The Pinky Swear

Benefits of prostate stimulation and the rise of bend-over boyfriends

Two years ago, I went to Hedonism III in Jamaica for Juli Ashton's Soul Days, a week's vacation with porn stars. Juli invited Florida-based band Boxelder (boxelder.com) as the featured entertainment, and three tattooed rocker dudes from the band played sets and hung out with the crowd. One night at dinner, Boxelder guitarist Matt Cahur was at my table, and we got to talking about—what else?—anal sex. I was giving him my spiel about how every man should have his prostate stimulated through anal penetration at least once before he dies. I said something like, "Every guy could take at least a pinky." (Last month I got Howard Stern to say that maybe he'd take a pinky in his ass, and maybe is better than never.) Matt suggested that all our fellow tablemates take a "pinky swear" that they'd give it a try. We each wrapped our pinky fingers around those of our neighbors and the pact was sealed.

When most guys think of their prostates, less than sexy images come to mind. Picture the common warning label "Do not take this medication if you have an enlarged prostate," a poster reading "Prostate Cancer: Men Get It," or a proctologist with a latex glove and a tube of KY. Prostate health awareness is important, but the prostate is not just a body part prone to disease and subject to medical exams. It's an erogenous zone and a source of tremendous pleasure. Put the public-service announcements out of your mind and consider the orgasmic possibilities.

The prostate is a gland that surrounds the urethra. To directly stimulate a guy's prostate, slide a well-lubricated finger about an inch and a half to two inches inside his bum, aiming toward the front of his body. Through the front rectal wall, you'll feel a textured area about the size of a walnut. Once you've found it, begin slowly and gently massaging it. Work your way up to firmer pressure and experiment with different kinds of stimulation. Through prostate stimulation, men can achieve orgasm, and some men say they have more intense orgasms this way. Others can have an orgasm without ejaculation or one that only releases prostatic fluid.

Samantha Ryan, Kurt Lockwood, and Sandra Romain on the set of
Devinn Lane's Guide to Strap-on Sex
Courtesy of ShanesWorld.com
Samantha Ryan, Kurt Lockwood, and Sandra Romain on the set of Devinn Lane's Guide to Strap-on Sex

Prostate stimulation feels good and can be good for you! Research has found that men who masturbate or ejaculate frequently lessen their risk of prostate problems, including cancer. Prostate stimulation has been recommended as a treatment for inflammation of the prostate, impotence, and erection problems. One of the most popular anal toys for men, the Aneros (aneros.com), was originally designed as a medical device for people with prostate problems. Then users started reporting the pleasurable sensations and orgasms they achieved with it. Although it is still marketed for health purposes, there is more emphasis on its role as a pleasure tool to give men what the official website calls a "Super Orgasm."

Speaking of toys, every day that I worked at Toys in Babeland, I sold at least one strap-on harness and dildo to a straight couple for her to do him in the butt. Since I began teaching anal-sex workshops in 1998, the discussion of male anal pleasure, especially among straight people, has increased tenfold. The number of heterosexual men who've vocalized their love for being on the receiving end of ass play has jumped significantly. Girls buttfucking boys has definitely become more mainstream.

In the '90s, the independently produced instructional video Bend Over Boyfriend was meant to teach women how to give it to their guys good. It was wildly successful and spawned a second volume that focused less on the how-to and more on hot examples. In addition to Bend Over Boyfriend, other underground titles, mostly those featuring professional dominatrices and submissive men, showcased this edgy kind of sex. Within mainstream porn, a girl-on-guy strap-on scene may pop up here and there, but there was only one series devoted to it: Pleasure Productions' Babes Ballin' Boys, which debuted in 1997. In this decade, the genre has grown significantly; joining Babes, which now has 13 volumes, are series like Strap It On, Strap on Chicks, 100% Strap, and Strap Attack.

This year, a high-profile male performer did his first strap-on scene. Up until now, the male performers who took it up the ass for pay were either amateurs, D-listers, bisexual, or gay. The industry considered it to be a fetish but nothing that the big boys would do or that the majority of viewers might like. Then A-lister Kurt Lockwood (kurtlockwood.com) starred in Devinn Lane's Guide to Strap-On Sex from Shane's World (shanesworld.com, released April 17). The reactions to Lockwood's scene from insiders have been astoundingly ignorant: Gossip sites and messages boards were filled with homophobic tirades that began, "See, I told you Kurt was gay! This proves it!" However, fans seem to tell a different story: It was one of the most pre-ordered titles Shane's World has ever released.

Porn writer Gram Ponante (gramponante.com) visited the set of Pegging 101, a new Black Widow production on the subject, and he questioned whether the male talent—all amateurs allegedly recruited on Craigslist—were "into it." He wrote: "The reason I feel some of the male talent weren't committed to the job and were there because they needed the cash was because they didn't inhabit the roles of traditional submissives or bottoms." This points to another misconception about boys who bend over: You've got to be a wuss to take it up the ass. This myth is both perpetuated and fetishized by the "now who's the bitch?" spirit of some strap-on videos. But the truth is that a guy's masculinity and sexual orientation are not put in jeopardy by simply enjoying anal pleasure, and a dude doesn't have to be submissive to love his ass getting reamed by a woman. This is also where Kurt Lockwood shakes things up, because he is not some guy off the street; he is a porn stud with the cock and credentials to prove it.

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