Bend Over Boyfriend is a 1998 American sex education video created and produced by lesbian couple Shar Rednour and Jackie Strano. It coverers the practice of women penetrating men's anus with a strap-on dildo (pegging). It star sexologist Carol Queen, who discusses and demonstrates the act with her lover. The video also features other couples engaging in the practice. The video was featured on The Daily Show. In 1998, Bend Over Boyfriend became the fastest selling video ever for Good Vibrations, a sex-toy business. It was nominated for Best Specialty Release at the 1999 AVN Awards.

Cast

Production

Bend Over Boyfriend was created and produced by lesbian couple Shar Rednour and Jackie Strano, owners and founders of SIR Video Productions. It directed by Rednour with Strano as assistant director, which was executive produced by Nan Kinney of Fatale Media.

Reception

Sasha from Eye Weekly wrote: "Its underlying message, that fucking your boyfriend in the ass is fun, is a good one", but the presentation "made anal sex seem more distasteful rather than more attractive". Tristan Taormino, writing for the Village Voice, credits the video as an archetype for a substantial cultural shift: "The roles of active initiator and penetrator are no longer solely the domain of men, nor are the qualities of receptivity and passivity for girls only. Nowhere is this more apparent than in what I identify as the Bend Over Boyfriend Archetype."

Sequel

A sequel, Bend Over Boyfriend 2, was released in (1999). Porn star Chloe appears in the second video; as she is best known as an anal queen, her use of a strap-on dildo is a "role reversal". Queen said she was told the first video was "like watching a driving-instruction video", and the sequel, named Bend Over Boyfriend 2: Less Talkin', More Rockin', attempts to address this concern.

Legacy

Dan Savage, who popularized the term pegging, originally offered "bob" (short for "Bend over Boyfriend") as one of two alternatives for the term.