The summer of my fifteenth birthday I was masturbating regularly. Three sometimes four times in the afternoon after school. All these years later you cannot imagine the total lack of information on sex that was available to a teenager in the mid fifties. There was something you were supposed to do but what it was remained a mystery to me.
That summer a friend from high school stayed at our farm for a couple of days. We ran around the fields on the tractor, took long bike rides. But the item that sticks in my mind is on one afternoon winding up in the bedroom with him naked. While he was younger than I, he was British and a lot more worldly. He instituted some mutual masturbation, which really was quite nice, but didn’t lead anywhere. We lay there for a few minutes fondling each other’s dicks, neither of us came. The next day the same thing happened, while he was more sophisticated than I, he may have been afraid to go any further.
For my part I found it quite frustrating, there was something else I wanted to do but couldn’t figure out what it was. When the school year began I shunned my friend, as our actions had caused a great deal of confusion and shame in me. I didn’t want to be branded a queer, even though there was no comprehension of exactly what this meant.
Segway three years, I am in California away from my native upstate New York awaiting the start of classes in a technical school. On this warm July night I and my a few of my classmates were at the local club, telling lies, and just generally shooting the breeze as young men do. An older guy joined us; say 27 or 8, ancient by our 18-year-old standards. His joining our conversation and the fact he would sit and talk with us impressed all of us; plus he impressed us even more by buying us a round of beer. Being from New York I was not used to the 21-year-old California drinking age of that time.
He was shorter than I by a good four inches, short dark hair, clean shaven, as was almost everyone at the time. His status as an instructor caused the group to pay close attention to his every word. We talked, and drank some beer, and talked some more. Soon the group began to thin out, till it was just the instructor and I left at the table. He listened to my chatter, at closing time offered me a ride to my quarters. This was a distance of some two blocks, strange in retrospect, but I readily accepted.
His car was Southern California all the way, a Jaguar Sedan, leather seats, four on the floor. I was impressed. He quickly drove the two blocks to my quarters and parked in the large lot, inconspicuous between two other cars. The lot was illuminated only by the lights from an entrance, and was quite dark.
We talked some more and then as there is in any conversation amongst strangers there was a lull and silence. The radio was playing softly in the background, we sat there and the silence became heavy. He adjusted his seat backwards and I could see him fumbling in his lap. He had undone his trousers and pulled his dick out. Once ready he looked at me and placed his right hand on my neck and gently directed my head into his lap. Like a duck to water I laid down on the seat and took him in my mouth and began to suck him. He kept his hand on my neck encouraging me to eat him. He didn't try and fuck my mouth, he just allowed me to suck his dick. I recall thinking I would have to brush my teeth really well afterwards. It just seemed like the proper thing to do, he had been nice to me, and now I was going to repay his kindness by giving him a blowjob. I continued to blow him and would have sucked him to climax had he not pushed me into the back seat.
He climbed into the back seat behind me and with some erging got my trousers down and began to make love to me anally. In passing years I have read many stories and accounts of first time anal intercourse, all seem to indicate a degree of problems with the first penetration of the receivers rectum and some pain. Surprisingly he had no problems entering me, there was no resistance he just slid right in, as if my ass was designed to accept a cock. This could have been due to his skill, as he was very experienced at fucking young men. It could have been the result of his cock being well lubricated by my saliva. Or perhaps it was due to my rectum being eager to receive his hard offering.
Whether it was just habitual with him, or he had learned from experience, the easiest way to take a male or female anally the first time is with the subject flat on their stomach, even it they protest, there is not much you can do in this position, except lay there and be fucked. Besides if you have just sucked someone off, you shouldn't object to his finishing off in your ass. As a friend of mine use to say "I have never met anyone I couldn't fuck, once I got the head in."
So now I am face down on his leather seats taking it up the ass. There is no emotion here I am an object that can suck him off and be fucked. There is no attraction, no romance, just sex. After what seemed like an hour he finally came. I often wonder what he saw in me that told him he could put his dick in my mouth and I would suck him off, and then I would let him fuck me in the ass. That night the instructor made a woman out of me in the back seat of his Jaguar, now I knew what had been missing.
Once he filled me with his cum, with just a couple of mumbles I pulled up my trousers and went into my quarters. I never saw him again, he was subsequently arrested with another male teenager, he jumped bail and ran, and no one knows where he is to this day.
Even now years later, when a Jaguar Sedan passes on the road, or I spy one in a parking lot my mind immediately returns to that warm night in July. The memories of the instructor feeding me his cock in the front seat and my eating it, then being fucked in the back my face pressed down into the seat cushions comes flooding back.
I guess the point would be I found out what one is supposed to do. This would not have been a conscious choice, as some would have you believe, but rather the natural culmination of a dee[ seated desire. In thinking about the mutual masturbation sessions with my boyhood friend, just the slightest bit of prodding I would have bent down and taken his young firm cock into my mouth and sucked him off while I milked his balls. At some point my leg would have swung over his head, and I would have offered him my cock to suck. We would have lain there and sucked until we both came in each other’s mouths. Then I would have rolled onto my stomach offering my ass for him to fuck, and let him make a woman of me.
Just about the time you learn what to do you are no longer able to do it that well.
NOTE: Lest you think that this is just a fairy tale (no pun intended), let me give you a few more details. The instructor was a Staff Sergeant, a combat veteran of Korea and a former Drill Instructor, hardly the sort of individual preceived as a prancing queen. I am sure there were lots of recruits in his platoons that made it through boot camp based on the availability of their assholes. You cannot say he was an institutional homosexual, because there were plenty of women available in the area, he was just an adapt seducer of young men who did not as yet know their orientation. As to his getting caught, he was found with a young private in the back seat of his Jaguar. The private later claimed he just wanted to get a blow job, but the instructor got blow jobs he didn't give them, and the private's rectrum more than likely felt the intrusion of a cock. Rather than face a court martial the instructor ran, probably across the border into Mexico, only 17 miles away. The private got an undesireable discharge, which would haunt him to this day.