I'm having a memory thing concerning my first time. I do remember that it happened and that I ended up with a case of crabs afterwards... kinda like proof. That story won't help me reach my goal of creating as many cums as possible. My second time was much better so here goes...
My home state is full of little towns. At 18, we were too young to go to bars so a typical Friday or Saturday night would be spend driving from town to town just cruising looking for parties and or girls. There was a little town about 30 miles from home whose girls had a bad... or good, depending on your point of view... reputation. My first was with one of these girls in the back seat of my car. They say that there is no such thing as bad sex... just some is better then others but I think I have blocked this one as a bad memory. For the purpose of this story I'll call her Linda... which may even be her real name. I remember that it was pretty common for us to cruise this little town and find Linda out walking the streets. We'd stop and talk for a few minutes and she would get in the car. Sometimes we went cruising or just out into the country, stopping along a country road to party. If we found her one of us could count on getting laid. As I remember, she had her favorite guys... not me. I'm not sure how I ended up with her that particular night but somehow it happened.
A couple weeks later I was out with my best friend at the time who was nicknamed Roach. I've long forgotten the history behind the nickname. It was daytime... probably Saturday afternoon when we saw Linda and a friend walking along the street. We stopped and talked. Linda was about 5'6' and moderately heavy. Her friend, Connie, was about 5'3" with long brown hair, very slim and very cute. The two girls got in the car with us... Linda in front with me... Connie in back with Roach. I remember being kind of jealous as Connie was by far the better looking girl. At the time though I was not going to argue with what promised to be a sure thing.