Best Friend's Sister Sleeping

This happened when I was about 16 or 17 and knew little about masturbation and ejaculation. Sure, I'd had tons of wet dreams by then and my penis became hard at the slightest thought of a girl's breasts, but I had never really whipped it out and went to town over a nudie mag or even the bra and panty section of the Sears catalog. I guess I was ashamed of beating off. Keep this in mind as you read on.
So back to the story....I would usually go over to my buddy's house every Friday night and we'd stay up watching sports or play video games or talk about girls. He had an older sister, about a year or two older than me, who I had never really paid attention to until she hit puberty. Ever since, I would always fawn over her pert, supple breasts and nice round bottom. She was about 5' 5", had a great smile, and blue eyes like ocean water. Every so often we would flirt with each other but it would mostly remain as just little flirts up to that point.
Well, one night I was over, I woke up in the middle of the night to hit the restroom. Now, in order to get to the restroom I had to walk through the living room to get there. As I walked through, I noticed the sister was on the couch asleep. I crept over to her to see how deeply she was asleep. As I walked over, I noticed she was in a long shirt type sleeper made of a thin-ish cotton material. I don't think she even had a blanket on her. My pubescent mind raced seeing this sleeping goddess laying before me. I sat on the carpet next to her and surveyed her body. Being a boob man, I slowly went in an copped a feel of her magnificent breasts. I gave them a light squeeze and ran my finger along her nipples. Given the light material, I was able to make out the skin difference between her areola and the rest of her breast. I then worked my hand down to her pussy but she started to move a bit so I abandoned that attempt so as not to wake her.
I then moved back up to her breasts and massaged them a little more. As I did that, my little head just took over control from my big head and things just spiraled from there. I soon pulled my shorts and underwear down to my ankles and had my raging hard-on out for anyone to see. I leaned over and tried to put my dick on her lips but couldn't quite get a good enough angle to get there without waking her up. Trust me, I tried for a few mins and nothing worked.
Finally, I laid my boner on her arm and put a hand on a tit and slowly thrust my dick back and forth on her milky skin. I did this for a few mins being careful not to wake her. I was in heaven having my way with this sleeping beauty and enjoying the sensation of my skin on hers. Well, as I was taking in those wonderful feelings, I hadn't realized I was slowly building to climax. Again, I was very unfamiliar with masturbation as I never did it and didn't know how long it would take me to reach ejaculation. I was enjoying the moment when all of a sudden a saw burst of white glow in the darkened room and land on her face. I quickly became mortified as I saw her face scrunch up from the impact of my jizz. I then shot another small spurt on her shirt. I quickly ran towards my friends room all the while spurting out more ejaculate. I made my way back into my friend's room and laid back down. He was still asleep.
The next day, I woke up and his sister didn't say anything or act different. It never came up in any conversation. As far as I know, she might have stayed asleep. I don't know if she thought it was a dream or what. I don't know how she would explain the cum spots. Either way, it was one of my first of many sexual experiences with her. Maybe I'll divulge more later.

By Anonymous

Masturbation CONFESSION

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