When I was in those awkward teenage years, maybe 16 years old, I was small, thin, and shy. I had a circle of long-time male friends I had grown up with in our neighborhood. Typical middle-class suburbia in the baby boomer era. Of course, we were horny all the time but girls were still a mystery and we hadn’t had real girlfriends yet. My father was in advertising and would receive complimentary magazines because of his work. One of these was Playboy. Whenever an issue would arrive, my friends and I would pour over every page. My father was OK with this as he felt it important to know about the female body (thanks Dad). I now recall how we all had to adjust ourselves while paging through the pictures of beautiful naked women. Back then, just naked breasts and glimpses of pubic hair, but for us, enough to make our hearts race. Those pictures inspired many self-pleasuring events for all of us I’m sure. This was our world back then, charged with incredible adolescent male sexual tension.
In this context, I experienced my first sexual session with one of my closest male friends. Jim was the one boy with three sisters. Jim and I ended up spending long afternoons together just hanging out at his house, much bigger than mine. During those periods alone we fell into a habit of playing a game called “Doctor”. This would involve us undressing down to our briefs and then one person would be the patient and the other would be the doctor. The patient would indicate somewhere on his body where there was a problem and the doctor would then examine the area and perform a mock treatment or “surgery”. For example, I might indicate a spot on my upper thigh and Jim would feel it closely with his fingertips, move his hands as if he were doing an “incision”, and then “stitching” and other “therapy”. As part of each session, the “doctor” would often examine the whole body as well. Normally in a given session, we might trade roles a few times. Sometimes the patient had a problem on their back and sometimes on the front of their body.
I remember being erect through these entire sessions which could last an hour. With our hormones so strong in those days it was impossible not to be. There was always a choice as to whether you indicated a problem on the front or back. Both had advantages. If it was a problem on the front you could enjoy the naughtiness of exposing of your erection, bulging within your briefs, to the doctor. If you said the problem was on the back, you would lie on your belly and thus could press your erection into the mattress. Both were highly erotic but the second option tended to be my favorite. It was routine that after any procedure that the front of my briefs would have a large wet spot of pre-cum.
I remember being highly aroused the entire time. My erections would be almost painfully engorged by the end of these sessions. At first we would just follow this procedure and then go home, usually to masturbate as soon as possible!
Eventually, these evolved to become more pleasuring sessions. Jim would decide if he wanted front or back first and then I would lightly stroke and caress his whole body, alternating between feather-light touches and deeper touch. By this time we would normally both start on our bellies and caress each other’s backs, usually finishing by lightly touching the tops of the inner thighs and crease of our buttocks. Two highly sensitive areas.
By then we were highly aroused and ready to roll over. We would then repeat the gentle touching and caressing over the entire front of our bodies. We never touched any area covered by our briefs but our fingers would often trace the elastic of our briefs, coming tantalizingly close to our always hard erections and the normal wet spot of pre-cum. This went on for a number of weeks. The sexual tension was always palpable. We both unconsciously yearned for release but were afraid to go any further. We usually had music playing in the background and most of these sessions we didn’t say much, just focusing on our touches.
One day, as usual, we were in his bedroom upstairs, far from other rooms in the house, and there was a warm sun shining in the window which overlooked our other friend’s house next door. This day we had been teasing and caressing each other this way for an especially long time. We had become so aroused that we might orgasm without any touch at all. Something had to give. Jim finally broke the ice and said, “Would you masturbate me?” At first, I didn’t want to admit that I knew what he meant, although of course I did. I smiled and said sure, let’s do it for each other. Jim smiled, I think with a sense of relief that the tension we’d built up would finally be relieved!
Lying on his back I lifted the elastic up over his erect penis and pulled his briefs off. In the process creating glistening threads from his pre-cum. It was the first time I had seen him naked and noted his pubic hair being darker and thicker than mine. His penis was fully engorged, wet at the tip, and bobbed with excitement. Like me, he was circumcised and had a well-defined glans and corona. Below hung his heavy and full testicles. My heart was pounding from seeing his body, the knowledge that we would finally have release, and my own continuing arousal.
A little tentatively I started by gently lifting and cupping his testicles. Feeling their weight, gently rolling them in my fingers. Although I was focused on this, I remember clearly hearing Jim draw in his breath and as I continued my caresses, I felt his balls start to rise. I spent a lot of time on each one, lovingly rolling and tugging it. Eventually reaching lower to push gently on his perineum with circular motions and feeling the flexing of his genitals there. This whole time his penis continued to bob and ooze clear glistening pre-cum. I am sure at this point that his sperm had begun building up and Jim was probably feeling this pressure.
It was now time to move up to the center of his pleasure. I simultaneously ran a finger up each side of his shaft and at my very first touches his erection flexed strongly. I then lifted it up away from his belly and my fingers closed around his shaft. At that moment Jim let out a soft moan. I held still, letting him enjoy the contact of my hand around him. Feeling the heat and pulse of his penis in my hand. So hard and yet so soft, like I was holding my own organ. Such a strange yet familiar feeling.
I began slowly stroking up and down. We didn’t have any lube so my grip was firm but gentle. I knew from my own body just the right amount of pressure to stimulate the deeper tissue but not stretch the delicate skin too tightly. I kept the grip low on his shaft to maintain his stimulation at a high level but not too high, and let him enjoy the indirect tugging on his testicles that this grip allows. I continued this and over the next few minutes varied my stroking up and over his glans, corona, and the whole length of his shaft at a slow pace. “Oh my god that feels good” was all he could say between deep breaths and sighs. Of course I knew that it did. Soon his hips began to thrust against my hand and I could hear his moans becoming more intense. He was approaching orgasm.
I picked up the pace and focused on the corona of his penis, while at the same time fondling the back of his testicles and perineum. All the while I encouraged him, “that’s it, go ahead, let it out, let it all out”. In moments, he let out a loud moan and his whole lower body flexed as he thrust hard against my hand. A huge rope of semen burst from his penis and splashed against his neck. It was followed by several more heavy spurts that sprayed over his belly, each one accompanied by a loud grunt and thrust from Jim. The last pearly drops flowed down over my fingers as I slowed the pace but continued stroking so he could enjoy the whole orgasm.
Finally he let out a deep sigh, sinking back into the bed and you could see his whole body relax. I released his softening organ.
We were both in shock at what had just happened and for a moment I was afraid he would have second thoughts about pleasing me. “That was amazing!” he said, and I was so relieved when he gestured for me to lie down for my turn.
I lay back into the warm sheets, tinging with anticipation. My heart racing and doing my best to relax. Jim pulled my briefs down to begin. I’ll never forget that first vulnerable moment of being erect and naked with another person and the wonderful feeling of the cool air on my genitals.
Over the next few minutes, Jim lovingly repeated the exact same process I had followed. Long gentle caressing of my testicles and perineum. Teasing and then more urgent stroking of my penis and periodic touches in other places. The sensations raced through my body and I recall how almost involuntary my moans and thrusts were. The touch of other hands and the incredible pleasure were more than I had ever experienced.
Soon I was at that place where Jim had been before. Close to orgasm. Jim could sense it and followed the same process I had with him. Cupping and fondling my testicles and making long, faster, strokes up and down my whole shaft with special attention to the corona. “Now it’s your turn,” he said. “Go ahead.., cum hard”.
I felt that wonderful tingling in my testicles as they rose and the sperm began to flow within me. And then I went over the top and began ejaculating. As with Jim, a huge, powerful first spurt hit my chest and several heavy bursts followed. Thankfully Jim also continued stroking long after my semen had stopped flowing as the orgasm just kept going and going. Finally, I let out my last long moan and settled back into the bed.
At last, our desires had been fulfilled. Nothing was the same. It suddenly seemed late in the day. We rose from the bed and didn’t even wipe ourselves off but left our now drying semen on our bellies as we dressed. We made plans for the coming days and then I went home. My mind and body were buzzing from what had just happened.
We continued to be friends but sadly this was the end of our sexual sessions together. I think we were both afraid that it might distract us from pursuing the ultimate prize, a girlfriend. We never talked about it but I know in our minds we were grateful for the experience. The memories are still fresh many years hence and I do retain the appreciation of both the male and female body to this day.
