Sex & Relationships

Sex With a Strap On: The Politics of Penetration

What gender dynamics and stereotypes are exposed and undercut in sexual role reversal?

“I think you’re the one,” he said. We were taking a break from a marathon fuck fest, sweaty, spent, and lying on our sides when he said those words to me, words that I’d been told every girl wanted to hear at some point in their lives. Except, of course, Seth wasn’t my boyfriend, and he wasn’t professing his undying love for me. He was my friend with benefits, and he was trying to convince me to don a strap-on and do him in the ass. After he told me I was “the one,” it wasn’t just my ego I wanted him to stroke. What are friends for, I thought, if not to tell you when you have spinach in your teeth and to give you an occasional reach around?

I had been trying to get Seth to let me do him in the butt for years, way before we started sleeping together. He was, in fact, dating a girl I was in love with when we first met in Tucson. They came down from Phoenix for a party I was having, and after a jug of Carlo Rossi wine, I pulled out my box of sex toys (like ya do), including a garishly pink rubber dildo and thong harness that I bought on the clearance rack at Fascinations. The first time I tried it on I felt like I was on American Gladiators. All I needed was to draw some stars on my ass and I’d be ready to joust. Aside from its hideous color, which I assumed was to make it seem less threatening, less male, and therefore more acceptable to impale somebody with, it was very versatile. This particular strap-on came with a vibrator, a vibrator pocket that nestled right up next to my clit, a hooked nose for g-spot stimulation, and a nob right about where a partner’s clit should be. It was like a one-man band, or a really thoughtful rhinoceros. In my extreme inebriation, I thought it neither tactless nor gross to lend my friends the strap-on I fucked my girlfriend with on a semi-regular basis in order to take Seth’s anal virginity. The look on his face told me immediately that that was not going to happen, and I tried to seem less disappointed than I actually was.

Years later, Seth and I reconnected in San Francisco, and after a fairly traumatic break up with my girlfriend of two-and-a-half years who decided she wanted to be straight, he and I ended up in bed together (like ya do). After a long and varied sex session that lasted several hours, he popped the strap-on question. “I’ve had other girls try it, with limited success,” he said. “But you, I think you’re the one.”

I've often questioned the role of role playing in sex. How we are socially and behaviorally predisposed to certain inclinations, sexual or otherwise. How much did my status as a bottom -- my desire to be dominated in bed -- inhibit my use of strap-ons in erotic play, especially when submission, for me, was the ultimate erotic transgression? Women are socialized not to act, but to react, and this passivity and reticence in everyday occurrences often translates into the bedroom as well.

Think of the aggression gay men often display when seeking a sexual conquest and how women on all sides of the sexual spectrum tend to have a less aggressive approach to sex outside of love and commitment. Witness the polarities between Women Seeking Women and Men Seeking Men ads on Craigslist sometime, if you don’t believe me. Another example of this can be found in Lillian Faderman’s “Odd Girls and Twilight Lovers” where a lesbian sex-radical in the 80s advertised, “bare bottom spankings, immobilizing bondage, enemas, colonic irrigations, vaginal and rectal exams, dildos and vibrators” then ended with “and after I’ve endured what was bestowed upon me, comfort me in your loving arms. Long term relationship possible.”

Weirdly, I never felt truly confident strapping it on until I started using them on dudes. It always seemed kind of silly—a femme with a dick. I certainly never felt like a dude when I strapped, more like a wayward unicorn. A hot one though. An empowered unicorn. I associated power with masculinity, but I never felt masculine. I asked Seth if riding the brown caboose made him feel like he was giving something up. He said, “I don’t feel powerless. In my mind, whoever’s getting off the hardest is the one who’s most empowered, ultimately.”

Taking a man dirt-roading for a change isn’t just a fuck, but a mind fuck, and a powerful one at that. As one of my friends put it, “Topping someone much bigger than you as a woman is amazing. I may never beat you in arm wrestling, but I can fuck you in the ass. Can you imagine a 6'5" man with those legs up in the air? Beeeauuuuutiful.”

Seth owned his own dildo and strap-on, which was not only convenient, but a testament to his dedication to the craft. As soon as he brought it out, I became suddenly nervous. In all my years of fucking women with strap-ons, I’d had many flubs, faux pas, and episodes of even hurling dildos across rooms out of frustration. Also, even though I’m happy to take the reins in the sack whenever necessary, in my heart of hearts, I like to be taken, not the other way around. But Seth’s longing and experience as a receiver put me at ease, (it also didn’t hurt that I was several vodka gimlets deep at that point) and as I stepped into the harness and tightened the straps, the familiarity and breathlessness came rushing back. I lubed up the modestly-sized dildo as he readied himself on his back, knees hugging his chest to make room for me. The first shock of contact, of connection, is always exhilarating, and when it happened, I felt him stiffen slightly, then push back into me, emitting a soft, wordless sound. I went slowly at first, listening for his exhalations and murmurs of “That feels so good.” There’s nothing sexier than that first audible or physical release of inhibition, and I felt myself flush at the sound of his voice, the giving and the taking that was happening all at once. I angled slightly up toward him, held onto his outer thighs to steady myself, and in that small gesture, I heard his breath quicken, which in turn made my movements quicken as well. In that moment, he looked up at me, appreciative, contemplative maybe, and pushed the hair out of my face, which had swiftly become dampened with sweat.

I tried to keep my focus on his words, his movements, but I was also too turned on to really pay much attention. I felt both amazed and overwhelmed at this steamy subversiveness, something that rarely existed in my normal, day-to-day life.

None of the men I fucked ever felt ashamed or weird about it afterward. Indeed, they seemed to relish the opportunity to explore. It’s not very often, after all, that men are allowed to be sexually vulnerable. Admissions to even having such a desire often lead to the tiresome stereotype of closeted gayness. I asked Seth over beers recently if anyone ever assumed he was gay or bi because he liked strap-on sex. “I’m sure they do,” he said. “But I don’t talk about it publicly that often…just to reporters, and the entire Internet.”

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