Pegging is anal penetration of a person with a penis by a partner wearing a strap-on dildo. The word grew from advice columns and then went mainstream enough to show up in ordinary conversations, usually with a joke attached. The act itself is just anal sex with a harness.

Prostate stimulation is a frequent motive and not the only one. Power, novelty, and the look of the harness all play. Warmup, lube, and a flared base on the toy still apply. The harness should not bruise the wearer while they try to aim.

Talk about depth before anyone is proud of their hips. A dildo does not have a built-in wince. The receiving partner’s voice is the sensor.

If the joke around the act is covering contempt for the receiving partner, skip the act until the contempt is gone.