This is the story of how I first really paid attention to how an orgasm feels, rather than just enjoying the feeling.
Some time ago jackinworld.com had as it's question of the week 'what does an orgasm feel like to you?' I had been masturbating since I was a little kid (around 6 years old), and thought 'What a stupid question.' But when I thought about it, I couldn't describe what an orgasm felt like. Yeah, it felt good, but I couldn't remember noticing the details. I had always been caught up in the sensations that they just happened.
So I set out to try to concentrate on it so I could describe it, and found it very hard to think logically enough while in the act to remember details, other than I knew my penis pulsed, semen came out, and it felt really, really, good.
I first noticed that in my preparatory stages, I like to get rid of my underwear, though my situation makes it seldom that I can get completely naked at my computer to do it. I'll take off my underwear and freeball it for an hour or two before I start, and it feels good. Gets me in the mood. I like the feeling of my penis rubbing against the inside of my pants without the interference of underwear.
When I was a kid I did it outside a lot. I would find a place in the woods where I knew no one would see me, strip down, and play nude for a while before jacking off.
Now when I first sit down to start, I'll just caress my penis lightly through my pants, getting a half-hardon which I'll rub around. My penis head rubs against the fabric, and my fingers lightly grip below the head, and soon the sensations can be felt all around my groin. When I get going, I'll pull down my zipper and pull my penis out. It isn't big; about 5 inches. I don't fist it like I thought I did; mostly I use my finger tips around the upper shaft, just below the head. The most senstive spot is the bump under the head where the remains of my frenulum is (I'm circumcised, unfortunately -- the remains of the frenulum feel so good to the touch that I can't imagine what it would feel like if it were all there). I'll do that for a long time while reading stories on the internet. I'll get the urgent feeling of impending orgasm, then stop for a minute to calm down.
I normally use lube (Astroglide or WalMart's generic version of the same thing, Equate personal lubricant), but don't put it on until the final stages. It feels so good once I do that I can't hold out much longer before going all the way to orgasm. When I'm really feeling sensitive and am ready to surrender, I squirt a few drops onto the head of my penis and rub it around. That feels really good, but I feel compelled to move down to the ring just below the head where I fingered earlier. I encircle my penis there with my finger tips, and alternately rub up and down and around, mostly stimulating the sensitive frenulum (until I took the effort to pay close attention, I didn't know I did this -- all I knew is that I rubbed my penis where it felt good). When I get closer, I gently use my thumb and forefinger to rub up and down the shaft very gently, at the top hitting my frenlulum, at the bottom going about halfway down the shaft. I usually have to put a few more drops of lube on at this point. After a while I take my next finger (the middle one) and place that on the bottom half of the shaft, so my forefinger is on my frenulum and middle finger rubbing the bottom half of the shaft, and the thumb on the top rubbing the top half. I'll rub all three in circluar motions (I always thought I jerked up and down, but I don't; isn't that interesting? It is to me).
When I'm within a minute or so of cumming, I'll form an 'O' with my thumb and forefinger, and very gently go up and down, from the bottom of my shaft to the head, stimulating my entire penis. I go as slowly as I can for as long as I can, and as the first throb is about to hit, I grip harder, and feel the first pulse. Here comes the biggest surprise. Not only is the first pulse dry, but the second and third are, too. I guess it's like priming a pump. I always thought I started ejaculating right away when the climax hit, but the first three, most pleasurable, throbs are dry. It isn't until the fourth that semen comes out. Usually the first shot is kind of a dribble, then I get three rapid pulses which shoot small jets. If I've been able to work myself up to a highly aroused state, I can actually feel the semen being pushed up the tube in my penis. It feels so good!
I've been known to shoot over my head when really turned on, but usually I shoot to my stomach. After the three jets, I usuallykeep throbbing rapidly several more times, with semen mostly dribbling out the end of my penis, not shooting. Then the rapid pulses stop, followed by several small, slow, throbs over about a minute where nothing comes out, but it still feels good. This is when I milk my penis to get all the remaining semen out.
I keep holding my sensitive penis for two or three minutes before letting go. By then it is soft, and I wipe up the mess. I feel very tired afterwards, and often will lay down for a short nap if I can. I feel very relaxed and satisfied.
So, that's what I've learned about my own orgasms. Very different than I thought.