A Beginner's Guide to Pegging

This column is written in response to a suggestion from a Tool Shed customer who felt that talking with us at the store had made him feel less "weird" (his word) about his desires, and thought that other men might find the same information valuable. So, forthwith: a beginner's guide for heterosexual men who are interested in being anally penetrated by their female partners.

While anal sex is by no means a new practice, the notion of straight men being the receptive partner during anal play became much more mainstream about 10 years ago, when legendary sex educator Carol Queen made the 1998 educational DVD Bend Over Boyfriend (affectionately known as BOB) with her partner Robert Morgan Lawrence. A few years later, the follow-up DVD, BOB 2: More Rockin', Less Talkin', was released. In 2001, sex columnist Dan Savage held a contest asking his readers to name the practice of a heterosexual man being anally penetrated by a woman wearing a strap-on dildo (which, you must admit, is quite a mouthful). As a result of the contest, the term "pegging" was born.

Once Dan Savage has a contest to name something, you know that particular sex act has hit the mainstream. In this case, the naming of that act also lifted a cloud of shame and confusion that had hung over the idea of a straight man being the receptive partner during sex. Many men associated anal sex with being gay, and thus struggled with the idea that enjoying receptive anal play somehow "made them gay" or, at least, made them less-authentic heterosexuals. In addition, penetration is associated with masculinity, power and dominance in our society, while being penetrated is associated with femininity and submission, so some men also wondered if enjoying anal penetration threatened their masculinity.

Some men enjoy submission and being feminized, so an awareness of those taboos and their attachment to anal play can really add an exciting psychological dimension for those who want that element. For other men, the advent of BOB and "pegging" allowed them to unhook anal play from sexual orientation and masculinity. Enjoying anal penetration could now be seen as simply that: enjoyment, without any reference to a man's sexual orientation or masculinity.

We have a steady stream of male-female couples in the store who are interested in experimenting with pegging. There are several things for people new to the practice to consider, the first of which is the readiness of both partners to try out this new type of play. Communication is essential, especially in addressing some of the misconceptions that each person might have, which include the ones listed above as well as fears that anal sex is painful, dirty, harmful or "wrong." It's also good to start slow. Before investing in a harness and dildo, experimenting with fingers, small butt plugs, or small prostate stimulators can help both members of a couple figure out what they like and don't like as part of anal play.

When a couple feels ready to move on to strap-on sex, choosing a harness and choosing the right dildo are of equal importance. If a harness doesn't fit right, it can make penetration awkward or even impossible. If a dildo is too large, penetration can be unpleasant. I recommend that couples start with an affordable but high-quality convertible harness like the Aslan Commando or Pleasure Principle, which both can be worn as either a one-strap or a two-strap style, with or without a backing pad for stability. When choosing dildos, starting small is usually a good idea. Many men also prefer nonrepresentational dildos (ones that do not have realistic details or resemble a "real" penis). Using a dildo that is smooth and has no distinct head or other ridges can help make penetration feel more comfortable. We also recommend using only 100% silicone dildos, as silicone is body-safe, nonporous and very easy to sterilize. The Tantus Silk series, Tantus Leisure, or Vixen Smooth Operator are all good dildo choices.

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Some couples also want to try double dildos, which have one end that is "worn" internally by a woman while the other end stands ready to penetrate a partner. Some also have vibrators that can stimulate the wearer. At our store, the Feeldoe Slim is a very popular choice, but Fun Factory just started making an intriguing double dildo called the Share Petite, which has a large wearable bulb that can be inserted vaginally, and a very small, finger-sized dildo on the other end that is perfect for pegging newbies.

Some new educational resources are also available. Tristan Taormino's Expert Guide to Anal Pleasure for Men DVD covers pegging and a whole lot more. The Adventurous Couple's Guide to Strap-On Sex by Violet Blue is the go-to guide if this column intrigued you and you want more details on everything I've mentioned so briefly above. Finally, Bill Brent's book The Ultimate Guide to Anal Sex for Men is a perennial best seller in our store and covers almost every type of anal play imaginable, including pegging.

Want Laura to answer your questions in SEXpress? Send them to laura@shepex.com. Not all questions received will be answered in the column, and Laura cannot provide personal answers to questions that do not appear here. Questions sent to this address may be reproduced in this column, both in print and online, and may be edited for clarity and content.

Laura Anne Stuart has a master’s degree in public health and has worked as a sexuality educator for more than a decade. She owns the Tool Shed, an erotic boutique on Milwaukee’s East Side.