This is the first time I have really ever written or told anybody about the craziest weekend of my life when I slept with my older sister. It’s so crazy how these things happen in life. I might as well start from the very beginning....
My older sister Michelle is 3 years older than me. We grew up together in your average household (professional happy middle class parents) in a hillside house on the outskirts of San Diego. I went to a boys school for most of my life, which was not a problem until I hit puberty. Our “sister” school did not have much interaction with us, so I resorted to endless masturbation growing up with playboys and your occasional late night cable movie.
A lot changed when I started to notice Michelle in that special new way only an adolescent male can ever describe. She’s 5’5” with long curly dark blonde hair, huge blue eyes and the fullest lips. Fit, but with D cut breasts and a cute ass. Her body is actually incredibly similar to a Britney Spears more than the lanky model type, which I’ve always preferred. Since she didn’t really see me as any threat, she wouldn’t mind if I hung out in the bathroom when she showered cause you couldn’t see through the glass. I saw just the dark pubic hair and pinkish nipples which would always leave me beating off while talking to her in the shower. Later I discovered that I could see through her window at night; it became like a one way mirror after dark, so I’d spend countless hours out there watching her. The two best moments through those high school years was the first time I saw her masturbate and her giving her boyfriend at the time a sloppy, perfect blow job.
Fast forward to last year and that one weekend. I was 23, she 26. We had gone with my parents for a vacation to Hawaii. Although I felt a little old to be still traveling with the family, I couldn’t pass up the opportunity. My girlfriend at the time stayed back home. Michelle and I were going to share a room which sounded fine to me. It had been some time since we’ve seen each other cause she was in graduate school in Florida. Maybe I could catch a glimpse of her naked again or something. If not, no big deal.
We got in late on a Friday night and went out for a little while, but were pretty tired so headed to bed fairly early.
Before turning out the lights, Michelle looked up at me with those huge eyes while she was rubbing her neck.
“Ben, would you mind giving me a massage on my neck. It’s cramped up pretty bad”.
How could I say no? I started to rub her neck, but it became apparent that I needed lotion so went to the bathroom to get some hotel stuff. She took off her shirt, leaving her in a bra and panties and got on her stomach. It wasn’t that big a deal; we had seen each other like this many times. I started to rub it all over her back, but her bra strap was constantly in the way. By this point, I was horny as hell but knew that nothing would happen.
“I’m going to just unstrap this, but you can leave it on” I told her.
