This is my first attempt at writing stories, sexual and otherwise, so any constructive criticism will be greatly appreciated. Hopefully there will be many stories after this. This story is a work of fiction.
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Jessica looked at herself in the mirror and smiled. "Oh yeah William Douglas. You are 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 color of her soft skin.
William Douglas was her employer and had 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.
