The Sissification of Whizzie - Cover

The Sissification of Whizzie

Copyright© 2023 by Kink Bug

Chapter 2

Coming of Age Sex Story: Chapter 2 - Young Whizzie goes to L.A. in hopes of becoming a full-fledged cock-sucking cum-guzzling limp-dicked tiny-balled sissy.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Ma   Consensual   CrossDressing   Shemale   TransGender   Fiction   Humiliation   Interracial   Anal Sex   Exhibitionism   Water Sports  

It had been a long day for Whizzie Cupp, 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 turned out to be a pair of twin latino twinks called Antonio and Ansley who seemed way 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 and 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 get settled in with the twins, Whizzie moved on to the next phase of his plan. The first order of things was to find a job and some 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 places that were hiring, but either the positions had been filled, or the management there didn’t think Whizzie fit the job description.

All in all, after spending an entire day walking around and interviewing with various people, Whizzie was ready to call it a bust and just 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 that said ‘HELP WANTED’.

Whizzie squared his shoulders and walked inside.

The interior of Rusty Spoon diner had a sort of worn-out charm that somehow fit 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 tacked onto the walls in a haphazard manner as if the decorator only cared about covering up 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 and 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 the order of another table as if he had never been interrupted at all.

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 of them 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 of them 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 went back 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 the 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 suppose to elaborate.

“There’s an ad for a waitre- uh- waiter,” Whizzie trailed off, feeling a little unsure if he would be welcome. Two other jobs had rejected him because they stated they wanted men and Whizzie very obviously 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 as if he was listening in, “Cause you look more like a waitress to me.”

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

“Waitress,” he admitted in a soft tone, 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 served to showcase how large his deltoids and shoulders were.

Whizzie’s cocklette twitched in his skinny jeans, imagining for a brief moment would 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 up at Rhett.

Rhett paused to look down at Whizzie. He looked the teen up and down completely, making the teenager feel completely exposed despite the fact that he was wearing 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 all but dragged the petite boy to the back, past the kitchen where a young man was flipping patties expertly, and then into an 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 that was making weird whirring sounds.

“Well?” Rhett grunted, waiting until Whizzie turned 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 once 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 already missed it.

A dark, girthy rod sprung up into Whizzie’s face when he finally got Rhett’s pants open.

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 savouring the taste of a sweaty schlong before moving on to bathe the heavy balls underneath. Whizzie pressed his nose to the place 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 just how grateful he was 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 putting his head back where it belonged. There was no point in denying it when Whizzie was already on his knees, worshipping the cock of man he had only just met.

“Got an owner yet?”

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

Rhett seemed content to just 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 took aim 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 couple of nights ago. Now, he was given the opportunity 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 that he wouldn’t be tempted. The teen closed his mouth carefully as not to spill any of his precious liquid, and then swallowed.

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

Apparently, 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 purpose. Rhett eventually ran out of piss and made Whizzie open his mouth wide to receive his cockgifts.

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