Chapter 1: A Game Of Chance

It was a hot summer night in Philadelphia and Colin, as usual, was out with Sheryl. He probably wouldn't be home until late. With nothing better to do, Aileen went to the small alcove of their apartment where the computer was set up and signed on. Perhaps she would play a couple games of gin rummy, but what she hoped for most was that Ben would be online.

Aileen Reilly had been divorced for almost ten years. Even though she hadn't had a serious relationship since her divorce, it was only in the last year or so the absence of a significant other in her life had really made itself felt. The reason was because she did have someone significant in her life, her son Colin. They spent a lot of time together and did numerous activities, and it was always a blast being with him. She loved her son and was totally dedicated to him. His company had always been all she needed to be happy. But Colin was seventeen years old now and every day Aileen felt him move a few steps closer to leaving her and going out on his own. She was beginning to feel a loneliness and isolation she hadn't known since before Colin was born. She knew her boy had to grow up, but it saddened her that in doing so it made them grow apart.

Nearly two years ago Colin had met Sheryl and she eventually became his steady girlfriend. Their relationship had blossomed over the past couple years and they were now seriously involved with each other. It didn't surprise Aileen that her son would find a girlfriend so devoted to him. Colin was a handsome young man. He was over six feet tall, lean and muscular, and he had strong facial features with russet colored hair and insightful brown eyes. But aside from the way he looked, Colin also had the sweetest personality a boy could have. Aileen took pride in her son having grown into such a fine young man.

Sheryl monopolized most of Colin's time now and it resulted in making Aileen feel she had lost her best friend. Her main purpose in life, however, was to see Colin happy and if being with Sheryl did that, well then Aileen couldn't disapprove. It still didn't stop her from feeling lonely though.

Aileen held a nine-to-five job as a bank teller, which kept her busy enough during the week, but on the weekends she was off work and frequently found herself with nothing to do. She had a few friends, though no one she was especially close to, and once in a while she would do something with them. She had an older brother, Patrick, who ran a successful local pub and restaurant, but he was always busy with his own family or his business. While she enjoyed being in the company of Patrick and his family, she didn't want to infringe too much on their hospitality.

One way she found to alleviate her boredom was to play gin rummy via the internet. She enjoyed the card game but she hadn't really had anyone to play with in real life. She used to frequently play with Colin, they played gin rummy and a whole slew of other games, but ever since he began dating Sheryl, he didn't seem to have the time. So, online she found a place where there was always someone wanting to play a friendly card game anytime she felt like it.

Online is where she met Ben. He became a frequent and then favorite companion to play cards with. They would communicate with each other by way of the game's chat room during their play. They talked to each other about what was going on in their lives, frivolous things at first, but then more intimate. They became good friends.

It wasn't after too long that they began communicating more by instant messaging than during a card game. Ben was twenty-two and Aileen was thirty-six. Aside from similar tastes in movies and music, Aileen often wondered what Ben saw in her that made him always seem so eager to be talking with her. She didn't understand why he would want to spend so much time talking to someone so much older than him, but she really enjoyed his company and was flattered by his attention. Ben's company had become a decent substitute for Colin's.

Tonight, when she saw that Ben wasn't online, she felt a bit disappointed, but then about twenty minutes later, she saw Ben's screen name, Bender069, pop up indicating he had just signed on. Aileen felt a thrill run through her from seeing her friend now online. With her own screen name, IrishRose36, she instant messaged him.

Aileen froze in the middle of typing a response when she read what Ben said. She was shocked. While they had discussed their love lives with each other, neither of them had said anything so direct like that before. Their conversations always stayed friendly and polite, but what Ben just said indicated their relationship might be going in a new direction. Aileen wasn't sure how to respond. Should she feel offended? She didn't. In fact, she felt somewhat... aroused. Before she could type something Ben typed more:

Aileen felt a shiver run through her body. She couldn't believe she was letting this conversation continue in this direction but she couldn't help it.

Ben went into luscious detail describing what he would do to her longing cunt. He talked about touching it, exploring it with his fingers, fondling her most private pleasure zones. Then he started to describe performing cunnilingus on her. What he wanted to do to her sopping wet pussy with his tongue. He wanted to play with her clit, stick his tongue deep inside of her, and slurp her juices. Then he talked about feeling her breasts, how he longed to touch them, to suck on her nipples, how wonderful he thought they were.

As Ben went on describing the things he wanted to do to her, Aileen undid the sash of her blue terrycloth robe. She slipped her hand inside and then under the white cotton tee shirt she wore. She brought her hand up to her full breasts, her nipples were very hard and erect. She rubbed her finger tips over one of them and tweaked it, and then she did the same to the other. The sensation sent chills all over her body, most strongly felt in her pussy. Aileen slid her hand down her tummy, her fingers made contact with the waistband of her panties, slowly she slipped them inside and her hand continued on its southern course.

Her fingers made contact with her pubic hair, it was wet, and the further down she went the wetter it got. She was already in a very high state of arousal by this point and when her hand brushed over the lips of her hungry cunt it sent her to an even higher plateau. She took in a deep breath as she stroked her hand over her excited sex. She slid her fingers inside her pussy and a "MMMMMMMM" escaped from her mouth. She delved into herself with one finger and then two, running them along the inner walls of her cunt. Then she found her clitoris. The sensitive little nub was firm and it stirringly responded to her touch. She gasped at how good it felt. She played with her clit running her finger round and round in circles over it.

Ben asked her what she was doing. With her free hand she typed in a response and told him exactly what she was doing. Ben then informed her that he had removed his towel and was now totally naked as he was running his hand up and down his hard cock thinking of her. Aileen had never considered herself a very sexual person, never having had a very good sexual experience. Her husband, Fred, had been a selfish and mean lover, only engaging in intercourse when he wanted to and it always had to be his way. After her divorce Aileen rarely dated, she primarily focused on bringing up Colin, and in truth she had soured on the idea of relationships. She masturbated sometimes, but even then it was mostly by thought rather than touch. Sometimes to get to sleep she imagined the perfect loving man having his arms around her and making passionate but tender love to her, and touching herself didn't seem to please her as much as fantasizing in her mind did.

But now something had come over her and her body felt truly alive and sensual. The thought that Ben was actually naked and so excited by thinking of her was making her feel hornier than she ever had before. She typed about doing things to him that she never thought about doing in real life, or had done but not really cared for, but now the idea of titillated her. She described touching his cock, rubbing her hand up and down it. She typed about taking his cock into her mouth and sucking on it.

Ben informed her that his cock was throbbing from her saying those things and that made her all the more excited. It also amazed her how much the idea of doing these things really appealed to her now. She was plunging her fingers in and out of her pussy now in a furious motion, imagining that it was Ben's cock pumping in and out of her. She felt something building up inside her. She felt she was close to achieving something grand. She typed to Ben that she was getting close to cumming, he replied he was too. She plunged her fingers deeper inside her, she was closer, she rubbed her clit with her thumb, oh so much closer. Ben typed that his cock was so hard it was ready to burst with cum for her. That did it, her body spasmed and her sopping wet cunt clenched around her fingers, wave after wave after wave of orgasmic pleasure shot through her as her pussy squirted its juice. She let out a loud "OHHHHHHHHHHHH" as she came.

She typed to Ben that she was cumming and cumming hard, and he replied that he was as well, that his cock was shooting cum all over the place. It felt devilishly good to her that she could make a man do that just by talking to him over the computer and that a man could make her feel this way. She hadn't known she had it in her, but now that she did know, she wanted more.

Ben and Aileen continued their cyber relationship for the next couple of months. They usually engaged in cyber sex on weekend nights when Aileen didn't have to worry about having to be up early the next morning for work. Also, now that it was September and school had resumed, she only allowed her son out late on weekend nights. She could pretty much count on him being out with Sheryl every Friday and Saturday. It comforted her on those nights to have Ben and she didn't have to be alone. Aileen felt some guilt over what she was doing and a part of her kept telling herself that a thirty-six year old woman shouldn't be doing these things with a person she hasn't even actually met. But that part of her was overshadowed by the sexuality that had been roused in her. It felt good to be doing this, good in a way she never expected to feel, and she didn't want to lose that feeling.

She was indulging her newly discovered sexual appetite and for the most part felt safe about the way she was doing it. She felt she could talk to Ben about anything because he could talk about anything to her. She could consider and explore erotic desires she never would have thought about doing in real life. Like sucking a cock, something she had never done before but Ben seemed to enjoy the idea so much she enjoyed playing along and describing how she would suck Ben's. After a while she began to really wonder what it was like, if just the suggestion of doing it turned a guy on like it did with Ben, how much more rewarding would it be doing it for real? She began to think she really might like to try giving a real blowjob.

Ben reciprocated her talk of fellatio with generous talk of cunnilingus. The actions he depicted doing to her pussy with his mouth made her more than curious to truly feel a man's hot breath and warm wet tongue roaming over her pussy. She masturbated more intensely than ever before, no longer only thinking abstractly about being with someone, but now touching herself with vigor. That she communicated what she was doing with Ben made it all the more thrilling for her.

Over the course of her association with Ben, Aileen discovered something about herself; she needed something more in her life. Her son would always reign supreme in her life, but he was almost grown up now and starting to make a life of his own. Since Colin didn't seem to need her as much anymore, why couldn't she find someone else to share time with? She wanted a relationship, someone to be with in actuality. She was developing deep feelings for Ben, but she was afraid that with him being so much younger than her, he wouldn't want to be with her in a real relationship. Also, they lived so far apart; she didn't know if she could handle a long distance relationship. But Ben had shown her that she wanted more out of life and she thought she wanted it with him. She felt herself growing closer and closer to him every day. She trusted him. She felt she could tell him anything.

Before she had a chance to discuss these feelings with Ben, he once again did something that changed the course of their relationship. Maybe he was feeling that their affair was losing some of its spice which triggered him to say what he said. It was a Saturday night and they were chatting online as usual, but this time when their dialogue began to get more amorous, he made a drastic suggestion.