Sherry's New Job

After her bad first experience, things got easier. The next couple of men Sherry saw seemed normal. The first, a married man in his early thirties, was only interested in Sherry's mouth, looking to her for the blowjob he no doubt could not convince his wife to perform. Perhaps, thought Sherry, the guy felt that this was less of a betrayal than actually screwing her. After all, everyone remembered that, according to President Clinton, a blowjob was not a sex act.

The next customer was a kid from one of the nearby colleges, a shy, awkward nerd devoid of social graces. The kind of kid that spent all of his time in the library or on the Internet. She wouldn't be surprised if, in a few years, he was pulling in a six-figure income. A better wardrobe, contact lenses, some dental work, and a lot more self-confidence, he might be beating the girls off with a stick. Sherry had fucked him, but she had to lead him through every step along the way. He had even acted embarrassed to look at her naked breasts when she peeled off her camisole and lifted her nipples toward his mouth. She couldn't be sure, but she rather thought that she had just helped him lose his virginity.

The man she sat beside now – Todd, he had said his name was - was somewhat older, perfectly groomed and well dressed. She could tell just from the car - an almost new Lexus, gleaming, immaculate chrome outside, well-oiled leather within – that he was a man of money, refinement, power. All that she couldn't figure out is what he would be doing picking up a girl like her.

The thought chilled her briefly. She knew she really wasn't this sort of girl, that she should feel comfortable around wealthy people and expensive things. She couldn't explain it. Tonight she felt like a spectator in her own body. She didn't know why, but what she did know is that right now, the most important thing in her life was to please this man, to do whatever he needed.

"So, how much?" Todd asked.

"That depends on what you want to do," she answered. Looking at the car, she knew he could afford whatever he pleased.

"How much to fuck that tight little ass of yours?"

The answer stopped Sherry dead. She instantly questioned her judgment of the man. He hadn't looked like the sort of slimy, dirty pervert that was into that sort of thing. She could not imagine any normal person getting turned on by that... place. She could barely touch herself there to wash; she couldn't imagine anyone who would touch that dirty spot voluntarily, especially on another person. She certainly couldn't imagine anyone normal being turned on by such filth.

Then it hit her: she had no idea how to answer Todd's request. Tommy hadn't given her a price for that. She couldn't say no, so instead she quoted an outrageous sum, twice what he would pay for anything else. It didn't faze him. He flipped open his wallet, and calmly peeled a stack of bills into Sherry's shaking hand.

She had no other choice. She slipped into the spacious back seat, Todd following closely behind. She was still a bit numb, knowing what she was expected to do, and mechanically went through the motions of lifting off her camisole, sliding her g-string down, and even unfastening the skirt. She folded her garments neatly, placing them on the back windowsill, carefully, delaying the inevitable. Through it all, Todd just sat back, patiently watching Sherry strip for him. He had already removed his pants and shorts, and his shirt hung open. He stroked his cock slowly, keeping it ready to plunge into Sherry.

Sherry dropped down, reaching for his cock, licking her lips. She thought it ironic that she was looking forward to sucking his cock, a task she had deplored and refused to perform for even her husband just the day before, because she knew that sucking Todd off would at least delay something that seemed so much worse.

Todd wasn't going to play along. He waved her off. "No, no, you know that's not what I want. Turn around." Sherry knew she had no choice, so she slowly spun around until her bottom faced Todd. She pushed her hips into the air. Todd climbed to his knees, his fingers tracing the line of Sherry's butt crack until he came to the small, puckered ring of her asshole. As his finger probed her gently, he was surprised to feel Sherry's whole body tense, not relaxing until his finger trailed down, across the sensitive flesh below, to her pussy. Ever so slowly, e ran his finger forward, up her slit, until it reached her clit. Now he twirled it around the small fleshy mound, and reversed the progress, down her slit and back to her quivering asshole.

Todd was driving Sherry crazy. Each time his finger brushed her tight little anus, she felt her backside clench, the sphincter tighten, and her belly suck in. On the third such repetition, Todd wiggled his finger into her pussy, and then dragged his finger back to deposit the tiny amount of moisture in small circles around her clenching backside. She knew that if she was to help the process, she had to be wetter, so she reached down, stroking her clit and lips, slowly increasing her rhythm, until she felt her pussy growing wet. The sensations in her vagina distracted her momentarily, her ass relaxing, and Todd took the opportunity to stick his finger into her nether hole, depositing the slick juices he had been collecting into her tight little hole. Plunging his finger in, he worked it back and forth, in and out, feeling Sherry's sphincter alternately relax and tighten around the invading digit.

At length, he could wait no longer. He replaced his finger with his latex-covered dick, running it down the crack. It stopped briefly at her hole, but continued on, until he could slip it into her pussy.

As Todd pumped his cock into her vagina, Sherry briefly hoped he had changed his mind, judging her too tight or something. Her hopes were short lived, though, as he withdrew the cunt-juice slickened latex and quickly swung it up her butt crack. Lining up carefully, he applied pressure, the rock-hard head of his shaft prying wide her little hole, stretching her sphincter until with a sudden forward motion, he was in her.

Sherry screamed at the sudden violation. "No!" she cried, tears in her eyes. "No! No! Please don't!" Her pleas unheard, she felt Todd begin to pound into her, harder and harder, his ball sack slapping her pussy as he rammed her as deep as he could go. Sherry frantically worked her clit, trying to distract herself from the feeling in her behind. Strangely, the job seemed to be becoming easier, as she felt her backside relax and the sensation of fullness engulf her groin, the pressure building until she knew it needed release.

Without warning, she cried out, her lower body convulsing in a pulse-pounding, body-wracking orgasm. Electric spasms coursed through her body, across her belly, her pussy clenching and releasing in waves.

Her asshole, too, reacted. Todd felt her already tight butt clench hard on his rod in time with her spasms, grabbing and relaxing, holding him deep in her, squeezing him like a cock-ring, until he could hold back no longer. He pumped as hard as he could, listening to Sherry's soundless gasps as he twitched deep in her bowels in his own silent release.

Suddenly spent, they fell apart, Sherry pitching forward as Todd sunk back against the door. He watched as she just lay there, eyes pressed closed, gasping. He watched the gaping hole of her ass slowly closing, as her sphincter returned slowly to its customary state. He watched Sherry's hand drift back to her crack, a finger sliding down to her not-quite-closed hole, sliding in slightly, at then quickly backing out, to gently massage the abused ring of muscles that surrounded her puckered orifice.

Finally, Sherry sat up, dressed, and walked gingerly away. Todd sat in the car, watching her go. This had been a great pleasure. It had been a pleasant surprise to find a hooker, especially one of this woman's age, who had still clearly been an anal virgin. He had seen her reluctance to even try this, but he had watched as the lure of money won out over her qualms. It confirmed in his mind the power he had over this class of people. He had always known that with his money he could have anything he wanted. This just reinforced that notion to him.