The Craziest Weeend

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.

Continuing my assault on her back, I would stretch out her arms behind her so I could see her perfect breasts, which I just wanted to grab, but knew I couldn’t.

After a while, my sister turned to me and said “That was awesome, but it’s time for bed” and I knew the night was over. I played with my self after I knew she had gone to sleep in the bed next to her.

The next day was a beach day when I saw Michelle in this perfect black bikini. More dirty thoughts. Still nothing I could do, I thought. After dinner, My sister and I went out on the town together. We went out drinking on a credit card my dad had lent me to help pay for dinner, so by 10:30, we were already pretty buzzed.

We walked by some beach bar with a live band in it and she grabbed my hand.

“Let’s go in. Since I’ve been in school, I haven’t seen any live music at all.” Why not, I thought so we headed inside. More tequila shots. “Come dance with me. So many of these guys are creeping me out”. So onto the dance floor, which was more or less a tight group of people congregating around the stage. She led the way holding my hand, and we fell into the crowd Michelle in front of me and me right pressed up against her ass. I had my hand on her hip and she held it still. As she was dancing in place, her ass was rubbing all over my dick and I was hard as a rock. There was no way to even hide it at this point. Finally I couldn’t take it anymore. I moved my hand, still with her’s over it, up along her flat stomach and touched her breast for the first time in my life. She did nothing to stop me, so after a while I went under her shirt and under her bra and slowly kneaded her right breast. It was, up to that point, the most erotic thing that has ever happened to me. I was feeling up my older sister and she wasn’t stopping me. It was heaven. This went on as my head was spinning. I couldn’t help myself so my hand then went down her black miniskirt and into her g-string. Her pubic hair was soft and moist. She immediately took my hand off her and looked at me sternly.

“What are you doing?”

“I’m sorry. I just got carried away”.

“Yes, you did” was all she said as she walked out.

We walked back to the hotel in silent and both got ready for bed without ever saying a word to each other.

“So I’m curious” she asked, “How far were you planning on taking that?”

“I don’t know. Nothing. It just felt good. I’m sorry” was all I could say.

Another half hour passed with both of us in bed but neither of us sleeping.

I went up to go to the bathroom and was headed back to my bed when she stopped me and touched my arm. I sat on her bed and apologized again. “Shhh” she said and started to touch my leg. She pulled my dick out of my boxers and started stroking it. “This was what you wanted, right?” and then those huge lips took me in her mouth. It was perfection. I exploded into her mouth and she swallowed me. “Better?” she asked and I said yes. I got into bed with her and snuggled her perfect body. She didn’t stop me as my hands explored every inch of her body. I took off her top and bottoms and just rubbed her as we spooned.

She started moaning as I played with her clit. I sucked on her breast and started to feel myself getting hard again against her naked ass. She started rubbing herself and I started stroking myself against her asshole, up and down the length of her crack.

“This is so wrong. We are being so bad” she said but didn’t stop.

I could feel her wetness and rubbed myself over her puss and then back to her ass. I figured I might as well go for it, so I pushed in against her anal ring. The tip just popped inside.

“Ouch” she said but didn’t make me stop. “That hurts a little”, but I still didn’t take it out. She continued rubbing her clit and I was stroking myself with just the tip of my cock up her ass.

“I want it deeper. Don’t stop” she whispered. The lotion was still next to me from last night’s backrub, so I lubed myself up and pushed more inside her, about half way now. “That feels so good” she told me. I finally pushed myself until I was fully up her ass as we were spooning. My motion was now in and out. This was the most incredible feeling ever. I felt her come and her ass tighten. No more movement until she relaxed because I was being held by her tiny little asshole. I unloaded my second come of the night deep up my beautiful sister’s little asshole. So amazing. So nasty. So incredible.

She looked over at me as she took me out of her and said goodnight. Where was this going to go?