The Pink Maid

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"It is 7am..."

"I know! We're already so far behind!" She brushed past me, a large bag in her arms, letting out another defeated sigh as I shut the door. On auto-pilot, I moved back to my bed, collapsing on top of the covers to a cheerful command from the other room, "don't you dare fall back asleep!!"

Pulling me up, Amanda ushered me to the bathroom, shoved into the shower. I felt myself slowly waking up under the warm water, sighing with relief knowing I had probably another week before I had to put my body through another sugaring. When you had no interest in it...body hair fucking sucked.

Dried off, enema complete, I stood in front of Amanda feeling more myself, slowly falling into becoming more feminine. She smirked seeing the change, guiding me to my make-up chair, feeling my ass pulse around my plug as I sat down. I moaned as she ran hands through my hair, handing me a cup of tea as I sighed, easily falling under her control. She fussed over my face for far longer than I ever did, but I didn't mind, happy to sit there and submit to her fun.

Brushing and placing my wig into place, Amanda smiled at her finished product. Dramatically, she had hid all of my mirrors, wanting to make, as she called it, agrand reveal. Good to know that even when she was dominating me, Amanda was still the same moron I was great friends with. Sighing, I rolled my eyes at her while I sat on the end of my bed, giggling as the first stocking slid up my leg.

Soon I was left whimpering as I felt Amanda's hands smooth out the nylons, garter straps snapped into place one by one. Lingering touches, moving her fingers to graze my clit, I was left staring into her eyes with an eagerness, the desperation coursing through me far greater than it had been in the past. She returned my look with a smirk, offering a friendly tap on my clit, bringing me to my feet for the rest of my uniform.

I could barely think as I watched her work, seeing someone else complete my routine, letting her into the secret world of Rory. Yet somehow it just felt right, felt comfortable, felt safe. With each new piece added Amanda ran her hands over me, keeping that excitement brimming inside of me, blazing in my eyes as I stared down at her. She simply grinned, knowing exactly what effect she was having on me.

Kneeling in front of me, she placed the headpiece on top of my wig, cupping my chin as she stared down. "Are you ready to be a good maid for me, today?" I whimpered, nodding with wide eyes as I gulped, unable to explain just how excited I currently was. Amanda just smirked, grinning at the silly sissy maid comfortably under her control. "We are going to have so much fun, Rory."

Soon Amanda sat smugly in her chair at the table, cup of tea in hand as she watched me diligently. Occasionally she threw out comments, having me re-do certain chores, offering 'suggestions' as to how I could be doing it better. With each one I glared at her, knowing my way was better, forced to appease this grinning monster I had let into my little world.

Throughout the morning Amanda had me take 'breaks', finding myself on my knees to rub her feet, her calves, or simply to rest there while she playfully teased my poor clit underneath my skirt. Then I'd be sent back to my duties, seeing her eyeing me up from her phone, knowing her collection of pictures and videos of my maidly activities was growing.

Walking through the kitchen, I heard Amanda sigh as she came out with a dirty cup, the cup I KNEW she had just placed in there. "Rory, you have to learn how to finish a job properly." I tried to protest her little trick, but it was met by a stern shushing, grumbling at the injustice as I was bent over the table, an eagerly smiling woman behind me.

Amanda sighed dramatically, taking a crop out of her bag. "I had hoped not to use this today, but you have left me with no choice."

"I hardly think that is tr-ouch!" I jumped, feeling the first sting of her crop on my exposed ass, my panties pulled down. A few more bites were taken out of me to ensure my silence, before feeling one of her gentle hands rubbing and squeezing. Moaning, blushing from the vulnerable position, I could only stare forward as Amanda alternated between smacks and rubs.

Soon she had successfully chased away any brattiness I had, left a whimpering, excited mess as she rounded the table. Amanda knelt down, a sternness in her eyes as she spoke. "Are you ready to be a good girl for me again?" I nodded, the smile coming over her face making my clit twitch, wanting to make her happy. I felt my panties slide back up to cover my reddened ass, once more sent to tackle the rest of my chores.

My feet silently screaming at me for being in heels for so long, I sat down on the couch beside Amanda exhausted. She pulled me down to her lap, head resting while she brushed through my wig. I stared up at her, feeling a happiness connected to being feminine I had never felt before. I blushed, looking away embarrassed. "I'm really glad you're here, Amanda."

She smiled down at me. "Me too, baby girl. I am going to look forward to our Saturdays from now on." I giggled, hearing the phraseour Saturdays leaving a big smile on my face. Soon however it was replaced by a moan as I felt her hand disappear underneath my skirt, rubbing my poor clit in its panties, wet from the continuous control she had demonstrated over me throughout the day.

I heard her sigh with content as she watched me squirm, unable to sit still from her touch. "I think you're going to be wearing this for a while longer, Rory. I like what it does to you." I whimpered, unable to protest as her rubbing was tormenting my mind, fueling the desperation wearing the cage had built up inside of me. The thought of going even longer caged made me weak in a terrifyingly wonderful way.

Amanda finished her teasing with a playful spank, forcing a squeak out of me, soon following her to the bedroom. Stripped out of my dress and panties, I stood blushing in my heels as she rummaged through my closet, finding what she wanted. Soon I felt my waist corset being wrapped around me, the tight fabric ending just below my nipples, feeling my clit pulse each time she clipped another piece into place.

I turned to see her climb onto the bed, completely naked and yet I still felt far more exposed in my lingerie. With a finger, she motioned me between her legs, eagerly ready to have some form of distraction from how desperate I was to cum. Amanda groaned, tasting her own excitement from being in control, knowing exactly what she wanted from me as I set my tongue to work. Sinking into my pillows, she sighed, taking advantage of the mindset she had carefully walked me into.

Slightly thrusting her hips forward, pussy shoved eagerly against my tongue, I happily licked Amanda's beautiful pussy, listening to every wondrous noise she made. I could feel the pulsing in my clit as I ate her, trying desperately to ignore my own aching need, focusing solely on giving her the orgasm I knew she craved. An entire day of serving her, being underneath her control, sharing with her this profound secret I had harboured for years...I wanted nothing more than to make her happy.

With a groan, a loud aggressive tone I had never heard from her before, Amanda shoved my face hard into her pussy, feeling as she quivered and shook around me. Thighs clamped down on either side of me, barely able to breathe as she rode through her own orgasm, my eyes wide as I could simply wait, and watch. It was one of the most beautiful things I had ever seen.

Still shaking, a smile on her face, Amanda finally released me, laughing as she playfully pinched my nose. "Oh fuck Rory, that was a good one." I giggled, gently licking up and down her sensitive pussy, slowly becoming addicted to being between her legs. She continued to collect herself, running a hand gently through strands of my wig as she watched, sighing contently as I worshipped her beautiful pussy.

Finally I felt a finger rest underneath my chin, raising me to stare into her eyes. Amanda intensely held me in place, a stern dominating look spreading over her face that instantly melted me, clit once more pulsing in a desperate aching need. "Now," she said, her hold over me firmly in place, "are there any final steps to this Saturday routine that you haven't shared with me?"

I instantly blushed, giving away my final secret before I could even answer, my poor asshole squeezing around my plug in response. Amanda smiled as I pointed out my drawer filled with toys, leaving me on my hands and knees as she went to look. My blush deepened with each comment directed my way, soon shivering with a desperate moan as I felt that familiar cock sliding up and down between my cheeks.

"Mmmmmmm, yes. I think this will do nicely to finish off our day." I looked back at Amanda staying in place, my eyes wide with excitement as she slid a harness up her naked frame, my dildo resting between her legs. Tightening the straps, she smirked making eye contact with me, stroking her new cock slowly in her hands. I whimpered, feeling as if my clit would simply explode, shaking with the brimming excitement surging through my body.

I felt her sink onto the bed, legs on either side of me. Pushing down firmly on my upper back, I happily let myself be pushed into the mattress, ass high in the air. Amanda handed out a few spanks to make me giggle and squeal, before pulling out my plug, blushing as my excited little hole was exposed. She rubbed lube around my hole before plunging fingers inside of me, forcing moans out of my lips, reduced to a mindless slut that was desperate to be fucked.

Thankfully that was all Amanda required of me, squatting down to glide her new cock deep inside of me, listening to all my excited whimpers with a giant smile on her face. "That's my good girl, show me how excited being caged all week has made you." I moaned, feeling her spank my ass vigorously with each thrust, unable to respond or think as I succumbed to my growing orgasm.

Amanda continued, taunting me as she gave me the fucking I desperately craved. "I own you now, baby girl. Each Saturday I will do with you as I please, watching as the silly pink maid is a good girl." Whimpering, knowing I was close to cumming, I tried to say something, but I was unable to formulate anything close to a word. I could only listen as Amanda tightened her control over me, using her cock to hammer home any hope I had of regaining control of my clit.

With a growl, Amanda gripped my throat, bringing me back up to whisper in my ear. Her other hand reached around, clit firmly squeezed in her hand as I shook, eyes wide with shock. "Cum for me, Rory. Cum so I know you want this. Want me to control you. Want to give up your little ritual to me, to be my little slut. Cum knowing that I will never let you be free of that cage ever again."

I didn't even have to think twice, happily falling underneath her control. With a scream, her hand wrapped around my throat, I felt my mind explode as I came, my entire body tingling as Amanda fucked a week of denial out of my eager, desperate, little hole. Cum oozed, spurted, leaked, and dripped from my clit as I came, tears in my eyes from the intensity of my orgasm. Never faltering, she continued fucking me hard, watching intently as my release washed over me, solidifying me as her new toy. Her plaything. A pink sissy maid for her to abuse and enjoy.

Letting me cool down, my gaping asshole still high in the air, Amanda gently rubbed my back and ass soothingly. Eventually I felt myself able to function once more, nudging her appreciatively with my head as she smiled. I blushed seeing the mess I had made at the hands of her fucking, soon finding myself licking it clean as she held my wig back. She happily traced her finger along my clit to find the final remnants, watching hungrily as I wrapped my lips around it, sucking her clean.

Cupping my chin, she stared right into my eyes. "I think this is going to be a lot of fun, Rory." I giggled, echoing her thoughts, already straining in my cage once more. "Are you sure you're okay to stay in there? I wasn't kidding when I said I would never be unlocking you. I need you desperate each Saturday, my little eager slut."

I blushed. "I'm sure Amanda. I'm so happy I shared all this with you, this was the best moment being feminine and Rory I've ever had." Bashfully I hid my head against her chest, embarrassed at how gushy I felt at that moment. "I sort of don't want it to end." She hugged me tightly, planting a gentle kiss on my forehead.

"Don't worry, baby girl. I will take good care of you." I smiled, knowing that to be true, knowing my trust wasn't misplaced in my friend. As she left later that night, my keys disappearing into her pocket, I certainly felt a fear course through me at all the 'plans' she had mentioned running through her head. But it didn't stop the smile spreading across my face.

Hanging up my uniform, sighing happily at the beautiful pink, clit aching between my legs a constant reminder now of how excited I was to wear it once more each Saturday. How elated I now was to become the pink maid I so longed to be, under the control of Amanda. At first I had been terrified to let her in, to share with her this special feminine sissy ritual I had concocted for years. But she had improved on it, brought far more meaning to wearing it, and I knew things were just beginning.

I went to bed that night satisfied, happy, and content. I knew it would be a long week, a week filled with teasing, denial, aching, and a building desperation. But I also knew that at the end of it, I'd get to be her maid once more. Get to be her good girl. Get to serve her in whatever manner she required.

As I felt the pink cage constricting my poor clit, whimpering into the night...I knew it was exactly where I needed to be.

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8 Comments
awyldsideawyldside4 months ago

Why do sissies always need their cock caged?. That’s ridiculous. try it once without the cake if it’s not the same, lock them back up it’s up to Rory to decide not her.

mutualmast71mutualmast714 months ago

Love the premise of this and the details. I need to spend more time with this story!

AnonymousAnonymous4 months ago

wonderful story, i would love to be rory

rdoolittlerdoolittle4 months ago
One of your best.

Loved it.

CDsRsoHOTCDsRsoHOT4 months ago

A crossdressers dream cum true. Would love to spray my load all over you.....or deeply inside. Hopefully there's lots of pegging and pantyhose in your future!

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