The beginning was meant to be a summary, but it turned into me recollecting my uninteresting life, so I apologize for those wanting a sexually rich story throughout.
To start off I've been masturbating for maybe four years, give or take. When I was younger, I was highly interested in my father's 'hidden' porn collection, and would observe it whenever I'd have a chance to be home alone. I wasn't sure why I was intrigued by such a publically illicit act; no one would ever talk about it, I wouldn't hear of it, there seemed to be no signs that anyone else did it, etc. So I guess that might be why.
I remember my first time masturbating was on one of the aforementioned occasions and for some reason, it felt really good when I would 'accidentally' rub my penis, although the pleasure never seemed to occur before that time. After a few minutes of this, I shot my first ejaculation all over my abdomen and was very frightened by it. I thought maybe I had done something wrong and if my parents found out, they'd be upset that it was because I was watching my father's porno (plus, my mom would've been angry at my dad for owning such things, so I didn't want him in trouble also).
After I thought I had broken my penis or something, I never dared touching it in such a way again, but, of course, my curiosity got the better of me, and being pragmatic, even at such a young age, I wondered if I could replicate such a feeling without the incriminating white substance appearing. Some weeks passed of me trying my best to not make the climax end with cum, and after many trial and errors, I thought, 'fuck it' and freely masturbated for the pleasure while not worrying about the evidence until after.
Months passed before I found out how to easily dispose of it... tissue paper. The idea was so ingenious to me that I felt I was the first to think of the idea (yes, I was a sheltered child who did not see any T.V. or movies with this implication). Before that, I had been cumming into socks and/or boxers that I wished to dispose of anyway. When I had run out of such resource(s), I felt that I needed something that could be easily and inconspicuously obtained and thrown away. Alas, an idea was born.
Maybe a year after I had started, I found out that it was common for many boys my age to be doing what pamphlets and elders called 'Masturbating.' The knowledge relieved me to the point of not being ashamed of myself from then and on, especially from those days when I would fit it into my schedule up to three or four times.
Around the same time I found out that not only I masturbated, I had been becoming very emotionally invested in, what would later turn out to be more than, a friend. At the time it was hard for me to point out what was special about him, but for some reason, I had felt differently about him than anyone else I had ever met. He had this charm about him, and niceness to where we got along great, and he was my neighbor. He was also the same age as me, so it was inevitable that one day I would ask him if he had ever masturbated. Recently, my memory has been leaving me, but from what I recall, his answer was yes. Although I digress, it was then that I found myself to also be mostly homosexual, and we started a thing together, but that's a WHOLE other story unrelated to masturbation.
The only reason I talk about that time of my life is because he started to open the door to, well, openness, namely about sexually mutual things. It had never escalated from there, as he had to move far away, and I never saw him again (until recently). Before this becomes a life story, the point is that when he left, I felt too afraid to try and participate in anything mutual with, say, my friends. I was always curious about their penises, although that goes without saying.
All these years later, I still masturbate around four to six times a week, and although I'm still young, I can no longer muster up the endurance to masturbate more than twice a day, although I always feel like I want to. Perhaps it's just because it's not a habit that I feel I NEED to fit into my day. I'm aware that this is becoming slightly uninteresting, so I'll get to the next point in this apparent Biography.
Weeks ago, my younger cousin was dropped off at this house so I could watch him, as his parents were going out that night and mine were absent as well, and he came into my room to see what I was doing, although he always expected that I was playing video games that he would want to participate in (which is usually true). This time, though, I was reading and didn't feel like turning on my game console just for his entertainment, but after some fussing from him and giving in from me, I did, and it kept him quiet for a while until he saw my wallet carelessly lying on the floor. He quickly snatched it away from view and opened it up out of curiosity, but namely to see how much money I had in there. At first he was very intrigued by the $300+ I had been paid from my job, but then (as cliche as it is to keep one in there) he found a single condom packet.
Now, I'm not sure what went through his mind when he saw it, but I guess his first instinct was to be, or act, surprised that I had one and/or am sexually active. He asked if I used them with a snide tone and smirk on his face, and when I answered in the affirmative, he quickly became (what looked and seemed to be (for some reason) embarrassed, as though he had something to be embarrassed about. After some awkward silence, he asked if I masturbated. Although he was holding a condom from my wallet in his hands, the question still caught me off guard. I told him that I still do, and before I let the conversation escalate into him asking who I've been involved with (with him assuming a female) I asked him if he does yet.
After some more silence on his part, he admitted that he didn't even know how masturbation worked, or what a condom was used for exactly, just that it's talked about a lot a school and that condoms are related to what his parents called sexual acts that they didn't want to discuss with him until he was older, although I must mention that the boy just turned 15. I slightly felt sorry for him, as I hadn't realized this, and asked if he wanted me to tell him. He seemed to light up at that idea, and quickly agreed. I described what masturbation is and what it's used for, and after some discussing, he seemed to be confused.
I think the way he understood it was that if/when people start having sex, that there's no need for masturbation, and so he asked me why I still did it. I told him that at certain times, it's much better to just get off by yourself than have all the convoluted rituals and steps that come with being sexually active. I guess the conversation started to bore him as he asked me if I'd show him what it looks like to put a condom on. I took a while to think about it, but found no harm in it, so long as he kept it to himself.
I stood up and began rubbing myself to get an erection going, and after getting good and hard, I took the condom out of its package and showed him how it's put on. Before that occurred, he was slightly mesmerized at how large my penis was compared to his. I'm only six inches long, cut, and perhaps four inches in girth, nothing I find too special, but for him, it was an entirely new frontier. After letting him take his gander, I slid my shorts and boxers down to my thighs, sat down on my bed next to him, and showed him how to properly apply a condom. He kept grabbing at his jeans to adjust himself, but never found solace. I asked him if he was comfortable, gesturing towards his apparent erection.
He commented that he only turned hard when he tried to sleep. I let him know that it was okay to get them, and that it was the circumstance that made him hard. He then asked if I could show him how I masturbated, and this time, I didn't think twice, for I was already exposed and, admittedly, horny. I found the condom too uncomfortable to work with and just took it off and started to slowly pump myself. Eventually, he felt obliged to take all his clothes off and expose his four inch hard-on. He's only just getting into the major swing of puberty, and so his pubic hair is relatively short.
I was still almost fully dressed, and although I'm slim, my modesty only let me take my shirt off. I slid my shorts and boxers down further to my knees, and increased my pace. He couldn't take his eyes off of my entire body, hardly even paying attention to me jerking off, and he started to grab different parts of my body just to feel them, I'm assuming, as odd and slightly uncomfortable as it was. He rubbed my armpits, chest, and legs, he ran his hands from around my neck to above my dick, and lastly I tried closing my eyes to imagine someone else, so as not to go limp by the fact that my cousin was getting his fill on me.
After a few minutes of this, he asked if I could help him get started. Although it was getting a little risky at that point, I decided to start stroking him as well. As I was getting into the stride of jacking him off, I only noticed then that he was uncut. It was interesting to work with, considering the angle at which he was lying next to me and that I had to use my right hand to stroke him.
In the midst of our session, I decided it best to stop jerking myself off, and to let him experience his first ejaculation in full. So, I told him to stand up, and I set myself behind him in such a way to where I could reach around him and jack him off with my right hand. With my left hand, I held his scrotum and started to fondle it a bit to see if there was any response from him. He showed no increase in pleasure and so I simply pumped him while slowly increasing the speed. His breathing began to become heavy and I felt him start to tense up, so, knowing that he was close, I told him to take a deep breath as I took my left hand and slid my finger up his rectum to reach his prostate. The suddenness made him yelp, but at that point, he started to moan loudly and finally, he let his ejaculation erupt all over my bed.
Shot after shot of semen were laid onto my bed sheet, and after the last of his cum dribbled onto my hand, he fell limp and I caught him before he hit the floor. I had always thought it a joke that some guys would pass out from the sheer pleasure, but it really seemed as though he was unconscious, and so I cleaned him up some, put our clothes back on, and laid him out on the couch in the living room. When I returned to the scene, my attention was brought back to the hot, sticky substance he had left behind all over my bed. Since I was horned up to begin with, I absent mindedly took some up with my fingers and smelt it. It was fresh, adolescent semen that had a very strong scent to it and I couldn't have been more turned on.
I reached into my shorts I used a bit of his cum to start jacking myself off. I was pumping away like it was Life or Death that I have an orgasm. In the heat of the moment, I picked the rest of it up with my free hand and heavily contemplated licking it off. Suddenly, my arm was grabbed from the side and I was pulled into a kiss as I unleashed all over my cousins jeans. This time, after every last rope shot onto him, it was I who almost collapsed. He propped me up as my legs became limp, and after realizing what just happened, he kissed me again. Although we're not related in any way by blood, I'm still not sure if it's okay to have been emotionally aroused by him kissing me, for we stood there for what felt like long minutes.
More recently, I told him that now that I'm 18, should anyone know or catch us masturbating together, I could get into a mess of trouble, and so now we try to distance ourselves when he's over, but I'm pretty sure I'll never forget teaching him how to masturbate.