Dear reader,

Thank you for your continued support of 'Role of a Lifetime'! This chapter was a pleasure to write and I hope you enjoy it! Can you imagine Chris as he was months ago in this situation? I can't imagine him pulling off 'female prostitute' like our Chrissy can!

Next month's short story is called 'Into the Dungeon.' The first chapter will drop next Monday so stay tuned :)

Chrissy’s animal print heels clacked against the concrete sidewalk. She jogged to catch up with Sapphire, who was moving purposefully down the street while holding her black bag. Chrissy’s normally girly prance was disrupted as she had to use one of her arms to maintain the integrity of her precariously balanced tits in the skimpy boob tube while her other hand kept her swishing, crusty skirt from flipping up and revealing her bare lower body.

Sapphire turned into an alleyway and waited for Chrissy to catch up. The alley was relatively empty and wide, with high, brick walls surrounding it. It stretched for a hundred or so feet before opening back up behind a strip mall. There was a dumpster and a few trash bins off to the side as well as some random debris strewn about.

Sapphire led Chrissy to the middle of the alley, next to the dumpster, where she stopped and faced a metal shutter covering some sort of opening. She whipped out a silver key and removed a lock connecting the shutter door to a metal brace anchored into the brick wall. With the lock removed, Sapphire was able to lift the shutter door and send it crashing upwards. The opening turned out to be a simple brick indent in the wall approximately ten feet tall, twelve feet wide, and seven feet deep. Chrissy glanced around the secluded space in confusion. It was empty. Was this some sort of storage space?

Sapphire tossed the lock and key into her bag. She then reached behind the dumpster and dragged out a disgusting, stained mattress, which seemed to be hidden there purposefully.

With a grunt, she tossed the mattress into the indent before procuring a faded green sheet from her bag and laying it over the discolored mattress padding.

Sapphire smoothed the sheet on her hands and knees. Chrissy watched from behind, not at all registering that the skirt riding up Sapphire’s hips, revealing her juicy, thong-covered ass and plump pussy, was even remotely sexy. In fact, there was nothing about Sapphire that aroused Chrissy in the slightest. Her brain had been completely rewired to only recognize manly traits, parts, and bits as attractive. Sapphire could have been the hottest woman to ever exist, but Chrissy was so staunchly heterosexual that the most mediocre man with the most mediocre penis would trump her every single time. Chrissy’s holes were reserved for hard cocks only, and both her body and mind were in complete agreement.

She watched Sapphire with boredom, wondering how this was supposed to work. Would Sapphire bring men back here to have sex? Was Chrissy going to stand in the corner to watch? What exactly did Sapphire expect from her? How long were they going to stay out here?

When the sheet was properly secured, Sapphire stood and dusted off her hands. She fixed her skirt and turned to speak, “Aight Candy, we ready. We got’sta bring them johns to our little slice’a paradise, you dig? Daddy gots this figured out where ain’t nobody see us from the road doin’ our thang.”

Chrissy cleared her throat and apprehensively rubbed the track marks on her forearms as she squeaked, “Um, Sapphire? What is it that, like, you want me to do?”

Sapphire started towards the street and scoffed over her shoulder, “What’chu mean, Candy? You gon’ fuck some john while I make sure he pay. This yo’ learning experience Daddy want you to have so you gon’ have it.”

Chrissy nervously nibbled her heavily coated lower lip and ran a long pink acrylic through her greasy hair while complaining, “That isn’t—that isn’t, like, what I thought, okay? I was TOTALLY thinkin’ I was gonna just, like, watch, you know?”

Sapphire stopped and giggled, “Oh, my sweet lil’ Candy! You gon’ be suckin’ a dick or takin’ it up yo snatch or asshole fo’ CASH MONEY on this mattress! It’s aight, it’s just a dick, you feel me? Jus’ like me, yo body is made to take dick. It’s biology and shit.”

A pit formed in Chrissy’s stomach, and she squirmed in her skimpy boob tube and crusty skirt. She may have looked...a little like a prostitute, but she wasn’t actually one!

“Isn’t prostitution, like, illegal and junk?” Chrissy asked softly.

Sapphire shrugged, “Sho’ is. But only if yo’ loud, moanin’ ass is caught. If you is quiet you ain’t gon’ get caught.” She then turned and swayed towards the street, “Less go, we wastin’ Daddy’s money. Ima do the talkin’ so you jus’ flaunt what you got an’ I’ll get’choo a man.”

The residual arousal from being fondled, combined with the fear of being alone in an unknown area, coupled with the loyalty Chrissy felt towards Sapphire, led Chrissy to reluctantly follow. With her temporarily yellow/brown teeth, greasy hair, obvious track marks, and pockmarked face, Chrissy hoped that nobody would buy what she was selling.

They were soon standing on an abandoned, decrepit street corner.

Sapphire stood by the curb and gently rested her hands on her hips while adopting a provocative, feminine posture and a half-lidded, pouty expression. Chrissy did what she could to mirror Sapphire, but her version was shy and unsure. She couldn’t believe she was standing on a street corner in the ghetto wearing almost nothing and looking like a prostitute! How had it come to this?

EVERY car slowed down as they passed, and Chrissy noticed EVERY occupant of those passing cars reacted with wildly different responses ranging from disgust to lust and everything in between. There was no denying it. Chrissy was advertising that her body was up for sale, and everybody was keenly aware of that fact. She felt like a collection of wet holes ready to be used and discarded by anybody with a few dollars in their pocket and a cock in their pants. Thankfully, the sidewalk itself was deserted, and it was only the passing cars she had to focus on.

It didn’t take long for a busted, red Ford Explorer to stop and park next to the curb.

The passenger-side window rolled down, and Sapphire poked her head inside while ensuring the driver got a great view of her breasts. Sapphire and the driver began conversing in low voices. Chrissy was unsure of what to do, so she continued posing from a distance, though her chest fluttered rapidly. She knew the driver of the Explorer was bartering with Sapphire for Chrissy’s body like she was a piece of meat behind the counter.

After a short time, Sapphire stood upright with a devilish grin and a wad of cash in her hand. She met Chrissy’s gaze and nodded. Chrissy drew a sharp breath. This was it. It had all led to this moment. One of her holes had been purchased!

Sapphire pulled Chrissy towards the alley while whispering into her ear, “This nice man gon’ glove up an’ use yo’ front door, aight? He payin’ good money fo’ a ride so jus’ lay back’n have fun.”

They stopped midway through the alley and waited as the man backed his Explorer between the walls, further blocking the view of the street. He stepped out, and Chrissy got her first look at the man whose penis would soon be buried inside her.

Chrissy squinted and stared at the man a little closer. He had scruffy facial hair and hardened, calculating eyes. The man was tall and appeared to be in decent shape. He wore a heavy coat, jeans, and a confident smirk. Chrissy felt an immediate rush of relief at the initial sight of him. She wasn’t very attracted to him as he was a white guy, but at least he wasn’t some crazy serial killer. That being said, he looked strangely familiar… Where had she seen this man before? She gasped lightly upon realizing—

It was Deputy Ryan!

Was he undercover? What was he POSSIBLY doing here? Was he here to arrest her for whoring herself out? She couldn’t possibly be that unlucky for her first time, right??

Deputy Ryan stomped through the alley while staring holes into Chrissy. He looked downright sinister! A wild glint in his eye made Chrissy shiver and question if he was really here as a police officer. Did he recognize her? It had only been a week since they last ran into one another, so he must know it’s her, right? Did Sapphire not know he was a cop?

When he finally neared, Sapphire tugged gently at Chrissy’s sparkly, pink boob tube and let her barely restrained tits explode outwards.

Sapphire cooed, “She all ready fo’ you, mistuh. Tame this ho’s lil’ pussy!”

Deputy Ryan grinned and snatched Chrissy’s fingers into a vice-like grip. His heavy hands easily dwarfed Chrissy’s delicate ones. He was a gigantic wall of muscle compared to the short, dainty frame of Chrissy, and she could feel every iota of that inequality.

Trying to calm her nerves with conversation, Chrissy began to speak shyly, “Um, hello, I’m Candy, and I—”

His grip suddenly tightened, and he grunted coldly, “Save it, slut. I don’t fucking care.”

Chrissy sighed but nodded. He clearly didn’t want any type of meaningful connection—he just wanted access to her body. Deputy Ryan pulled her into the indent, and Chrissy felt her heart rate spike and her legs quiver. The dirt-coated floor of the indent and the faded green sheets on the mattress met her glazed-over eyes, and she gulped. There was no turning back now. Stalling with conversation wasn’t an option. She was about to have Deputy Ryan’s cock inside her in this secluded, ghetto alley!

He released her hand and left her standing next to the mattress. Deputy Ryan began tearing off his clothing, starting with his heavy coat. Chrissy shifted uneasily in her heels, though she kept her yellowed smile stretched across her face. The last thing she needed was to arouse suspicion because if Deputy Ryan knew who she really was, things would probably get a lot worse. If he truly didn’t recognize her, she needed to keep it that way. Pretending to be the eager, drug-addled prostitute she appeared to be might be her best course of action.

To that end, Chrissy gently shook her shoulders and allowed her bare tits to jiggle enticingly. She needed to keep his attention from her face! Just as she’d hoped, Deputy Ryan’s eyes widened and shifted to her hypnotic mammaries. He managed to continue stripping himself without breaking his stare. Each article he removed brought Chrissy one step closer to inevitable sex.

Despite her misgivings, Chrissy couldn’t help but evaluate each inch of Deputy Ryan’s body as he uncovered it. She may not have been super attracted to white men, but she was still attracted to men in general and felt a stirring between her legs as his seven-inch erection swung out when he finally dropped his boxers. His body was thinner than she expected, and she slowly traced her glassy eyes up his fit form. To maintain his attention, she cupped her long, acrylic hands around her tits and moaned softly while squeezing. The manipulation of her breasts sent a small jolt of heat to her crotch, where it joined with the lust already building from simply seeing a penis and the residual arousal from being fondled in the liquor store. The resulting dampness was a welcome feeling because she didn’t suspect Deputy Ryan would engage in much foreplay.

When Deputy Ryan was fully unclothed, Chrissy’s suspicions were confirmed when he pointed to the bed and ordered coldly, “Get on the bed, slut, and open your legs. I like to see a product before I use it.”

She didn’t like being ordered around or referred to as a ‘product,’ but Chrissy didn’t see any alternative to total submission, so she dutifully fell back onto the mattress wearing a yellow smile. The rusty creak of old springs was there to meet her fat ass. She drew a heavy breath and tried to calm herself, but looking over her mountainous tits and seeing a naked cock was not helping. Her eyes flicked to the alley where she watched Sapphire casually pace and act as a lookout.

Deputy Ryan crouched down to his discarded coat and procured a condom.

Unsure if she should be offended, Chrissy watched apprehensively as Deputy Ryan tore open the package and unfurled a slippery sheath down his length.

Noticing her mood change, Deputy Ryan scoffed, “Did your stupid ass really think I’d fuck your cunt without a condom? Daddy’s prick doesn’t touch diseased hooker holes, okay?”

Remembering how she looked at where she was, Chrissy shrugged. It made sense because Deputy Ryan believed she was just some unknown prostitute in the ghetto. Why should he trust that she was clean when she looked anything but? Still, it wasn’t a nice feeling to have an imminent sexual partner demean and insult her.

Deputy Ryan turned and pointed his virile cock towards Chrissy’s fertile cunt like a torpedo.

He used his foot to flip up her crusty skirt and expose her moistening slit. Chrissy laid back on her long, greasy hair and parted her legs to give him the best possible view. A few sticky strands bridged her labia, and the stench of female arousal wafted from between her thighs. Deputy Ryan smirked as he dropped to his knees and positioned his condom-coated cockhead directly in front of her vulva.

Chrissy held her breath and peered over her tits to watch as Deputy Ryan thrust forward and slid his penis inside her. She felt his rubber-coated flesh penetrate her vagina, brushing against her clitoris. The feeling of a real dick was different compared to her routine dildo insertion. While the dildo filled her, the silicone was stiff and cold. On the contrary, Deputy Ryan’s penis was warm and, while very erect, still somewhat yielding and pliable. While she yearned for the unprotected texture of a man sliding inside of her, she understood that Deputy Ryan felt the need to protect himself from a ghetto whore’s pussy. Chrissy gasped, feeling the ribbed condom grind against her inner walls. His girthy length filled her completely!

He withdrew and thrust once again as he started deeply and rhythmically fucking her. Chrissy laid her head back and moaned, imagining Deputy Ryan as a muscular Black man. His dickhead was thicker than any of her toys, and, once fully inserted, his erection pounded her cervix directly. She could literally feel his flared, condom-covered head thumping her deepest recesses and sending shockwaves of tingles through her body, especially considering her mind was awash with fantasies of black cock. Her high-heeled toes curled in anticipation of an orgasm. Warmth and horny energy surged through her body while Deputy Ryan grabbed her thighs and used them as an anchor to bury himself all the way to the balls.

“Y-You like that, you f-fucking ugly whore?” Deputy Ryan panted.

Chrissy listlessly scrunched the bedsheet in her hands and answered with a wild moan, “Y-yes! I *moan* l-love ugh—you’re, like, gigantic cock!”

Towering over Chrissy, Deputy Ryan began short-stroking his thrusts and maintained a consistently deep insertion. His heavy testicles slapped against her tiny female gooch and threatened to unload into her ovulating womb. Wanting to extract maximum pleasure from the situation, Chrissy skillfully tightened her walls against Deputy Ryan’s cock, causing him to grunt and pant into the ceiling.

The sounds of heterosexual sex echoed along the walls with deep male grunts and breathy female moans alongside the soft *squelch* of opposite genitals meeting again and again. Chrissy’s pleasure was mounting, but without an African king to dominate her, she could only get so aroused.

“Take it! Take it all, bitch!” Deputy Ryan spat while throwing back his head and plunging all the way inside.

Chrissy was keenly aware that Deputy Ryan was orgasming, not only from her experiences as a high-school slut, but also because she could feel his balls contracting against her asshole. She purposefully shook her legs and released a calculated scream while contracting her vagina and simulating an orgasm.

“Fill me up, stud!” Chrissy yelled, fulfilling her role as a wanton prostitute.

The tightening and loosening of her inner muscles worked to milk his ejaculating dick, but she just couldn’t get there herself.

Midway through Deputy Ryan’s orgasm, however, Chrissy suddenly felt an explosion of warmth and a rapid fluttering in her chest. An electric cascade of arousal rocketed from her pussy, and she gasped as a very real climax crashed through her system like a jet plane. Her body convulsed in pleasure, and she released a very genuine, breathy moan into the alley, joining Deputy Ryan’s masculine grunt. She was completely blindsided, as this feeling generally only came while she was swallowing semen, but her mouth was currently empty. But...that meant….

“Oh, fuck!” Deputy Ryan and Sapphire both yelled at the same time.

Lost in her lust, Chrissy rocked her hips back and forth while nonchalantly turning her head to peer towards the alley and see what Sapphire was yelling about. Sapphire was slowly backing up and staring towards the strip mall side of the alley while holding her hands up. Chrissy heard a male voice screaming and watched Sapphire drop to her knees.

“Fuck, fuck, fuck,” Deputy Ryan muttered before his panicked voice heightened, “Please tell me you’re on birth control!”

Chrissy lazily raised her head to see what the fuss was about. She saw Deputy Ryan’s softening cock was glistening with a combination of male and female juices. The condom was broken! A strand of thick semen connected the tip of Deputy Ryan’s erection to Chrissy’s quivering vagina. He pulled further away and broke the strand, but the damage had been done. Chrissy’s unprotected, ovulating pussy leaked a river of virile seed.

A group of uniformed police officers swarmed the area as Chrissy weakly giggled to Deputy Ryan, still basking in the afterglow of an orgasm, “N-no, I’m, like, not on any birth control.”

He hurriedly began dressing while swearing, “Fuck, fuck, fuck!”

A familiar female police officer stood over Chrissy and watched as she writhed pleasurably into the mattress.

Trooper Abigail turned and frowned towards Deputy Ryan, who was still making himself decent. Her gaze traced back to Chrissy, whose leaking womanhood was still fully on display between her open legs and beneath her flipped-up, crusty skirt.

She spoke down in a stern, commanding voice, “I’m Trooper Crenshaw. You’re under arrest for soliciting prostitution. What is your name, ma’am?”

Chrissy’s head was still in the clouds, but even there she knew not to give her real name. Both Trooper Abigail and Deputy Ryan would add this incident to the ongoing investigation!

Noticing her hesitation, Deputy Ryan growled, “Tell her your fucking name, whore!”

Trooper Abigail shot Deputy Ryan a scowl while Chrissy quickly answered, “Candy. Candy, uh, Valentine.”

Trooper Abigail offered Chrissy a hand and pulled her to her feet. Chrissy stood unsteadily and felt Deputy Ryan’s wad continuing to drip down her thighs. He’d stuffed her with quite the load, and it splattered quietly to the ground.

A pair of pink handcuffs were soon adorning Chrissy’s wrists behind her back before Trooper Abigail led her away from the indent. All manner of male eyes fixated on Chrissy’s exposed body. Her tits were still overflowing her top, her barely covered genitals were sore and clearly leaking, and her general appearance perfectly fit the stereotype of a drug-addicted whore.

A second female officer was standing off to the side, and Trooper Abigail paraded Chrissy towards her. Chrissy craned her neck and saw Sapphire in the distance with tears streaking down her cheeks as she was loaded into the back of a police cruiser. The cruiser door was shut, and the vehicle sped off.

Trooper Abigail spoke plainly, “Miss Valentine, please feel free to squat and relieve yourself to prevent a UTI and clear out Deputy Ryan’s...material.”

Chrissy looked over her shoulder and saw at least four male officers pretending not to pay attention to her. Two were standing with a fully clothed Deputy Ryan. He appeared to be recounting the details of their encounter.

Feeling an uncomfortable pressure in her nether regions, Chrissy followed Trooper Abigail’s advice and squatted down in the alley. Experiences in her past were more than enough to convince Chrissy that UTIs were no joke and urinating after sex was vital. Balancing on her heels and wearing handcuffs, Chrissy relaxed her bladder, and a golden stream erupted from her slit. She blasted the alley with an unfocused, leaky stream straight down from her skirt. While her genitalia was covered by the skirt, it was abundantly clear that a vagina was hidden beneath it because it was impossible for a penis to procure a stream straight down without a hand to aim it. Her thin, watery urine mixed with the thick cum still hanging around and made a real mess of things.

Chrissy noticed the male officers catching glimpses and felt her cheeks burn as a rousing laughter erupted from Deputy Ryan and his friends. He was probably telling them how tight she was or how eager she was while they viewed her struggling with the aftermath. It didn’t help that her chest was still hanging out!

When she was finished, Chrissy stood and turned back towards the female officers. Her crotch was still soaking wet, but there was nothing she could do to properly wipe. Trooper Abigail escorted Chrissy to her patrol vehicle and stopped.

She asked, “Miss Valentine, I’m going to conduct a search of your person. Do you have any drugs or weapons on or in you?”

Chrissy shook her head, and Trooper Abigail snapped on a pair of rubber gloves before beginning a very brief, cursory search. There wasn’t much to check, though she did take the opportunity to assist Chrissy’s tits back into her top. For her part, Chrissy stood and opened her legs a bit wider when Trooper Abigail requested it. The realization suddenly struck as Trooper Abigail’s gloved finger gently probed Chrissy’s labia: She was being arrested for prostitution! The words had not quite registered until the trooper's fingers were inside her lady bits, searching for drugs.

Chrissy whimpered, “What’s going to—what’s going to, like, happen to me?”

Trooper Abigail snapped up, and her eyes shifted to Chrissy's face. Did she recognize Chrissy’s voice!? She was examining her closely. Thankfully, the yellow teeth, greasy hair, and obvious signs of heavy drug use were enough to fool Trooper Abigal, and after a few seconds, she spoke, “I’m sorry, Miss, you just sound like somebody I’ve dealt with a few times. You’ll be brought to the jail and processed like all the other prostitutes we pick up on stings like this. Your friend went ahead of you already.”

Trooper Abigail secured Chrissy’s cuffed arm and led her to a nearby patrol car where a male deputy was waiting.

She spoke to the deputy in a friendly but professional tone, “Kevin, this is Candy Valentine, who has been cooperative with me so far. Already got a search on her, but I haven’t run her yet. Fair warning: Deputy Ryan filled her vagina pretty substantially. I tried to get her cleared out, but I think a towel on the seat might be a good idea. Up to you.”

Kevin sighed and nodded before speaking in a friendly but very ‘over it’ tone, “Thank you, Abigail. We work with so many goddamn perverts. The king pervert is working the jail tonight, and I’m sure he’ll love a newcomer.”

They exchanged an exasperated glance. Kevin opened the back seat of his patrol vehicle, where Chrissy saw what barely constituted any further description than ‘cage with a seat belt.’ Kevin motioned for her to enter, and Chrissy did so, noticing a cheap towel was already draped across the ‘seat.’ She scooted her butt onto the towel and tightened her thighs together while struggling to find a comfortable place for her cuffed hands. The remnants of Deputy Ryan’s semen dribbled onto the skirt and added to the crusty stain already present from Sapphire’s previous antics.

Kevin finagled the seat belt over Chrissy’s tits, which had already jiggled back out from her boob tube. He pretended not to notice, opting to begin the journey to the jail over manipulating an arrestee’s clothing. He got into the driver’s seat and used his radio to relay Chrissy’s fake stripper name and age to Dispatch. He estimated Chrissy was twenty-two, which she took as an insult. It seemed that drugs added a few years to the equation.

The real confusion came when Dispatch returned “Candace Valentine” as a valid eighteen-year-old girl. A serious case of déjà vu rippled through Candy as her identity was confirmed. What were the odds that there was a real eighteen-year-old girl named Candy Valentine?

While Candy’s brain grappled with the astronomical odds, Kevin called out his starting mileage and began driving the vehicle towards the jail. He turned his computer towards Candy’s cage, and she gasped at the picture displayed on it.

“This you?” He asked.

She saw her smiling (thankfully sore-free) face with the words ‘VALENTINE, CANDACE RYLEIGH’ beneath it. She also saw the number ‘18’ next to the name.

She stammered, “Um, y-yeah. That’s me.”

Satisfied with her confirmation, Kevin turned the computer back towards himself and continued down the roadway. Candy watched the dilapidated buildings go by, cringing as another squirt of Deputy Ryan’s spooge leaked from her ovulating pussy and absorbed into the towel nestled beneath her ghetto ass.

She frantically wracked her brain, wondering how in the hell she was going to explain all this to her mother.

32. Week 8 Part 6

LARISTOPA

32. Week 8 Part 6

33. Week 8 Part 7

31. Week 8 Part 5

LARISTOPA