One way to improve your anal sex technique is to buy or rent an educational anal sex video. Adult sex ed. videos range widely in terms of quality of information and production values, but the titles below all have something to recommend them and are, in my opinion, the best of the bunch. While you may want to watch anal sex scenes in pornography for inspiration and arousal, remember that they are almost never a good guide as they are presented in a way that doesn’t match real life anal sex, and a lot of anal sex in porn is dangerous, even when done by professionals. All videos are heterosexual focus unless noted.
Better Sex Guide to Anal Pleasure
Sinclair Institute
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. 60 mins.
Expert Guide to Anal Sex
Vivid Ed
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. 164 mins.
Anal Massage for Relaxation and Pleasure
Joseph Kramer
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. 140 mins.
Anal Massage for Lovers
Joseph Kramer
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. 130 mins.
Bend Over Boyfriend
Fatale Media
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. 60 mins.
Ultimate Guide to Anal Sex for Women
Pucker Up
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). 101 mins.
