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Simple Simon 1

"Simon Learns a Lesson"

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Simon was a simple soul. And so too was his mind.

School for Simon was both painful and embarrassing for him and so it was that he dropped out after just four years. It wasn’t him who made the decision but his mother and father who, realizing it was nothing more than a waste of time for him and whoever tried to teach him, agreed with the school principal that they would pull him out.

“It’s better for all concerned,” he’d said gravely.

Simon was relieved! No more teasing and no more beatings from his classmates. No more interminable days of listening to the teacher go on and on about stuff that he just didn’t understand. And no more scurrying home from school looking over his shoulder for sign of anyone chasing him.

Yes it certainly was better for him!

His education from that day forward consisted of following his dad around on the odd-jobs he did for some of the wealthier residents on the other side of town. Theirs was a pastoral community, far away from the noise and hustle of downtown.

The gated mansions looked like castles to Simon with their ten and twenty-room homes surrounded by two or three out-buildings housing anything from car collections to gardening equipment to private saunas or bowling alleys. One home even had its own indoor tennis court.

And of course there were swimming pools at virtually every home. And every one of them needed to be cleaned and maintained.

His father, Bill, William to his upscale clients, took care of all their maintenance needs from mowing lawns to cleaning pools to flushing out eaves troughs. It kept him busy upwards of ten to twelve hours every day, even weekends.

In fact, Simon couldn’t remember his father ever taking a day off. And neither did Simon after that last day of school.

Over the years he learned the ins and outs of the proper care and maintenance of every one of his dad’s clients. They smiled at him whenever they spoke. Their smiles were those that you used when speaking to a small child.

He didn’t mind. They were mostly kind to him, in a distant and condescending way, but still kind.

One day he learned the downside of their patronizing kindness.

He was trimming some enormous hedges that closed in the pool area of one of the swimming pools.

He was hidden from view and he heard some female voices approaching. He knew without looking, it was the teen daughter of the homeowner with some of her friends. Her name was Jennifer. He didn’t know the names of any of the other girls.

She was a pretty girl whom Simon had watched over the years as she grew. She would lounge around the swimming pool dressed in skimpy bikinis, knowing full well that both Simon and his father could see her clearly as they worked. She and her friends were all developing into beautiful women. He couldn’t help but admire them from afar. He knew better than to try to talk to any of them though, or even to nod in their direction. Working with his father had taught him that there was a great gulf between “his kind and their kind”.

The girls were laughing amongst themselves and splashing up to their knees in the cool water when the girl’s mother came out.

“I know it’s very private back here and it’s very hot,” the woman said, “but William and Simon are on the property doing some work today. So no topless sunbathing please girls!”

The girls burst into uproarious laughter and Jennifer said, “Yeah right! Like Simple Simon would even know what he’s looking at!”

The girls laughed louder at that.

“Now Jennifer,” her mother said, “He can’t help being the way he is.”

“He’s a half-wit!” Jennifer said, “He wouldn’t even know what to do with a set of tits!”

Her mother frowned and gave up. She knew better than to try to get into a battle of wits with her daughter. She knew Jennifer’s cruelty knew no bounds. She might even trot out some embarrassing facts about her mother when provoked.

As for Simon, his face burned with shame at the nick-name Jennifer gave him. He was immediately drawn back to his school days and the teasing he suffered at the hands of his classmates.

He was almost twenty-two years old then, but his emotions and intellect were still that of a child. Her words scarred him like a lash.

He ran off, the job of trimming the hedge unfinished.

He didn’t care right now. All he cared about at the moment was getting away. He ran as fast as his legs could carry him.

After running for almost five minutes he found himself in one of the outbuildings belonging to the same property. It was the furthest shed from the main house and was used to store the gardening equipment his father used to maintain their lawn.

Simon threw himself down on the ground inside and wept. His tears flowed without stopping for several minutes.

When he was all cried out, he sat up and took in his surroundings. The barn was dim and small motes of dust drifted lazily in the air. He watched them for a while and began to smile. He put the experience with Jennifer out of his mind and thought about the things he liked. His dad, his mother and the dinners she prepared for them when they returned home from a long day at work. Simon was indeed a happy boy who loved his mother and father very much. And they loved him.

When he stood up he realized that his clothes were filthy. The dirt from the barn floor had stained his pants and his shirt.

Simple he may have been, but his mother taught him that cleanliness was next to Godliness. Being a well-behaved boy, he stripped off his clothes and wandered out the back door of the barn. There was a stream about twenty paces away from the doorway.

He carried his clothes to the water and cleaned the mud and dirt away. When he was finished he laid them flat on a large rock by the waterside to dry.

It was so hot! The humidity had the sweat pouring off his skin. He waded back into the water and dove in head first. He splashed around to his heart’s content and eventually climbed out of the water and onto the shore.

When his feet were back on dry land he stretched and gazed up at the sun. He smiled and sat on the rock beside his damp clothes.

Suddenly there was a loud rustling in the bushes.

He looked up startled to see Jennifer staggering through the undergrowth with a look of amazement on her face. She was still wearing the bikini she had on earlier but had pulled on a pair of white denim shorts over the bottoms. She was staring down at his midsection with her eyes wide and her mouth hanging open.

“Oh my God!” she said, “Where did you get that?”

“What?” Simon said, being too surprised to take in what she was saying. What was she saying?

“That!” she said, pointing deliberately at his penis, “That thing is huge!”

“Really?” Simon asked, “It is?”

“How did a half-wit like you end up with such a huge cock?” she exclaimed.

Simon frowned and stared at her angrily. He grabbed his wet clothes and stalked off to the barn.

When he was inside he was surprised to see she had followed him.

“You shouldn’t be in here,” he said, “You could get hurt with all this equipment around.”

“Never mind that!” she said dismissively, “I want to know more about your cock!”

“What about it?” Simon said.

He’d never really thought about it much. He used it to piss and he sometimes had trouble fitting into tight shorts or pants. Other than that, it wasn’t something he spent much time thinking about.

“I mean it’s huge!” she said.

“It is?” he said.

“How big does it get?” she asked.

“What do you mean?” he asked in confusion, “Is it supposed to get bigger?”

“Yeah!” she said, “When you’re horny, you know? It grows when it gets hard, doesn’t it?”

“Hard?” he said, “I don’t think it’s ever done that.”

She looked up at him in shock, tearing her eyes away from his penis for the first time since she saw him.

“Are you saying you’ve never had a hard-on?” she asked incredulously.

“What’s a hard-on?” he said.

“Oh my God!” she said, “You haven’t! Your cock has never been hard? Even while you’re watching me and my friends sunbathing?”

“No,” Simon said.

He was beginning to feel uncomfortable with this girl staring at his penis and talking so much about it. He couldn’t figure out what the big deal was. She seemed to think it was big. He’d never considered it big. As far as he’d given it any thought, he’d just assumed that every man had the same as him.

“Don’t you ever touch it?” she asked.

“Yes, when I have to piss,” he said.

“So” she said a little more quietly, “You never rubbed it? Never ran your hand up and down on it?”

“No,” he said, “Why would I?”

She looked back up into his eyes once more and he could see something in her face changing. Gone was the cruel tease. The expression on her face was one he’d never seen before. She looked almost, hungry.

“Can I touch it?” she asked with a smirk.

“No!” he said and drew back from her, “Don’t touch!”

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“Please?” she asked in a little girl’s voice, “I want to see if I can make it hard.”

“Why would you do that?” he asked as he put a table between the two of them.

“After it gets hard,” she said softly, “there’s lots of stuff can happen. Really good stuff!”

“Really?” Simon asked.

He was wondering if he allowed her to touch him if she was just setting him up for more teasing. Other kids he’d known in the past had done that sort of thing.

“Oh yeah,” she said as she sidled closer to him, “Just let me touch it, and I’ll show you.”

Simon hesitated and looked around the barn for someplace he could escape from her. With her moving around the table he’d stood behind, she had cut off any way for him to get away.

She stepped right up to him and stared into his eyes. Very slowly, she placed her hand on his penis. She sighed when she felt its fullness. She’d never even seen a cock as big as his, much less held one in her hand.

Even soft, her hand didn’t completely cover its length.

She placed both her hands on it and held it gently. She started to rub her palm over the head while stroking with her other hand along its length. Her eyes grew wide as it began to respond. Before too long, it was longer than both her hands put together. The head mushroomed until it wouldn’t fit into her palm anymore. She gripped it firmly and gave a small chuckle as it reached its full size.

“Oh my God!” she whispered, “This thing is huge!”

Simon, completely out of his depth, could only mutter unintelligibly. He looked down and was amazed at how large his thing had gotten. He’d never seen it the way it was right now and it scared him a little.

“Ooh,” she cooed as she placed it between her thighs and flexed her hips back and forth, “Let me play with it.”

Simon grunted and leaned back against the wall. He couldn’t back up any further.

“That is so awesome!” she whispered as she humped back and forth along its length.

She put her arms around his back and locked one thigh around his hips. She leaned forward and placed the tip of her nose against his.

“Would you like to see mine?” she asked with an impish grin.

Simon shook his head and gasped.

“Girls don’t have things!” he stammered, “Girls are different!”

“Yes we are,” she said huskily, “Girls are different so we can have fun with boys!”

“R—, really?” he grunted.

“Oh yes!” Jennifer said, “Watch and see.”

She backed off of Simon’s penis reluctantly and then peeled her shorts down to her ankles. Then she gripped her bikini bottom and slid it down to join her shorts. Simon opened his mouth wide in disbelief. He’d never seen a woman’s private parts before. The only woman he knew was his mom and he’d never seen her there before.

Jennifer had very pale skin, despite all the tanning she did. It was almost the color of alabaster and her petite form was flawless. Her slit was bright pink and looked very small. There was a neatly trimmed tuft of brown hair, only slightly darker than the hair on her head, just over the top of it. It wasn’t more than two inches long and an inch wide.

She grinned as Simon stared at her. She unsnapped her bikini top and dropped it to the ground.

“Have you ever seen tits before Simon?” she asked coyly.

Her breasts were about the size of oranges and capped with bright pink nipples. She caressed them as she stared at him.

He shook his head and gawped as his eyes went from her chest to her pubis.

“Do you like what you see?” she asked.

He gulped and nodded as a high-pitched whimper came out of his throat.

“Now you sit down on that chair,” she said with a gentle push to his chest, “And I’ll show you how boys and girls have fun together.”

Simon staggered backward and landed on a straight-backed chair against the wall. As soon as his butt hit the seat, she straddled his thighs and pushed her belly against his. He could feel the heat emanating from her private parts against his thing. She was sliding her slit back and forth across the top of it and he was gasping for breath. This was something he’d never even dreamed of before.

He looked up at her and she grinned as she ground her vagina against his cock. She groaned aloud as she slid up and down its length.

“Ooh yes!” she whispered, “This is gonna feel good!”

She reached her hand to his cock and held the head to her opening.

Even as wet as she was, she couldn’t make the enormous head fit inside her. She ground against it again and again, grunting in frustration as she tried to make it go in.

“Oh my God, it’s big!” she groaned.

Finally the head slipped inside. She cried out as her lips stretched to let it in. She had never had a man this big in her life. Her experience with huge cocks was limited to the videos she could find on line. She started taking rapid breaths as she pushed harder and harder forward. She giggled to herself when she realized she sounded like she was giving birth. She thought to herself this cock she was trying to fuck was almost as big as a baby.

She closed her eyes and grunted again when she felt the head slip into her channel. From there, it was a simple matter of making small thrusting movements back and forth. Eventually, almost two thirds of his cock was inside her and she gasped as she orgasmed.

Simon didn’t know what was going on!

He had to admit that he liked it, but this was way beyond any experience he could remember. As she worked so hard to push his thing inside her, all he could think of was how wet and warm it was. He felt like he’d taken a damp sock and pushed his penis inside it; a sock that was way too small for it.

When Jennifer started trembling and gasping for breath, he was afraid he had hurt her.

She opened her eyes and Simon saw pure joy in there. She was smiling from ear to ear and she wrapped her arms around his shoulders.

“Oh my God!” she gasped “Simon! You’re amazing! I want you all the time!”

She kissed him then, shoving her tongue deep into his mouth and Simon was shocked. He let her explore his tongue and inner cheeks but was too stunned to respond in any way.

Then she started moving her body up and down. She grunted with every down-stroke and held him tightly with her arms and thighs.

“Oh yes!” she gasped, “Give it to me Lover!”

Simon leaned far back in the chair and his eyes rolled up in his head. His thing felt like it was in heaven. The movements she was making were giving him a strange feeling, a feeling like nothing he’d known in his life. He could feel it growing even though he didn’t know what it was. All he knew was he never wanted Jennifer to stop.

Without him even willing it, his hands went to her hips. He gripped her hard and stood up.

Jennifer’s eyes went wide and her mouth opened in shock.

Before she knew what was happening, he had placed her back against the wall. He started ramming into her as hard as he could. Being a laborer all his life, he was very strong. He was starting to scare her. She felt like she were riding an insane bucking bronco. He was out of control.

She grunted with each thrust and her back was bruised from the force.

Suddenly he thrust into her and froze in place. Both of them were gasping for breath and she felt like her insides were being flooded with a garden hose. Even before his cock went soft, she could feel the back-flow drooling out of her and running down her thigh.

When he finally relaxed, he stood back and stared at her in fright. There were tears in his eyes and he looked like he was about to run away.

She managed to pull herself together and extricate herself from his member. When it slid out, it fell with a plop against her thigh and a torrent of semen streamed out of her.

She looked down at herself. Her vagina was red and angry looking and her sparse pubic hair was thickly matted with cum. She looked back up at Simon and sighed heavily.

“Wow!” she said, “You were, wow! I feel like I was the virgin!”

Simon only stared at her with his expression drifting between confusion and...

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Written by Brent473317
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