Pegging describes a sexual practice by which a man is anally penetrated by a woman wearing a strap-on dildo.

The origin of the neologism was a winning entry in a June 21, 2001, contest in Dan Savage's Savage Love sex advice column. In the column, it was a specifically heterosexual term; the competition was held after an observation was made that there was no common name for the practice of females penetrating heterosexual men with a dildo. Because the term is quite new, many people use different terms for "pegging", such as "bend over boyfriend" (commonly shortened to BOB) from the popular video series of the same title.

The act of pegging can be enjoyable for both partners: men may find stimulation of the anus, rectum, and adjacent organs, particularly the prostate, enjoyable provided that enough lubricant is used, and women may get direct stimulation from the dildo, from its base, from vaginal or anal "plugs", or in the case of a form of double-ended dildo, from vaginal penetration on the other end. Additionally, a woman could use a secondary vibrator, between the dildo and her clitoris, to get pleasure from pegging. Some men and women may also find pleasure in the psychological aspects of submitting and dominating, respectively, though as BDSM practitioners might point out, the act of being penetrated is not necessarily experienced as a submissive act, nor is the act of penetrating always experienced as a dominant act.

Given the stigma associated with anal sex (and its association with male homosexuality), some people, many of them heterosexual, derive enjoyment from the taboo or gender-transgressive aspects of pegging. Some females may enjoy the feeling of having a "simulated penis," while some men enjoy the experience of receptive penetration.