I wrote a rambling introduction to the topic of Handjobs here, and part one of this instructional bit is here.
Pressure:
Ask him, for god’s sake! It’s his penis, he’ll know. This isn’t your ex-lover’s cock, or your high-school boyfriend’s cock, or your college fuck-buddy’s cock. This is his cock, and it feels differently about things than those other dicks did. If you ask, he will think you value making him feel good. It’s a smart way to go. Let him tell you. He’ll be glad you asked. Not all guys are comfortable telling you when it’s too hard, and some men will even endure pain to avoid offending you. Be a real woman, and ask.
Lube:
Covered this before. Most guys’ll say it needs it. If you want to avoid clean up and have better grip, you can put a condom on him. Start with oral and even end with oral, but it doesn’t need to be only one or the other. When it comes to using lube, start with only a little, and increase the quantity as needed. Too much will compromise your control.
Positioning:
It doesn’t “really” matter. He should be comfortable, and reclining or lying down is a good thing for him. I like to begin by lying down next to him, or snuggling up, whatever, and typically begin with oral if I’m in the mood (see below) and then will sit up by his waist when I’m making progress and getting serious about the work. This gives you use of both hands, and more flexible access to all his parts, but begins with greater intimacy.
The Moves:
First off, every single one of these moves changes according to pressure and speed. Doing it nice and gentle will give him one set of feelings, but picking up the pace and gently increasing pressure as you go will take him to a whole new galaxy of feelings. Speed up, slow down, speed up, slow down. When you’re wanting to finish him off, pick the move you’ve seen the best reaction to, and just go to town. Once he comes, he’s going to get super-sensitive super-fast, and when he says stop, STOP. If you like, after a couple minutes, when he’s resting, you can just rest a hand on his cock, as if to say it was good for you, too. Or you can go have the beer you’ve earned. Whatever. 😉
Starting out, just play with everything. Caress his balls, place your open, flat hand over the length of his member and begin doing gentle-pressure circles over the whole region. Play with the tip of his penis, whatever you like. Better yet, take his soft-ish cock into your mouth, or nibble it with your lips, or lick it with varying degrees of pressure.
Then, once it’s harder…
The Ring-a-Ding-Dink:
For this, you make a “ring” of your index finger and thumb, or use the middle finger if he’s got greater girth, and wrap it around the base of his penis. Start tugging up and down, with firm pressure, but slowly, just around the base. So, this move has about a 1” rise on it. You’re not ascending the whole shaft, just staying right there at the base of the penis. Do it with more pressure and faster, and you’ll see him responding. A lot of nerve endings are at the base of the cock, hence why guys love penetrating you deep and hard, so it fires up those basal nerves. This is a great one to use during oral, too, while you have your mouth on his shaft’s head, and toy with it using your tongue to flick and lick around the head.
The Piston:
Standard move, girlies. But not, and I repeat not, a go-to move, not in my book. It’s a transitional thing. If he wants a piston job, let him do it later, and you know he will. Do a little piston work here and there, particularly when you’re wanting to move towards taking him to orgasm, so you can indicate speed’s about to pick up. This move’s just basically you wrapping your hand around the shaft and going up and down, from the base to the tip. If you’re using proper lube or a condom, it’ll make it easier to do full moves that take your hand up, over the penis’ tip, aka the “glans” or head. The head region’s crazy sensitive, so doing the piston via ascending over the head will be pretty hot for your man.
The Tweaker:
With both your hands around his penis (like you have them wrapped around the top of your steering wheel; your thumbs will be next to each other), you want to rotate your hands in opposite directions. One’s rotating towards you, the other’s rotating away from you. This gives him a pretty wicked set of feelings, and this move’s got a lot you can do to vary it. Such as:

• Stop rotating the hand by the shaft, instead, start pumping a bit, like you would with a stress ball, or if you were checking your blood pressure at the doctor’s, squeezing that rubber bulb. Now and then, just squeeze firmly. All the while, the hand wrapped around the top of the shaft continues what it’s doing.
• Or… Continue rotating around the shaft area, but flip your head-hand around, so your palm’s facing you and your thumb’s up at the top of his penis. Now your thumb can play with the head. This hand now does a mini-piston, while you rub and tease his glans at the same time. (So you have both the rotating and piston action at the same time.)

Knob-Polisher:
This is a fun one to do, and needs either a well-lubed condom or lots of lube on your hands. One hand’s around the shaft, maybe doing a mini-piston, while your other hand is open, with the palm on top of the head of his penis. Press down and do circles. That’s it. It gives him a lot of stimulation through his head. Press firmly, too, and harder as you go faster. Some guys get desensitized a little too quickly at the head of the penis, so you need to be aware of what your man’s tendencies are that way. You can do circular movements or you can do rapid side-to-side movements, but either way, his glans is gonna be happy.
Collision Course:
This is a bit of a mind-fuck, and one he’s virtually guaranteed to love. With your hands again in the “steering wheel” position mentioned above, you’re doing “opposite” pistons. Meaning, you’re doing the piston move, but your hands will be colliding – one’s going up from the bottom of the shaft, and the other’s coming down from the head. This goes against what his penis has been conditioned to feeling, so it’s a pretty wild departure. You can reverse this, so your bottom hand is moving down to the bottom (and emphatically colliding into his public wall, putting lots of pressure against his basal nerves) and the top hand goes up over the head, which it gives a good squeeze to as it does, and then back down. You can also change hand positions a la the second variation of the “Tweaker” above, but still maintain the opposite movements.
The Garden Hose:
This one’s just a nice departure. It’s a softer move, but it should be done reasonably well-paced, and will give him sensation over his entire penis. In between some heavy action, or even starting out, just pretend you’re pulling out a length of garden hose… One hand goes gently up the shaft and off, followed immediately by the other, again and again and again, and as quickly as you can manage. Doesn’t work with a condom, but lube does the trick.
Diversions:
There are many ways to say to a penis, “I like you, you’re cute.” Tracing a finger up the shaft, either at the front or the back, can be fairly arousing. Playing gently with his balls can be lovely. Tickling his cock can be a pleasant shocker in the middle of a handjob, particularly if you have a feather nearby. Leaning down and breathing hotly on his moist cock can also be titillating sometimes.
I think those are all the “A” moves, and I’ll see if I can think of some more on the weekend. These are at least guaranteed to get you some results in the meantime. No promises about any more postings on this topic for now, though. But the point is, get creative. Bring in props, use your mouth, take moments here and there to nibble his thigh or tease his anus, if you’re wanting to prolong the experience. Don’t be afraid or awkward, and talk to him about what he’s liking. The more you see his enjoyment, and the more intense the orgasm you provide, the more you’re going to be enjoying this, too.

DISCLAIMER: I’ve had comments about uncircumcized guys v. circumcized, and the unaltered boys say they need little, if any, lube. Well, being your standard-edition Canadian girl, I’ve only ever met cut penises. They make lovely friends, but I’m sure I’d like there uncut companions, too. Unfortunately, I remain ignorant of more than just their company. So, their penis heads are apparently more sensitive, and lube is less of an issue. Duly noted.