Joining Adult Matchmaker (and being a little naive), I started messaging ladies from the site until one replied back. At the time she was probably a few years older than me. After much to and froing... messaging and arranging to meet we finally worked out a time and place to meet for a drink and a bite to eat. I wasn't sure what to expect, but as we had swapped phone numbers I though it should be ok. I was sitting at a table waiting for her when she arrived... slightly on the chubby side but not overweight and a black mid length dress that sparkled a little. I got up and we exchanged pleasantries, a kiss on the cheek and then ordered coffees (was about 7 pm so a bit late for a coffee, but anyway), we chatted and were getting along famously, laughing and just enjoying the evening. Out of the blue she moved in close and whispered in my ear that she wasn't wearing any panties and could feel she was getting a little damp down there, so I paid the bill and we left. Once outside I asked what we should do or if she wanted to continue. I suggested a motel room and she agreed. All good and she followed me in her car and I went in got the room and got the card while she stayed in her car. I walked out of the office and up the stairs to the room and had sex... nothing special just normal sex even though she was totally aroused and right into it. After the night was over we went our separate ways. I can’t exactly remember her name but I think it was June or Joan.

June calls me up the next week and asks if I would like to meet her near her work at Parramatta... I agree and following her instructions park on the street and she comes out and directs me into a car park where her car is parked (by this stage its already dark with not a lot of cars in the car park and we are reasonably high up and she tells me where to park near her car... we are overlooking the office buildings across the street. We are just talking about things and she slides her panties off and we start making out... I feel her pussy and she is so wet. We decide to get into the back seat of my car and she ends up sitting on my lap... moving around a bit she hikes up her skirt and guides me to her ass... slowing taking more in... I feel the knob of my cock enter her arse and go all the way down... so tight and she is loving it... I move my finger and enter her pussy and can feel my cock in her arse through my pussy and she is dripping wet... we both cum and have to take a few minutes to unwind and she says, see that office over there... That’s my office where I work. We had many more adventures after that but had to stop when her son in law found out what she gets up to by finding a big dildo in her bedroom... what was he doing snooping around in there... anyway i was on the outer and I think I was replaced by the son in law...