Started From the Bottom: A Beginner's Guide to Anal Sex

Isn’t it funny how the word “anal” is used to describe people who are uptight or fussy? Anal folks tend to make comments about sex such as, “Why was the sewer built next to the playground?” 

We don’t know why high concentrations of nerves are located where they are on our bodies (like the anus). Nonetheless, we have these zones that respond to touch with such arousal that we had to borrow from the Greeks to call them erogenous. (And we all know how the Greeks got down.)

The number of people either trying or regularly engaging in anal intercourse has somewhat risen over the last two decades. Results of a survey conducted last year state that of the 3,000 participants questioned, 35 percent of women and 15 percent of men said they are having anal intercourse “at least some of the time.” Back in the early to mid ‘90s the percentage of women was closer to nine. Yes, women are into it. No, it’s not just a male-on-male pastime. Yes, it’s a completely normal, celebrated and valid way to achieve orgasm.

Before we get into it, I’d like to quickly re-plant some important seeds:

  1. If you are engaging in anal sex and not in a monogamous relationship, PLEASE use condoms. Please, please, please. There is no excuse to not have safe sex at this point in our evolution.
  2. If you are in a heterosexual relationship, please do not use the same condom for vaginal intercourse if you start with anal sex. It will save you both a world of grief, and save time in the doctor’s office with a UTI or worse.

So, let’s do this! Let’s go deep and continue to un-taboo anal sex. Because, as previous columnists have said: It’s [insert decade here]. Time to get real.


Backdoor in the Limelight

It’s no secret that Sex and the City was in the barrier-breaking business during its late-’90s/early noughts run. The writers and creators held a clear stance, dedicating an episode to anal exploration early on in the first season. Miranda’s response to Charlotte’s hesitation over a new boyfriend who expressed a desire for anal intercourse was most noteworthy. Miranda asserts: “It's all about control. [...] Now there's a certain camp that believes whoever holds the dick, holds the power. The question is: if he goes up your butt, will he respect you more or respect you less? That's the issue."

It’s one take on the issue, but the point of that whole scene was to alert the public that these conversations really were taking place across America, if not the globe. Broad City and The Mindy Project have since expanded the discussion, guiding a whole new generation of even smarter, more self-aware, more beautifully complex women toward honest self-reflection. And thank goodness for that.

In Broad City, Abbi hooks up with her neighbor and she panics when he switches up the power dynamics and asks her to anally penetrate (or “peg”) him when she suggests they change positions. She decides to proceed, following a scene-stealing phone call with Ilana for advice. Later, Ilana lifts Abbi’s morale like Simba to a congregation. (With Ilana’s whole family in the room, following Grandma Esther’s funeral.)

The Mindy Project focused its episode "I Slipped" on Mindy’s partner, Danny, suddenly taking certain bedroom liberties with her, amidst a setting of established monogamy. After rightly saying that she did not consent, Mindy abruptly ends their coitus and gets frustrated by feedback loops about her sexual inadequacies (“Maybe I just need to relax more…")

All it took for things to get back on course was open and reciprocating communication. They both discover they’re new to anal sex, and make decisions about what works best for their relationship going forward.


The Lowdown on Getting Down

When done very carefully, considerately, and correctly, anal intercourse has been known to result in stronger and more consistent orgasms. Tenderness is so key here. Start as slowly and gently as possible. When with a partner, always check in with each other along the way to make sure comfort levels stay paramount.

I’m a personal fan of the Bfilled Classic Unleashed remote-controlled vibrating plug. It’s an ideal beginner’s device, giving you a real opportunity to sate your curiosity with integrity. It’s important to use a tapered product with a flared base to prevent...well, losing it. And you get to learn what feels best as you find your pace. They’re also supremely smooth and just kind to your body.

While it’s normal to associate sex with wetness, the anus does not self-lubricate like the vagina does. You will absolutely require lubricant (water-based only, oil-based lubes ruin latex condoms). Be very prepared to spend time on foreplay. Trust me, a slower start makes for a better build up. The walls of the anal canal are much thinner, and therefore much more prone to injury and micro-tearing than the vaginal wall, hence why slow and steady is best.

It’s also good to start with familiar stimulation of other more commonly attended to erogenous zones. Additional or simultaneous stimulation of those other spots helps beginners gradually ease into the sensations of anal play. Similarities between the anal entrance and vaginal opening also mean that a bit of light teasing goes a long way. As anal stimulation increases, the more likely you are to wake up the shared nerve pathways and kickstart that sensation of deep vaginal orgasm.

If I may briefly drop some high school science on you, all the nerve endings in your body are linked to your nervous system. Stress reduction is a huge component in maintaining a healthy nervous system. You know what reduces stress? Activities like anal sex. You know what a balanced nervous system helps with??

  • Pain Relief
  • Cardiovascular Health
  • Blood Circulation
  • Respiration
  • Memory and General Brain Function

I’ve said this in previous posts and it’s just as true here: the brain is a huge part of your orgasms. The more you keep an open mind, the more you relax and allow pleasure to dictate your experience.


In the End...

Before you scurry off to buy your starter kit and play Doctor, let’s please talk about consent. Consent is not a dirty word, nor should it inspire images of egg shells and tip-toeing. Consent is inextricably linked to respect. Respect builds trust. Trust ramps up vulnerability. Like I said in January, vulnerability leads to profoundly good sex. The criticism and ignorance toward anal sex has had so much to do with the taboo surrounding it. I’d like to keep dismantling this idea that anyone who is even curious about trying anal sex is gross. It’s simply not true.

There is absolutely nothing wrong with healthy curiosity and healthy (safe!) sexual exploration. If anything, it may even open the doors to another sexual awakening. Why not? You deserve that much.