Chapter 22: Teaching Tad

Author's notes: Up until this point, my stories have been fairly innocent, involving exploration with others my own age. But looking back, I must admit that at some point in my life, I surely began to lose my compass. Here is a turning point of sorts as I began to involve my younger brother, Tad, in my exploits, and with perspective of an adult I will offer that I am not proud of this turn of events. There is not an honest balance of power between a boy 16 and one who is 10. Tad looked up to me and was an inquisitive and cheerful boy who trusted that anything and everything I did was right and good. While he swears to this day that noting we did together was coerced, I can't help but have nagging guilt that I started by crossing the line here, and I began to cross that line with others more and more frequently in the years to come.

While I am sure that brother-brother experiences are not rare in this world, I don't think that they should be accepted and considered generally healthy. In my case, as difficult as this is to admit, here began a pattern of behavior that could be judged as depraved by society.

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I usually perceived my younger brother Tad as a constant thorn in my side when I was growing up. Some six years younger than me, I was rarely kind to him, very ironic especially considering how much I simultaneously fantasized about having an older brother of my own, who would tenderly care for me and whom I could idolize. Clearly with hindsight, my meanness to him was thoroughly and sadly misdirected. Tad was a cute, easygoing, good little kid who was respectful, cheerful and who generally stayed out of my way. He never "told" on me or even goaded me into doing things that he could report to my mother with the result of getting me in trouble. Nevertheless, I thoroughly resented his presence on the earth, maybe because I believed that I competed with him for my parents' attention, but more likely, (please excuse my overly-deep psychological bent; it's just my nature) my real belief after all these years is that I despised him because he looked and sounded so much like me, and inwardly I despised myself. Suspecting I was homosexual before I even knew what the word meant, I realized that it made me feel like a freak and must always be kept a secret from everyone till the day I died. Today, I look at photos of Tad and me as children, and without knowing the date or reading the name written on the photo's back, it is difficult for even me to determine if the photo is of me, or if it is of him. Looking at Tad was too close to looking in the mirror at myself.

I'll confess some earlier sexual involvement with Tad, as I most likely taught him to masturbate when he was still in grade school, instructing him almost for the sport of it. I was probably about 16 and Tad was only 9 or 10. We had been on vacation as a family, and had taken plane flights that had consumed the better part of a long day. As we rested in our hotel room, the day was still bright outside since we had crossed many time zones while chasing the sun across the sky, but we were dead tired and needed a break. My family took up two rooms, and Tad and I used one of them. As we sleepily lay fully dressed beside each other on the bed, still even wearing our shoes, without any prior forethought, I began to wonder what Tad knew about sex. I recalled vividly being his age, and being very horny then even though I didn't myself learn to masturbate till I was almost thirteen.

I was in that half-asleep state where one's judgment perhaps is not the best. Tad lay sleepily next to me, though he was certainly awake. Because he and I didn't have an open, speaking relationship which I could have cultured if I had wanted to (truthfully, I treated him badly, communicating mostly with nudges, pinches, pokes and pushes with the occasional hissed insult thrown in) I couldn't ask him what I wanted to know. So, instead I reached over to him and started to feel him. Through his clothes I rubbed up his legs, eventually arriving at his thighs. His corduroy pants were sort of thick material, but by feeling around I soon found a little stiffie poking up in there, obviously invigorated by this exciting, unexpected and sudden contact.

Tad didn't say anything and neither did I. But I continued to stroke and fondle his little boner through his pants as he lay quietly next to me, finally gripping it lightly making it stick straight out, and gently rubbing it up and down using only two fingertips because it was so small. In just a matter of minutes Tad began to wriggle and jerk, thrusting his hips very slightly forward off the bed as I rubbed gently. Then, rubbing just a little harder and a little faster, I felt him twitch and watched him thrash slightly side to side, watched his fingers stiffen and claw at the bedspread, and heard his breath catch in his throat as he stiffened and froze. He then collapsed weakly backwards breathing quickly as he relaxed.

It was clear that I had given Tad an orgasm, and I guessed it might be his first one. But I didn't ask him, and not a word was spoken between us about it as we continued our nap. But the next day when getting ready for bed, Tad snuggled close to me and said simply in a quiet little voice, "Do it again, Brad."

I smiled inside. This time there was no pretense, I unsnapped Tad's pajamas and found his little peter already stiff and ready, and holding it between my thumb and forefinger I rubbed back and forth while Tad closed his eyes, smiled and laid back on the bed in rapture. It didn't take long and he was wriggling and thrusting again, his whole body suddenly stiffening and then falling backwards in relief, and this time I could see that there was no emission at all, my fingers were completely dry as his tiny erection briefly wilted. But only a moment later he was hard again, and wiggling towards me, again I rubbed him and again he climaxed once more in just a minute or two's time.

Tad obviously had discovered a new hobby that could keep him busy. I was amused more than anything else, as little boys like him were not especially exciting to me, and the fact that he was my brother was not particularly any sort of turn-on as a part of my erotic fantasies either. But I had to admit it was erotic for me to see him get so excited and horny, and that he wanted me to give him release.

When we returned home, I soon learned that Tad had taken this new, adult, knowledge and had practiced it shamelessly. I saw him in his bed one morning, pajamas opened, nakedly exposed and rubbing his own little cock, and as I passed by in the hall he made no attempt whatsoever to cover it up. When he had finished and come downstairs, I asked him slyly "so, was it fun?" and he answered by giving me a little grin as he drank his milk.

Again, in hindsight, while these little interactions may have been only an amusing diversion to me, I strongly suspect that Tad assigned them a much higher level of significance. It would only be natural that he wanted to have a pleasant relationship with me, his big brother, but I had demonstrated by my hostility that I was clearly not interested in a developing a normal, appropriate and friendly one with him. But I had initiated this enticing, taboo sexual activity, and to him this new way of interacting with me likely had several angles that made it extremely appealing. First, it felt good. I challenge you to show me a boy who doesn't like to have orgasms, and the more of them the better. Second, it was an excitingly highly adult secret we could share together and not something either he or I would be sharing with our parents. Third, he had found a way to get my attention and probably, as he saw it, my love.

I soon found out that he had quickly begun to leverage this newfound mature level of knowledge with his other like-aged friends, teaching them one by one how to masturbate, hosting increasing numbers of basement sleepovers and back yard campouts that likely included initiating his circle of friends one at a time into this new world of nearly adult sex, with Tad as the skilled teacher.

I'd ask him about his suspiciously high number of repeated sleepovers with a specific tall and gawky school pal in the backyard tent, a tall boy who was all arms and legs and big hands and feet, silky brown and carefully-parted and Brylcreemed hair, big sleepy cloudy blue eyes, flushed cheeks and a ripe red mouth that always hung slightly open. He eagerly told me that this boy had started puberty early and had already known how to masturbate. So when he discovered that Tad knew about this boys-only highly-classified top secret magic trick as well, the two of them had become inseparable, but oddly I had noticed ONLY for sleepovers and nothing else, as the other boy longed to do it with Tad as often as possible and wherever they could. It was clearly the only thing they had in common.

Tad had also taught Billy, the same-aged boy next door, and Tad told me they enjoyed pushing their pants down on Billy's bed while his mother was away and masturbating each other while lying closely together, apparently without any sense of burdensome shame at all. I was slightly jealous when I learned that Tad was also masturbating with another mutual friend, a cute apple-cheeked boy named Petey who was exactly three years older than Tad and three years younger than me, and whose parents were friends of our parents. Petey had consistently, clearly but gently resisted my overtures to "play" over the past months, yet he seemed to have eagerly welcomed the chance to "play" with Tad. Tad told me that while Petey had a smooth face, a pretty high voice and still was pudgy with baby fat, that his cock had already grown huge– In fact, bigger than mine, Tad reported with some awe in his voice. How envious I was! I wanted to see Petey's big pink cock too, but Petey was definitely not into fooling around with me, and as I've said before, If someone wasn't interested in me I was not into forcing anyone to do things they didn't want to.

After Tad's brief period of summer instruction from me had ended, I had returned quickly to games with other boys my age and older, as they were the true subjects of my masturbatory fantasies and the focus of my illicit lusty attraction. But I'd still smile when I'd see Tad and neighbor Billy sitting on the porch wearing their sneakers with no socks and little cotton gym shorts, at least one of them having a small round wet spot visible on the fronts. I'd casually ask, pointing to the spot, "So, when did you guys last do it?" and curly haired Billy would answer shamelessly "I dunno, maybe ten minutes ago?"

Tad remained very open and unashamed about letting me see his body develop as he grew through his early teen years, and I'll confess a guilty pleasure at being able to watch my younger brother go through puberty before my eyes, watching sprouts of hair appear at the base of his cock, and seeing him grow taller and nicely well muscled with a trim, tight physique that was rather different from my broader, thicker one.

I'll admit an occasional sense of nagging guilt at becoming aroused from looking at him, but I never went so far as to try to plan to catch him in sexual situations, though as it turns out, these situations came up often enough on their own. We shared a bedroom, and we often would each masturbate ourselves in our own beds at night without any attempt to hide from the other what we were doing.

One night while Tad's jerking hand caused his blankets to pop gently up and down as he lay in bed, I sat down on the edge of the teenager's bed and presented him with an illicit prize—a condom, still tightly rolled up and sealed in its foil wrapper.

"What's that?" he asked, stopping his under-covers rubbing.

"It's a rubber", I said. "Try this" And unwrapping it, I pushed the blankets down exposing his slim erect penis to view, for which he made no attempt to stop me. Placing the rolled condom on the end of his cock, I rolled it gently down to cover it up, then gripping his stiff smaller shaft I rubbed up and down, immediately noticing that he was large enough now for me to grip his erection with my entire hand.

Watching me intently, he was obviously intoxicated by this naughty new twist. It took only a minute and he began to thrust and buck as he came violently into the condom, and I rubbed more slowly and watched the tip fill with shot after shot of his white liquid. "How was that?" I asked, leaving him to clean up, and he didn't answer as I recall he just let out a little moan, obviously thoroughly spent with his climax.

We had a weightlifting bench in our shared bedroom, and Tad used it religiously. I was probably stronger than him by far, but while my muscles were thick but (to me) unimpressive to look at, at fifteen Tad's were bandy and tightly stretched and looked much more well-defined. One night as he worked out, I closed the bedroom door and locked it, then as I lay down on my bed I asked him "would you mind taking off your shorts and working out nude so I can watch, just for tonight?" Without batting an eye or asking a question, he slipped off his small gym shorts, and totally naked he did all his exercises in front of me, while I lay on my bed to watch and jerked my erect cock, intently following his every move. He paid no attention to me whatsoever, and I came shortly thereafter, catching my squirting cum with my free hand to prevent it from hitting my face, as it always flew with such force.

Later, when I was in college, during my holiday trips home starting when he was only thirteen, Tad and I would squirrel away together in our bedroom, and laying head to toe beside each other I would slip down both of our trousers, and we would rub each other to blissful orgasms while my parents slept in the adjoining room. One evening as my mother prepared dinner, Tad come into my room, and pulling my cock out of my trousers he leaned forward and to my delighted surprise sucked it for the first time, and I almost went out of my mind. I wondered what had come over him to try this stunt. While I had sucked him several times, I usually only did it for a moment or two before I resumed rubbing him to make him squirt. That afternoon, Tad deep-throated me like an expert and when I began to tremble as my orgasm approached, I tried to warn him so he would take his mouth away. But he obviously didn't want to, and buried his face in my pubes as he allowed me to shoot deep into his throat. This crossed the line of delighted depravity for me—and as wicked as it was, it lit a fire inside of me that caused me to soon begin doing this to him on a semi-regular basis as well. Many nights, after lights out, he would crawl into my bed as soon as the room was dark, and we lay head to toe in a sixty-nine position and would now often suck each other to orgasm instead of rubbing. We were so well practiced that we could come nearly simultaneously every time, without a single word of communication between us. We were secret regular jack-off buddies, Tad and me.


Going back and doing the math, we repeated this scene and many others hundreds and hundreds of times over the next years. He would do anything I suggested, and anyplace I wanted, every time I asked. I sucked him off in every room of the house plus the garage, after school, before, in the car and the tool shed. I jerked him off outside, in the woods, at the beach, in the showers at the YMCA. I invited him to spend the weekend with me at my college dorm and spent the whole weekend masturbating together with him again and again, whenever I pleased. I would ask him to lay above my face and rub his erect cock on my cheeks and dangle his balls into my mouth while I jerked myself to orgasm, and he would gladly comply. And finally, I asked him if I could masturbate with his same age friends with him—and he didn't disagree, at least at first.

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I don't want to get all moralistic here, because I know that most are reading for the thrill of it, but I don't think there are many situations where it is acceptable that an older boy should get sexually involved with a much younger one as I did, perhaps especially if that younger boy was his brother. Even at the time it was happening, I recall that my interactions with Tad were conflicting to me, not as exciting as they may seem here written explicitly here on the page some thirty years after they happened. As I said before, I suspect strongly that Tad's willingness to go along with me was based on his desire to please me, and on his great desire to be included in my life. I chose to include him instead in this particularly dark, confused facet of my life, when I could have instead been teaching him to throw a curve ball or to tune a carburetor. I also fear that Tad looked up to me so much that nearly ANYTHING I did at that point in his life he would have used as a reference yardstick to measure right from wrong. Or, in other words, by definition, BECAUSE I was doing it, it must have been right. As a pre-teen then a teenager, Tad was always a willing participant in these masturbation sex games, eager, smiling and happy. I like to believe that I simply helped him learn to masturbate without shame, and his rather open relationships with his like-minded guy friends through his teenage years, which I will tell you more about soon.

I asked Tad several years ago about this. It was clear that my bringing up the topic startled him. Tad is about 40, married now for a dozen years, and has two beautiful small daughters. He's a serious fellow—barely resembling the cheerful sprite he was as a small child. Point blank, I asked him how he felt about our years growing up together. He thought for a while, and gave me what I believe was his honest answer.

Regarding my being unkind to him, he told me that he really doesn't remember much about it. His memories of me are that I was nice to him mostly, and none of the teasing I gave him was memorable or any different from what he remembered his friends receiving from their big brothers. Then I asked him specifically about the initiation I gave him into the world of masturbation and whether or not he resented it. To this Tad expressed surprise, saying that he never questioned it at the time or afterwards. "Huh—that?? I don't know, I didn't ever give it much thought; it just WAS," He shrugged. It quickly became clear he didn't want to talk about it anymore. "It's not something that I worry about, if that's what you mean."

I still don't know what to think. True, it just "was", and at that it was a long time ago. Still, it's not something I'm proud of, as it is too likely that relationships like this one are based on the misuse of power rather than on lighthearted fun. I don't recommend it.