It all started about a year ago. My wife Lynn and I were on vacation in Puerto Rico, and stayed at a wonderful four-star resort. We had a fantastic dinner one evening, and adjourned to the adjacent library/lounge for a few after-dinner cocktails. She had a few snifters of Amaretto, I had a few B&B's and a great Cuban cigar, and we just hung out and chatted with a bunch of other vacationers. In short, one guy in particular was obviously gravitating towards Lynn. I think she appreciated the attention, and it made me feel good as well, knowing other men found her attractive. I asked her to join me at the bar, and as we had a few moments of privacy I asked if she would like to have a little fun with him. Lynn told me that if it would finally make me shut up and stop asking, then she would grope him a little, just this once. Just grope, no sex, and I shut up. Understood. Deal.
My heart pounded as I shot a little pool with our friend. Not knowing how to start the subject, I came right out and asked him if he would like Lynn to get him off. He was of course surprised, but agreed readily. I let him know before hand that there wouldn't be sex, just a little masturbation, and if he could handle that then great. He had no complaints.
After the game we both went over to Lynn, and I told her we were ready. She told me she hopes I enjoy this, and took both our hands. We went to his room, and in a no-nonsense way Lynn tells him to take off his pants and lie on the bed. He drops his pants and lies down on the bed and she lies down next to him on her side, throws one leg over his, grabs his cock, and starts stroking it. I didn't have a chance to prepare, it happened so quick it was like I was watching a movie. She began kissing his mouth and stoking his cock at the same time. I watched his hand move under her dress, and saw her head tilt back with lust when he found her pussy. She gently drew his hand out from under her skirt, as if the pleasure he created was not in the script. She led his hand to her breasts, where he massaged them through her dress. He came in a few short moments, my wife pulling harder as he climaxed. Her face hidden by her long hair, she went down to his cock for only a second, and I found out later that she gave him a nice kiss on the tip. She stood up, kissed our host, walked over to me, kissed me, and asked how I liked that. I didn't answer but took her hand and led her back to our room for an evening of passion.
That encounter has been re-lived every time we had sex for the next 12 months. Although she had pretended to be aloof about the hand-job, she was always much hotter during sex when I asked her about it. How did his cock feel? Was it nice to stoke another guy? Did you want him inside you? I went so far as to purchase a very realistic dildo and make her stoke it, telling me how it felt. She seemed to be buying into my fantasy, and telling me how hard it felt and how nice it would feel inside her. The ultimate outcome was wonderful sex for the next 12 months.
That's the history, so here is where my story begins. Last week my company sent me on an overnight business trip to Boston. It was a meeting that lasted all day, so instead of making the 5-hour drive home that evening, they put me up for the night. Of course, I asked Lynn to keep me company on the drive, go to a spa while I was in meetings, and then we would spend the night having some fun.
During the trip to Boston we had some time to talk. We both knew her encounter last year had dominated my fantasies since then. I proposed that I could handle her doing it again, this time with maybe a little oral sex. Perhaps I should even let her go all the way, but in truth I am a jealous person, and could one day see myself letting that happen, but not yet. Maybe just an evening of watching her flirt with guys would get me all charged up, and she was up for the challenge. The plan was to meet in the hotel bar at 8pm and sit at opposite ends. We would both have a few drinks and eye each other, and I would let her flirt with a few guys. She would tell anyone she talked to that she was married and traveling on business, as the excuse would provide an out should she want it. The encounter would be fun to watch, and there would be no pressure, as she would play it by ear.
I arrived at the bar late, she was already there in a black, knee length dress, a few guys sitting adjacent to her. I walked by, brushing up against her without a word, and proceeded to the other side of the bar.