I am a 25-year-old bi female with a bi male partner the same age. My boyfriend likes stuff up his butt—really likes it. Not being someone who enjoys anal myself, I am continually shocked by his ability and willingness to…uh…take on new challenges in this department. After a few months of playing with plugs and vibrators, I asked him if he would be up for pegging. He responded enthusiastically, so I ran out and bought a strap-on harness and a silicone cock.
Our first attempt gave me a real appreciation for what guys do when they top during intercourse—all that thrusting isn’t as easy as it looks! My boyfriend appreciated my efforts, but he wants me to thrust faster, deeper, and harder. Basically, he wants to be fucked like he’s my prison bitch. Is this kind of “rough” anal sex safe? Everything I’ve read about anal sex says to take it slow and easy. I want to give him what he wants, but I don’t want to hurt him.
—Timid Top in Tacoma
“Sounds to me like TTIT hasn’t seen much gay fisting porn,” says Violet Blue—blogger, columnist, and author of The Adventurous Couple’s Guide to Strap-On Sex, just published by Cleis Press. “Once she sees what looks like the equivalent of guys parking backhoes in each other’s butts, she’ll realize just how resilient this little cavity can be.”
But first, a few words about pegging—aka strap-on sex—for recent high-school graduates and other new readers of this column. Once upon a time, women were doing guys in their asses with strap-on dildos, and it was good. But when a guy wanted to ask for it, or a girl wanted to propose it, they had to say, “Hey, would you be willing to do me/would you let me do you in the ass with a strap-on dildo?” Annoyed by this mouthful, a Savage Love reader suggested that I harness the collective wisdom of my freaky readers and come up with a name for girls fucking guys’ butts, and “pegging” won. It’s crisp, clean, and easily conjugated: He asked her to peg him; she loves pegging him; they pegged all night long.
However, while my readers came up with the term, they didn’t invent the act. “Pegging started showing up in porn circa 1970 and became an increasingly popular sex act for straight kids once strap-on harnesses became commercially available in the 1990s,” says Violet. “As I explain in my book, strap-on sex was so misunderstood by mainstream porn producers that indie-porn companies made films like Bend Over Boyfriend,” which walked couples through the mechanics of pegging, while at the same time demonstrating just how hot it could be.
But porn videos, commercially available harnesses, and catchy names can’t account for the boom in girl-on-boy anal sex, can they? What’s driving the pegging craze? “Perhaps straight guys are more interested in having women play with their asses because of increased awareness about prostate health,” says Violet. (A little butt play can improve prostate health.) “Or maybe, guys are just becoming more comfortable and confident about their heterosexuality.”
So more and more guys like it—but what about guys who like it rough? “TTIT should take it slow and easy at first,” says Violet, “until her guy indicates that he’s ready for more, and then she should certainly give it to him. She should use LOTS of lube—lack of lube will damage the sensitive tissues. She may want to invest in a lube syringe, which is what those ass athletes in porn use prior to every scene. But she’s the guardian of his anal safety at all times and should pay close attention and proceed carefully.”—Dan
I’ve been dating a wonderful guy for about a year now. Two months into our relationship, he expressed his desire to be penetrated by a woman. We bought a strap-on, and he sucked my new dick, and I pegged him. Honestly, it turned me on as much as it did him. Then he started talking about wanting to suck a real dick. I was OK with having a threesome with a trusted, STD-free, bi guy friend who could pay us equal attention. It went well, and we all had fun.
But now he wants to have a real cock up his ass, and I am less OK with it. Every time we have sex, he requests ass play. We never have vaginal intercourse anymore unless I ask. How soon will it be before I am left out entirely? Have I just been the testing ground for a shy gay boy who is now coming to fully realize that he would rather be with men than women?—Pegged Out of the Hole
“In my book, I go on for miles about how pegging doesn’t in any way make, or create, homosexuality,” says Violet. “But POOTH’s concerns about being left out are real, regardless of what her boyfriend is trying to figure out.”
Like Violet, I have gone to great lengths to reassure heterosexual couples that a little anal stimulation—up to and including penetration—can’t turn a straight or bi guy into a gay guy. But sometimes a bi guy who hasn’t experienced much same-sex action will take his first indulgent girlfriend for granted. He’s so excited about exploring cock—real or simulated—that he begins to neglect her needs. A guy like that just needs a slap upside the head. (“Hello? Remember pussy? My pussy? Well, you better start or you’re going to lose the best girlfriend a bi guy ever had, you dumb bitch.”) But at the risk of annoying the bi-furious community, it has to be said that some gay guys do identify as bi at first and will use an indulgent girlfriend as, in POOTH’s words, a “testing ground.”
So how do you figure out if your boyfriend is a thoughtless bisexual or a temporary bisexual?
“POOTH needs to ask her boy why her pussy is so conspicuously out of the picture,” says Violet. “It’s possible that he’s going through an experimental phase. But totally ignoring her fantasies and needs and treating her like a prop—or the peg upon which he hangs his ass at night—is totally unacceptable.”—Dan
Are there any forums out there dedicated to the discussion of pegging for mostly vanilla women? Everything I’ve come across so far seems to be playing into the stereotypes that plague male-on-female anal sex. (“You’re going to take my cock up that little ass,” etc.) I don’t peg my man to work out my aggression, I peg him because the prostate is a wondrous thing. I can’t swim with the hardcore kinksters. Is there a pond for vanilla fishes like me?—Pegging Is for Everyone
“Pegging in most porn is festooned with stereotypes of shame and pain, like most sex in mainstream porn,” says Violet. “And unfortunately, these stereotypes have seeped into online sex culture.”
“But you don’t have to be Mistress Asscrusher and he doesn’t have to answer to Worthless Buttslut in order to enjoy strap-on sex. Like I explain in my book, most couples who peg do it because it’s fun, intimate, new, exciting, and quite loving. PIFE need not feel isolated. She should start a forum of her own, on a space like Tribe.net, and she’ll be pleasantly surprised at how welcome and happy she’ll make the many women like herself feel.”
Violet Blue blogs at tinynibbles.com.—Dan Savage
Dan Savage’s most recent book, The Commitment: Love, Sex, Marriage, and My Family, is on sale now. Send your Savage Love questions to firstname.lastname@example.org. A new Savage Love podcast is available for download every Tuesday at thestranger.com/savage.