First step: Stop thinking of it as a job. Done correctly, oral sex can be satisfying for both of you.
For established partners, oral sex “can be one of the most empowering things to do because you’re taking charge of his pleasure,” say Mark Michaels and Patricia Johnson, authors of Bedded Bliss. “That can amp up your own arousal.” It’s also a time to be exploratory, playful, and fun. With that in mind, do what feels best for you—and by all means request that he return the favor. Once you’re ready, start slowly and maintain eye contact as you begin to move your hand up and down his shaft. If you’d like, prep the area by adding a bit of flavored lube that’s safe for consumption, like Babeland’s Babelicious line, which can make the act a little more palatable and help any initial hand actions go more smoothly.
Let yourself linger
Nothing about a blowjob should be fast—he wants to savor it, and you’ll love making him squirm. So start slow by grazing your mouth against his penis as you continue moving your hand up and down his lubricated shaft. One more thing: At this point, it’s all right if he’s not entirely erect. In fact, it’s normal for his erection to ebb and flow during oral sex, and it’s not indicative of his pleasure, says Amy Marsh, a Berkeley, CA-based sexologist. Take his temperature now and again by asking him to give you a clue when a move really turns him on. The dirty talk adds to the mood,and it’ll make the next time even better. “Being honest about how it feels will boost enjoyment on both sides,” says Marsh.
Take it an inch at a time
The deeper, the better may be the case in porn, but not so in real life. “Gagging takes you both out of the moment, and you and he will enjoy oral sex much more when you’re both having fun,” says Marsh. To simulate deep throating, you want to use some combination of your mouth, tongue and hands. Marsh recommends a tight grip on the base of his shaft. Then wrap your mouth just a bit below the frenulum (the place where the head of the penis connects to the shaft) so your lips meet your fist, and move your mouth and hand in a rhythmic motion. Always let him know what you don’t like when you’re going down on him, whether it be holding your head or thrusting strongly.
Pay lip service
Awkward angles and jaw pain can make it hard to enjoy oral sex, so take some breaks. You could try the “lipstick technique” for a bit: Use your hand to brush the head of his penis against the outline of your lips, taking the head in your mouth between outlines for added lubrication.