It’s generally been the consensus that butt stuff has entered mainstream American sexuality. A finger up the tush has become de rigeur, if not always a first date move — props to the sex paladin who ate my butt on the first date though, what a keeper — with more fingers to come, and, yes, eventually the schlong is expected to slide into that lil’ hole, too.
Anal sex, elusive, oft-maligned, and messy, still sits somewhere at the crossroads of “millennial third base” and “holy grail” for some dudes. It’s simultaneously super-taboo and like, totally vanilla if you don’t give him the butt at some point. I don’t think I’ve ever been with a dude who hasn’t asked for it, but they’re all totally aghast if you mention they’re not your butt-first. That’s all par for the madonna/whore complex course, but if I’ve learned anything in my time on this earth, it’s that there are few things worse than reluctant participation in butt stuff. When it’s great, it’s really really great… and when it’s bad, it’s terrible.
So what’s anal sex like for a lady? And how can you make sure it’s not just bearable, but totally dope? Come on a journey through time with your good friend Cat, and I’ll tell you about my first time…
A bit of scene-setting. I’m like, 19, and seeing this guy who’s totally in love with my tush. Whether he loves the rest of me is debatable, but he has what I believe to be the most perfect penis in the world and I’m totally in love with him so we make it work. He’s brought up butt stuff before, but I’ve always rebuffed him, only allowing a finger — sometimes two — to find its way back there, and always with lube.
(Butt stuff: you’ll never have too much lube!)
However, I do want to try anal, if only so that I can say I’ve done it. I’m intrigued by the idea of another route to pleasure, and though I’m not sure if it’ll be strictly pleasurable, knowing how badly he wants it is almost hot enough to get me off. So one night after getting thoroughly sauced and after he’s made me come enough times to render me pleasingly glowy and melty, I tell him it’s time.
He grins so wide it’s endearing as hell and my dumb little heart goes pitter-pitter-patter. “Are you sure?” he asks.
“Don’t make me change my mind!” I tell him. I’m already on my knees, my butt perked up, at attention. And then… is he? Yeah, he definitely is. This was like, five years before Jhene Aiko wrote those lyrics but dude is definitely eating my booty like groceries. And it’s fantastic.
Science lesson: The opening of the anus is full of nerve endings, so it’s super sensitive. That’s why anilingus is so great; your li’l butthole is just totally dazzled by stimulation! But it’s also why it’s imperative to start out slow when it comes to butt stuff, because all those nerve endings mean that getting stretched out before you’re ready really hurts.
So, dude is eating my butt for a while and I’m seeing stars and it’s all wonderful. Then, unbearably, he stops. One lubed-up finger slides in… cool, I’m used to this. After a pause to get me acclimated, he adds another, and it feels… full, and stings a little, but it’s not bad. Then another.
“How does it feel?” he asks me.
“Mmmph,” I say. My face is sort of smushed into a pillow, and I’m trying to take it, and I know if I just relaxed a little it’d be so much easier, but lol my sphincter has other ideas. I’m focusing on my breathing and he leans down and kisses me on the side of the forehead.
“You’re doing so well,” he says, tenderly, and my heart breaks into a billion little pieces and I’m like, OK, I’m ready, I’m ready!
I tell him I’m ready.
On goes the condom, slicked over in a cold coating of lube. He braces himself with a hand on my back, still slippery with lubricant, and slides in, a tiny bit at a time. He’s watching for my reaction, for which I’m grateful. Then he begins thrusting—slowly at first. I can hear his awe-struck reaction at the new sensation somewhere above my head.
“How is it?” I ask him.
“Amazing,” he says.
So what’s first-time anal like? To be honest, for me it mostly hurts. There’s a feeling I can only describe as… burning, an expansion where my body isn’t used to accommodating something so large. But underneath it is a tiny electric current of pleasure, whitehot in its intensity, and as he keeps going, I feel it surface, until it totally overtakes the pain. I hear moaning and lol, it’s actually me. Suddenly, it’s intimate and achey and wonderful and I’m almost a little sad when he comes—quicker than he normally does—and pulls out. I can still feel him inside me.
“That was great,” he says.
“Let’s shower,” I say.
(What can I say? I’m a romantic.)
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After him, there were other guys, of course. One guy tried to put it in without enough lube and that ended disastrously. Another guy put it in my butt by accident—that didn’t end well, either, though more because I was horrified at his poor aim than anything else. But as first times go, my first time with a dick in my tush went pretty great, and I should hope that it is always so good for you. There was trust, there was anilingus, and there was a bunch of lube.