Sex Stories

FANTASY

The Babysitter

“Mom, I’m thirteen, I don’t need a babysitter,” Jacob whined, stomping his feet in frustration.

Mrs. Lindsey wagged her finger in her son’s face, looking to his two snickering friends in the background. “You are not the one with the babysitter,” she explained for what must have been the thousandth time. “However, you have two friends spending the night, and I doubt you three boys are going to be watching your three-year-old sister, and so Sheila is coming over to watch Kayci while you three do your thing. But don’t give Sheila trouble, or else I will have all three of your hides.”

That was when Sheila entered Jacob, Sam, and Nick’s lives. They watched her come in through the front door, allowed in by their father, and all of those hormones that had been dallying for months suddenly came in full force. Her soft sienna hair fell around her shoulders and down her back, two curls in the front curving around breasts that they had only seen in their father’s Playboys. Her hips were wide in a sensual way, and her legs were long, the short skirt only elongating them. She stepped in, reaching her hand up and pulling her long hair back into a ponytail as she did and looked to the boys and smiled.

“Kayci is in bed already,” Mrs. Lindsey explained, hurrying to catch up with her husband. “The boys are most likely going to be in the living room eating pizza and watching movies. Feel free to eat whatever you want, use the phone as long as it is local, or harass the boys.” Mrs. Lindsey hurried out the door, Mr. Lindsey giving the babysitter a wink as he left. Sheila waved to them happily, giving Mr. Lindsey her own wink back, and then closed the door. She looked to the thirteen-year-old boys with disdain.

“All right, you boys do what you want, I’m going to go up and check on Kayci,” Sheila explained, then turned quickly on her heel and went up the stairs, ignoring the stares of the three boys.

“I have never seen a girl so stacked,” Jacob said in wide-eyed wonder.

“What to you think she looks like with her top off?” Nick asked eagerly.

Sam raised an eyebrow and wiggled it happily. “I bet if we break into our secret stash of money that we could pay her to do it!”

“We were saving that for our trip to the Star Wars convention,” Jacob argued, looking to the floorboard that covered the hiding spot of their supply of money.

Nick shook his head, just remembering the sweet curves of Kayci’s babysitter. “I think this is much more important.”

Sam was nodding hurriedly in agreement. Jacob, resigned and kind of wanting to himself, hurried over to the floorboards and pulled it up, taking the stash of money out of the boards before he would get caught. The three boys then went up the stairs and towards Kayci’s room. The three-year-old girl was fast asleep in her bed, Sheila sitting in the rocking chair next to her bed. Sheila looked up at the boys who suddenly blocked the light of the hallway with their presence in the doorway.

Sheila walked to the door and pushed them out of the room, closing the door gently behind them. “What are you doing?” she hissed. “You might wake Kayci up.”

Jacob held up a twenty-dollar bill and waved it in front of Sheila’s face. “We have a proposition for you,” he told her. “But, if you aren’t interested…” he began to put the bill back into his pocket.

Sheila grasped his wrist and looked to the twenty hungrily. It was hard to make that kind of money babysitting, especially when the parents never expected to be gone very long. “What do you want from me?” her voice was still hushed, worried for the baby she was leaving in the room behind the door.

“Come to my room,” Jacob insisted, pulling his wrist away from her grip with a hungry smile and walking away. The three boys and Sheila went into the Star Wars infiltrated bedroom and Sam closed the door behind them. Sheila looked to them curiously.

“I have to be able to hear if Kayci wakes up,” Sheila snarled.

“This won’t take long,” Sam insisted.

“We will give you $20 to take your top off and show us your boobs,” Jacob blurted out, very anxious to see Sheila’s reaction.

Sheila did not even balk. “Give me the twenty first,” she said, holding out her hand for the money. The three boys, standing in front of her looking on anxiously exchanged glances, but it was decided they were desperate enough. They nodded in unison and Sheila smiled, the twenty landing softly in her hand. She shoved the twenty into a pocket in her skirt then grabbed the hem of her shirt. “I hope you boys are ready for this,” she told them. She pulled the shirt up, over her head, and completely off. She stood in front of them, breasts spilled only into a soft white bra that was so low it gave the boys a glimpse of the soft pink nipple of the breast. The boys itched to touch those perfect soft mounds.

“Take the bra off too,” Sam insisted, reaching out to touch her. Sheila smacked his hand away easily.

“All you asked for was my top, the bra stays on,” Sheila began to ready her shirt to pull it back on her head.

The boys huddled together and discussed this new situation. It was decided they needed more, not just wanted more. Nick held up two more twenties and held them out to Sheila desperately. “If you take off the bra and let us touch your breasts, then we’ll give you forty dollars.”

Sheila hesitated, the shirt hanging above her head, ready to come back down. She bit her lip and then dropped her shirt to the floor. The boys waited anxiously, but Sheila shook her head gently. “Fifty,” she negotiated.

Nick and Sam pulled the money out of Jacob’s hand and shoved the bills at her. She crumpled them up and slid them into the pocket of her skirt. She reached behind her and easily unclasped the back of her bra and let it fall completely away from her body, falling to the floor next to her shirt.

For a moment the boys did not even move. They had paid to touch these soft breasts, but now they were unsure. They were just so there, and so tempting, they were awestruck.

Jacob was the first to move forward and with a rough hand, he grasped her left breasts and squeezed. She let out a little squeal of pain at the roughness of his grasp, and he eased a little. He was just fascinated by the feel of it beneath his palm, the softness rubbing against it, the nipple hardening at his touch. He rubbed it with his hand, moving it in a circle, feeling it around and pushing her towards the closed door as he did.

Sam and Nick did not hesitate any longer. They stepped forward and suddenly three pairs of adolescent hands were on her breasts, toying with the nipple and squeezing it in unpolished form. They ran their hands over her, feeling those curves, enjoying the need that was growing in them, and the way her mouth opened just enough to breath out sighs of need and desire. This only had the boys want more as they squeezed and pulled. Parts of them were wanting her like they had never wanted anything, even more than they wanted to go to the Star Wars convention.

Sam tweaked one nipple, Jacob worked on the other, and Nick tickled his fingers against the bottom of the curves of those breasts. They were causing her an enjoyment that they did not understand, and they wanted the enjoyment to carry over to them.

“Let us do more to you,” Jacob said suddenly. “We’ll give you more money.”

Sheila suddenly started pushing hands away from her, worried about their sudden need. “No way,” she said. “How much more do you think you three can do to me with your little dicks?”

“Let us see you completely naked,” Nick was begging. “We’ll give you more money.”

Sheila bent down to reach for her bra. “You guys are ridiculous, you’re thirteen.”

“Another three hundred dollars to let us do what we want with you,” Jacob blurted out, holding up most of the rest of the Star Wars money.

Sheila hesitated, letting the bra stay on the floor. The money would be a good way to put a down payment on that hot little car she wanted for herself. Besides, what danger could she face with having a bunch of thirteen-year-olds having their way with her? After all, it was no worse than the person she was fucking on a regular basis, and she was on the pill.

“Four hundred,” Sheila insisted. She held out her hand, her breasts bouncing in front of her. The boys were mesmerized with beauty, and sexual desire for the seventeen-year-old babysitter.

For the last time the three boys huddled together and began to count out their money. They had three-hundred eighty-nine dollars. “How about three eight-five?” Jacob asked, holding out the remainder of the money, not insulting her enough to mention the last four dollars.

“Done,” Sheila said before they could even blink. She swiped the money right out of his hand and once more began to put it in her pocket. This time, however, she barely had it in her pocket before the boys crowded her and began pushing her towards the bed. She found herself lying on her back, three boys crawling up on the bed next to her, hands roving her body. One pair of hands went between her legs and straight to her panties, feeling the pink silk and rubbing against it, worrying the wetness that had begun to form there. Sam was leaning forward and sucking on her nipple of her right breast, Jacob was trying his hardest to pull her skirt down over her luscious hips. It took the boys a few minutes to get Sheila’s clothes off, but soon she was naked. It was the closest the three had ever been to a naked woman, and they were not going to waste the experience.

Nick stuck his fingers into her pussy without hesitating. It was almost like he knew what to do, though he was rougher than someone who had been with a woman before. Three fingers slipped in and his hard on became complete. He pushed his fingers deeply into her, rougher and hurting her small pussy, though she had more than this inside of her before.

Jacob decided to do the same thing while Sam continued to have fun sucking on Sheila’s bruising nipples. Jacob put his fingers in, with Nick’s, and moved them around, wondering why men got pleasure out of this dampness of a woman’s body. He still did not understand the pleasure just that it was working. His small little cock was growing hard, and he was pushing into her harder and harder. She made small little mewling sounds, fighting and tensing her body, trying to push so many fingers out of her.

Sam was the one to look in her eyes and ask, “Can we fuck you?”

“You paid for it,” she said breathlessly. She hated herself for being turned on by a bunch of adolescent boys, but she was enjoying their fingers roving her. They were so unskilled that it felt better, they were learning while on top of her, and the roughness was turning her on.

Jacob was the first one inside of her. She did not even remember him pulling down his shorts, but suddenly his cock was trying to find its way inside of her, the head slipping several times and poking her many times in the wrong places. Then, it was in her, pumping her, and like all men, he knew instinct when it was within him. His hips began moving back and forth, pushing into her, deeper and deeper, and though he was not hitting the most perfect of spots, her walls were wet enough to just enjoy the feeling. She tightened her pelvis and let him continue to push into her. He was desperate, wanting more and more, while Sam and Nick watched in a morbid fascination as their friend took advantage of her.

Jacob did not last very long. He came into Sheila’s warm pussy before it had even lasted five minutes, and she was a bit disappointed, but then Sam was inside of her, pumping healthily.

Sam was a bit better than Jacob had been, pushing into her, shoving against her walls, but he was definitely smaller. She guessed she could not expect much from a thirteen-year-old. He went deep, and lasted about the same length of time, mixing his cum with Jacob’s, then pulling out of her, kind of enjoying the feeling.

Nick was the best, pushing inside of her, the largest of the three, and driving the deepest. He gripped her hips, readied himself perfectly, then began pumping into her. He enjoyed the feeling of the head pushing deep into her, the friction of two bodies during a primal fuck, and he wanted it more than he knew. She moved her hips with his, heightening his enjoyment, while the other two boys tried to clean themselves up, and watch all at the same time.

Sheila let Nick have his way with her, his fingers bruising her sides as he continued to move in and out. She pushed her hands above her head and arched towards him, giving them their first real experience in messing around with a woman. For the three geeks it would probably mean that they would not have sex again until their late teens, early twenties, so she allowed them to take advantage of her damp pussy as much as they liked.

Nick came into her, but he was unwilling to stop. Even when limp he was still moving inside of her, trying to get it back up again.

“Give it up,” Sheila laughed, sitting up and moving Nick away from her. “You boys got what you paid for.”

She reached for her clothes, finding them at all ends of the room. She began placing them back on while the boys watched, none of them knowing what to say.

“Can we do that again?” Jacob asked desperately. “Another night, not tonight, but, please,” he begged.

Sheila shook her head and opened the door of the bedroom. “Sorry boys,” she told them. “That was the last of your cash, and I think my boyfriend might be a little jealous if he finds me diddling with a bunch of kids.” She threw her head back and laughed, walking out of the room and leaving the boys to discuss what they had just invested in.

A hooker would have been cheaper, but Sheila was definitely better. Jacob’s dad knew that very well.