Chapter 1: A Game Of Chance

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Incest, Mother, Son, First, Oral Sex, Anal Sex, Masturbation, Slow, .

Desc: Incest Sex Story: Chapter 1: A Game Of Chance - Aileen and her son Colin have always been close, but as Colin approaches adulthood their relationship begins to drift apart until circumstances occur that bring them closer than ever. Part I of the A Series Of Matters Trilogy

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.

IrishRose36: Hey Hon, how are you?

Bender069: Doing pretty good here, how about yourself?

IrishRose36: I'm fine, and happy to see you.

Bender069: Me too.

IrishRose36: So what have you been up to?

Bender069: Just got finished taking a nice long shower after a hard day's work.

IrishRose36: You got all nice, clean, and fresh just to come and talk to me? LOL

Bender069: LOL Yeah, I did.

IrishRose36: Ha, it's Friday night, I bet you are getting ready to hit the town.

Bender069: No, I don't have anywhere else I'd rather be than here talking with you.

IrishRose36: You flatterer. You need to find a girlfriend and take her out.

Bender069: What about you? Why aren't you going out with a boyfriend?

IrishRose36: Because I'm not interested in that. Besides who would be interested in me? I'm old and fat.

Bender069: No you are not! I saw that picture you sent me, you're beautiful! What man in his right mind wouldn't want to go out with a tall redhead like you?

IrishRose36: You forgot fat.

Bender069: You're not fat, you're voluptuous.

IrishRose36: LOL that's just a polite way of saying "fat".

Bender069: Bullshit! My cock is hard right now just thinking about you.

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:

Bender069: I'm sorry. I didn't mean to be so forward. Please don't be mad.

IrishRose36: It's ok, I'm not mad.

Bender069: Good.

Aileen hesitated a moment, not really believing what she was going to ask, but thought, What could be the harm in it?

IrishRose36: Is it really hard?

Bender069: Yes

IrishRose36: Because of me?

Bender069: Always because of you.

IrishRose36: What do you mean?

Bender069: I hope you won't hate me for saying this, but I have been fantasizing about you for a while. I've gotten hard just talking several times but never mentioned it. I think I'm falling in love with you.

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.

IrishRose36: I don't hate you. In fact, hearing you say that has made my pussy wet.

And it was the truth, her pussy was wet. Aileen had never thought of cyber sex as something she would be into. She hadn't gone looking for this, but she had to admit, talking like this with Ben over the internet was awakening certain urges in her body faster and stronger than she could have imagined. She was horny.

Bender069: Oh God, Aileen, I wish I could see your wet pussy!

IrishRose36: What would you do if you saw 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.

{redBender069: How do you feel about role playing?

IrishRose36: What do you mean?

Bender069: You know... Pretending we were other people when we cybered.

IrishRose36: What roles do you have in mind?

Bender069: Promise you won't get mad at me?

IrishRose36: Of course I won't, you know you can tell me anything.

Bender069: Ok... what if we pretended we were mother and son?

Aileen just stared at the computer screen for a couple minutes not knowing how to respond. She supposed she should have been repulsed, but she wasn't. She was definitely stunned, but after all she and Ben had done together the idea of pretending to do something so forbidden was... exciting. Aileen felt a warm gush spread through her and goose bumps pop up on her arms. Her pussy had become wet just like the first night when they began to have cyber sex. Before she could respond to him though, Ben typed something else.

Bender069: I'm sorry, forget what I said, it was just a thought.

IrishRose36: No, wait. Um... how would we go about it?

Ben began to set up an elaborate scenario involving a mother and son being sexually attracted to each other. Aileen took her cues from Ben, and in no time they had fallen into their roles as pretend mother and son playing off each other in more and more explicit manners. The deeper Aileen got into her role, the more her pussy dripped at the idea of it. By the time they actually got to the describing of having sex as mother and son, Aileen was three fingers deep in her sopping wet cunt drawing in and out of herself like a madwoman. She climaxed and let out a dramatic moan. It was incredible! She was flabbergasted that the concept had turned her on so.

Aileen had never in her life imagined what it would be like to have an incestuous relationship, or if she did she was repulsed by it, but now she was turned on by it, at least in theory. She assured herself it wasn't like she actually desired an incestuous relationship with her own son; she was just excited by the fantasy of a hypothetical mother/son tryst. There was something about the idea of it that pushed all the right buttons in her. It was just so naughty, but at the same time the trust and security she felt with Ben, that whatever they did would stay between them, made her feel adventurous and extremely aroused. But there was something more to it as well, something she couldn't conceptualize at that moment.

All the while these thoughts were running through her mind, Aileen was casually running her hand over body in the comfortable aftermath of her orgasm. Her hand was lingering over her breasts and playing with her still erect nipples when she heard the lock at the front door click open. She grabbed for her robe in haste and scrambled to cover herself up. She managed to make herself decent enough by the time her son had come through the door and noticed her at the computer.

"Hi, Mom," Colin said.

"Colin, I didn't expect you home so early!" Aileen said as her heart raced from almost being caught in a very unseemly state. Her face felt flushed and she hoped Colin didn't notice if she was blushing.

It didn't look as if he did. Colin shrugged in an indifferent manner and said, "Sheryl said she had some things to do tonight, so I decided to just come home. I guess I could use the opportunity to catch up on some schoolwork."

"That's a good idea. You don't want to get behind now that you're in your senior year." Aileen said trying to sound like she was having a normal conversation.

"True," Colin agreed. "So what have you been up to mom?"

Aileen felt even more flushed than before. "Uhhh... just playing on the computer." She said. Did her voice sound higher than usual? If so, it seemed Colin still hadn't picked up on anything being unusual.

"You and your card games," Colin said laughing. "Since I'm home early, if you feel like playing with a real person I could play a couple hands of something. I know we haven't had much time together lately..."

"No, sweetie, that's all right, I'm fine. School's more important anyway, so you go take care of that. But thank you for the thought."

"I suppose you're right. Well, 'night Ma, in case I don't see you till tomorrow."

"Goodnight, Darling." Aileen said and Colin went off to his room.

Aileen let out a sigh of relief when she heard Colin's door close. Then a potent feeling of guilt racked through her. What would her son think of her if he had known what she had been doing?

She turned back to the computer screen. Ben had tried to instant message her several times wondering what was going on since she went silent. She responded to his queries informing him she was all right, she just had been distracted for a few moments. She told him she needed to take a shower and then would probably turn in for the night. She would be back at another time.

Aileen signed off from the computer and then headed for the bathroom. Once there she turned on the hot water of the shower. She took off her robe and then her panties, when the bathroom started to steam up from the water she stepped into the shower. The nights were starting to get a little bit cold and there had been a chill in the air. Aileen hadn't realized how cold she was until she got under the hot water. It felt so good to feel the warmth seep into her body all the way to her bones.

Aileen replayed the events of the night in her mind while the water beat down on her melting the tension out of her body. How could she have gone along with Ben's scenario, and worse how could she have enjoyed it? Was she perverted? Maybe she was. A couple of months ago she would have thought just having cyber sex was perverted, but now she thought of that as an acceptable thing for two people who were close to each other to do. But pretending to be mother and son... that was taking it too far. She shouldn't have done that and she wouldn't do it again. But even as she made that resolution, another part of her mind drifted back to how it felt, how it felt to be imagining a son so in love with his mother that he desired her sexually. As she thought of this her hands began moving over her body. She massaged her breasts, her nipples were hard again, and she gently pulled and rubbed her fingers over them as water fountained down on her tits.

She imagined how truly devoted a son could be to his mother, the safety, security, and love she must feel knowing what he wanted most was to please her. Aileen's hand found its way to her crotch and began touching it. She discovered her clit protruding and craving to be touched. Aileen condemned herself for being a weak and depraved woman but was too far gone to stop now. She fingered her cunt in a frenzied fashion, her digits repeatedly going in and out lubricated by the shower water and her own juices. Then she turned on the hand held spray and set it to pulsate, she positioned the spray between her legs. The pulsating water hit directly on her clit and Aileen rolled her eyes back in ecstasy. For the second time that evening she had a powerful orgasm.

Clean, dry, and dressed in her nightgown, Aileen lay curled up in bed, but her thoughts were too troubled to sleep. Guilt still plagued her for what she had done. She couldn't get over feeling ashamed that she had done something wrong, but what was worse was the shame she felt for enjoying it. Every time she went over what happened too thoroughly she started feeling horny again, which inevitably brought on more guilt. After going through this cycle for about the hundredth time, she finally felt merciful sleep coming on. One of the final thoughts she remembered before drifting off into a troubled slumber was that maybe talking this over with Ben would help. It was a comforting thought that at least she wasn't alone, that she had someone she could share her concerns with.

The next day Aileen talked to Ben online about the concerns she had.

Bender069: Don't worry about it, we are not doing anything wrong. We are both adults and whatever we talk about or do with each other is no one else's business. If we both get enjoyment out of pretending to be mother and son in a sexual relationship, what harm is it to anyone else as long as it stays between us?

IrishRose36: I suppose you're right.

Ben was really only echoing Aileen's own thoughts when she tried to rationalize what they had done, but it did alleviate some of her guilt seeing him confirm those thoughts.

IrishRose36: But still, I know legally you're an adult but you're only twenty-two. I'm fourteen years older than you, I feel I should be more responsible. Maybe it is wrong to be encouraging you.

Bender069: LOL I assure you, I'm old enough to be responsible for my own actions and I love the fact that you are older than me. I've always found mature women attractive and I used to fantasize about them before I met you. Now your beauty is all I fantasize about. I don't believe a woman can be truly beautiful until she is at least thirty.

Aileen didn't know whether to feel complimented that Ben thought she was beautiful, or insulted that he acknowledged she was over thirty. She supposed that since she brought up their ages, she couldn't really blame him for commenting on it. He had done his best to say he liked that she was older, but it still irked her some that he recognized it. However, with Ben she had found that she couldn't stay even slightly angry with him for long. Talking to him was intoxicating and she soon realized that she wanted to do anything to please him.

Eventually their conversation came back to mother/son role playing. Ben wanted to do more of it, and even though she still felt conscience-stricken about it, she couldn't refuse him and she really couldn't refuse herself. Her biggest concern was would she be hurting Colin in any way by engaging in this activity and she told herself that as long as he never found out about it, it wouldn't hurt him. Aileen and Ben had a secret. She felt guilty and ashamed because of this secret, but also deliciously naughty. It would remain a secret and she would continue to indulge herself because it felt so good.

For the next few weeks they got deeper and deeper into their role playing game and Aileen was astonished at how she hungered for more and more of the fantasy. Ben began directing her to websites that featured erotic incestuous stories. They always focused on the mother and son stories and read them together. The stories aroused Aileen like nothing had before. She became addicted to reading those stories and now that she knew where the sites were that had them she would go and read them even when Ben was not online. There was something about the idea of a mother and son; it didn't seem obscene if they loved each other, their love seemed pure. There was something else about it too, something she couldn't describe, but it made her hunger for these stories. She was hornier than ever and masturbating as often as a teenage boy

Aileen was beginning to think that maybe this was all she needed. She had Ben through the internet and the secret they shared. Maybe that was all the relationship she needed to keep her satisfied. She still had Colin for actual human companionship, and his time actually seemed to be freeing up. Sheryl had a new job at the video store and the hours she worked were different from the hours Colin worked at his part time job, helping out at his Uncle Pat's pub. Colin and Sheryl were seeing less of each other but still managed to go out one weekend night a week, so those were the nights Aileen would spend on the computer with Ben. So Aileen found herself with two young men in her life eager to have her company and she was happier than she had been in a long time.

The last Monday in October was Colin's eighteenth birthday. Aileen threw a big party for him and invited all his friends, family, and Sheryl. It was a wonderful party and she thought Colin was really pleased with it, but Aileen knew that what her son was really itching for was a night out on the town to celebrate this milestone. Colin was a responsible boy, which allowed Aileen to give him a certain amount of freedom, but even though he was now eighteen, she didn't want to give him carte blanche. He still had school in the morning. She made Colin promise to at least wait until Friday to go out partying, and not to get too wild. Colin acquiesced to her wishes with a quirky grin but Aileen trusted him, he wouldn't do anything that would really disappoint her

In addition to it being Colin's first Friday night as an eighteen-year-old, it was also Halloween. Colin was out with Sheryl and Aileen knew he wouldn't be in until late, so she devoted that night to being with Ben. Once she knew the trick-or-treaters were done for the night, she got into some intense mother/son role playing cybering with Ben.

Suddenly, in the middle of the session, right when Aileen was getting the most aroused, Ben stopped typing. It still indicated on the computer that he was online, but he wasn't responding.

IrishRose36: Ben, are you there?

Aileen typed, but there was no answer. Then she typed,

IrishRose36: Ben, are you ok? Please answer me!

Still no answer. She waited for ten minutes and finally she got a reply.

Bender069: Ben won't be talking to you anymore.

Aileen was totally confused.

IrishRose36: What?

Bender069: You heard me you perverted bitch, go find your own fucking man!

IrishRose36: Ben, what's going on? You're scaring me!

Bender069: What are you stupid as well as twisted? This isn't Ben, this is his wife!

Aileen felt her heart fall into her stomach. Was this some cruel Halloween trick?

IrishRose36: Wife? He never told me he was married. I didn't know.

Bender069: We've been married for fifteen years!

IrishRose36: Fifteen years? He told me he was 22!

Bender069: He's 43, now fuck off you home wrecking slut!

Aileen was stunned, she didn't know what to feel. Hurt? Anger? Fear? Despair? Her emotions seemed to be swirling around in a big ball in her stomach fighting for dominance. Aileen rushed to the bathroom where she promptly lost everything she had eaten that day. It felt like she lost everything she had eaten in her life, plus a whole lot more.

After cleaning herself up, Aileen went back to the computer. The last message from Ben's wife was still on the screen staring at her. With tears in her eyes she shut the machine down. She then made her way to her bedroom and shut the door tight. She collapsed onto her bed, buried her face in her pillow, and let out the sobs that had been building up in her. How could she have been so stupid after all that had happened to her? All she ever heard was don't trust anyone you meet on the internet, they could be anybody, and what did she do? She foolishly got involved with a man and believed he was who he said he was. She trusted him, she let him see a side of her that even she was hardly aware of, and he betrayed her. How many times would she have to be betrayed by people she cared about before she finally learned her lesson not to trust anyone? Aileen continued to deliver sobs of anguish into her now soaking wet pillow. She cried until she exhausted herself and finally fell asleep.

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