When I was twelve (maybe thirteen) I inadvertently discovered the joys of jacking off. I think I woke up in the middle of a wet dream, turned myself on to my belly, and finished myself off. My brother then began to complain about hearing my bed frame squeaking (we shared a room, and thank goodness at that time my dad has taken down the bunk beds). Since then, I don't think I have missed a day, though I have changed my position to the most popular one. In fact, the day I wake up without a morning woody, I know the Angel of Death is just around the corner, and I won't change my name to deceive him (old Jewish bubby's tale).
One interesting book in the Bijou archives called The Gay Book of Lists by Leigh Rutledge enumerates some jack off positions in some detail, also helpfully guiding the potential wanker offer to their specific advantages and disadvantages:
“Lying on Back” is the most popular (illustrated by Tom Cruise in the movie Risky Business); advantages include a good angle for thrusting actions with the hips; the sheets don't get messy; easy reach for either tit. Disadvantages include it can be a bad angle for pictures (well, with these new-fangled cameras on phones, perhaps not) and it can become monotonous when done day after day (Maybe one could do it while lying on one's back in the bathtub; I tried it once, but I became so relaxed because I was lying in water not much happened; maybe I should have done it in a dry tub, but that would have been uncomfortable.)
“Standing Up” is also popular, especially for those who cruise public bathrooms and want to show off (I would add especially if one is a grower). An advantage especially for those who are narcissistic: one can look at oneself in the mirror. It is also easy to do anywhere. Disadvantages include tired knees and legs, cum-splotched footwear, and it can be difficult to keep a dildo in the ass.
“Legs Thrown Over Head” is a position where a guy lies on his back and throws his legs back over his head so that the head of his dick is aimed right at his mouth. This position is often used in BDSM scenes as a way for the master to force his slave to eat his own cum. Advantages include an intense orgasm; one can satisfy a hunger for cum; and one can watch oneself jack off. Disadvantages include a sprained neck and back (yikes!) and eyes filled with cum.
“On The Belly, Rubbing Dick Against Sheets, Pillows, Etc.” is quite fun and sensual, especially if one is in a lazy mood, and it also works while one is being fucked up the ass. Disadvantages include messy sheets and also, as I mentioned in the first paragraph, don't do this if one's bed squeaks a lot and one's roommate is in the room supposedly sleeping (unless he wants to join in).
"Sitting on Toilet” is excellent if one can't find any other way to be alone and clean-up is quite easy. In fact, Portnoy, among others, helped make this position famous, and it became almost iconic in the movie The Right Stuff. More recently, based on craiglist missed connection postings, this seems to be going in men's room stalls everywhere, so perhaps for many it's not a distasteful location to pull the pud.
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