Night Shift Sissy

I could never understand why my coworkers always balked at working nights. Every shift I took, I got more done in a few hours than I ever did while trying to concentrate with the distractions of the full office going about their own business. It also allowed me to indulge the fetishes that I did my best to keep secret. I would leave the house dressed in my sluttiest outfits and make up, my cock locked up in the smallest chastity device I could find, and enjoy wandering through the twenty-story office building, the echoes of my stilletos clicking against the tile floors loud in the silence. I would take the elevator from the garage up to my department’s floor, bypassing the security desk completely, and sit at my desk working through pages and pages of coding in blissful piece.

I did not hear the elevator open, or the security door open with the normally loud “clack”. So absorbed in my work was I that my first indication that I was not alone that night was hearing Dwayne say, “What the fuck?” as he turned the corner into my cube. I spun in my chair to face him, my face showing the obvious shock at being discovered. I watched Dwayne’s eyes as he took in the outfit I’d chosen for tonight: a light, peach blouse over a bright pink bras, filled out with my water-filled falsies; my black pleated skirt that fell mid-thigh when I was standing, and rode up to show the pink thong panties that matched my bras and the tops of my black garter stockings. I closed my legs quickly, my left hand moving to pull the skirt down while my right arm went across my chest.

“Chris? What the fuck are you doing?” Dwayne whispered loudly. I would never have thought that I would see a black man blush, let alone one as muscular as he was.

“D… Dwayne…” I coughed to shift my voice down from the high effeminate one I used when dressed like this to my normal tone. “What are you doing here?”

“Security called me. Said there was a woman in the building using your security credentials. He thought she… you… had stolen them and someone was trying to hack our systems. You’re lucky that we have so many contractors on payroll right now, or I’d have called the police instead of coming in myself.”

I crossed my ankles, pressing my knees together and still trying in vain to stretch a few more inches of length from the skirt. I brushed my hair back over my ear nervously. “Ok. So, now you know there is not someone who doesn’t belong here. Now you can go home and we can forget this ever happened.” I smiled up hopefully before turning back around to my keyboards.

“Oh, no you don’t.” Dwayne grabbed the back of my chair, pulling it out into the aisle and lifting it with one hand, depositing me rather unceremoniously on my ass on the floor. I scrambled up to my knees, pulling my skirt back down into place. I registered the sounds I was hearing, the clicking and whirring of Dwayne’s phone taking a series of high-speed picutres of me. I heard the tell tale “beep” of the video recording start as he extended a hand out to me. “Let’s get you on your feet so I can get a good look at you.” He stepped back as I got to my feet, keeping himself between me and any escape. “Turn around, so I can see the back too.” I stood there, my hands crossed in front of my skirt, beginning to see where this might be going. He looked at me from over his phone. “Do you want this sent to everyone in the company address book? No? Then turn your sissy ass around,” he ordered. I chewed on my lower lip a little as I turned a slow circle in place, standing very straight to avoid showing off more than I had to.

I heard him laugh as I finished my turn, then his phone beep twice as he stopped one video and started another. “So, Chrissy,” he taunted, “How badly do you want this kept secret?”

I blushed, my eyes going to his feet. “Wh.. what do you want? I don’t have alot of money, but I can try to get some together to buy those from you.”

Dwayne made a show of thinking before smiling and shaking his head. “I get paid plenty, so you can keep your money. On your knees, Chrissy,” he ordered.

The moment I feared and dreamed of had come. All the months I had been playing this game, growing my hair out so I wouldn’t need wigs anymore, I fantasized about getting caught, and what I would have to do for their silence. I slowly sunk to my knees, settling back on my heels, hands folded in my lap.

His chuckle sent shivers down my body. “Such an obedient little sissy all of the sudden. Are you as slutty as you look? Crawl over here.” I leaned forward, crawling with my ass pushed up and out, trying to be as sexy as I could be. As I got closer to him, I realized that I had wanted this to happen, that I had been working myself up for this moment. It didn’t lessen the heat of humiliation that was building in me, but I noticed a different warmth starting to build lower down. I stopped in front of Dwayne and sat back, looking up at him, lifting my chin to show off the small dog collar around my neck, the tag catching the light and reflecting against his shirt, the shadowy word “SLUT” showing in the reflection.

“Well, slut. Pull it out and start sucking. If you’re good at it, you might not have to do it for a living after I turn these into HR.”

Even my lust couldn’t keep me from blushing and whimpering quietly as I reached up to unzip his slacks. The bright pink of the polish on my stick-on nails contrasted against the black fabric as I carefully reached in to free his hardening shaft. I couldn’t stop the soft gasp at the sight of the tool his clothing hid. It was almost as long as my forearm, and thick enough that I had to stretch my mouth to get around the head. I used both hands to slowly stroke him in time with pushing as much of him into my throat as I could manage. My eyes drifted closed as the feel of the soft skin slid across my lips, the salty musk of his sweat mixing with the waxy tang of my lipstick as it clung to his flesh. I shivered and moaned, letting go of his cock and grasping his hips, pushing him deeper into my mouth.

I gagged and coughed as the tip of his cock hit the back of my throat. I didn’t pull him out or stop, but I slowed down, pushing steadily against him, easing him deeper into my throat with each stroke. I could feel him tense and relax, hear his moans. Each sign of his pleasure stoked the heat of mine. With a final desperate thrust, I felt my nose bury against the soft curls of his pubic hair. My body shook in ecstasy as I held myself there in triumph. I had deep throated this monster! I slowly backed away until only the tip of my tongue was touching the underside of his head. I looked up at his face and saw him looking back down at me. There was no malice in his face, no guile. There was only lust. I knew he saw a willing slut and wanted nothing more than to use it.

Without warning, I burst forward, swallowing his length in a single movement. That action was the breaking point. His free hand came down and pulled my hair up into a ponytail at the back of my head, and he used that grip to begin fucking my face, bestially, cruelly, using me as nothing more than a toy. I pulled my hands behind my back and reveled in the abuse. I closed my eyes, moaning around his cock when I could.

He pulled by head back hard, pulling his cock out of my mouth, nearly making me fall back before I could catch myself. I opened my eyes to see him stroking his shaft fast and hard right over my face. I opened my mouth wide, waiting, whispering, “yes… cum… yes…” while looking directly into his camera lens. The first, thick, ropy spurts of his semen shot over my mouth and landed across my eyes and into my hair. I blinked, but kept them open as he milked more of my prize from his balls into my mouth and across my face. I let it drip down my face, my chin, mix with my spittle as it ran down my neck and made wet spots on my sheer blouse. I waited until he was done stroking before I raised up enough to take his cock head between my lips and suckled out the last dregs of his seed. Once I was sure I would not get more, I let go of him and sat back on my heels, waiting.

I watched him recover himself as he circled me, recording the moment. Then he got close to make sure he caught the jizz that was cooling on my face, mixing with my ruined makeup. He stepped back, still focusing on me.

“Say your name.”

“Christopher Davies.”

“What is today’s date?”

I looked over at the calendar and clock on my cube wall. “It’s Wednesday, August ninth, at two forty five in the morning.”

“What did you just do and why?”

I looked directly at the camera and smiled. “I just sucked Dwayne Maxwell’s cock until he came all over my face and in my mouth so he would not tell everyone in the office that I am a sissy slut.”

Dwayne stopped the recording and put his phone away, smiling at me. He walked closer, bending down so his face was close to mine. “That’s a good little slut. Now, you come dressed like the sissy whore you are every night from now on. I might come in and use you, or I might not. If I find out you don’t dress properly, or you decide that you don’t like my cock in your mouth or your ass, then I send the videos and pictures to everyone in the company, post them on the internet with your name and phone number, and make sure everyone knows what you are. Understand?”

I nodded, the idea of the humiliation he promised both thrilling and terrifying. He patted me on the head and started walking toward the doors, putting away his schlong as he called over his shoulder, “Oh, and I’ll tell the security guard about our arrangement. I’m sure he’ll want a turn at your sissy ass, too, for his silence. Good night, Chrissy.”

I just sat there on my knees for a few moments, processing what had happened, and what was going to happen. I slowly got to my feet, collected my purse from my cube, and went to the restroom to fix my makeup. My first look in the mirror was almost enough to make me cum. My lipstick was smeared all over my mouth and chin, my mascara as running down my cheeks, and I had drying cum on my face, in my hair, and on my shirt. I looked and felt dirty, slutty, used, and completely satisfied. I smiled at the slut in the mirror and went back to my desk without fixing anything. I just finished out the shift, logged off, and went home, waving at the security guard as I walked through the lobby.

As ordered, I came into work the next night in full slutty “Chrissy” mode. I stopped at the security desk and talked with the guard, letting him know that I had a couple high priority jobs to get done, but if he waiting until about three, I’d be happy to pay for his silence. He grinned and said he was looking forward to it.

As I got to my desk, I received a shock. There were two envelopes on my keyboards. I opened the first to find a letter of termination. Dwayne had talked to our manager and shown him the files, and I was fired for inappropriate conduct. There was a severance check for the amount of half a year of my salary, and a reference letter that stated I had been let go due to over-staffing. I was crushed. Dwayne had betrayed me. Oddly, that bothered me less than not being able to continue our games.

With a sigh, I opened the second envelope. As I pulled out the paperwork, it took a good thirty seconds for me to actually understand what I was reading. It was a contract for “Christina Davies” to work as a consultant for the position I had just be fired from, at a higher salary, with a better benefits package. The only requirement was that she- or I- had to agree to work night shift exclusively, aside from having to appear in person to sign the contracts with the manager. I giggled and danced around the office for a few minutes before I grabbed a few boxes and emptied my work-space. After all, “Christina” would have to bring her stuff in with her in the morning, and “Christopher” had just been fired.

As I stepped out of the elevator, singing quietly to myself, the guard looked at me questioningly. I told him what Dwayne had done for me, and he laughed. I set my boxes down by the desk and offered him a quick blowjob under his desk “for old times’ sake”. He laughed again, with a “not tonight”, but helped me take my boxes to the car.

“It’s only polite to help a lady,” he said with a chuckle.

I kissed him on the cheek and drove home, excited to start my new job. “I’ll have to do some shopping tomorrow after I get my new hire processing done. I’ll need some actual business attire,” I giggled.