Willa didn’t miss a beat when she cast a glance around the edge of her folded bonnet at the pair of conservatively-dressed women who had just tiptoed into the dimly-lit alley. In lieu of a greeting, she decided to instead use her lipsticked-purple tools of the trade to slop on a fresh coat of ooey-gooey, bubbly spit onto the curved pipe she had sliding back and forth across her tongue.
As her messy, red-headed braids bounced off of her shoulders while she worked, Willa started to amplify her performance for the bolstered audience. She arched her back inward, pushed her hips backward, and got lower down on her haunches so that her pasty, freckled booty would jiggle every time her lips sloppily smooched the base of the glistening cock pistoning inside of her slobbery mouth. Within the warm and sticky confines of her cockpolishing vacuum chamber, Willa ran her tongue up along the underside of the rock-hard kielbasa that she was servicing with the practiced pomp and circumstance only a professional like herself could execute. She flicked her eyes up and batted her lashes seductively at her client just from under the upper lip of her traditional Amish black bonnet – looking only somewhat contradictory to her current circumstances. As expected, she was rewarded with the arching, strained eyebrows and dropped jaw of yet another suited businessman about to pay her extra for blowing their load onto her face instead of the previously-shaken-upon throatpie.
Having worked her please-glaze-my-face-mister magic, she watched the telltale gesture of her customer’s hand drifting down to the base of his cock and prepare to dislodge it from the vacuum-seal of her mouth. After a wet ‘pop!’ that reverberated off of the dirty brick walls comprising the romantic venue, Willa found herself face-to-dick with a slippery pecker receiving a hurried one-handed wax job. In anticipation of the fruits of her gurgling labors, Willa licked her lips. Knowing she’d have a moment before she had her pale, freckled face painted white, Willa glanced down the length of the dingy alleyway so she could eye up her two newest onlookers. One of the two she recognized immediately as her kid sister. Edna still looked chubby and embarrassingly eager, and dressed in what was clearly her attempt at a ‘slut’ getup: A hand-sewn red dress dress that, in despite sporting a plunging neckline that showed off her well-endowed chest, otherwise, more closely fit the profile of a ‘night gown.’ Perennially Willa’s biggest fan from when they were girls, she noticed Edna had failed to catch a dribble of drool that ran down from the corner of her agape mouth. Willa rolled her eyes.
Willa wasn’t acquainted with the other girl, and from the looks of it she might never get the chance to change that. The poor thing looked as though she may turn on a heel at any moment and scurry her way all the way back over the hills and dells, back to the seven-hundred strong Amish community the three of them came up in. Her blonde hair was neatly tucked back into a ponytail beneath her head covering, which meant there was nothing to hide her timid gaze and flushed pink cheeks. A couple of her pearly whites were sunk into the plump bottom lip that she was nibbling on anxiously. The prayer covering overtop her hair was undone, though, so at least she was trying, Willa conceded. Just as she parted her lips to say something to the rapidly shrinking blonde, Willa was immediately greeted by the salty-sweet and utterly familiar flavor profile of a rope of milky Englisher brand spunk. She lived for the the feeling of it’s Elmer’s glue consistency melting across her tongue as it was in that moment. A chill ran up her spine.
“Mm-pfh– Fuck yes, cum on my face...” Willa groaned as she whipped her focus back onto the man she was supposed to be doing some contract cocksucking for. She could hear an audible gasp from her captive audience that she strongly suspected was from her newest blonde fan girl. She didn’t blame her for the surprise. “Cum on my face” isn’t exactly a commonplace turn of phrase from their shared hometown, and was probably the first time the poor dear had ever heard such manner of vulgarity, Willa surmised with a grin. The blonde girl’s gasps of awe multiplied while Willa’s smile widened into an open-mouthed, tongue-out “Aaaah!” as her customer’s throbbing cock ultimately unloaded up across her face. Wondrous ropes of white flew fast past Willa’s vision, which soon became impaired by a lengthy line of man-gravy streaking over one eye, the gooey glaze gluing one of her painted eyelids shut. More of Willa’s milky reward splattered against her lolling tongue, sperm-spackled her freckled cheeks, and even criss-crossed against her forehead. The bulk of the man’s busted nut, however, wound up flying too high – just shy of the tempting target that was Willa’s face. By the time her mark finished his business, relaxed, and slumped back from the kneeling knob-rocker, the whole underside of Willa’s black bonnet was dripping with the man’s spent seed. Sticky stalactites of semen oozed down from the headpiece’s brim to further fertilize the smiling slut’s well-glazed face. Willa took a deep breath and plunged forward, deepthroating the freshly-spent meat down to the man’s lipstick-stained balls. The effect, expected as it was, never failed to please the working girl.
“Ooooooh-FuuuUCK! E-easy girl, easy! Aaah…” crooned the sucked-off suitor, knees knocking under the sudden sensation of his sensitive, post-orgasm schlong thusly consumed. Willa did take it easy on her way back up, but couldn’t resist both curling her plump lips around the client’s cock and applying solid suction, evidenced by her sunken cheeks, all to ensure the man’s meat was left nice and clean following the fervent fellatio. After she let the juicy dicktip ‘pop!’ free from her purple-painted lips, Willa planted one last wet kiss to the underside of the slowly-softening shaft; a farewell treat to the satisfied customer, along with a handy wet-wipe to clean the many layered rings of the redheaded whore’s dark lipstick from his spitshined tackle. The task at hand completed, Willa relaxed off of her arched feet and down onto her knees, turning her head once again to smirk at the blonde.
“What’s the matter, honey? Never seen someone get a facial before?” She began, her tone of voice saccharine. It was plain to see the salacious show she’d put on had made quite the impression on her two new gal pals — Edna stared with a lustful twinkle in her eyes, tongue dumbly licking her trembling lips, while the blonde girl had turned away entirely, gaze cast to the ground (but from her beet red face, Willa was sure she’d seen the bulk of her knob-polishing performance).
“Look, if you can’t even watch me working, I’m not sure why you came he– !”
Her chiding was cut short by a hard leather sole pressing into the back of her covered head and the ground rushing up to meet her face. The side of her face impacted the ground hard enough to fuzz her vision and elicit an involuntary whelp of pain to escape out from between her recently-used set of cockpillows. A set of hands wrapped their way around her hips and dug into her supple skin as if they were a pair of handles affixed to the rented-out attraction between her legs. Her entire lower half was wrestled higher up in the air, and Willa had been in the ‘getting fucked in an alley’ business for long enough to know why they wanted her face-down, ass-up. An echoing “crack!” accompanied the stinging five-finger greeting delivered to her pale ass cheek. All in the same flurry of casually-delivered roughness, an unseen hand rifled up the sensitive flesh of the inside of her thighs and a thumb rubbed across her aching slit.
“Nnh...” Willa moaned through gritted teeth when she felt a pair of fingers dive into her wet hole, and, apparently satisfied with what they found, quickly retracted only to be replaced with the familiar-feeling shape of a swollen cock head. Her second client of the evening rubbed the swollen mushroom tip of his member up and down for a moment before lining himself up the inviting fucktunnel he had paid for.
“Hold that thought, honey,” Willa remarked to the wide-eyed, but still bright red blonde who had just watched Willa get pile-driven into the gritty concrete of the back alleyway. The timid girl nodded in a slow, trembling response.
“Shut up, tramp. We’re not paying you to chit-chat with your little friends,” she heard a voice say down to her from behind. Without another word from the man about to mount her like a breeding stallion, she felt his pair of hips smash viciously into hers. A heavy pair of swinging nuts smacked against her stomach. Naturally, all this commotion was accompanied by her pussy stretching to accommodate the hot injection of man-meat she had just been given. Willa let out an unrepressed moan of ecstasy; this guy was big. As her vision cleared, she found herself once again watching the meek porcelain doll, a picture of upright Amish ladyship. The blonde watched on with a crystalline blue-eyed fixedness at Willa. Every thrust from behind jostled Willa forward, and grinded her down into the pavement as she got herself thoroughly dicked. Between the three raging hard-ons in the makeshift debauchery dungeon, Willa figured she was probably going to make a handsome couple of bills for her trouble. This one, though. This one made the whole outing worth it.
“Who are they, anyway, bitch?” the gruff, gravel-voiced suit said down to her mid-thrust. Apparently Horse Cock expected Willa to both take his bitch breaker of a wang and have a pleasant chat at the same time.
It took Willa a moment to collect herself in between each of the unladylike noises pouring out of her mouth – noises that that kept her blonde fangirl blushing. Eventually, she was able to choke out a response.
“Well, one of them – oh-f-f’huck– !“ Willa let slip, unable to say much else when her current customer saw fit to remove the polished loafer from the side of her head and impart several cervix smashes with the cast-iron battering ram he using to tear up her insides. “... one of them is my baby sister. The other one, I’m not so sure. They’re both visiting from out-of-town on their Rumspringa.” After a beat, she added “... it’s an Amish thing. It’s their first time out in the real world – they’re basically tourists, seeing how the world works and whatno—aauught…!”
While Willa trailed off into another bout of reflexive moaning spurred by her current customer’s rough humping, a different voice spoke up in the alleyway. “The fat one looks like she’d line right up to take one of us on. Is she offerin’?” Willa barely caught sight of the man through her rhythmically disrupted vision as she received her animalistic rutting from behind. The cocky sales executive waiting his turn to plow the half-prone prostitute reached up to run a thumb across Edna’s ruddy, plump cheek. Willa heard her sister pipe up in response.
“I– “ Edna started, stammering hard, “I– mean, I could b–”
Willa cut across the possibility of her sister achieving gainful employment as she stifled a moan in order to shut her sister up.
“She’s not for sale.”
Edna’s voice caught in her throat and her brow furrowed, glaring down at Willa while she watched her older sister conduct negotiations with an Englisher’s bone buried balls-deep in her dripping snatch. Willa watched as the hopeful fellow pulled back from Edna, dropping his hand back to his side with a shrug.
“Have it your way, Willa, but if I were to give you some advice, entrepreneur to entrepreneur...” he said, pivoting towards her and striding in her direction. The man squatted down and looked her in the face. “You really ‘ought to be making use of those two — valuable assets, y’know? There’s a couple’a guys on my floor who’d pay handsomely for a full-time cocksucker working under the table. I’d offer you the job, but you look better drooling all over the concrete like this.” Willa scowled at him as he patted her upturned cheek condescendingly.
All the while, the man making full use of her full-service rear end maintained his steady back-and-forth rhythm as he fucked his happy way ever-closer to Willa’s next payout – a payday prefixed by a sticky wad of gunk deposited deep in her guts. Mercifully, she was able to push herself from up off of the grimy pavement and prop herself up on her other two ‘legs’ while continuing to have her pussy pummeled like a bitch in heat. Deciding to act in the spirit of her unsolicited business advice, she reached back with one hand to spread her freckle-speckled pair of callipygian cheeks and confirm the suspicion she had been harboring. Her latest client was trying and getting away with barebacking her. This gave Willa pause. She glanced over at Edna and blondie and pursed her lips. If Willa wasn’t also conducting “Whoring 101” in a grungy back alleyway behind a couple high-rises while receiving the combined best efforts of three horny businessmen to fuck her senseless, she might have let this one go. But class was in session, and with the patience and responsibility of an educator, Willa spoke up.
“Riding raw will cost you extra, stud. Got that?”
Her teachable moment didn’t exactly land the way she had expected it to. Instead of the anticipated head-nodding acknowledgment that the rules would be followed, she received a response in the form of a few fingers stuffed into her uppermost cock-accepting orifice.
“I believe it is my turn, Mr. Hamlin,” she heard from a dark, dulcet, buttery voice originating from the otherwise unoccupied end of her would-be spitroasting.
She choked down the rude, tonsil-tickling digits with a glare until they were kindly removed from her twitching gullet, followed by a gentle tapping on the tip of her spunked-up bonnet. She swivelled her head back front-and-center to unexpectedly align her mouth with the next rod ready and able to abuse her throat. This schlong in particular, as indicated by the noticeable lack of lipstick smears and ebony complexion, was the only knob remaining that she’d not slobbed — indeed, that hadn’t indulged in anything on Willa’s menu that evening. Both of her fiery braids were gathered up in a single, colossal, oven glove of a hand, and, forever the professional, Willa let her cumstained tongue fall out of the front of her face to accept the incoming invasion of the as-yet unsucked shaft.
“It would certainly be in your best interest to make it a messy one, whore,” the voice floated down to her. The guy had a voice for public radio, and a cock that sexually-repressed suburban housewives only dare dream about (though his brand of authoritative vocal stylings probably were dreamt about as well, Willa mused).
“You see, I’m not interested in the sloppy seconds from my business partners, here. Thusly, I will be partaking in something we have yet to take from you this evening.” Before Willa could even remark about how gentlemanly the dusky debonair was, she felt the thick slab of dark chocolate pushing past her lips. Willa started bouncing back and forth between her pair of rock-hard obligations she was charged with that evening. Heeding his politely-delivered advice, each time Willa would see-saw herself between either ends of their Eiffel-towering, she made sure to open up her throat and blow bubbles of throatlube down the entire length of his quickly gooed-up black baseball bat. Within a matter of moments, she had her homemade fuckslime caking every exposed inch of meat and dribbling down from her chin to the ground below her.
“I think you will find that your efforts will make what is about to come next all the more easy,” the man said down to the top of her head. Having apparently had his cock contentedly messied, Willa felt the palm of the charming black man’s hand rest on the top of her head, and his fingers grip her entire skull like a regulation-sized basketball. He carried her head backwards and dislodged the skillfully spitpolished shaft that was previously buried in her throat.
“Prepare her, Mr. Hamlin,” her client said across to the his spitroasting partner on Willa’s business end. Finally able to put a name to the schlong, Willa felt ‘Mr. Hamlin’ unsheathe his sword from her plowed hole without a moment’s hesitation. She felt the same pair of mitts that has used her hips like handles attached to a fleshlight tightened around her shoulders. Willa was jerked up from the ground and planted on her wobbly legs. She hadn’t stood in at least an hour. Before she could blink, Willa was introduced tits-first to the gritty brick wall nearest her. She figured that if she had paid attention to what the sable-skinned individual had said to her, or what he had asked her to do for him, she could’ve put two-and-two together and predicted that he was going to pound her asshole. Unfortunately, she didn’t realize his intentions until his dick was lodged 6-inches deep into her unprepared back door.
“Ooh–! Ho-HOLY FUCK!” Willa shrieked, feeling his gutbuster wedge itself up next to her colon. Willa scrambled, pawing at the gritty bricks that were being used as a staging platform for her rear-entry rutting. It had been a while since she had a client willing to shell out the extra dosh on her puckered butthole, and even longer still since she had someone take it without so much as a ‘by your leave.’ The man who was previously making mincemeat of her currently unoccupied but nevertheless beaten-up cockhole had her pinned to the bricks with the back of his forearm. She wasn’t going anywhere. She was going to be this gentleman’s piece of ass – an ass wrapped around his cock, no less – whether or not she wanted it. Fortunately for her, once her O-ring had relaxed to accommodate his beast, she most certainly did. Her grunts of discomfort laxed, and her jaw started dropping lower and lower to make way for the stream of unashamed moaning rushing out of her mouth.
“Oh, god, okay...” Willa breathed. “Alright, fuck, give it to me…” she slipped in, her words bookended by a pair of shrieking moans. “Pound my fucking ASS!” she croaked. Those words, apparently, were the cue for her beefcake restraint to relinquish her from the burly, grizzly arm that he was using to nail her to the wall. He knew she wasn’t going to go anywhere now. From “hold her down” to “what a buttslut” in 30 seconds? Willa tallied that factoid on her mental leaderboard as a new record. As he cleared out of the way to retreat back into the inky shadows of the alleyway and allow his superior to have his way with this Amish hooker’s tight tailpipe, Willa heard a tinny voice squeak out from somewhere in the direction of her fan club.
“ –-dick in her behind? Does that feel different than– Well, y-you know, the other way...”
“I mean, like, y-yeah, of– Of course it does! It’s like… tighter, I guess?”
Willa was able differentiate the two voices. The first speaker, noticeably interested in what was going on with Willa having her ass railed, was the blonde and blushing girl she hadn’t caught the name of. The other voice, sounding much more confident in something she didn’t know anything about, belonged to her kid sister Edna. Willa decided to try and supress her grunts of assfucking bliss to deliver another lesson. She inched each wobbly thigh out further and repositioned her legs into a wider stance, balancing precariously on the toe of her black pumps. With her hands flat against the brick and mortar, she grinded her pasty posterior backwards into the man hollowing out her bowels for his enjoyment. She eased him back gradually until she was fully bent over and using her hands as support trusses. Finally, she shook the hair out of her angled visage and bore her gaze into the enraptured blonde Amish maiden.
“He’s pounding my ass right now, honey, and it feels fucking fantastic,” she said with a tone of voice that dripped salaciously out from her lips. The blushing blonde nodded in subtle response. Her eyes were full-moon discs.
“Speaking of which, you dirty Amish whore...” she heard her chocolate lover intone from behind, his deep voice somehow piercing through the sound of his crotch slapping away at her backside and his belt buckle jingling somewhere half-way down her thigh. Willa felt him close his pair of two bear paws around her waist and give his deep-bowel mining drill a series of pointed thrusts. Judging by his prefixed comment, he accurately assumed exactly the effect the gut-punching moves would have on Willa. She felt her vision dim for a moment and her hips spasm involuntarily in the wake of his quickened pace and deeper strokes. Her knees threatened to buckle under the weight of such pleasure, but she was able to hold them steady, wobbly as they may be.
“You’ve got approximately three more minutes to enjoy your pleasure before I’m through with you,” the gruff buttfucker instructed. Willa wasn’t going to need all three minutes. Her hand drifted between her splayed legs and pressed firmly onto the pleasure button that was dying for attention. She massaged her hand back and forth, all the while taking the double-chocolate Toblerone deeper into her blown-open and gaped anal entry. In fact, it only took her another minute to climax. This time, her vision left her completely — fingers working her clit furiously while white-hot electricity shot up her spine, Willa came with a stuttering groan. She clung desperately to the brick wall as she lost her bearings on her surroundings, and her jaw hung open in a silent cry of overwhelming pleasure. Without consciously doing it, she stamped one jittering, trembling heel as she did her best to cope with her own crashing climax, cumming hard while her new favorite customer had his way with her tender, puckered starfish.
An indeterminate number of seconds later, Willa came down from the stratosphere and her vision gingerly returned from the void it had plunged into. She was just in time to appreciate her mandingo handler’s final lap around the all-anal track he’d mapped out using her ass as the canvas — the big black bull of a man blew curt clouds of breath between clenched teeth and flared nostrils with each stroke, barely letting more than an inch of his rectum-reaming pork sword slide free from Willa’s well-worn backdoor on each and every cheek-shaking thrust. The woman’s bubbly buttocks rippled from the ferocious fucking, pale flesh reddened from the ruthless rutting. After another manic minute of mind-blowing buggering Willa could feel herself warming up to another orgasm, but before she made any real headway towards it the man blasting her ass crossed his finish line with a loud, proud cry of:
Willa cried out herself, mewling like a blushing butter-churner as she felt both the black man’s body clench and curl inward over her arched back, and the warm, wet rush of bubbling spunk splurting out and down into her thoroughly-fucked ass. In her fleeting, fucked-silly, post-orgasm stupor, she hardly noticed her client doing his best to make it all the way up to the first left-turn up in her guts before he unleashed the contents of his balls into them. When she felt the deep deposit of sperm flood into her, she instinctively knew to clutch at her belly as it bloated ever-so-slightly with the newest deposit to the sperm bank that was her anal cavity. Upon finishing his donation, she could feel his girthy inseminator start to back its way out from her gooey hole. That feeling, alone, threatened to be enough to put her over the edge once more. Once he was fully extricated from her fucked-raw buthole, Willa cloaked a completely unintentional collapse to the dirty ground instead as a slutty sink back to her knees. Willa was a prostitute, and she was always on the clock, regardless if she wanted to pass out in the post-orgasm reverie.
She tap-danced around on her knees to reposition herself in front of her customer. Not unlike a post-dinner wet-nap, Willa began to run her tongue up from the fleshy folds of the big-dicked black man’s nutsack all the way up the underside of his shaft, and then down the other side. She bathed his vein-snaked meat in her spittle without so much as a thought as to where it had just been. Each swath of her tongue cleaned from the rod an inch-wide tract of spunk that hadn’t reached it’s mark along with whatever leftover spit-up Willa had used to lubricate his rod for her ass initially. It was during this after-fuck courtesy cleaning that Willa felt the man press his thumb into her forehead, still sticky from her first load of nutbutter earlier.
“That’ll be all from you. We’re done here,” spoke the bass-toned businessman before yanking his drooping member out from in front of her face, satisfied the streetwalker had sufficiently spit-shined it. Willa reached up to her forehead and felt the crisp edges of a handful of bills, and realized that she had just had her payment glued to her face. Slumping down so her doughy asscheeks rested on the back of her ankles, warm wads of jism oozing from her freshly-fucked rump, she watched the last remaining man stow his trouser snake and zip up his pants. Moments later, the three co-workers were halfway to the exit of the alleyway and already animatedly chattering about the next time they would get together to bond over a back-alley payslut. For the first time since the ordeal began, Willa was able to turn her attention to her guests.
“Alright, dears,” Willa began, fully aware there was presently a torrent of fresh splooge gushing out of her augered asshole, and plenty more applied thickly to her face; hopefully her whore’s warpaint would help her in the negotiations ahead. “You want to come work for me?”
Her query was met with two slack-jawed, wide-eyed nods from both Edna and her yellow-haired friend. Willa wasn’t exactly certain roping the two nubile newcomers into her disreputable day job was the right thing to do...but she hadn’t spent the last five years since leaving her Amish homeland turning tricks and sucking dicks in the city’s seedy underbelly to follow Christ’s example.