How to Get More Comfortable With Anal Sex

All bodies have holes with sensitive nerve endings, and they have things to put into holes. Sometimes it feels good, and some holes take more preparation than others do.
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Collage art by Zoë Ligon, CEO of Spectrum Boutique

Such is the case with anal play, where con­cerns like clean­li­ness, self-consciousness, and phys­i­cal vul­ner­a­bil­i­ty are poten­tial­ly even more pressing.

There are, how­ev­er, many inter­nal struc­tures that make butt stuff feel good. They include the legs of the inter­nal cli­toris or penis, the prostate or ure­thral sponge, and the dense­ly packed nerve bun­dles in the anus itself.

The aver­age Millennial knows what’s up — exper­i­ment­ing more with anal play than pre­vi­ous gen­er­a­tions. If butt stuff has piqued your inter­est, but you don’t know where to begin, this post is for you.

Maybe you’re curious and squeamish

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It’s total­ly under­stand­able, con­sid­er­ing the pur­pose of the rec­tal cav­i­ty. So before I even get into tips and toys for anal train­ing, I want to address the top­ic of cleanliness.

Think of the colon as the living room and the rectum as the foyer.

Generally, poop stays in the colon and only drops down when it’s about ready to exit. A bow­el move­ment and show­er a half-hour before butt stuff is enough for many peo­ple to clear that area out.

[Image: an enema / douche isn't necessary for clean anal sex but it can be helpful!]

If you’re still eas­i­ly grossed out and want a deep­er clean, I’ve writ­ten a sep­a­rate guide to clean anal sex, with tips like:

  • Adjustments to eat­ing habits
  • Resources for anal douching
  • Items to keep on hand for easy prep and cleanup

In a nut­shell, fiber sup­ple­ments, a tow­el, and bar­ri­ers (like latex or nitrile gloves, den­tal dams, and con­doms) help stay clean.

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Plus! If you have long nails and don’t want to trim them before fin­ger­ing, you can stuff a glove’s fin­ger­tips with cot­ton balls for cush­ion­ing. And mas­sag­ing with fin­gers is a great way to get start­ed with butt stuff.

Before starting anal penetration

A key thing to keep in mind is that the anus has two sphincters.

The outer sphincter is easy to consciously relax, but the inner one takes a bit more finessing.

Mindset is vital, so take some time to wind down. Deep breath­ing and arousal help the pelvic floor relax. As with vagi­nal pen­e­tra­tion, anal pen­e­tra­tion is much eas­i­er when you’re already relaxed and aroused, so I sug­gest exter­nal stim­u­la­tion first.

Personally, it’s hard to go wrong when start­ing with a few cli­toral orgasms via a recharge­able wand.

An exter­nal flick­ing toy like the Fun Factory Volta or Fantasy For Her Ultimate Pleasure can also feel espe­cial­ly plea­sur­able at the anal open­ing. And, of course, rimjobs from a part­ner offer sen­sa­tions that toys can’t quite replicate.

Personal lubricant is a must!

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For butt stuff, I generally recommend water-based lube with a gel-like consistency.

Try Sliquid Sassy or Hathor/SUTIL. They're slip­pery while com­pat­i­ble with all mate­ri­als, and you can “refresh” by spray­ing water on.

Oil-based and silicone-based lubes last longer, but you have to consider what you’re using them with.

Oil degrades rub­ber (think con­doms, TPE, and TPR), and liq­uid sil­i­cone can degrade sol­id sil­i­cone. So if you plan on using sil­i­cone toys, stick to a water-based or oil-based lube.

Make sure you lubricate the anus and whatever’s being inserted.

Lube shoot­ers are great for that. As an addi­tion­al safe­ty reminder, nev­er use anal numb­ing creams. If your rec­tal area feels pain, it’s a sig­nal to do some­thing dif­fer­ent­ly or stop, and that shouldn’t be ignored.

Things to try with toys and fingers

The area is packed with feel-good fine touch recep­tors. So, as men­tioned before, it helps to pair exter­nal anal stim­u­la­tion with anoth­er activ­i­ty before even think­ing about pen­e­tra­tion. Think, for exam­ple, of oral while cir­cling the open­ing with a fin­ger or light­ly tex­tured plug.

When starting penetration, start slow, of course. By slow, I mean slooow. Slower than you think.

Like a mil­lime­ter per sec­ond as you relax and increase pres­sure. But once about an inch is in, hold it in place. Don’t start thrust­ing. Don’t put the rest of the object in. Just keep it there for a minute. Clench and relax around it to get com­fort­able with its presence.

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Dilator kits are a rather under­rat­ed way to warm up to anal sex!

Then slowly twist it or revolve it in circles while inside.

The cir­cling motion “tricks” the anus into per­ceiv­ing the object as a lit­tle wider than it actu­al­ly is, help­ing to relax and get ready for more. Then press hard­er, add lube if there’s resis­tance, and insert more of the length.

From here, you can press against the front rectal wall to massage the G‑spot or prostate.

Think of it as mas­sag­ing behind where the pubic bone is and a lit­tle bit deep­er. Fingers are fan­tas­tic for this, as are curved toys like the nJoy Fun Wand.

(Looking for begin­ner butt toys? Read my guide to com­mon char­ac­ter­is­tics of the best toys for anal play.)

The best positions for enjoying first-time anal sex

Many posi­tions can be adapt­ed for com­fort­able anal play—much of it varies with angling and leg posi­tion­ing, so a sex pil­low can make a big dif­fer­ence. Two types of posi­tions stand out for begin­ners, though.

If the receiving partner is on top, they’re in control of the thrusting depth and speed.

And know­ing that they can start super slow and shal­low can go a long way in putting their mind at ease.

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Collage art by Zoë Ligon

As well, it poten­tial­ly leaves both part­ners’ hands free for exter­nal stim­u­la­tion. There’s plen­ty of room to use a wand mas­sager on the receiv­ing part­ner. Still, if you’d pre­fer a petite and non-intrusive vibe, the Hot Octopuss Amo and Dame Pom are fan­tas­tic options.

Spooning and side-lying positions are also ideal for anal because much of the receiving partner’s weight is supported.

Think about it: if some­one has mobil­i­ty prob­lems or is full-figured, it may be a bit hard­er to stay ele­vat­ed and sus­tain shal­low pen­e­tra­tion when on top.

In any case, if you know you want to lim­it pen­e­tra­tion depth, an Ohnut can take up room on a dil­do or penis shaft and buffer some of the length.

Wrapping it up

Butt stuff is the great equalizer—everyone has a butt, and everyone has potentially sensational internal erogenous zones.

Exploring the area may take some time and effort, but many peo­ple of all gen­ders find that it brings their plea­sure to new heights.


[This is a repost of an arti­cle orig­i­nal­ly writ­ten by Super Smash Cache for Spectrum Boutique. This ver­sion has some mod­i­fi­ca­tions to fit my website's layout!]

2 Responses

  1. Frankie says:

    As a trans­mas­cu­line per­son, I some­times get dys­phor­ic when read­ing about prostate play. I real­ly like how you grouped the prostate togeth­er with the ure­thral sponge, so I didn't feel like my body was miss­ing something. 🙂

  2. Jimena says:

    Thanks for this guide <3

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