The Cheating Game 02

Anne: To say I was stunned was an understatement. I could not fathom that kind of love for a woman who cheated on him, not to mention why he went through such an elaborate scheme to get her to think that he cheated. Hell, he could have. She wanted him to. I could not help but feel an intense attraction for this man. Why couldn't I have found a man like this instead of an asshole who left me to raise a child on my own?

I hated his wife more than I had ever hated anyone, including my ex, and I had never even met her. I could tell this was something that hurt him deeply despite the almost joking way he told me his story. His hazel eyes had sparkled when we met and when he talked about his early relationship with his wife but at the cheating part of the story the sparkle went out. I didn't know what this man wanted from me but in that moment I was ready to do anything for him that he asked.

That's when he gave me his proposal. He wanted to "date" me a few times until someone "caught" us together. I would get a free meal or three and some pleasant company while he played his cheating game. Sensing an opportunity to satisfy some of my own urges I asked him how far he would go with a woman and not consider it actually cheating on his wife, something I had realized he was unwilling to do. Would he be naked with her, no touching? Would he watch her masturbate or masturbate in front of her? I explained that I was a single mother who was not interested in dating until my daughter turned eighteen but still a woman with needs, and I explained that I was a voyeur.

"As long as there is no physical contact I could. I've got to be honest, I find you insanely attractive and I wouldn't mind seeing more of you" he replied, "Hell, I wouldn't mind seeing all of you. Is tomorrow night good for you?"

His grin was infectious. I found myself smiling back at him and said yes. Then I gave him my number and told him to text me with the hotel details. With a smile on my face I headed home.

When I told my daughter I had a date tomorrow she told me that it was about time I dated someone. That night I must have cum five times as I masturbated over and over again thinking about our date. The next day I waited anxiously for his text and when I got it rushed to the hotel to meet him. I was so wet I was afraid it would look like I pissed my pants. He met me at the door to his room and as soon as he let me in I said "Let's do this you sexy hunk."

With a smile I started to strip and after a moment he grinned and took off his clothes as well. I leaned back on the bed and started playing with my pussy with my right hand while pinching my nipples with my left. I was on fire and I could tell by the way he was drinking in the sight of me as he stroked his cock that he was turned on too. My fingers were a blur as I watched him. He looked better without his clothes than with them. He was built without being overly muscular, hairy without looking like a bear rug, and had big strong hands stroking a nice sized cock. His eyes devoured me as I jammed three fingers in my cunt and ached to have his hands on me. My first orgasm surprised me how fast it came and how hard it was. My eyes clenched shut and I arched my back trying not to scream as the feeling overwhelmed me. When I looked up he was slumped in the chair opposite the bed, he had cum already. I had missed it!

"No fair" I said but he just grinned.

"It was your fault!" he said through heavy breaths, "How was I supposed to hold out while watching you cum like that? You blew my mind."

We had a drink to calm down and we talked a little more before going again. This time I held off cumming until I got to see him ejaculate all over his chest and stomach which sent me over the edge again. We made plans to go out to dinner and have a repeat masturbation session afterwards one night next week. Then it was time to shower, separately, and go home; me to my daughter and him to his wife. It wasn't till the ride home that I realized that I had better be careful. I could really fall hard for this married man.

Phil: Driving home I was astonished at what we had just done. I had never thought about watching a woman masturbate, much less doing it myself in front of one. What was it about this fiery haired woman that fascinated me so? I found myself looking forward to our next date. This was very different from anything I had done in the past no matter how many "dates" I had been on. I found myself humming a happy tune and when I got home it didn't bother me as much as usual that Elaine was being bitchy. We did not make love that night but I was in a consistently good mood. When we finally did make love two days later she still seemed distant.

Anne and I had dinner and our version of sex once a week for the next month. I found myself thinking about her at the oddest times and we texted constantly whenever I was alone. It was on our next date that I realized just what I had been doing. When we were leaving the hotel restaurant to head upstairs I kissed her. We both froze for a second and with my head spinning I pulled away. What was I doing? Oh my God! I was falling for this woman. This wasn't pretend dating. It was dating. I hadn't even thought about how to let my wife find out because I didn't want her to find out. I didn't want to stop. Anne must have seen the horror on my face because suddenly she looked very sad.

"Just dinner tonight then? I was afraid this would happen. It was too good to be true."

She then turned and walked out to her car. I don't even remember driving home. I called Anne and told her we had to stop seeing each other. I apologized for letting things go that far and that I didn't think I had the willpower to see her again without falling for her and that it would destroy my marriage. I just couldn't be casual with her without wanting more. I could tell she was hurt but she said she understood. I cried when I hung up. I still loved my wife but I had very strong feelings for Anne. I was feeling terrible guilt for what I had done to Anne, because she obviously had feelings for me as well, but also for how I had treated Elaine. I had done something I had never thought possible. Something that in its own way was worse than what Elaine had done to me. She had been sharing her body but I had been sharing my heart. I didn't know what to do but it turned out that I didn't have to do anything. Elaine did it.