Little Orphan Annie

#Mature #Teen

2.9k words | 0 | 5.0078

Chester Molester

Jeff runs across a beautiful young girl who is in need of help.

Jeff was driving down the road from a business trip back to his house. He was still about a hundred miles away and it was starting to get dark. He was on a two lane road in the middle of nowhere. No houses or stores for the last 40 miles. He was pushing 50 years old now.

Up in the distance he saw a small silhouette on the side of the road. It continued to remain small the closer he got. He slowed down a little as he realized that it appeared to be a young girl walking on the side of the road.

She was wearing a pair of shorts and a t-shirt with what appeared to be flip flops on her feet. He slowed down and pulled over to the side of the road. She slowly walked up to the driver side and he rolled down his window.

“Hi mister. Can you please give me a ride? I’ve been walking all day and haven’t seen any one in a while.” She said as she looked at him with pleading eyes.

She looked to be around 15 or so. He could see that she was a little dirty and her hair was pretty dirty as well. He could clearly see that she wasn’t wearing a bra as the shirt was thin and he could see her plump tits capped with large puffy nipples.

“Sweetheart where are you headed?” He asked as he tried not to stare at her tits.

“I don’t know really. I ran away from the orphanage because I hate it there!” She said as she looked down at her feet.

“Orphanage? Where’s your parents at?” He said.

“They both were killed by a drunk driver a couple of years ago and I didn’t have any other relatives that wanted me!” She said as tears streamed down her dirty face.

Jeff felt sorry for her as he had lost his parents as a child too. But he had family that took him in.

“Get in. I think that I can help you out at least until we can figure out something else!” He said as she looked up at him with a smile on her face.

She immediately ran around the car and opened the door and climbed up onto the passenger seat. As she was climbing in, he got a glimpse of her plump little pussy as the shorts were too big around her legs. She wasn’t wearing any panties under the shorts.

“Do you have any other clothes missy?” He asked as he pulled back onto the road.

“No sir. This is all I have. The orphanage took everything from me.” She said as she fumbled with her hands.

“Well that’s just terrible. Let’s see what we can do before we head to my house. Unless you have somewhere else to stay for the night?” He asked as he looked down at her.

“No sir I don’t have anywhere to go. I don’t know anyone around here. In fact I don’t know anyone period except for the people at the orphanage and they didn’t care about us.” She said as a matter of factly.

“You have a problem with staying at my house for the night until we can get you some help?” He asked.

“You mean that I can sleep at your house tonight? In a real bed?” She asked as she looked up at him with uncertainty in her eyes.

“Of course a real bed! What have you been sleeping on?” He said.

“The floor mainly. None of us had beds. Some of us didn’t even have blankets!” She replied.

“Well little lady you are not going to sleep on the floor tonight!” He said as he drove down the road.

They had been driving for a while and he kept hearing what sounded like her stomach growling.

“Say I am about hungry. How about you?” He asked as he looked over at her.

She nodded her head yes enthusiastically. He chuckled and said “I thought so!”

“You know, I don’t even know your name! I can’t go around calling you missy all the time now can I?” He said as he smiled at her.

“I’m Vicky and I’m 15 years old I think!” She replied.

“You think you are 15?” He asked surprised.

“Well that’s what I was told by the people at the orphanage so.” She said.

“I see. Well it’s nice to meet you Vicky. My name is Jeff.” He said as he reached out his hand.

She shook it and smiled.

“It’s nice to meet you Jeff. Thanks again for stopping.” She replied.

“Well I couldn’t just leave you out in the middle of nowhere now could I?” He chuckled.

“I guess not!” She giggled.

He pulled into the drive thru of a fast food stop and ordered a couple of burgers and fries with drinks. They ate in silence as she devoured the food like she hadn’t eaten in a while.

Suddenly he felt her head on his leg. She had laid down on the seat and propped her head on him. She sighed heavily and was soon fast asleep.

He pulled into his driveway and entered the garage. He eased her head from his leg trying not to wake her but she opened her eyes and sat up.

“Hey there sleepy head! Get a nice nap?” He asked.

She yawned and smiled at him.

“Sorry, I was tired!” She replied.

“No worries, how about we go inside and you can take a shower before climbing into bed and get some rest?” He asked.

“Ummmmmm I don’t have anything to wear to bed!” She said as she looked at him.

“Well I think I have an old shirt that you can wear for tonight. I’m sure that we can find something better tomorrow when the stores open!” He said as he opened the door.

She looked around with wide eyes as she entered his house. It was big compared to the other places she had stayed. It had a TV and everything else. He showed her the bathroom and handed her a shirt.

“You can toss your dirty clothes outside the door and I wash them for tomorrow.” He said as he closed the bathroom door.

A little later he heard the door open and close. He went to the door and picked up the clothes. Thin shorts and shirt, nothing else. They didn’t look like they would even survive the washer.

He heard the shower turn on and then he heard her humming as she bathed. He went to the spare bedroom and got her bed ready for her. A little bit later she came out of the bathroom with a towel on her head and the shirt on.

She shook her hair out and grabbed a brush from the nightstand. He watched as she brushed her hair. Her tits were swaying back and forth under the shirt. She smiled as she looked up at him watching her.

“You clean up quite nicely Vicky!” He chuckled.

“It’s been a while since I got to take a shower! It felt amazing! Thank you for everything!” She said as she yawned.

“Don’t mention it! You get some sleep and I will see you in the morning!” He said as he walked out of the room and shut the door.

He took a shower and then climbed into bed. Some time during the night, he felt the bed moving and he looked over and Vicky had climbed into bed with him. She turned over and quickly went back to sleep. He turned over and went back to sleep as well.

The next morning Jeff woke up early and saw that Vicky was still asleep in his bed. She was out from under the blanket and the shirt had ridden up revealing her bald little pussy. It looked so delicious and inviting but he knew that she was too young.

He went to the kitchen to fix coffee and started breakfast. Just as he was finishing up, Vicky walked into the kitchen rubbing her eyes.

“Good morning!” She said as she walked over and hugged Jeff.

He could feel her hard nipples poking into his stomach as she wrapped her arms around his back. Her body was warm and soft.

“Well good morning to you too!” He said as he tried not to think about her being naked under the shirt.

“I slept so good last night! It’s been a long time since I’ve slept like that!” She said as she let go of him and walked to the table and sat down.

“I was surprised that you came to my bed last night. Something happen?” He asked as he sat a plate of food in front of her.

“I woke up from a bad dream and I guess I got scared. I hope you are not mad!” She said as she started eating.

“Oh honey I’m not mad. Just a little surprised that’s all. I mean I am a stranger and I’m old so…!” He chuckled as he sat down and began eating.

“You are not a stranger to me. I know your name and you have been more like my family than anyone else!” She replied as she licked her lips.

“And you are not that old. Not as old as the man at……” She started to say but she suddenly stopped and didn’t look at him.

He didn’t try to pry as apparently it wasn’t a subject that she wanted to discuss.

They sat in silence as they finished their food. Jeff was cleaning up the kitchen after handing Vicky the clothes that he had washed. She got dressed and they went shopping for her something to wear. He bought her panties, bras, shorts, dresses and tops along with shoes.

The more he bought, the brighter her smile became. She couldn’t believe all the nice things that he bought her. As they were heading back to his house she slid over to him and placed her hand on his thigh.

“Jeff can I ask you something? It’s kinda weird but I have to know?” She said as she looked up at him.

“Sure Vicky, you can ask me anything you want. I’ll answer you as honest as I can!” He assured her.

“Well why are you doing this? Why are you being so nice to me?” She asked.

Jeff looked down at her and she had tears in her eyes.

“Well Vicky it’s like this, I lost my parents when I was young. I know how that feels but I also had family that took me in. Unfortunately you didn’t so I just wanted to make sure that you have what you need at least for a bit anyway!” He said as he smiled at her.

Vicky laid her head against his chest and kept her hand on his thigh. She was rubbing her fingers against his thigh and he could feel her hand slowly drifting towards his crotch area.

He could feel his cock swelling as they pulled into his driveway and garage. They got out and carried all the bags into the house and took them to the bedroom where she was staying.

He left her in the room as she was going through the clothes and checking them out. He sat down in front of the TV with a beer and started watching. His mind raced around the images of her pussy, her tits and her hand on his thigh. He was so engrossed with his thoughts that he didn’t realize she had entered the living room and was standing next to his chair.

“Jeff are you OK?” He heard her say and it startled him.

He turned towards her and was about to say something but he stopped dead still with his mouth open.

Standing there was Vicky in a fancy bra that only covered the bottom of her tits and a pair of panties that were almost transparent. She was absolutely stunning and very sexy. He could only stare at her as she smiled a wicked smile.

“I….where….how??” He stammered.

He definitely didn’t recall seeing these things when they were at the store.

“I talked to the nice sales lady about them when you went to the restroom!” She giggled.

“Do you like it?” She purred as she slowly turned around.

Her sweet little ass was completely exposed and she didn’t waste any time bending over in front of him so that he could get a better view of her from behind. He saw her plump pussy peeking out from around the thin strip of material that was barely covering anything.

This was not necessarily something that a 15 year old would be wearing but she had the body for it. His cock was hard and throbbing by now.

She stood up and walked over to the front of him. She smiled as she looked down at the large tent in his pants.

“I think that is a yes!” She giggled as she reached down and grabbed his cock with her hand.

Jeff groaned deeply as he felt her hand squeezing him.

“Ummmmm Vicky I don’t think that you should be doing that!” He groaned as he grabbed her hand and pulled it off his cock.

“What’s wrong? Don’t you like me? Don’t you like what I am wearing?” She asked as she had a hurt look on her face.

“Oh sweetheart I absolutely love you and what you are wearing but I’m too old for you and you are too young for me to be seeing you like this! I could get into a whole lot of trouble if someone found out!” He groaned.

“But Jeff, no one is here but us. No one is looking for me. No one cares that I’m gone. No one is going to tell anyone about anything!” She purred as she climbed up onto his lap and straddled his legs.

“Besides I know what guys want. I saw you looking at my pussy this morning. I saw how you were looking at me today as well!” She moaned as she wrapped her arms around his neck. She ground her pussy against his hard throbbing cock as she kissed him deeply and passionately.

At first Jeff didn’t return the kiss but his cock could feel the heat and wetness of her pussy as she shoved her tongue into his mouth.

Jeff reached down and cupped her ass cheeks with his hands and pulled her against his raging cock. She moaned as he sucked her tongue and kissed her passionately back. She was rocking her hips back and forth on his cock as he thrust his hips against her molten pussy.

“PLEASE JEFF PUT YOUR COCK IN MY PUSSY RIGHT NOW!” She moaned as she lifted her ass up.

He quickly undone his pants and pulled his hard throbbing cock free. It was sticking straight up and Vicky wasted no time reaching down to guide it into her tight little pussy.

“OHHHHH GOD YEEESSSSSS!” She hissed as she sank all the way down to the base.

“OHHHHH FUUUUUCCCCKKKKK!” He growled as her hot wet tight little pussy gripped his shaft.

He leaned closer and took a nipple into his mouth as she gasped loudly and ground her pussy against his cock. He still had a double handful of her ass as he started bouncing her up and down the entire length of his cock.

Her pussy pulsed around his cock as she moaned, whimpered and gasped loudly. Her body trembled as she felt her first orgasm building up inside her molten pussy. She was on fire and his cock was the hose and his cum was the fire suppression.

“OH FUUUUUCCCCKKKKK YEEESSSSSS FUUUUUCCCCKKKKK MEEEEEEEE!” She screamed out as her orgasm slammed her young body.

Vicky’s ass was a blur as she slammed herself down over and over again. Her ass cheeks were slapping his thighs as he sucked and chewed on her nipples.

Jeff was grunting with every thrust upwards into her spasmodic pussy. The room was filled with the sounds of their sexual frenzy. Both of them racing towards a common level of pleasure. Their bodies straining to get there faster and together.

“OH GOD I’M GOING TO CUM!” He warned her.

But instead of her climbing off of his cock, she moaned softly into his ear.

“FILL MY PUSSY UP DADDY!” She moaned.

That triggered Jeff’s brain and his body slammed upwards against her downward thrust. As they connected together, his cock erupted just as she screamed out in pleasure. Her pussy clamped down on his spurting cock as it milked him for every single drop of his precious cum.

“FUUUUUUUUCCCCCCCKKKKKKKKKK YEEEEEESSSSSSSSSSSSSSS DADDY FILL ME WITH YOUR CUM!” She moaned.

Jeff’s body shuddered as he emptied his balls into her welcoming womb. She continued to grind her pussy against his cock as her body convulsed and shuddered. They held each other tightly as they rode out their pleasures.

“OH GOD YEEESSSSSS BABY GIRL!” He groaned as he looked up into her eyes.

Gone was the lost lonely look that haunted her eyes. They were bright and sparkly as she looked into his eyes and smiled at him.

“Daddy do you think that I can stay here with you forever?” She purred as she kissed his lips.

Jeff wondered if that would be possible.

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