Where it happened: Southern Oregon
I was from a midwestern state, but had moved West as my wife’s family was in Oregon. After about 4 years my wife filed for a divorce, leaving me a single lonely guy again. I didn’t have any immediate friends that were single and I went to a nearby town which was Medford, Oregon a few times and while there I stopped a time or two at the same restaurant and one of the waitresses caught my eye. Ounce on this particular day it was maybe around 5pm and I ordered a steak. The waitress that I liked said maybe you would like to eat a little later, I took the hint and asked her if she would like to join me for dinner. She said yes, but it would be an hour or so until she got off work. I picked her up after work and we went out for dinner. She was a little older than I was, I am guessing maybe about 38 or 40, I was 31. She was very attractive, and a divorcee, had a nice body. After dinner she wanted to show me the town, by that time it was getting dark, and she directed me to a hill that overlooked the city, which I remember as being a sort of lovers lookout. We began kissing and feeling and it got pretty intense, she had unzipped my jeans and had my cock in her hand and all of a sudden she dropped down in the seat and I felt her warm mouth on my cock. I was totally surprised as noone had ever attempted to do this to me before, and I didn’t know anything about oral sex until that very moment, although I had been married 7 years and had about 3 other women in bed before I met my wife. So I asked her what she was doing, and she replied “this is what you do if you really like someone”. Well, it felt great, and she continued to work on my cock with her mouth until she got me to cum. That was my first time ever for oral sex, and looking back to that event, I still didn’t know that women sometimes like to be pleawured the same way. I spent a few more months with her, and we fucked whenever we could get together, she taught me a lot, she had a daughter about 19 years old who had moved out and had her own apartment, and the girl gave me her address and phone number and asked me to come over sometime, I thought the daughter wanted to know what mommy was getting, so I never did go. We eventually broke up and went different ways, but she was a great teacher and a great fuck and I learned about a blowjob from her, she gave me my first.