If you are touching him and paying attention to his response, he will guide you. If he says something feels good, trust him. Beyond that, I have nine tips that guys have confided in me. I hope they help you expand your hand job repertoire.
Draw It Out
Start slow. Very slow. Touch him through his pants, using nice, long strokes. Touch his inner thighs. Stop and kiss for a few moments. Work him into a frenzy.
Lube Up
Try using lube, lots of lube and different kinds of lube. I recommend trying water-based lube and silicone lube. They each have a very different consistency. Let him decide which he prefers.
Play Show and Tell
Ask him to show you how he likes to be touched. Watch what he does and learn from him. This can be a really lovely and intimate exchange or it can be as explicit and dirty as you want it to be. It’s all about your personalities. If he is too shy to show you how he touches himself, put your hand on his penis and put his hand over your hand while you ask him to guide your touch.
Learn New Techniques
There are lots of ways you can use your hands. Some of the most recommended techniques may feel awkward or ridiculous to you but bring great pleasure to others. You just need to explore. Try a style I call "dumping out the glass of water." Pump his shaft from bottom to tip. As you reach the tip of his penis, flip your hand over like you are dumping out a glass of water. Then bring your hand back down to the base of his penis. Bring it back up and flip your hand right-side-up again at the tip. In doing so, your whole hand engulfs the head of his cock incorporating it into the hand job. Most men love this technique.
Use Two Hands
You can use both of them on his shaft, or let one hand travel, cupping his, balls or putting pressure on his perineum. You might also try to hold the base very firmly with your thumb and index finger together to create a ring, and then use your other hand to pump his shaft.
Play With Your Position
You can be in a position of power by getting between his legs, standing over him while he is sitting, remaining completely clothed while he is naked, putting a blindfold on him, touching him under the table at a restaurant, or have him on his hands and knees while you reach around and take his orgasm. You can be in a submissive position where he stands over you while you are on your knees. My point is, you can play with power with any sex act, including hand jobs.
Pay Attention
Feel his response. Watch his body. Listen to his breath. Look for facial expressions, changes in muscle tension, shivers, goose bumps, arching back, how tightly he holds on to you, or curling toes. Listen for sighs, moans, groans, and words. You can also ask him yes or no questions to find out if what you are doing feels good, if he would like it faster, slower, more pressure, less pressure, and so on. When you are done playing, ask him what worked. This can give you insight and be a fun way for him to reinforce what he loves.
Take It All the Way
One thing guys frequently tell me is that when they give themselves hand jobs and they are about to orgasm, they will make sure to keep their hand on their shaft and moving until the orgasm is complete. These last five or six strokes can be some of the most satisfying ones, but women tend to let go before their partners have fully ejaculated.
Get to Know His Anatomy
Our bodies are really very simple and beautiful. Read my book, Sex with the Lights On: 200 Illuminating Sex Questions Answered and develop a deeper understanding of pleasure anatomy, yours and his. Keep in mind that if he has his foreskin, the experience of a hand job may differ. Check out Sex and Circumcision for more tips.
Also...
Whenever I talk about pleasure I like to make it clear that I am painting in broad strokes. Every person is so unique in their sexual response. Your partner can veto anything I say. He is unique in his size, shape, response, and vascular and nerve structure. So, the very best way to know how to please him is to ask him.
