Since he first discovered the Internet and the excitement of browsing erotic sites, Tom had been fascinated with the incest and intergenerational sections of the sites he found. A special interest for him was those stories involving young men and mature women. He had fantasized about older, more experienced women since he was in his early teens and now, at twenty nine, he spent many an hour cruising online chat rooms to live out his dream vicariously while watching others connect. When not online as an 'observer', he was reading all the stories he could find and taking his cock in hand, would stroke himself to many a lonely orgasm.
Every night, he would rush home from his boring job as an accounting clerk and turn on his computer to begin his adventures. He would often even forget to eat and find himself going to bed more and more frustrated every night. However, before crawling into bed for the night, he dutifully called his mother to wish her good night and find out how her day went. They had always been close since Tom was an only child and his father had left them for a younger woman when he was only five. His mother always called him 'her little man" and the 'man of the house" and he grew up maturing fast.
After Tom left home for college, his mother met and married a local carpenter who was often out of town on contracts for weeks at a time. His mum was only around forty at the time and a very attractive and needful woman. After being without a man for so long, she desperately needed a man to fulfill her sexual desires, which were many and varied. Unfortunately, this was not the man for the job since when he was at home, he spent most nights drinking with his buddies or falling asleep in front of the television. Charlene was very unhappy but didn't want to upset her son so Tom was never aware of his mother's despair.
Then one night, just before he shut down for the night from the chat room called 'Mature Women Loving Younger Men", a new person joined the group named Dolly50. When he checked her profile, he read with interest that she was 51 years old, married (but unhappily) and had always dreamed of the strong robust young man who would take her to his bed and makes long, sexy love with her.
Tom watched until she signed off an hour later as other men online tried to engage this lady but she did not appear particularly interested in getting into any prolonged conversations with any of them. This struck Tom as curious; if so reticent, why was she there in the first place. Perhaps it was just idle curiosity and this intrigued him. However, he had to go into work early tomorrow so decided to turn in; with a good night to everyone present, TomCat signed off for the night.
For the next few nights, as soon as he signed in, he noticed Dolly50 appear; neither of them joined the sometimes inane chatter that often populates such chat rooms until around 8:00 pm, a message popped on Tom's screen – Dolly50 was inviting him into a private chat room to get acquainted! Following the directions he was given, he signed into the private address and moments later, she appeared. It was as if his every dream might be realized as they carefully felt each other out.
She admitted to a long running fantasy of having a younger less experienced man to teach the secrets of how to please a woman and she was anxious to experience the stamina of a virile man. She admitted to feeling ignored and sexually frustrated by a husband who simply didn't care and that the marriage was completely loveless. As they continued to correspond over the next few weeks, they became more and more open with each other as to their fantasies and sexual fetishes. The more they chatted, the more they found they had in common.
After a month and a half, Tom admitted that each night after they chatted for a couple of hours, he went to bed and masturbated at the thought of having sex with her. There was a prolonged pause with no reply; he checked to see if she had left the room fearing that he may have gone too far too soon. Then, with an almost hesitant had, the letters appeared on his screen; "I do too"
A flurry of messages flew back and forth as they became more and more intimate. Within minutes, they were sharing the most amazing online sex either had ever had. Actually, it was the first either had ever experienced and they came together! As they relived their experience, it was Dolly who asked if Tom wanted to meet.
