My first experience with an older woman happened nearly forty years ago I was a young building surveyor working for a local council in northern England, primarily looking after school buildings. That involved me visiting many of the schools to check on work needed and ensure it was done correctly by the contractors. When the job was a big one, I would spend several weeks visiting and often struck up some good albeit temporary friendships with head teachers or whoever was responsible for the building.
On one occasion I was working with a very attractive head teacher, who I will call Carole, who would probably have been in her forties at the time. To me that was quite old, I was maybe mid-twenties and married at the time. She had short dark hair, wore glasses, small breasts, wide hips, quite a trim body but wore clothes that were probably in keeping for a headmistress and certainly not overtly sexy.
She had a full round arse that was very appealing and had often had me staring as I followed her round. Although I suppose most people would only describe her as average looking, that is what I like, certainly not the perfect Barbie type. As a complete package I found her very attractive and despite the age difference we got on very well; she had a nice personality, a good sense of humour and was very confident.
It would often end up with me staying after school had finished and we would have a cuppa and a chat until it was time to leave. We were often the last ones in the building. I fancied her and had a bit of fantasy thing going on in my head, but that was as far as it went. She was completely unobtainable.
Just being friendly was enough for me and I enjoyed the association. I could lust after her from afar as it were. That is until after maybe three weeks. She started to get more friendly and the conversations got more personal. I didn't realise it at the time but she was checking me out. Turns out I was her fantasy, a young guy up for some fun.
One this occasion I had finished all my work and it was nearly time to leave. We were chatting and laughing and she was very touchy feely, more than usual. She made the point of taking me round the building on her rounds locking up, and when we got to the building's intruder alarm she set it and pointedly told me that no one could enter now without us knowing.
I was quite a quiet reserved person until I got to know someone and, in any case, would never dare to make a move on someone like this. She however, was the opposite, was very confident and she thankfully took charge of the situation. We ended up in her office and I had a feeling something was going to happen. I was nervous in a way but happy to go along with it, never imagining at the time that anything actually would happen.
When we got in her office, she shut the door and came up close and asked me if I fancied her. I blushed but said I did, which was very true. She then told me to kiss her. I was in shock but after a fleeting second went for it. When I didn't move, she grabbed me, pulled me in and kissed me. It took about 3 seconds to turn from surprise to full on passion. It was clear there was a lot of pent up passion going on and she practically devoured me.
My hands were all over her by now, she was quite small up top and I had to get my hands inside her jacket to feel anything. However, her nipples were very hard and I could certainly feel those. She broke off long enough to say that I must never tell anyone about this or she could lose her job. I had no problem telling her I wouldn't as would have lost mine too. This was our secret. She made me sit in a chair and knelt in front of me, unzipped my trousers and proceeded to give me my first ever blow job.
