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.
We headed out of town and drove for awhile... drinking as we went. Colt 45 in 16 oz cans was a typical for us. There was also a lot of touchy feely going on. As I said we were young... under 21... so were very limited on where we dared be. A favorite place was what we called haunted houses. They were actually just abandoned, but being kids, we let the imagination flow. On this particular day, I think one of the girls directed us to a particular house.
We went in carrying a couple blankets with us. Somehow, Connie let it be known that she wanted to be with me so we switched girls. At the time nobody was in love and at least we guys were very horny so didn't care... anything to make the girls happy. Connie and I laid a blanket on the floor in one room and promptly sank on it kissing up a storm. Roach and Linda went into the next room and did the same on the couch. I remember playing with Connie's breasts under her shirt as we kissed. I was always full of apprehension waiting for the dreaded "Stop... that's far enough". I did know enough to understand that the hotter I got her, the less chance I would hear that phrase, so I did play with her a lot, letting her guide me to the next step.