Fun by the pool [f]

This is my first post so i apologize if it doesn’t fit the sub or if there are formatting issues. If you like it let me know and I will post the rest!

This all started several years ago. My friends and I had recently started hanging out with a new group of guys, even more recently I started casually dating (read hooking up) with one of these guys, let’s call him Brad. Brad was very sweet and quite a bit more experienced than I was. Before Brad i had only ever really made out with a guy before not much more. Being with Brad even just casually gave me much more confidence than I had ever had in my life than I had ever had before which leads us to the start of the story.