This story is about me being almost 19 and still a virgin with women. I had played around but never got home, I was shy and not very sure of myself. I had a couple of friends who didn't know this but always thought they would fix me up, on one occasion my friend who had a steady who was a nurse said his girlfriend had a neighbor who was a little older and needed to go out would I double date with them. I agreed and we set it up.
On the night of the date, he said we were going to the drive in movies, I said ok, and when a car pulled up to pick me up it was him and his girl in the back and an older lady driving. I didn't know it at the time but she was in her 40s but looked a little younger, not a model type but very attractive with a fair body. We introduced and I got in the front seat and off we went to the drive in, not being really sure of myself I took it very slowly. In the rear view mirror I could see my friend get a blow job from his girl. I slowly kissed the woman and she liked and gave tongue.
We made out throughout first movie and when my friend and his girl went to the concession stand we chatted, I told her I was nervous and then sprung it on here that I had never had sex with a woman, she said are you gay, I said no but very shy. She told me that a first time shouldn't be had in the car and she was ok with just fingering and stuff. She told me she would like to get me in bed and take my cherry, I was a little taken aback but she laughed and said I would enjoy it. We set up a date.