Street Hooker Blues

Escort Confessions II: Street Hooker Blues

After the previous week's unexpected surprise, Harold has wasted no time sending over new attire for the new fantasy experience. Racquel excitedly opens the boxes and lays everything out on her bed, her pussy already soaked in anticipation. The first hint of what Harold had in mind: knee-high boots in cheetah print; similar to those she had worn in the porno, Silent Strangers, along with a short mink jacket, large hoop earrings of gold, a tiny black leather mini-skirt and some cheap black lingerie.

Racquel put it all on and spun around in her tri-mirror dressing room. Sure, she looked really hot and desirable, but not classy like last week - not at all. In fact, she thought she looked rather....trashy. Not that she minded one bit, but it was such a departure from the previous week. What on Earth did he have in mind this time?

Again, the limo picks Racquel up. Harold is inside waiting. He offers her champagne and compliments her on how she looks. Not surprisingly, the limo eventually gets off the freeway at a seedy part of town; covered in warehouses, crack dens and factories. This is truly a terrible section of the city Racquel had only passed by; usually crossing her fingers her car wouldn't break down. Now she was in it.

They pull up at a two-story brownstone-type building on a street corner. They step outside into the chilly night. They then approach the house, hardcore rap music echoing from some distant building. On the steps, a black guy who seemingly appears out of the shadows to greet them. He's dressed in a tacky suit, chewing on a toothpick - obviously attempting to make a big impression. Racquel struggles to not roll her eyes.

Harold introduces her to the short, black man whom she can now see is a pimp. Harold apparently knows him personally, which surprises her. The pimp, TJ, is decked out in a purple suit, fedora, boots and tons of tacky gold jewelry and a gold tooth. Harold explains he wants TJ take her in for the night as one of his girls. Racquel then gets it: a tumble down the ladder from high-class escort to trash; Harold wants her to reprise her street hooker role from Silent Strangers. A little stunned, she looks out into the foggy streets what lies ahead.

TJ listens closely to Harold's request. Naturally, TJ obliges, but insists on tasting the product first before buying in. Harold agrees and they go inside. It's very dark and filled with smoke. TJ takes Racquel upstairs by the hand. The three of them all enter into a nasty, sewer roach infested room the hookers obviously use multiple times a night. A heavily stained mattress with no covers has been pushed over to the far wall. Overhead, a single light with no shade illuminates the room along with some tacky neon from an adjacent bar. Harold finds a chair in the corner and drags it closer to watch his girl spread her legs for a bonafide pimp. TJ leads her the mattress and has her sit down on the edge. He takes her coat like a gentleman and hangs it on an old nail. He then sits next to her, placing his heavily jeweled hand of gold and diamonds on her shapely leg. She watches the hand slide up her mini-skirt. She lets out an aroused gasp as she flashes TJ a receptive smile. They are soon making out. TJ now has his hand on her pussy as they continue French kissing. He leans her back on the bed, pushes up her skirt and yanks off Racquel's panties. She opens her legs for him. He grabs each of cheetah print boots and spreads her legs even wider apart to look at her pussy. He shakes his head in disbelief. She smiles as she begins playing with her tits. TJ then dives in eating her pussy, fingering her and going down on her ass. Racquel stares at Harold as TJ sticks one of his jewel-encrusted fingers right up her pussy. Harold watches in fascination as the shiny rings disappear up inside Racquel.

TJ then unzips himself, grabs her by the head and pushes her down to suck his dick. He holds it there as she sucks away for several minutes. He then lets go, lies back and allows Racquel to show him what she's got. Racquel spends the next ten minutes licking and kissing his dick and balls, smiling the entire time. He then reaches under the mattress for a condom. He slips it on as Racquel watches on her back, waiting. He then climbs on top and presses his big dick against her tight pussy. Racquel reaches down and guides it in. TJ then begins fucking her as Harold watches, enraptured. She wraps her boots around TJ and blows kisses to Harold, egging on TJ to fuck her.

After a minute, Racquel notices several huge cockroaches on the mattress, getting closer. Not wanting to piss off her new pimp, she continues in motion with him, kissing and biting his ear. She then watches one of those sewer roaches disappear between her legs. She can immediately feel it crawling on her asshole as TJ continues to fuck. She bites down on his ear, hoping to bring him to orgasm. The roach then is on her pussy crawling around. Just then, the second sewer roach has discovered Racquel's asshole!

Racquel looks around, panicked; there are now dozens of sewer roaches on the ceiling, floor and mattress. TJ finally, cums, rolls over and peels off his condom, throwing it on the floor, exhausted. Racquel then flicks off the sewer roach staring back at her from her pussy.

TJ looks over at Harold as he rolls off the mattress, telling him, "The bitch can suck dick and has a tight pussy. And that face. Wow. The legs, pussy, ass -- she got it all. I'm taking her down to the street corner now."

Harold was very excited, jacking off without an once of shame.

TJ then takes Racquel out to a street corner wearing the mink jacket, super-short mini skirt and her cheetah boots. He instructs her to fuck anyone that drives up. $20 for head, $50 for a fuck. Harold stays close by in the limo making sure she's safe. Under the streetlamp Racquel is shivering in her mini-skirt. Two minutes in, a pick-up truck pulls up. The driver looks utterly stunned at such beauty. Racquel pivots around, smiling, showing off her legs and ass. The guy waves her in. Harold has the limo driver follow the truck down an alley. He sees the silhouette of Racquel's head duck down to apparently begin sucking off her guy. And so it goes for hours - one guy after another. She works a busy night, getting off construction workers, factory regulars, security guards, etc.

TJ eventually shows up and they split the cash. He kisses her and she gets in the limo.

Driving around, Harold and Racquel finally talk about the homeless guy who fucked her the previous week. She presses him if that was all staged. He tells her the truth: no. Racquel confesses she loved it -- but can't explain why. Harold summizes a great many pretty girls, sometimes even rich ones, enjoy the excitement of slumming it. He suggests it may just be part of her interracial lust, but then asks if she has a preference for tonight's continued games? She smiles, immediately feeling her tits getting hard.

They then agree to drive around looking for homeless guys for her to suck off. She leans back and begins masturbating as he watches. She tells him she wants 'nigger cum.' And the more she talks about it the more turned on she gets. She tells him she wants to suck 'nigger juice' all night.

Harold is a little stunned, but instructs the driver to drive down to the ghetto where the freeway intersects. The driver is extremely discreet with his master's desires and obeys without question or judgment.

She then sees three old black men camped out at an underpass, scattered with trash and turned over shopping carts. She winds down the window, leans her elbows on the edge and flashes them a big smile. Racquel then calls one to of them over from the oil-drum fire get-together.

A portly fellow with a grey specked beard, long coat and taped together shoes makes his way over, imagining he's being hit up for directions. He peeks inside and sees Harold observing the situation, but remaining silent. Racquel then flashes her eyes, and smiles seductively, edging a little closer as she flirts with the guy. She tells him they have food inside and would love to give him and his friends some money. His eyes light up and he gives his friends a quick thumbs up that everything is cool. The bum then turns to Racquel to continue talking excitedly. Nodding her head, pretending to listen, she eventually reaches over to feel his bulge without even breaking eye-contact. That stop him mid-sentence. She then unties his rope belt and pulls out his hairy dick. Racquel then leans out of the open window just a bit more and begins sucking away like there's no tomorrow. The guy takes a gander inside the limo and sees Harold calmly watching. The bum's mind is in shock, but hard as a rock below.

As before, Racquel begins cleaning off his penis with her tongue and spit. She lathers up the cock and swallows down all the sweat, piss gunk and pubic hairs that have gathered in his foreskin.

Harold now has a perfect view of her ass. He pulls up the mini skirt and proceeds to massage her ass and pussy as she sucks off the homeless fella -- whom he can tell stinks to high heaven. Pretty soon, the other two are gathered on each side of their friend, watching a beautiful white girl suck off a black dick. They begin egging her on. She gives them a smile. They then pull out their smelly cocks and moves in for some action. Racquel then goes to work sucking and cleaning off each cock. Harold is now really turned on as he continues to play with Racquel's now soaked pussy.

As Racquel continues sucking and jerking off her three hobos, Harold decides to pause the action, open the door and invite the men inside - but insisting they leave their filthy coats on the hood. The portly one with the beard sits next to Racquel and they begin kissing. Harold sits far away, observing the other two men. One an elderly guy in a dirty wife-beaters vest. The other is a stocky fella with a beer gut. Both are jacking off as Racquel makes out with bearded guy.

Harold pours the other two men a drink of Scotch as they watch.

After a few minutes of teasing, Racquel playfully pushes the bum away, giggling, lies on her back and spreads her legs for him. Harold then senses of moment of instruction is necessary before he lets the men fuck his girl. He asks that they save all cum loads for her face. Racquel then comically opens her mouth wide and points to it. They all laugh as Harold opens a box of condoms.

The limo really stinks now, so Harold leaves the windows down as he watches each bum climb on top of his girl and fuck her. He loves watching, but can sense she loves it even more. Addicted.

She passionately kisses each one, whispering 'fuck me nigger,' over and over. And they do. Like clockwork, they each pull out, move over to her gaping mouth and shoot their loads across her face, or directly into her mouth. She licks it all up Harold hands them each $50, some sandwiches and sends them on their way.

Harold sits across from Racquel, who is lying with her legs still open. Totally wiped out. They stare at each other in silence.

Finally, he says to her, "I guess we figured out what you're into now, huh?"

"Oh, and what might that be King Cuckold?" she replied with an air of sarcasm.

"Screwing hobos."

"Oh... that." And Racquel smiled deeply.