Straight Male / 53
One Of My Many Cheating Occasions
This is another one of my cheating situations. Happened back in 2006, I was 36 years old at the time. Married with one kid.
I don't want to give too much away, so lets just say my group at work was looking for a product to replace an existing outdated set up. I emailed several companies and asked if they could connect me with one of their reprisentatives. One company responded and offered to fly me to their HQ in Florida for a presentation. I asked my boss if that would be ok with him and he told me it would be better if I went and also took the person who managed the
end users. I reached out to the potential vendor and they agreed to host both of us. So..I would be flying to Florida with a coworker named Janet. A little bit about Janet. She was in her early 60s at the time, but still very attractive. She is about 5'3 and very curvy with big tits. She had been divorced for a long time, 20 plus years.
Janet and I took the same VERY early short flight to Florida. We would be sharing a rental car, and staying one night at the same hotel. We made it to our destination around mid day, and got to our presentation a couple of hours later. All went well, and our host invited us to dinner. We took them up on their offer, but wanted to check in to our hotel first. So we drove there, checked in, and agreed to meet in the lobby an hour later. We met up with the vendor at a nice steak house, had a great dinner and a bunch of drinks. Afterwards, we said goodbye to our hosts and got in the car to drive back to the hotel. On the drive back I could tell that Janet was very tipsy, but up to this point I had zero bad intentions. She mentioned that she had lucked out and gotten upgraded to a suite that had a kitchen and fireplace. I told her I had no such luck and lamented that it's too bad she could only enjoy the room for one night. That's when she suggested that we get a 12 pack and continue the party in her room. My wheels started turning immediately. So I pulled over and got some beer.
When we got to her room, I opened up a couple of beers and put the rest in the fridge. We were in the sitting area when I noticed there was a small stereo on one of the tables. I got up and turned it on to a pop radio station. We were just talking when a song came on
that she liked. She stood up and started to dance. She was looking at me singing and using the beer bottle like a microphone. I smiled, and she reached out her hand. I grabbed it and she immediately pulled me towards her. We started to grind a litte so I turned her around and put my hands on her waist. I think at that point she noticed that my cock was rock hard and she pushed her ass against me and started to rotate her hips. I reached up and cupped her breasts. She tilted her head back, closed her eyes, licked her lips, and put her hands on my hands. I started to kiss her neck ans she immediately turned around for a very passionate kiss. My hands were all over her ass, her arms around my neck so I picked her up and carried her to the bedroom.
I threw her on the bed and got on top her. It didn't take long for her top come off revealing her big tits. I licked her nipples for a while and slowly worked my way down. I licked her lower belly while undoing her pants and pulled them down. To my surprise she wasn't wearing panties. I spread her legs and started licking her hairy pussy. She was moaning and squeezing my head with her thighs. As much as I was enjoying eating her out, I stood up and took my shirt off. Before I could even undo my belt her face was near my pelvis waiting for my cock. She took it in her mouth and gave me a monster blow job. This girl really knew what she was doing. She almost made me cum with just her mouth. Eventually I got on top of her and stuck my dick inside her. She was so wet. Instead of pounding her I went slow and deep. A little while later, I put her on all fours and fucked her from behind. This time I pounded her so hard that she squirted. Her legs were shaking and she collpsed to her side. I moved my dick up to her lips and she took it in her mouth. It didn't take long for me to fill her mouth up with cum. She swallowed the whole load, licked my cock dry.
I spent the night in her room. We got up the next day flew home. A couple of days later we met with our boss to give him a download of our meeting. It was really difficult for me, but she acted like nothing ever happened between us. Same thing going forward, we worked through the implemantaion like proffesionals. Unfortunately, our company was not doing too well financially and less than a year later she was laid off. At her age, she just decided it would be better to retire. I was laid off a couple of years later. I'm still friends with her on FB. Occasionally she will say hello, but not much more than that.
I don't want to give too much away, so lets just say my group at work was looking for a product to replace an existing outdated set up. I emailed several companies and asked if they could connect me with one of their reprisentatives. One company responded and offered to fly me to their HQ in Florida for a presentation. I asked my boss if that would be ok with him and he told me it would be better if I went and also took the person who managed the
end users. I reached out to the potential vendor and they agreed to host both of us. So..I would be flying to Florida with a coworker named Janet. A little bit about Janet. She was in her early 60s at the time, but still very attractive. She is about 5'3 and very curvy with big tits. She had been divorced for a long time, 20 plus years.
Janet and I took the same VERY early short flight to Florida. We would be sharing a rental car, and staying one night at the same hotel. We made it to our destination around mid day, and got to our presentation a couple of hours later. All went well, and our host invited us to dinner. We took them up on their offer, but wanted to check in to our hotel first. So we drove there, checked in, and agreed to meet in the lobby an hour later. We met up with the vendor at a nice steak house, had a great dinner and a bunch of drinks. Afterwards, we said goodbye to our hosts and got in the car to drive back to the hotel. On the drive back I could tell that Janet was very tipsy, but up to this point I had zero bad intentions. She mentioned that she had lucked out and gotten upgraded to a suite that had a kitchen and fireplace. I told her I had no such luck and lamented that it's too bad she could only enjoy the room for one night. That's when she suggested that we get a 12 pack and continue the party in her room. My wheels started turning immediately. So I pulled over and got some beer.
When we got to her room, I opened up a couple of beers and put the rest in the fridge. We were in the sitting area when I noticed there was a small stereo on one of the tables. I got up and turned it on to a pop radio station. We were just talking when a song came on
that she liked. She stood up and started to dance. She was looking at me singing and using the beer bottle like a microphone. I smiled, and she reached out her hand. I grabbed it and she immediately pulled me towards her. We started to grind a litte so I turned her around and put my hands on her waist. I think at that point she noticed that my cock was rock hard and she pushed her ass against me and started to rotate her hips. I reached up and cupped her breasts. She tilted her head back, closed her eyes, licked her lips, and put her hands on my hands. I started to kiss her neck ans she immediately turned around for a very passionate kiss. My hands were all over her ass, her arms around my neck so I picked her up and carried her to the bedroom.
I threw her on the bed and got on top her. It didn't take long for her top come off revealing her big tits. I licked her nipples for a while and slowly worked my way down. I licked her lower belly while undoing her pants and pulled them down. To my surprise she wasn't wearing panties. I spread her legs and started licking her hairy pussy. She was moaning and squeezing my head with her thighs. As much as I was enjoying eating her out, I stood up and took my shirt off. Before I could even undo my belt her face was near my pelvis waiting for my cock. She took it in her mouth and gave me a monster blow job. This girl really knew what she was doing. She almost made me cum with just her mouth. Eventually I got on top of her and stuck my dick inside her. She was so wet. Instead of pounding her I went slow and deep. A little while later, I put her on all fours and fucked her from behind. This time I pounded her so hard that she squirted. Her legs were shaking and she collpsed to her side. I moved my dick up to her lips and she took it in her mouth. It didn't take long for me to fill her mouth up with cum. She swallowed the whole load, licked my cock dry.
I spent the night in her room. We got up the next day flew home. A couple of days later we met with our boss to give him a download of our meeting. It was really difficult for me, but she acted like nothing ever happened between us. Same thing going forward, we worked through the implemantaion like proffesionals. Unfortunately, our company was not doing too well financially and less than a year later she was laid off. At her age, she just decided it would be better to retire. I was laid off a couple of years later. I'm still friends with her on FB. Occasionally she will say hello, but not much more than that.
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