Almost... A Few Times

When I was born, my father was fifty and my mother was thirty-eight. I was the only child. I did have many friends in the neighborhood, but not a word was ever spoken about jerking off in all the years I spent there. Neither parent spoke to me regarding sex. My two best friends, George and Fred, both had older brothers, three and six years older than we were. These older brothers must have told their siblings something; but they never passed the word to me. By age twelve, I had a hardon every time the class stood up to sing the National Anthem in the morning. At age thirteen, my mature female cousin, about my age, came into the den as her parents were visiting mine in the living room in the front of the house. I vividly remember her saying to me as I was standing behind my father's desk, "You know, you're a good looking guy. Wanna have some fun?" as she began to unbutton her blouse while looking at me seductively, eye to eye. I said, "What do ya mean?", as I stuttered and nervously walked out of the room. I looked back as I went and saw her large boobies come out from under her bra as she raised her blouse. That just blew me away into the living room with the older folks; pulse racing. Liz followed as if nothing had happened, which it had not. I don't think that we ever talked again. One awkward moment; many to go. Soon after that incident, I began to carry the "rubber" in my wallet. I don't know why. Maybe just in case I got raped or something. At fifteen, I went on a student tour with my friend George and thirty other kids about the same age, eighteen girls and twelve boys. On the first day, we were training up to Montreal from New York City when a small but buxom gal began to lean up against the seat in front of me. Looking back on it several years later, she was putting her "brand" on me, but I hardly realized it at the time. She was very sexy, but I had no idea what it was that was on her mind. On the second leg of the journey, into the wilds of central Canada, she was the one sitting next to me, not George. Sherry was all over me, most notably when she announced that she was sleepy in the middle of the day. She'd squash one ample breast or another into my crotch as my member would attempt an assault on her ear...one or another. Darn, that felt good. But, at that point in time, my only orgasm had been a product of a wet dream. I didn't know what the heck to do with that little nymph. She was driving me nuts. It wasn't 'til Vancouver, in a cab, that she took my face and gave me my first kiss on the lips. It felt pretty good 'til I pulled away out of fright...borne of what, I don't know. For three nights after, the kisses got a little longer each night. The days...eh: tour-busses and such; most of which I don't remember. During the third kiss, Sherry ground her bum into my stiff pole. Felt great; but that was it for me. I traded Sherry for Sandi, George's less horny friend; a gal with whom he just talked occasionally. Sherry and George did not fit together and soon went their own ways...mostly with same-sex friends. Sherry cried off and on for a full day in San Fran before she met up with an older group of guys on another tour. She seemed quite happy after that. When I was sixteen, a seventeen-year-old gal came in from New York to stay with her aunt and uncle. Another friend of mine, John, a contemporary of my other friends' older brothers, was a swim instuctor at the club where she hung out during her stay. Unfortunately for John, she decided to go after me. Poor dear. On her next visit, ostensibly to see John play football for Hopkins, I came to visit him at his apartment near campus, and she was there. All over me, climbing up my back as John watched, she whispered that I should give her a call the next day, and slipped her number in my pocket. Okay. I called. My incubating pimples weren't too bad as long as I stayed clear of the light. We went downtown to see a movie at The Hippodrome. In front of her Uncle's house, she moved in close next to me in the driver's seat, put her hand on my thigh, and kissed me...hard, with her tongue cleaning between my teeth. I went as far as I had ever dared. Lying on top of her---and this was an attractive sophisticated gal---I let my hands roam to areas yet unknown to me. It was nice; and I think she thought so, too. I had high hopes for the next night when we had another date arranged. Oooops. Picked my face. Could not face her. Cancelled. Boy was I angry at myself. At seventeen, I asked a not-so-great looker if she cared to go out with me one night. It was summer, and she had season tickets for the Oriole games. I had heard that she was a wild girl. We went to the game the following night. Don't remember who won, or whom we played. This is what I do remember. We drove back to her mansion in the Valley (her parents' mansion) and she suggested that we take a swim. There was a nice pool in the back yard with a diving board, but I didn't know about it and I didn't bring a suit. She went on to say, "It's dark. Who needs a suit?" I lay down in a lounge chair thinking about disrobing as she galloped to the diving board, got on, went to the end of the board, and slid slowly out of her white blouse and shorts as I watched google-eyed. As she finished offing her underwear, I slowly became nude myself, hanging my threads over the chair next to me, as I watched her begin to bounce on the board. My penis was standing straight up as I dove into the water near the board. Bouncing up and down, I don't know if she saw or not. I was a thick slightly over 6"...just enough to pee with. Anyway, what else was it for? As I came right under her, she dove sideways toward one of two underwater lights; her breasts flying away from me, and her legs spread slightly. Ooooo. Ah. As I breast-stroked over to where she clung to the side, she disappeared under me and came up head to head as I turned. We kissed. Our bodies, at first perfectly upright, flowed into one another's crooks and crannies as I walked her down to the shallow end with her legs wrapped around my waist as if to cut me in two. Then I saw her. Her mother. Just as my virgin tickler was about to be sat on, Fran's mother blinked the pool lights and said "let's call it a night" from the kitchen door where she was in plain view. At eighteen, I was a freshman at an out-of-state school. Boys outnumbered girls by about eight to one. The first gal that I met was Betsy. She had been bussed over from the girl's counterpart university. We met in a crowd as she disembarked from the bus cavalcade that had brought three hundred girls seventy miles. I didn't get a good look at her, but she was female as I could discern from her large hooters. You might say I just took the hand of the hooters. Betsy and I walked around campus for a while and came upon the Arboretum where I suggested we sit on a close by bench. We did. And before I could get a word out, she was stroking my hard-on slowly up and down with her right hand---her finger-tips---to be precise. She was good. Very good. Back then, I never lost it. So she continued on finger-tipping in every imaginable way through my khakis. Wasn't this just fine, I thought to myself. Then I looked at her face for the first time, and proceeded to remove her hand. That was that. Back to the bus. To tell the truth, I never had a concious climax until I turned twenty. I had several other "almosts" before then. But not the big "O". I never had that until making love to a town girl who knew "what fer". She explained it all to me as we were, or she was, going about it. I remember her saying "stay calm, just relax". And there it was. How could my parents and friends ever keep such joy a secret. From that moment onward, I tried to make up for all of the stiffies that went unfulfilled in my teens. My best was seven in one full day. I'm not sure if these callouses on my right hand are from writing or masturbating. I'm fuming mad at Fred and George. I called them both recently and chewed them out for their oversight. They did laugh. You say masturbation comes naturally. I say it ain't necessarily so.