I was 37 years old and had only tried to make out with a female once in my life and it wasn't a very good experience, which was probably because neither of us had done anything like it before.
I decided to place an ad on craigslist and after receiving several responses, I finally received an email from Rachel that sounded as if she was the type of woman I was looking for. We exchanged text messages for a couple of days and Rachel asked for a picture of my breast which are a size 38DD. I sent her a picture and she sent me a picture also with a message that read "I wanted to lick my phone when I saw your pic." We spoke on the phone for several hours that day and finally decided we would meet later in the day. We agreed to attend the fair which was in town as it was every November. During the latter part of the conversation Rachel asked me if she were to make a pass at me would I ask her to stop, and replied that I would not. I surprised myself with my answer since no female had ever made a sexual advance toward me, but for some reason she had made me feel comfortable with her even though we hadn't met.
We agreed to meet at 6pm and she texted her address to me. I showered and dressed comfortably in blue jeans and a blouse with a black bra and black bikini trimmed in red. When I arrived at Rachel's home I called her to let her know that I was outside.
We had a great time walking around the fair, as we talked as if we had known each for years. We talked about our jobs and family for hours until we decided we had walked enough. After the fair we arrived back to Rachel's and sat in the car and talked. Rachel asked if I would like to come in, to which I quickly agreed.
As we were walking to the house I was wondering what I had gotten myself into. Those feeling were intensified as I sat on one end of the couch and Rachel sat right next to me. While we were talking and watching TV, Rachel began caressing my arm, which was stirring all kinds of feelings. As my breathing became harder she asked if I was nervous which I replied no, I was too turned on to be nervous. After a few more minutes of her caressing my arm she leaned over and began kissing my neck.