The next day I was sitting on the lifeguard stand when Amy came up to me, looking around to make sure no one was listening. “Hi Amy. Tomorrow’s your big date with Connor. Are you ready?” “Um, that’s what I wanted to talk to you about. My older sister is friends with a girl Connor used to date. She says he likes anal sex. What should I do?” “You don’t have to do anything you don’t want to, Amy, particularly on the first da...

The summer after I graduated from college, I took a job as a lifeguard at a private club in the small Midwest town where I was raised. I needed to make a little extra cash before I entered law school. My girlfriend was off in Europe. I figured it would be a long fuckless dry spell with the only action coming from Rosie Palm and her five sisters. Boy was I wrong. A group of high school kids who worked at a youth camp often...

The next afternoon I heard a knock on my door. I peeked out the window and saw Emily with her friend Amy. I wondered why they were here, particularly after yesterday. Emily had given me a blowjob, her first, and I had fingered her pussy. Was she back for more, and if so, why was Amy with her? I opened the door. “We need your help,” Emily said. “Can we come in?” I gestured them inside. Amy smiled at me as she passed. Like...