According to Wikipedia, Pegging is a sexual practice in which a woman penetrates a man's anus with a strap-on dildo. The term "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, women 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 clitoris, to get pleasure from pegging. Men (or sissies) may find stimulation of the anus, rectum, and adjacent organs, and particularly the prostate, enjoyable, which can lead to an anal orgasm. Some men (and sissies) enjoy masturbating (or being masturbated) during pegging - although a true sissy would want to flaccid the whole time and delight in seeing her limp sissy clit dribble as she is pegged.
There is a depiction of pegging in the William S. Burroughs 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.
"Bend Over Boyfriend" or B-O-B is a "wildly successful" series of sex education videos covering the practice of a woman pegging men. The first of the two videos, which was released in 1998, became the best selling video to date for Good Vibrations, a sex-toy business. The video was also featured on The Daily Show. The videos promote the idea, as Eye Weekly puts it, that "fucking your boyfriend in the ass is fun". The videos star sexologist Carol Queen, who discusses pegging and also demonstrates the practice with her lover. The videos also contain footage of other couples engaging in the practice.
In June of 2001, three years after the release of Bend Over Boyfriend, columnist Dan Savage, writing for Seattle’s The Stranger, ran a contest to determine the neologism that would subsequently be used to describe the act of a woman penetrating a man anally while wearing a strap-on dildo. The top three contenders included “BOBing,” after the initials in Bend Over Boyfriend, a testament to the success of the film, which upon its initial release was the fastest-selling video for the San Francisco-based sex shop Good Vibrations (Nathan 16). The other two contenders were “punting,” for “kicking the ball to the other team,” and “pegging,” the term that won the contest. One respondent claimed that pegging was historically significant:
“Pegging was a position in Her Majesty’s Navy. He was the boy available for the after-hours pleasure of the sailors on those long nights at sea. To keep loose for his hard night’s work, he would sit on a peg during the day” (Savage, par. 7).
Other respondents preferred the term because “Peg” is a woman’s name and, thus, evokes the biological sex of the person doing the pegging, and because “getting pegged” just sounds like a great deal more fun than getting “bobbed” or “punted” (Savage, par. 1-15). Yet, whatever the reason for the term’s selection, “pegging” is now a part of the U.S. sexual lexicon.
What true blue sissy wouldn't want to be pegged again and again? I would really love to wrap my sissy lips around some guys pole while he was getting pegged.
A few years back, I made friends online with Mistress Indeep, a wonderful GG who really enjoys pegging sissies.
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