My boss was a married woman. We were working late one evening when this happened back when I was 22.
My boss was the parts manager at this dealership I was working at back when I was 22 years old. She was married and in her late 30s. She was a very pretty woman and on those days when she'd come to work in her tight fitting pants or short skirt, she'd turn lots of heads.
This one evening we were having to work late finishing up inventory. I had missed a date that evening because of our having to work and I was quite down about this. Ruth (my boss lady) and I was at the store alone. At around 9 pm, we took a break. I went to the break room and laid down on a sofa that was in there. Ruth knew about my missed date and she felt sorry for me but it still didn't help that much. Then, it happened.
Ruth came over to me as I laid on my back on the sofa and she sat down on the edge. She again repeated how sorry she was about us having to work and my missing my date. Then she said 'When Jerry's (her husband's name) is down about something, I have a way of cheering him up real quick'. I just laid there not know anything was coming. About that time, I felt Ruth's hand on my pants right above my genitals. She started rubbing on me there and as all knows what this will do to a man, it certainly did me. I quickly got an erection. Between her hand there and the view I had up Ruth's skirt as she sat on the sofa I was hard as a rock in no time. Ruth then said 'Jerry loves this and I know you will too'.
She stopped and got up telling me 'I'll be right back'. She went into the ladies room and came out with a bottle of hand lotion and a hand full of hand towels. She sat them on the end table and sat back down and continued her caressing my hard penis through my pants. She looked at me and ask 'Feel good'? I said 'Does it ever'. She then undid my belt and button and lowered my zipper. She reached taking my pants on each side and said 'Raise up'. I did and she pulled them down. I was now laying there naked from the waist down with my hard penis pointing straight up towards my head. She got the bottle of lotion and covered her hand with it. She got the towels in her other hand and sat back down by me. She put her lubed hand around my penis and slowly started rubbing it. Her hand felt fantastic and she really knew what she was doing and how to make a man go crazy with the feelings her hand gave. All the while, I was laying there looking up her skirt at her beautiful sexy legs. Before long, I was feeling the strong tingles of my orgasm coming on. Ruth knew it and quickly put the towels under my penis. When my climax hit, I went to squirting shot after shot of cum into the towels. It felt fantastic doing this while in Ruth's hand and in front of Ruth's eyes.
Ruth then proceeded to clean me up of the lotion and cum. I told her 'Thanks Ruth. That felt so good. To tell you the truth, that was the best hand job I've ever had'. I put my pants back on and Ruth and I went back to work. Things went a lot smoother after that.
That was the only time Ruth and I did anything like this. I sure wanted her to but she was a married woman so I never pushed it too hard. I wanted us to go even further next time but it never happened.