Although I'm turned on by reading all these exciting stories, mine may seem a little tame by comparison, but I do fondly remember my 'best' jerk off memory, and often wish I could relive it.
Growing up, I was typically tall for my age, and a little chubby, but I did a lot of sports, so I was in decent shape and somewhat flexible with all the constant stretching and exercises. As a teenager, I was horny as fuck, but between school (all boys Catholic high school), homework, sports, commuting, and church (and lacking a car), I didn't have much opportunity to meet girls, no matter how horny I was. I remember being awake after midnight, just horny as hell, stroking my member, fantasizing that some gorgeous babe would crawl through my window at night and my parents would be away (since my bedroom was next to theirs, and my bed was against the common wall). I had had a stash of a few girly mags, Playboys, Penthouses, Hustlers (this was before the internet (as we know it) or the world wide web). Sometimes, if my parents were out and I was alone, I'd sneak into my parents' bedroom and look for hidden mags my dad occasionally kept. Usually it was a somewhat tame Playboy, the first one I ever found I was in third grade and I found a 20th anniversary issue (two bunnies on the cover with a black background) snuck into one of the pockets of his business briefcase. One of the best memories was finding my first hardcore mag under my dad's mattress. It looked like it was from the late sixties or early seventies... It had a color cover and the last half was color but the first half was black and white. It was about this guy living in a boat watching these two girls (one in a black bikini, the other in white) sunbathing on the adjacent boat. Sure enough, while applying suntan lotion on each other, they start 'exploring' each other. The first picture I saw of any penetration was one girl inserting her single finger into her friend's pussy. After watching them finish sunbathing, he goes over, introduces himself, and invites them over for drinks, which of course ends up in a threesome. The guy was in good shape, blonde, but middle-aged and balding... The girls were young (college aged), thin and cute, not flat chested (Thank God, not into that), but not particularly stacked (which I was developing a taste for)... Both about a C-cup, one a mid-C, the other barely a C, maybe a B. My dad obviously either hid it better or threw it away, but I only saw it a few times before it was gone. The cover was framed in yellow and green, and I believe the title was in yellow, and stylized... The first letter had one or two loops, so I thought it was titled "Just Aloat", but after thinking about it and seeing similar letters, I realized the title was actually "Lust Afloat", and I've been looking for a copy or scan of this magazine for decades. Between that and hiding one or two of my girly mags in one of our bathrooms (one of the few places I had privacy), I'd be stroking on the toilet or in the shower. Despite my self-induced blue balls from all the constant stroking/edging, it wasn't until I was 14 that I finally came, for the first time, in the shower. Since I was in pretty decent shape and flexible, despite being slightly chubby, I was curious about what it'd be like to have a blowjob (or maybe even give one)... Even to this day I've fantasized about it, but never have... I love women, and am not even remotely interested is guys as anything other than friends, but there's something about seeing an engorged, throbbing cock, and full, low hanging balls that gets me excited, especially seeing those veins popping and precum dribbling from the tip before a torrent, a fountain of cum jets forth. Being young and in shape, my cock was ~7-9 inches, depending upon how you measured it (from my balls or my stomach), and thick, but not Blake Palmer thick/girth. Sometimes I'd make sure the door was closed, get in the hot shower and lay in the tub, stroking... One day I decided to turn around with my head under the faucet and feet against the back... I noticed that it felt slightly different and I could see my cock slightly better... I began to wonder so I tried something different... I began to scoot my ass up the tub with my feet on the back wall... Soon my head was still on the bottom of the tub, my back against the back of the tub and the back wall, and my feet high on the wall... I had a much better view of my cock, now, but it was in an awkward position... But it was about to get more awkward... I lifted my legs (or, better described, let them fall) over my head... Where I was facing my own cock... Given the position, I wasn't exactly positioned to stroke myself, and it was difficult to breathe, but it was exciting... My cock was engorged, although at a strange angle, and with effort I was able to just barely get the tip to my lips... I couldn't quite get it fully in my mouth, but I do remember tasting my own precum and once or twice sucking out some of my own come... Sometimes I wondered what it would be like to be sucking my own cock, in that position while having some babe licking my balls or even some guy burying his cock in my ass. Unfortunately, I could never take too long exploring this position, because, inevitably my father would bang on the bathroom door (or even unlock it and come in) getting made at me for taking such long showers and using all the hot water (as if he didn't know that I was jerking off). After being in the military and going off to college, I kept the same diet, but my metabolism slowed as I got older, spending more time sitting, attending lectures, studying, playing computer games. I got chubbier and fatter... And, unfortunately, less flexible and a fatter stomach and less cock pas my fat. I'm starting to lose weight again, but nowhere near what I was when I was still able to put my cock between my lips. I remember decades later, my wife got me watching this U.S.A. network show about these two plastic surgeons that were in business together (friends? brothers? ... It's been so long ago), called "Nip/Tuck". One is an ethical surgeon who occasionally does pro bono surgeries for disfigurement, and typically does surgeries to help those needing some quality of life help, while the other is the most base, crass horn dog who specializes in vanity surgeries and goes through girlfriends every episode, nothing more than boob jobs, face lifts, liposuction, implants, penis extensions, etc. I remember there was a few episodes where the crass one heard about a client (?) who had such a unit he could suck his own cock... I don't know if he did it the same way, but... The crass doctor, who was in decent shape, but older (40's?) and obviously not as flexible, tried it himself, unsuccessfully, and ended up with a neck injury, having to wear a neck brace for at least an episode or two.
I do miss that, and sometimes wish I could do it again... But I know that I'm out of shape, not nearly as flexible, and just too fat to seriously consider that... although I am losing weight, so, who knows... if I lose enough weight with diet and exercise, and enough stretching to improve my flexibility, maybe... just maybe... I love my beautiful, busty BBW wife, but her libido is practically dead (at least around me), and it's frustrating, as half the time I see her walking around and I just want to run over, rip her clothes off and ravage her until she can't cum anymore...
Sorry it it was vanilla, but just thought that I'd share...