The Nightshift Sissy
By Max Swan.
Then she sat at her desk, working through pages and pages of coding in blissful peace. Nikki got away with this for quite a while, as her supervisor rarely came to her floor. Her supervisor, Joe Walsh, would mostly call from his office on a lower floor to discuss work matters. She felt a real freedom now and reveled in the feeling of her dangerous game.
Then, one night, Nikki didn’t hear the elevator open or the security door with its ordinarily loud clack. So absorbed in work is the trans-woman that her first indication she was not alone was when her supervisor Joe said, “What the fuck?”
Nikki spins in her chair to face the intruder, her eyes bulging and mouth hanging open in silent shock. She watched Joe’s eyes as the big, beefy man took in Nikki’s outfit for tonight. A white (almost see-through) blouse over a bright pink bra, filled out with her water-filled falsies. Her black skirt fell mid-thigh when Nikki stood and rode up to show the pink thong panties matching her bra and the tops of her black garter stockings. Nikki closed her legs quickly, her left hand moving to pull the skirt down while her right arm went across her chest.
“Nick? Nick, is that you, dude? What the fuck are you doing, man?” Joe said harshly, blinking rapidly at the unexpected sight.
Nikki never thought she’d see her muscular boss blush. The man’s built like an Adonis. “J-Joe…” Nikki began in a high-pitched effeminate tone, then coughed 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.”
Nikki crossed her ankles, pressing her knees together and still trying in vain to stretch a few more inches of length from the skirt. Nikki brushed her hair back over her ear nervously. “OK. But there’s not. It’s just me. How about we forget this ever happened, eh?”
Nikki smiled hopefully before returning to her keyboard, hoping Joe would go home and they’d never speak of it again.
“Oh, you’re not getting outta this so easily,” Joe said, grabbing Nikki’s chair.
The man pulled it out into the aisle. He lifted it with one hand, depositing the sissy rather unceremoniously onto the floor. Nikki scrambled to her knees, pulling her skirt down into place. She registered 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 extended her hand.
“Let’s got you on your feet so I can get a good look at you,” Joe said.
He stepped back as Nikki got to her feet, standing between her and any possible escape.
“Turn around so I can see the back too.”
Nikki stood there, her hands crossed in front of her skirt, beginning to see where this might be going. Joe glanced 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 ordered harshly.
Nikki chewed on her lower lip as she turned a slow circle in place, standing straight to avoid showing off more than she must. Nikki heard him laugh as she finished her turn, and then the phone beeped twice as Joe stopped one video and started another.
“So, Nikki—it is Nikki, right?” Joe taunted.
She nodded glumly.
“How badly do you want this kept a secret?”
Nikki blushed, her eyes going to Joe’s feet. “W-What do you w-want? I don’t have much money, but I can try to get some together to buy those from you.”
Joe scratched his head and pursed his lips before smiling and shrugging. “I got paid well, so keep your money. On your knees, Nikki,” Joe ordered.
The moment Nikki feared and dreamed of had come to pass. All the months she had been playing this game, growing her hair so she wouldn’t need wigs anymore. She fantasized about someone catching her and what she’d have to do for silence. Nikki slowly sunk to her knees, settling back on her heels, hands folded in her lap.
Joe’s chuckle sent shivers down her body. “Such an obedient little sissy. Are you as slutty as you look? Crawl over here.”
Nikki leaned forward, crawling with her ass pushed up and out, trying to be as sexy as possible. As Nikki got closer to him, she realized she wanted this to happen, that she’d been working up to this moment. It didn’t lessen the heat of humiliation in her, but Nikki noticed the warmth building lower down. Nikki stopped before Joe and sat back, looking up at the beefy white man, lifting her chin to show off the small dog collar around her neck. The tag catches the light and reflects 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. Especially if I have to turn these in to HR.”
Nikki’s lust couldn’t keep her from blushing and whimpering quietly as she unzipped his slacks. The bright pink of the polish on her stick-on nails contrasted against the black fabric as Nikki carefully freed 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 must stretch her mouth to get around the head. Nikki used her hands to slowly stroke Joe in time, pushing as much of his cock down her throat as she could manage. Nikki’s eyes drifted closed as the feel of the soft skin slid across her lips, the salty musk of sweat mixing with the waxy tang of lipstick as it clung to Joe’s flesh. Nikki shivered and moaned, letting go of Joe’s cock and grasping his hips, pushing his cock deeper into her mouth.
Nikki gagged and coughed as the tip of Joe’s cock hit the back of her throat. Nikki didn’t pull his cock out or stop but slowed, pushing steadily against Joe, easing him deeper into her sissy throat with each stroke. Nikki could feel Joe tense and relax, hearing his moaning. Each sign of his pleasure stoked the heat of Nikki’s arousal. Her tiny three-inch engorged sissy-clit was now squeezing against the chastity cage and giving her pain. With a final desperate thrust, Nikki felt her nose buried against the soft curls of Joe’s pubic hair. The sissy’s body shook in ecstasy as Nikki held herself in triumph. Nikki had deep-throated this big eight-inch cock. She slowly backed away until only the tip of her tongue touched the underside of the head. Nikki gazed at his face and saw him staring back down at her. There was no malice in Joe’s face, no guile. There was only lust. Joe knew he saw a potential willing slut and wanted nothing more than to use her for sex.
Without warning, Nikki burst forward, swallowing his length in a single movement. That action was the breaking point. His free hand came down, pulling her hair into a ponytail at the back of her head. He used that grip to begin fucking the sissy’s face, cruelly using her as nothing more than a living fleshlight. Nikki put her hands behind her back and reveled in the abuse. She closed her eyes, moaning around Joe’s cock when she could.
Joe suddenly pulled her head back hard, pulling his cock out of her mouth, nearly making Nikki fall back before she could catch herself. Nikki opened her eyes to see Joe stroking his shaft fast and hard over her face. She opened 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 land across her eyes and into her hair. Nikki blinked but kept them open as Joe milked more of his prized jizz from his balls into her mouth and across her face. She let it drip over her face and chin to mix with her saliva as it ran down her neck and made wet spots on her sheer blouse. The sissy man waited until Joe was done stroking before Nikki raised enough to take his cockhead between her lips and suckle out the last dregs of his cum. When Nikki was sure she’d get no more, she let go of Joe’s cock and sat back on her heels, waiting. Nikki watched Joe recover himself as he circled her, recording the moment. Then the beefy man got close, videoing the semen cooling on her face, mixing with ruined makeup. Joe stepped back, still focusing on Nikki.
“Say your name,” Joe ordered.
“Nick Thomas,” Nikki said.
“What’s today’s date?”
Nikki glanced over at the calendar and clock on her cubicle wall. “Tuesday, July fifteenth, at one-thirty-six in the morning.”
“What did you just do, and why?”
Nikki looked directly at the camera and smiled. “I just sucked off Joe Phillip’s cock until he came all over my face and mouth.”
“WHY?” Joe insists.
Nikki gulped, her heart beating fast in her chest. This was the moment. “I sucked Joe’s cock so he wouldn’t tell everyone in the office that I’m babydick sissy slut.
Joe raised an eyebrow because the baby dick confession was unexpected. “Show me,” he said. “Show me that little dicklette, sissy.”
Nikki lifted her skirt and pulled her pink panties aside to reveal the transparent plastic chastity cage. Joe moved the camera close to film it all.
Joe chuckled. “You do have a babydick,” he said coldly. Nikki blushed. “Now it all made sense. Who has the key to that cage?”
“I do,” Nikki whispered.
Joe stopped the recording, smiling at Nikki and putting away his phone. He helped Nikki get to her feet. “That’s a good babydick slut,” he said, “but I think that key now belongs to me. Hand it over.” Nikki stumbled a little at first as she went to her cubicle and rummaged in her purse for a moment, pulling out a key chain with two small keys on it and handing it to Joe. “Are these all the keys?” Joe asked.
“Yes,” Nikki said, dropping her head.
“Hmm, just to be sure, I’ll replace the lock next time,” Joe said. “I don’t want you playing with your clit without my permission. Got it?”
“Yes, sir,” Nikki said softly.
“I expect to see you dressed like this from now on, too,” Joe continued. “If you don’t, I’ll send these videos and pictures to everyone in the company. I’ll post them on the internet with your name and phone number and make sure everyone knows what you are. Understand?”
“Will I see you, sir?” Nikki asked, hopefully.
“I might come in and use you, I might not,” Joe said dismissively.
Nikki nodded. The idea of the humiliation Joe promised was both thrilling and terrifying. Joe patted her head and started walking toward the doors putting away his cock. He said, “I’ll tell the security guards about our arrangement. I’m sure they’ll want a turn at your sissy pussy, too. For their silence, of course. Good night, Nikki.”
Nikki stood silent momentarily, processing what had happened and what would happen. She then went to the restroom to fix her makeup. Her first look in the mirror was almost enough to make the sissy orgasm. Her makeup was so smeared that Nikki looked like a crazy clown. There was the drying jizz that seemed to be all over her. Nikki looks and feels dirty, slutty, used, and completely satisfied. She smiled at the sissy slut in the mirror and returned to her desk without fixing anything. The sissy just finished the shift, logged off, and went home, waving at the security guard as she walked through the lobby.
As ordered, Nick entered work the next night in full slutty ‘Nikki’ mode. She stopped at the security desk and talked with the black man. “Hi, Graham, how’s your night going?” Nikki asked in her effeminate voice, batting her eyelids flirtatiously.
“Oh, hey, err, Nikki,” the black man said, getting to his feet and looking her over. “Joe was right. You are a damn fine piece of ass. I look forward to testing it out tonight.”
Nikki pouted. “I have a big job to finish before I can give myself fully to you. Is it OK if we meet around three?” she asked.
“Sure, but first things first,” Graham said. “Joe asked me to change your lock.” He holds up a new padlock with keys hanging off it. “He didn’t want you playing with your clit without permission.”
“Who’ll have the keys?” Nikki asked, blushing.
“Joe will keep one, and we’ll keep one here for our use,” Graham said, smiling. “Now, raise that skirt and show me.”
“Here, in reception?”
Graham nodded, his grin getting more prominent. Nikki sighed and lifted her red skirt to reveal black g-string panties with a visible bulge in the front. “Take those panties off. You don’t need to wear them here,” Graham said hotly.
She sighed, dropped her skirt, pulled her panties down, took them off, placed them on the desk, and lifted her skirt again to show Graham her caged dicklette in the middle of the building’s lobby.
“Dang, girl, that’s the smallest white boy dick I ever saw,” Graham said, laughing.
He moved around the desk and pulled out the keys Nikki gave Joe last night. The big black man released the lock and pulled the cage off.
“It’s barely a nub soft,” he said, fondling the tiny dicklette. “How big is it hard?”
“Three inches, sir,” Nikki said and blushed.
Graham laughed. “I like how you keep it all bald and shaved. It made it look like a toddler’s dick.”
“Thank you, sir,” Nikki said, her face red.
Graham put the cage back on, set the new lock, and snapped it shut.
“There ya go, Nikki, that’s better now, right?”
“Yes, sir,” she said.
“I’ll see you later tonight,” Graham said, “I can’t wait to fuck that pussy of yours.”
As Nikki got to her desk, there were two envelopes on it. Nikki opened the first to find a letter of termination. Joe had talked to the senior manager and shown her the files, and Nick lost his job for inappropriate office conduct. There’s a severance check for half a year’s salary and a reference letter stating they had to let Nick go due to overstaffing. Nikki sunk into her chair with her mouth agape. She can barely breathe, eyes welling with tears. Joe had betrayed her when he promised he wouldn’t. ‘Why go through all that at the reception desk tonight?’ she wonders. ‘If he was going to get me fired all along, why bother telling the security guards? Why would Joe deny me his cock,’ she thought sullenly. ‘That’s all I wanted.’
Nikki sat there, wiping her eyes before tears ruined her makeup, feeling for all the world the most useless sissy faggot God ever made. Then she spotted the second envelope. It was bulkier than the first. With a sigh, Nikki opened the second envelope. As Nikki pulled out the paperwork, it took her thirty seconds to understand what she was reading. It was a contract of employment for Nikki Thomas to work in his former position at a higher salary with a better benefits package. There’s an ID there with her picture. Joe had used one he took of her last night. However, the contract start date was not for three months.
There was another white envelope, and she opened it to find a letter and a box of pills. The pills were female hormone medication. Frowning at the tablets, she took the letter and opened it.
I know all this is a big shock, but I want you to be the real you, and I will help you. In this envelope, you’ll find a card and some pills. The pills will help you feel even more feminine and change your skin and voice to be like a woman’s, and will shrink your clit even more. Take them every day. The card is a cosmetic surgeon who’s a buddy of mine. He’s going to give you some breast implants. Don’t worry, I’m paying for them. That’s why your start date is for three months as Nikki. You’ll need time to heal.
This is not a sex change thing. I want you to keep that useless sissy clit because it made you hotter than hell. By the time you return to work, everyone will have forgotten all about Nick Thomas. Besides, you work so much nightshift they already have. Please come back and work regular hours again as Nikki. Don’t dress so sluttily, though. Find something sexy but not over the top like I saw you in last night. I won’t see you until you return to work, and then—the fun will start.
Nikki giggled and danced around the office for a few minutes before grabbing a few boxes and emptying her workspace of Nick’s belongings. After all, he didn’t work here anymore. Suddenly, Graham appeared at the door to the cubicle’s room with a smile.
“I got a message left. I need to escort an ex-employee from the building,” Graham said. “They fire you, Nikki?”
“They fired Nick,” she said. “Which was me, but I’m coming back as Nikki.”
“Damn, straight,” Graham said. “Now, better give me a taste of that ass before you go so I can tell the guys in security what they’ve got to look forward to when you come back.”
She grimaced. “Just how many guys know about me?’ she asked.
Graham frowns briefly. “Including Joe and me, I’d say about ten. Joe said not to tell you who, though. He thought it’d be fun making you sweat it out.” Graham suddenly pushed Nikki’s face into his crotch. “Ask to suck my cock,” Graham said, scrunching Nikki’s hair and making her groan.
In a soft, harsh voice, Nikki asked, “Can I suck your cock?”
“Can you suck my cock—what?” Graham asked coldly.
Nikki swallowed. “Can I suck your cock—SIR?”
“Why do you wanna suck it?”
“WHY do you wanna suck it, bitch?”
Graham dug a finger into Nikki’s back, making her moan as the sissy stared at the massive cock before her eyes. “I wanna suck it cos I was born to suck cock,” she said, hoping it was the right answer.
“So, you wanna taste and feel a real cock inside you to understand your place in this office?” Graham said, laying it on.
“Yes, sir, I do.”
The weight and girth of this flaccid black monster made Nikki’s cheeks burn and brought tears to her eyes. She was forced to use both hands; this only managed to get around his thick girth. The cock felt dense, warm, and spongy as she pulled the foreskin back to reveal the large head with a deep pee slit staring back at her. There’s no comparison to looking at this huge black cock and thinking of her tiny dicklette. The sissy had never felt so insignificant or so underendowed in her life. Even the relentless teasing in the showers at college never gave Nikki this feeling of inadequacy. The heady scent of masculinity wafted to Nikki and made her body tremble as she stroked the giant cock.
“Oh, that’s nice, Nikki, you have soft hands,” Graham said with a nod. “I like soft hands.”
It was Graham’s deep, guttural growl as he said the words that humiliated Nikki. Despite her desire to be a sissy slut, the sexist comments still hurt as deep down she still wishes she had a real cock. Could Nikki feel any less masculine than she did now? No, and she loved it.
“C’mon, Nikki…FASTER…Get me hard, bitch.”
The realization of this thing, this giant cock was more than seven inches long in her hands, and it wasn’t even hard yet, was confounding. So, gritting her teeth and taking a firm grip, Nikki started to jerk off Graham. She felt the enormous black cock getting hotter, harder, thicker, and longer in her small hands. It made the sissy’s arms ache to jerk off the long shaft. Yet when it was hard and raging at Nikki, the cock became thick and knobby with veins popping and a massive fat swollen head leaking pre-cum.
This cock was so big, at least nine inches hard, that Nikki worked the top five inches. The sissy rubbed her thumbs on the head just beneath the slit with the aid of Graham’s foreskin and slimy pre-cum.
“Oh yeah, Nikki, now you got its attention, you’d better suck it for a bit,” Graham said.
Nikki’s heart jumped with excitement at the words. Graham forced her face closer to his cock. Then the soft head of Graham’s sticky black cock hits her nose. The black man’s large hand holds her neck and crushes it tightly.
“Suck my cock, Nikki, let me feel your hot sissy mouth on it,” he moaned deeply. “Joe said you suck dick like a pro.”
The grip on her neck was killing Nikki as Graham dug his fingers in, like a claw, to grip the sissy tighter until she opened her mouth. The sissy realized Graham wanted her to resist, to struggle against him, and lose. She gladly obliged the security guard’s fantasy. Nikki’s top lip felt the heat from the rubbery cockhead as it made contact.
“It’s too big,” Nikki whined.
Graham smiled at her like a shark. “All the better for babydick sissy’s to worship,” he said.
With a distinct sob of shameful sorrow, Nikki took Graham’s cock into her mouth. The soft warmth and a salty taste filled her senses as the hot sissy closed her lips around the big purplish cockhead. The cock had a smooth, soft feeling as she moved her tongue around, yet it was so big. Graham pushed Nikki lower, forcing the head to the back of her mouth and the thick, hard shaft between her lips, then he let go.
“Mmmm, you have a hot mouth, Nikki, let me feel you suck it good,” Graham moaned. “I bet you suck like a woman too. Come on, Nikki. Suck it. That’s all that’s important now, my big cock in your sissy mouth.”
Graham’s deep growling voice and painful grip made Nikki work faster, pushing the fat cockhead to the back of her mouth and working Graham’s cock with all her skill.
“Yeah, Nikki, suck my big black cock,” Graham moaned. “Babydick sissy boy’s like you are only good for this.”
The thought a cock would jizz in her mouth gave Nikki an instant boner, despite the confines of the chastity cage. Taking a grip on the shaft, she sucked and jerked Graham’s cock faster, letting the head slam against the back of her throat as she fought against the gag reflex. Nikki settled into a fast, steady rhythm. Graham gave a loud grunt as he pulled Nikki tight into his cock and was cumming down her throat. With each deep hard thrust he gave the babydick sissy’s face, the black security guard grunted and eventually pushed her to the floor.
“That was good, babydick,” Graham said, nodding. “But we ain’t finished. Plenty of cum in these big old balls for you, so what do you want?
“Please, what, Nikki?”
Nikki smiled at the big black man, his cock still erect and standing proudly in all its glory. “Please fuck me, sir,” she said meekly.
“You sure you can take this big old black cock up your tight sissy pussy?” Graham asked. “It might hurt.”
“I want it inside me, sir,” Nikki said while her face reddened. “I wanna feel it. I wanna feel your manhood inside me.”
“Have you ever been fucked in your sissy cunt before?”
“Only with a dildo, but it was not as big as that,” Nikki said, pointing to the monster cock.
“So, I’ll be your first real schlong, I like that, now come here.”
Nikki got up and bent in front of the security guard, putting her hands on the cubicle desk for support. With that, Graham placed his cock at Nikki’s anus and slammed it hard into her sissy cunt. There’s no fingering or lube to loosen her tight sissy cunt. The black man just brutally took her.
“AHHHHHHHHHHHHHHHHHHH,” Nikki screamed.
“Fuck, another sissy cherry popped,” Graham moaned.
Graham was still not fully inside Nikki, so he hammered into her asshole, forcing his cock deeper and deeper with each thrust. The black man leaned into Nikki and covered her moaning mouth with a hand as Graham finally got all his nine inches inside her belly, balls deep. Feeling the vibrations of Nikki’s moaning through the sissy’s body on his cock got Graham even hotter. Then it was a full-on fuck. Graham hammered into Nikki, banging his balls into the sissy’s caged genitals repeatedly. The black man reached beneath Nikki and felt the plastic cage and stopped as he fished out the key and took the device off, releasing Nikki’s three-inch clit. The security guard then started fucking again and took hold of her tiny dick and fondled it. Within seconds, Nikki was shooting a load onto Graham’s hand. The black man took his palm of sissy cummies and shoved it over Nikki’s mouth.
“Eat it, bitch,” Graham commanded, and Nikki did.
Although having cum already, Graham could still fuck Nikki furiously, trying to build another orgasm. It took longer because of the blowjob as the familiar numbness went over his black cock. The big black man pounded the sissy cunt hard in the cubicle where she had worked as ‘Nick’ for the last five years. What last vestiges of masculinity Nikki may have still had slowly fucked out of her with every thrust of hard black cock.
Eventually, it all got too much for Graham. He grunted, stiffening his body, holding Nikki against his loins with his cock fully impaled in the sissy cunt. He cums. Graham thought it might never stop. He kept filling Nikki with cum and slamming hard into the sissy with all his might with each ejaculation until, eventually, the black man pushed Nikki away exhausted.
“Dang, you have a tight cunt, Nikki,” Graham suddenly moaned. “But you shit on my wang, Nikki. Get over here and clean it.”
Nikki grabbed some tissues, but Graham swatted them away.
“With your mouth, slut,” he said.
She grimaced, fell to her knees, and started licking the semi-limp cock. The taste of semen and shit overpowered her senses, yet Nikki kept licking until no trace was left.
“Don’t forget my balls.”
Nikki licked the hairy, wrinkly sack, tasting his sweaty/piss-coated balls, taking them in her mouth and sucking gently until the taste diminished. Graham lifted his ball sack and made her lick his taint, then before Nikki knew it, her tongue entered his asshole. The taste was awful, yet she obediently kept rimming the black man until he told her to stop.
“Shiite, you’re a natural, Nikki,” he said, feeling her tongue poke into his anus. “We’re going to enjoy using you around here. Get up here so I can put this cage back on your clit.”
Graham let her clean up first, and then he put the chastity cage back in place, locking away her clitty-dick for the foreseeable future.
“I can’t wait to see how much those hormone pills make it shrink even more,” he said and laughed. “You’ll soon have nothin’ there except some baby balls.”
Graham laughed again.
“Yes, sir,” Nikki said with a smile.
Graham dressed, picked up the box of Nick’s personal items, and nodded toward the elevator. “I’ll help you carry these to your car,” he said.
“You don’t have to, sir,” Nikki said with a blush.
“It’s only polite to help a lady,” he said with a chuckle.
Nikki kissed him on the cheek, and they left.
*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story was submitted directly to this website. Thank you so much for sharing your story with us.