Read Part 1 Here.

*****

Part 2…

It had been a long day for Whizzie Cupp, an 18-year-old sissy-wannabe.

Daxton Foley, the trucker who took him from his hometown of Idyllwild to Los Angeles, had dropped Whizzie off at a small block of apartments on the edge of Compton, saying that he had friends who were willing to let Whizzie stay with them for a little while until Whizzie found his footing in the big city.

The friends were a pair of twin Latino twinks called Antonio and Ansley, who seemed too close, even for Twinks. They let him have ‘Ansley’s room,’ but truth be told, when Whizzie dropped his backpack in the tiny room, it looked as if it had barely been lived in. But then again, who was he to judge? After all, he was trying to become a limp-dicked sissy.

Antonio and Ansley cooed over Whizzie, saying he was already pretty sissified. It wouldn’t be long before he found himself a man and became a properly feminized whore.

Whizzie thought they gave him too much credit, but he appreciated the thought.

After taking a day to settle in with the twins, Whizzie moved on to the next phase of his plan. The first order was to find a job and a stable income. Whizzie’s savings would not be able to sustain him for long in Los Angeles, and he needed more clothes; he had left most of his boy clothes back in Idyllwild because there was no place in a sissy’s life for unfashionable things!

And so, Whizzie had gone out searching for a job in Compton. The twins had given him a list of hiring places, but either the positions had been filled, or the management didn’t think Whizzie fit the job description.

After spending an entire day walking around and interviewing various people, Whizzie was ready to call it a bust and go home. No one was gonna give him an interview at 9 pm, right?

Whizzie paused in his steps when he heard laughter across the street.

Two people spilled out of a dingy diner on the corner and stumbled down the street.

Whizzie had passed it earlier. Maybe he was wrong, but he vaguely recalled seeing a cardboard sign in the window that said ‘Help Wanted.’

He let his feet take him over to the muggy door and looked up at the words on it.

‘RUSTY SPOON DINER. ’ And sure enough, a tiny cardboard sign said ‘HELP WANTED.’

Whizzie squared his shoulders and walked inside.

The interior of Rusty Spoon Diner had a worn-out charm that fits its name quite well. The scent of sizzling grease and the faint aroma of burnt coffee immediately washed over Whizzie, making him feel a little hungry. The dim overhead lighting cast a yellowish hue on the vinyl booths and chipped Formica tabletops. There were faded posters of classic rock bands and vintage pin-up models haphazardly tacked onto the walls as if the decorator only cared about covering bare concrete.

Even though it was late, there was still the sound of clattering dishes and murmured conversations. There was one other waiter, a guy who looked as if the weight of the world had been set on his shoulders, and he couldn’t be arsed to carry anymore. He darted back into the kitchen, came out with a tray of something that smelled divine, set it on the table between two burly workers, and then went back to taking another table’s order as if he had never been interrupted.

There was a jukebox in the corner, and it was crooning an oldie from days gone by, barely audible over the bustle in the diner.

The booths were filled with a motley crew of customers. Most looked like tired locals just looking for a bite to eat after their long shifts. The worn leatherette seats and cracked vinyl bar stools showed signs of years of use. Checkered tablecloths covered each table, all stained in one way or another.

“You coming or going?” the waiter yelled.

Whizzie startled and hesitated, “Coming?” he asked.

“Well, whad’ya want?”

“Um, there’s a sign. Help wanted?” Whizzie hedged.

The waiter looked at Whizzie.

“RHETT!” he yelled at the back, then abruptly returned to his work like nothing ever happened.

The door to the kitchen popped open and out stepped a Latino man wearing a grease-stained apron over a white muscle tee and black jeans. Like most other men, he was taller than Whizzie by far. His kinky dark hair was cropped to his chin, and his light green eyes were blazing with what Whizzie could only describe as barely concealed contempt.

“What?” he demanded, his voice a low growl as he crossed his arms over his huge pecs.

“I’m looking for the manager?” Whizzie hedged, feeling nervous at being confronted by such a man who was towering over him.

“Ya looking at him,” Rhett snorted, “Name’s Rhett Depina. I run the Rusty Spoon.” Then he cocked an eyebrow at Whizzie that clearly said that Whizzie was supposed to elaborate.

“There’s an ad for a waitress- uh- waiter,” Whizzie trailed off, unsure if he would be welcome. Two other jobs had rejected him because they stated they wanted men, and Whizzie wasn’t a real one.

“You sure you’re a waiter?” Rhett snorted. He thumbed at his nose and glared at the waiter, who looked like he was listening in, “Cause you look more like a waitress to me.”

Whizzie flushed with shame and embarrassment. This proved that Whizzie looked too feminine to be a boy but still not yet feminine enough to pass as a girl.

“Waitress,” he admitted softly, fidgeting with the edge of his shirt.

“Well, you got any experience?” Rhett demanded.

“I used to work part-time at a diner in Idyllwild…” Whizzie had helped with the touristy areas, but the tourists were mostly nice people who just wanted to enjoy some cold mountain air.

Rhett made a dismissive sound in the back of his throat. He uncrossed his arms and put his hands on his hips, which only showcased how large his deltoids and shoulders were.

Whizzie’s cocklette twitched in his skinny jeans, imagining for a brief moment what it would feel like to be manhandled, thrown to the floor, and fucked right there and then on the grimy tile of the diner.

“Idyllwild doesn’t get anything more than a handful of customers,” Rhett pointed out, “I need to know you can handle the morning, afternoon, and evening rush in LA.”

“I think I can handle it!” Whizzie said, hoping that he sounded confident, but the scowl on Rhett’s face told him that he did not!

“Well, that’s not very convincing now, is it?” Rhett turned to walk back into the kitchen.

Whizzie lurched forward and grabbed a fistful of Rhett’s shirt.

“Please just give me a chance?” he begged, turning his big blue eyes at Rhett.

Rhett paused to look down at Whizzie. He looked the teen up and down completely, making the teenager feel completely exposed even though he wore several layers of clothing. The grumpy look on his face turned into something more lecherous, more cruel, and Whizzie shivered.

“Guadalupe! Stanley! I’m gonna interview a waitress!” Rhett yelled.

“On it, boss!” there were two overlapping voices, one from the back and the other from the waiter.

Whizzie couldn’t tell who was who.

Rhett grabbed the teen’s wrist and dragged the petite boy to the back, past the kitchen where a young man was flipping patties expertly, and then into a squat yellowing office.

Whizzie gasped as he was shoved into the little room. There was a fluorescent lamp struggling to stay lit, bills upon bills pinned to a corkboard, and an old desktop making weird whirring sounds.

“Well?” Rhett grunted, waiting for Whizzie to look at him before continuing, “Get on your fucking knees and show me if you’re worth a hire. sissy”

Whizzie’s heart skipped a beat. He didn’t expect to have to do this, but then again, he was a sissy through and through. And sissies didn’t say no to cock!

“Yes, sir!” Whizzie said, quickly dropping to his knees.

He eagerly leaned forward, lifting the apron out of the way to get at Rhett’s jeans. Whizzie licked his lips as he quickly undressed the older man, eager to feel the weight of a thick rod on his tongue again.

It hadn’t even been 24 hours since Daxton left Whizzie at the twins’ place, hadn’t even been 24 hours since Whizzie had a load of cum pumped down his throat, but Whizzie had already missed it.

A dark, girthy rod sprung into Whizzie’s face when he opened Rhett’s pants.

Whizzie couldn’t stop himself from letting out a soft moan of appreciation. He heard the older man snort in amusement. The teen opened his mouth wide and sucked on the tip, happily savoring the taste of a sweaty schlong before batting the heavy balls underneath. Whizzie pressed his nose to where cock met sac, taking a deep breath of that heady masculine scent. It was incredible, that smell! It was so manly, so sweaty, so musky!

The apron covering his head was pulled off as Rhett set it aside. Whizzie looked up at the man with his large blue eyes, trying to convey his gratitude for the opportunity to suck cock.

“You wanna be a sissy, don’t you?” Rhett grunted as Whizzie sucked.

“Yes sir, I do,” Whizzie pulled off just long enough to reply before returning his head where it belonged. There was no point in denying it when Whizzie was already on his knees, worshipping the cock of a man he had just met.

“Got an owner yet?”

Whizzie shook his head mutely, tongue still working on the tip of Rhett’s lovely dick.

Rhett seemed content to watch Whizzie suck, making approving noises when Whizzie attempted to swallow the rest of the thick fuckpole. Of course, being a baby sissy, Whizzie wasn’t anywhere near proficient enough at deepthroats to do that, but that didn’t stop the teen from trying!

GORK—GORK—GORK!

Went Whizzie’s mouth and throat. Halfway through, Rhett grabbed his head and pulled him off.

“Open,” he ordered.

Whizzie opened his mouth and stuck his tongue out.

Rhett aimed and relieved himself, aiming the stream into Whizzie’s open maw.

Whizzie had drunk Daxton and Perez’s piss straight from their cocks only a few nights ago. Now, he was allowed to watch as the yellow stream arced through the air and landed in his mouth, making a little whistling sound as it did so. The sight had his cocklette jumping eagerly, and Whizzie pressed a hand over his crotch to calm it down.

Rhett cut off the stream as Whizzie’s mouth filled. He waited, an eyebrow arched expectantly.

“Well? Flush it down,” he growled, “And get that hand off your dickies. Sissies don’t touch their weenies.”

Whizzie obeyed, putting his hands behind his back so he wouldn’t be tempted. The teen closed his mouth carefully not to spill any of his precious liquid and then swallowed.

“Thank you, sir,” he smiled up at Rhett.

That was the reaction Rhett was looking for because he nodded in approval and then started to fuck Whizzie’s face again.

Rhett alternated between letting loose streams of piss and bouts of intense face-fucking. Each time the disgusting urine splashed into Whizzie’s mouth, arousal and shame warred in the teen’s body. Serving as a urinal was humiliating in how fulfilling it felt like he had a purpose. Rhett eventually ran out of piss, making Whizzie open his mouth wide to receive his cock gifts.

Whizzie moaned softly when the first rope of cum hit his tongue.

He was beginning to love the taste of piss and cum together. They were both bitter and pungent, combining to create a uniquely intoxicating taste of degradation and depravity.

“That’s a whore now,” Rhett muttered, more to himself than to Whizzie, as he wiped his dick on the teen’s tongue and put himself away.

Whizzie sat back on his haunches and looked up at Rhett eagerly.

“How did I do?” the teen asked, full of hope.

Rhett gave him a curt nod.

“You start tomorrow morning. Seven am sharp. I’ll have your uniform ready.”

Whizzie cheered.

Wanting to make a good impression, Whizzie arrived at the diner at 6:50. When he pushed open the door to the Rusty Spoon, the waiter, Guadalupe, was already wiping down the tables, and Whizzie could hear clanging in the kitchen, which meant Stanley was starting the grill.

Rhett appeared and jerked his head at Whizzie.

The teen swiftly complied, following Rhett to the office.

“You’ll be wearing the waitress uniform, but with a few alterations and extra accessories,” Rhett informed Whizzie as he led the teenager inside and closed the door.

There was a uniform laid out over the desk in a haphazard manner. But unlike the bright yellow shirt and dark slacks that Whizzie saw Guadalupe wearing, there was a bright yellow shirt and a flouncy little brown skirt that would barely cover anyone’s butt. On top of the uniform, there was pair of bright yellow thigh-high stockings, a steel anal plug with a ring in the base, and a small-sized cock cage. There was also a pair of platform boots under the table.

“What’s all this?” Whizzie asked in shock. He knew he would be a ‘waitress,’ but he didn’t think it involved all these other implements.

“You’re a sissy, or at least on your way to becoming one,” Rhett said gruffly. “As someone who owns a sissy, I can’t in good conscience let your basic sissy needs go unfulfilled. Trannies like you need caged dicks, regular ballbusting, routine asspussy ramming, and nonstop humiliation. If a sissy isn’t humiliated enough, they start to get ideas, which can be dangerous for their mental and sexual health.”

“What … what sort of ideas?” Whizzie asked with trepidation, looking at the older man. While the teen knew that he wanted to eventually become a limp-dicked sissy, he thought that was something that would just come with time. He didn’t think chastity or anything else was that important.

Rhett gave Whizzie a once over as if trying to determine if any of these ideas had already permeated Whizzie’s mind.

“Ideas like they have a say in what happens to their holes when in the presence of a real man, ideas like they deserve any kind of respect from anyone, or that they get to say no to cock and any cock gifts,” he drawled.

Whizzie gasped.

Those sorts of thoughts felt anathema to Whizzie. Growing up, Whizzie always knew that he would serve cocks, that he needed to be humiliated properly, and that he should welcome every emission from a man. Proper sissies knew their place as disposable fucktoys.

“I don’t want to get those kinds of ideas,” Whizzie said, horrified at the thought that such a thing could happen. He couldn’t imagine ever saying no to a thick cock, nor did he ever want to!

“Of course, you don’t,” Rhett said in a kinder tone. He reached out to help tuck Whizzie’s blond hair behind an ear, looking at the teen with an almost fatherly gaze, “Because you want to be a good little sissy. But I’ve seen what the lack of humiliation does to a sissy, and it’s dangerous. You might end up hurting yourself!”

Rhett held up the steel cage and showed it to Whizzie. It was designed for a tiny dick, like the one between Whizzie’s legs. The curved structure looked barely big enough for a dick to fit inside, preventing the wearer from becoming erect.

“This is why you’ll wear this chastity cage and the plug now. The cage will remind you that your dickie is pathetic and useless, while the plug keeps your boicunt nice and open for all the real men who want to use it.”

Whizzie swallowed at the casual display of dominance. Rhett didn’t ask permission. He merely told Whizzie what the sissy was supposed to do and expected it to be followed. Which was, of course, the way it should be!

Rhett continued.

“Your weenie will only be unlocked for half an hour after your shift. It will remain locked even on your days off so that you don’t get any ideas about touching your dick or trying to masturbate with it! You’ll also wear these thigh-highs that clip onto the base of your plug. If anyone asks you what you are, you will tell them you’re a sissy. If a customer wants to use you, you will take them to the backroom and obey all their commands. You will swallow everything that comes out of a pussy or a cock, and you will thank them for it.”

Rhett looked at Whizzie, waiting for a response, and there was only one thing that Whizzie could say!

“Yes, sir, thank you, sir!” Whizzie exclaimed breathlessly. He had lucked out by coming to this diner! Who knew that Rhett would become an experience sissy owner or that he would be willing to help Whizzie on his sissification journey?

Rhett nodded in approval. He looked pleased at Whizzie’s prompt reply.

“Good, now get over here.”

Whizzie quickly shucked off his jeans, then gasped as Rhett manhandled him up onto the rickety-looking desk of the office. The older man grabbed the teen’s tiny cock and balls, crushing them in his palm for a few minutes and making Whizzie moan before putting the cage on.

The cage came in two parts – a ring base and the cage. Rhett’s large fingers moved deftly, pulling Whizzie’s small cock and balls through the hole. Whizzie shivered as the cold metal rubbed against his tiny weenie. It was twitching vigorously, aroused by being manhandled by a real man. Once the base was snug behind Whizzie’s useless sac, Rhett grabbed the cage and slid it over Whizzie’s cocklette.

It was a little shorter than Whizzie’s little dickie, but Rhett didn’t care. He crushed the cage towards the base, forcing Whizzie’s little cocklette to compress into Whizzie’s crotch. The sensation was a little painful but also hot as hell! Whizzie watched, transfixed, as those thick fingers swiftly locked the cage into place.

This was it. Whizzie was now a caged sissy.

The sight of the cold steel wrapped around Whizzie’s dickie was completely foreign, but it felt so right. Pathetic little nubbin deserved to be caged like this. Even though Whizzie’s balls were smaller than average, they still protruded from the bottom ring of the cage, forming an almost heart-shaped bulge that mirrored the sissy desires in Whizzie’s heart.

This was the start of Whizzie’s cock chastity and penile denial. He wouldn’t have access to his dick anymore unless his boss said so, and it happened in a messy, cluttered office in the back of a dingy and plausibly disreputable diner in the shadier side of Los Angeles.

Whizzie shivered all over. The cock cage was a physical manifestation of his wish to become a true sissy, an outward signifier of his journey. Even if Whizzie had second thoughts, Rhett didn’t seem like the kind of person to let Whizzie back out, which was good because a sissy needed a strong hand of discipline.

Rhett shoved the skimpy short skirt at Whizzie in a clear indication to get changed. The teen obeyed, pulling off his clothes to stand naked in the office.

Any other person might be embarrassed to change in front of their employer. Still, since Whizzie was a sissy, real men had a right to use and abuse his body in any way, so it didn’t matter.

“Sir, if I may ask, why do you have all these?” Whizzie asked as he pulled on the yellow shirt uniform. His puffy nipples were visible under the thin fabric, no doubt another thing that Rhett had considered.

“These?” Rhett asked. He casually hooked the key to Whizzie’s cock cage onto a chain around his neck. He tucked it under his shirt, “My sissy is off studying in Arizona and usually only comes home once every other weekend. She’s been using flat cages for years now that she’s properly castrated. I’ve got her balls up over there.”

Rhett sounded proud. He pointed at the wall, drawing Whizzie’s attention to a clear resin block. In the middle of the resin was a small but lovingly preserved scrotum that had been removed whole. A pink carnation rested over the scrotum as if to replace the missing cock, and there was a golden inscription underneath.

Whizzie stood on tiptoes to read it.

“Sissy Kitty’s Pathetic Balls (March 27, 1994 – July 20, 2019), taken by Master Rhett Depina.”

Seeing another sissy’s dedication and submission immortalized in such a humiliating way was humbling. But it was also empowering because it meant this Sissy Kitty had been confident enough to relinquish her nuts to her master.

Whizzie wondered if he would ever find a man that Whizzie could honor with his balls. But in the meantime, he had a truly dominant boss that cared about enforcing proper sissy behavior, which was a blessing to anyone on a feminization journey!

“Bend over the table,” Rhett ordered.

Whizzie hurriedly pulled up his stockings and obeyed.

The sissy teen moaned softly when he felt the steel of the plug press against his anus. Rhett didn’t give a shit about whether it hurt Whizzie or not, forcing the implement through the tight muscle and into Whizzie’s hole.

“Oooo ohnngh!” the teen whimpered. Rhett spanked Whizzie’s upturned bare buttocks hard, shifting the plug in his tight hole.

Then, the older man attached all of the straps of the thigh highs to the ring at the bottom of the plug’s base. Whizzie whimpered. The thigh-high stockings shifted when Whizzie straightened up, tugging the plug downwards. Whizzie’s eyes widened, and he clenched instinctively, locking his asspussy around the steel to prevent it from being yanked out.

“Good sissy,” Rhett nodded in approval, looking Whizzie up and down.

A wave of humiliation washed over Whizzie. He had been born male, but here he was, in a dingy office, wearing an slutty waitress uniform designed to shame and train him. His balls bulged out from a ring that kept his cocklette compressed into his crotch. The uniform skirt brushed against his pathetic twig and berries, making him ultra-aware of his chasteness. Whizzie’s buttplug was designed to help keep his thigh highs up, but his stockings had been designed to try and pull his plug out.

No sane man would ever subject himself to such treatment. But here Whizzie was, about to step outside and start his new job as a waitress at the Rusty Spoon in the ridiculous get-up because he wasn’t a real man. He was a sissy, and this was part of his journey.

Rhett grabbed Whizzie’s butt, squeezing it painfully, then growled, “Get out there and have a humiliating first day, sissy!”

There was only one thing that Whizzie could say!

“Yes, sir, thank you, sir!”

 

To Be Continued…?

 

*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 has been previously published on other free sites and is now public domain, which is why we can publish it here.