A few months ago, I took a three-week vacation and drove back to Illinois for family visits. Usually, my wife accompanies me on these road trips, but this one she encouraged me to go alone and enjoy myself. As I left and she kissed me, she also winked and told me to have fun. I took that to mean it’s ok if something extra happens and just to enjoy it. During this trip, I was not looking for or expecting to have sex with a...

This true story takes place the summer after I graduated from high school. It involves a girl I graduated with named Hope. I first noticed Hope when I started high school. My high school was a large public high school, but I attended private schools through junior high so, most of my freshmen classmates were new to me. My class had over five hundred students. I noticed Hope the first day of freshmen year. Hope has long bl...

My senior year of high school was a year of sexual awakening for me. This story happened soon after I turned eighteen. It’s about my first time, which was with a beautiful young woman who happens to be a mom. Nowadays, she would be called a MILF. Back then, we didn’t know the term, or certainly, it wasn’t used where I lived. My mom babysat for a few kids to earn extra money. One of the kids she babysat was about three yea...