First Time In The Butt

First Time In The Butt
A beginner's guide to getting acquainted with your own backdoor.
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In what’s been a great development for butt-enjoyers everywhere, anal sex is now a lot less taboo than it used to be. For those with penises, it can be especially enjoyable, thanks to the special little walnut-shaped mass of nerves called the prostate situated under the bladder that you can “access” if you go in through the backdoor. Sometimes referred to as the “male G-spot” the prostate can deliver next-level orgasms when it’s properly stimulated. Science is currently trying to figure out why so-called prostate orgasms feel so intense—but, frankly, the why is unimportant. Let’s focus on the how.
Even though people have been sticking various and sundry items up their b-holes for centuries—google “Moche ceramics anal sex” or “ancient Rome butt stuff”—in more recent history, it hasn’t been as common for straight men to partake. So, I talked with Sex and Relationships coach Dr. Charlie Glickman, PhD, who literally wrote the book on prostate pleasure to explain just how to enjoy this under-appreciated erogenous zone. He says the most frequently asked questions he gets from straight men are: “Will it be painful?” “Will it be messy?” and “Does this make me gay?” We’ll get into this more later, but the answers to those burning questions are: it shouldn't be , not necessarily , and no, of course not.
Dr. Glickman's first point? Remember that you’re not filming a porno. Don’t try to emulate anything you’ve seen on Pornhub! You’re just asking to get hurt, and nothing is more discouraging than a supposedly pleasurable sex act that turns painful (assuming you’re going for pleasure, that is). Plus, porn stars are people who are likely having anal sex multiple times a week. And they are prepping for it—they’re just doing so off screen.
For the best chance at a life-changing, earth-quaking orgasm, he also recommends—seriously, listen to this—experimenting with butt play solo at first. For a couple reasons: The first is that it’s an opportunity to figure out what you like at your own pace, which will help you later communicate that to your partner. The second is that you can stop immediately once something becomes painful or uncomfortable. You don't have to worry about finding the right words to avoid killing the mood or discouraging your partner from ever trying this again.
Additionally, don't try to go from 0 to 60 in the beginning. Dr. Glickman recommends getting turned on using your go-to's, the things you already know you like. Not only does arousal cause the pelvic floor to relax, making anal entry easier, but “arousal changes where things land on the pleasure/pain spectrum.” Dr. Glickman explains, “things that feel amazing during sex, might not feel as good [while] reading an email from your boss.” Noted! Once you’ve figured out what it is you like up and around your butt, you can move onto more advanced play that might involve toys, or partners, or specific kinks. Just add new components one at a time. Like the act of anal itself, it’s important to go slowly.
Ahhh, eating ass. It’s been around for ages—probably millennia; the Greeks were definitely giving rimmies. But only recently have people admitted to enjoying it. In 2015, Allison Williams and Girls got a lot of press for putting ass eating on the air and potentially more firmly on the map (although Woody Harrelson was also analingus-ing his young mistress in True Detective a year earlier, and there was a rimming scene in How to Get Away With Murder that year as well).
Rimming is a great place to start with a partner because, unlike other forms of assplay, it doesn't require much advanced preparation. Wash your ass before you ask someone to venture back there, and then relax and enjoy what’s basically an all-encompassing blow job. If you’ve ever had someone touch your perineum (the spot between your balls and butthole), you know there’s a lot of feeling back there, so make sure you don’t knee someone in the face as they make their way to your b-hole. For precisely this reason, it’s often recommended for you to be in doggy-style position while receiving. If you’re worried about hair, get waxed! I know this sounds kind of crazy but waxing your ass is fairly normal (estheticians have seen everything) and it’s nearly painless, unlike waxing the front. I know that’s hard to believe, but it’s true! And it clears the way for easier access to your little tortellini.
Remember way back in 2016 when Amber Rose strongly implied Kanye was a big fan of fingering, prompting Kanye to practically short-circuit as he vehemently tried to deny it? According to a study published in 2010, 24% of men surveyed had received anal fingering, so it’s not nearly as uncommon or taboo as Kanye apparently thinks. A step “up” from the rim job (although, also commonly seen in concert with one another, a la Simon and Garfunkel), fingering requires a bit more preparation. This is where lube comes in. (If someone’s mouth is going to be around your asshole, you can also get flavored lube for rimming to make the experience more fun.)
Like most anal experiences, the slower the better, and remember there is no such thing as too much lube. You want to work your way up to getting inside the back gate, ok? It’s going to take a lot of relaxing; you can help yourself by massaging yourself externally before heading inside. You’re not going to just lie down and get four fingers up there, so slow your roll. Worried about the mess? Get some medical gloves and throw them away when you’re done. Boom! Clean hands, full ass, can’t lose.
Vibrators are not just for people with vaginas ! You can find highly rated “prostate massagers,” on Amazon, like this one , or this one , or this one . Woo! Two-day-ship-yourself the best orgasm of your life. Not ready to make that leap? Or just not into the idea of vibration? Fair enough. It’s strongly recommended that you work your way up to putting anything in your ass anyway, so you can start with anal plugs or beads, which are a lot thinner, and go from there. Often, they come in sets meant for you to build to bigger and bigger toys. Again, lube is your best friend here, so buy some when you check out. Most online sex toy shops these days ( lelo.com , adamandeve.com , babeland.com , jackandjilladult.com ) will recommend specific lubes as you’re purchasing items, and everything comes in discreet packaging shipped right to your house.
If you’re planning on playing solo with a toy, you’ll want to avoid silicone-based lubes, which can degrade certain sex toys. Instead, pick water- or oil-based lubes, however, keep in mind that oil-based lubes ruin condoms so do not ever use them when you’re wearing one. Still not sure which one to go with? Use this guide .
Start small when you get toys. Don’t try to be a hero. Also, make sure that the first few times—or at the very least, the first time—you use a toy, that you’re in full control of the situation. I don’t mean that you’re telling your partner what to do. I mean that you are actually owning and operating the vehicle. Again, it's recommended that you try fingers first , before upgrading to a toy.
So you’re ready to try receiving anal sex, kudos! According to the National Survey of Sex and Behavior from 2009, women who were having anal sex said they that were having way more consistent orgasms than women who were only having vaginal or oral sex. Part of this, of course, is likely that it takes a while to build up to anal, so you’re more likely to be having sex with a partner who knows you well, whom you trust, and whom you have an intimate relationship with. But the point remains: people are coming from anal even when they don’t have a prostate back there. On the BDSM forum, edenfantasys.com , men complain of coming too quickly when they’re being pegged. Almost any time someone describes what a prostate orgasm feels like, they describe it as more intense, even otherworldly, compared to a “normal” dick orgasm. (Not the scientific name for it, I’m sure). If done well, it’s probably going to feel amazing .
The key: prep work. You're probably going to want to clean yourself somewhat beforehand. An hour or so before you plan to have sex, take some time in the shower to get yourself ready. Some people prefer the finger test (literally cleaning as much as you can, sticking your finger up there and seeing if it comes out clean). You can also try douching, just make sure not to overdo it if that's the method you choose. In general, avoid eating foods that are going to make you feel like you need to take a dump; unsurprisingly, that’s not conducive to having hot anal sex.
When it comes to the actual pegging, you’re going to need your partner to go slow. Think about how long it takes your parents to find the slip of paper they wrote the wifi password on one time in 2010, and then go slower than that. If you’ve ever performed anal sex on anyone else, you probably understand this, but once you’re on the receiving end, you’re really gonna get it. Again, it cannot be stressed enough: USE A LOT OF LUBE. More lube than you think a reasonable person would need. Otherwise it’s going to feel like going down a dry water slide. But the dry water slide is your asshole.
A lot of people are going to be down for this, and some people are not. But either way, there’s a whole lot of pleasure being left on the table right now that no one is snatching up. Become friends with your backdoor. Or don’t.
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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 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.

“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!

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.

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.
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.
Want to get started with some anal play yourself? Here are some products to try:
I’m of the mind that one should always have two kinds of lubes on their nightstand: a silicone-based lube, which literally never stops working (avoid spilling it on hardwood floors) but isn’t compatible with silicone toys; and a more traditional water-based lube, which will work with any toy. My silicone lube of choice is usually Uberlube , but for anal play, something thicker like Pjur makes entry easier. Pjur’s anal lube, Backdoor Silicone Glide, has a rich, almost oily texture — just a few drops is all you need — and lasts forever. It’s compatible with condoms, skin, and non-silicone toys (like the stainless steel Njoy Pure Plug, recommended below).
Sliquid Sassy is a water-based lube that’s formulated for anal play, so it’s thicker — closer in texture to a gel — and offers lots of lubrication where you need it. Because it’s water-based, it tends to dry out faster than a silicone lube, but can “reactivated” with a little water — just splash it on where you need things to be a little more slippery. Sassy is great for use with any kind of material, making it a must-have when starting to explore with butt toys. It’s compatible with the two silicone toys recommended below.
The Pure Plug is a joy to behold — it’s a hefty stainless steel butt plug with a cute little looped handle that makes insertion and removal easy. The weight of the steel makes the plug feel more substantial than it really is, and its teardrop shaped head is totally seamless for a smooth entry. Plus, the steel allows for temperature play — it starts off cold, but heats up quickly once in contact with body heat. The Pure Plug comes in three graduated sizes, so you can pick whichever you’re comfortable with… though, fair warning, once you get started with anal toys, nothing’s ever big enough. Once inserted, the Pure Plug is too short to move or rock around, but that’s not really the point of a plug, anyway. For penetration, you’ll want...
Tantus Silk is a great starter dildo for anal play, helping to bridge the size gap between fingers and a penis or strap-on — it’s made of firm silicone, for a pleasantly filling sensation, and smooth enough that you’ll be able to focus more on the pressure of penetration rather than the texture of the dildo itself. Like the Pure Plug, it comes in three graduated sizes, so you can ease your way into anal play — the small is perfect for beginners.
Anal beads are also great for starting out — they increase in size, so the first ones are easily managed; the larger ones provide a satisfying, filling sensation. These ones from Babeland are a bare-bones silicone model with finger loops for easy extraction (pull them out to give an orgasm extra oomph) that should be used with a water-based lube like Sassy. Enjoy!
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