Guide to Butt Stuff: Anal in 8 Steps

People...I like buggery. I like the word, I love the act. Taking it up the butt is one of the most enjoyable acts consenting adults can engage in. But, ONLY if you’re doing it properly. The thing with anal is, for as much as it is enjoyable, it can be equally as horrifying or traumatic if you do it incorrectly. Please don’t do it incorrectly. You don’t want to be that weird mouth breather in the emergency room with a cuban cigar stuck in your colon, desperately trying to come up with a logical explanation as to why. There is no logical explanation. Everyone knows why you’re there.

Whether you’re bored with your current orifices and want to try a new one, or you’re considering committing to a butt-stuff-only sexual regime, this easy, eight step program will have you bumming yourself to orgasms in no time! And if it doesn’t, well that's too bad, we don’t offer refunds.

STEP 1: ADDRESSING YOUR BAGGAGE

Anal can be a pretty daunting prospect for a lot of people. We have a tendency to associate it with a certain level of depravity. For this reason, many people have a lot of issues about trying it.

Many women believe it’s the sort of act that once they've done it, they can no longer consider themselves "respectable". It’s the sort of thing that “sluts” and “tramps” do, not women who want to be wives, partners or significant others. If we’re being honest though, we used to say the same things about sex before marriage and blowjobs.

Likewise, many men of various sexual identities, feel that allowing their partner to penetrate them will lead to them being less of a man. Being penetrated is a shorthand term for a loss of masculinity (ponder the implications of that for women in your own spare time). Men feel that if they let their partner peg them, or penetrate them in any way, they too will no longer be respected. Taking it up the ass is often conflated with being effeminate or emasculated. Because we all know that your butt-hymen is the place where masculinity and dominance are kept. 

There’s also the everlasting fear for hetero-identifying men that even being curious about putting stuff up the butt means that they need to completely re-asses their sexual identity. To which I say, is reassessing your sexual identity necessarily a bad thing? It should be like a quarterly financial review, where you periodically check whether your options have opened up to investing your dick in more diverse orifices. 

At what point did pursuing pleasure, regardless of the orifice it involved, become something for weak people? If you like it up the butt, good for you. Own that. Sexual proclivities should not be a source of shame. If someone wants to judge you for what you're doing with your butt hole, I'm pretty sure that's the point at which you can cease to give fucks about their opinons. 

If you can actually envisage a situation where your partner asks you for something that you think will lead them to respect you less, that’s a fundamentally flawed relationship. A good sex life and a good relationship have to be built on trust. If your partner asks you to explore a new sexual experience, have a conversation. Take the time to really discuss the ins and outs of it (heh). Because if you don't talk about it, you’re doing yourself and your partner a disservice. You’re denying yourself the opportunity to find out why you’re actually uncomfortable with it.

On the flipside though, never let someone tell you that you should be doing a sexual act that you don’t want to. If it’s not a conversation and it’s just a barrage of demands for buttsex, then your partner is pressuring you. You need to call them on that shit. Tell them how they’re making you feel and either tell them why it’s definitively not something you’re comfortable with, or tell them that you'll get there in your own time and that you need some space. If they still pressure you about anal, it might be time to take a long hard look at the relationship.

STEP 2:  GETTING TO KNOW YOU

As any athlete will tell you, training is the most important part of a gold medalist’s journey. Currently your ass identifies itself as an exit. You want it to be more of a revolving door. Therefore your butthole needs to be trained. While it will probably never learn to fetch, roll over or play dead, it can be trained to find pleasure from objects being stuck inside it.

Don’t get me wrong, most butts will already feel pleasure as soon as something is inserted into them. The difficult part is actually getting the rest of your body to catch up with that pleasure. As we’ve established, there’s a huge psychological component to anal sex and it can be incredibly hard to relax your body when your mind is screaming at you that what you're doing is wrong or that it’s going to hurt.

Get to know your butt. It won’t bite…and if it does you have a whole new set of problems. Explore your secret starfish alone and on your own terms. Grab a mirror and go gently, being mindful of the sensations you're experiencing. How does it feel when you touch the inside of your butt cheek? What about your perineum? If you put some lube on your finger and rub it over your butthole, does it feel good? Remember to let go of shame and apprehension and just focus on sensation. 

It might feel like you’re in enemy territory because both you and your butthole are probably slightly terrified of what’s going to happen next. That’s natural. Don’t panic. Remember, it’s just you and Uranus alone together, so explore and plant your flag on this unexplored territory.

STEP 3: LIQUIDS

There’s a few substances on the market that are promoted as being "great for anal". These products are lies in fancy packaging. I’m talking specifically about anything along the lines of “anal ease” or anything that mentions “numbing agents” or “benzocaine”. A lot of retailers will stock and even promote lubricants that have a mild local anesthetic in them. This is wildly irresponsible and makes them bad people. They probably kick puppies when no one’s looking.

Have you ever been so drunk that you fell down a flight of stairs, or walked into something solid and at the time you didn’t feel it, but the next day you regretted every life choice that led you to that moment? Imagine that situation but with your asshole. A numbing agent will do one thing very well. It will make you numb. You don’t want to be numb. For two reasons;

 1) You won’t feel any pleasure

and

2) You won’t feel any pain

You need to be able to feel both. If something hurts, you need to stop. Maybe you’ll readjust and try it at a different angle, or not go so deep or maybe you’ll stop altogether. Either way it’s important that you’re able to make that choice.

Also, if you can’t enjoy how amazing it feels, what’s the goddamn point?!

IMPORTANT: YOUR ASSHOLE IS NOT A SELF LUBRICATING ORIFICE.

YOU MUST USE LUBRICANT!

What you really want for anal sex is a good, high quality silicone lubricant. Don’t cheap out. Get the top shelf stuff, trust me.

If you're masturbating using a toy, it's better to stick to a silicone free lubricant. 

Spit is not a substitute. And whatever you do, DO NOT use a warming lube. 

STEP 4: MASTURBATE

So there was this guy, you might have heard of him, Pavlov. He had a dog. Right now, your butthole is the dog and you’re about to do some science. Both you and your butt might be pretty tense. You know what’s going to happen, you know that you’re about to stick stuff up it, and it’s making you apprehensive. We don’t want that. You'll start to associate sticking stuff up your butt with being anxious and nervous. Not the best combination.

To combat this, you’re going to need to give your front junk some love. I don’t care what kind of genitals you have, I want you to stimulate them before you stick anything up your south hole. Once you’re feeling frisky, but before orgasm, you’ll want to gently insert a toy (we’ll get to the right kinds of toy in a minute). Don’t stop touching your front fun bits. Try and get a bit of a rhythm going between the two so that you’re stimulating both equally.

You don’t have to try and orgasm from this, although if you do that’s awesome. You can remove the toy and have a normal masturbatory orgasm, or you can stop completely if you like. The point of this exercise is to feel pleasure and to associate that pleasure with having stuff in your butt. You will need to do this several times before even considering anal sex. The purpose of the exercise is to get to the point where thinking about having a dick or a dick sized object up there fills you with excitement (not terror). 

STEP 5: TOYS

There are a ton of toys out there, many of them made especially for butts. For some reason though, a lot of people decide that they don’t want special butt-friendly toys. They decide that they’ll just stick any old thing up there, whether it’s just a different kind of toy or a wine bottle or a light bulb.

Do not be this person. Please. The difference between toys that are butt-friendly and butt-villains is simple; a dedicated anal toy will have some form of flared base on it.

The reason for this is that butts are a lot more like a black hole than you thought, and will literally swallow anything they can. If your toy doesn’t have a stopper on it, it will disappear up inside you. What follows will either be the most heart-stopping three minutes of your life as you try and extract it (not that I’m speaking from experience or anything here…) or alternatively the most awkward seat in an ER waiting room you’ve ever had.

Now that you know to buy a dedicated anal toy, you need to narrow it down to what kind. Because there are many varieties to select from:

BUTT PLUGS:

There’s the basic butt plug, which can come in everything from silicone to glass to steel, and be adorned with jewels, faux animal tails or the face of Vladmir Putin. 

Butt plugs are a great beginners toy as they aren’t too daunting to look at and you can purchase “training kits” that will come with three graduations in size so you can upgrade to bigger plugs as you get accustomed to them.  

The best way to use a butt plug is to wait until you’re engaging in sexual activity, either with a partner or by yourself, apply lube, insert plug and then continue with your previous activity. 

If you’re a vagina owner being penetrated by a penis, your partner will notice that you’ll feel tighter and you in turn will feel the extra pressure from the plug which can lead to some pretty explosive orgasms. 

If you’re a penis owner, it will stimulate the area around your prostate, without really going to town on it (which can cause orgasm very quickly). 

ANAL BEADS:

Anal beads are, as they sound, a string of beads. Most of them have beads graduating in size from small to large, but some will just be a chain of beads the same size. They will have an extraction ring at one end, to stop them from disappearing up in your sarlacc pit, and to allow them to be pulled out with control. Anal beads are typically made from silicone and, as with all toys, if they’re made from rubber or jelly, just avoid them entirely.

Anal beads are designed to be moved in and out of your butthole, either by yourself or a partner. This makes them  ideal for using during intercourse, masturbation, assisted masturbation or just fucking around with friends.

DILDOS:

Dildos are a great anal pleasure toy once you’re ready for something of a more substantial size. A dildo is a non-vibrating, normally somewhat lifelike approximation of a dick. Many dildos will come with a suction cup base or are flared out where the balls are, which means they’re safe for anal play. A good dildo will be made of silicone, however you can get some pretty swish looking glass ones (just keep in mind where it’s going if you’re a bit squeamish about seeing where last week’s lunch ended up).

Dildos are pretty versatile and you can use them during intercourse, as a masturbatory aid or just for sexual play. They are for advanced users though, don’t start with a dildo, it’s just going to be too big if you’ve never stuck anything more than a finger up there.

There’s also double ended dildos, which as you can guess is basically one long two headed penis…it’s like cat-dog, but dick-dick. These are fantastic if you have a partner who is also into anal play so you can live your Requiem for a Dream and ass to ass until you pass out from orgasms.

PROSTATE MASSAGERS: 

Contrary to the name, you can use these if you don’t have a prostate. Prostate massagers are kind of like the g-spot toy for penis owners. They’re designed with a curve in them so once they’re inside they push against the prostate, which will stimulate an orgasm. If however, like myself, you do not have a prostate, they still feel amazing and are perfect for masturbation or sexual play.

This isn’t a comprehensive list of anal toys, but it should be enough to give you an idea of what you might like the feel of. Remember to start small and always stimulate your front junk the first time you use a toy or you risk panicking and forever associating that toy with orgasmic failure.

STEP 6: Anal play OPTIONS

So maybe you’ve decided that you’re not quite ready for a dick but you don’t like the feel of toys either. Never fear, there are other things you can do with butts. If you’re a vagina owner and you enjoy having it fingered, there’s a good chance you’ll enjoy the same thing in your butt.

Always start small and slow with fingering and ensure that said fingers have clean, trimmed fingernails before beginning. The last thing you want is a scratch on the inside of your rectum. It’s about as much fun as it sounds.

Alternatively, if you’ve realized that you’re more into the sensations right before penetrating you might be a fan of analingus, or “rimming”. This involves a partner running a tongue around the outside of your asshole. There’s nothing wrong with enjoying giving or receiving this, but it is courteous to ensure that the lucky asshole getting licked is squeaky clean before commencement, otherwise you risk a nasty case of dysentery.

STEP 7: Buttsex

If you’ve skipped straight to this step before reading about preparation, I want you to know that you’re what’s wrong with the youth of today.

Having anal sex, whether it’s with a penis or a strap on, is not something you jump into straight away. It requires a lot of patience and trust between partners and you both need to know that “stop” means stop.

Before being buggered, you’re going to want to take a moment to think about the last time you went to the toilet. If you need to poo, now's the time to do it. If you don’t that’s great. Lube up.

Start small and slow with just the tip, gradually sliding in over time.

When you’re first penetrated, it will feel incredibly intense. If you’ve done your training, it should feel intensely pleasurable. If you’re still a bit nervous, it might feel like you really need to poop. This is completely natural and nothing to worry about. Some people will get their partner to maintain constant movement to combat this feeling, creating micro-thrusts so the penis isn’t just sitting half way in or out like a giant turd. If this helps you, ask your partner to do this, otherwise continue with the slow, incremental penetration.

Once the penis or strap on is 100% inside, congratulate yourself and inform the monarchy, they’ll probably want to send you a letter.

Communicate with your partner about what you’d like next, whether you’d like small thrusts from in deep, or if you’d prefer slow and gentle full thrusts. Do NOT just start pounding away. You’ll get to the point where you’re able to, but you need to build up to it.

At this point, start to develop the rhythm that you’re comfortable with and then increase the speed or depth as you feel ready. If you decide within the first inch that you’re not going to enjoy this or you’re not ready, that’s completely fine. Let your partner know and either continue training up to it or accept that you’re not into anal and that’s okay.

Anal sex can be an intensely, awesome orgasmic experience and it can also be an incredibly intimate trust exercise between consenting adults.

STEP 8: POOP

Let’s not kid ourselves, we all know what this hole is doing during its normal nine to five. It’s expelling your waste and emitting poorly timed farts. So be prepared for the fact that you will, in all likelihood see poop. More than once. Maybe you’ll just see little flecks, maybe there’ll be some on the sheets, or maybe your partner will have a penis or toy covered in the stuff.

It’s something you need to mentally prepare yourself for. It’s something you need to prepare your partner for. There’s actually nothing to be ashamed about as long as both parties are aware of what could happen. If you’re the one giving, don’t call attention to it if you see it and certainly never shame your partner about it (unless you're both into scat or degradation play, in which case go to town). At the end of the day, it’s just shit. We all do it and if you’ve made it this far and are this interested in trying anal, don’t let this be the thing that puts you off.

If it’s something that you’re supremely uncomfortable with, but you still want to try it, you can invest in a home enema kit. These will allow you to flush everything from your colon (not your bowel), leaving the passage clean and clear. However, it can kind of take the romance and spontaneity out of the situation.  If it makes a difference to your confidence and comfort level though, then it might be worth considering.

So there you have it, eight steps to safe and responsible anal pleasure. Think you can handle it? I believe in you. We all believe in you! So forget your baggage, pursue your pleasure and try something new. Who knows, you might like it?

That is all.

You may go now.