This is my first story so please be kind. I'm about to share one of my fantasies with you; one I enjoyed all through high school and college. My neighbour was freaking smoking hot and I loved the way she dressed. I've never had a writing class so please help me out with any issues with my writing.
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David was your typical nineteen years old. He'd been dating Theresa for the past year and they had a comfortable relationship, but never talked about marriage as Theresa was going away to school next fall, while David graduated a year early from high school and was taking classes at community college. Sure he'd wanted to attend a major university but his parents were unable to pay for his college so David figured that he would find as many jobs as possible to save up money to attend a state school for his junior and senior year.
Dating was never an issue for David as he was six feet tall and in very good shape. He loved to swim and ride his bike to do so and Theresa would tease him by telling him that her girlfriends would talk about him.
David knew that Theresa had been with other guys before him and that was what he loved about her. She was pretty open with her sexuality and willing to try just about anything; in fact, once she was aroused there was no stopping her until she came. The young lovers enjoyed a healthy sex drive and would try to sneak away to get it as much sex as they both could. Living at home can be a bitch.
When it came to sex nothing off limits for David and going down on Theresa was one of his favourite things to do her and thankfully she loved having him eat her pussy. She loved to rub her own clit when he was inside her and he loved the feeling when she would orgasm while he was fucking her. Yes, Theresa was just one of those girls who loved sex and David knew that a girl that wild just doesn't belong to one man and he was just happy to enjoy being with her regardless of the future heartache coming. Since they were not married he was okay if she enjoyed other guys, and dreamed he could watch her with one of her sexy girlfriends. The young couple never talked about long-term relationships and that gave them the option to see others. Granted, they were young and neither had a clue what a real relationship meant.
Now David had had a secret crush on Karen for years. She was the hottest milf on the block and fucking her had been a fantasy of his from the day he first met her. He guessed she was around thirty five and together with her husband Dean they have one child named Christopher. Now babysitting wasn't something that David enjoyed but Christopher had the latest Xbox games and then there was Karen. He loved stealing glances at her as she would wear sexy cocktail dresses when ever Dean took our out. Christopher was eight who enjoyed playing Xbox and for the most part he was a pretty cool kid as he loved to play video games which made watching him easy; not to mention the fact that every time David watched Christopher Karen would order a pizza for dinner. Life had started to become interesting when Karen asked David to babysit as in his eyes the job wasn't babysitting but getting paid rather well to be Christopher's older brother.
Karen would ask for David's help every now and then; from taking care of the yard, to simple home improvement projects along with watching Christopher. One night Karen had to attend a company function for her husband Dean. She'd told him that she really did not want to attend but felt had to play the perfect wife and stated that she would order a pizza and that she'd purchased a couple of new games.
One of the perks of the job that David enjoyed was watching Karen and waiting to see her when she was ready to present herself. What he enjoyed most about her was how she dressed, classy and very sexy and also the fact that she always wore hose when she went out, something which girls his age never did. He wasn't sure why he found it sexy but he loved gawking at Karen's legs tried his best to get Theresa to wear stockings but she would never would concede to his fantasy. There was something about a woman in a sexy black dress and black hose that drove David wild!
Even though David has Theresa he still enjoys masturbating and for the past year he'd been masturbating to images of Karen when she would come in and rip off her dress, then peel her pantyhose down so he could get his cock inside her wet pussy. Oh how he dreamed of touching her.
About a week ago Karen asked David to watch Christopher on Friday night. Normally Friday night was reserved for Theresa but things didn't work out as she had to go out of town and he had eagerly accepted Karen's invitation. His week was pretty normal and while it slowly progressed he became more interested in the weekend, wondering what Karen would wear and if he would be luckily enough to see something.
David had always thought Karen's European accent was sexy. He enjoyed chatting with her and at times felt that she was flirting with him but he was always too shy to make a move. What if his ego was bigger than reality? So during the summers he would cut her grass and in the winter shovel her drive way.
During the summer Karen would dress a little casual at home and loved watching her doing yard work due to the fact that on most summer days she wouldn't wear a bra under a tube top, tee shirt, or her loose fitting blouses and it seemed that Karen loved to "accidentally" show her breasts to men and David was always there trying to get a peek.
Finally it was the Friday and David couldn't wait to get past the work day. Each minute lasted an hour but during the slow periods at his job he was able to enjoy a few fantasies about Karen. Finally after a painfully long slow day at work the clock finally reached five and David drove home with an erection due to thinking about Karen and what dress she would wear.
Once home David said hello to his parents and went up to his room to take a shower. All he could think about was Karen and how he wanted to have her. Should he take care of himself or hold off just in case? He decided to hold off just in case there was remote possibility that she might be interested. He quickly dried off, put some product in his hair, and dressed nice but casual.
After a few agonizing moments it was finally time to go over to Karen's house. She greeted him at the door wearing a terry cloth robe; giving him a hug and quick kiss on his cheek. Then she started to talk about the night, telling him that the pizza would arrive around seven and that if he had any issues he was to call her on her cell phone.
David first noticed her stilettos as she walked down the stairs, then her black sheer hose and finally her short black cocktail dress. Once downstairs she turned around and looked at him, "Well?"
David noticed the dress was backless which meant she was braless, "You look amazing!" He could feel his arousal start and prayed that his cock wouldn't become hard.
She blushed, "Thank you."
Damn if I had a woman like that I would use her every night, David thought to himself. His erotic thought pushed his body over the edge and his cock was now at full mast as he watched her doing some last minute things before her big night out. Then she sat down in the kitchen, her skirt rose high on her thigh and she called for David.
David was a little worried walking into the room with a hard on but if she noticed she didn't say so. As he moved closer she put something down on the table. He moved next to her, his hard cock just inches from her face and from this angle David was able to look down her dress and see lots of cleavage. Oh her legs, the helm of her dress had to be less than two inches from her pussy David thought to himself.
He fought back the urges to reach down, slip his hand under her dress, and cup her breasts. Oh how he wanted to have her. Karen sensed his arousal and impressed with his size, leaned forward trying to tease him more; pretending that there was something for him to look at. She did this knowing full well that by leaning forward more of her cleavage would be exposed and sure enough he took the bait.
Before things could get out of hand Dean walked downstairs, over to Karen and like a perfect gentleman he held his hand out for her. She gave Dean a wicked smile. Karen tried to think of any last minute instructions but didn't have any as her mind was focused on having that young man in her bed. They said their goodbyes and Karen gave Christopher a quick kiss on his forehead. Then they left.
David and Christopher played Xbox and ate the pizza. Around nine, Christopher fell asleep so carefully David reached under, picked him up, and carried him to bed. When David left Christopher's bedroom he noticed that Karen's bedroom door was open and like any young man he had to peek in. From the day she'd moved in he was in lust with her. She was 100% cougar and Karen was one Milf that he had to get a piece of. He wanted to see if she owned any toys but decided it would be best not to worrying she had a web cam in her bedroom and was testing him. David made his way back down to the family room.
Around eleven David heard the garage door open. Karen came in first and asked for his help. Dean is a diabetic and Karen needed it help to get him in bed. She told him how Dean had enjoyed a few drinks too many and eaten too much. She told him Dean was okay but needed his help to get him in bed. David felt kind of strange helping a wife carry her husband man to his bedroom so once Dean was in bed he left the room. About five minutes later Karen came downstairs and looked at David with a funny look on her face.
Karen smiled, "David can I ask you something?"
"Of course!"
