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My 1st Memories Of Masturbation

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Events and memories leading up to masturbating to orgasm for the 1st time. Replies to any of my stories would be welcome.


This is a great site. I love that the ladies chime in with their experiences, too. I feel, that for a man, it's alwasys helpful to look at sexual experiences from a girl's point of view. It makes me a better lover.
I have written here before, recently telling you about the last time I had a baby-sitter, at the old age of 12. I guess I could have written this story 1st, as it was the 1st days of masturbation for me. But, the other story was completed 1st.
So, it was just before starting the 6th grade in Jr. high. Now they call them middle schools, but where I grew up, the Jr. high was grades 6, 7, and 8. I remember that's when I became interested in the opposite sex. Girls didn't get my attention before that. Well, not really. I was always shy with girls, but I've always been in love with a pretty face. Even in grade school. I just fell in love from a long distance, but it never filtered down to my loins until something inside of me said it was time to think of the other parts of a girl than just a pretty face.
I remember when school started that year. It was a new school with new expectations. Of course, it was a more mature setting than grade school. And, there was an exciting fear of the unfamiliar. There were new schoolmates, more demanding teachers, a whole new culture. And, boy-girl relationships becoming more apparent in the halls between classes, though that was much more with 7th and 8th graders then.
And, there were MUCH more pretty faces to dream about. I started noticing the bodies more, as most of the girls were starting to bud like flowers in 6th grade. I started having strange fantasies about some of them. I remember one, Peggy. She was so sweet looking. And, she was so nice, too. I could barely muster the courage to talk to her. I'll bet in the 2 years I knew her in Jr. high, I only spoke 10 words to her, even though we shared the same classes for both years. I'm sorry to say that she moved away before 8th grade started, so I never had a chance to get to know her when my shyness slowly faded after Jr. high.
She had a real petite body in comparison to the other girls. But, she was so huggable, with a pretty smile always on her face. I used to imagine what her breasts looked like. I KNOW she had them, though not so noticeable unless she wore this certain type of shirt. I could see the form of her sexy bumps through this one shirt she wore. And, they jiggled like a bowl of Jell-O when she walked. She was one of the few girls that didn't wear a training bra, I guess. And, thinking of that always deepened my infatuation for her.
Her hair was a modern style for then, dark and framing her pretty, pale, slightly freckled face. Her eyes were dreamy. She melted my heart as I sat in silence each day... looking at her. It's a wonder I passed any of the classes, for all the dreaming I did about her. Though I played sports, basketball wasn't one I played well until high school. Good thing, too. Peggy was a cheerleader for basketball, and she would have been too much of a distraction for me. I went to games, but not to see the game. I loved seeing her jump, and twirl her skirt. Seeing her down there with her excited smile turned me into a bowl of mush.
I remember sitting in class, and getting some of my 1st erections that year. Thinking of these strange thoughts of all the pretty girls I saw. There was little I could do about it, either. My hormones were getting deliciously out of control. Many times, the bell would ring, and I'd sit there until all had left the class, trying to get my boner to go down.
But, there was still little connection in my brain yet between the lust I felt, and the magical things my penis would do. Getting a boner had little to do with the things going on in my head. I never engaged in talk of sex with my friends. We talked only of sports. Boners would just happen. But, alone, I started to think of other things. My mind would run amuck in fantasies of love. Not sex. But of being with someone like Peggy. Having conversations with her. Holding her hand. Even kissing her sweet face.
One night, as I drifted off to sleep, in one of those controlled dreams you have, as you're half asleep and half awake. I thought of all the pretty girls I wanted to know. And, what did they look like naked? Hummm. I thought of hiding in the girl's shower after gym, and looking at all the naked bodies in there. Not having sex with them. But, solving the mysteries of childhood. What's under there? I have no sisters, so there were no accidental discoveries. No, my view of girls then was of a truly mystical sense. Sure, I knew what a breast looked like. But, they were all so different. And, I had never seen one in person.
So, in my controlled dream, I lined them up, side-by-side, and naked. Peggy, Susan, Linda, Lou-Ann, the twins Cheryl & Carol, Rhonda, Nancy, Barbara, Keri, Kim, ....... the lineup always changed. Different girls to get naked for me, and let me look... and NOT laugh at me. That was important. But, Peggy was always the 1st to be called. What a smile!
But, believe it or not, these nightly fantasies did not directly lead to my 1st experience with masturbation. Oh, I'm sure I got into rubbing down there then. But, I don't remember having orgasms alone in bed until later on. No, the 1st time I actually masturbated, and had an orgasm was when I was watching TV. I remember there was a stupid movie. A musical with Ann-Margaret in one of her 1st films. She was so beautiful, and sexy, and perky. And, well, she was about 20 in this movie. I was mesmerized by her charm. She danced in those skintight leotards, and DAMN, those sweaters she wore. That smile! And, her sexy voice. Hearing her voice always melted my heart. In the movie, she was singing a number, and changing her clothes from some knock around jeans and shirt, to something more feminine to go to some party. She danced and sang back and forth from behind this screen they always put up in movies when the character is changing clothes. Kind of silly, isn't it? Having a screen up in your own room to change behind.
But, something is happening down below. What's going on? I'm on my stomach on the couch as I usually was when I watched TV then. But, .. damn, something sure feels good down there. I'm in the basement alone. I look around to make sure. Everyone who's home is upstairs. Something clicks in my head. I see the silk pillow at the end of the couch. That looks smooth. I put it under me, pull down my bottoms, along with my underwear, and I mount this pillow and hump. And hump, and hump some more. It felt soooo good. She's takes her sweatshirt, and throws it over the screen as she keeps singing. She's teasing me. Her red hair is flowing all over. My adolescent cock is coming alive. It's hard as a rock. And I feel this very strange feeling a I keep humping the pillow. I feel this gush of excitement shoot through me, and out of my cock.
I remember thinking the other day. How did it feel? Did having an orgasm feel the same then as now? Nope. As I thought about it, I caught the remembrance of that feeling back then... just for a brief moment. It was like an internal itch. And, I never thought about controlling it. I just humped a pillow until I came. Then, I'd clean it up with a tissue. And, then, I'm sure, I felt guilty about it. Often I would hump it again before going to bed. The stock of Kleenex must have doubled during this period of my life, because it would take lots of tissues to clean up all the cum that spurted from my cock. Later on, I learned to use wash cloths.
But, I made the connection. My dick erupts when I see naked girls. I get this indescribable feeling when I thought of a girl in this new way. It was great. However, this made things worse at school. All class long. Boners. But, at night, I would hump the pillow. Poor pillow. I wonder what ever happened to it. I can still remember as I humped the pillow, raising myself up with my arms, and seeing cum spurting out of my cock all over that pillow. It was fascinating to see that sticky, thick white stuff squirt out of my pee hole. Not all at once. 1st a small spurt. Then a longer spurt. Then another and another. Often, the cum shot past the pillow, and onto the couch. Then it just oozes out, my cock head smeared with cum. It was so beautiful to look at.
Actually, I didn't learn to use my hands to masturbate until a few months later. My friend, Phillip and I were talking about the girls at school. Talk got around to jacking off, but I didn't know what that was. He told me he would look at the pictures in the Playboy magazines his dad had. I told him about humping a pillow. I didn't have the heart to tell him it was the very pillow he was throwing up in the air and playing with while we were talking. I guess he assumed I was talking about my pillow in bed. He told me about pumping his cock when he had a boner, and that's how he got the stuff to spurt out. I tried it later, and it was good. But I still liked my pillow to hump. I also humped my pillow in bed, but that silk pillow was my favorite.
So, that's the 1st time I masturbated to orgasm. Not dreaming about Peggy. Or any of the other girls that made me smitten with puppy love. No, it was my 1st movie star fantasy, Ann-Margaret.
This was the mid 60's, so I loved to hump that pillow watching TV when I was alone. Not just looking at girls on TV who were pretty, but those also having sexy and charming personalities. Girls like Marilyn Monroe, Mary Tyler Moore, Mary Ann from Gilligan's Island (I hated the show but watched just to drool over her), and Barbara Eden... and others. And, soon enough, I'm making love to my pillow thinking of my 1st love... Peggy. And, she never knew. Except in my dreams. Funny, but then, I never masturbated thinking of having sex with Peggy. Just seeing her, and fantasizing about her cute face and body. But, the fantasy mind has to grow, too, right?
Thanks for reading my story.
Fantasy Man



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