Sherry's New Job

Sherry knew what she was here to do, and had unexpectedly accepted it, yet she dreaded actually engaging in whatever sordid requests the clients might have. But as time wore on, she began to grow concerned. A string of cars had stopped at the curb, and Candy and Andrea had vanished, sometimes for just a few minutes, sometimes for longer. What Sherry didn't understand is why no one had approached her. She was sure she was still attractive, with a good body and welcoming smile. Yet still no one beckoned to her. She knew that many of these men were regulars, favoring their usual girls, but she was sure that couldn't explain everything.

"The trick," explained Candy, "is not to wait for them. If they stop, they are looking for company, so go to them. If they're looking for Andrea or I in particular, they will tell you. Let's try. Andrea is off with someone. The next car that comes along, I will hold back. He'll be all yours. Think you can do it?"

Sherry gulped, and nodded.

It didn't take long for Sherry to get her chance, as a small sedan pulled to a stop at the curb, the passenger window rolling down. Sherry looked at Candy, but she had retreated into the darkness of the alley. Straightening her shoulders, Sherry walked to the car, trying her best to add a seductive wiggle to her step; afraid she was instead doing a convincing imitation of a waddling penguin.

As she reached the side of the car, she leaned forward, into the window. Fighting the lump in her throat, she stammered, "He-hey baby. You, uh, looking for some, um, company?"

The man in the car didn't seem to notice her hesitation. In the darkness, she really couldn't make out much of the man belonging to the voice, but she could here his response. "Sure, How much?" Sherry repeated the prices Tommy had taught her, the driver grunting his ascent.

Not without some worry, Sherry opened the door and climbed in, directing the driver into the parking lot. As she came to a stop, she realized this client wasn't the best introduction to her new career, but she resigned herself to her task. The car stank of sweat, beer, and smoke. The driver snapped on the interior light, pulling out his wallet to count out the bills into Sherry's waiting hand. Ten twenty-dollar bills. Under the dome light, Sherry realized this man was about as far from her ideal as she could imagine. She could see the man's overhanging belly; sweat stained his dirty t-shirt. He hadn't shaved in days.

Prompted by his expectant stare, Sherry climbed from the car and slipped into the back, the driver following. Sitting on the seat beside her, he loosed his belt, tugging his trousers and underwear down. Sherry helped him pull them free, wrinkling her nose in disgust as she saw the long brown "skid marks" that decorated his briefs. With a resigned sigh, she popped a condom free from its foil, dropping her hands to the man's lap, pushing past his gut to his short thick erection, rolling the latex down over the shaft.

She leaned forward, dropping her face to the fat man's lap. To her horror, her nostrils filled with a telltale musky odor that told her this man had not washed his crotch in quite sometime. As her fingers pushed through his pubic hair, they caught in tangles that she realized was crusty dried cum, poorly cleaned up from a recent session of jacking off.

Choking back her revulsion, she pushed her mouth down, glad for the latex sheath that kept her lips and tongue from actually touching the dirty shaft. Though she tried to bob her head up and down without touching more than the condom covered head, the john had other ideas, pushing hard on the back of her head, forcing it down, the shaft ramming hard against the back of her mouth. Overwhelmed, she gagged, her throat spasming around the latex covered tool, her nose and cheek crushed against the dirty, matted pubic hair. She fought for breath until she felt his hands loose, and she lifted her head, gasping for air.

She wanted to flee the car, leave this grotesque pervert behind, without a backward glance, but something told her she couldn't do that, an insistent internal voice that overwhelmed any thought she had of not complying.. Instead of fleeing, she twisted around, pulling free her g-string and tugging her skirt to her waistband. The man beside her had reached out for her tits, mashing and twisting them blindly. She tugged her camisole up and over her head, hoping he would have better aim by sight. He did – instead of bouncing and flopping her chest about aimlessly, he zeroed in quickly on her nipples, twisting and pulling them painfully, in what he must have thought was some sort of seductive play.

Deftly disengaging her chest from his grasp, Sherry turned her back to the little man, and, holding his penis upright, she rocked backward until it slid into her. While this position gave her the freedom to control her movement, and spared her from facing him directly and closely, it still allowed him access to her breasts, and he grabbed then fiercely, holding them like they were handles. With each thrust and motion, Sherry felt a painful jolt from her boobs, bringing tears to her eyes. She knew she would get no pleasure from this, so she focused on working the man's dick as hard and fast as she could, pumping him hard, squeezing with the muscles of her vagina, trying to coax him to cum and end her ordeal. Unfortunately, he was small, and the angle was not the best, and he slipped free repeatedly. Reaching down, she held him in, cradling his balls, coaxing him with hand and pussy and words. "Oh yeah, lover! That's it! Oh I want you so bad! That feels so good!" she lied, trying to make him feel good, "Fuck me baby. That's what I want! Yeah! Oh do me lover. Do me hard!"

She kept that up, ignoring the pain of her bruised tits, until his hips bucked and his pelvis and balls went stiff, jerking until in a final convulsive spasm, he popped free, his dick thrusting between her thighs, the latex tip of the condom stretching until it burst with an almost audible pop. Sherry felt the hot gush of the man's putrid semen splash across her thighs, soaking her stocking tops.

Sherry slumped, scooping the jism from her leg and wiping her hand clean across the seat back. As she redressed, she realized there was no way she was going to clean the sticky mess from the tight black nylon, so with a sigh she peeled her stockings off, with a faint sense of disappointment. She had thought the stockings completed her ensemble nicely, and she worried she wouldn't look good enough for the next men, but there was nothing she could do now. She balled the tights into a small mass around the sodden remnants of the torn condom and tossed them into a trashcan as she exited the lot.