My first masturbation session was probably at age 15 and a half (yes, I know it's late), in the bathroom during the school holidays. I had read a section on masturbation in a book my parents had bought, and I was trying out the technique. Nothing seemed to happen, but it felt good, so I continued. After about 10 minutes my body was wracked with an incredibly powerful orgasm, causing me to cry out involuntarily. (Fortunately, nobody else was home.). My ejaculation was feeble — a tiny droplet of clear liquid appeared at the end of my penis. I couldn't believe what had just happened; I remember feeling incredibly proud that I was ready to be a father, glad that I was finally getting somewhere in my development, but still worried about my penis size (under 2.5 inches erect at that time).
Penis size has always been a bit of a problem for me. During showering after sports lessons at high school, others would stroll around butt-naked, their manhood swinging without a care in the world, and it seemed everybody in my year was "large." I remember skipping showers to prevent people from seeing me. Unfortunately, I was seen during the last week of my penultimate year and was taunted relentlessly for the whole week. (They forgot by the next term.)
Anyway, I first started masturbating regularly during my last semester of high school when I was taking my exams. I usually had only one exam per day, so when I got home, the rest of the day (until the family got home) could be dedicated to masturbation. Among other places, I masturbated on my bed, in the bathroom, naked in the garage (with the door closed), in the front room with the curtains open (my most ambitious), with the best place being in the loft of the house. Our house was semi-detached, and the loft space wasn't divided with a wall, and subsequently the people living at the house next door could have caught me at any time. They nearly did, but I managed to climb down the ladder, naked with an erection. This free time for masturbation taught me a lot about pacing myself to get a better orgasm, lubes (a *very* sore penis due to a whole week of frenzied masturbation forced me to find something!) — I started off using soap but found it caused the bit just under the head of my penis to become very sore (I'm circumcised due to problems at a very young age), so I changed to hand/face cream. I found this not only noisy (no good for the thin walls in my house) and difficult to remove if I wasn't in the shower. I've now gone back to using nothing if I'm not in the shower (I just grip lightly) and hand/face cream or shower gel if I'm in the shower.
When I first started masturbating, I had a big problem with guilt. The feeling I got after masturbation would depress me so much I wouldn't try it again until at least the next day, unless I forced myself — which was a shame really, because when I first started, I could start again instantly having orgasm after orgasm. Nowadays (I'm 19) I don't have a problem with guilt (mainly because I found JackinWorld), but I can't start again so quickly after orgasming - what a bummer.
Learning to drive at age 17 proved massively beneficial: I could take my brothers and sisters to school and return home to an empty house almost every day of the week. Also, we had moved to a detached house, allowing me to make as much noise as I wanted. Soon after moving I got myself Internet access and found JackinWorld, which gave me confidence to try new things (such as anal stimulation) and different variations. It also helped me with my size obsession, showing me that I'm perfectly okay.
Although I'd like to try mutual masturbation, I've never been able to. When I was at school I hadn't yet started puberty and so didn't even know about such things. I would like to ask one of my brothers (a year younger than me), but I don't think he would want to — he's not really that sort of person. I was thinking about asking my other brother (he's nearly 15), but again, I don't think he'd accept.
Masturbation and sex are very taboo in our family. It's just not mentioned, and if a TV program comes on that contains sex, the channel usually gets changed. I've only ever had one conversation with my brother (18) about it, and that was a very short "Do you do it? Yes, so do I" sort of thing.
My current masturbation pattern is pretty standard: I *need* to masturbate at least once every 12 hours, which usually means in the shower in the morning and late at night. In the morning, I wait until after I've taken everybody to school or work to have my shower, because then I can choose between closing the door and having a very hot and steamy session, or leaving the door open and walking around the house while masturbating, finally orgasming when I get into the shower.
During my late-night sessions I usually wait until past midnight so everybody else is asleep. I start browsing some adult sites on the Internet (I have many different age-verification id's), stroking myself slowly for over an hour. I don't use any lubrication, as I don't hold on too tightly.
After as much as 2 hours slowly stroking, I fold two tissues over my penis and start to increase my "stroke rate," building up to an immense orgasm and large amounts of semen. These are my best sessions, as I can indulge in fantasies based on the pictures I see, taking my time — it's sometimes very difficult not to moan out, but I've become quite practiced. The gender of the images I view changes depending on my mood, but I enjoy both male and female pictures equally. (I still consider myself heterosexual, but that may change in later years.) Sometimes I masturbate in bed at night, but my bed is very squeaky, so this is a rarely enjoyed luxury. Privacy is rare when the family are home (there are 6 of us), so I usually masturbate only in the shower or my room late at night — although I have risked it sometimes, nearly being caught in the process. A couple of months ago I was masturbating in my room, lying on my bed with the door open — fortunately I wasn't naked, having only pulled my trousers and shorts down. The rest of the family came home from shopping, and my two brothers ran up the stairs before I had a chance to "tidy up." Fortunately I don't think they saw anything, as they would certainly have commented on it — probably for the rest of my life! As soon as they were gone I shut the door, finished off, and got dressed.
My masturbation sessions vary in time from a couple of minutes (if I need to get it done quickly) to several hours if I want to take my time. Usually I try for several hours, as the resulting orgasm is a lot more rewarding. My longest masturbation session ever was 6 hours (honestly). I was at home alone all day and spent nearly 7 hours naked, masturbating slowly to some images I had downloaded. I managed to keep myself at nearly the brink of orgasm for about 5 1/2 hours using the "Stop & Go" method. When I finally finished, I ran a very hot shower, filling the bathroom with steam, sat on a small shelf at the end of the bath, and finished myself off — it didn't take long! The orgasm wasn't incredible (I've had *much* better), but the ejaculation was. I managed to shoot at least 6 feet with every squirt — had I been lying down (as I regularly am) I would have shot over my head and out of the open window! I've never managed to beat this yet, as I've not had the time, so I consider it a record to be broken when the opportunity arises.
Masturbation sessions have changed quite a lot for me over the 4 years I've been doing it. When I first started it was just a quickie in the bathroom every afternoon (usually taking less than a minute), with longer periods — though still only about 10 minutes, but usually many, one after the other — when I was at home on "study leave." Since then, I've progressed to longer sessions involving more fantasies and sexual images (I didn't and still don't have access to Playboy magazines, etc.), allowing me to enjoy myself more and explore my sexuality.
There are still some things I haven't tried. For instance, I would like to masturbate outside, in the sea, in the cinema (loads of people seem to have done this, and I'd like to try it), with other people (male or female), and basically anywhere/with anyone that would be a turn-on. I'm still worried about my penis size (I know I shouldn't be...), as all the others I've seen at school were over 6 inches flaccid.
I hope soon to fulfill some of my masturbation fantasies — holidays are upon us — and maybe meet some people for some mutual sessions. Here's to the future!