Jimmy’s Sister Harem

Jimmy’s first day as an 18 year old had been a weird one. He had lived his whole life on a remote villa. His parents were billionaire real estate investors who decided to retire. Elsewhere. He was the youngest of four siblings. His oldest sister Laura, 28, was the most outgoing of the bunch. His sister Caitie, 25, was a follower, particularly of Laura. Finally Sydney, 23, the most shy and reserved of the bunch. Their parents had surprised them with the news, and left that day. Jimmy and his siblings had only ever lived there, with almost no exposure to the outside world. Their groceries were even brought in by drone!

They had little exposure of outsiders, and Jimmy get that they all kind of decided to get on with their very comfortable life there. The situation was kind of awkward for the first two weeks as Caitie and Laura’s demeanor changed right away. They giggled a lot around Jimmy and Laura especially seemed to be making weird overtures towards him. Sydney staid almost entirely in her room. Jimmy did too, he liked to play video games alone in his room, while his sisters played by the pool or around the house.

Puberty had been awkward around the house, Jimmy had some awkward situations with his sisters and boners, but nothing too crazy. Jimmy mostly just watched porn alone in his room. Today was no different, or so he thought. Jimmy was alone, as usual, and pulled up a video, ‘butt sluts get wild’. Jimmy had pulled his dick from his pants and began touching it. Suddenly his sister, Laura stormed into the room. Jimmy stuffed his dick into his shorts and downsized the screen. “What the fuck Laura!” He exclaimed in frustration and embarrassment. “Can’t you knock?”

Laura had a knowing smile on her face. “Um…no. I know what you’re doing in here. You’re beating your dick like the little pervert you are. While I’ve watched porn too, I’ve never seen the real thing, so I wanted to try.” She was wearing tight running shorts and a white tank top, and bent over exposing her cleavage. “So I figured I’d come in here and help you out!” She pulled up a chair next to Jimmy and sat down uninvited. “I d-don’t think that’s a good idea!” Jimmy stuttered. Laura didn’t wait for permission. She grabbed the mouse and reopened the video and pressed play. “Don’t worry about it, you don’t have to do anything. All you do is watch the video or look at me! I’ll take care of the rest.” She said leaning in alluringly.