I'm 35 now. I started masturbating before I'd heard about what it was, probably when I was 11. I'm not sure, maybe it was 10 — but I do remember that I was in bed in the morning before getting up for school, lying on my back and pushing my erection down between my thighs and letting it spring back up. I found that this felt really good, and I'd just lie there for several minutes, doing it over and over until the feeling got too intense and I'd stop. I had been doing it every morning for a couple of weeks, always stopping before having an orgasm (not that I knew what one was at the time.) But one day I decided to just keep going, even when the feeling got so intense I felt I could barely stand it, and I suddenly orgasmed for the fist time. I wasn't ejaculating then, but that first orgasm felt so great, I was hooked. After that, I'd do it every day before I had to get up, and in bed before falling asleep at night.
I masturbated regularly this way for the next year or so and began to ejaculate. By the time that happened, I had heard about masturbation at school in sex ed and from friends, so it wasn't a surprise. I discovered, however, that I should have done a better job of cleaning up the evidence after my sessions, because I remember my mother giving me an old towel one night before I went to bed and telling me to put it underneath me when I played with myself because I was staining the sheets! She then told me just to throw it in the hamper at the end of the week and she'd wash it. I was so stunned I didn't know what to say, but she just smiled and said everyone does it "at your age" and to "have fun." I was embarrassed, but it didn't stop me from going ahead and masturbating before falling asleep that night.
There was never much talk about masturbation among my friends at this age, 12 and 13. I just assumed all my friends did it, too. I had found my father's extensive collection of National Geographic magazines a rich source of stimulating material, and after school if no one was home, I'd often take a few favorite issues and masturbate to the pictures of naked women and girls. About this time a friend of mine gave me a couple of Playboy magazines he had gotten from his older brother after he had "seen them enough"; I had a couple of favorite women in there that I masturbated to many times. But most of my masturbation was without any external stimulation, just lying in bed in the dark and gently bringing myself to orgasm, just concentrating on what I was doing.
About this time, a friend of mine came over after school one day, and when we were up in my room just goofing off, he asked me if I had any Playboys. I hauled out my stash, and we sat down on the floor and looked through them for a couple of minutes, and he asked me if I wanted to masturbate. I was surprised but certainly willing, so we stripped off our clothes and sat down next to each other on the floor. He used the "fist" method and was really surprised by the way I did it as I lay down and started pushing my penis between my legs. He tried to do it the same way, but his penis just wouldn't go down far enough for it to work for him. We briefly handled each other's penises, more out of curiosity than anything else, since I was cut and he was not, and I was a little older and more developed than he was, so my penis was larger. We then both lay next to each other and masturbated ourselves to orgasm.
Other than that one time, I haven't masturbated with another guy. I had a few opportunities during the next several years, but for one reason or another, I felt too uncomfortable about it and declined to pursue them. For the next few years, I continued to masturbate between my thighs, but I did discover hand lotion and started using it in my bed. Again, I guess I wasn't paying enough attention, because my mother came back from the store one day and handed me a bottle and told me to just keep it in my room. I often felt a little uncomfortable knowing that my parents, and maybe even my little sister (who was about 10) probably knew exactly what I was doing in my room in the morning and when I went to sleep at night, and for a while I tried to stop masturbating when they were at home. But since I'd started high school I wasn't getting home until dinnertime now, and I quickly abandoned that idea because I'd be able to masturbate only on the weekends, if everyone else was out — so I just closed my door and tried to do it as quietly as I could.
When I was about 15, I started trying different ways to masturbate. I got started on this by accident, trying to masturbate in my regular way while lying in my bean-bag chair. I rolled over on my stomach after I'd had an orgasm and found the chair was nice and slippery when I rubbed against it. The next day, I climbed on the bean bag and "humped" it until I had an orgasm. For the next couple of weeks afterward, I mounted just about everything I could think of: pillows, cushions, my bed, the couch. I even took my little sister's giant stuffed bear and humped it on my bed, missionary style. All of this was really fun, but I didn't do it for long because I was afraid of leaving tell-tale signs of my escapades throughout the house, so I just settled on my bean-bag chair for humping.
I was a virgin at this time, and very curious about what it would feel like to be inside a vagina — so after my brief humping frenzy, I started looking about for something that I could actually put my penis into. The first object I found was a heavy crystal stem vase of my mother's, which appeared to be of just the right inside diameter. I took it up to my room a couple of days later when no one was home, applied some lotion to myself, and with the vase placed between two pillows on my bed (and being careful because it was glass), I gently but successfully copulated with it. I really enjoyed this new method, but soon I found there just weren't that many things around the house that were any good for having "sex" with. I did find a couple of jars and small bottles with mouths wide enough to let me enter them and snug enough to feel good, but they were even more fragile than the vase — and while they did work, I didn't find the experiences worth repeating. I tried toilet-paper and paper-towel rolls, but they were too tight and tore and unraveled before I could get anywhere with them. What I did find that worked, and what I used for the next couple of years when I wanted to be "inside" something, was simply a magazine rolled up into a tube. I realized I could make it just the diameter I needed; I would tape the roll together, put some lotion inside it, put it between a couple of pillows on my bed or between my mattress and box spring, and have "sex" with it. Shortly before I left for college, I discovered that I could just use my hand in the "vagina" method, and then quickly moved on the "fist" method. I realized I could control the sensations I was giving myself much more easily and increase the time before I'd orgasm. It was also much easier and more discreet than the methods I had been using, and I devoted myself to this obvious but then-unknown-to-me method.
When I was a freshman in college, I continued to masturbate a couple of times a day, but I often found myself without any privacy and was often unable to masturbate for a couple of days at a time. Although I shared a room during my freshman year, I never saw my roommate masturbate, and I never masturbated when he was in the room. I'm sure he was doing it, too, but we just never talked about it. After my freshman year, I had what was called a two-room double, or a suite of rooms with friends, so privacy wasn't an issue. I did get interrupted on several occasions, but not really "caught." One of my roommates and I would share our porn stashes with each other, so we both knew the other was masturbating, too — but again, we never really talked about it much. What I did begin to do when I was in college and had my own room, and what I have done ever since, was to focus on fantasizing while I masturbated at night and stretch my sessions out as long as I could. I often masturbatied slowly for a half hour or an hour before bringing myself to orgasm. This was a real change from masturbating when I was a teenager, when I just focused on the sensations I was getting and when 15 minutes would have been a really long time before reaching orgasm. Another thing I discovered in college was that masturbating was a great stress reliever. I would often break during an all-nighter or when studying for finals to relieve my tension through masturbation.
After college I went to graduate school and then started working. I shared apartments with several friends and continued to masturbate once or twice or day in the privacy of my room. Most of my roommates and I never really talked about it; one apartment-mate friend and I would share our porn stashes, but we would always masturbate by ourselves. We did talk about masturbation a couple of times, and we shared our techniques and talked about different places we'd done it, and whether we ever did it with another guy, which we both had when we were kids. Neither of us apparently had any desire to masturbate with each other, and that particular topic never came up. I also did have one female friend with whom I wasn't sexually involved whom I talked with about sex and masturbation, and we even told each other how many different ways we'd done it.
After living with roommates for several years, I have since had my own place and have enjoyed being able to masturbate whenever the desire or the need has struck. I often now do it in the shower in the morning before work, either standing and using my hands or lying in the tub and using the detachable shower massage. My other most common masturbation time is still before bed, either in bed or on my couch, using my hands. I really enjoy having the chance to masturbate for as long as I want, when I want. I've also gone back to using some of the other methods I used when I was a teenager, and I've gotten into experimenting again. I have a few different ways to do it that I've liked and use now and then for variety, some of which I saw here on JackinWorld when I discovered the site a couple of years ago.
As for masturbation and relationships, I had begun dating and lost my virginity in college, and I've been sexually active since — but being sexually active never seemed to diminish my desire to masturbate. If anything, it seemed to increase it. I have found that most of the women I've dated or been involved with have not really had an issue with masturbation: They do it themselves, although most haven't wanted to talk about it very much. They know I do it, and it never seems to bother them. One woman and I often had phone sex, although we masturbated in front of each other only once. But I also dated a couple of women who were offended by the idea that I would masturbate when I could have sex with them, but both of these relationships didn't work out for other reasons. Overall, I think I have a pretty healthy attitude about masturbation. I enjoy it greatly and expect to be doing it for as long as I can.