Assistant Rory Pt. 01

I had to split this into at least two stories, it seemed to keep adding to itself as I wrote! After all, who hasn't thought about being an assistant of some kind to a dominant person? :P. There's still a lot I want to explore here, so we will see where it goes. I hope you like it!

Meeting Mistress Spires

Work had never been a source of happiness for me. Constantly I bounced between jobs, trying office work, landscaping, construction, sales, and retail. Each one was always the same: mundane, boring, leaving me exhausted at the end of the day. My only reprieve was Rory, getting dolled up whether I was staying at home, doing chores, or going to my favourite bar. It was often the only thing that got me through the day.

It was how I found myself sitting on my regular stool, Friday night and free for a few days. I had rushed home from work earlier, practically leaping into my nylons and form fitting pink dress, my matching heels instantly soothing the stress of the week. Legs crossed, sipping a yummy cocktail through a straw, I simply felt myself unwind. There were few things that brought a smile to my face more, than when I got to bring out Rory in her full glory.

Lost in my own mind, staring out at the crowd that had gathered, I didn't even notice the business woman who snuck up beside me. A gentle hand on my nylons made me flinch, soft but commanding as she held my thigh, no indication it was an accident. Introducing herself as Ms. Spires, I blushed deeply as we started to chat. Her hand continued to grip and squeeze gently while she steered the conversation where she wished. It took all of five minutes for me to be completely wrapped around her finger, that smooth voice seeming to take over my brain. Dominant women I tell you, they just didn't play fair!

After an hour of talking, Ms. Spires whispered in my ear that she'd like to take me home. I was pretty sure my face matched my dress at this point, nodding eagerly as she took my hand. I was led and helped into a black sedan, her hand returning to my thigh for the journey. Such a subtle display of dominance, but that hand seemed to grip me entirely. I fixated on it as we arrived at her condo, soft whimpers escaping my lips as she moved up and down my nylon leg.

Hand on my waist as Ms. Spires led me to the elevator, slipping down to my ass as the door closed. She casually told me how I would be cumming on her fingers and cock very shortly, that cute girls like me were a weakness of hers.What a coincidence, I thought to myself,gorgeous dominant women who called me beautiful and promised to fuck me hard with a strap-on were mine....

I quickly found myself in my stockings and garter, panties and dress stolen from me as soon as the door closed. Blushing, I tried to hide my caged clit with my hands, but that too was denied to me as she pinned them above my head. Eyes staring me down, she held me still with one hand, the other exploring her new toy. My legs shook as she cupped and held my clit, moaning and whimpering like a little whore. Through it all those beautiful eyes bore into me, watching as I slipped further into subspace. Further into Rory.

Turned around, palms flat on the wall, I waited while she disappeared, returning with toys. A large plug was shoved gently inside of me, rocked back and forth until my slutty asshole devoured it. Hands cuffed behind me, Ms. Spires pushed me down to my knees in front of her. I moaned into her crotch as she pressed her panties against me, so desperate to serve this amazing woman. This Goddess. My clit ached in its prison, anxiously awaiting the promised fuck.

Staring into my eyes, solidifying her control over the evening, I felt her collar clipped around my neck, the familiar tug of a leash pulling me along. Wasting no time, she threw me onto the bed, squeaking as I had no hands to catch myself with, falling face first into the mattress. I felt Ms. Spires take off my heels, her hands running up and down my legs, forcing my head back down and my ass nice and high. Muffled moans met her touch, as she continued to explore my body, curious hands back to fondling my aching little clit.

Gripping my balls, pushing on my plug, squeezing my thighs, my mind simply melted under her control. This was exactly what I needed to take my mind off of work, to let go and enjoy Rory. I had no thought in my head other than her words, her whispers, her demands. Ms. Spires owned me completely, through and through, my only desire to do her bidding, to be her good girl.

I was flipped over, blushing as my clit was fully on display, Ms. Spires smiling at how much I leaked with anticipation. A few pillows propped me up for her, watching as she strapped on the most beautiful cock I had seen in a while. Whimpering, I eagerly placed my legs on her shoulders as she replaced the plug inside of my ass with her cock. Slowly at first, drinking in the expressions on my face, she pushed in and out of her little slut for the evening. But soon, I moaned like a whore as she fucked my ass hard.

It felt like I came immediately, the pent up need inside of me from the week unable to contain itself. Leaking and spurting out of my cage, I softly whimpered through my orgasm, her cock never slowing as she called me a good girl. Strong hands gripping my waist, her thrusts continued, Ms. Spires feeling the cock rub against her clit, pushing hard for her own release.

I'm ashamed to say, but I came three more times before hearing her scream in ecstasy, gripping my hips hard as she pushed deep inside of me, orgasm shivering through her body. Both exhausted, Ms. Spires collapsed on top of me, spent and smiling. We giggled together as she kissed my neck, running her hands through my wig. Squeezing me tight, she thanked me for being her good girl, as if she was the one who should be doing the thanking! I still could barely think with her cock inside of me, mumbling how happy I was in that moment.

Ms. Spires led me to the bathroom, deviously leaving my cuffs on while she cleaned me of our evening fun. I found myself pushed against the shower wall as she pressed into my tongue, barely able to breathe as she came a second time, hands running through my real hair, calling me cute. Keeping me bound seemed to amuse her, left in that state while she cleaned off our make-up, returning to bed. My plug was replaced, and hands re-cuffed to the headboard above me. Stretched out, immobilised, Ms. Spires fell asleep with me in her arms, hand once again returning to my caged clit.

I groaned as I woke up, torn between happiness being in her arms, and the aching strain in my clit. Mornings were always the hardest, never wearing my cage long enough for my clit to get used to them, angrily protesting at the treatment I was putting it through. Ms. Spires seemed to enjoy my torment though, teasingly rubbing my stretched balls as she bit and whispered into my ear. I could do nothing but whimper, my keys still at my apartment, my hands stolen from me.

Ms. Spires replaced my make-up in her own image, blushing as she turned me back into a beautiful girl. Given a bathrobe for breakfast, we talked over some coffee and food, learning about one another. I felt so at ease as she listened, feeling as if I'd known her for years. She returned to the bedroom to tidy up from our evening while I cleaned the kitchen. Twice my chore was hindered by her sneaking back to spank and tease me, a mischievous smile on her face each time.

Dressed in my outfit from the night before, soon I said goodbye at her door, my number in her phone asMy Good Girl Rory. I rolled my eyes as she typed it in, but blushed the entire walk home as I repeated it in my mind. I could still feel her lips on my cheek from her kiss goodbye, already wanting to see her again.

The next weekend I got my wish, showing up in my latex skirt and lace top. I had never worn this in public before, but after our last meeting I wanted to impress her. Ms. Spires was certainly impressed, a big smile greeting me at the door, having me twirl back and forth so she could admire my outfit. I blushed through her compliments, soon moaning in her arms once more as that big cock tore orgasms out of me.

The following Friday I got home exhausted, depressed from work. I apologised to Ms. Spires, explaining what happened and how I didn't think I'd be very good company. She told me to put on something casual and meet her for drinks, chat through some of the things I was dealing with. After some insistence she convinced me, moping slightly as I made my way to the café between us.

Ms. Spires took my hand in hers as she sat down, listening as I vented. How every job just didn't ever seem to fit, leaving me drained, spent, and unfulfilled. She asked the odd question but mostly just let me talk, concern on her face over the new person in her life. I appreciated her comforting greatly, still feeling depressed but a bit better than hours before, happy that she talked me into coming out to meet her.

Her concern slowly turned to excitement, that glint in her eye I had seen many times in our two previous meetings. Grabbing my attention, she held me there with her energy.

"Rory, what if you came and worked for me?" I stared back at the wide eyes waiting for my response, slightly taken back by the turn of events.

"Doing what? I don't even know what it is you do?" I asked, curious, still sort of feeling this was a ploy to cheer me up.

"I run a photography studio, renting out space for people to do shoots in. But I am looking for an office assistant, someone to help out with day to day activities and scheduling. What do you say?" Ms. Spires gripped my hand firmer, as if trying to transfer her excitement through them to me.

"But you don't even know if I'm qualified!" I muttered.

"Nonsense. You're smart, organised, well spoken. And I know for a fact you enjoy being told what to do..." Smirking, she laughed at the blush that brought over me, unable to match her stare.

"It does sound a lot more fun than my current job. But what if I'm bad at it? You won't want to see me anymore." I pouted, concerned about the fallback of such a venture. After all, I didn't exactly have the best track record when it came to jobs.

"Rory, honey. I am a very dedicated person, and take my job very seriously. Trust me when I say that you can do this, I will be with you every step of the way helping where I can." Those kind eyes softened my resolve even further, unable to say no to such a comforting face. "Besides," she smirked, "training you will be fun!"

We talked back and forth about what it would entail, money, expectations, etc. Mainly it did sound like a job I was capable of, and working with Ms. Spires would be so wonderful, having someone I could lean on and learn from.

"There are a few rules that come with the position, I'm afraid" she said, my heart sinking. I figured this would be where it all fell apart.

"One. You will call me Ms. Spires at work, always. Some there call me Amanda but that privilege does not extend to you, young lady. Do I make myself clear?" Blushing, liking being called that by her, I nodded that it was something I would do. "Good girl."

"Two. I will be taking the keys to your cage. Ah-ah!" she tutted, seeing me start to protest. "No exceptions! You have told me many times losing control of that cute little clit of yours is something that you have always wanted, and it is something I want too. It helps you focus, and makes you a better girl for me." I pouted, shooting her a glare, but I knew she was right. It was something I wanted, had wanted for a long time, and enjoyed in my life. I let out a dramatic sigh, agreeing to her second term with a sliver of fear coursing through me.

"Oh, and in private you will call me Mistress." I growled, seeing the laughter and excitement dancing in her eyes.

"Okay fine, I agree." I huffed, her eyes narrowing in on me.

"Okay fine, you agree...what?" I blushed, that controlling stare melting the sass inside of me.

"I agree, Mistress." That word had so much excitement behind it, I could barely get it passed my lips. But Ms. Spires, now my Mistress, smiled at hearing it, the dynamic between us solidifying in that moment.

"Finally, my dear Rory, number three." Once again, that mischievous stare as she smiled at me. "You see, I am hiring Rory as my assistant. The cute, blushing girl I met three weeks ago. So..."

My eyes widened with realisation of what she meant. "No..."

"Yes."

"No."

"Yesssss."

"No!"

Mistress Spires smiled, silently sitting and staring while I protested. I complained that I couldn't, that I wouldn't be able to do my job. How could I get there? I wasn't always in the mood to be Rory! I didn't have enough clothes for it, never mind appropriate ones! Through it all she just smiled, sipping her tea, watching me ramble on back and forth.

Seeing my arguments fall on deaf ears, I pouted. "Do I have to, Mistress?"

Once again taking my hand, she gripped tightly as she smiled. "Yes, my good girl. You thrive when you are Rory, I've seen it in your face. You can always change when you get home, but we both know that you have far more fun when you get to be dolled up." Squeezing my hand, Mistress Spires watched as I blushed at her words, knowing the truth in them.

"To make it less scary, we will do a trial run, to see if this is something you can handle and want."

"For how long?" I asked.

"Hmmmm, let's say a month."

"A month!!?" I gasped, that was far too long! But Mistress nodded, considering the matter settled. Again my protests were ignored, returned only with a stern stare that reduced me to worried mumbling. She stood up, kissing me on the cheek to seal the deal.

"I will see you tomorrow morning, we are going shopping to help with your wardrobe. One month, Rory. No less. I promise that after being my good girl for that long, you will want for nothing else." Holding my chin, staring down into my eyes, her warm smile spread through me, giving me enough confidence to nod. I watched her walk away, sitting in the café, my mind a mix of emotion as to what I had just agreed to.

Could I really work as Rory? I mean for part of me it was a dream come true, something I had sought after my entire life. But could I actually do it? Be the good girl Mistress wished me to be? My clit ached in its cage, excitement getting the better of me from the evening, almost forgetting I had signed over the keys to it as well. As I made my way home, another thought ran through my head.

Wait, did she say shopping!?

Rory's First Day

True to her word, Mistress knocked on my door early in the morning. I was in the middle of breakfast, still wondering if last night had been a dream. But as the bossy woman who was now my keyholder shoved me into the bathroom to get ready, it was abundantly clear that it had been, in fact, real.

I came out, face made up and wig in place, to Mistress laying out my attire for the day. I took a deep breath realising this was going to happen, stepping into the tan stockings and garter. She slid some silk panties up my legs, sending shivers through my as they comfortably hugged my clit, starting to strain from being dressed. My breast forms held in place by my bra, Mistress smiled, taking pictures for my first day as her official good girl.

She even made me formally hand over my keys, blushing on my knees as I happily did so, only slightly panicking as I saw them disappear into her purse. She stood me up, sliding a loose pink skirt up my legs, perfectly hiding my clit. Finding heels closely matching, I soon was teetering five inches off the ground, clicking around my apartment as I twirled. I felt myself start to relax, giggling as I enjoyed being girly. Being Rory.

Mistress Spires finished my look with a floral black top, shoulders exposed, just hiding my bra straps. Happy with my look, we almost made it out the door before I heard her squeal, seeing a pink heart collar in my collection. Groaning, I quickly lost in my protest as it was fitted to my neck, "it matched my skirt and heels too perfectly not to wear," her reasoning. Glaring at my Mistress, she returned my sass with a smile, lifting up my skirt to spank me hard enough to force out a squeak, as I found myself ushered out of the apartment.

As much as I was nervous approaching our first stop, a large part of me was also excited. After all, whether you're a casual crossdresser, a sissy, or a full-time girl...who hasn't thought about being a cute secretary or assistant? Images of tight skirts, colourful blouses, cute heels, and seamed stockings danced through my head. I wondered just how alluring Mistress planned on making me look for work.

As it turned out, the answer to that was...right on the line of inappropriate. Each skirt, each top or blouse, and each pair of heels seemed to push the limit, leaving nothing to the imagination. I spent the morning twirling, walking back and forth, and a lot of glaring at my Mistress, who just ignored me while bringing new things to try on. By lunch I was set with an array of business attire which Mistress had catalogued on her phone, saying I would simply receive pictures each morning on what to wear.Great....

After lunch Mistress insisted on extending my lingerie and panties collection, as I burned with humiliation while I was sized. The salesperson was very nice and patient, giggling as Mistress commented on everything, watching me blush. Bodysuits, thongs that actually held my clitty in place, panties hugging my ass perfectly, and more nylon than I knew what to do with. Not to mention a selection of bras, since one was required every day. That was something I'd have to get used to!

Our final stop of the day surprised me, a little salon on the outskirts of the city. Inside I teared up, nearly crying, seeing a new wig Mistress had ordered for me. I sat still and was a good girl while they told me how to maintain it, listening intently as it was styled on my head. Long, black, and sleek, I felt so pretty every time I caught a glimpse in the mirror. I couldn't help but hug Mistress Spires tightly, so happy to be her good girl. She had gone through so much trouble for me, I didn't know how I'd ever thank her.

That night I certainly tried to, grinding on her cock, sitting in her lap while she played with my new wig. I moaned, moving up and down, pushing into her how she liked, knowing it rubbed her clit just the right way. I must've been getting better, only cumming twice before I saw the orgasm wash over her, leaning against her chest with exhaustion and glee. Seeing her good girl all day had worked my Mistress into a frenzy it seemed, stealing two more orgasms from my tongue, and forcing many more out of me as she took me hard from behind.

Sunday I collapsed on my couch, still exhausted, knowing tomorrow was my first day. It had been an exhausting, emotional, and overwhelming weekend, my mind still racing as to what tomorrow would entail. Even though Mistress had fucked countless orgasms out of me, my poor clit ached and strained at the thought of walking into her office as Rory. Classic black pencil skirt, black seamed tan stockings, so smooth on my legs when I tried it all on for her. White blouse, ruffled and pretty, four inch heels pushing everything into place. And of course, my new wig. I could barely contain my excitement seeing the final product in the mirror, Mistress' proud smile behind me as I giggled at my reflection.

Monday morning rolled around quickly, whimpering in bed as my clit strained hard in my tiny little cage, eager to start the day. I couldn't shake how different it felt, losing control of my keys, that constant ache between my legs reminding me of my Mistress' tightening grip over Rory. I had to smile, knowing how much I enjoyed the ache, the need building inside of me. Being controlled by such a wonderful person was exactly what I needed. What I wanted. And today, I got to show her how excited I was to be her good girl, and assistant!