One also rather interesting conquest was with a lady a few years older than myself. Heather was the laboratory supervisor at one of the factories where I regularly made deliveries.
Now when I say delivery, my particular truck at the time was a bulk food grade liquids tanker, the nature of which required product testing prior to discharge being authorised etc.
The way things worked normally would be for me phone in advance with an ETA so that the factory and also the lab could get prepped for receiving my load. Heather being the lab super had ultimate say as to whether or not the load would be accepted or not. Needless to say being friendly and helpful goes a long way towards smoothing this process....
The factory where Heather worked got regular deliveries late in the day off my rig, thus I would also usually stay overnight in the same town. Nothing ulterior in this, it's just the way things worked most efficiently all round. But it nevertheless became one of the things that Heather would refer to regularly.
After a while I had found out from the guys in the factory that Heather was recently divorced, didn't have any kids, and that she was very keen on Indonesian food....kinda funny 'cause in Gisborne the motel I was staying at had a restaurant that had Indonesian as one of it's specialties. It helped that it was also the only Indonesian restaurant in town....excellent common ground in other words!!
So when Heather started getting more and more flirty I figured it best to go with the flow, occasionally trying to be bashful when she referred to my tight butt as she stood at ground level, watching me climb up the ladder on the tanker to get a sample of the load on board. Being in good shape I had nothing to be ashamed of, enjoying her classy flirting immensely.
In the first instance I didn't really think anything would come of it, but when Heather started playfully patting my bum from time to time I was getting more interested....This tall brunette just had this classy way of carrying herself, yet at the same time she had a playful nature that would come out occasionally....
The touching she was doing got more intense towards the end of summer, me giving her the impetus to give me a bit of a shoulder rub when I complained of a stiff neck and sore shoulders. She just about forced me to sit in a chair and endure a good ten minutes of firm yet sensual rubbing of my neck and shoulders. My cock certainly thought something good was gonna happen from here.
Given that the loads I was delivering would usually be discharged after the majority of the factory staff had gone home, leaving Heather and just one factory worker to look after this process, it often left us to talk and flirt without any else in close proximity. It seemed that Heather enjoyed chatting at the end of the day about this that and the other, when the flirting got serious I just asked her to join me for dinner later that evening.
Her response was rapid and assured: Would love to join you for dinner, the place you normally stay does excellent Indonesian, so yes I would love to join you for dinner. That surely settled things without any doubt.
Now let me just point out that even though I viewed Heather as tall, brunette and classy, her lab coats didn't really give much clue to her body, especially given her habit of wearing them very loose and baggy. There was a sizeable chest hidden in there, and the length of her legs was pretty obvious, but apart from that it was just a mystery....