Everything You Need to Know About Anal Sex


Anal sex – or anal play – is an activity that many couples enjoy incorporating into their sex lives. While it isn’t exactly a “standard” addition to a sexual relationship, statistically, most couples incorporate some form of anal play (finger stimulation, rimming, toy play, or penetration) into their sexual rotation at least occasionally. While anal sex is definitely not for everyone, it could be, with the proper education to enhance pleasure and decrease discomfort. There is much to learn about anal stimulation, so if you have been thinking about exploring anal play or have already had it and want to make it even more enjoyable, then read on.


For many people – probably more than not – a huge deterrent to exploring any type of anal stimulation is that it is said to be painful for the receiver. The loads of misinformation regarding anal sex has led so many women (and men) to shy away from anal play simply for the fear that it will hurt. Or, perhaps anal sex was attempted and due to being misinformed or having a partner who was not patient and caring, anal sex WAS painful and therefore, there is no desire to try again. No one really wants sex to be painful, right? Well I am here to tell you; anal sex shouldn’t hurt – ever. If it does, then there is something missing from the equation.

Here is the first component in having anal sex which is pleasurable, and not painful – LUBE. There is no way that you should ever being having anal sex (or anal stimulation in general) without lubrication. The anal canal is not self-lubricating, which means that anal sex will not be smooth or feel good unless some lubricant is added. Furthermore, the tissue (skin) in the rectum is fragile, and can rip or tear without caution, care and lube. The biggest reason that anal sex becomes painful is a lack of lubrication. Anal sex without lube is like getting an internal rug burn – it hurts! You can never have too much lube. You should lube his penis (or finger), any toys AND you should put some lubricant up inside of the anal canal via a finger. You also should not be afraid to re-apply lubricant so that the pathway stays nice and slippery.

People really do not seem to see how important lubricant is for anal stimulation and penetration. Nor do they seem to know what types of lubricants are available, and which ones are the best to try. In my blog, Slippin’ and Slidin’ Down Anal Ave, I discuss, in-depth, lubricants, types, and which ones ARE best for anal sex. Check it out!

There are some lubricants that are made especially for anal play, or are the best to use for anal play. A quick and dirty list of those products is right here:

*Universal TooTimid Lube

* Swiss Navy Anal Lubricant

*PJur Original Body Glide

So, lesson number 1 in having pleasing anal play is to remember that anal sex shouldn’t hurt, and to avoid the pain you need lube.
I am sure that you realize that the anal canal is used to expel feces (poop) from the human body. It is an exit-only canal that truly was not designed to have objects placed up inside. However, there are many preparatory steps that can be taken to help make anal sex or stimulation fun, pleasurable, clean and not painful. We do prep for standard intercourse too sometimes, right? We clean ourselves up, perhaps wax or shave, we get lubricants prepared – in short, we prepare our body for the event. With anal play this is even more beneficial.

Cleaning the playzone. We have already established that the anal canal is what helps feces exit the body, so it stands to reason that sticking anything up there, or licking the anal opening (rimming) can be a bit dirty if the playzone is not properly cleaned, right? From the giver’s standpoint, playing down there without worry is a huge benefit to having a pleasing experience. There is bacteria present that shouldn’t get into her vagina if possible, so the cleaner the better, to avoid any cross contamination.

From the receiver’s point of view, knowing that this area is as clean as possible is important for worry free play. So, the first rule of prep is to, at least, clean up the nether area with a soapy washcloth or wet wipe to get any debris that may be hanging around down there. Also, stick the cloth or wipe up into the rectum via a finger to further clean the area. This will eliminate and remnants of bowel movements, eliminate odor, and make the experience overall cleaner.

Are enemas necessary? For some people, the idea of having anal stimulation is greatly deterred by “the mess factor.” Meaning, feces leakage. They do not feel that simply washing with a wet wipe is going to clean them thoroughly enough. Or, they have attempted anal play and it has been less pleasing because their anal canal had a blockage (poop) that made it more difficult to achieve anal penetration. So, many people wonder if performing an enema (when you clean out your lower bowels via a solution that is forced up into the anus, and then released, eliminating any feces present) would be beneficial to more comfortable anal play. I term this “advanced prep” because this is for the hard-core anal players who really want an extremely clean play area, or are going to engage in full-on anal penetration, and not just finger stimulation. I discuss the benefits (and strategies) for this advanced prep in point six of my blog, 

How To Prepare For Anal Sex



Butt plugs have multiple purposes for anal play and pleasure. They can (and should) be used to prepare and gently expand the anal canal for anal stimulation and penetration and they can be used, on their own, to provide anal stimulation and pleasure. Butt plugs are specially made to provide a smooth insertion into the anal canal to expand the opening and allow the anal muscles to expand and relax. They are also made so that they cannot be lost inside the anal canal (if there is no stopper on the end, it is possible for the item to be sucked up into the anal canal). When used prior to anal penetration, a butt plug will allow the receiver to relax into anal play and to be better prepared for actual anal stimulation, and when the penis or toy is inserted there will not need to be as much stretching of the rectal muscles to accept it. Beginner anal plugs. It seems sensical to ease an anal newbie into anal play before attempting full on anal play, right? Butt plugs are absolutely wonderful for achieving this. Many beginner’s anal play sets come with a set of 3 anal plugs that range from very small (perhaps a finger in diameter) to a bit larger (2 fingers in diameter). Using a beginner’s plug set for newbie play has the following benefits:

1. It gently eases the recipient into the experience of anal penetration.
2. It allows for greater control of the object being inserted. The depth, speed and lubrication level can be monitored more specifically.
3. You can begin with a smaller plug, then gently increase in size, until the largest plug is used, thereby gently easing the receiver into greater sizes.
4. You can give other stimulations during play, such as oral sex, to even more relax the recipient and make the experience positive and pleasurable.

If this sounds like something that you could benefit from, here are a few of the best beginner anal sets to try out:

* Silicone Anal Plug Set
* Crystal Jellies Starter Kit
* Anal Training Kit

Butt plugs for play. Sometimes we don’t think about using a butt plug just for anal pleasure, especially if we are not in a relationship at the moment and are playing solo. The truth is, but plugs can bring pleasure on their own, used during intercourse, or as foreplay with a partner. Many people do not really know HOW to incorporate a butt plug into their sexual play. If you find yourself in this situation, perhaps take a look at my blog, How and Why to Use A Butt Plug.

Once you decide to try an anal plug during sex, foreplay, or masturbation you may wonder what type to get? There are standard plugs, silicone plugs, vibrating plugs, glass plugs and all different shapes and sizes. It really is up to you and your personal preference and comfort level. I, personally, love vibrating plugs. In fact, you should check out our Best Vibrating Plugs, if you are interested. It is important to note, never use a toy that is not designed for anal play up the anal canal. Anal toys are made specifically for anal play, such as these:

* Dare's 10-Function Anal Plug
* Pretty Jewel Butt Plug
* The Rook Tunnel Plug
* Hearts Of Love Butt Plug


Butt plugs are not the only anal toy out there. In fact, there are many different types of anal toys, and each one will give you a different sensation during anal play. There is actually a lot to be said about anal toys, how to use them, how to pick one, how to incorporate them into sexual situations. For a basic primer on everything anal sex toy, see my blog, A Primer On Anal Toys.

Anal beads: Anal beads are basically different sized beads (think marbles) that are connected on a string or are molded into a very, very thin dildo-type toy. You insert these into the rectum during or before foreplay or sex, and then take them out at the time of orgasm, which increases the intensity. Popular anal beads are:

* Silicone Heart Anal Beads
* Double Bubble Pleasure Beads
* Mega Booty Beads


The most fascinating thing about anal sex is that it is an activity that can, and is, pleasurable for all people. Male or female. Gay, straight or lesbian. No matter your gender or sexual orientation, anal play is universally exciting and pleasing. A common misconception is that men who want anal play must be homosexual. Nothing is further from the truth! What feels good, feels good. Many people ask, “WHY, should I have anal sex?” I address this in my blog, What Do Men and Women Get Out of Anal Sex. In short, though, anal sex, when done correctly, feels amazing for males as well as females. The anal canal is exactly the same for both males and females, so the pleasure is the same. Males do have a prostate that can be stimulated during anal play, which makes it possible to experience even greater pleasure! Keep this in mind, guys, when you are asking your partner to engage in anal sex. What is good for the goose, is good for the gander.

Prostate massagers for men. Prostate massagers are a wonderful item for men who want to explore anal play that is specifically designed just for them. These massagers are designed with a curved end that will hit the prostate when inserted properly into the anal canal. Many men report that any orgasm they achieve when a prostate massager is inserted is more intense than without. Who could argue with that? If you, or your man, are interested in trying out a prostate massager, here are just a few of the best ones:

* Temptation Silicone Probe
* My 1st Anal Explorer Kit
* Vibrating Prostate Stimulator
* Twisted Rimmer Rotating Massager


Contemplating anal sex usually brings up a lot of questions. Questions that are easily answered. These questions are good to ask and good to know the answer to. Some common questions are:

- Will it hurt?
- Will I poop myself?
- Will it feel good?
- Will it stretch me out too much?
- Will I get hemorrhoids?
- Will I bleed?
- Will I need diapers after a while?
- If I like anal, does it make me gay?

These are all things that are important to know when contemplating a new sexual activity, right? Since these questions, and so many more, come up, I have written a few blogs that answer them in detail. If you are unsure about anal sex, or see some of your questions posted there, then give my blogs a gander:

- 8 Things To Expect
- 7 Things They Don’t Tell You
- What’s The Big Deal?
- What People Never Tell You!


Anal sex is not an activity that every person likes. Whether you are a male wanting a female partner to try it, or a female wanting your man to allow a little anal action, bringing up these desires can be hard, especially since there is such fear and stigma surrounding anal sex. While having fear of the activity may ruin it from the beginning, the best way to go about wanting anal sex is to just have an honest conversation about it with your partner. Trust is essential in any relationship and is very important when talking anal play. If you have an open and trusting relationship with your partner, then just sit down and tell them of your desires to try it.

Knowing the information is key to convincing your partner to try anal sex. All the information given in this blog can be extremely helpful in explaining your desires, the pleasure that can occur, as well as addressing her (or his) fears. Knowing how to respond when your partner asks, “But will I poop myself?” is important to creating a safe feeling. There is also a good way, and a bad way, to bring up wanting to have anal sex. My blog, 5 Ways To Get Your Partner To Try Anal, addresses some of these ways.

Note for the women. For any women who are contemplating having anal sex and who wonder, exactly, what a woman who has had anal sex thinks about it, well, read my blog 10 Thoughts She Has During Anal Sex, and you can read my personal thoughts and feelings while having anal sex. Personally, I love anal sex, but it has taken me years to get completely comfortable with it. Having a partner who I trust, knowing how to make things easier, finding a lube that I love, and being relaxed during anal play have all helped me to becomes an anal sex aficionado.

Note for the men. Hey, guys, if you are wondering about having some anal play (penetration or just stimulation), just know you are not alone. Many men enjoy anal play on a regular basis. If you are afraid that your female partner will fear you are “homosexual” if you request this, never fear, just direct her to the information contained herein. If you have been asked by your partner to try anal, and are apprehensive, then also take comfort in the words found here. Anal sex can be extremely pleasurable for you, and your partner.


Now that you have heard the suggestions for lubricants, prepping, toys, plugs and even prostate massagers. It is time to go forth and have good anal sex! Following the advice here, trying to have the most fun you possibly can, while making sure that you truly are mentally prepared for anal sex will ensure you have a satisfying experience. Now, all that is left to do is to experiment with what you like and don’t like. Find a position that is fun, shop for some anal toys to use, discover your favorite anal lubricant. All of this will come with time.

So, for the ending here I will leave you with two blogs to help you to go forth and enjoy experimenting with anal sex. One with some last minute quick tips, 5 Steps To Have GOOD Anal Sex, and one all on the best positions to try, 10 Great Anal Sex Positions. Go, have fun. Have anal sex!

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TooTimid Angela - January 2, 2020

@BILL – Sorry this was missed! It is 100% okay to have anal sex every night as long as whoever is receiving fully enjoys it, wants to have anal sex that frequently and doesn’t experience any sort of pain or soreness, just as other forms of sex! -Angela

BILL - October 16, 2019

Me and my wife love having anal sex every night is that ok.

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