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Anal Play From A to Z

Are you ready to try anal play?

(Or maybe you just want to be super prepared when the topic of anal comes up?)

Either way, here’s a list of things you can’t forget if you’re thinking of getting/giving some booty love.

Before we start:

Anyone - independent of sex, gender or sexual orientation- can practice and enjoy anal play, because everybody has an anus*. So, to make it as inclusive as possible we’ll use the gender neutral terms TOP and BOTTOM.

TOP: the one who is doing the stroking/licking/penetrating.

BOTTOM: the receptive partner.

*although anyone can enjoy anal, it certainly doesn’t mean everybody has to!

Anal play

Most people associate anal sex with ‘penis into rectum’ which is really just one of many forms of anal contact (see Rimming, prostate massage, pegging, toys, basically A to Z). Thus, our preference for the broader term Anal Play.


There’s no Anal without Anus... So make sure you know the basics it’s important to know who you’re visiting before heading for the back door.


Anal intercourse without a condom.

[see Unprotected Anal Sex]

Barriers for Butthole Bliss

We’re of the idea that there’s no Butthole Bliss without Safer Sex Barriers. Being that the number one concern for people considering anal sex is “uneasiness about making a mess”, barriers can help both partners feel more relaxed about keeping things clean. Plus, using gloves and condoms allows fingers, penises or toys to slide in more smoothly. They also protect both partners from sexually transmitted infections [see Unprotected sex].

  • Condoms: not just for penises, you can use them to keep your toys clean. The female condom is another option.

  • Gloves: they keep the hands clean and smooth over any rough areas (make sure you don’t use latex gloves with any oil-based lube because it may break them).

  • Dental dams: thin sheets of latex or nitrile that are used in some dental procedures. They can also be used as a form of protection for cunnilingus and analingus [see Rimming]. Dental dams are available at lots of sex-positive toy shops, but you can also make one out of a condom by unrolling it, snipping off the tip and then cutting down the side to form a rectangle. Another viable option is to use plastic wrap.

Be sure to use lots of lube on the outside of your condom, gloves and/or dental dams [see Lube].


A crucial component to pleasurable and pain-free anal play.

Quick communication tips:

→ Tops: reassure the bottom that it’s ok to ask for a break, more/less lube, genital stimulation, or for you to stop at anytime.

Stay connected: the top should constantly check in with the bottom about what feels good and what doesn’t, how fast or how deep to go.

→ The bottoms opinion ought to prevail [see “Your body, your rules”].


Explicit, informed verbal approval after negotiation,

a confident and secure “YES!”. It is the bedrock of sex and relationships.

Double anal

Simultaneous penetration of the anus by two dicks (or two dildos - see Toys).

Double penetration

One dick/dildo in the vagina and another one in the rear end at the same time

(can also be two penises in the same vagina at the same time).


Prostate pleasure expert Charlie Glickman says it can be really helpful to play with your own ass before you play with someone else’s.

In preparation for anal, then, you might want to try *carefully* inserting your finger up your bum while in the shower (thus teaching your anal sphincters to relax).

Other ways of exploring: try masturbating with an anal toy [see Toys] or ask a partner to lube up a clean finger and gently insert, pushing very softly and slowly.


The injection of liquid into the rectum and colon by way of the anus.

[a.k.a. Anal douching]

If you have a good diet, regular bowel movements and take a shower before play, there shouldn’t be poop in your rectum. However, some people like to have an enema before butt sex as it makes them feel more comfortable and confident. We say, whatever works best for you is fine, just look into enema safety before giving yourself one.

For example you can look at this video on How To Anal Douche Properly!


Putting a whole hand up somebody else’s butt.

It’s one of the most extreme sexual acts that one person can allow another to do to their body. Anal fisting is a potentially dangerous sexual practice and beyond the scope of this article, but we highly recommend the Ultimate Guide to Prostate Pleasure

and The Ultimate Guide to Kink (chapter 10) if you want to learn more.


Tiny cuts in rectal lining.

The most common injury resulting from anal penetration, they are usually minor and generally heal on their own [1]. The risk of such injuries increases when people use unsafe objects as well as with drug & alcohol use.

[1] always check with a physician when in doubt.

Getting started

“Being turned on usually makes anal play a lot easier and more fun. The more turned on you are, the more your brain is likely to interpret new sensations as enjoyable.” Charlie Glickman.

  • Your first few times, don’t go too far or too fast (the anus is a muscle that needs to be worked up to having larger objects inserted).

  • Sex educator Tristan Taormino suggests two fingers MAX for first-time anal penetration.

  • For some people, stimulating the penis, clit or vag can help open the butthole up.


  • Shower before play, wash the anal opening with a mild soap, rinse well.

(A good soaping in the shower should make most anuses sparkle, remember that the rectum is not usually a storage space for poop -see Enema for more info).

  • Put a towel on the bed to keep the sheets from getting dirty.

  • Keep baby wipes nearby in case you need to wipe up.

  • Clean your toy (before and after) and cover it with a condom (during).

  • Wear gloves to keep your hands clean [see Barriers].

Extra tip: Light some incense or a scented candle if you’re concerned about odors.

If it hurts...

… don’t do it! Anal should never cause you pain, if it hurts you are doing something wrong (unless that’s what you are seeking, in which case please be careful).

Although, when you are just beginning to try anal play, you are likely to feel things you’ve never felt before. So it’s important to differentiate between strange or unusual sensations and painful ones.


Journey to the center of the earth

You want to try it but need some courage to get you there? Perhaps Verne can inspire you to explore new territories (lol).


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The people, practices and communities that move beyond traditional ideas about sex to explore the edges of eroticismTristan Taormino.

It’s an inclusive term that covers BDSM (B/D: Bondage, Discipline; D/s Dominance and submission; and SM: Sadism, Masochism), sadomasochism, kinky sex, role play, sex games, fantasy, fetish, and other alternative erotic expressions.

Even though #buttholepleasure has found its way into mainstream culture, and is becoming a rather common practice, anal penetration is still somewhat of a taboo subject outside the gay and sexpositive communities.

However, some people find this “naughty” or “forbidden” factor a huge turn-on. Anal, therefore, can also bring variety to a person’s sex life by opening the door to unexplored fantasies and role play.

Lube (lots and lots of lube)

3 things to REMEMBER about Lube:

1. LUBE is necessary in any type of anal play because the anal opening is not self-lubricating

Anal without lube is like a water slide without water,

it’s not going to work and it’s likely to hurt.

2. Oil can weaken the latex in condoms and gloves so, unless they’re not made out of latex, it’s always better to use water-based lube.

3. Lubricant can be a source of disease transmission. Therefore, make sure that any lube that’s been touched is never used with another partner.


• “Only gay men like to be penetrated”

People of all genders and orientations enjoy anal play. Since the anus is full of nerve endings lots of people feel awesome when it’s stimulated, whether they’re gay, straight, lesbian or bi. For folks with prostates, being on the receiving end of anal sex can be a great experience that leads to mind blowing orgasms [see Orgasm, Pegging & P-spot].

Also, take a look at this chart:

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By katherine Killeffer

(What more evidence do you need?)

• “Liking anal sex is weird”

What is considered “weird” or abnormal is always changing, especially when it comes to sex.

Just as there’s nothing wrong with liking anal (people have been doing it for a veeery long time), it’s also OK to not like it. Everyone’s comfort and pleasure is different. That’s what makes it sex so interesting.

• “Anal sex will damage your rectum”

The idea that the sphincter can become loose over time is not backed up by medical fact. Lots of people enjoy anal play with no long-term ill effects.

Anal sex is classified as a "sexually risky behavior" because anuses are delicate [see Anus]. Penetration does involve some risks but you can minimize them by informing yourself and taking all the necessary precautions [see Barriers & Unprotected sex]


Trim them! Wash ‘em.

“When it comes to the rectum, jagged fingernails are weapons of mass destruction.”


Prostate stimulation can create very unique sensations and very powerful orgasms. A number of men have described it as [2]:

“An intense feeling of arousal”

“Ecstasy unlike any other sexual experience”

“Deeper, fuller, more encompassing pleasure”

“Gets me harder than any other stimulation”

“The gateway to a full-body orgasm”

[2] you can find these and other descriptions in the Ultimate Guide to Prostate Pleasure.

P-spot: The Prostate

The prostate is part of the male reproductive anatomy (of course, trans women and other gender nonconforming folks can have prostates too!). This accessory sex gland contributes a portion of the fluid that makes up semen. The prostate sits beneath the bladder, above the bulb of the penis, surrounding the urethra, a few inches inside the perineum (the area between the testicles and the anus).

People are now talking about the prostate as the ‘male G-spot’, or P-spot, to highlight the fact that people with penises have a very powerful internal pleasure button to be explored.

To learn more about prostate massage we recommend this read.


The insertion of penis-like objects (such as dildos) into the straight male butt.

Click here to learn How Pegging Can Help Save The World.

For more visual examples you can check our porn recommendations. [See XXX]

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Queen song

To get that ass shaking and relaxing…

And because music is lubricant for the ears.


Slang word for kissing ass [a.k.a. Analingus, Rim Job]

It means sticking your tongue up or around your partner’s anus.

[To learn more go to: Barriers & Unprotected sex]


The terminal part of the intestine from the sigmoid colon to the anus.


No matter what you are putting inside your butt, it needs to go in very slowly and come out very slowly. Otherwise, extreme discomfort and even physical damage might result [see Fissures].


Any kind of sex that is declared illegal by local statute. In some areas, it can be oral sex or regular intercourse, in others, specifically anal sex.

(Anal) Sphincters

Either of two sphincters controlling the closing of the anus:

A: an outer sphincter of striated muscle extending from the coccyx to the central tendinous part of the perineum and surrounding the anus immediately beneath the skin—called also external anal sphincter.

B: an inner sphincter formed by thickening of the circular smooth muscle of the rectum—called also internal anal sphincter.

Toys for anal play, because:

Unique textures and sensations = yummy

Many shapes, colors and sizes = fun

Flared base = safe

Great for solo sex = score

  • Vibrators: apart from feeling great they help relax the sphincter muscles, which makes them quite popular for anal play. There are battery and electric vibrators, the first are less expensive and the later more durable.

  • Butt plug: smaller dildo-like objects made specifically for the rear end. They don’t give much prostate stimulation but are great for getting the asshole warmed up for motion or larger objects.

  • Dildos: long, generally smooth, great for penetration if they have a flared base.

  • Strap-on: for hands free activity, consists of a harness and a dildo.

  • Anal beads: five beads on a string (they can be small as mothballs or as big as golf balls), to be pulled out as orgasm is beginning. It’s smart to encase them in a condom before inserting, considering they are difficult to fully clean.

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Unprotected Anal Sex

“Straight or gay, single or married, monogamous or slut, you are always wise to use a condom when having anal intercourse. The reasons extend beyond concern about AIDS. It is just as much to keep the male from getting possible prostate infection as it is for protecting the woman.” [3]

Unprotected anal sex is the highest risk behavior for HIV transmission as well as other infections due to the fragile, absorbent tissue of the anus and rectum.


  • Oral-anal contact (rimming) can transmit intestinal parasites and some STI’s .

  • The receiver or bottom is especially vulnerable in anal penetration of contracting STI’s.

  • Tops who have a penis are at greater risk of prostatitis, since bacteria can enter the urethra and travel up to the prostate.

  • Vagina owners can get pregnant from Anal Sex, so it’s definitely not a viable option of birth control. [also, see Vagina]

[3] Paul Joannides, Guide to Getting it On


Keep anything that has touched an anus -tongue, finger, glove, condom, toy, penis, you get the picture- out of the vagina!

Vagina to ass? great

Ass to vagina? No, no, no.

“Bacteria from your butt can wreak havoc on your vagina” Girl Sex 101.


What we think of as traditional or conventional sex.

If you are not into kinky stuff [see Kink], don’t worry: you can do anal in a way that is totally vanilla. Anal can absolutely be sensual and intimate without any suggestion of dominance or submission.

Warm it up

Cold makes muscles tense up, and your butthole is a muscle. Consequently, it’s a good idea to keep not only the room temperature but also your hands & toys (especially if they’re made of metal or glass) nice and warm.

XXX Butt Porn

Maybe you have to see it to believe it? Here’s some good ol’ anal sex porn to watch:

Your body, Your rules.

It’s going to be very hard for anyone’s butthole to relax if they don’t feel comfortable and in control of what happens to their body.

Ziggy Stardust

Bisexual alien rock superstar

… patron saint of butt pleasure?

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Zzz… The end?

Orgasm, or climax, is usually the marker for the end of vanilla/traditional sex. But, when it comes to anal play, orgasm shouldn’t be our main objective (more like a pleasant byproduct if/when it does occur). Even though both vagina and penis owners can potentially orgasm from anal penetration, it’s not always the case– even less so in your first attempts– and expecting it to happen can put unnecessary pressure on both partners. There are times when the bottom senses they need to stop or the top decides they can’t continue, which doesn’t mean you can’t both get off afterward (with or without each other’s help). wink wink.


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