Chapter 11: Greg's Shameless Confession

Comments: There's something about sharing a secret with someone else that creates a strong bond. In this story, I'll tell you about the shameful, erotic secrets I shared with Greg, a boy two years younger than me in High School.

By the time I was 16 and starting eleventh grade I had taken five years of French in school and had become very tired of it. I was ready for a change. So, I enrolled in Beginners' Spanish instead to start the new school year, and was put into a class filled with shiny new ninth graders. I really wasn't crazy about this part of the deal, but I figured anything would be better than another year of French, which I truly hated.

I looked around the room at all the boys and girls two years younger than me, most of whom I had never met before. I sat near the back of the room, and the boy seated behind me was a sort of scrawny, cute, curly haired redhead named Greg, with wire rimmed glasses and braces on his teeth. (Looking back now, he looked like a pubescent version of Chuckie from the Rugrats cartoons) I soon observed that he didn't take life too seriously, and I found myself laughing at his frequent but subtle little antics in class. He wasn't especially cool or handsome; in fact he was even sort of nerdy. But he laughed at all my jokes, and I especially liked how whenever anything happened in class that might provoke some humor, he immediately glanced at me to test my reaction and to laugh with me. He was so much fun that I even started to look forward to daily Spanish class, in spite of myself.

One day we were throwing back and forth some subtle, typical teenage sexual innuendo and he surprised me by almost flat-out admitting that he masturbated. I was really shocked, because he said it in such a matter of fact open way that showed no shame at all, as if it was the most normal thing in the world. We moved on and the topic was dropped for then, but for me it was hardly forgotten! I was suddenly curious and wanted to find out more about Greg's private habits, and somehow I was sure he'd be willing to tell me. I desperately wanted affirmation that I wasn't such a freak, and if compulsively playing with one's self was a habit Greg enjoyed daily as well, I sensed it would make me feel better about myself. Frankly, very few topics were off limits when boys talked to each other anyway.

The next day before class began I joked with him, and carefully, tactfully I somehow steered the conversation again into sexual mode, and before class was over, I hinted to him that I masturbated too, as casually and normally as could be possible. Slowly, surely I tried to find out more, and I found him very open, eager and willing to confess. Softly one day before class I came right out and asked him. "Do you like to masturbate a lot, Greg?" I asked. This question had two possible meanings--and I wondered how he'd answer. One meaning would have been that he enjoyed it very much, the other would be to admit that he masturbated very, very frequently. He surprised me by actually answering both questions.

With a broad smile and bright eyes he said "Oh yeah! I love it and I almost can't get enough!" he admitted willingly.

Equal disclosure was fair play, so boldly I admitted the same to him. "Me too!" I said happily. "I do it almost every day!"

"Almost every day? He said seeming surprised. "I do it at least once every day!"

This admission threw me back in my seat. It was one thing to admit the deed, but another thing entirely to shamelessly brag about doing it as often as you could! I was suddenly euphoric. Had I finally found someone else who might do it as often as I did? "Really!" I said. "Well, me too, I guess. I do it as soon as I get home from school and then usually at night in bed too."

"Same for me," admitted Greg easily. "But sometimes I even have to pause during homework for some 'relief' too." He shook his cupped hand up and down for emphasis near his waist as he said this, and I thrilled that he seemed to be a practicing lefty- the same as me. Class suddenly began and our conversation had to halt for right then, but my mind was spinning. I had, indeed found someone else like me! Maybe knowing Greg was going to be even better than I had imagined, because he seemed to suffer not a shred of guilt about this shameful obsession that I suspected secretly gripped every boy, as he was willing to discuss it like it was no big deal at all.

Building a friendship with Greg was somewhat challenging, as our interaction occurred only in small snippets before and after class. Because he was in ninth grade and I was in eleventh, there was no overlap in our schedules save for this one class. We almost never crossed paths in the hallways, and we each had our own sets of friends we hung out with. Our conversations were always brief, but always to the point.

"Did you do it yesterday, Greg?" I'd ask in a whisper, sliding up beside him.

"Yes, twice!" he'd beam, holding up two fingers, signing his accomplishment.

"Me too! Twice!" I quietly but excitedly answered, euphoric that another boy was as wrapped up in this private obsession as I was.

The teacher had moved all our seats around mid-year, and Greg now sat halfway across the room, but we always still smiled at each other and made eye contact near the beginning of each class, him holding up one finger or two in my direction, indicating the number of times he had jerked off the day before. I'd reply with a display of fingers of my own, one two or sometimes even three. Once he flashed me two fingers, then right after that, flashed a single finger, which puzzled me a bit, so after class I asked him. "What was the 'two-and then-one' sign you gave me?" I asked.

"That meant that I did it two times yesterday but already once today!" he replied.

"How?" I asked reverently

"This morning, when I was getting dressed I had a boner that wouldn't go away so I had to take care of it the right way", and he motioned his hand back and forth with his fingers in a ring, giving the universal sign for jerking off that every boy knew. I wanted to know more, and I wondered how much he'd tell me.

"Where did you do it?" I asked "In the shower?"

"Nahhh...," he answered. I just pulled down my pajamas and did it standing up before I put my underwear on. It was pretty quick!"

"Where did it go?" I asked breathlessly, referring to his squirted emission... a question that if asked to 99.9999% of all the other people in the world would have been used to confirm in their minds that I was certainly a freak and would have been greeted with an angry frown and a cold stare.

"Are you kidding? I always have tissues handy everyplace!" he laughed, identifying himself as one of the world's .0001% of the population who would consider mine a reasonable question.

This kid was so cool... I would never have imagined admitting such things to an older boy. I wondered what his motivation was. I was Catholic, and Catholic boys were taught from an early age that masturbation was a sin (they euphemistically called it "impure touching" so as not to be to specific... or instructive). Greg was Jewish, and I wondered if that may have played a part as he apparently had no such hang-ups. But I never was able to have a deeper conversation with Greg about the topic, as circumstances never placed us together long enough to allow this to take place.

I fantasized about him a little bit. I imagined how he might look jacking off in his bed. I wondered which hand he used, how long he made it last, I wondered if he had much pubic hair, and if it was as red as the curly hair on his head. I wondered if he had any hair on his body, or how much stuff he made when came, how it looked when it came out, or how far it squirted. I wondered if he always kept tissues nearby to clean up, or if he sometimes used an undershirt or sock. I mused whether he rubbed it dry, or if he used some sort of lotion for lubrication. And, one by one I found out all these little facts, one a day, one question at a time. He cheerfully answered all my queries, and I reciprocated by telling him my like, similar habits, also one at a time. He never acted at all like my behavior was odd, and that my questions were out of place coming as they did. He just seemed to accept my sexual curiosity and our masturbation as something every boy did, like eating or sleeping, and he obviously carried no burden of guilt when contemplating it.

One day I was wide eyed as I displayed two fingers across the room to him, and he turned and displayed FOUR fingers to me! I had to know more and after class I corralled him outside the door in the hall.

"FOUR? Wow!" I said. Of course he knew exactly what I was referring to without any deeper explanation. "When did you fit all of them in?"

"When I got home, then twice during homework and then when I got in bed under the covers," he admitted. I learned that his personal maximum had been four, but that he had equaled this record many times. My record was six, and I told him so, and he let out a low whistle of admiration.

"Six," he said. "That's more than I ever did it in one day!"

It had happened only once, that summer that I had been sent to stay at the seashore for several weeks with my elderly grandparents, alone. It was the summer after eighth grade, so I was 14, and I had never been hornier in my entire young life. As soon as I had finished, it seemed I was ready to go again, and again. And with nothing else to do jerking off was the best possible high pleasure, low-budget activity a kid could ask for. Sometimes I'd peek out the third floor window of the old summer house, looking longingly across the street at the big house where a family of 13 brothers and sisters lived, all blonde, and ranging in age from 3 all the way through 20, with nary a gap for breath in between. There were two or three sets of twins, at least two-thirds of the kids were boys and they seemingly all surfed. How I longed to get to know the teenaged boys my age or older, but I was sort of shy and there were so many of them that they never had to go outside the family to look for playmates. So, I'd gaze at them from my window as the boys skateboarded in the street below, imaging how they'd look naked or whether or not they played with themselves too--and wondering if any of them ever paired up for the fun, or if the older blond brothers taught new tricks to the younger ones, and soon I'd be squirting streams of boy-cum into my hand as I gazed at them all.

Then there were the (very few) days when I'd signal one or more fingers Greg's way, and he'd shake his head and hold up a "zero" made with a circle of his finger and thumb. This didn't happen more than a few times, but when it did I immediately felt an impact of sadness like pressure on my chest, almost like his having taken a day off meant that he had given up the hobby and left me alone in it. I'd ask him after class why he hadn't done it the day before, and he'd shrug and carelessly comment that he was too busy or didn't feel like it. So, while there was no significance to his occasional isolated day of chastity, I attached powerfully sad emotion to the news, hinting at how insecure I still was about myself inside.

One day as the year drew to a close, he told me a story that was very exciting to me. He said. "You know Mike from our class? I pretty sure he caught me doing it yesterday. I think he saw me through the window."

I was certainly very interested. "What happened?" I said, my sexual arousal bell going off both inside my head while causing a stirring in my pants.

"Well, I came home and I was so horny that I couldn't wait," answered Greg. "so I dropped my books and went to the basement rec room and sat on the couch and dropped my pants down and started rubbing my cock." He was shameless and graphic about his needs and this was so erotic to me. "I had just walked home with Mike, and I forgot that I had his science stuff in my backpack, and he remembered after he got halfway to his house and came back to look for it. Except he didn't knock on my door, instead he came right around to the basement window and looked in... and I was right there on the couch jerkin' myself and he looked right at me!"

My mind raced ahead.... This situation was ideal to find out what Greg's reaction was in such an embarrassing situation. I wondered if maybe he had covered up in horror and Mike had run away, or if he had let Mike watch him, or maybe invited him in to join in the fun.... I had to know!

"So, what happened next, Greg?", I asked breathlessly.

"Nothing much," Greg shrugged. I went around to the door and let him in and gave him his stuff and he went home.

"That's it?" I asked with great disappointment. "Did he say anything to you about what you were doing? Did you say anything to him? Would he have stayed and done it with you if you asked?"

Greg looked at me slightly puzzled. "Huh?? No, neither he nor I said anything. I gave him his stuff and he went home. I'm sure he must do it too, so it wasn't a big deal or anything..."

"When he left, did you finish doing it?" I asked

"Of course!" answered Greg. "I picked up where I was and jerked off till I was done. It was just like always!"

My emotions were highly stirred... and I wondered intensely, had there been any significance intended to the telling of this story? How should I have taken it? Perhaps Greg wanted me to know that he wasn't embarrassed doing it and having another guy watch? Maybe he was telling me he wanted to be watched? Maybe he was hinting that we could do it together? Or was it just an innocent, forgettable daily happenstance that he told me in passing like so many other little details we shared day-by-day over the year?

Because the school year was drawing to a close, I was afraid I'd never see Greg again after that year. Though he personally wasn't a subject of many of my erotic fantasies, I was never one to let an opportunity pass by, and I desperately wanted to take things just a little further along with him before he and I lost touch, maybe forever. One day as the year had almost ended, I came right out and asked him:

"Greg, maybe if I walked home with you after school we could do stuff together?"

"Stuff?" said Greg. We had never discussed getting together outside of the classroom before, and I'm sure my request surprised him.

"Yeah, maybe I could come over after school and we could do "it" once together. You know... since you do it and I do it maybe it would be fun just to do it one time together..."

The frozen look on his face conveyed how horrifying this suggestion was to him. Clearly, it wasn't anything he had contemplated, and now faced with the opportunity, it surely wasn't appealing to him at all.

"Geez no, Brad!" he said. "I don't jerk off with other guys! That's something that's meant to be done alone!" He looked confused and unsure what to say next.

"That's OK," I said, letting him off the hook. "I just thought it would be fun, that's all." I was disappointed, but not overly surprised. My style was never to be so forward with another boy; instead I'd let the seduction stretch out over a safe period of time, and so would never come to such an outright, bold, in-your-face "YES OR NO and tell me right now" question as I had asked Greg. I consoled myself that if I had really, really wanted to have masturbated with Greg I could have accomplished it with just a little more time and some better planning. But I suspected that my time with Greg was growing to a close, and I was right. After that year, aside from a few times passing in the halls, I never really saw Greg again. But for that single year, it was nice to learn so much about another guy who did it as much as me!