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Bend Over Boyfriend (BOB) is a series of sex education videos covering the practice of a woman penetrating a man's anus with a strap-on dildo (known as pegging). 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. The 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".
Bend Over Boyfriend (1998) and Bend Over Boyfriend 2 (1999) were created, produced, and directed by lesbian couple Shar Rednour and Jackie Strano, owners and founders of SIR Video Productions. The movies feature real life couples. BOB was co-produced with Nan Kinney of Fatale Media and was nominated for Best Specialty Release at the 1999 AVN Awards.
Dan Savage, who popularized the term pegging, originally offered "bob" (short for "Bend over Boyfriend") as one of two alternatives for the term. Dan Savage was the guest on The Colbert Report on November 29th, 2010. During the interview, Savage educates Colbert on the practice of pegging.
Some reviewers, such as Eye Weekly, said the tapes are instructional to a fault, saying the presentation "made anal sex seem more distasteful rather than more attractive". Queen herself said she'd been told the first video was "like watching a driving-instruction video" and the subtitle of Bend Over Boyfriend 2: Less Talkin', More Rockin' attempts to address this concern.
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." Taormino also went on to add that the video makers were resistant to visualizing or showing close-ups of the male buttocks in this video.