Guided Masturbation Stories


My Sister and Her Friend

from the Net, date unknown
 

 

I clearly remember the first time I masturbated. I was on an outing with my family at a lake in the northeast US. I was 10 or 11 at the time and my sister, Karen, was 16. Initially I was very upset that my friend could not come along. After all, Karen had her friend along and I was all alone. I guess I whined enough that my mother instructed my sister to let me tag along with them during the day. Karen, as i said, was 16 and blonde. I had noticed that she was the center of attention of my friends and I always liked to look at her. Her friend, Denise, had black hair and hug knockers.

All day long I noticed them laughing and giggling and whispering at each other. I did not think much about it (girls always did stupid stuff like that) except I got the weird feeling they were giggling about me. Denise especially kept on looking at me when I was in the water. I sort of liked it and sort of thought it was spooky. Anyway, after a day of picnic and swimming and boating in the lake my Karen and Denise decided to take a walk in the woods. I begged to go on the walk (anything than being with the grownups - how boring!)and whined enough that they finally consented.

We walked into the woods and up a slight hill for 30 minutes or so. Karen and Denise in front and me trying to keep up. As soon as we were out of earshot of my parents Karen started ordering me about ('You are too slow, Hurry up', etc.) She started calling me a little wienie. Denise kept on looking at me and wanting to walk behind me on the trail. It didn't take long before she was bossing me about too and making fun of me. Both of them were. When they did that it made me nervous but it excited me at the same time.

Finally we reached an open meadow and field that was planted in short grass. We walked out of the woods into the late afternoon sunlight. As we walked on we found an outhouse and Karen said she had to pee. I did too and was sorely tempted to hold my dick but Denise was there and I would have been embarrassed to do so. So Denise and I waited outside while Karen. All of a sudden Denise smiled at me and looked like she wanted to say something to me. Right then Karen emerged and Denise insisted that it was my turn. I was glad that it was and I went in and pulled my zipper down and took my dick out and peed and it felt REALLY good. As I was peeing I happened to glance over to my right and I saw an eye staring at me through a knot hole in the wood. It was Denise!!

I was shocked but very excited by being spied upon. I was visibly shaking as I came out of the outhouse, not knowing what to do or say. I looked at Karen and Denise but neither of them said a word as we walked on towards the woods. I wanted to say SOMETHING about what had happened when Karen suddenly stopped and turned and looked at me and said "Now listen you little worm, you will do exactly as I tell you to do and you want tell anyone". She had such fire in her eyes and I had never seen her so determined. All I could do was stumble for words when suddenly Denise came up between Karen and I and said "No One!" as her hand went to my crotch. I moved back, shocked and confused by what happened. Karen reappeared in front of Denise and grabbed my belt. She held me as Denise pulled my hands behind my back. My heart was pounding so hard and fast that what was happening was like a dream. Karen then looked me in the eye and said "You will do what I say you little worm or I will tell Mom and Dad that you masturbate" I wasn't really sure what "masturbate" was but i knew it was bad.

Then something happened that I will never forget. Karen unbuckled my pants and, before I knew it, pulled them down to the ground. I looked down and was amazed. She grabbed my cock and it started to get hard. i felt light headed as the blood rushed to my rising cock. Karen moved back momentarily and said "Shit" as they both stared at my rock hard cock, right therein front of them. "Fuck, its so big" I heard Denise say. I had never heard either of them talk this way before and I was in shock but terribly excited and I didn't want it to stop.

"Touch it" Denise said. "Huh" was all I could say. "You stupid!, touch it!". I was terribly embarrassed and hesitated until Karen said "Now you worm!" Denise released my right hand and Karen grabbed it and pulled my arm around in front of me. "Come on" she said "I've seen you playing with it, DO IT" (Oh My God, I thought). I reached around and touched my penis. "Stroke it!" Denise said. I started to stroke it and it felt so good. My balls were tight and I was more excited than I had ever been (little did I know that there was more to come). Somehow it was so exciting to be doing this in front of Karen and Denise. I was trembling with excitement and my cock was harder and bigger that it ever had been. Neither of them could take their eyes off of it and that made me feel real good.

"Do it, do it" Karen said and to my utter amazement she put her hand down her shorts and the next thing I knew they were on the ground. There was her pussy right in front of me and she was furiously rubbing it and moaning. I closed my eyes afraid that I would black out and when I opened them both Denise and Karen were masturbating right in front of me! They were staring at my cock all the time. Denise kept on moaning and saying "Shit" over and over. I stroked my cock harder and faster as I heard Denise moan loudly as she came (I later understood). She then walked over and grabbed my balls and said "Make it cum worm!!" I looked at Karen and she had one hand on her pussy and another under her top feeling her tit. Suddenly she screamed with orgasm and as she did I shot my cum in great gobs all over her, Denise and the ground.

We then clean up and walked back to our picnic like nothing had happened. But there were to be many other times. It was the most erotic thing that has ever happened to me.