The Pink Maid

"You don't..." Amanda gasped at me, amazed at the secret I just shared with my good friend. Blushing, I avoided her wide eyes as I nodded.

"Every Saturday."

"Every Saturday!? For how long!!?" She gripped my arm excitedly, not helping with my blush deepening.

"Ummmm, I don't know...a few years?" She made a small noise of surprise, smacking me.

"And you never told me!?"

"It's private! And a little embarrassing..." I looked down, slightly humiliated. But Amanda's grip tightened on my arm, giving gentle squeezes of encouragement.

"Not at all hun, it is so cute! Do you have pictures?" I smirked, unable to hide the truth from spreading over my face.

"No..."

"You fucking liar. Show me." I protested, trying to say it was my own personal private thing I did, which I hadn't shared with anyone. But we both knew that wasn't true, not to mention I had plastered partial pictures of myself over the internet for years. My feminine side, Rory, was unfortunately a bit of a slut. Amanda scooted even closer to me, determination flaring up in her eyes. "Now!"

I sighed, relenting as I pulled out my phone. Taking a quick look around the cafe to make sure no one was paying attention, I opened the folder holding all of my Rory pics, searching for the ones I wanted. Finding it, I handed Amanda my phone, which she took hungrily, eyes wide in disbelief as she looked on.

Each one depicted me flawlessly in my maid uniform. I had bought it years ago, tailoring the fit and adding little accessories here and there, until I was satisfied with the result. Now, as I donned it each Saturday, it had become a sort of ritual, a set of steps I took to get into the right mindset for the day. Even though I was incredibly nervous letting Amanda see me in it, I was also quite proud of how I looked.

The dress itself was extremely tight, with just a hint of shapewear built into it to help with my figure. Bright pink throughout, with an array of lacy ruffles and bows, all of which were a contrasted white, enhancing the look exactly how I wanted. Along the waist, all around the skirt of the dress, a strip up each of my sides, the end of each small, tiny puffy sleeve, and of course my high neckline. I loved how it gave a sense of a collar, tickling me as I wore it.

Pushing out the skirt were my layers of petticoats, always making me giggle the first time I got to twirl in them. The length was perfect to hide my caged clit and panties while standing, feeling it dip and threaten to expose me with each movement. I was aware constantly in my maid uniform how to be a good girl, and how to be a teasing little slut. The constant struggle drove me insane all day, adding to the frustration I happily delved into.

Pink stockings, transparent with solid tops, were held in place by my garter. I tried white ones initially, loving how they looked on my legs, but pink definitely went better with the outfit. My heels were a matching pink, the toes covered by an adorable rose. 8cm high, not too challenging to wear, but the sound on my floor as I minced back and forth cleaning was...intoxicating.

The final touches were always my elbow length gloves, the silky fabric such fun to feel all day as I ran my hands over my legs, or up my arms. A cute pink and white headpiece helped keep my blonde wig in place, the final part of the ensemble I put on each time, an act of sealing my fate until all the allotted chores were done. I could put my uniform on in my sleep, each step sending shivers through my body, heightening my excitement.

Well...okay I guess there's one more part to the uniform that I hadn't told Amanda about yet, being hidden underneath a mountain of frills. Three or four days before the weekend, I always put on my cute, tiny pink cage, a harness holding it snugly to my body. Enough time for my denial to kick in, that welcomed companion that turned my thoughts to Rory, to femininity, and to being a good girl. By the time Saturday hit, my mindset complete, I was always brimming with anticipation to be in my maids outfit.

As I watched her flick through the photo's, giggling at me being silly, I breathed a silent sigh of relief, happy that I wasn't being judged by my friend. Amanda made the odd comment here and there, blushing as the purpose of the dress was to indeed humiliate me to some degree. But I giggled along with her, explaining any questions she had.

Finally putting down the phone, a big smile on her face, she grinned as an idea popped into her head. "I'm coming to watch this weekend."

"You are not!" I glared at her, my poor face now permanently red with embarrassment from her suggestion.

"Mmmmhmmm! I have to see you in action! I bet you are so cute, please? Pleeeeaaaaaaaaaaaaaaaaaseeeeeee!!???" She put her head on my shoulder, batting her eyes aggressively. I huffed at her ridiculous attempt to look cute, rolling my eyes as I shifted away. We argued back and forth until our coffee had depleted, Amanda chasing me out of the café with her continued pestering. I tried, really tried, to persuade her otherwise, saying it was probably going to weird her out, but she held firm, never faltering.

With a loud, defeated groan, I agreed, a squealing Amanda hugging me with excitement. "But!" I exclaimed, "you only get to come in AFTER I am ready." She whined, wanting to see the process I described, but I refused, not comfortable with my friend seeing me in that manner, nor did I wish to explain what a chastity cage was!

She huffed, but agreed, pouting slightly as we said our goodbye's. Heading home, internally dreading what I had agreed to, I locked myself tightly after a shower to prepare for the upcoming humiliating weekend. A weekend I would never hear the end of.

Throughout the rest of the week, Amanda constantly pestered me for updates, all of which were denied. I whimpered each morning as the need grew and surged through me, that welcomed desperation beginning to build. By the time Saturday morning came around, I was aching in my little cage, a need for release pulling at the forefront of my mind.

Giggling, I set to work on getting ready, slipping into my ritual. First I cleaned out my ass, carefully sealed with a cute princess plug, sparkling in the morning light. Garters and stockings came next, followed by my snug pair of silk panties, perfectly hugging my caged clit, resting between my ass cheeks. After a few pictures in my mirror, already falling in love with my image, I moved on to the dress.

Sliding down my body, I softly moaned as the tight fabric was pulled into place around my chest and waist, thinning my more masculine form. Fussing with the neckline and shoulders, I finally sighed as it was perfectly in place, as I had done over a hundred times before. Next I stepped into my petticoats, shifting and lining my skirt until it fell perfectly against them, giggling as I twirled and spun. Staring in the mirror, I could just see the solid pink tops to my stockings. Perfect.

Make-up already done, wig set in place, I slid the long gloves up my arms, before stepping into my heels. I listened as they clicked against my bedroom floor, sending shivers through my excited body. Taking it all in as I stared in the mirror, I slowly placed the headpiece in place, the final part to my little routine. I felt the shift, knew I'd be Rory until my tasks were finished, knew I was now stuck as my own, happy pink sissy maid.

And I was about to show all of that to Amanda.

Suddenly terrified, I knew she'd be here momentarily. My mind began to torment me with doubt.What if she thinks I'm weird?What if this changes our friendship?Should I be sharing this side of myself? Over and over, scenario after scenario, I felt frozen in place as I bit my lip, torn out of self reflection by an eager knock on the door. My heart pounding in my chest, knowing it was too late to back out, I resigned to my fate as I slowly made my way over, welcoming Amanda into my apartment...and the secret life of Rory.

Holding my breath, I opened the door, seeing the big excited smile drop from Amanda's face. Instead her eyes grew wide with shock, mouth hanging open, as I demurely clasped my hands together in front of my uniform, awaiting her scrutiny.

"Fuck. Me." She stared, taking a step closer to run her hand delicately through my petticoats, moving up to feel the silky fabric of my dress. Finally, she gripped my hand, sensing my trepidation, a finger forcing me to stare into her eyes. "Rory, you look amazing."

I beamed, all assortments of weights lifted from my shoulders. "You really think so, Amanda?"

"Amazing! I mean I knew from the pictures you pulled it off well but standing here...I mean fuck me!" I giggled, shutting the door in a panic as it had been open for far too long for my liking. Amanda continued her inspection, spinning me in circles as she laughed, playfully pulling on parts of my uniform. "I can't believe it's you..."

I blushed, a giant smile now stuck to my face as I showed off for my friend, gaining confidence in her reaction. Recovering from both of our shocks, I offered to make her some tea, to which Amanda graciously accepted, never taking her eyes off me as I minced into the kitchen. I sighed happily, once more falling into that headspace I knew and loved, ready for the day as Rory.

We chatted lightly as I worked, mostly Amanda asking questions about my feminine side, still trying to shrug off the slight disbelief in her system. I brought the tea over to my table, setting it down for her as I smoothed out my skirts to sit, legs crossed and hands placed perfectly in my lap like the good girl I truly felt like in that moment. Amanda, however, stared at me with a smirk.

"Rory, don't you have chores to do?" My eyes went wide, giggling.

"I completely forgot! You distracted me!" Amanda laughed, shooing me away, wanting to simply observe my normal routine. My face red, but still smiling like an idiot, I went about continuing my ritual. First step: Laundry. It was also the last step, washing everything I wore today by hand, but the boring boy clothes I wore most of the time were quickly loaded into my machine. With a timer set, I headed to the kitchen.

Amanda for the most part enjoyed the view, sipping her tea and snacking on some options I laid out for her. We kept chatting while I worked, finding it quite nice to have company for once, realising that I enjoyed sharing Rory with others. I whined at her when she had me pose for a few photo's, but didn't protest as I heard the tiny clicks from her phone, my clit aching with excitement being put through the experience.

Eventually I winded down, my chores finished for the day, nearly ready for the final part of my ritual...one I had neglected to share with Amanda. Stripped of my beautiful uniform, in just my stockings and heels, days of denial fueling my imagination and excitement, I had a date with a certain dildo of mine, bouncing on it while I moaned, leading to some of the most powerful orgasms I could ever have. Even thinking about it made my poor clit begin to strain.

However for now I sat with my friend, delaying that exciting finale, thoroughly enjoying her company. Laughing together, Amanda began to blush, looking down as if she had something to say.

"Rory...it's my turn for a confession." I looked at her curiously. "I didn't just come here today because I couldn't believe you were your own maid." I watched as she gained confidence, those eyes locking in on me as she stood, slowly leaning over me in my chair. I couldn't help the tiny whimpers starting to leave my body, feeling that submissive side of myself spring forth, taking control.

Amanda held that pose for a while, a palpable silence between us. Whispering, she continued. "Seeing you in the photos, and even more now..." Her nose tickled mine as our foreheads touched, feeling her breath on my lips, frozen in place as she moved right to my ear. "It made me so fucking wet." I whimpered, feeling my clit strain harder than ever before beneath my petticoats.

Lifting her head back, Amanda stared deep into my eyes once more, planting the tiniest of kisses on my lips. I moaned, barely able to think as we looked at one another, suddenly filled with a desire I didn't know I had for this woman, and her control. She placed a finger on my chest, slowly running it down the length of my dress, until it disappeared underneath the collection of frills to find my clit.

She smirked, cupping the cage in her hands, watching my eyes go wide with fear. "I was hoping you owned one of these." I giggled, blushing so intently I thought my face might burst into flames. Giving my poor balls a squeeze, she pulled out her hand and stood, taking one of my gloved hands in hers. Unable to speak, I simply followed her to the couch, finding myself kneeling between her legs.

With a smirk, Amanda removed her leggings and panties, sitting bare from the waist down in front of me. I couldn't help but whimper, licking my lips as I saw her pussy for the first time, her own excitement evident in how wet and delicious it looked. She brushed a strand of my wig behind an ear, cupping my chin to stare up at her once more.

"Would you like to clean this as well, Rory? After all, it is your fault that it is such a mess at the moment." That forced another giggle out of me, unable to keep the excitement as such a prospect off my face.

"I-I would really like that, Amanda." She smiled, her hand slowly falling away from my chin, inviting me to begin. Running my silky hands up her smooth legs, I eagerly ran my tongue along her pussy, feeling the warmth immediately. Amanda sighed happily, softly groaning as she rested one leg over my shoulder, pulling me even tighter in between her legs. Apparently, I wasn't going anywhere anytime soon.

I loved cunnilingus. Loved it almost as much as sex. The position of it, the moans, hands running through my hair, thighs gripping my face as I worked my tongue and fingers in a variety of ways. However, this was the first time I had done it as Rory, feeling the pretty dress around me, feeling the nylons and garter straps digging into my thighs, and of course the constant aching in my clit as I serviced Amanda. Somehow, it made the experience all the more satisfying.

Soon I had her moaning, back arched as she gripped the couch, offering slight adjustments in what she liked. Finding her sweet spot, I licked and sucked methodically, never faltering as her body twitched and spasmed. I couldn't help but beam with pride as I watched her cum, pushed off her pussy as she quivered above me, one of the most beautiful sights I had ever seen.

Amanda caught her breath though a smile, her leg keeping me in place for the time being. Still in the final throes of her orgasm, she shook and giggled when I teasingly licked her. But once she had regained some sense of control, the look in her eyes let me know I was far from finished being a good girl. Her good girl.

About an hour later we both sat on the couch fully dressed, exhausted from the experience. Amanda placed my head in her lap, lying on the couch and staring up at her while she smiled, once more playing with my wig. "Such a good girl" she cooed, over and over. Beaming, my clit a constant welcomed strain between my legs, I felt as if I could stay like this for the rest of the evening.

Eventually Amanda had to leave, having me walk her to the door. Taking one of my hands, she cupped my chin in the other and stared up at me, locking me in place with those beautiful eyes. "Rory, I know you have a routine you like to follow for your days as a maid. But it's going to have to include me now, because there's simply no way I'm ever letting you do this alone ever again." I blushed, feeling helpless as I stood in place.

"I'm okay with that, Amanda." She smiled, that confidence and control never faltering.

"Good girl. Can you keep that cage on until next Saturday for me?" I whimpered, the thought of wearing it for another entire week made me ache desperately between my legs, but I nodded. Another big smile washed over me as Amanda pulled me down to kiss my cheek. "Goodnight, my sweet Rory. I'll be seeing you soon enough."

I was left standing in my living room, shaking with a feverous need I had never felt before to such an extent, playing through the surprising afternoon I had been put through. But I had one final piece of my own feminine ritual to complete, making my way slowly to the bedroom.

After carefully hanging up my dress, I blushed deeply seeing the state of my panties, knowing I had leaked desperately through most of our encounter. Shakily I slid them down my legs, a strand of pre-cum dangling from my clit, forcing a whimper out of my lips. Taking a finger, I wrapped it around myself, licking it clean as I rolled back my eyes. Moving towards my toy drawer, I was beyond ready for the final part of the day.

My fingers rubbed lube and stretched open my eager little hole, forced into a continuous moan as I felt my clit responding. Rubbing circles along my sensitive g-spot, that familiar ache growing restlessly to cum inside of me, I eventually sank down on the suctioned on dildo, held in place as I began to slowly slide up and down the thick shaft. Legs already quivering, I didn't think I'd last long.

Groaning, the image of Amanda staring down at me while I licked her playing over and over in my mind, I was indeed correct as in less than a minute I was shaking, watching as my clit exploded with cum through my cage. Leaking and dripping everywhere, I whimpered as the dildo rested inside of me, shoved as deep as it could go as I came, reduced to nothing more than a desperate, aching, needy little slut.

I came two more times on my favourite toy, before sliding off of it in necessity before my brain simply ceased to function. Exhausted, starving, and elated, I went about cleaning up my own little finale. My stockings and panties were hung up to dry after being scrubbed, carefully sponging down my dress as well. Stepping out of the shower, I made my way back to the room before stopping, realising Amanda's plan to alter my routine had already begun.

Staring down at my pink clit, the time when I'd normally unlock it for some more traditional fun, I pouted knowing this time was different. Already my clit ached in protest, reading my thoughts perfectly as I slowly put back my keys into the tiny box I kept them in. After cooking dinner and relaxing, I whimpered in bed with the knowledge of my promise, and the consequences of agreeing to her terms.

It was going to be a long, long week.

Sunday morning Amanda messaged me, checking if I was okay. Taking my dramatic response as a yes, she demanded a picture of my cage as it was hidden from her the previous day. I blushed, amazed at how quickly and easily she slid into that position of control. And how...comfortable it felt, still having her as a friend yet wanting to share and explore being Rory in her presence.

We chatted through the week, swapping between friendly chats and slowly ironing out what she and I were comfortable with. Morning cage pictures became the norm, always making her smile seeing me strain and ache desperately. I felt myself constantly being pulled into my feminine persona stuck in the cage, each night dressed up in some manner or another. As I tried to sleep through my excitement on Friday night, for the first time heading into a Saturday I didn't have control over.

I groaned hearing a knock at my door early in the morning, checking my phone to see it was far too early. Clit aching as it often did when I awoke, I threw on some shorts as I stumbled to see who it was. After looking through the peephole my groan deepened, opening the door to an overly excited Amanda. She grinned at me, but was only met by a tired glare.