This is my first submission. I didn't intend for it to be this long, but I think it turned out ok. I'll let you be the judge. I made several attempts to edit it but figured it was good. I'm sure there are some typos and grammar issues, but I hope not too bad. I would like constructive critiquing, please.
Disclaimer: All persons in this story are at or over the age of 18. This is my own work of fiction. If there are any similarities to others and/or real situations, it is a complete coincidence.
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Timothy O'Clery, or Tim, was raised by my maternal grandparents until he was four and a half years old, then by Mother Beth after his grandparents died in an unfortunate accident. Let me explain, his mother had him when she was very young. You see his mother was impregnated by (technically his father, a guy that worked for Tim's grandfather, his name was Tony Figley) during his mom's eighteenth birthday party. Beth had been sheltered all her life and Tony took advantage of her ignorance. When his grandfather found out, he beat Tony almost to death, but the police arrived. I guess Tim's grandmother calls them. Tim's father was in the hospital for three weeks before pleading guilty and sentenced to fifteen years in prison. However, he didn't survive the first week. Apparently, weak guys like Tony the inside. His grandfather had been charged with assault and battery, but the case was dismissed due to Tony being killed in prison and no one to press charges.
Beth was sent to a boarding school for pregnant girls out of state where no one knew her. His grandfather wanted her to finish school on time and without being judged or picked on by other students. A year later Tim was born, and his grandparents became his primary guardians until shortly after he was four years old. The plan was to give Beth a chance to grow up, finish high school and college, and when she was ready, they would return custody of Tim back to his mom. However, that changed because, on their way home from picking her up after she graduated from college, Tim's grandparents were killed by a drunk driver. Beth survived the accident with minor injuries and was released from the hospital after 3 days.
Fortunately for them, Tim's grandfather was a very successful and wealthy businessman and had very loyal employees, along with his attorney David, that made sure Beth wouldn't have to deal with the aftermath of the accident. Tim's grandfather left everything to his mom and a very large trust for Tim once he turned eighteen and another trust fund for when he turned thirty. He made sure they were well taken care of in the event of his death. Tim's mom became the president of his grandfather's company, but because she was still only twenty-three years old, she would have to rely on the board member to run the company. This worked out well because it gave them time to become reacquainted with Tim. They grew attached quickly and things started to fall into a routine.
The year after Tim's grandparent's death, he started school and things were going well. Then after he started first grade, Beth was given an offer from the board members to buy the company for three hundred million dollars. Tim's grandfather's attorney David had always treated his mom as if she were his daughter even before his grandparents died. He explained to Tim's mom that it was an incredible deal, and she should take it. David also stayed on as their attorney to make sure all the house staff got paid and any other issues that would come up. David also helps Tim's mom invest any of the money if she chose to, either way, they wouldn't have to worry about money ever again. Over the years their love for one another grew stronger. His mom was at every school event, and he had the best birthday parties. One would say he grew up spoiled, but he would disagree. Though he had everything he wanted. Tim always appreciated his mom the most.
The estate Tim's grandfather left them, is a large mansion on 20 acres and had seven-bedroom eight bathrooms, to the main house, not including the pool house that had two bedrooms and a bathroom with a small kitchen. Then there is a four-bedroom four-bathroom apartment downstairs basement area of the main house, which is the sleeping quarters for the staff to maintain the house for them... The house was the shape of a horseshoe with the pool area in the middle and a pool house on the opposite end of the patio separate from the main house. Tim's bedroom was on the second floor overlooking the pool on one side of the house. Beth's room was set up the same way on the opposite side of the house. There were five bedrooms in between theirs all on the second floor. Each bedroom had its bathroom except Tim's bedroom shared a bathroom with another room. A Jack and Jill set up. This worked out well when he had friends spend the night.
When Tim turned thirteen, puberty struck him hard. He grew almost a foot taller that year. Then when he turned fourteen, he got into sports, mostly swimming, football, and track. He lost interest in football but stuck with track and swimming for a few more years. However, from being involved in the sports, his body took shape. Tim started to notice girls and they started to notice him. Beth never dated much because Tim was her number one priority. When he turned sixteen, David helped Beth pick out Tim's first car (a four-door Ford pickup truck). Even though she would let him stay out as late as he wanted, he would end up hanging out with her because his friends had curfews. Over the summers Tim's mom would let him have pool parties, Beth was cool about letting them have a few beers when the other parents were not around, this made Tim a lot more popular. One thing is for sure, Tim started to notice how hot his mom was. Her bikinis were so small, they barely covered anything. She had auburn hair, hazel eyes, she was so hot at five feet four inches 125lbs. Nice firm 34 C breast and nice shapely thighs and round ass. At that time, she was only 32, and Tim would be lying if he said he'd never thought about having sex with her. They had their gym in the house that got a lot of use from both of them. She never had to work, so when he was in school, she worked out or swim in the pool for something to do. This kept her body in great shape. She also liked to lay out by the pool and sunbathe nude. Tim discovered this one day when he got home early from school, putting his books in his room, only to look out the window to see his mom's gorgeous nude body soaking up the sun. He would watch her from his bedroom window and jerk off thinking about fucking her. She became the object of a lot of masturbation sessions after that.
Through his teenage years, Beth tried to date a few guys in hopes to find a father for Tim. One thing was for sure is she knew how to dress sexy. She would wear short skirts with lowcut tops that showed ample cleavage and came down just barely covering her panties. Her high heels show off the sexiest legs. Most of the people she dated just wanted to get in her pants or get their hands on her inheritance once they knew how rich she was. In her mind, none of the guys she dated were good enough father material for Tim. So, after a while, she gave up on dating anyone seriously. Just a few friends with benefits, but even those didn't last.
Just after Tim turned eighteen, he started his first and only real relationship. It was with a girl named Tammy Cohen. She was new to the school and already eighteen, but they hit it off the first day they met. She was so hot, kind of reminded Tim of his mom. Tammy was about the same height as Beth, but smaller tits, and her ass wasn't as thick, but sexy. She had auburn hair as well but with a little more hint of red, and her eyes were a hypnotic green. Tim's mom grew to like her as well. Mostly because she made Tim happy. Once Tammy's parents got to know Tim and his mom, they were cool about Tammy staying over on the weekends, mostly Friday and Saturday nights. They were comfortable because the house was so big, and she would have her room. Of, course they didn't know, there was a jointing bathroom.
The last Friday before graduation was a half-day, and the students that didn't have finals were done for the year. So, Tim invited Tammy to come over after school to hang out at his house. They spent most of the afternoon in the pool, grabbing, groping, and kissing each other. Tim's cock was hard all damn day because both Beth and Tammy were looking so good in their bikinis. After dinner, Tammy called her parents to see if she could stay the night to watch movies with them. Of course, they were ok with it and would be over to pick her up in the morning. They watched a romantic drama chick flick movie that showed a lot of tits, ass, and sex in it.
A little more than halfway through the movie Beth got up and said, "I'm tired and I'm headed to bed" and she wished Tim and Tammy good night. Tim assumed she got horny and needed to take care of it.
After his mom was out of sight, Tammy leaned against him and was rubbing her ass up against his cock throughout the rest of the movie. Tim was so horny he almost came in his shorts a couple of times. The movie ended and Tammy turned and started to kiss him right on the lips. He grabbed her ass and pulled her in close. She straddled his lap as they were making out and she started rubbing her hot cunt on his swollen cock. She started moaning and getting into it, Tim was sure he was about to get lucky, but then she pulled away and said, "I'm tired too good night". She gave him a peck on the lips, jumped to her feet, and went to her room.
Tim sat there thinking to himself, "what a fucking tease". he got up, turned off the TV, and went to his room. Tim would usually sleep in a pair of basketball-type shorts when he had company. Otherwise, he got used to sleeping nude in hopes his mom would come in to wake him up, see his cock, and want to fuck him. However, that hasn't happened. For some reason, that night he stripped nude for bed.
A little after midnight Tammy snuck into his room through the bathroom, where she took off her sleep close. Tim was lying on his side when she climbed into his bed and cuddled up with her back to him. Tim was so out of it, he thought he was dreaming that it was his mom in bed with him. Tim's cock was hard, and he was sliding it up and down between her ass cheeks. He could feel her warm softback against his chest, and he wrapped his arms around her and grabbed her tits. She began moaning when he rubbed and squeezed her tits with his hand. Her breathing started to get heavier, her nipples were hard, and she started to moan even more. She reached back and grabbed his cock. Stroked it a few times then angle it, so the head of his cock was at the entrance of her wet pussy. Tim could feel the heat from her pussy radiating on his cock. As his cock started to slide in, it was so warm and wet, yet so very tight. The pressure caused Tim to hold his breath as it slid in, it felt so good. Tim felt like he was about to cum right then but was able to power through it. Once he was in only a few inches, he felt resistance. He pulled his cock back then he pushed in again and felt the resistance again, he push a little more causing his mom to whimper and she pushed her ass into him. He pulled back slowly, then eased back in a little more, her pussy was getting wetter. As the resistance gave way, he heard her whimper as she exhaled. Her breathing got quicker and heavier and she started moaning as if she was in pleasurable pain. Her pussy was so tight, and she was becoming wetter and slicker, it allowed Tim to slide deeper into her. He got more than half of his cock in, then pulled back out leaving just the tip of his cock in her. Tim slid his cock back in going a little deeper, exhaling and moaning as he felt her pussy leaking around his balls. He kept pumping his hips, inching his cock deeper and deeper, and then started to have a steady rhythm.
