The Nightshift Sissy

By Max Swan (Horrorotica).

The Nightshift Sissy Max Swan (Horrorotica)

  • Nick works nights because there's no one else around, and he can indulge in his special fetish.
“Nick? Nick, is that you, dude? What the fuck are you doing, man?” Joe said harshly, blinking rapidly at the unexpected sight.

Nick never thought she’d see her muscular boss blush; the man is built like an Adonis. “J-Joe—” Nick began in a high-pitched effeminate tone then coughs to shift her voice back down to her regular male voice. “What are you doing here, Joe?”

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

Nick crosses her ankles, pressing her knees together and still trying in vain to stretch a few more inches of length from the skirt. She brushes her hair back over her ear nervously. “OK. But there’s not, it’s just me. How about we just forget this ever happened, eh?”

Nick smiles hopefully before turning back around to her keyboards, hoping Joe will just go home and they’ll never speak of it again.

“Oh, you’re not getting outta this that easily,” Joe said grabbing the back of Nick’s chair, pulling it out into the aisle and lifting it with one hand, depositing the sissy rather unceremoniously onto the floor.

Nick scrambles to her knees, pulling her skirt down into place. She registers familiar sounds, the clicking, and whirring of Joe’s phone taking a series of high-speed pictures of her. Nikki heard the telltale ‘beep’ of the video recording start as Joe extends a hand out to her.

“Let’s get you on your feet so I can get a good look at you,” Joe said. He steps back as Nick gets to her feet, standing between her and any possible escape. “Turn around, so I can see the back too.” Nick stands there, her hands crossed in front of her skirt, beginning to see where this might be going. Joe glances at her from over his phone. “Do you want these pictures sent to everyone in the company address book? No? Then turn your sissy ass around,” he orders harshly.

Nick chews on her lower lip a little as she turns a slow circle in place, standing very straight to avoid showing off more than she has to. She hears him laugh as she finishes her turn, and then the phone beeps twice as Joe stops one video and starts another.

So, Nikki—it is Nikki, right?” Joe taunts. She nods glumly. “How badly do you want this kept a secret?”

Nikki blushes, her eyes going to Joe’s feet. “W-What do you w-want? I don’t have a lot of money, but I can try to get some together to buy those from you.”

Joe scratches his head and purses his lips before smiling and shrugging. “I get paid well, so keep your money. On your knees, Nikki,” Joe orders.

The moment Nikki feared and dreamed of has come to pass. All the months Nikki had been playing this game, growing her hair so she wouldn’t need wigs anymore. She fantasized about getting caught, and what she’d have to do for silence. Nikki slowly sinks to her knees, settling back on her heels, hands folded in her lap.

Joe’s chuckle sends shivers down her body. “Such an obedient little sissy, are you as slutty as you look? Crawl over here.”

Nikki leans forward, crawling with her ass pushed up and out, trying to be as sexy as she can. As Nikki gets closer to him, she realizes she wanted this to happen, that she’d been working up to this moment. It didn’t lessen the heat of humiliation building in her, but Nikki notices the warmth building lower down. Nikki stops in front of Joe and sits back, looking up at the beefy white man, lifting her chin to show off the small dog collar around her neck, the tag catching the light and reflecting against her shirt, the shadowy word ‘SLUT’ showing in the reflection.

“Well, well, slut, eh, how apt. Now 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.”

Nikki’s lust couldn’t keep her from blushing and whimpering quietly as she unzips his slacks. The bright pink of the polish on her stick-on nails contrasted against the black fabric as Nikki carefully frees Joe’s hardening shaft. Nikki couldn’t stop the soft gasp at the sight of the cock Joe’s clothing hides. It’s almost eight inches long and thick enough that Nikki has to stretch her mouth to get around the head. Nikki uses her hands to slowly stroke Joe in time with pushing as much of his cock down her throat as she can manage. Nikki’s eyes drift closed as the feel of the soft skin slides across her lips, the salty musk of sweat mixing with the waxy tang of lipstick as it clung to Joe’s flesh. Nikki shivers and moans, letting go of Joe’s cock and grasping his hips, pushing his cock deeper into her mouth.

Nikki gags and coughs as the tip of Joe’s cock hit the back of her throat. Nikki doesn’t pull his cock out or stop, but slows, pushing steadily against Joe, easing him deeper into her sissy throat with each stroke. Nikki can feel Joe tense and relax, hear his moans. Each sign of his pleasure stokes the heat of Nikki’s arousal, her tiny three-inch engorged sissy-clit now squeezing against the chastity cage and giving her pain. With a final desperate thrust, Nikki feels her nose buried against the soft curls of Joe’s pubic hair. The sissy’s body shakes in ecstasy as Nikki holds herself there in triumph. Nikki has deep throated this big cock. She slowly backs away until only the tip of her tongue is touching the underside of the head. Nikki gazes at his face and sees him staring back down at her. There’s no malice in Joe’s face, no guile. There’s only lust. Joe knows he saw a potential willing slut and wants nothing more than to use her for sex.

The Nightshift Sissy Max Swan (Horrorotica)

  • Nick works nights because there's no one else around, and he can indulge in his special fetish.

Without warning, Nikki bursts forward, swallowing his length in a single movement. That action is the breaking point. His free hand comes down and pulls her hair into a ponytail at the back of her head, and he uses that grip to begin fucking the sissy’s face, cruelly using her as nothing more than a living fleshlight. Nikki puts her hands behind her back and revels in the abuse. She closes her eyes, moaning around Joe’s cock when she’s able.

Joe suddenly pulls her head back hard, pulling his cock out of her mouth, nearly making Nikki fall back before she can catch herself. Nikki opens her eyes to see Joe stroking his shaft fast and hard right over her face. She opens her mouth wide, waiting, whispering, “Yes—cum—oh, God, yes,” while looking directly into Joe’s camera lens.

The first thick, ropy spurts of white semen spurt over her mouth and lands across her eyes and into her hair. Nikki blinks but keeps them open as Joe milks more of his prize from his balls into her mouth and across her face. She lets it drip over her face and chin, to mix with her spittle as it runs down her neck and makes wet spots on her sheer blouse. The sissy man waits until Joe is done stroking before Nikki raises enough to take his cockhead between her lips and suckles out the last dregs of his cum. When Nikki is sure she’ll get no more, she let go of Joe’s cock and sits back on her heels, waiting. Nikki watches Joe recover himself as he circles her, recording the moment. Then the beefy man gets close making sure to video the semen cooling on her face, mixing with ruined makeup. Joe steps back, still focusing on Nikki.

“Say your name,” Joe orders.

“Nick Thomas,” Nikki said.

“What’s today’s date?”

Nikki glances over at the calendar and clock in her cubicle wall. “It’s Tuesday, July fifteenth, at one-thirty-six in the morning.”

“What did you just do and why?”

Nikki looked directly at the camera and smiles. “I just sucked off Joe Phillip’s cock until he came all over my face and in my mouth.”

“WHY?” Joe insists.

Nikki gulps, her heart beats fast in her chest. This is the moment. “I sucked Joe’s cock so he wouldn’t tell everyone in the office that I’m baby dick sissy slut.

Joe raises an eyebrow because the baby dick confession was unexpected. “Show me,” he said. “Show me that little dicklette, sissy.”


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