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 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 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.
Instructional materials
A few instructional movies and books have emerged in recent years, including Bend Over Boyfriend, 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 through 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.
In film
The first known pegging scene in film is 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 filmThe Opening of Misty Beethoven. 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?"
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, in a scene where Jeremy is pegged by his then girlfriend Michelle.
It was featured in the television showWeeds, during the episode "Crush Girl Love Panic".
In the January 2007 pilot episode of Dirt, Lucy Spiller blackmails Prince Tyreese 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 seriesBroad 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.
In the episode "To Peg Or Not To Peg" of TV SeriesThe Bold Type, Kat pegs Cody.
In episode 12 of TV series Vida Lyn pegs Rudy. In episode 20 it is referenced that she pegged Johhny.