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Year long affair

I travelled to my sister in law's wedding last year a couple days after my family due to work obligations. When I drove to the wedding, about a 14 hour drive, I wound up driving with a friend of my mother-in-law named Jennifer. Jennifer is closer in age to me than my MIL but they've become very good friends. Jennifer drove with me since her husband wasn't going to be able to come to the wedding due to health reasons. She decided to drive down with me and fly home the day after the wedding. Jennifer and I had always gotten along really well but we'd never flirted and I had never once thought of cheating with her, despite how attractive she is.

As I said, the drive normally takes about 14 hours, we made plans to stop about 9 hours into the drive since there were a bunch of hotels and restaurants in the area we were stopping in. We checked into our hotel, went to our rooms, freshened up and agreed to meet in a half hour. About 10 minutes after I had gotten in my room, there was a knock at the door. I answered and it was her. She had some wine and glasses and said, "Let's have a glass before dinner." I said, "Ok, sounds good." We had the glass and walked to the nearby restaurant. We had a great dinner and a bunch of drinks and were both starting to get a little more free. I knew that if I wanted her, I could have her that night. I didn't think that was the smartest decision even though I wanted it.

We walked back to hotel and went to the rooms. Nothing happened. I jerked off thinking about her and the chance I missed but I knew I made the right decision. the next morning, we woke up, she was very cold and distant with me, which made for a less than fun ride for the morning. We got to the resort where the wedding was and I took her to the cottage she rented. I helped her with her bags and took them inside for her. I realized that the next day we'd be playing golf together so I knew I had to say something. I said, "Jennifer, I don't know what's wrong today, I think I have an idea, but regardless, I am sorry." She said, "No, I'm sorry, you did the right thing." She hugged me and when she did, I lost control and kissed her. I couldn't help it. We stared at each other. Then we kissed each other again and it was better than the first time. She laughed and said, "I've been texting with Robin (my MIL) and told her I'd walk over to their house in 20 minutes. Damn you." I said, "That gives us 15 minutes." She laughed again and said, "we had 8 hours and martinis last night. You would have had the night of your life. Don't worry Hun, we'll get a chance. I'm just glad you're interested."

Our chance came the next day, after golf. We played our round and had drinks with everyone else that played from the wedding party. As people made their plans, it became apparent that everyone in my wife's family, except me, had places to be and things to do. Jennifer, who was sitting next to me, texted me and said, "sounds like someone has plans this afternoon :)" I replied, "Was thinking the same thing." We left the bar near the golf course and I said to my wife, "hey, Jennifer invited me over to hang out since you all are doing stuff. You don't care, do you?" She said, "no, not at all. You should keep her company. I'm sure she's lonely." My poor wife had no clue what was about to happen. So, I showed back up at Jennifer's cottage and she greeted me in just a robe. It was the perfect site. We fucked like crazy that afternoon. I spent 2.5 hours there and the entire time I was inside one of her holes. I left and went to my place, showered and got ready for the night's festivities. The rest of the weekend went off without a hitch. We hooked up one more time that weekend, she gave me a blowjob on Sunday morning when I took her to the airport. Since then, we have hooked up almost once a week and it's been an amazing experience. I am so thankful that my missed opportunity the first night did not cost me.

Next Confession

Turning Into A Closet Sissy

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      • I just love it when they leave their wedding rings on.

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