The Road to Whoredom Pt. 01

[This is a story about someone who crossdresses and later transitions to female for purposes of prostitution, and (later) working for a pimp alongside other cisgender callgirls. This story is novel-length and has already been written in its entirety. It will be published chapter by chapter weekly, in 11 installments, near the weekend subject to Literotica moderation. The novel later includes supernatural elements and themes related to spirituality. I gave the story two titles, the first on how it begins, and the latter applicable to its middle and end. I believe this story represents a massive growth in my storytelling ability, and by far the most significant thing I've ever created.]

# - PROLOGUE

And Craving spoke, "I didn't see you descending, but now I see you rising up. Who are you fooling? You're controlled by me!"

The Soul responded: ("My friend, it is you who were mistaken!) I saw you, but you never really saw me or knew me. You mistook the cloak I was wearing for my true self, so you didn't recognise me." Having said all this, the Soul went away joyfully.

Again, the Soul came into the realm of the Third Authority, which goes by the name of Ignorance. This scrutinised the Soul closely and interrogated it, saying: "Where do you think you're going? You are the slave of malicious habits, trapped and held prisoner by your own wicked inclinations. You lack discrimination, so your judgment is unsound!"

The Soul said, "Why are you so critical of me, even though I have not been judgmental? I have been dominated and have lacked my own agency. I was never recognised for my true self, but now I have recognised this: that everything is impermanent, the whole of creation will be dissolved. All worldly things, all heavenly things, everything passes, everything will be released."

~ From the Gospel of Mary Magdalene, page 15, published sometime not long after 33 AD

THE ROAD TO WHOREDOM; AND

THE QUEST TO FIND HEAVEN ON EARTH

AN EROTIC ADVENTURE NOVEL

BY: FAUSTIAN FABLES

CHAPTER ONE:

I NEED MONEY

There Benny is, long-haired, in a rose-patterned dress over a brassiere filled with silicone breast forms, stockings, and made up like a typical Central City nightclub crawling thot. He shared this picture with only one other person. Its presence, a meme now all over social media, can only result from the cruelest form of betrayal.

High school hadn't been easy on Benny. Often, he felt himself a loser. His friend Kyle was the only one he felt he could confide in. Kyle struggled socially just as Benny did, and Benny thought he was one of the only people he could talk to about more awkward subjects like his anxiety. So, when Benny went through his non-binary phase, he naturally spoke to him about it. Kyle asked him for a photograph of himself dressed, and Benny stupidly trusted him. He kept it secret from everyone else.

It was all a mistake, Benny thinks. The whole non-binary thing, dressing like a woman, being friends with Kyle, trusting him, and worst of all, sharing that stupid photo of himself.

Benny's DMs are flooded with messages. Mostly positive comments from people who incorrectly perceived the picture as the gender-bending equivalent of him coming out of the closet. Others, from former male friends or acquaintances, are cruel, labeling him a faggot, ugly, or making fun of him. There is even a torrent of messages from some pervy older barrel-chested looking dude asking for pics, inviting him to hang out, and describing himself as generous. It makes his head ache.

It is time for Benny to go to work. How can he show his face there after his coworkers have seen him like that? His stomach knots, his arms get goosebumps, and his ribs squeeze together. He can't show his face there. It'll be a disaster. He'll be confronted and won't know what to say. It'll be humiliating.

He holds the tumbler up to the ice dispenser on his apartment fridge. It hums and drops ice that scrapes against the glass. A fifth of something cradles inside the nook of his left elbow.

Glug, glug, glug!

#

Knock-knock-knock!

It's dark in Benny's apartment. He is asleep on his messy bed. Discarded takeout boxes, liquor bottles, and Uber Eats plastic bags are everywhere.

"Benny, are you in there?" his mom asks from the other side of the locked door.

He sighs, squeezes his eyes shut, and grimaces. He should have called her. She is probably worried about him.

When he pulls it, the door creaks open, and he invites his mother inside.

His mom switches the lights on, wanders her eyes, frowns, and wrinkles her nose. "How you'd let it get this bad in here?"

He looks away and says nothing.

"It's been weeks since I heard from you," she says. "You're not returning texts or calls. I even called your work. They said they let you go for attendance."

"Look, Mom, I feel so anxious..."

"I understand, but the rest of the world isn't going to just wait around for you to get your shit together. Anyways, we need to talk about Luna."

"Luna?" he asks. Luna is his dog. She is his loyal friend, a beautiful golden retriever, and her warmth, patience, and comfort were the only things that allowed him to make it through his tumultuous teenage years.

"I just took her to the vet. There's something wrong with her stomach. She used a Latin word to describe it. I don't remember what it was. According to the vet, she doesn't have much longer to live, and the humane thing would be to put her down."

"Can't her condition be treated?"

"Yes, the vet said she could fix it via surgery. However, the surgery costs over $10,000, and I can't afford it."

#

Benny stares across the large, elaborately and colorfully carpeted floor over the roulette tables. Electronic chimes sound, blinking rows of slot machines operated by overweight retirees. The room is loud with chatter, laughing, and occasional cheers. His hands are full of cash in various denominations, which total $1,000. It's all he had left in his checking account. He has no skill or talent to rely upon, leaving him with luck alone.

A soft hand touches his shoulder.

"Handsome, before you blow that thick wad of yours, what if I told you there was a guaranteed way to score?" a female voice asks.

He turns and sees a woman with huge fake breasts, pushed out and almost entirely hanging out of the thin strips of her dark blue, short-hemmed dress. She wears stilettos and thick, gaudy makeup. Her arms are sleeved up in tattoos depicting bright green tropical ferns and colorful flowers. Although she is sordid-looking, he finds her young, busty, and alluring.

Her eyes focus on the cash in his hands.

"I've got a room upstairs. Instead of playing the machines, you can give me $600, and I'll let you use my little coin slot however you'd prefer."

Benny wets his lips, leans toward her bulging chest, and feels sweat on his hands. "N-no, thanks though..." he says, swallows, and nods. Benny's never been with an attractive woman like that and probably never would without paying for it on account of him being a loser. "Maybe next time I'm here."

She shrugs and saunters away toward the tiled floor of the bar, clacking her heels as she goes.

After converting his cash into chips, Benny approaches the roulette table. He thinks this is a bad idea. Quickly, all the money on hand he still had could vanish in an instant. The alternative, though, is losing Luna. Luna is more important than money.

The dealer, dressed in a black and white vested uniform with a red bow tie, nods at him and smirks. His eyes are emerald green.

Benny closes his eyes and silently prays that he will save Luna.

He puts all $1,000 worth of chips on the first dozen.

The dealer spins the wheel, which whirs mechanically as the ivory pill clatters against its edges.

Benny bites down on his lip, fidgets in place, and clears his throat.

"No more bets!" says the dealer.

The pill clatters against the various numbers.

Click!

It lands on black eight.

The dealer picks up two stacks of chips and places them on the green felt of the table before him.

He bets them on black while keeping his original $1,000 chips out of play.

The wheel spins and the pill clatters.

Click!

It lands on black twenty-two, and the dealer gives him another two stacks.

Benny swallows hard. He has enough to put it all on red or black; if he wins, he could cover Luna's surgery. That's a lot to risk on one bet, though. However, the odds are slightly stacked in favor of the house when playing roulette. The longer he plays, the more he is potentially disadvantaged by the unequal odds. The key is to win big and quickly and quit when ahead.

He puts it all on black.

The dealer stares at him with his emerald green eyes and smirks.

Benny's eyes blink rapidly.

"Wait!" he says, and moves his chips to red.

The wheel spins and the pill clatters.

"No more bets!"

Benny's brow wrinkles as he pinches the skin of his throat.

Click!

The pill stops at black thirty.

Benny stares down at the table's green felt, blinks, parts his lips, and freezes in place.

The dealer scoops up all his chips.

Damn it, if only he hadn't wasted all that money ordering food deliveries. He shouldn't be a lazy loser, especially when he has his car, which he could've used to pick up his orders.

Benny hesitates. Many lazy people like him live in Central City.

#

Wee-woo, wee-woo, wee-woo, wee-woo!

Shit, Benny's like twenty over the speed limit.

The engine hums softly, and the brakes creak as he activates the turn signal and pulls into a Weinerschnitzel parking lot.

Tick-tock, tick-tock, tick-tock.

The police SUV parks next to him, flashing red and blue lights. The door creaks open, and a uniformed Central City Police Department officer with a crew-cut and mustache climbs out. He scuffs his boots against the pavement as he walks to his window. A velcro name plate on the officer's uniform reads, Reed.

The driver's side window hums as he distends it.

Officer Reed hacks and wheezes.

"Jesus fucking Christ, why does your car smell like that!?"

Benny shrugs. "I've got five different food orders here. I think this one has a bunch of Indian curries. This is, from what I think, a hot chicken place. I'm not even sure what type of restaurant this one is from. Some weird fusion place, I think. I guess when combined, it smells awful."

"Gross. Do you know why I pulled you over?"

"I was speeding. Sorry, Officer, I didn't realize until I saw your lights. Look, I am just trying to make some money to pay bills. If you could cut me a break, I am juggling a lot of deliveries here."

Officer Reed grins, nods, scuffs his boots against asphalt, creaks his door open, slams it shut, puts his feet on his car wheel, inserts earbuds, swipes at his cell phone, and chuckles.

Benny's foot taps, his mouth scowls, and his eyebrows raise. What is he doing? Watching TikTok videos? This will cost him all his tips on these orders.

Several minutes pass before Officer Reed exits his SUV holding a boxy mechanical device. As he approaches Benny's window, the device whirs, and a rectangular paper prints out. He hands it to him.

"This is a citation for speeding. Right here it lists the fine, and down here is the information if you want to contest this in court."

Benny's eyes keep shifting to the delivery app on his phone.

"Can I go now?"

"Yes."

#

Ding-dong!

Benny stands outside the door of a run-down apartment. The faded numbers on the door are difficult to discern, but he believes this is the correct place.

The door opens, and a tall, dark-skinned man wearing a white wife-beater and black basketball shorts enters the doorway. He scowls before crossing his arms over his chest.

"How come you so late?'

"Sorry, there was traffic. Here's your order."

The man grunts indignantly and takes the bag, which crinkles.

Benny turns his back on him and scurries back toward his car.

Crunch!

"Yo, where you running off to faggot? This hot chicken's fucking cold. How you gonna disrespect me like that?"

Benny continues to hurry back to his car. He doesn't have time for this. There are other orders awaiting delivery. Plus, the man appeared angry. Benny thinks a fight is exactly the sort of thing he'd fuck up. "You can request a refund through the app!" he yells.

The man snarls.

"Fuck the goddamn app. How about I take the refund out your little bitch ass!"

Benny hears him running behind him, and he runs, jumps into his car, breathes heavily, scrapes the key against the ignition switch, and turns the engine on with a hum. His foot slams the accelerator pedal, and he reverses out of the spot, only to see the man deliver a jump kick to the passenger rear video mirror, severing it from the side of his car with a metallic scrape, followed by a thud.

Benny speeds away without the mirror. He debates calling the police, but feels it would only waste his time. Besides, he has more orders to deliver.

#

Kid, are you not getting these messages? Please respond. I'm not BSing you. $$$

Benny stares down at his latest message. The dollar signs are emojis. Why is he so persistent? His head tilts, and he rubs at his chin. He clicks his profile and swipes through his photographs. He looks like a put-together guy. In his pictures, he portrays himself as muscular and good-looking for an older man. Benny doesn't consider himself attracted to men.

He wonders how much he pays guys and/or girls to hang out with him. The thought causes him to rock back and forth in place, making him feel dizzy inside. A man like that would take advantage of him, and the relationship could only be unequal and humiliating to him.

#

"It looks great. How much do I owe you?" Benny asks.

"Nothing," says the mechanic. "Insurance covered it 100%. If you have any issues with the mirror, it's under warranty for the next six months."

Benny's lips part, and his eyes widen. He expected another massive bill.

#

"You're honor, I am not disputing this. I did speed."

"The court will accept your plea of responsibility and assess you a fine of $473."

"With all due respect, your honor. I cannot afford this fine. I am currently unemployed and have no savings. I am trying to pay for my dog Luna's surgery. She will be put down if I can't raise the money."

"Having lost a beloved dog of my own recently, I am sympathetic to your situation, but my hand is forced by what the law prescribes. I will say that you are young, in good health, and resourceful. I imagine soon enough, you will come up with a way of making money."

He can't deal with this fine right now. Not while Luna is sick.

#

Hello?

He sent Benny another DM.

Hi, Benny messages back.

Benny frowns and shakes his head. He shouldn't have responded to him; it can only lead to bad things. Now he's going to be too anxious to log in. Good riddance. He hates all the people constantly congratulating him. He's not trans or non-binary. He might not be stereotypically masculine, but that doesn't mean he has to adopt some recently invented gender-identity label. After Luna is well again, he will work toward settling the score with Kyle.

#

What the fuck is this, thinks Benny.

He stands alone in his apartment's mailbox room holding an open envelope letter in one hand and a crinkled sheet in the other.

The letter states that his car insurance company has opened an investigation regarding the replacement of his rear-view mirror. After determining that he has been running an undisclosed ride-sharing side business, he apparently owes them an additional $6,375 in insurance premiums. How the fuck is he supposed to afford that?

The color drains from his face, his stomach churns, and the gaze of his eyes darts around. He can't survive anymore. He's lost at life itself.

#

Luna, lying on her back, whimpers and shivers.

Benny rubs her belly, chokes down a cry, and tears roll down his cheeks. She is obviously in pain due to her stomach condition. If the roles were reversed, he has no doubt she'd cry for him.

They're in his parents' chilly, dark basement. There are a few couches, a coffee table, a minibar, an old flat-screen TV, racks of DVDs, and video games.

"It's ok, hang in there, girl. I'm do... doing everything I can." His voice cracks when he speaks.

Luna's whimpers end, shivers subside, and she snores.

He retrieves one of his stepfather's whiskey bottles and a glass tumbler from the minibar. He sets these on the coffee table and slumps into the couch. Using the remote, he turns on the television, which flickers before displaying an episode ofFamily Feud. He pours whisky into the glass.

Glug, glug, glug.

#

Benny is still in his mom's and stepdad's basement. It's unclear how long he's been here. He sees Steve Harvey on the screen. It must be a marathon. His hand shakes as he pours another glass of whisky.

Glug, glug, glug.

It tastes smoky when he sips, and burns the back of his throat.

He looks at the television. He never noticed Steve Harvey's bright green eyes before.

Benny stares at his smartphone screen. He has new DMs. He wonders if that gross older guy responded. His face blushes. It's embarrassing that he even replied. He shouldn't engage with him any further. However, it's just some random guy. He could ghost him at any time. Benny no longer sees any downsides to simply conversing with him.

Kid, this messaging at the pace of a turtle is killing me. I'm just trying to have a conversation.

Sorry, I've been busy.

What about right now? Are you busy now?

No.

Can you send me more pics? My name is Raymond, btw.

No, that is the only one of me dressed like this.

Would you like me to send you pics of me? Raymond asks.

Benny hesitates, bites down on his lip, sips smoky amber from his glass, and shrugs. Okay, he messages.

The smartphone's bright screen contrasts with the basement's dark interior. There is an issue with his parents' broadband connection, causing theFamily Feud theme song to play distorted. The phone buzzes. Benny checks his DMs and sees a photograph of a long, thick cock grasped by the person who snapped the photo. It's shaven, swollen, with long blue veins. He's never seen one up close in person, but this rivals some of the largest he's seen through his consumption of pornography.

Benny's hands feel sweaty, his eyes keep staring, and he feels it stir inside his pants. He blinks and shakes his head. Why would he send this to him?

WTF? Benny messages.

OMG, I am so sorry! I clicked on the wrong thing. Go ahead and delete that kid. This is what I meant to send.

It's a picture of Raymond, but Benny has seen it before. It's the same as one of the photos on his profile.

Kid, you like what you see? You've responded. Surely, something's got you intrigued.

Benny hesitates, bites his lip, and fidgets on the sofa.

I need money.

Wow, Kid, I appreciate your honesty. I was your age once. I didn't have two dimes to rub together. When you're in that situation, you haven't any choice but to put work in. You understand what I'm saying, right, kid?

...

Cut it out with the dots, you want money, right?

Yes.

Let's hang out, kid.

Like a date? Do you want to meet for dinner?

In public? No way. Let's hang out at my place. Come dressed like the picture. Don't skip the makeup either. You need money? Do what I say, and you'll get paid.

It's just hanging out, right? Nothing weird or gross?

Sure, kid, just me paying you to spend some wholesome time together at my house.

#

It's dark in Benny's apartment bathroom, and he opted to prepare by candlelight. The dim, crackling flame is forgiving compared to the fluorescent overhead LED light bulb. It's been a long time since he dressed as a woman, and he did not want to overfocus on his shortcomings, as he worried about developing gender dysphoria. Standing against the glass mirror, his smartphone glows as a makeup tutorial plays on YouTube. Benny follows the instructions, applying mascara and pink lipstick.

Benny manipulates his fake silicone breast form tits through the rose-patterned material of his dress so they appear perky and natural. He didn't agree to do anything. There's nothing he is obligated to do. Raymond offered to pay him to hang out. That's it.

Through the dimly lit reflection of the mirror, Benny sees an attractive, thin, young woman.

#

A cold breeze causes Benny to shiver as he stands outside the entrance of Raymond's white suburban tract house. It's dark outside, and the young man, dressed like a young lady, hesitates and faces the street.

Tall trees loom over the sidewalk and adjacent street, their branches rustling and shedding verdant leaves in the whistling wind. A hooded jogger passes by the opposite side of the street, looks upon Benny with emerald eyes, smirks, and vanishes into the night gloom.

He sighs, bites his lip, and rubs at his chin. Clad in a dress, fake breasts, and heels, he feels his chest tighten and tingle. He wants to go home, but he needs money. If he doesn't do this, Luna will die.

Ding-dong!

The door creaks open, and Raymond stands grinning in the frame, clad in a black polo shirt and faded denim jeans. He appears slightly older than he portrays himself in his profile pictures and lacks the tight waist he sports in his photos. In its place is a protruding beer belly. Otherwise, his appearance mirrors his photographs; he is tall with a muscular barrel chest and thick, rigid arms. The top two buttons of his polo shirt are undone, revealing a patch of matted chest hair. He holds the door open and steps aside for Benny.

"H-hello," Benny says, swallows, and comes inside, clacking his high-heels against Raymond's burl wood floor.

Raymond slams the door shut before seizing Benny from behind, caressing his bare shoulders covered only by the thin straps of the rose-patterned dress with his moist palms.

The hair on Benny's neck bristles, he feels goosebumps on his arms and legs, and he pulls away from the older, more prominent man.

"S-sorry," the younger man dressed like a coquettish girl says. No sooner does the word leave his mouth than he becomes self-conscious of how masculine he sounds. Applying his best attempt at a feminine affect, he continues, "I'm a little nervous."

Raymond stares at him with a toothy grin. It's dark inside the entrance/living room, except for the glowing, muted television broadcasting an NFL matchup featuring the Central City Sharks. "Maybe a drink would loosen you up?" he asks.

Benny blinks. Alcohol sounds nice. "Yes, please," he says. Benny's eyes widen, and his ribs squeeze together. He thinks his attempt to sound feminine came across as slutty and desperate-sounding.

Raymond chuckles and nods. He leaves the room and returns holding a dark beer and a wine cooler. "Let's relax on the couch." Raymond unmutes the television.

"... the triumphant return of offensive lineman Troy Daniels following his catastrophic injury..."

Benny would prefer the beer but enjoys role-playing as a girl.

"... for the first time this season..."

Raymond's thick, sweaty hands grope at Benny's stocking-covered legs.

Benny's stomach quivers, and he feels a chill come over him.

"... the Shark's quarterback Buck Johnson..."

Raymond pulls Benny against him and slides his hand further up his inner thigh.

Benny feels Raymond's curly chest hairs against his forehead and smells the older man's sandalwood cologne. "Uhm," he interrupts. "Can I use your bathroom?"

#

The toilet flushes while Benny creaks the bathroom door shut. His eyes peer down the dark hallway at the orange glow emanating from one of the doorways on the right. Blinking his eyes and tilting his head, he clacks his heels against the burl wood and investigates the illuminated room.

Inside, Benny finds a large king-sized bed with white sheets and a tawny comforter. Various items are scattered atop a long, waist-high bedstand on the other side of the room. He shrugs and switches off the light by clicking the switch. The room darkens before a beam of moonlight shines through the panes of an adjacent window and catches on some shimmering object on the bedstand.

Benny squints at the shimmering object and rubs at his chin. He clicks the light switch back on, illuminates the room in a warm orange glow, and approaches the object. He lifts it with a metallic clunk. It's a pair of handcuffs. Benny wonders if Raymond is a police officer. He looks at the other objects on the bedside stand. There is a prescription bottle for Viagra with the lid unscrewed, a large plastic Vaseline container, and a box. Benny picks up the box before realizing it is a condom carton.

Benny thinks about the picture Raymond had sent him. He imagines him fastening one of the stretchy condoms around it. His hard cock stirs underneath his panties and dress.

A door shuts behind his back.

Benny spins around, still holding the box of condoms in his hands, and sees Raymond smirking at him while he rubs his protruding stomach with his right hand.

"Someone's eager. It's ok, kid; we can skip the foreplay."

Raymond removes his shirt, revealing his muscular arms, hairy, barreled chest, and fat, protruding belly.

"Wait, I swear, I wasn't trying to get you to sleep with me," Benny pleads.

Raymond flexes, gestures with his head to the growing bulge underneath the younger man's dress, and chuckles.

"If roleplaying makes the whoring easier for you, I'm more than happy to oblige," Raymond mocks with a sneer.

"This was a mistake," Benny says, sets down the box of condoms, and attempts to walk past Raymond to exit the bedroom.

Raymond grabs the smaller man in a bear hug before hurling Benny onto the middle of his large bed. With the pointer finger of his left hand, the older man scoops up the metal handcuffs, which he spins around on his finger while his belly jiggles.

Benny lifts his torso only to find himself face-to-face with Raymond.

The older man grabs his arms, and while Benny struggles against him, Raymond's superior strength allows him to overpower the younger, cross-dressed man. He clicks the handcuffs closed and binds Benny's two hands to the brass headboard of his bed.

"Let me go! Please! You can keep the money!"

Raymond climbs off the bed, snickers, unclasps his belt, and lets his pants and boxers fall to the floor. His rock-hard, bulging, fat prick pulses when he gives it a gentle tug with his right hand.

Benny stares at the cock, feels his hands moisten, his mouth waters, and his skin turns pale with goosebumps. It looks even bigger in person.

"Like what you see, kid?"

Raymond smirks, crumples the box of condoms, fishes a long translucent one out of the box, tears open the wrapper, lets it fall onto the wood floor, and wraps it around his engorged schlong with a sleazy squeak.

Benny struggles atop the bed and scrapes the cuffs against the brass headboard.

Chuckling, Raymond unscrews the plastic lid of the Vaseline container, coats his hand in gooey wax, and greases up his thick condom covered pole.

"Please let me go, please let me go!" pleads Benny as he thrashes atop the bed and scrapes the cuffs.

Raymond climbs onto the bed holding the Vaseline container in the nook of his left elbow. He hums a seemingly made-up tune as he reaches inside of Benny's dress, removes the younger man's silk panties, pulls them down Benny's stocking-covered legs, and over his high-heels. The older man takes another greasy handful of Vaseline and smacks it against Benny's virgin ass.

"No, please don't do this!"

Raymond continues to hum as he plunges two coated fingers into Benny's asshole and lubricates his anal cavity.

"Oh my god! Oh my god!"

Raymond lifts each of Benny's legs so that they rest atop his broad shoulders before positioning his fat cock toward the younger man's exposed butthole.

Benny's neck hairs prickle, his skin pales with goosebumps, and he shivers.

Raymond eases the head of his fat prick into Benny's anus.

"Wow, kid, you're tight."

"It hurts!"

"It'll be ok, kid, just let me pump it inside of you and it'll feel good. I promise."

"O-0k."

Raymond spreads Benny's legs, deflowers his virgin ass, and pumps his greased-up pole in and out of the younger man. He begins slowly but gradually increases the pace as he continues.

Benny tears up, winces, scrapes the cuffs, and endures a huge penis inside his tight asshole.

"See kid, it's not so bad."

Raymond spreads Benny's legs, leans up and over the smaller man, dominates him, and rapidly slams his fat cock in and out of his puckered asshole.

Benny drools, shivers, moans, and feels a chill followed by feverish heat. He never felt like this before.

Raymond grunts as he pounds his penis into Benny.

"It feels good, huh, kid?"

"Yes."

"Say, yes, daddy."

He's cuffed to Raymond's bed, impaled on the older man's cock, and entirely vulnerable. His ribs squeeze together, and he feels like he used to when he was bullied in school. A perennial loser, it's not surprising someone like him would end up being a fat man's sissy manwhore.

"Y-yes, daddy!"

Raymond slams his cock deep inside Benny, causing him to tremor and moan.

"That's how women feel when they lie with a man. Honestly, you should be the one paying me for this. If you'll dress this way, you should let guys do this to you."

Benny blushes and says nothing. His stomach knots.

Raymond pumps harder and harder into his young whore Benny until there is an audible smack with each thrust, and he is so dominant atop the younger man that his protruding jiggling belly vibrates against Benny's cock as he buries his own penis inside the crossdresser's gaping butthole.

"Oh god, oh no," Benny says before his cock, sandwiched between Raymond's jiggling belly and his hard stomach, explodes all over his chest and the inside of his dress as if someone had stepped on a bottle of mayonnaise.

"Don't you move, kid!" Raymond yells with a snarl as he rapidly accelerates his pumps, grunts loudly, pushes his penis deep inside the younger man, and emits a long, strained moan. Breathing heavily, the older man dismounts Benny, revealing he has blown a massive gooey load into his used condom.

"Here you go, earned every bit of it, kid," Raymond says as he retrieves a wad of cash totaling $250 and tosses it onto Benny's sticky semen stained rose-printed dress. Raymond leans over and releases Benny from the handcuffs. "Oh, and a little souvenir." The older man reaches between his legs, squeaks off his dirty used condom, and lays it on Benny's dress next to the cash.

#

Benny bathes in warm water while attempting to wash out every bit of sweat, filth, and makeup from each and every crevice of his disgusting body. There was good reason his initial instincts warned him to avoid cavorting with a man like Raymond. He had to admit, however, that there was still something positive about the experience. Like there was some nugget of the divine he felt looming nearby but never quite in reach, something otherworldly about getting fucked like that. However, whatever he had felt was tainted by all the filth and sleaziness that accompanied it. The squeaky condom, handcuffs, prostitution elements, him and Raymond calling each other kid and daddy, the sweaty penis smell, the abundance of semen, all of these things served to crush him, lessen his spirit, and humiliate him. He would have to find other ways to make money.

#

"Look, I've got $2,000, can't you just invoice me the rest?" Benny asks

"I'm sorry, we need payment in full before we can begin the procedure," the veterinarian says.

"Luna's life is on the line. I'm doing everything I can to make money. Please, I'm begging you."

"Look, if you give me the $2,000, I can at least schedule the surgery. However, you'll have to figure out how to come up with the rest of the money."

#

"Hello, Officer Reed," Benny says. "I've been watching my speed, I swear. I wasn't even going one mile over the limit."

Officer Reed sniffs. "It smells good today," he says.

"Yeah, I just picked up a big order from Giuesuppe's. A couple of pizzas and some pasta, it looked like."

"I didn't pull you over for speeding."

"So what's the problem, Officer?"

"Benny, you're driving on a suspended license. You never paid the fine from the last ticket."

"My license is suspended?"

"Yes, I see here in the system it just happened earlier this week. You probably haven't gotten the letter from the DMV yet. Since you didn't know, I will give you a pass this time. After this delivery, though, you will have to either work it out with the DMV or stop working. Driving on a suspended license is a crime. You can be booked into jail for it."

Benny frowns and bites down on his lip.

"Thanks for the warning."

As Officer Reed drives away, Benny sighs. It's like everywhere he goes, everyone has to remind him what a loser he is.

#

Benny walks back and forth, scratches at his face, and shakes his head. He thinks he must get his mind off this money situation, or he will freak out.

Benny peers over at his cell phone on top of his computer drawer.

He thinks he shouldn't do it. It's gross and demeaning. He thinks he should be a good boy and not a nasty, debauched whore. Maybe, though, if he indulges in the dark things he fears so much, if he humiliates himself, the crushing anxiety will dissipate. Even if temporary, he can only imagine the psychic relief.

Benny pulls the curtains closed to every window in his apartment, leaving it dark.

He sits in the chair and stares at the phone. His lips part, allowing a sigh to escape.

With shaking hands, Benny pulls open the desk drawer, causing it to scrape against the railing. Carefully, he reaches inside and retrieves Raymond's crusty, used condom. He couldn't believe this had been so deep inside his ass. He opens up his smartphone, pulls up the photo of Raymond's penis, and places the phone upright against his computer monitor.

Benny reaches between his legs and strokes his cock, uses his left hand to fingerfuck his asshole, and darkly fantasizes about whoring himself to Raymond.

#

Benny wears a yellow vest with #11 on the back. Next to him is a man his age wearing the #26 vest.

A giant green arm controlled by AI that selects and moves around pallets of consumer products appears to be stuck in place.

"What happened to it?" Benny asks. It is his first day on the job.

#26 can't hear because everyone in the workplace is wearing ear protection.

A high-pitched whir sounds.

A man is typing furiously on a keyboard near the control panel. A second man stands over him, shouting. Benny can't make out a word of it.

Whoosh!

The AI arm snaps forward at high speed with a pallet, strikes a woman wearing the #17 vest, knocks her helmet off, slices into her head, and exposes her skull.

Benny looks away and vomits onto the concrete warehouse floor.

The system is shut down.

Benny removes the earplugs and hears screaming and yelling. That giant green arm terrified him ever since he started. He wonders if it may have acted intentionally out of contempt for its slavers.

"Now you know why there was a vacancy," yells #26.

"Fuck this," Benny says, removes the vest, and walks out.

#

"What the fuck is this?" Benny mutters as he stands outside his apartment. "An eviction notice?" He thinks he will soon live in a cardboard box on the war-torn streets of Old Downtown, the final destination on the penitent road to loserdom.

#

"Look, I can pay half the rent now, and half in two weeks," Benny explains.

"I don't know how many times I have to tell you this," the community manager says and rolls her eyes. "We don't do payment plans. I've disabled your ability to pay. If you don't want to be evicted, you must pay off the full balance with late fees in certified funds; no credit cards."

This only confirms his suspicions about his likely future.

#

Benny looks into his bathroom mirror, flares his nostrils, shakes his fists, and screams. It's like the whole fucking world is designed to trap him in debt and financial misery. He shouldn't need to humiliate and debase himself to get by. He's sick of the indecent proposals. Why can't he be an ordinary guy with a healthy dog?

The reasons he must do what he will are manifest.

Benny sighs dejectedly, slumps his shoulders, and stares at his reflection with dull eyes. He props his smartphone up on the mirror and starts the makeup tutorial. He opens his cosmetics bag and pulls out the mascara.

#

Raymond leans back in his brown sheepskin armchair and puffs on a cigar.

Benny kneels before the older man wearing frilly pink and white lingerie and rabbit ears. "Thanks for buying this outfit for me, Daddy," he says.

Raymond laughs. "I didn't buy it for you. It belongs to my wife." The older man is wearing a red bathrobe that hangs over his fat belly and a leopard skin jock strap underneath.

Benny thinks he is doing it again. Reminding him of his lowly status, not as a girlfriend or lover, but as some whore he two-times his wife with.

"Time to earn that money, kid," Raymond says with a snicker. "Before you do your thing, why don't you give me a nice slutty lap dance?"

Benny shrugs and offers, "I will try my best." He swipes his smartphone and pulls up an EDM song on YouTube.

"Mmm, sounds good, kid, really get up there and grind on it."

Raymond opens up the bathrobe and sticks out his jockstrap-covered groin.

"Umm, yeah," Benny says, gets up off his knees, shoves his ass barely contained in the frilly g-string panties against the older man's swollen crotch.

"C'mon, kid, get bouncing on it."

Benny swivels his hips in unison with the music while bouncing his jiggly ass cheeks against Raymond's hardcock through the thin leopard print material of the jockstrap.

"Jiggle those cheeks for me."

"Like this?"

Benny swivels his hips so his cheeks separate before clapping back into place, smacking the sides of Raymond's stiff prick, which is now so engorged it can be seen straining against the fabric.

"Alright, enough of this silly stuff, get back on your knees, kid, and whore out your mouth to me."

"You don't want to just fuck me like last time?"

"No, I want you to suck it like a little bitch."

Benny swallows and bites down on his lip. He comes right out and says it now.

"I've never done that before."

Raymond shrugs.

"We're not talking about something that takes a lot of skill and expertise here. If you've eaten a hot dog before, you know what to expect."

Benny, with trembling hand, peels back the leopard jock strap material until he frees the older man's throbbing penis. It's warm as Benny strokes it with his right hand.

"Get on with it now."

Benny leans in and smells it. It's musky and smells like a gym sock.

"C'mon, kid, enjoy it."

Benny stretches out his jaw muscles.

"It's not complicated. Just wrap that pouty mouth of yours around it."

Benny strokes the shaft, and something oozes out of the tip.

"What's that?"

"It's cum."

"You came already?"

"No kid, are you stupid or something? It's precum."

"Should I wipe it?"

"No, lap it up with your tongue."

"I don't..."

"Just do it."

He might force him to if he doesn't do it, which would be even more pathetic. Benny does as he says, and it tastes salty and sweaty.

"Now, suck it."

Benny wraps his mouth around the head of the older man's engorged cock and slurps back and forth until a suction is created.

"See, all of that and you're a perfectly natural cocksucker."

"Mmm humm," Benny mumbles as he pumps his puckered lips up and down Raymond's thick penis.

"Keep that slurping going, I like loud and messy blowjobs."

Raymond grabs the side of Benny's head, holds him in place, and throatfucks deep until he is gagging and coughing up cups of spit all over the floor.

Benny coughs and breathes heavily.

"C'mon now, suck my balls, kid."

Benny sighs, grabs the older man's shaft, and holds it up so his balls hang openly. He licks his lips and then begins to tongue them. The sweat, musk taste, and smell are even more concentrated, and the texture feels weird against his tongue and lips.

"Make sure each one makes it inside your mouth. Get them deep in there, really want them to rub against the whole inside of your mouth and tongue."

Benny nearly gags as he slurps on an older man's sweaty balls. Grabbing the shaft with his right hand, Benny slides his tongue up from the bottom of Raymond's ballsack and up the shaft to the tip before plopping the penis back into his wet mouth. As he sucks, he can feel that his chin and throat are soaked in spit.

"Uh huh, good job kid, that just about does it," Raymond says, pulls Benny off of his swollen penis, and begins rapidly pumping with his right hand.

"Wait, don't!"

Plop, plop, plop!

Three enormous blobs of cum slapshot out of the tip of Raymond's cockhead onto Benny's face, followed by sprinkler-like jets. The cum is warm, pungent, and sticky. It does not take the older man long to glaze Benny's face with hot, viscous semen completely. As he defiles his whore's grimy face, Raymond releases a torrent of grunts and moans. Through heavy breaths, he says, "Don't talk back to me, kid. Remember, the customer is always right."

Benny begins to speak, only for Raymond to scoot back, causing a long gooey string of cum still stuck to the younger man's face to break off and slingshot right into Benny's open mouth.

"Uh-huh, that's right," says Raymond as he reaches into a pocket on his robe and pulls out another $250. "Go buy yourself something nice, kid. From now on, consider me a weekly customer."

#

Several weeks pass.

When Benny arrives home, a police officer and his community manager stand in front of his apartment.

"What's going on?" Benny asks.

"Is this your apartment?" the officer asks.

"Yes," Benny says.

"Here, this is an order from the court," the officer says before handing Benny a crinkled paper. "I've changed the locks on your apartment."

"What about my stuff?" Benny asks through a cracked voice as a tear escapes from his right eye. This is it. He is homeless now.

"Focus on finding someplace to stay for tonight," the officer advises. "Once you've got a new place, you can return and get your stuff. You've got twenty-one days to do so."

Benny begins to cry.

"Here, take this flyer. Some community resources might be available to you."

Benny takes the flyer, sniffles, and returns to his car. He is unsure what to do now; whatever it is, it will require more money.

Benny phones Raymond.

"Hello, uh, you in the mood for... well, you know."

Raymond chuckles.

"Kid, just say it how it is. You'd like to whore yourself out to me right now."

"Yes, I do."

"Kid, just say it."

"I want to whore myself."

"Yeah, you want me to rent that butthole of yours, don't you?"

"Yes, daddy, please rent my butthole."

"Ok, consider it booked and about to be occupied."

"Uhm, can you pick me up? Also, can we stop by somewhere that sells makeup? I will probably need to borrow one of your wife's outfits again."

Raymond sighs.

"Jesus, kid."

#

"So did your wife work at Hooters?" Benny asks as he bounces up and down on Raymond's hard prick atop his marital bed. His breast forms fill out the low-cut signature uniform from the restaurant, while the orange short shorts lie neatly on the bed next to them.

"Of course not," Raymond snaps. "You think I'd marry someone who works at Hooters? It was a Halloween costume she wore one year."

"Oh, ok," Benny says, straddles the older man, lifts himself up and down his greased-up pole, and bounces on his hard cock like a ragdoll while he goes for a ride.

"So, what do you think about me living with you?" Benny asks. "I'd offer you discount prices and on-demand services. Plus, I promise not to take up much space. Just a spare bedroom should be fine."

Raymond grabs Benny's hips and bounces him up and down his thick cock. "What are you crazy?" he asks. "I'm married. I can't just move my sissy whore into my spare bedroom. You forget this because I only invite you when that old bitch isn't around."

"Unh," Benny grunts before releasing a slow moan. "You could get divorced?"

"As much as I'd love to be rid of her and as good as it feels to fuck your little faggot asshole, I don't much care for getting fucked in the ass. Family court is like taking it from a crazed bull." Raymond grabs Benny and grinds him against his lap as his cock throbs inside.

"I like how it feels all raw inside me," Benny says. "It was a good suggestion, since you're my regular now, that we don't use a condom."

Raymond smirks and says, "You just want to take one of my nasty loads inside of you."

Benny pants and bounces up and down while impaled by Raymond's fat penis. "Gawd, it feels so good," he purrs.

"Get ready," Raymond taunts before snickering.

"Oh my god, you're going to make my asshole so gooey and sticky with that."

Raymond slams his penis inside, grabs Benny's hips, and holds the younger man in place to be inseminated.

"Oh my god, I can feel it, it's warm," Benny says.

Raymond creams the younger man's asshole before dismounting.

Benny grabs the orange short shorts from the Hooters outfit and jerks his cock until he ejaculates into them.

#

As Benny walks down the pathway from Raymond's front porch to the sidewalk, he blinks and notices a new-looking light-blue Mercedes-Benz S-class sedan parked in front of the house. Leaning back against the car, staring forward toward the house, is a tall, lean, and well-muscled man. He is clean-shaven with curly black hair and tan skin. He wears a black vest with nothing underneath, likely to show off his lean, well-developed upper torso and abs. He wears sunglasses, diamond-studded earrings, a Gucci designer belt, expensive blue jeans, and Italian dress shoes.

The man gestures with his head to the wad of money in Benny's hands. "You work hard for that money?" he asks.

"Just some cash I had saved up," Benny lies.

The man smirks, wags his finger naggingly, and grunts, "Tck." He stands up and moves away from the car and toward Benny. "Didn't your parents raise you right? You don't lie to people. You're dressed like a guy but have makeup on, love. Besides, I watched you just now through that window. You rode some fat guy like he was your bicycle, dressed as some slattern waitress, and then he gave you that money you have in your hand."

Benny's lips part, and he is still and silent. "Excuse me?" he asks.

"Love, I saw everything."

"A-are you a... cop or something?"

"Something, definitely something. You are not in trouble with the law. At least not what you traditionally think of as the law. But you have broken what I would describe as the law of the streets. You see, I am responsible for this area. What you did is a crime. Crime is regulated. Not only by the police. Whenever a financial crime of this nature is committed in this area, I am the one responsible for paying Remy his cut. But you haven't been giving me the money. Instead, you're wasting it on the stupid things people buy, like apartments or traffic tickets."

"Yeah, well, we can't all afford $100,000 cars," Benny responds.

"Well, maybe the fact that I can means you should listen to what I say."

Benny parts his lips before closing them.

"That's right," says Fine Tony. "You're in debt to me for every dollar you've made whoring."

"So you are threatening me?"

"If you want to interpret it that way. However, I see it as I am trying to help you. I'm offering you the greatest opportunity you've ever been given. If you disagree that it lives up to the hype, leave once you've paid your debts. My name's Fine Tony, by the way."

Fine Tony extends his right arm out with the palm facing out.

Benny stares at his palm.

"The money in your hands, give it to me," Fine Tony says.

Benny blinks and tilts his head. "All of it?" he asks.

Fine Tony grins, nods, and says, "That's right, all of it."

"I keep none of it? That doesn't seem fair at all."

Fine Tony shakes his head. "You don't understand because you're trapped," he says. "They've built into you this mentality that we are atomized individuals, each working a job and making money, and then we use the money to buy the things we want. I am not offering you a job, nor am I offering you the opportunity to make money. I am offering you a lifestyle where money isn't necessary."

"How can money not be necessary?"

"When I take my girls to the club, I get us bottle service, when we eat out, it's Wagyu A5 steaks, when the girls and I go on vacation, we fly first-class and stay at five-star resorts, when I take them shopping, they buy whatever they want, whatever brands they want, and money is never an issue. They don't need money, they don't care about money, and it might as well not even exist to them. I provide all of this to them, help them find clients, deal with deadbeats, pay Remy, and we all live together in a lovely fancy house like one big makeshift family."

Benny has spent the past several weeks constantly worrying about his financial needs. The idea of a lifestyle where he does what needs to be done without worrying about finances sounds... comfortably liberating. He is lonely and isolated from his family. He's in dire need of a new one. Whoring is as easy as lying on your back and taking it up the butt. Even a loser like him could manage that.

Benny stares at the money in his hands and then back at Fine Tony's open palm. "I have a dog who's sick," he says. "If I come to work for you, can you help me?"

"Sure, love. We'll get all that worked out. I love dogs, so she's welcome to come too, as long as she's house-trained and you pick up the poop. I don't want Horace to get stuck having to do it."

Benny thinks that he doesn't have anywhere to live. He doesn't trust Fine Tony. But Benny is poor and running out of time. He tried to do things the right way. Perhaps crime is the only way someone like him can keep his head above water anymore. He did not choose this life, but perhaps his life chose this for him.

Benny gives Fine Tony all of the money.

Fine Tony slaps Benny's shoulder and grins. "Welcome aboard," he says, opens the passenger-side front door, and gestures for him to enter the vehicle. "We'll stop and get you some female clothing before I take you to meet the girls. What's your name, anyway?"

"Benny."

"Benny? Nah, that's not going to work. From here on out, your name is Penny."