Cover of Part-time Sissy

5 chapters · 4708 words · Read 0 times

Jim is a submissive, closet sissy with a deep desire to be put in chastity, be feminized, and perform oral sex on alpha men. He feels great shame, but is aroused by humiliation, pushing him further. He takes a part-time job at an adult book store after being talked into it by the cute clerk, a dominant, cruel pixie-ish woman that always teases him when making purchases. She said the discount is great and he would love being surrounded by perverts every day that visit the glory hole booths in back. He agrees and she becomes his keyholder as a condition of employment, as she quickly feminizes him while at work and offers his services to men in the glory holes. She updates his contract to state that he must satisfy at least 3 men per shift, which sometimes extends beyond the four walls of the store. She takes lots of pics with him dressed up and sucking cock, convincing him they should be shared online.

Chapter 1: Introduction

A bell on the door tinkled, reverberating through the oddly empty store. Only an hour left before closing time. Jim was restocking the wall of dildos with varying sizes he'd rather not think about.

"Hi, honey!" A high-pitched voice rang out. "Late for work, aren't we?"

Jim looked up to see the clerk that'd talked him into this degrading part-time job, standing there with her arms crossed and one hip cocked insolently.

Her bright green eyes, accentuated by heavy eyeliner, glinted mischievously.

"Ah, Janice." He sighed, straightening up and tugging his short brown hair nervously. "You know I don't like being called 'honey'."

"Oh, I know! But it's so much fun watching you bristle, my sissy." She smirked, flipping her short, bleached-blonde hair over her shoulder.

He rolled his eyes, then glanced around the Adult Book Store.

Its grungy atmosphere seemed even more pronounced under the fluorescent lights now casting harsh shadows around the room. The X-rated DVDs lining the shelves gleamed suggestively while the erotic literature and lingerie offered promises of sin and pleasure.

Janice sauntered closer, leaning in. "You look just like a little doll today, darling. Can't wait until you're all mine." She winked, a sadistic glint sparking in her eyes. "How's that pretty little cage I got for you?

Still fitting comfortably, dear?" Janice teased, snapping her fingers at Jim, who flinched despite his best efforts not to react. She waved a set of keys in front of him, the keys to his new chastity device.

Jim felt a blend of terror and exhilaration wash over him. He'd been humiliated at work and roped into this arrangement, his deepest desires now at the mercy of Janice. Yet somehow he found himself yearning for this domination, craving the feeling of helplessness that came with it.

While he was horrified at his apparent predilections, he could not deny the arousal that surged through him when Janice took advantage of his vulnerabilities.

His throat constricted, swallowing his unease as the cold metal pressed against his skin. Fingers brushed against his semi-erect penis, sending tingles of pleasure coursing through him before the clasp was closed, trapping him.

"Remember, darling, you can't touch yourself without my permission," Janice whispered seductively into his ear, tracing a finger down his neck.

"And if you disobey, well..." She pulled away, grinning wickedly. "Let's just say I have ways of making sure you regret it."

Jim gulped, trying to hide his nervous excitement. "I won't... I mean, I understand, Janice."

She patted his cheek condescendingly. "Good boy. Now, let's get these last few hours over with. We've got some... preparations to make for tomorrow."

Jim nodded, following her towards the counter. "What's happening tomorrow?"

Janice turned, her eyes sparkling with malice.

"Oh, didn't I tell you, sweet cheeks? Tomorrow's your initiation."

Jim raised an eyebrow, trying to maintain a semblance of calm. "Initiation?"

She leaned in, her voice dropping to a conspiratorial whisper. "Yes, darling. You see, every new employee here goes through a little... rite of passage. A way for us to make sure they're truly committed to their new role."

Jim's stomach churned with a mix of dread and anticipation. "And what exactly does this initiation involve?"

Janice grinned, her teeth glinting like a predator's.

"Well, that would spoil the surprise, wouldn't it? Let's just say it involves you, me, and a few of our... regular customers."

Jim's eyes widened behind his glasses. "Customers? Like, the ones who come in here?"

"The very same." Janice chuckled, clearly enjoying his discomfort. "Don't worry, sweetheart. They're all nice, big, strong men who love a good time. Just like you will, once you learn to embrace your true nature."

Jim felt a shiver run down his spine, half from fear, half from something else he couldn't quite identify.

He tried to push the thought of what tomorrow might bring to the back of his mind, focusing instead on the mundane task of wiping down the counter.

Janice watched him with amusement, her head tilted slightly to one side. "You know, Jim, you really shouldn't be so nervous. It's not like you haven't fantasized about this before."

He blushed furiously, avoiding her gaze. "That's different. Those were just... thoughts. Not reality."

She laughed, a sound like tinkling bells.

"Oh, Jim, you're so cute when you're embarrassed. But don't worry, tomorrow we'll turn those thoughts into reality. And you know what? You're going to love it."

Jim bit his lip, trying to suppress the butterflies fluttering in his stomach. He wasn't so sure about loving it, but he couldn't deny the thrill that ran through him at the thought of his fantasies becoming real.

Janice reached across the counter, grabbing a small, discreet box from beneath the register. She slid it towards him, a smug smile playing on her lips.

"Here, take this home with you tonight. Consider it... homework."

Jim eyed the box warily, as if it might bite him. "What is it?"

Janice leaned in, her voice dropping to a husky whisper. "It's a little something to help you prepare for tomorrow. A toy, if you will."

He swallowed hard, his curiosity piqued despite himself. "What kind of toy?"

She grinned, clearly enjoying his discomfort. "Open it when you get home, darling. I promise, it'll be...

enlightening."

Jim picked up the box, turning it over in his hands. It was unmarked, nondescript, yet it felt heavy with implications. He tucked it into his bag, trying to ignore the heat rising in his cheeks.

As the clock struck ten, Janice flipped the sign on the door to 'Closed', locking them both inside. The store seemed to grow darker, the shadows deeper, as if the very air was thick with anticipation.

"You know, Jim," Janice began, her voice casual as she started counting the day's earnings, "you should really consider letting your hair grow out.

It would suit you."

Jim looked up from where he was sweeping the floor, his brow furrowed. "What? Why?"

She shrugged nonchalantly, but there was a calculating gleam in her eye. "Just think about it. Longer hair would frame your face nicely, soften those sharp features of yours. Make you look less... ordinary."

He bristled at the implication, but before he could respond, Janice continued, "Besides, it's not like anyone's going to see you outside of work, right?

So why not embrace the full experience?"

Jim paused, considering her words. He had to admit, there was a certain logic to them. If he was going to go along with this charade, he might as well commit fully. And who knew? Maybe long hair would actually suit him.

"Fine," he relented, setting the broom aside. "But only because it makes sense strategically."

Janice clapped her hands together, delighted. "Wonderful! I'll make an appointment for us at the salon tomorrow afternoon. After your...

initiation, of course."

Jim groaned internally, already regretting his decision. "Great. Something else to look forward to."

Janice ignored his sarcasm, grinning widely. "Oh, you'll love it, Jim. Trust me. Now, let's finish up here so we can both get home. I've got plans tonight."

They worked in silence for a few minutes, the only sounds the rustling of paper money and the occasional clink of coins. As Jim finished wiping down the counter, he noticed Janice staring at him, a thoughtful expression on her face.

"You know, Jim, I've been thinking," she said, tapping her chin with a perfectly manicured nail.

"What about?" he asked warily, tossing the cloth into the sink behind the counter.

"I think it's time you started wearing some makeup to work. Just a little, nothing too dramatic. It'll help complete the look, you know?"

Jim's stomach dropped. Makeup? He'd never worn any in his life, and the idea of starting now made him feel even more exposed than he already did. "I don't know, Janice.

Makeup seems like such a... permanent thing. I'm not sure I'm ready for that step yet," Jim hedged, running a hand through his short hair nervously.

Janice rolled her eyes, leaning against the counter. "Oh, please. It's not like I'm asking you to wear a full face of drag. Just a little concealer, maybe some mascara. Nothing too drastic."

Jim bit his lip, considering her suggestion. On one hand, the idea of wearing makeup made him uncomfortable, like he was crossing some invisible line he hadn't known existed.

"Also, I think it's time to shave those legs of yours. Will look so much cuter in your new uniform." Janice grinned, pushing off from the counter and sauntering towards the back room.

Jim's eyes widened. "Uniform? What uniform?"

Janice paused at the doorway, looking back at him with a mischievous glint in her eyes. "Oh, didn't I mention? All employees here wear a special uniform. It's... part of the experience."

Jim felt a sinking sensation in his stomach. "What kind of uniform?"

Janice smirked. "You'll see tomorrow, darling. Now, come on. Time for your final task of the night and then time to go home. I know how much you love cleaning all the sticky cum out of the video booths in back by hand. Chop chop!" Janice clapped her hands together, shooing Jim towards the back of the store. "We don't have all night, darling. Some of us have lives outside of this place."

Jim sighed, trudging towards the row of video booths. He hated this part of the job - the smell, the feel of the sticky messes left behind by the store's patrons. But Janice insisted that he clean them by hand, claiming it was character-building.

As he entered the first booth, he could feel the weight of the chastity device pressing against him, a constant reminder of his newfound status.

He knelt down, grabbing the bucket and sponge, steeling himself for the task ahead. The booth was dark, the only light coming from the flickering screen playing a loop of some generic porn scene. He could hear the faint moans of the actors, the wet sounds of flesh slapping against flesh, and he felt a familiar stirring in his groin.

He gritted his teeth, trying to ignore the growing erection straining against the confines of his cage. This was ridiculous. He was a grown man, for crying out loud.

He shouldn't be getting aroused by cleaning up other people's messes in a seedy adult bookstore. But here he was, kneeling on the grimy floor, his heart pounding in his chest as he scrubbed at the stains on the seat in front of him.

The booth was stifling, the air thick with the scent of sweat and sex. Jim could feel the heat rising in his cheeks, his breath coming in ragged gasps as he tried to focus on the task at hand. But it was no use.

His body betrayed him, his cock throbbing painfully against the unforgiving metal of his chastity device. He could feel the pre-cum leaking from the tip, dampening the fabric of his underwear. He clenched his jaw, trying to hold back the moan that threatened to escape his lips.

Suddenly, the door to the booth swung open, revealing Janice standing there with her arms crossed, a knowing smirk on her face. "Having fun in here, are we, Jim?" she taunted, her eyes flicking down to the bulge in his pants.

Jim scrambled to his feet, his face burning with embarrassment.

"Janice, I-I wasn't—"

She held up a hand, silencing him. "Relax, Jim. I'm not blind. I can see exactly what you were doing." Her smirk grew wider, more predatory. "Or rather, what you weren't doing."

He looked down at the floor, unable to meet her gaze. "I can't help it. It's just... it's hard to control sometimes."

Janice stepped into the booth, closing the door behind her. The space grew smaller, the air even thicker with tension. "Hard, hmm?

I bet it is." Janice's voice was low, husky, as she took another step closer to Jim. He could feel the heat radiating off her body, see the hunger in her eyes. His heart pounded in his chest, his breath coming in short, shallow gasps.

"Janice, please..." he whispered, his voice barely audible. "Not here. Not like this."

She laughed, a sound like tinkling bells, and reached out to trace a finger along his jawline. "Oh, Jim. Always so proper. So uptight. But that's what I love about breaking you.

Watching you squirm, seeing you fight your own desires. It's so much fun, isn't it?"

Jim swallowed hard, trying to find his voice. "I-I guess."

Janice's finger moved from his jaw to his lips, tracing the outline softly. "You guess? Or you know?"

He parted his lips slightly, allowing her finger to slip inside. He sucked gently, tasting the saltiness of her skin. She withdrew her finger, a satisfied smirk on her face.

"That's better. Now, let's get back to work.

We've still got a store to close, and I want you to finish cleaning these booths before we leave." Janice stepped back, her eyes still locked onto Jim's, daring him to defy her.

Jim nodded, his throat tight. "Okay, I'll finish up here."

Janice turned to leave, then paused at the door. "Oh, and Jim? Don't forget to wipe down the glory holes too. Wouldn't want any of our customers to catch anything nasty, now would we?"

Jim's eyes widened in horror. "Glory holes? Really?"

Janice rolled her eyes.

"Oh, don't act so shocked, Jim. You know what kind of store this is. Besides, it's not like you haven't thought about it before. Admit it, the idea of some anonymous stranger using you like that turns you on, doesn't it?"

Jim felt his cheeks flush with embarrassment and something else he refused to acknowledge. "That's... that's not the point, Janice. It's unsanitary, and I'm not comfortable with it."

She sighed dramatically, leaning against the doorframe. "Fine, fine. I'll make you a deal.

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