Kinky Dungeon · Survival Guide

Anal Survival Guide

For what seems like an ages ago, I wrote this little piece called ‘Sub Drop Survival Guide‘. I haven’t had as severe subdrops since, or it might be because I’m not that scared of them anymore. I can now be sure that Sir Atticus would be there for me. Although self-doubt and angst still eats at me for time to time, I now am more capable to deal with it mostly myself. There are tons of challenges when it comes to the D/s relationships, some physical, some mental, for both the Dom and the sub. So as I got the inspiration to write some tips for anal training, I thought to myself that why not make this into an on-going ‘Survival Guide’ series! 😀 As you probably might have guessed from the title of this post, this is not written in a deadly serious manner. D/s, with its whips and chains and tears and blood, is supposed to be fun at the end of the day. So this is not going to be a step-by-step guide, or even a guide in a strict sense of the word, but these are stuff that helped me, a girl who hated anal sex, to learn to take it and to eventually love it. Also, this is not solely written for D/s couples, but also for vanilla couples who want to try something new. *gasp* Do you smell that? No, not making a poop joke in the middle of a post about anal sex. I smell the opening (pun intended) for yet another list! So, without further ado, here’s a top 10 list of things to help you tap that ass! XD Sorry about that, I’ll stop now. No promises though.

1. Mental preparation

Before actually doing it, couples need to talk about it first. There are tons of taboos and stereotypes surrounding anal sex. One thing is for sure, is that it can be a very intense sexual experience that if done wrong, could be very traumatizing. Like everything else in a successful relationship, it has to be made certain that anal sex is something that both of you want. In most cases, just like in my case, it’s the one taking it who is hesitant. Because it sounds like it’s dirty. Because it sounds like it’s painful. Because isn’t one hole enough. 😀 Reasons are many and all of them needed to be addressed and all fear soothed out. The most important thing to remember is, not everyone likes anal sex. It’s great if you both decide to give it a go, but if at the end of the day, your partner still doesn’t like it after giving it a good go, do not make him/her feel guilty about it. And boys, the worst thing you could say to your girl is ‘my ex-girlfriend/sub loves it, why don’t you’.

Anal seems to be more or less a stable in the BDSM community. Some would like it more, some like it less, but most of us do it. For as little as I used to like anal, after getting into BDSM, I knew I needed to do it eventually. And I had my need to serve to drive me forward, so the mental part is covered for me. The next part is physical preparation.

2. Physical preparation 

And by physical preparation, I mean mostly the matter of cleanliness. One of my biggest worry when having anal was naturally poop. It would stress me out that what if I fart or poop all over the place. It used to be so stressful that I couldn’t possibly enjoy the whole ordeal even if I could take the pain (which I could but very very poorly). For some reason, it didn’t cross my mind to do an enema, enemas for cleaning purposes seem so weird outside of BDSM. After getting into BDSM, enemas became the most natural thing to do in preparation for anal sex. Enema kits can be bought from online, or your local pharmacy. There are tons of instructions to be found online, I have written my own tips and tricks concerning enema too. Performing enema is one of the best way to ensure cleanliness, in addition to taking showers to assure you are clean in and out. 😀 But in the end, it is just poop. Nothing that can’t be washed with some water and soap. I have experienced a failed enema with Sir Atticus too, and cos He didn’t make a big deal out of it, more like in a manner of ‘shit happens’ (yes, He’s way bigger on puns than I am). Since then, we have had a several shitty incidences on hand (get it? XD) but it’s more like a bonding experience than any life or dead situation.

3. A quick anatomy lesson

Okay I have no idea what I’m talking about. I have done zero research, this is completely based on my own observation and experiences. So this can be wildly inaccurate and I turn out to be a freak of nature. XD But before someone drags me to be tested, I’m stating the following as facts. 😀

The main area in your asshole that is going to hurt like a motherfucker in every attempt at sticking something into your butthole, it’s going to be the entrance. The little gate which is naturally tight, cos otherwise you would be shitting your pants all the time. That’s why the entrance is always going to be the area that hurts the most, which kinda sucks cos many would be discouraged to go any further when it’s hurting that much in the beginning already. Which conveniently brings us to the next topic.

4. Plugs plugs plugs

Julien Snelling Rosebud LIght Beginner’s butt plug

Ever wondered why anal plugs are shaped like they usually are? The pointy top is for easier insertion, the widening gradually is for minimum pain and then the narrow part is for maximum comfort for longer usage and finally the wide part to prevent the plug to get lost in the black hole and for easier removal too. If you are inexperienced with inserting an anal plug, I recommend inserting it while you are on your knees, legs spread wide. Or if you find it harder to reach, then do it standing up.

And then a few words about choosing your first anal plug, the key word is start from small. Like really small. My first plug was this wee red thing quite similar to the one shown in the photo. It has the diameter of roughly one inch aka 2.5 centimeters. Trust me, if you are new to anal, even this size would look intimidating. For first attempts, unless you really want to include your partner, insert it yourself. Because then you can do it as slowly as you want. Prep it up well with lots and lots of toy-friendly lube. For the first time, go slooooow. Get a firm grip of your plug, and slowly but firmly push it in your asshole. When the widest part of the plug is just inside the entrance, it’s going to hurt but keep pushing it in and I promise you once it’s completely inside, so that the entrance rests peacefully in the slimmest part of the plug, you won’t feel any pain. It might feel odd to have something foreign in your body, but there won’t be any pain. I actually recommend using aluminum plugs for your first, cos they make it small and there won’t be much friction like with silicone plugs. Plus aluminum is way more easier to keep clean.

Be patient with anal plug training. Use the small one for as long as you need to feel comfortable with it. Try masturbating or having vaginal sex with it in, wear it a bit longer to do your everyday chores. When you’ve gotten used to it, it’s time to go for the bigger size. For long period usage, I still recommend aluminum plugs as they stay in without much effort. But for preparing for the actual intercourse purpose, I actually recommend glass plugs. Their slimmest part is usually wider, as to get you more used to thr girth. But after you are trained to be used to the sensation of anal plugs, moving on to bigger glass plugs would bring back the initial pain. Because your asshole entrance wouldn’t get a break, so to speak with the wider glass plugs, it is going to hurt even if the plug is completely in. Sometimes, depending on your position, your muscles would try to squeeze it back out. Just keep it in with your fingers, take deep breaths, the pain will subside in a bit.

My own training consists of practicing doing enemas, inserting plugs and glass dildos for around ten days. But I have to stress one thing, even if a girl/sub is trained for anal, that doesn’t mean she/he is going to be able to take your penis/strap-on right away anytime you want it. Being trained for anal means (imo) that someone is prepared for the pain and sensation that anal is going to bring, opening up upon each attempt to have anal sex is still required. Unless it’s anal punishment, but that is a completely different topic and a story for another day.

5. Don’t be stingy with that lube

I myself don’t use the traditional lube, cos I have yet to find one that won’t dry up quickly or cause a mess. Coconut oil was recommended to me and upon trying it, I’ve been a firm believer since. Coconut oil is natural and always toy friendly, and it wouldn’t dry out very fast, and would be completely absorbed in the skin so the clean-up is a breeze too. I can’t believe I need to be saying this, but unlike the vagina that would get wet and is in that way self-sufficient when it comes to lubrication, the ass lacks that ability. So use a lot of lube, whatever you are inserting in the ass, and don’t be shy to add more along the way.

6. Fingers are not my friend

Okay this is my thing entirely. For opening up purposes, I actually dislike fingers. But in the case of you don’t have a buttplug on hand, fingers have to do. I’m not sure whether this happens to other people too, but at least for me fingers sometimes feel unpleasant. Because fingers move and they sometimes would stumble upon some places in my asshole that… encourages bowel movement. Aka fingers sometimes make me want to poop. And that feeling, even if I know I just did a very thorough enema and probably nothing would come out, that feeling would still make me glench up involuntarily, thus making my butt tighter instead of relaxing it, and that makes it hurt a lot more. That’s why I prefer being open up with plugs more. Stick it in, breathe through the pain, let it stay in for a couple of minutes. That’s the fastest and most straight-forward way to get ready for the cock.

7. Grand entrance 

I can’t stress enough, lube it up good. Then go in sloooow for your first attempts. You might need to stop to let the one taking it get used to the size. And if you have a thicker than average cock, you might need to do the opening up using several different sized butt plugs. Anal sex is not for those with no patience. I know you might have seen porn videos where the men would tell the women to spread their buttcheeks with their hands to receive the cock, but I strongly recommend against that unless you’ve done it more, so definitely not for the first times. Trust me, that position of spreading the buttcheeks, even if it probably looks super hot, it hurts a lot more.

8. Easy does it

For the first times, that sensual slow sex is the key. Hard and fast anal fucking for the first time would traumatize some for life. It almost did traumatize me for life. So for the first times, maybe you should consider letting the girl/sub determine the pace. Let her/him more against you. I find the doggy style being the most convenient position for this purpose.

9. Grand finale

For those who use condoms, remember to check in between whether there’s enough lube for smooth sailing. And as for those who aren’t using condoms, I hope you are tested. 😀 And just like doing creampies in the vajayjay, climaxing in the asshole also would result in the sperm coming out but not all of it would do it right away. So prepare for getting your panties wet cos of leakage. When it leaks from the vagina, I can feel it coming, but sometimes I don’t even notice it leaking from my asshole before it’s already all over the place. So you might want to consider a small pad in your underwear.

10. No pain, no gain 

Lastly, I regret to inform you, anal will always come with pain. But more you have it, and better you train for it, the pain will get less and the pain period will be shorter. But unfortunately, it is always going to hurt. But that mind-blowing pleasure and those whole body orgasms, those make anal worth the pain. You know that extremely good feeling that makes your entire body shudder and go all goosebumpy, that feeling that occasionally comes when having vaginal sex? For me that feeling comes with every thrust during a successful anal sex experience. And as a masochist myself, I’m already used to the pain, sometimes even embrace it, but I am not immune to being punished with anal either. But as I said before, that’s a story for another day. Until then, stay kinky! 😉


7 thoughts on “Anal Survival Guide

  1. My wife just texted me earlier and asked if I wanted her ass. Without being over excited, are you up to it? Then just said we will see.


  2. Thank you for sharing these tips Emmi. The last “milestone” in my D/s journey with my Mistress was releasing my hard limit on anal. I wish I had read these tips back then 🙂

    Liked by 2 people

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