After working for a company for 35 years, I was given a generous "package" and since I always liked the work I did in the telecom and computer industry, I stayed within the industry and worked doing small jobs and rarely working as a sub-contractor.
The jobs I enjoyed to most were ones in the medical field where almost all the people were female. Plus, the offices were almost always closed on Saturdays and Sundays so if I had a fair amount of work that required me to run cables through walls or overhead, I knew there would always be a day or two when I would have the entire place to myself.
One office that I had assigned to me was a female dermatologist practice. I think I was in my second week there before I formally met the physician who headed up the practice. I did not form any opinion of her at first but as days went on, I saw that she was quite a fine looking woman. Probably early fifties and she had frequent workouts that she came from or went to. Once a week or so I would see her as she returning or was leaving and her leotards or whatever they are called were very eye-catching. I guess she was a size 8 or 10 and had a fine figure. Narrow waist. Nice set of tits and a spectacular rear end! She was a dirty blonde and she usually had it pulled up in a bun or a clip, allowing her perfect facial features to be seen. She was a real looker!
In the past 10 years I usually vacationed with an old school buddy (a male) or by myself. Depending on if the guy could get time off, I would book the resort (a time share which could be moved anywhere in the Caribbean) and the guy would pay for the car rental, if we needed one. It all evened out.
About 1 month ago my buddy had to cancel and I was a little miffed because he had done that once before. My cell phone conversation was overheard by the pretty middle-aged dermatologist and she inquired "why I was being so harsh with my girlfriend?" I replied that the person I was speaking to was not my girlfriend, only a male friend who has a name that could be mistaken for a female and he had done the same thing a year ago.
The dermatologist took this new information and I could tell there was some pondering going on. The next day was Thursday, her half day and I expected the office to be empty by 1 or 1:30, so I showed up about then. I have a key and security code to a side door and I let myself in. When I am alone I usually set up my radio and listen to music. Today, being Thursday, I had the radio on and some popular country station was playing the current list of popular hits. Florida Georgia Line, Lady Antebellum, Little Big Town.
An hour into my project, the doctor comes in and she asked me if I kept my vacation plan for next week. I had kept it and I told her so. She then floored me when she asked: "Would you mind if I came in place of the buddy who cancelled?"
She mentioned that she had not taken a "real vacation" in about 3 years. I was over-thinking the situation which was stupid. She saw that I was not jumping at the offer and she seemed to be getting ready for a rejection. I told her that if she could get time off and a last-minute plane ticket, I would handle everything else. She asked for flight details and the resort name. I knew she was for real and couldn't control my facial expression.
Within 15 minutes she asked if we should meet at the airport or if we should catch a ride together. Since I was almost on the way to the airport I told her: "Let's share a ride".
The morning for departure came and I had not slept much due to my excitement. Here I was, a 55 year old average dude and I was going to Mexico with a woman who could give any woman a run for the money. At 5:30 A.M. I was outside my house waiting and 5 minutes later a small limo pulled in my driveway. She pops out and said "I am sorry I do not have Mimosas for us to start our trip". Nice ice-breaker!
At check in she mentioned that she had "upgrades" that usually go to waste and if I wanted, we could upgrade to first class if there was room. There were a few seats open and we actually had seats next to each other. I forgot how nice First Class is. Warmed towels, Coffee or drinks in mugs or glasses. The food is still plain, but I was too nervous to eat before I left so it was welcome.
