Whether you're a gay newbie venturing into penetrative sex for the first time or an old pro, topping can be tricky and painful if done wrong. But with a little planning, practice, and plenty of communication and consent, you can master this sexual position without too much hurting.
While the terms top, bottom, and vers have traditionally been used to describe sexual positions and power dynamics in queer sex, that binary system may not work for everyone. There are many ways to enjoy penetration, and it's important to be flexible and communicate about your partner's preferences, says Carly S. "Topping can be a lot of fun," she says. "It's all about giving pleasure to whoever is on the receiving end."
Be patient and gentle, especially at first. The spinchter (bottom's ass) is naturally tight and closed, so you need to warm it up slowly and gently before introducing any penetration techniques. For example, you might start by stroking, rubbing, and kissing the cock. Then you can get more aggressive with the oral sex and, eventually, with the dildo.
Once you've reached orgasm, it's not your job to rush out after the bottom ejaculates; in fact, it's probably best if you stay and help him finish, either with more kissing, stroking, sucking, fingering, or porn. Just remember that he needs to be able to breathe and have his own orgasm, too! And don't worry if he doesn't immediately reach orgasm after you've thrust in him—this can depend on his anatomy and how sensitive it is to being touched.