Babysitter Takes Advantage

by Small Penis


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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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By Roleplayer1234 (Edited with Ginger)

Jessica looked at herself in the mirror, smiled, and said, “Oh yeah, William Douglas, you’re in big trouble.”

The 18 year old giggled as she did the final touch ups on her long black hair and makeup that perfectly accentuated her big brown eyes. The Soft yellow summer dress really brought out the smooth chocolate colour of her soft skin.

William Douglas is her employer, and has been for the last two years. Ever since his wife had disappeared and she had responded to the newspaper ad he posted for a babysitter. His 8 year old son adored Jessica and swore he would marry her one day. This made her job much easier. Now she was going to be attending college and she needed a car badly. With the money she made she knew she could afford the payments. The problem was the down payment. No matter how hard she tried she just couldn’t save up enough money for it. But she had a plan.

She went to the Douglas home and let herself in. Tonight was the perfect night to pull this off as William was off to meet some potential customers who were arriving in from Japan on a late flight. That meant little Drew would already be in bed.

William Finished tying his tie and put his jacket on hoping he didn’t get there too late but also hoping the plane would be on time so he could come back home and go to bed. This wasn’t necessary. He knew that. But it always seemed to work well for him to put more than was needed into his work. He finished dressing and checked his hair in the mirror and sighed heavily. He may be a successful business man but that was where it began and ended. He had never been good at sports. Nor had he ever been very lucky with women. He learned early in high school that girls would always treat him like a gay friend or ignore him completely. He heard the front door and smiled knowing Jessica had arrived. When he was her age he had never been interested in African American girls. But he had no memory of one that looked as beautiful as Jessica. He grabbed his briefcase and hurried down the stairs.

When Jessica heard his heavy footsteps on the stairs she looked up at him with the sweetest smile she could muster. Yes he was 14 years older than her and at least 75 pounds overweight. His hair was thinning and half of what was left was already turning grey. Plus he had those annoying glasses. The kind that his grandpa should be wearing. But she needed money and she was determined to get it.

“Hi Mr. Douglas.” She said as sweetly as possible as though she was ecstatic to see him.

William looked at her and smiled mildly surprised. Jessica had always been a sweet smiling person around him but this seemed even beyond her. “Good evening” he responded, “I really appreciate you coming over so late. I’ll try really hard to be back before 2 a.m.”

It’s perfectly fine Mr. Douglas. And if its ok I have something I need to discuss with you when you get back.”

“That’s fine Jessica. I’ve been thinking it’s about time for a raise myself.” He said, chuckling as her face lit up. “But for now I really need to get going.”

By the time William had returned he walked into the house and was shocked. All the lights were off but the room was lit with soft candlelight. Jessica Emerged from the kitchen carrying a glass of wine as she sauntered over to him. “Welcome home Mr. Douglas.” She said in the most seductive whisper she could manage.

William took the wine trying to swallow the lump in his throat as he look over her body realizing she was wearing nothing but a sheer baby doll teddy, matching thong and a pair of 4 inch stiletto heels.

“Wh..wh..whats all this?” Stammered William.

Jessica smiled as she laid both her small hands palm down on his chest. “This is just me thanking you for being such a good boss. I remember you mentioned a raise?” She continued, “I was hoping for more of a bonus” She said leaning up to his neck and kissing it softly.

“A… a bonus?” Croaked William.

“Mhm” Cooed Jessica. “I was thinking like $2500. It would really help me for the down payment on my car.” She said sliding her hand down over his plump belly towards his crotch.

It suddenly hit William like a wall of bricks. She was trying to seduce him for money. On one hand this completely offended him. He knew he had so much more to offer in a relationship than money. He was a nice guy and very smart and he was a giver. On the other hand this wasn’t a relationship. Besides, how many times had he masturbated imagining the things he would do to Jessica if given the chance. And now she needed something from him and it was obvious she would do anything to get it.

“Well” He said smiling, “You would have to be a very naughty girl for a sum that large. But we might be able to work something out.” He said sitting down on the couch. “I’ve been admiring your lips ever since you started working for me.”

She took his queue and immediately sank to her knees. “I can be as naughty as you need me to be.” She smiled and quickly undid his slacks and reached into his briefs and pulled out his rock hard cock. She froze and her mouth dropped open.

“Getting Shy?” He asked curiously.

“Ummm… is… is that completely hard?” She asked looking up at him.

William felt the rush of embarrassment flooding his face. He knew ever since high school that he wasn’t very well endowed. But his wife had never complained about it. In fact no girl ever had.

“Yes that’s completely hard.” He said slowly.

His tone of voice made Jessica nervous. She needed the money no matter how tiny his cock was.

“I’m sorry…” She started to apologize but was interrupted by William.

“I’ll add $500!” He said quickly becoming more desperate for her touch.

Jessica looked up at him surprised but thoughtful. It boggled her mind that she just insulted him and instead of getting upset at her he actually offered more money. Had it really been that long since he had gotten attention from a woman? Every guy she had ever been with had always been dominant and she loved that. But she couldn’t explain the feeling she got when he just caved for her. Adrenaline, excitement and empowerment swept over her and the she felt the urge to push further.

“William” She started after taking a deep breath. “I have to tell you this is the smallest dick I’ve ever seen.” She said watching his reaction closely. “I think $3000 is enough for me to touch. What do you think?”

She stopped talking ready to break down in tears and beg for forgiveness if he gets upset. William looked down at her speechless. This teenaged girl 14 years his junior completely disgraced his manhood yet was still talking money? How dare she! Jessica reached out wrapping her small fingers all the way around his small penis and all resistance left his body and he let out a moan that begged for her to continue.

“Please don’t stop! Oh my god that feels so fucking good!” He said.

Jessica giggled. It wasn’t on purpose. The relief from putting on everything on the line combined with the realization that she had more power over William than she realized just made her bubble over and rather than say something stupid she just started giggling. But once she started she couldn’t stop.

“What’s so funny?” William asked confused.

Jessica thought quickly. “It’s just so small! like my hand covers it” She said as she continued jacking him off.

William moaned loudly and his hips started bucking. Jessica knew he was close to cumming and she immediately pulled her hand away.

Williams moans turned into groans of despair. “What’s wrong?” He asked desperately.

“Well for one” Jessica said sternly, “I haven’t seen any money. Secondly I said $3000 for me to touch you. I never said anything about letting you cum.”

“It’s in my safe.” William whined. “I’ll get it for you.”

“No!” Yelled Jessica. “I’ll get it. “Give me the combination.”

“But but… There’s a lot more than $3000 dollars in my safe.”

“Good” Said Jessica smiling sweetly. “There might be enough in there for you to have an orgasm tonight.”

Her confidence was more than William could stand. “34-28-46.” He said resignedly.

“Good boy.” Jessica said petting his head condescendingly. She got up and went to his study and counted out $15,000 and came back to the couch. “Now” She said laying the money on the couch in stacks of $1000s, after my first $3000 there are 12 stacks left, for me to keep touching you, you have to let me take another stack. If I stop you have to give me another stack for me to keep touching you. Deal?”

William stared at her in disbelief. The idea turned him on so much even though in the back of his mind alarm bells were ringing telling him this had already gone too far, Suddenly he felt her fingernails sharply digging into the fleshy meat of his ball sack.

“Do we have a deal?” Jessica asked slowly but sternly.

“Yes. yes yes yes!” William whined as his faced twisted in pain he felt powerless next to the teenage girl holding his most prized possession in her hand.

“Good.” She said releasing her grip she grabbed three stacks of money plus a fourth one and continued rubbing his cock. “I really can’t believe how tiny this thing is.” She said amused at how every insult seemed to drive him closer to the edge. “It’s like my pinky.” pulling her hand away as his hips started bucking. “Continue?” She asked looking up at him.

“Yes please” He said hoarsely.

Jessica smiled. This is too easy, she thought to herself. She grabbed another stack and started going again. “I should Take pictures for my friends. I bet they would love at this tiny thing you call a dick.” She giggled and pulled away as William was already on the verge. “You love this don’t you?” She asked not even checking to see if he wanted to continue. She just grabbed another stack started rubbing his balls.

William couldn’t stand it anymore. “Take it all please! I just want to cum already!”

Jessica pulled back and slapped his balls not too hard but not gently either. “That’s no way to talk to me! I own you, you pathetic bitch! You’re lucky if you get to cum at all tonight!”

William cried out in pain. “I’m so sorry Jessica please forgive me! Please!”

“I will take the rest of the money. Just so you can cum.”

“Thank you!” He said in relief.

“Go ahead.” Jessica said sitting back on her heels. “Cum.”

“What?” William asked in shock.

“You wanted to cum? go ahead. You have one minute.”

William caved again and grabbed his small dick with three fingers and started jerking while he watched Jessica rubbing her boobs through her shirt. It took less than 30 seconds and his eyes rolled back in his head while a few drops of cum dribbled out of his cock. Jessica laughed loudly. That is the most pathetic thing I’ve ever seen! But thanks for buying me a car. She got up and walked out.

The End.

 

4 Comments

  1. Yes ! An interesting detail the author offers us is at the ending. Sure William is desperate to cum all through the encounter but in the end – like all little dick losers – he only dribbles out a few pathetic drops of cum. All that money and humiliation and desperation, all for a few pathetic cum drops. Little dick losers – like me – are really the most pitiful men on the planet. We deserve the insults and humiliation and abuse that we receive from real men and women.
    Cheers LittleDickWanker Jay Anthony

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