A woman pegging a man doggy-style with a 4-strap harness and dildo, using the corner of the bed to adjust the height to that most comfortable for penetration

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" from the popular video series.

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 women may enjoy the feeling of having a "simulated penis," while some males enjoy the experience of receptive penetration.

Pegging has recently been featured in a number of pornographic movies; the first pegging scene (long before the term was developed) appears to have been in the non-pornographic 1970 film Myra Breckinridge, although it was not explicit. The first such explicit scene is believed to have occurred in the 1976 film The Opening of Misty Beethoven. A few instructional movies and books have emerged in recent years, including Bend Over Boyfriend, produced by sex educator Carol Queen.

In the 21st century, female-to-male strap-on pornography has suddenly become a flourishing industry in the U.S., with such a high market value that a number of studios focused primarily on this subject started producing dedicated series about it. The most notable ones are Strap It On (black women on white men), Babes Balling Boys, which had six editions, Strap-on Sirenz, Strap-on Chicks, various movies produced by LEDA Studios, and San Francisco-based Men In Pain. It is unclear what triggered the increasing popularity of this genre.

Well-known female porn stars who have professed a fondness for pegging include Taylor Wane, Brittany Andrews, Mika Tan, and Monique Covét. When questioned about her particular kink Monique Covét memorably replied, "If we women have to take it from behind, then why not a man?"