Pegging (sexual practice)
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 2010, the sex educator by the screen name of Ruby Ryder has been running a blog and podcast entitled Pegging Paradise. As of September 2017, the podcast has over 166 episodes. She also runs the instructional site Pegging: 101 which is especially targeting those interested in pegging with no interests in the association with BDSM. 
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.
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.
- The Marquis de Sade describes a pegging act in his 1795 book Philosophy in the Bedroom.
- There is a depiction of pegging in the William S. Burroughs 1959 novel Naked Lunch. 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.
- Pegging was featured in the 2005 series of the UK comedy Peep Show (2005), in a scene where Jeremy (Robert Webb) is pegged by his then girlfriend Michelle (Shelley Blond).
- It was featured in the television show Weeds, during the episode "Crush Girl Love Panic" (2006).
- In the January 2007 pilot episode of Dirt, Lucy Spiller (Courteney Cox) blackmails Prince Tyreese (Rick Fox) with photographs of him being pegged by a prostitute.
- The September 2007 film YPF features a storyline in which a couple who feel their lovemaking has become boring over time, attempt to spice up their sex by trying pegging.
- The theatre company Pack of Others have an entire theatrical performance devoted to "spreading the word about the pleasures of prostate stimulation and strap-on sex". The show has toured nationally and won Best Comedy at the 2008 San Francisco Fringe Festival.
- In the episode "Knockoffs" of TV series Broad City, Abbi Abrams pegs Jeremy Santos.
- In the 2016 movie Deadpool, an R-rated pegging scene was enacted as part of a montage of sexual activity between Wade Wilson and his girlfriend Vanessa Carlysle.
- These three links chronicle how the term pegging came into usage.
- "The male hot spot — Massaging the prostate". Go Ask Alice!. March 28, 2008. Archived from the original on October 10, 2011. Retrieved July 5, 2016.
- Nault, Curran (Summer 2010). "Bend Over Boyfriend to Take it Like a Man: pegging pornography and the queer representation of straight sex". Jump Cut (52). Retrieved July 5, 2016.
- Bridges, Ana J.; Sun, Chyng; Wosnitzer, Robert; Scharrer, Erica; Liberman, Rachael (September 2008). "A comparison of male and female directors in popular pornography: what happens when women are at the helm?". Psychology of Women Quarterly. 32 (3): 312–325. doi:10.1111/j.1471-6402.2008.00439.x.
- Ruby Ryder's Pegging Paradise.
- Pegging: 101
- "Not just another Barbie". The Budapest Sun. July 25, 2002. Archived from the original on March 2, 2012. Retrieved July 5, 2016.
- Sade, Marquis (2010). La Philosophie dans le boudoir [Filozofija v budoarju ali Nemoralni učitelj] (in Slovenian). Ljubljana: Center za slovensko književnost. p. 110. ISBN 978-961-6789-14-1.
- Philosophy in the Boudoir: Or, The Immoral Mentors. Penguin Classics. 2006. p. 74. ISBN 978-0143039013.
- Sweet, Brian (2000). Steely Dan: Reelin' in the Years. Omnibus Press. p. 42. ISBN 978-0-7119-8279-6.
- "Official Steely Dan FAQ". Retrieved July 5, 2016.
- "Peep Show – Episode Guide – Episode One: Mugging (11 November 2005)". Channel 4. Retrieved July 5, 2016.
- "Peg-Ass-Us". Pack of Others. Retrieved July 5, 2016.
- Jones, Chad (September 23, 2008). "Fringe felicitations: Best of winners, encores announced". Theaterdogs.net. Retrieved July 5, 2016.
- Hope, Clover (February 5, 2015). "Last Night's Broad City Was All About Pegging". Jezebel. Retrieved July 5, 2016.
- Le Vine, Lauren (February 9, 2016). "We Need to Talk About the Pegging Scene in Deadpool". Refinery29. Retrieved July 5, 2016.
- Blue, Violet (2007) The Adventurous Couple's Guide to Strap-On Sex. Cleis Press. ISBN 1-57344-278-X
- Taormino, Tristan (2006)  The Ultimate Guide to Anal Sex for Women. Cleis Press ISBN 1-57344-028-0
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