My natural-born frenemy Dan Savage popularized the term "pegging" after it was voted the winning entry in a contest he ran in 2001, when he and his loyal readers realized that there was no common word for a woman strapping it on and penetrating her man anally.
"Pegging" beat out close runner-ups "Bob," an acronym for "bend over, boyfriend" and "Punt," likening the act to kicking the ball to the other team. I could swear that I used "pegging" before said contest, which inspired 12,000 people to vote-in. But—whatever.
Pegging, as I will call it despite its being "invented" by "The World's Most Popular Sex Columnist" or whomever, is something all you opposite-sexed couples out there should try at least once. Yes, He-Who-Must-Not-Be-Named agrees with this statement. This sexy act is already uber-pleasurable for your lucky guy thanks to his prostate (a.k.a. the male G-spot). But when paired with simultaneous manual stimulation with a sleeve stimulator (like the vibrating Cobra Libre or textured Tenga Egg) it's extra explosive from all angles.
Off-the-charts orgasms aside, this role-reversing act also eroticizes feminine domination and can be a new way for hetero-paired couples to explore trust, intimacy and sexual liberation for both. For others, it could just be another Thursday night. Either way, pegging necessitates some valuable tools.
As always, a little reading will go a long way, especially when it comes to the delicate man-booty (and its attached macho social expectations). Read past columns "Prostate Power," Parts I and II (August 26, 2010 and September 2, 2010), for tips on why enjoying prostate stimulation does not make him gay, dirty or in pain (unless you want these things, of course) and how to start exploring it for the first time (as in start with your fingers or a small toy before getting all Peggy Sue on his ass).
Other sources to consult include Tristan Taormino's porno Expert Guide to Anal Sex for Men and Violet Blue's The Adventurous Couple's Guide to Strap-On Sex, which include pegging positions and advice.
After having lots of sexually evolved conversations about how great it's going to be to explore new sexual boundaries as well as your own sexual and gender identities through this formerly taboo act, you're gonna need to get yourself a little dick. Literally.
Good Vibrations has an economical toy package called the "Bend-over Beginner Kit," which comes with two very modestly-sized silicone dildos and a vibrating harness with which to strap them to you. While the harness is definitely of starter-kit quality, the vibrator buzzing against your naughty bits adds a little cha-ching.
Another way to get yours while you give it to him is by using a double-ended dildo. Check out the Share series by Fun Factory, which are designed to be worn hands-free and harness-free, with one end penetrating the pegger while the other is used on the pegee. Short and bulbous on one end for her (and her G-spot) and super svelte and beginner-friendly for him, the Share XS is the perfect peg for a newbie.
Graduates can use the noticeably longer and wider standard-sized Share while those pursuing their Ph.D.s (Pretty Huge Dildo) in pegging can challenge themselves to use the Share XL, a giant, ribbed dose of double trouble. Those who want to enjoy a rougher ride without constantly readjusting should consider harnessing their double-ender, which can be done by securing the harness ring around the bend between the two ends and using a harness without a back pad, such as the ASLAN commando.
If the double is a little too much trouble, choose a modestly-sized regular dildo (the Happy Valley Harmony is ridged and vibrates to stimulate pegger's privates) and a fun, girly harness to accentuate your femdom fun. The hot pink ASLAN Crystal Minx, the icy white, thong-style Theo by Spareparts (which accommodates two bullet vibes in the harness pad) or the Betty Harness, which looks like a pair of panties fit for a '50s pinup, will all surely inspire him to take it like man.