd had an orgasm out of my cage, permanently given a clit by my Master. Which, despite seeing the faces of all the men I had made cum in that time, I knew cumming as a sissy was far better suited for me. The only issue being those releases were few and far between.

Clit straining, desperation building to a point of no return, I heard him groan, filling my mouth with his cum. Patiently waiting as he fucked my mouth through his orgasm, I sat while Miss Amelia inspected my handiwork, smiling as she slowly reduced the vibrations in my ass. A mix of relief and frustration washed over me as my own orgasm subsided, safely still a good little sissy.

Still playing with Rachel's hair, Miss Amelia commented on how cute I looked with a mouth full of cum. She beckoned me forward, saying such a wonderful gift like that shouldn't go to waste...or unshared. Realisation spread over Rachel's face, pleading with the woman holding her still, but those knowing and mischievous eyes now directed themselves at her. Rachel silently groaned, grabbing me by the collar as I was pulled in, locking lips with the sissy she had been tormenting all day. Sometimes, just sometimes, karma plays out exactly as it should.

Leaving the two maids to swap her husband's cum back and forth, Miss Amelia kissed her husbands cheek, who returned her affection ten fold, appreciating the gift she'd just given him. They went about unwinding, the scene before them a welcomed back drop. Satisfied, Miss Amelia finally let us finish, get cleaned up, and sent us on our way. For the rest of our shift, Rachel simply glared at me, happy to blame the sissy for the situation we had found ourselves in. I giggled to myself, thoroughly enjoying her being put in her place.

Soon enough, we were back in front of Miss Anna, curtsying together. Her eyes drank us both in, inspecting our uniforms as she questioned Rachel about my performance. Surprisingly, Rachel said I did well, and would make a great fit as a maid. Smiling, Miss Anna congratulated me, having passed my first test. She informed us both that for the rest of the week we would be working together, graded at the end for my performance. Any transgressions on my part would be shared by Rachel, and vice versa. Head down in my curtsy, I could still feel the glare coming off my new mentor.

Changing out of my uniform, handing it to the seamstress, Rachel and I headed to the changing room, sighing with relief as I saw an outfit had been left for me. As I reached to see what Master had planned for me to wear, I felt Rachel's hands turn me around. Steel in her eyes, she pushed me to my knees before her, so close to her naked pussy. Staring down at me, she informed me that if she was to share my fate, then I would listen to her every word. I would do everything I was instructed to do, exactly how she saw fit. Words stolen from me, not expecting to be dominated this easily, I nodded, softly whimpering in her hands.

Hooking a finger in my collar, she lent down, kissing me gently on the lips, tasting the cum we shared earlier. As if to seal our little arrangement, Rachel pulled me into her pussy, moaning as her new toy made her cum. A satisfied smile, our roles ironed out, Rachel helped me into my outfit for the evening, a pink schoolgirl complete with pigtails and all. Holding my panties hostage, she had me bend over, hand placed on my locker. Further enforcing the control she now had over me, I whimpered as she spanked my bare ass, skirt flipped up, out of the way. Rachel smiled as she watched my ass redden, teasing the plug inside of me, collecting some pre-cum leaking out of my exposed cage.

Still holding my panties, she stared into my eyes as I sucked her fingers clean of my own excitement. With a sly wink, she left, leaving my clit aching in its cage, bare and threatening to show underneath my tiny schoolgirl skirt. Blushing deeply, I ushered myself along the halls, finding my Master in the lobby. I tried to explain myself while he inspected my outfit, but my words fell on deaf ears, placed over his lap and punished in the open for not having my panties. Tears welling in my eyes, I resisted begging for mercy as he turned my ass an even deeper shade of red.

Sniffling on my knees in front of him, Master informed me next time to not be late, and to wear exactly what he left me. I knew full well that Rachel would steal something from me each day, making that promise impossible to keep, but there was only one thing I could say.Yes Master. My baby blue collar slightly clashing with my outfit, but a necessary part of the resort, Master paraded me around all night, quickly finding myself at the mercy of complete strangers. I was brought back to Master's room exhausted and sore, my mouth and throat completely coated in cum.

For the rest of the week I followed Rachel around, our matching baby blue dresses marking us perfectly for the staff and guests. I met some of the other maids working there, some just for the week like me, and others there full-time, like Rachel. Yet, true to her word, I continued to be at the mercy of my new mentor. She continued to correct my work, ensuring it was perfect and to the standards of the resort, while sneaking in time to torment and humiliate me.

Miss Anna would always inspect us together, asking about my progress. Satisfied with Rachel's account, and the feedback she got from other guests, she would always smile knowingly at me, calling me her good little maid. After a day of wearing pretty dresses, being used and bossed around, my clit straining constantly, her praise was almost enough to make me cum right then and there.

Every day after our shift, Rachel would shove her pussy onto my mouth, taking the orgasm denied to her all day. Tender and yet dominant, she would thank her little pet, saying what a good girl I had been all day, much different than the docile maid she was for Miss Anna. Teasing and spanking my clit, pressuring my plug, Rachel always took my panties for the evening in what she called her "payment". I never told her it got me into trouble with my Master, but I am sure somehow she knew.

After my nightly punishment for not having a complete uniform, Master would bring me around the resort, showing me all the unique and different aspects to it. Dungeons, sunrooms, casino, dance hall, bar, lounge, restaurant; I was amased at how expansive the resort truly was. Even though I was tired from cleaning all day, I enjoyed all the different aspects there were to explore, and the people who took part in them. We met couples, owners, slaves, some first timers and some returning veterans. I was lent out many times through the week, always under the watchful eye of my Master, thoroughly enjoying my ever-changing role each night.

On our final day I found myself a bit sad to leave, enjoying the pretty maid dress I had been given each day to flaunt about in, as well as the attention the colour of my collar had awarded me. Even Rachel, despite her teasing and enjoyment in humiliating me, was someone I had grown close to, and would miss. Kneeling in my travel dress, I waited for Master to finish getting ready, having packed our bags. Finished, he clipped my leash to my collar, heading to the lobby.

We dropped off our bags near the car, heading to say good bye to Miss Anna. I was, after all, still wearing the resorts collar. Secretly, even though I had many, I did hope they let me keep my maids dress, begging Master to wear it from time to time. Miss Anna smiled, embracing Master warmly, chatting as I waited patiently beside them. Soon she beckoned for us to follow her as she had some "parting gifts" for his sissy. I liked gifts!

Brought in to the maids changing room, I was stripped down completely, only my collar left to cover me. Blushing, clit straining in my cage, I felt Master tilt my head up in his hands. He asked how I had enjoyed this past week, being one of Miss Anna's maids. I beamed, saying how much I enjoyed it, being under her control, wearing such pretty outfits, being of service to such nice, kinky people. Smiling, Master said he was glad, for he and Miss Anna had a surprise for me. Curious, unsure what it would be, my eyes widened as I saw Rachel step into the room.

She wore an exact replica of the maid uniform we had worn all week. White tights, trim, and petticoats, pushed out from her tight waist. Slightly puffed sleeves, shortened hem to show more than enough leg, and reasonable heels you could wear all day. The only difference being the bow in her hair, and the dress itself, was a complete shade of deep, dark, red.

As was her collar.

Speechless, knowing exactly what that meant, I trembled on my knees as I saw what was in her hands. Miss Anna took the larger dress from Rachel, knowing before she said it that it was for me. I fought reaching out to touch the beautiful fabric, playing with the lace, running my hands along the outfit I so loved. Master embracing me from behind, lending me strength, informed me that Miss Anna was so pleased with my work this past week, and how many guests had stated that I was a delight, a highlight of their trip.

Still lost for words, not that I had been given permission to speak regardless, I saw that beneath the dress Rachel carried two other components to my outfit. A matching collar, deep red like hers, making me whimper from the implications that came with it. I thought back to the woman being used the first night I was here, to the many times I saw someone pulled away, a toy to whomever chose at the resort. Mouth dry, I felt my clit scream at me as I saw the matching cage in her other hand.

Small, oh so small, and a matching colour to the rest of the ensemble. I had been denied an orgasm all week, clit aching as it pulsed with excitement. I knew before Miss Anna even outlined what this all meant that I would say yes. I knew I wanted that cage, wanted that collar, and wanted that dress. I knew it meant being property of the resort, a toy for as long as it adorned my neck. I knew Rachel would continue to control me, torment the sissy under her heel, even more so as wearing her own red collar meant she herself would be used more as well.

In a daze as they outlined what saying yes meant to staying there under Miss Anna's control, what would be expected of me. Rachel and I would be the only two red maid's they had, others being a mix of black and baby blue. As I stared up at my Master, the man who had trained me and changed my life, I saw the encouragement behind his eyes, knowing this was his intent all along. Unable to speak, I could only nod, happily sealing my fate as a Kink Retreat maid.

My Master, who for the first time in years I would instead call Sir, told me how proud he was. He'd be back each year to see me, my progression, my training. Making sure to book a room I was in charge of. Blushing, I hugged him deeply, thanking him for bringing me here, before watching him walk out the door. Still in a bit of a daze, I smiled at Rachel as she prepped me for my new cage. I giggled at the glare she shot me when I commented on how well red suited her.

Keeping me soft by spanking my excited balls and clit, the new cage slid on perfectly. Hugging every part of my clit, feeling the inner material that gripped my skin. Miss Anna informed me that the harder I pulled, the tighter the material became, stuck in that cage until I was released. Horror struck as I watched her hand the keys to Rachel, that devious smile haunting me as they disappeared in between her breasts.

White stockings slid up my legs, garters holding them snugly in place. No panties or tights for red maids after all, they would simply get in the way. Dress hugging my waist perfectly, emphasised by the petticoats pushing the hem of my uniform outwards, I blushed seeing the final product in the mirror. Rachel beside me matching, a tight comforting squeeze as we held one another, excited for this new adventure. Her final finishing touch was the plug shoved inside of me, already vibrating and teasing, my poor clit trying to get used to its new, permanent home.