Pegging is a sexual practice in which a woman performs anal sex on a man by penetrating the man’s anus with a strap-on dildo. The neologism “pegging” was popularized when it became the winning entry in a contest in Dan Savage’s “Savage Love” sex advice column, held after an observation was made that there was no common name for the act.
In terms of physical pleasure, a woman’s genitals may get direct stimulation from the base of the dildo, or in the case of a double-ended dildo, from vaginal (or internal) penetration. A woman can use a secondary vibrator, between the dildo and her genitals, to get pleasure from pegging. Men may find stimulation of the anus, rectum, and adjacent organs enjoyable. During anal sex, male pleasure can be particularly derived from the prostate, which can lead to an orgasm and ejaculation. Some men enjoy masturbating (or being manually stimulated) during pegging.
Advice columnist Dan Savage wrote that he believes all men should try pegging at least once, as it may introduce them to a new enjoyable sexual activity and illuminate them to the receiver’s perspective in sex.
A few instructional movies and books have emerged in recent years, including Bend Over Boyfriend (1998), co-produced by Fatale Media, Inc., and created and directed by Shar Rednour and Jackie Strano, SIR Video Movies co-founders. Bend Over Boyfriend originally inspired Dan Savage to call the act ‘BOB’ but his readers subsequently voted on the winning term, pegging.
American pornographic film director and sex educator Tristan Taormino released an instructional pegging movie in 2009 by Vivid Entertainment Studio, Tristan Taormino’s Expert Guide to Anal Pleasure for Men, featuring a detailed explanation about male anal pleasure and strap-on dildo sex. In it, she teaches a workshop with instructions and skills for safe and pleasurable female on male anal sex. There are three scenes, in which pairs of pornographic actors explore different sexual devices and positions for pegging.
As an accomplished author of numerous sex guides and informational books on various sexual taboos, Violet Blue wrote and released The Adventurous Couple’s Guide to Strap-On Sex in 2007.
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, based on the novel of the same name by Gore Vidal, although it was not explicit. The first explicit pegging scene is believed to have been in the 1975 pornographic film The Opening of Misty Beethoven. There is a depiction of pegging in the 1959 novel Naked Lunch by William Burroughs. The dildo used in the scene is called a Steely Dan III, and is the source from which the musical group Steely Dan takes its name.
Female-to-male strap-on pornography became a popular sub-genre in the United States in the early 21st century, with a number of studios producing dedicated series about it. Pegging films include Strap It On (black women on white men), Babes Balling Boys (with sixteen editions), Strap Attack, Strap-on Sirenz, Strap-on Chicks, Boss Bitches (with over two dozen editions), various movies produced by LEDA Studios, and San Francisco-based Men In Pain. Several hundred exclusively pegging films were produced, as well as twice as many bisexual and straight films with strap-on scenes.
Well-known female porn stars who expressed their pleasure in pegging their male partners include Taylor Wane, Debi Diamond, Brittany Andrews, and Monique Covét. When questioned about her particular kink Covét replied, “If we women have to take it from behind, then why not a man?”