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You Need One Of These Lubes For Anal Sex
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Maybe you and your partner have talked about anal sex , or maybe you've kinda-sorta referenced it in a whisper while in bed. You want to do it, but you just... haven’t yet. Talking about it is the first step—and an important one—but making sure it’s enjoyable for each partner? That's a completely different challenge.
Alicia Sinclair, certified sex educator and sexuality coach , says the biggest obstacle to pleasure for many copules is they don’t start slow enough. That's where anal fingering comes into play.
It's pretty much what it sounds like. Anal fingering is the process of using your finger to stimulate your partner in and around the anus. Both partners, regardless of gender, can (and totally should!) enjoy this method of anal sex. Btw, there are two sphincters in the anus—the internal and external sphincters—and both can feel pleasure. (If that's not the definition of a win-win, I don't know what is...)
Wanna have an anal orgasm? Course you do. Here's what you need to know first:
Often, couples try to do too much too soon with anal sex—immediately penetrating the anus with a penis or something of similar size.
"Everyone just goes from zero to 100 and there’s no delicate time to sort of experiment with what feels good," Sinclair says. "If you’re going to penetrate with something the size of a penis, you really need to graduate to those sizes."
You likely introduce fingers to your vulva before inserting a penis or toy during foreplay, right? So, why treat your butt any differently?
Before you do anything, ask for consent. Sinclair recommends having this conversation in a room where you and your partner don't regularly have sex or aren't planning to have sex. So, the bedroom is off limits.
During an open and honest conversation, ask each other: Is this something you both want to do? If either person answers no, then accept that answer. If you both say, "yes," awesome! There are just few things to keep in mind before your first time.
If you and your partner are planning to have anal sex, the person receiving might want to make sure the anal canal is clear. This means having a bowel movement about 45 minutes before sex, Sinclair says. A simple water enema (basically a douche for your behind) works, too. "Fill it with warm water, push that into the anal canal. You can do that a couple times until it runs clear, and then your anal canal is clean," Sinclair suggests.
Because anal fingering is all about pleasure, if you're the giver, make sure your fingernails are nice and short. Clinical sexologist Lindsey Doe suggests not just trimming your nails, but filing them to make sure there aren’t any sharp edges that could cause tears in the anus (OUCH).
Before you do any of this, though, check in with your partner about what they want, so you can both be present in the moment later. For more on how to prep for anal fingering, Doe’s video for her YouTube series "Sexplanations" gets into the details.
Generally, a silicone lube, or even coconut oil , is good for anal sex. But for anal fingering? Not so much. When anything wet first touches the anus, Doe says, it will generally tense up, because it’s only used to wet things coming out of it, not going in. So, take it easy and introduce a dry finger to the outside first.
Set one finger against your partner's anus. This, she explains, is "just to let the anus know 'Hey, we’re here. We’re friendly. We want to do more. Are you interested in that?'" Then, when the anus starts to, in Doe's words, "pucker," it’s time for the lube. This pucker means the external anal sphincter is having a reflexive contraction, and that happens when your partner strokes the skin around the area.
There are many approaches to anal fingering, Sinclair and Doe say. For anal foreplay, you can try a simple anal massage , with small circles, bigger circles, or a finger stroke with one or three fingers. Once anal fingering actually begins, you can stimulate your partner’s external muscle by pushing down on the outside of the anus for a few seconds, Sinclair says.
Then, you can push up. Once you penetrate, you can tickle the internal muscle with the first joint of your finger. Or you can keep your finger stiff and massage in different directions with the tip of your finger. But no matter what, Sinclair says, "Remember to go slow." Keep it slow, and you'll keep it sexy.
Once you and your partner have practiced anal fingering long enough that you feel comfortable handling multiple fingers, you can try playing with butt plugs and then, whenever you're ready, progress to anal sex.
Before I went to college, I was closeted. I barely count those eighteen years as part of life. Why would I? That wasn't me — not really. The most interesting places I've lived — Zambia, South Africa, London — happened during that time, and those experiences were wasted on someone with no cognizance, no words yet. In high school, the only person I knew who was like me was a punk — a mean lesbian with spike collars and pink hair. She teased me outside the lunchroom. I know she had to be tough — ours was a private Christian school with 200 students, and she was out.
In time, she softened. She said hey to me. Then she graduated and disappeared. A few years later, I learned that she transitioned. Dae found his truth, came out as transgender and found his queer family in a city not far from there. We are still friends today. While our journeys are different, we both more or less found the things we needed — the right words to call ourselves, the chosen families we belonged in — at the same time. Dae has become a remarkably handsome man, and in many ways, he was my first sign that others were out there — back when I simply knew I was "other" and that was all I had.
Other sexy trans men came later — casual hookups and kinky playmates — who taught me some of my most important lessons about being queer. Here are some of them.
Editor's note: For consistency, he/him/his are used to reference trans men in this article. Always ask for a person's preferred pronouns at the beginning of conversations.
After a hot sex session, I once asked a trans man what his name was before he transitioned. He said, "No, sorry. I don't say that. It's my deadname." I thought I offended him and apologized. He said it was OK and told me something I'll never forget: "You know when you look back at old photos of yourself and remember how miserable you felt? That's what it's like to think about that name. That life is behind me."
I can barely look back through those photos. I see me, a lanky pipsqueak squinting through big teeth, someone with no clue how to live in my body, no understanding of what it was feeling, and no words to describe it. I'm so grateful to be here now, to have moved into a better life. Sometimes you have to cut your timeline and never look back.
This should be obvious, but apparently not. I talked to some transmasculine friends while writing this piece, and several explained that many people assume trans men are only interested in women.
When we talk about gay and bi men, that includes gay and bi trans men, too. Assuming anyone is straight because of how their gender is presented is an unhealthy hetero projection — one we don't need.
My ability to detect whether or not someone is gay or bi (what some call gaydar) is faulty, so unless I meet someone on a sex app or at a queer-heavy bar, I face the task of expressing interest and seeing if they're interested back. Thankfully, hookup apps usually do the work for me. If you meet an out trans man on an app like Grindr or Scruff, it’s safe to bet he’s interested in other men.
Having a penis doesn't make you a man — nor does having top surgery. Having a vagina doesn't make you a woman. Sex, too, is not all about parts and anatomy, and focusing too much on physical acts ignores the powerful mental, tactile, romantic, and explorative sides of human sexuality.
During a great early sexual encounter with a trans man, I told him I didn't know what to do for his body or how to make him feel good. "What feels good for you?" he asked. "Let's start there." He told me to focus on feelings, not physical actions — a rule-of-thumb for good sex with anyone.
This seems to be another common misconception. Many trans men are tops! I am a bottom and have only ever bottomed for trans men.
There’s more to being a top than having a penis and putting it somewhere. A good top, in my opinion, knows how to listen, take charge, and deliver pleasure at the right speed and intensity. The sexual tools at his disposal are endless — he has his hands, mouth, fingers, strength, breath, and body weight, along with a myriad of sex toys, strap-ons, insertables, and more that exist.
I asked a kinky transmasculine friend what an ideal first message on Grindr would be: “I want to do nasty things with you, what should I call your parts?” I asked how he would answer. He uses “pussy” and “hole,” but knows other trans men who use “bussy" (boy pussy).
I told him that when I get in submissive headspace, I like when guys call my hole a pussy or cunt. I also know some cis gay guys who hate the word "cock" and bristle at its use. Everyone has words they prefer, and those words may change depending on the kind of sex they're having or who they're with. Some trans men say "vagina," others say "front hole" and "back hole." By asking for his words, you’re getting the language you need to talk about sex.
As a cis gay man, I will never know what being trans is like. But I do know there are commonalities among us — family isolation and rejection, hunting for our people, discovering sex on a different timeline than our peers, living in shame and denial, coming out, exploring our first queer spaces, trying on labels, and finding words that fit.
These are the beautiful milestones of queerness that most of us share. Listen to his experience and share yours, and I promise that by the end of the night, you'll be closer.
You know the common Grindr script: Sup? Looking? Into? These days, guys seem to dislike one-word messages because they're economical and efficient and no one likes to be reminded of how they're one of many options. But you are — everyone is. Maybe it's brisk and to-the-point, but I ask "Into?" almost immediately. Someone can reply with what sex role they like, list their kinks, or say they're looking for love. At least two men have listed their hanky code colors, which I appreciated.
If you're gay or bi, a trans gay/bi man is likely into many of the same things you are. Start there. This is the same script you'd use to flirt with anyone because trans men are men.
I still remember the few times I slipped up and wrongly assumed a trans person's pronouns. The memories still fill me with shame and embarrassment. That's good — now I remember to ask. Before you have a chance to do so, get comfortable with 'they' and 'them.' If you're referencing someone whose pronouns you don't know — even if they're not present — get comfortable using gender-neutral pronouns like these.
Doing so might feel awkward at first, but after you get into the practice it will get easier. Doing so is not only respectful of a person's pronouns you don't know — it's also one small step in a massive social movement to challenge binarism and take down archaic notions of gender. Using gender-neutral pronouns, at least until someone's pronouns are confirmed, is not hard and is something you can do every day. Every 'they' and 'them,' even for people whose gender identity you think is obvious, is a small, vital step in a better direction — one that carves space for genderqueer and nonbinary people.
I start talking about sex quickly because I'm bad at flirting. But if asking what words he uses to describe his parts seem a little aggressive, take it down a notch and just flirt.
Again, don't break the ice with tactless, fetishizing statements like “I have such a thing for trans guys.” There’s more to him that makes him attractive. Compliments about a great smile or beautiful eyes are less threatening and genial. Start there.
Before having sex with anyone, you probably have a pre-built script about how it's going to go. Lose that. I had to learn sex with trans men through their patient teaching. One past playmate, in particular, taught me more about my kinks than I knew and pushed me to new levels of understanding with my body. Getting there requires opening your mind and your body to new sensations and silencing the mental playbook you thought you'd use. Every sexual encounter is different because every person is different.
You know the three common sex roles — top, bottom, and versatile — that everyone (not just cis gay men) can be grouped into. There's also a fourth. A couple years ago, The Huffington Post ran a piece by sexpert Joe Kort on gay "sides" — gay men who enjoy sex but do not, for various reasons, like anal penetration.
Gay cis men tend to focus on anal sex as the base requirement of sex — many do not consider other sex acts, like oral sex, to be "sex" at all. As a result, sides often feel embarrassed, ashamed, or left out. But the fact is, anal sex is just one kind of sex, and there are a variety of reasons why one might not find it fun. Some people have health conditions that keep them from enjoying anal sex — others simply don't enjoy it.
I'm not a big fan of oral sex, and could happily cut it from my repertoire without much concern. Some guys feel the same about anal. Thankfully there is massage, rubbing, mutual masturbation, rimming, licking, fingering, and literally endless non-penetrative kinky sex acts you can do. Sex is a miles-long buffet table — why choose only one thing?
A majority of my experiences with trans men have been dominant-submissive with me as the sub. In none of these encounters did a penis go in my butt — and they were all fun.
Some trans men don't want you to play with their vaginas, others do. Everyone has certain kinds of touch they like and certain kinds they don't. You're always allowed to ask what feels good — and you should communicate what feels good to you, too.
If you meet a sexy trans guy in a bathhouse or sex club, you don't have to have a long, sit-down discussion of preferred words, permissible sex acts, and so on. Like everyone else, many trans guys just want to get laid, not have a lengthy conversation beforehand. Keep it casual — play and be willing to change course if something doesn't feel right.
I know many dominant trans men and have played with some of them. Suggesting a man with a vagina wants to be dominated is like assuming every cis gay muscle guy wants to top. If those are your assumptions, good luck.
Fetishizing trans men is problematic for the same reason that fetishizing black men and HIV-positive men are problematic. All three fetishes can lead to harmful stereotypes and misconceptions, and all three can actually reinforce stigma and prejudice.
Guys who fetishize black men generally proliferate the negative, racist image of men of color as 'sexual beasts' ready to dominate white men with their massive penises — a dangerous idea that goes back to colonialism and claims made by racist pseudoscientists that black men are more attuned to baser, animalistic impulses like sex because they are less intelligent, less human than white people.
People who fetishize HIV-positive folks think we're all infectious sex maniacs eagerly spreading our "toxic" seed to anyone unfortunate enough to have sex with us — a concept that contributes to the demonization and criminalization of HIV and adds to HIV stigma. And people who fetishize trans men tend to fetishize a false, trans-negative image — the subservient man with a pussy, eager to bottom for a dominant alpha-top. This idea reduces transness to a surgery and contributes to anti-trans hate.
You don't get a medal. Trans men aren't a box to check off your fantasy list of wild sexual experiences. It's OK to have sex goals, but as the last point illustrated, fetishizing transness — like fetishizing blackness and fetishizing folks with HIV — is harmful and dangerous.
Trans men are men. If you meet a man who you think is really cute, and he's interested in you back, you may have a great sex night ahead of you. When he tells you he's trans, say OK, ask for terms, and have fun.
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Zachary Zane
Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, culture, and entertainment.
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"Penile orgasms are amazing, but there’s nothing like a prostate orgasm."
It’s not greedy to want the most euphoric sex imaginable. As long as you're making sure your partner is having a toe-curling good time too, then you should feel free to maximize your own pleasure—which is why it can be useful to get creative in the bedroom, either by bringing in some toys or getting your rear end involved.
Anal play isn’t for every man, and I understand why you might be reticent to try it. It's still a bit taboo, and it can get a little messy (but so, too, can life—doesn’t mean we stop living). But if you're down to do butt stuf
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