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 or dictionary definition for the act in the English language.
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 especially the prostate, pleasurable. 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. Triple-ended dildos provide both vaginal and anal stimulation of the female partner.
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), Based on a series of lectures and workshops by Robert Lawrence and Carol Queen and co-produced by Fatale Media, Inc. The movie was 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 "BOBing" 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 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.
Since 2011, the sex educator by the screen name of Ruby Ryder has been running a blog and podcast entitled Pegging Paradise. As of October 2016, the podcast has over 140 episodes. She also runs the instructional site Pegging: 101 which is especially targeting those interested in pegging with no interests in the association with BSDM.
The first pegging scene in film (long before the term was coined) appears to have been in the 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 1976 pornographic film The Opening of Misty Beethoven.
Female-to-male strap-on pornography became a popular subgenre in the early 21st century, with a number of studios producing dedicated series about it. Pegging films include Strap It On, Babes Ballin Boys, Strap Attack, Strap-on Chicks, Boss Bitches, various films produced by LEDA Studios, as well as San Francisco-based BDSM themed website Men In Pain. Several hundred exclusively pegging films were produced, as well as twice as many bisexual and straight films with strap-on scenes.
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?"
In popular culture
While not necessarily referred to as "pegging," the following popular culture works make reference at least to the concept.