Rory's New Job

Story Info
Rory's Mistress finds her a new job, with certain perks.
1.5k words
4.44
6.8k
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
RoryRouge
RoryRouge
596 Followers

Brushing my new wig out of my face, I stared at my reflection. Taking in the bold red covering my lips, dark black accentuating my eyes, and the smoothness of my foundation and blush. Smiling, I could hardly take my eyes off the mirror. I was still nervous beyond belief about what I was about to do, but knowing this was the face I would be doing it with gave me confidence.

Mistress had arranged this new job for me. She wanted to push me, try new experiences in this femme part of my life, as Rory. And what my Mistress wanted...well, she often got. So here I was, dressed as a subtle reminder to a playboy bunny, complete with dark fishnets, cuffs and collar, and matching baby blue uniform. The feeling of the ears on my head kept me in a constant blush, not to mention being more exposed than I had ever felt before.

It wasn't anything special, I was a server for a local club on drag night. But to me, this was a very new step. A very exciting step. As I stepped out of the changing rooms with everyone, my heart was in my throat, clitty already swelling in its cage. My uniform stretched snugly around me, leaving nothing to the imagination. I felt like I was going to blush the entire night! Feet in my 3 inch heels, matching my outfit in baby blue, I began my shaky steps to my first table.

Compliments on my outfit made me blush, thanking them as I took their order. I got through it with a smile on my face, and a growing confidence as I continued on through the night. As I moved from table to table, meeting new people, the nervousness I felt began to waiver, the inner fear of showing Rory to the world slowly receding. I even started to enjoy myself.

On the way back from the kitchen, there was a mirror that I could not pass without staring at my reflection. My hands caressed my outfit, the curves it highlighted, my fishnets encasing my legs. I must have looked at myself every time I passed that mirror, enthralled with what I had been turned into for the evening. It was cut short one trip as my manager shot me a stern glare, which prompted me to pout, focusing more on being a good girl.

As the night went on, patrons were more bold and direct, a result of alcohol I'm sure. The first hand placed on my ass made me jump and blush, receiving a wink from the owner. I finished all the orders and scurried away, not able to look at her in the eye. When I returned with their drinks, she leaned in as if to ask a question, but I knew it was just an excuse to place her hand on my thigh. Expecting it this time, I smiled, and answered, making no move to stop her as she gently gripped my leg.

She took the hint and moved her hand back to my ass, giving it a small squeeze. Blushing and excited, I didn't seem to be able to pull myself away from her, my caged clitty straining and pulsing with need. I stayed still, making sure everyone else at the table had what they needed as I was fondled. My chest reddening, betraying my excitement, my captor simply laughed at my predicament. I was finally released, but not before I was given a few playful smacks.

The rest of the night was less eventful. A hand grazing my thigh here, placed on my ass there, but no one quite as brazen as my earlier patron. That is, until I saw Mistress walk through the door. Of course I figured she would be here, but it still caught me by surprise to see her. She simply winked at me as she was seated with friends, most of which knew about me. All about me. Mistress didn't do secrets very well, especially when it came to bragging about her sissy.

They all cooed when I approached, making me flush once again. Mistress wasted no time in pulling me onto her lap, hands all over my thighs as I tried once again to take the tables order as I was fondled. The women all laughed at my struggling voice and blushing face, teasing me with my Mistress. With a light dismissive smack on my ass, I was released, and went about my job.

For hours, I was tormented by each woman with every trip to the table, enjoying the effect they and working in the club were having on me. While I certainly was having difficulty trying to stay professional, aroused and frustrated at the hands of these wonderful women, I had never had a bigger smile on my face. Being able to express myself in a safe place felt freeing, felt right. I knew that this was something I wanted to be doing.

As we reached closing, and patrons filed out, I was told to bring a drink up to the owner of the club. Picking up a tray, I headed upstairs with the glass of whiskey, carefully ascending the stairs in my heels. Before getting to his office, I was stopped by another mirror, admiring myself. I was in love with my outfit, my look. I was not sure how I was ever going to take it off!

Knocking on the door, I tried to shake that idea out of my mind, entering upon command. I stopped in my tracks as I saw Mistress, casually talking to the owner of the club. Glaring at her, not knowing what she was up to, I walked over to the desk and placed the drink down. She just smiled, asking how my shift went. I told them all that happened, and how much fun I had this evening. They both nodded, glad that I enjoyed it.

Mistress had me pose in the center of the room, hands on my hips. Cheeks reddening, I complied, trying to ignore the stares now directed at me. The owner walked around, taking in my uniform, my legs, my everything. Mistress moved to the front of me, taking my chin in her hand. She asked how much I wanted to work here, how much I wanted to wear this outfit all the time. A tiny moan escaped my lips, as I admitted I wanted it very much, my clit nearly jumping at the though.

Soon I felt his hands exploring my body behind me. Eyes wide, more moans escaping, Mistress asked what I would do to have this job. I tried to answer, to ignore the hands that were currently feeling and pinching my ass, but the only thing that came out was a squeak. Smiling, my Mistress got the answer she was looking for. She gently took my hand, and led me to the couch.

I stood there in excitement, frustration, and anticipation. The owner took a seat in front of me, hand slowly rubbing at his crotch. My eyes immediately drawn, mouth slightly ajar, I could not direct my attention elsewhere. Mistress slowly but firmly forced me to my knees. I looked up at him, rubbing my fishnet legs together in ecstasy, waiting for what I knew would come next.

At his subtle nod, I placed my hands on his crotch. Slowly, with a tiny tremor in my hands, I unzipped his pants. Pulling out his cock, an involuntary gasp was emitted as I took him in my hands. Stroking him a few times, building up my courage, I leaned in kissed the tip of him, before I placed his cock in my mouth. Warm and hard, it slid into me. My tongue acting as a guide, I moved up and down on his cock, a sense of pride shooting through my every time he moaned.

Mistress stood beside me, encouraging, her hands in my hair, on my ass. Moaning, I continued my oral fixation, focusing on my task at hand. Feeling his cock stiffen, I tried to shove it inside of me as far as it would go. Taking my head in both hands he groaned, cumming hard and fast down my throat. Pumping again and again, I felt my mouth get coated as I tried to swallow as quickly as possible. When I was finally released I was gasping for breath, cum still covering my mouth.

Recovering, he tilted my head up, wanting to see me swallow the rest of his cum. I happily obliged, sticking my tongue out to show him what a good girl I was. Mistress was quick to talk again, whispering in my ear. She told me this would be my new nightly occurrence. This was the cost of working here. This is what good sluts did. She said it was my choice, that she wouldn't command it, but I had made up my mind. I knew what I wanted, I knew what I was.

I stared up at the owner, both of the club and the beautiful cock I had just sucked. Not breaking eye contact, I leaned in once more, sealing my new fate with a kiss.

RoryRouge
RoryRouge
596 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
MissLouisecdMissLouisecdover 2 years ago

well this story really stretched my panties

Share this Story

Similar Stories

Rory, the Secretary Rory finds a job as a secretary, with strict conditions.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
The Town Sissy Pt. 01 Rory finds herself at the mercy of the law in Great Oaks.in Transgender & Crossdressers
A Choice Made for You Rory's long awaited night is disturbed beyond imagination!in Transgender & Crossdressers
The Kink Retreat Rory is brought on vacation, unlike any she has ever seen.in Transgender & Crossdressers
More Stories