The Babysitter

by Dawn (Oct 99)

It was a Saturday in late June and Holly was going to babysit the kids next door that night.
Usually she went out on Saturday nights, but on Wednesday she had agreed that she would do this for the Rupps while they went to a high school reunion in a town that was about forty miles away.
The Rupps had three children, Jack who was eighteen and just left two months earlier for the Army, Matt who was thirteen, and Heather, who was only nine.

When she got to the Rupp's, Mr. Rupp opened the door and smiled broadly.
Holly was growing into quite a young woman. She was seventeen and a raven haired beauty of a girl with a model's face and a shapely body.
He stood back and let her in and watched her as she entered the house. She was wearing a red tube top that was struggling to contain her firm breasts and a pair of tight shorts that showed off her round, firm ass.
As she walked past him, Mr. Rupp caught a scent of her subtle perfume and he started thinking that he wanted to stay home with her and send his wife off by herself.

Mrs. Rupp came out of the bedroom and smiled when she saw Holly.
"Oh good, you're here Holly. Heather and Matt are finishing their dinner. Matt is going over to Rick's house after dinner and I've told him to be home at nine. We should be back by two. I've left all the telephone numbers are by the phone, including Rick's parents if Matt isn't home by nine. If you get tired, you can sleep on our bed, okay?"

Holly smiled and said, "Sure. There won't be any problem, you have good kids, Mrs. Rupp."

The Rupps left and Holly waived goodbye.
Matt came walking out of the kitchen and saw her and smiled. "Hi, Holly," he said as he walked past her towards the door and caught the same scent his father had.
Matt had a crush on Holly and now he wanted to get out before he got a hard on and Holly noticed the bulge in his pants, because the sight of her was turning him on. Holly turned and watched him as he headed out.
"Hi, Matt! Bye, Matt. Be home at nine or I'll be calling Rick's parents!"

"I will," he replied, as he closed the door behind him.

Holly and Heather sat that evening and watched television and at nine, Heather announced that she was going to read awhile and then go to sleep.
Holly stayed on the couch and looked up at the clock and saw that it was nine fifteen and considered calling Rick's parents when Matt came through the door.
With mock seriousness, she said, "You're late, young man!"
Matt grimaced and said, "Sorry, I lost track of the time."
Holly smiled and said, "Well, I'll let it go this time, but don't let it happen again. Come and watch some TV with me."
Matt sat down on the couch and asked, "What are you watching?"
"A movie called 'The Graduate.' Have you seen it?"
Matt shook his head and uttered, "No."
As they watched the movie, Matt kept glancing over at Holly's breasts, thinking that she didn't notice, but she caught him doing it several times out of the corner of her eye.
When she got up to walk to the kitchen, she stopped to straighten a picture on the wall and caught him watching her ass as she walked.
In the kitchen, she smiled and thought, "Thirteen years old and he's a horny little bastard, isn't he?"
She stuck her head back out and saw that he had one of the decorative couch pillows on his lap and asked, "Want anything, Matt?"

He looked up red-faced and said, "No, I've got to go to bed. I've got to get up and do my paper route tomorrow morning."

Holly ducked back into the kitchen.
She grinned broadly. She was pleased with herself because she had given Matt a hard on and he was hiding it with the pillow.
The thought was turning her on and she felt her pussy moisten.
She got herself a Pepsi out of the refrigerator and went out to the front room and found that Matt was gone.
Sitting back down on the couch, Holly watched the movie for another fifteen minutes and then decide to check on Heather and Matt.
Heather's light was out and when Holly went into her room, she could see that Heather was dead asleep.
Closing the young girl's door, Holly walked down the hallway and saw that the light was still on under Matt's closed door.
She smiled, wondering whether she would catch him jacking off if she opened the door and looked in.
She opened the door and saw him bare chested under the covers reading a science magazine.
Embarrassed, he pulled the covers up a bit and said, "I thought I'd read for awhile."

Holly walked in and sat on the bed and stroked Matt's soft, brown hair.
Matt blushed beet-red, but said nothing as Holly smiled at him and he looked at the foot of the bed. He could feel himself getting hard again and hoped she didn't notice.
Out of the blue she asked, "Do you want me to teach you about sex? I saw you staring at me."

Matt didn't think he could get any redder, but he did and still nodded.
Holly smiled. "Good. You've been wanting to see these all night and I want to show them to you."
She took her hands and pulled her tube top over her head and let it drop on the floor.
Matt's eyes grew wide as he stared at her two luscious melons and he thought he might cum right then and there as his cock pushed up and out of the top of his boxer shorts.
Holly got up and removed her shorts and her panties as Matt gasped seeing her deep black bush. She lifted up the covers and crawled into bed with him and put her arm under his head.
She ran her other hand up and down his torso as Matt's breathing quickened.
Then her hand went down and brushed his cock head and Matt closed his eyes.
She reached in his shorts and stroked his stiff cock and he pushed his shorts off of himself so that they were both bare now.

How many times had he jacked off thinking of a moment like this with someone like Holly? And now it was here. Matt was wondering whether he had fallen asleep and this was all a dream.
It wasn't, he decided and he started to relax.
If she wanted to teach him about sex, he was more than willing to be her student.
"Does that feel good, Matt?" Holly asked, with a smile.

"Yes," he muttered as he lay with his eyes closed.
Holly stopped and took her hand off his cock and pulled his face towards hers, as she looked at him.
"The first lesson: it's not just about you, Matt. I can make you cum within a minute, but you have to make the girl cum too and girls take longer than guys.
You have to know how to kiss, foreplay is oh so important, and fucking is an art.
If you can learn how to make a girl cum, they'll be beating your door down to sleep with you. I'll teach you all of that if you're willing to listen."

"I want to learn, Holly, but I'm about to explode right now! I've never done this before."
Holly smiled and stroked his cheek.
"I know, sweetie. Let me take care of that and then I'll check on your sister and come back and show you."
Holly pushed the covers all the way to the foot of the bed and then straddled Matt's legs.
Pushing her hair back, she bent down and took Matt's cock gently in her right hand and stroked it.
His clear pre-cum appeared on the tip and she took her thumb and rubbed it around the head of his cock.
Holly lowered her head and opened her mouth and ran her tongue around the young boy's rigid cock.
Matt moaned as her agile tongue went round and round his swollen cock head and then she took his seven inches into her mouth.
She stroked up and down rapidly with her lips and tongue and Matt moaned even more loudly as he felt his balls force the cum up through his throbbing cock and into her wanting mouth.
Waves of pleasure ran over him as he stroked her hair and she swallowed his cum.

Holly swallowed and swallowed and then finally the flow of his warm seed subsided.
As she took her mouth off of his cock one final little spurt emerged from his hole and dribbled down his shaft and Holly licked it up with her tongue.
Matt was laying motionless with a satisfied smile on his face as Holly sat up and said, "I'll be back in a few minutes.
Don't fall asleep!"
Matt smiled. "Don't worry. I won't!"
When Holly left, he heard her go in the bathroom and then she was gone for a few minutes and Matt started wondering what had happened to her.
When she returned she was holding two glasses of a clear liquid in her hands.
She handed one to him and sipped from the other one. Matt smelled it and asked, "Vodka?"
Holly nodded and replied, "Yeah. Do you think your parents will miss it?"
Matt smiled. "I'll fix it. Go ahead and drink up."
Both Holly and Matt swallowed the liquor quickly and felt it explode in a blanket of heat that spread through their torsos.
Taking Holly's glass, Matt left as Holly laid back on the bed. When he returned, each glass had another shot of the clear liquor in it and they both swallowed their drinks again.
Matt took Holly's glass and put it on the floor with his own.
Rolling over, he took her in his arms and said, "Where were we?"
"Did you fix it?" Holly asked.
"Yeah. I put some water in the bottle and swished it around, they'll never know. Plus, they never drink vodka.
They keep most of that liquor for friends that come over."

Holly stroked Matt's cheek.
"You don't think they'll come home early tonight, do you?"
Matt smiled. "You've got at least a minute's warning if they do. They'll sit out in the car and wait for the garage door to open and then drive in and come in through the kitchen door. You'll hear the garage door start to open when they get here. It's always the same without fail."

Holly was feeling the effects of the alcohol now and was stroking Matt's hair.
Matt pulled her to him and slipped his leg between hers and felt the moisture and heat emanating from her pussy as he grew hard again.
He leaned and kissed her lips and as he did both of their mouths opened and their tongues met and swirled together in pleasure. Holly pulled him close to her and Matt felt her hard, erect nipples press against his chest.
As Matt stroked her side with his hand, his tongue went to her neck and he kissed her softly as he worked to each of her ears and traced the edges of her each with his moist lips.
Holly moaned, and Matt brought his hand to her breasts and stroked and squeezed each gently as Holly breathlessly asked, "Where did you learn all of this?"
Matt stopped and smiled. "I've read a lot on the internet. Articles by women on lovemaking. I was curious."

They kissed passionately again and Matt moved his lips to Holly's breasts and touched each one in turn and suckled them as his tongue teased each nipple and Holly's moans became louder.
Moving his leg from between hers, Matt reached down and softly stroked the insides of Holly's thighs as she gasped.
His hand moved to the source of her heat and he slid his fingers up and down her moist, swollen pussy lips as he kissed her firm stomach and then spread her legs to kiss and tongue her sensitive thighs.
Reaching around each leg with his arms, he laid down facing her juicy hole and used his thumbs to push back her pubic hairs and open her lips.
Matt's tongue went slowly up and down Holly's outer lips and then into her pussy, making her gasp with pleasure.
He unhooked one arm from around her leg and placed his middle finger on her opening and gently inserted it bringing on another gasp of joy from the young woman.
Her juices were flowing freely now and Matt's tongue found her clit as he slipped another finger in and stroked rhythmically in and out as Holly's head rolled pleasurably from side to side and she kneaded and squeezed her breasts with her hands.
Working deliberately, pleased with the pleasure he giving her, Matt brought his fingers to the top of her vagina and found the spot he was looking for.

He rubbed it over and over and sucked on her erect clitoris as her juices ran down his chin.
She gasped loudly and reached down to pull Matt's face into her as her pussy contracted wildly and she squeezed him with her thighs.
Matt was afraid her moans might awaken his sister, but he continued stroking and sucking her as her juices ran like a river and Holly thrashed about in intense pleasure. He felt her pussy tighten tightly around his fingers and a flood of her delicious juices flowed as his tongue ran back and forth over her pussy lips.
Holly laid back, as she quieted down and whispered, "Fuck me now."

Matt crawled up between her legs and Holly took his head and kissed him again. "Thank you, baby," she murmured.
"That was incredible. I want you to cum in me. I want to make you feel good."

Reaching down, Holly guided Matt's hard cock into her waiting, wanting, anxious hole.
She moaned again and Matt whispered, "Holly, this feels so good. I didn't know it would feel like this."

Holly smiled and kissed him.
"I know, baby. You feel so good in me too."
They went slowly, with Matt stroking his hard cock in and out of her pleasure hole as Holly thrust up to meet each stroke.
Holly began breathing rapidly again and moaning and Matt stroked faster feeling his own orgasm nearing.
As her pussy walls contracted tightly against his piston like motions and Holly grabbed him tightly, Matt erupted into her womb sending streams of seed into her until they were both spent and gasping for air.
Matt lay holding her and then rolled off her when he felt his cock soften and fall out of her.
He kissed her face and then he took her in his arms and kissed her again.
"Thank you," he said with a smile. "You were a good teacher."

Holly smiled back and put her fingers on Matt's cheek.
"I didn't teach you anything! You taught me. I'm never had a guy that made me cum like that. I want to do it again sometime."

Matt head the garage door start to open and they both sat up and Holly scrambled out of the bed.
Grabbing her clothes, she leaned down and Kissed Matt on the lips and quickly said, "We can talk tomorrow."
Holly ran out of Matt's bedroom and closed the door and went into the bathroom to dress.
She had left her purse in there and after she washed herself off, she put fresh perfume on so that Mr. and Mrs. Rupp wouldn't detect any scent of sex on her.
There was a knock on the bathroom door as Holly ran the water in the sink and flushed the toilet. "Holly? We're home."

Holly opened the door and smiled. "You're home early."
Mrs. Rupp nodded and replied, "Yes. We were a bit tired. The children weren't any problem, were they?"
Holly smiled. "No. They were both perfect."
"Matt wasn't any problem, was he?"
"No, Mrs. Rupp. He did everything I told him to do."
"Good. Here. This for you." Mrs. Rupp put some money in Holly's hand and said, "We really appreciate this."
Holly smiled and started to walk to the front door.
"Anytime. I'll be more than willing to watch Matt and Heather. So if you want to go out, just call me."

Matt was listening on the other side of his door and trying to contain his laughter. If only his mother knew how good of a boy he had been that night!

Holly knew and she was grinning as she walked next door as Matt's cum was running out of her and soaking her panties.
"I definitely wouldn't mind babysitting Matt again!" she thought as she went inside.

"Not at all!"