Bribing the Babysitter

Chapter 1

It had been two months since Jenni had first let Mr. Taylor masturbate on her. It was becoming a bad habit.

Mr. Taylor didn't make a mess on her thighs every week. Jenni typically babysat for the Taylors on Tuesdays and Thursdays when no one would be home until late, and on the occasions that Mrs. Taylor drove her, the nights went by uneventfully (and if Carol suspected anything, she kept it to herself).

Most nights went by uneventfully. It was only sometimes that Mr. Taylor would stop at the dirt road that led away from the entrance to her neighborhood, and when he stopped he would give her a look. Jenni knew what the look meant.

Her street was a typical North Carolina affair, with her neighborhood bordered by a small wood, backroads criss-crossed by nature trails and biking paths. Just before the track of modest suburban houses there was an offroad trail that led to a picnic area. That was where Mr. Taylor would drive her if he wanted to cum on her, away from where anyone might see - in the dark woods, lit only by the lights of the car and the stars.

The first time it happened, it was a late June evening. The moon was out, but the sky was still half-lit by the red and yellow horizon. Mr. Taylor had come home early from his job in downtown Raleigh.

The man worked for one of the major pharmaceutical companies in the Triangle, and he was usually tired long before he walked through the front door. If he was too tired, he'd ask Mrs. Taylor to drive Jenni home. Mrs. Taylor also worked long hours, and if Jenni was still at the house by the time both of them arrived, neither was in a mood to make dinner for the kid. But Jenni didn't mind doing that, and Teddy said he liked her macaroni and cheese better than his grandma's.

Jenni lived further out than the Taylors cared to drive, she knew, but their house was right next to her community college. When her classes were done, she walked to the Taylors' house to look after Teddy, and freed up the grandmother to do whatever it was grandmothers did. Now that it was summer, Jenni had more time to watch Teddy, and she and the boy would spend their days at the park or singing along with his favorite videos. It wasn't the kind of job that had a future in it, but the kid was cute and the Taylors paid better than any family she knew.

That June evening, Mr. Taylor got home earlier than usual. It was just after she had put Teddy to bed, and she smiled at him when he said hello and continued to do the dishes from the night's supper.

Dennis Taylor was older than his wife. He was in his mid- to late forties, with dark brown hair that had a few gray hairs at the temples. He was tall, not unpleasant to look at, but not really interesting to look at either. Jenni, on the other hand...

The nineteen-year-old was not oblivious to the effect she had on men. They didn't need to be Mr. Taylor's age to notice her; in fact, she had yet to find an upper or lower limit to male attention. She tried to take this in stride (and not a little self-satisfaction). On this particular night she was wearing a faded pink skirt that she intended to get rid of soon. She'd kept it so long because it hugged her hips comfortably and it ended at about her mid-thigh. It was something she probably would not have worn when she first started babysitting for the Taylors, but she was more comfortable now and she didn't think they'd mind. It showed off her long legs and matched her pink toenails. She wore a black halter top that fit snugly on her chest, with a white summer shirt over that. When Mr. Taylor came home, the shirt hung limply on the back of one of the kitchen chairs.

Jenni's breasts were were high and firm, and their full, round swells gave her a generous cleavage in the tight top. The summer heat made her chest shine with perspiration, and her thick brunette hair never behaved well in the North Carolina humidity. Everything felt wet and sticky.

She finished up with the dishes and flicked her hands free of the soap and water. She dried them with the dishtowel and glanced at Mr. Taylor as he stepped into the kitchen. "How was your day?" she asked.

Mr. Taylor usually answered with a weary grunt. Today he looked at her, and he looked her up and down. Jenni had begun babysitting for the Taylors when she was eighteen, and sometimes she did catch Mr. Taylor looking at her in a way that she would have been stupid not to understand. But that was all they were, looks, and Jenni was used to looks. Tonight the look was the same, though this time he did it without pretending to be looking at something else. "That's a nice outfit," he said.

"Thanks," she said. She hung the dish towel on the refrigerator door and leaned back on the counter. "You're early."

"Yes," he said. He frowned as he looked at her and she gazed down at herself to make sure she didn't look strange. She'd wet the black tank top, she saw, and her nipples were poking through the material. She hadn't worn a bra today.

It was late, the shirt was black, so she could pretend not to notice - but Mr. Taylor had definitely noticed. She didn't really care. When she looked up, he pretended to fixate on something over her shoulder.

"Grandma's on her way," he said. "As soon as she's here I can drive you home."

"Thanks," she said.

That was typically the extent of their exchanges. Mrs. Taylor was a little more talkative; she talked about her job, about Jenni's classes. Mr. Taylor did not. He went to his office and left her in the kitchen and she pulled her purse off the kitchen table and folded her summer shirt over her arms. Then she remembered that her nipples were still poking through her shirt and decided to put it on.

Grandmother Ann arrived less than ten minutes later and they all said their quick greetings - and quicker goodbyes - and soon Jenni and Mr. Taylor were driving across town to her neighborhood. They made very small talk on the way, but by the time they reached the entrance to her neighborhood they were silently listening to the radio.

When they reached the place where the dirt road branched off from the main one, Mr. Taylor eased the van onto the shoulder and switched off the radio. He put the van in park.

Jenni frowned and gazed out the windshield at her neighborhood beyond. "Why are we stopping?"

Mr. Taylor sighed. He stared straight ahead for a moment, then reached up and took an open envelope off the dashboard and laid it softly in her lap. The Taylors usually gave her her wages this way (though they typically handed it to her) but she immediately felt the difference in the envelope. Curious, she picked it up and leafed through it. If she watched Teddy for a whole day, she usually made about $100. The envelope contained at least $300.

Jenni slowly looked up from the envelope. She met Mr. Taylor's tired brown eyes. "What do you want?" she asked.

"This is between us," he said, "this conversation."

She wasn't stupid. "Tell me what you want," she repeated. Her heart started to race, and she calculated how much time it would take her to unbuckle her seatbelt, pop the door and run - if necessary.

Mr. Taylor looked down at her thighs, at the envelope between her pink fingernails, and then back at her. "You can keep the money," he said, "even if you say no."

"I don't know what you want me to do," she said. Then she added, "I'm sure Carol won't like it."

He sighed again. She found it irritating, but she wasn't married to him. "No," he said, "but I'm not going to ask you for sex."

"Oh?"

He said it very matter-of-factly: "I want to ejaculate on you. I want to cum on your body."

Jenni's heart continued to pound against her chest, but the plain-spoken way he'd said it didn't make him sound like a psycho. Maybe that made it more psycho.

"Here?" she asked.

"No." He pointed down the dirt road. "Somewhere down there," he said. She could see that admitting this to her was not easy for him. She could also see that what he told her next was the honest truth and that it pained him. "I want you...to show me your panties. And I'd like to cum on them."

"Why?"

He seemed surprised at how well she was taking this. "Why?" did not seem to be the reply he was waiting for. He took a moment to answer.

"It's not cheating, technically, is it?"

He looked at her, and she looked at him. Her gaze told him many things, the least of which was how poor an excuse that was.

He paused. "I've been fantasizing about it for a while now. I want you to watch me masturbate. I want to ejaculate on you."

"That's it?"

"Yes," he said.

Jenni looked down at the money in the envelope. She was aware that boys in her class might be masturbating to her, and maybe her professors too, but her boss's request was unique. If only for its honesty. "How do I know you won't just rape me in the woods and leave me there?" she asked.

"We both have families that are expecting us home soon," he said. He thought for a moment. "There's a gun in the glovebox. If it will make you feel safer, you can hold it while I do it."

This was North Carolina. Guns in gloveboxes were not uncommon. Jenni even knew how to use one (the 9mm in Mr. Taylor's glovebox was not rocket science), but this sudden admission from him was as unexpected as his initial request.

"Do you want me to?" she asked. "Does that get you off?" She glanced down at his pants. She saw that he did already have an erection. It tented his pleated slacks.

"You can do what you like," he said. "But I would like to cum on you."

"Now," she said.

"Yes, now."

"How long have you been waiting to ask me this?"

"Will you let me?"

"If I say no?"

He shrugged. "I will continue to jerk off to you in the shower."

"And fuck your wife."

"We don't really," he said.

"It wouldn't be hard for you to find someone to fuck you," she said. "Someone who's not your babysitter."

"I'm aware."

Jenni stuffed the envelope in her purse. "But you want to jerk off on me," she said. "You want to pull out your pecker and cum on me."

He grunted and she saw that his erection was almost touching the steering wheel. "I think we understand each other," he said.

They drove up the dirt road until they came to the picnic area. There was no one around but he drove a little further in, where the trees pressed in close and the light from the fading day was just creeping in between the leaves. Mr. Taylor was driving the family van and the back seat was usually folded down, so the rear was one wide, flat area. She left her purse in the front seat and forgot about the gun.

Her heart was racing as she stepped out into the fragrant wood and went around the car.

Mr. Taylor, his erection more obvious now that he was standing, lifted open the back of the car and showed her where he wanted her to lie. She stood staring at bare back seat. "Can you take off your shirt?" he asked. "Just the white one."

She pulled her arms out of her sleeves and laid the blouse in the back of the car. Her chest covered only in the black halter now, she sat down on the bumper. She was still sweating, and her nipples were harder than before. The excitement, the feel of the fabric against them, it was unavoidable.

"Pull up your skirt," said Mr. Taylor.

"Let me see your cock first."

He stared at her with the same pained look on his face. He seemed surprised, but tense, needful. "Very well," he said.

He stepped back and unbuckled his belt. He unzipped his pants and slid them down his knees. He struggled with his boxers, trying to pull them down off his erection, and she saw it. It was red, very red - redder than her boyfriend's. Thicker, maybe; older, definitely. There was no question that Mr. Taylor wanted this. His cock was as stiff and angry-looking as if he were a twenty-four-year-old man.

Though Bobby, Jenni's twenty-four-year-old boyfriend, did not look at her with such professional-looking desperation in his eyes. Bobby's desperation was a little more obvious.

Mr. Taylor looked ridiculous in the woods with his dress shirt hanging below his waist and his red cock poking through the tails. The interior lights from the van were swiftly becoming their only light source, and he was spotlit by them. They backlit her big brown hair. "Let me see your panties," he said.

Jenni stood up. She spread her legs in the dirt. She took the hem of her skirt in her fingers and slid it up. The skirt was tight, so it took more effort for her to pull it to her waist. But when she was done she was more or less naked from the waist down, except for her thin white panties and her sneakers. She felt the evening air hit her ass cheeks. "You like that?" she asked. She thought of him jerking off to her in the shower and was thrilled by the soft tingle that went through her.

"Can you turn around, please?"

Jenni slowly rotated in front of the car. She kept her hands at her waist, holding up her skirt. She heard Mr. Taylor step forward and then felt a swift, sharp smack on her right buttock. He'd spanked her ass. She stumbled forward and glared at him over her shoulder. "What was that?" she said.

"I'm sorry," he said. "I should have told you."

"You didn't say you were going to spank me."

"It's very nice," he said.

Jenni quickly turned around. "That's a rule," she said. "If you want to touch me, you have to ask. And I didn't say you could spank me. Don't do it again."

"I'm sorry," he said formally.

The top of Jenni's head only came up to Mr. Taylor's nose. Her legs were the longest thing about her, but though she was petite compared to him, looking up at him now she realized she had more power here than ever before in their professional relationship (even with her skirt up at her waist). She'd ordered him to ask before he touched, and the tone of his apology made it clear that was a rule he would follow. "Do you want to do it now?" she asked.

"Yes," he said.

"Say please."

"Yes, please." She saw it in his eyes, she saw it in his posture. He wanted to cum. He wanted to jerk off. But his perversion wasn't complete without her say-so. She let a cruel smile cross her lips.

"What do you want me to do?" she asked.

"Sit back," he said. "Please."

Jenni sat down and eased herself into the van until her knees rested on the bumper. Mr. Taylor approached her, holding his cock in his hand. He shivered in anticipation. He leaned in. He set his hand on the carpet beside her and began to stroke himself.

Immediately a kind of relief transformed his face. His eyes glanced back and forth from her panties to her eyes. And she watched him (her hands tucked behind her made her breasts push out her thin halter top). The watching was what he wanted.

He wanted her to see him in his desperation, wanted her to know that this was his primal, animal urge, to masturbate himself, like an animal, in front of her. On her, for her. He was a married man, a professional, and he was no longer capable of keeping it in his pants around his young subordinate. His red cock glistened with the first of his precum and the natural lubrication of his body. He eased his hips forward so that the head of his cock touched the frail cotton of her panties, and each time it touched her Jenni got a little thrill from it.

Of course she did; her clitoris was right underneath him, slightly engorged. She got wet watching him, though truthfully she'd been wet since he'd slid the envelope in her lap. Her parents weren't home tonight and she'd been thinking of calling Bobby to come fuck her from the moment she stepped into Mr. Taylor's car. She wondered if Mr. Taylor knew she fucked her 24-year-old boyfriend in this same spot, in the backseat of his cluttered car.

Mr. Taylor grunted each time he pushed his cockhead against her panties. "May I touch your stomach?" he asked.

Jenni pulled her halter top over her stomach (it was a belly shirt, so it didn't have far to go anyway). Mr. Taylor put his hand to her skin and groaned. He squeezed her, letting her soft flesh titillate him further.

"Lay back," he said. He swallowed hard. "Please."

Jenni slowly lowered herself to the van's carpet. Above her, Mr. Taylor continued to masturbate between her bare legs. His fingers slid over her ribs and he pawed at her as if he'd never felt another human being in his life. Her flesh, warm and yielding, aroused him further. Mr. Taylor shut his eyes and thrust his hips forward, dragging the underside of his cockhead over her panties (which were quickly wetting with her own secretions and the drops of his peremptory semen).

"May I touch your thighs?" he asked.

"Say please."

"Please, Jenni."

Jenni folded her hands behind her head and propped her neck up to watch him. Mr. Taylor let go of her stomach and slid his fingertips down her naked thighs. They were pale and smooth, probably nothing like his wife's. The hot North Carolina night made them slick to the touch.

While he stroked her legs, Mr. Taylor continued to rub the underside of his shaft against her panties. His cockhead knocked against the hem of her skirt. It would be sticky with his cum by the time she walked into the door of her house.

Mr. Taylor gripped her legs hard and thrust his cock against her panties. The smooth underside of his shaft sawed against her crotch. Under her panties, matted in her sweaty pubic hairs, her vagina reacted to the friction. She gave a little grunt of satisfaction. She felt his balls whack against her buttocks.

She was his babysitter. He wanted to rub one out on her.

Jenni smiled to herself. She was getting off and Mr. Taylor was a pervert. Not her, though. She was just letting it happen.

"Your," he grunted, "your tits. Please."

"That's extra," she said.

His brow furrowed. "You can have it."

"A hundred dollars extra," she said.

"Yes," he said.

"Do you have it?"

He shoved his shaft into the wet line of her vagina. "Yes," he grunted.

She leaned up and played with the hem of her halter top. Her fingers rolled it up her sternum but didn't go further than the undersides of her heavy breasts. "Show it to me," she said.

"Please, Jenni." His thrusts were harder but his face was anything but pleasured. He look wounded, dying. "Please."

She smiled wickedly. "Show it to me."

With a tortured gasp he pulled away from her and reached down to his slacks, crumpled in the dirt. He pulled his wallet out of his pocket and quickly thumbed out five twenty dollar bills. He let them drop beside her shoulder and grabbed his cock again. He stroked himself furiously. "There," he said.

"What do you want?"

He almost snapped. "Your fucking tits!"

She rolled her halter top over her breasts. She was now mostly naked in front of Teddy's father, her shirt bunched up to her neck and her skirt hiked up to her waist. Her sneakers banged on the bumper when he shoved himself forward and pushed his cockhead into her panties, jerking himself, pumping. He groaned with appreciation. "May I touch them?" he asked. "Please?"

She nodded to him and he reached for her right tit. He clutched it too hard, groped her. She gasped aloud. He squeezed the soft swell of skin and let her hard nipple trace the lines in his palm. He let go of his cock and reached for her other tit, rolling his hips forward to rub against her wet panties as he fondled her. It was rough, and chafing, but it was a nasty, rough kind of dry sex, and it gave her goosebumps up and down her ass.

Mr. Taylor's eyes squeezed shut as he groped her, and she wondered how many times he'd jerked off in the shower thinking of her soft, young body in his hands. She rolled her hips against his jerking cock and let out a soft cry of her own.

"May I suck them?" he asked.

"Don't get carried away," she said.

"Please, Jenni."

"Once," she said, "for each."

He leaned down and licked her small nipple into his mouth. He sucked on it as if it would give him sweet milk, and when he pulled his lips away a string of saliva followed his mouth to her other, which he sucked, just as hungrily. Jenni came the moment his lips encircled that nipple, and she tried to hold back her gasp of pleasure as his hairy balls chafed her inner thighs. The orgasm wasn't earth-shattering, it wasn't amazing. But she did cum, just a little bit.