Anal Sex Videos

Narrated by the author and psychotherapist Jack Morin, this Sinclair video offers an excellent and gentle introduction to anal pleasure and anal sex. Debunking the myths and correcting the misinformation, this video features several couples talking about and demonstrating the role anal sex plays in their sex lives. This title covers physiology, anatomy, safety, plus anal sex positions, sex toys, and the all important anal sex communication. 2004, 60 minutes.

For people who want a bit more explicitness in their sex ed videos, the Expert Guide is hosted by Tristan Taormino (author of The Ultimate Guide to Anal Sex for Women) and lets viewers in on one of Taormino's famous anal sex workshops. Following the workshop, two couples take their education to the bedroom, covering both beginner and advanced anal sex techniques, positions, and the use of sex toys. As with all videos in this series you can watch with or without the audio instruction, making this a more "multi-purpose" movie. Link takes you to options for purchase or streaming. 2007, 164 minutes.

Volume two covers some of the basics (including important safer sex information) but delves deeper, if you will, into anal sex play for couples plus some solo prostate stimulation tips for guys. More scenes feature more sex toys (including wooden and steel sex toys) information about extended butt plug wearing, plus it touches on bondage, male anal play, and strap-on sex. As with all titles in the series, this movie doubles as both education and porn. Link takes you to ordering or streaming options. 2011, 129 minutes.

This video focuses on anal massage on both men and women as demonstrated by professionals and then four real-life couples (two male/female couples, one male/male couple, and one female/female couple). There is much more detailed information about different kinds of anal touch than other videos and less of a focus on penile-anal penetration. Includes information on prostate massage for men and the inclusion of vulva massage for women during anal massage. Available for sale and streaming. 2004, 140 minutes.

Produced as a second part to their Anal Massage for Relaxation and Pleasure title, Anal Massage for Lovers offers more information and instruction on anal penetration and a focus on simultaneous anal pleasure for couples (instead of one person “doing” to the other). Like the first volume, this one is hosted by sex educators Carol Queen and Robert Lawrence and features four couples (of different genders and orientations) demonstrating a variety of anal sex techniques. Available for sale, streaming, or Windows download. 2005, 130 minutes.

A completely different kind of anal sex video, Bend Over Boyfriend was the first educational video to offer tips for male/female couples on male anal penetration. Also known as pegging, Bend Over Boyfriend covers all the basics of male anal play, from buying the right toys to talking and positions, and then includes two couples demonstrating their pegging techniques. 1998, 60 minutes.

Consider this a more porn-y update to Bend Over Boyfriend. More polished and featuring porn stars (BOB has a few people who've done it before, but mostly everyone feels like folksy and cute first timers). Tristan Taormino covers the basic how-tos of strap on sex, the gear, and information about prostate stimulation. As always you can watch the DVD with or without the commentary, and there are "mini features" so if you want to get right to the shopping tips or safer sex tips, it's easy to do so. Available as a DVD for sale or streaming. 2009, 102 minutes.

The truth is that most of these videos feature similar information, so the differences are mostly about the delivery. If you're a fan of Nina Hartley you may learn best by watching her first talk about, then, with the help of some porn actor friends, demonstrate basic anal sex technique. It's only men penetrating women with this one, and the look and functionality are certainly older than the Expert Guide series, but Nina is an adorable and enthusiastic teacher, and the information presented is fine (although newer guides have a better and more detailed emphasis on safer sex). Available for sale or streaming. 1996, 78 minutes.

Available in streaming only, this video produced by the great teacher Joseph Kramer offers something none of the other titles do, a focus on solo male anal pleasure. Covering the use of sex toys, external anal stimulation, penetration, and prostate stimulation, the language of pleasure may not connect with every viewer, but it's hard to imagine that you won't learn at least one or two new techniques from this erotic master. 1996, 40 minutes.

The anal sex video that started a revolution, Tristan Taormino’s Ultimate Guide was based on the book of the same name and was one of the first videos to expertly combine good information with porn. In many ways Taormino’s Expert Guide series is a better sex ed video, but watching a group of rowdy porn stars try to talk about anal sex and then have it (including a finale starring Taormino herself) remains both educational and erotic (if you like porn, that is). Available for sale and instant download. 1999, 101 minutes.