I Pegged a Boy and I Liked It

“How many people have you fucked with that thing anyway?” my boyfriend asks over the phone. I giggle for far too long in response. A cackle, really.

“Now you know how we feel,” I say.

This isn’t the first time I’ve brought up strap-on sex, much to his distaste. My boyfriend is uncertain, but I’m persistent. “Just the tip?” I ask. “I can always pull out if it gets too intense…. you know… if you like it too much.”

As we talk, I hold the member in question: seven and a half inches of realistic vanilla cyberskin. Thick shaft. Bouncy head. Taut balls. I pour on some lube and begin to stroke the silicone absentmindedly, giving my fist a slight twirl, imagining how it would feel for him to hold my cock.

“Baby, do we have to rush into this? Can’t you just… lick my ass or something?”

“Babyyyy,” I say, pointing the dildo at the ceiling, “You let me know when you’re ready, OK? I’m hard for you.”

I hang up without saying goodbye, the way people do in movies. I linger in bed and smoke out the window, quite pleased with myself.

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At this point, there’s no need in touting the popularity of hetero “anal play.” It’s just common knowledge that nearly all men want to penetrate you-women, us-women, in the ass. But now, many men, greedy fucks that they are, also want to experience anal pleasure on their own terms, moving their hips mid-blowjob so that a tongue or finger slips toward that cute hairy little fecal hole.

And so, even the more extreme act of pegging—a girl fucking a dude in the butt with a strap-on dildo—is trending. (#peggingistrending) The act was featured in a recent episode of Comedy Central’s Broad City, the show that takes place in Brooklyn and follows the lives of a pair of 20-something white girls, a demographic to which I belong. Pegging is having such a moment, it has even been a plot point in a spattering of CSI-type crime dramas and used as the butt of some jokes in a few Hollywood comedies.

And of course, it’s all over porn. You’d be surprised by the amount of quality strap-on fuck videos that have accumulated in recent years. In addition to the “sex-positive” classics Bend Over Boyfriend and Bend Over Boyfriend 2: More Rockin’ Less Talkin’, you can find pop-up window after pop-up window of glossy girl-humping-guy scenes. Thank the divine bitch goddesses of Kink.com.

I can’t say I don’t find pleasure in playing with a man’s butthole. There’s a certain satisfaction in thrusting a middle finger up a dude’s ass. But an anal fuck is more advanced. It is intense. I know, of course, because I’ve done it for boyfriends who wanted it, and it’s true what they say: With the right amount of drugs and lubricant, it can be heaven… but mostly it hurts.

Alone in my room, after I’m off the phone with my boyfriend, I can’t stop watching strap-on porn. I like it. I like the female roles, flat as they are. I prefer the girls who act loving and firm, or coy and cruel, like a little girl who takes pleasure in ripping the wings from insects. Still, it’s impossible to break through the cloud of male fantasy.

From what I gather, the men want one of two things: Either he is looking for an intimate exploration of anal pleasure (all those boyfriends pressuring a sig-other to bend them over) or they want the femme-dom experience of being fucked and humiliated by a woman so powerful she “makes you” take cock.

But who cares what men want. Men will fetishize anything. They’re dogs. Sooner or later, they all howl.

This was supposed to be about what I wanted.

I think about fucking him over the arm of the sofa, the throw blanket folded beneath him so I can grab at either end, making a sling to hoist and thrust myself in more deeply.

Perhaps other women have felt this desire, but then who knows what other women want. All I know is fantasies aren’t formed in a bubble and mine began when the near constant sex with my boyfriend began to wane.

When we first met the energy between us was so strong we could barely go out in public. It was as if by looking at each other, we were already touching. Each kiss was an orgy and we were in constant danger of devouring each other. “No. Not yet, not yet,” I’d hiss as I slid my body nude against his, beginning the beastly struggle that he inevitably won, thrusting with an immense stabbing that gave way to pleasure.

He told me from the beginning that normally, he identified as a submissive, but in our sex he was undeniably the dominant.

I guess any role becomes a burden the more fixed it feels.

“You’re stealing all of the sub-space in this relationship,” he once playfully scolded while slapping me across the face in the shower.

But as we grew closer, the dynamic began to shift. We were sweet, we were cozy. We were no longer having sex in public.

“Do you love me?” he asked.

“I’m not sure… I’m not sure you’re worthy of my love,” I teased.

I wanted to take it further, but I felt timid. I was sure that if we switched we would find something even deeper and my fantasies only grew more elaborate and violent as I craved this control. But I was nervous. I needed a sexual prop.

If only I had what Freud called the “far superior” male equipment. If only we both had cocks… how much we would worship them.

In my mind, it was all planned out. I would arrive at 9 PM and just after he greeted me with a kiss, I would order him to turn around. “OK,” I would continue, leading him to the bedroom by the nape of the neck. “There is something I need you to do for me and because you’re such a good boyfriend, I know that you will.”

But I don’t say this. Instead, I follow him to the sofa where we bundle together, drink whiskey, and make lazy pillow talk.

“Which male Disney character would you have sex with?” I ask.

“I don’t know. Maybe the dad from Aladdin—the jolly fat clueless dad,” he grins idiotically, “Or maybe that warthog that sings ‘Hakuna Matata.’”

“I was thinking more like Scar from Lion King,” I say.

“No. That’s too obvious.”

As we nestle together, the fantasy runs through my mind: “Put it in your mouth. Do it fancy… the way you like,” I would say as he tongued the crown of the silicone, rhythmically gliding, swiveling his head from side to side, looking up with expectant blue eyes.

I think about fucking him over the arm of the sofa, the throw blanket folded beneath him so I can grab at either end, making a sling to hoist and thrust myself in more deeply.

But here we were, assessing the fuckability of various cartoon mammals.

When it is finally late and we are going to sleep, I ask him to take off his clothes. “Now take off mine,” I say and he curls into my naked chest.

“Baby,” he whimpers, softly writhing against my belly. “I want to fuck you.”

I take my time and slowly graze his cock with my palm. “Are you going to give me what I want?” I tease. “Are you going to do everything I say?” And at that moment he goes limp in my hand.

“Baby, why do you have to bring a power dynamic into it? I just wanted to have nice sex with you. It’s not like I always want sex.”

In the hours that follow, I stroke his hair and we talk about it: The ambivalence toward his own kinks, a hesitation in his lust for me as we become more emotionally entangled, a bewilderment toward typical male desire, an uncertainty of how to desire sex in general.

“Just try to accept it… like a woman,” I say.

“I’ve been trying,” he says.

We talk for too long and then he says things that make me angry. I roll over to sleep but continue to wake as he tosses toward and then away from me.

Something happens to us in between dreams. Everything we had spoken about means nothing anymore. He reaches for my body and we are saturated with our many different kinds of kisses, with spit and lube, my fingers at the root of his ass, twirling to find the internal nook that causes his moans to ripple.

In the soft morning I fumble to fasten the harness.

Below me, he is quiet as I press the tip of the silicone to his flesh. For a moment it isn’t going to work but then there’s a give, a slide, and he thrashes, teeth gleaming. I pin him with my elbows and remain still for a long moment. I begin to move, slowly, so that his cries eventually grow melodic, his cock glistening and stiff against his belly.

You poor men! This is a lot of work, the whole business of endlessly thrusting, mentally calculating, thrusting, knowing you could physically harm the person beneath you.

“You ride me,” I command, out of breath.

But in the switch, he has gone soft.

Maybe pegging is just about revenge? But who cares.

“Let’s keep going,” I say, the lack of sleep leaving me unhinged. “The harness was rubbing me nicely. I think I can come. I’m still hard!”

If I know anything, it’s that my desires are inextricably tangled with those of men, but surely, I have some wants of my own. Surely, the fact that boyfriends so rarely want to enact my fantasies speaks to this. Such is the tragedy of the female pervert.

Maybe pegging (#thetrend) is just about revenge? But who cares.

“No way. I can’t keep going,” he says, collapsing in my lap. “I’m sorry baby. But that’s it.”

“It’s OK,” I say. “You don’t have to apologize. You were great.”

We nestle for a moment longer. “But you can apologize for all of the men,” I add.

He lifts his head from my thighs. “I am sorry for all of the men. I truly am.”

Rachel Rabbit White is a writer living in New York City. Follow her on Twitter or stalk her on Instagram.