Sherry's New Job Ch. 03

The part of town Ray drove to was unfamiliar. He circled several blocks, trying to make out the notes Freddy had jotted for him on the napkin. Stopping at a red light, he glanced over to where streetlight illuminated a smaller side street. A couple of trashy looking streetwalkers leaned against a mailbox at the corner. He could see more girls further down the block, past the dim, flickering light that marked the entrance shack to an all night parking lot. Glancing up at the street signs, he realized this was the place.

Cranking the wheel, Ray turned on to the side street and into the parking lot, taking a ticket from a teenage kid that barely looked up from the flickering television on his counter. "Wait here," he said to Sherry, and climbed from the car, snapping the locks shut.

He walked down the darkened street, through the pools of light, until he drew near to the girls. "Hey baby!" one cried, "Are you lost? Looking for someone to hold your hand?" She was skinny, lots of blond hair piled onto her head. Sort of pretty, but she looked tired, worn out, the dark circles not quite covered with too much makeup. At first glance Ray would have put her age in the late-twenties, but as he drew closer he realized she was much younger, probably just eighteen, but already looking older, harder.

"I, uh, need to talk to Tommy."

Behind him, in the darkness of an alley, someone cleared his throat. Ray turned. "Tommy," he said into the darkness, "I'm Ray. Freddy's friend."

Teeth reflected the streetlight as a wide grin appeared in the dark, and a big black man stepped from his perch in the darkness. He stuck out his hand. "Yeah, man, Freddy told me you wuz comin' by. Lookin' for a good piece a'ass, are yah? Bad night, tho'. Two of my girls is out at a bachelor party. I just got Candy and Andrea left tonight." The two girls, the young blond and an older redhead, nodded to him. "You might say I'm a bit short staffed tonight."

"Well, Tommy, that sort of works out, because I'm here to help you with that. Freddy maybe got it a little bit wrong. What I've got is a nice little thing over in the car, and she needs some work for this evening. I don't even want any money she brings in. Keep it. Let's just say she's adding to her resume."

Tommy was obviously confused. "Well, Freddy said you was OK, but I just don't get the deal here, man."

"Simple. Here's how it is. This bitch has been giving me some attitude. I need her to remember that she can end up out on the streets as easy as the next piece of ass. So tonight I'm going to remind her. Here," said Ray, passing over the roll of bills and the paper bag, "Two hundred dollars, and this here's a nice bottle – 12 year old single malt. That should take care of your, ummm, management fees. Let her work the corner for you. If she turns some tricks, great, you keep the cash, free and clear. If not, you're not out anything."

"I dunno, man. I've gotta at least see her. Give her an interview, yah know."

"Not a problem. I'll go get her."

***

Sherry didn't understand why she was sitting alone in a car, in a near empty parking lot, this late at night. Ray had told her they were going out, and she had dressed up special for him, just the way he wanted. She knew she looked sexy, in a trampy sort of way, almost like the girls that were standing at the street corner when they turned down this street. If that was what Ray wanted, she was certainly willing to oblige. It had been a long time since she had dressed up for him. In fact, if you didn't count that blowjob earlier, it had been a long time since she did anything for him, she reflected.

The overhead light snapped on as the door beside her opened. Ray's hand thrust in. "Come on. There's someone you have to meet." She took Ray's hand and followed him down the sidewalk, towards the corner, where she could see the two girls, still lounging under the streetlight. At least the strange outfit Ray had made her wear wouldn't look out of place, she laughed.

As they approached the corner, a big black man stepped from the shadows of a nearby alley. Motioning her into the light, he eyed her appraisingly, head to toe and back again. Taking her wrist, he strode back to the darkness of the alley. To Ray, he said, "Yeah, she looks like she'll do. Little older than I'm used to, but a nice piece a' ass."

He turned to Sherry. "Yo, bitch! You workin' for me now. Me and your old man, we just made a deal. Raymondo, you gonna stick around?" Ray nodded. "Cool. Now you. Sherry. On your knees. I got some rules to be splainin' to you. My name is Tommy, by the way."

Sherry had no idea what the big man was talking about. All she could think of was that she needed to be on her knees, so she dropped down, confused. The big man laughed. "You don't need your mouth to be listenin'." Ray tugged down the front of his pants, his big dick coming free. In the darkness, Sherry didn't see it until it was resting on her lips. She opened her mouth dutifully, without thought, feeling Tommy's rigid penis push past her lips and begin rocking in and out, slowly fucking her face.

"You be chargin' $100 for a hand job; not many ask for that. $150 gets them a blowjob. $200 they go all the way. They wanna give you more, fine, but you hand whatever you get over to me. Understand? You always use a condom, no matter how much they offer. They got a car, tell 'em to park in the lot up the street. We got a deal with them, but you gotta cut the kid in at the end of the night. Got it?"

Sherry tried to make a noise around the flesh in her mouth, without much success, Tommy grinned and grasped her head again, resuming the rocking motion of his hips. "Oh yeah. That's it babe. Suck it good. Watch it with the teeth. Yeah that's better. Get that tongue movin'". Sherry fought to comply, her lips and tongue and cheeks massaging Tommy's shaft as he pumped it roughly in and out of her mouth, his bag slapping against her chin. With a lurch and a thrust, she felt Tommy's release, globs of salty semen splashing across the roof of her mouth. His dick slipped from her mouth and she was left there, kneeling in the darkness with a mouthful of some stranger's cum. Earlier with Ray, she had spit out his juice, but she sensed Tommy wouldn't stand for that. Closing her eyes, she forced herself to swallow, sucking in her cheeks and trying to conjure up enough saliva to rinse her mouth.

Tommy noticed what she was doing. "You don't got breath freshener? You be needin' some of that. Candy? You got some mouth spray you can spare? Good. An' give the girl some condoms." The blond came to Sherry, and, with a smile, dug in her purse, handing Sherry a handful of condoms and a small spray bottle of breath freshener. She took Sherry by the hand and led her to where the redhead lounged against the mailboxes.

"My name is Candy. This here is Andrea". The redhead nodded, blowing a puff of smoke in Sherry's direction. "Don't mind her. She's being a bitch today. Her old man slapped her around some today, but she won't admit it." The redhead shot a dark look at Candy, who responded with a finger upturned in an obscene gesture. "Anyway, they'll be back together by the end of the week, and it'll be old news. She probably figures you're gonna cut into her business, but I think there's enough work for all of us tonight." Candy grinned at her.

"It's not bad here. Clients are a pretty nice bunch. A lot of them are regulars. Be good. Don't piss off Tommy, and you'll be fine. Oops, gotta go!" Candy turned away and hurried to the side of a car that had just pulled to the curb.

Confused by the rush of events, and not sure what else to do, Sherry turned to the street and tried to copy Andrea's nonchalant pose.