Night Shift Sissy by Nightside
Experience the tantalizing allure of 'Night Shift Sissy'—a captivating gay erotic sex story that explores desire, identity, and the thrill of nighttime escapades. Dive into an adventure filled with passion and intrigue that will keep you on the edge of your seat. Perfect for fans of LGBTQ+ fiction and erotic storytelling!<br/>
He enjoyed working nights so he could indulge his fantasies. But then he got caught.
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.