Anal Training: beginner to expert guide

I really enjoy anal play of any kind and have done for quite a while. Anal sex is something PurpleSole and I jumped into doing fairly early on in our relationship, over 10 years ago. What I didn’t do is read the best ways to engage in the activity to get the most pleasure and the least potential for damage. Anal training is not something we would have known about back then, it just wasn’t in my vocabulary.

I have written before on our blog PurplesGem about how anal sex changed for me when we started our D/s lifestyle in A Little Bit Anal. How although I really enjoyed anal, it usually ended in me tearing…ouch. So if you are looking to start out on your anal journey, looking to step it up a notch or just looking for a refresher. This is the anal training guide I wish I could have read all those years ago. 

Relax and be comfortable

Easier said than done right?! I think the turning point for me in anal sex becoming more enjoyable was just being at ease with it. When your mind is happy and relaxed about something, your body will follow, which is incredibly important for pleasurably letting objects inside of it. 

The steps to becoming relaxed about anal play are going to be different for everyone. It may be that exploration yourself in that region might be a good idea, take time to see how your anal muscles clench and relax at touch. Play around with different techniques to see what you like, circling, stroking or even dipping a finger inside your butt.  

If you wish to engage in anal play with a partner I think communication is very important and will help put your mind at ease. For me, it took a lot of trust to comfortably allow PS access to my arse. To know that he wasn’t going to just plough away if I wasn’t ready. Talk about what you like and don’t like. Explore together.

Anal Training: Beginners knowledge

This really for me ties in with being relaxed and comfortable about anal. Getting the facts on the long term affects of anal really helped put my mind at ease. Knowing that the things you hear about your arse becoming loose after too much anal is utter poo, made it that much easier to let go and enjoy anal play.

How much lube is too much lube?

I don’t know the answer to that one. But I can certainly say I have never entered into an anal situation and been upset by there being too much lube. And I don’t really like mess very much.

As your butt doesn’t make its own lubrication It will certainly appreciate a hand. Having lube applied around the area is fun in itself, feeling the cool liquid glide and dip inside certainly puts me in the right mood. I would also recommend slathering it on any object that is going to be inserted, be it a finger, cock or large object. Get that bad boy covered in the stuff to make for enjoyable insertion and fun thrusting. 

There are lubes specifically made for anal and a few of them do contain a mild muscle relaxant in them for easier insertion. I personally prefer to use a creamy silky water based lube but it’s entirely down to preference. 

Take it slow

I really think that this one needs to be in big bold letters, as it’s the one I tend to forget in the moment when overcome with passion. Whether it’s your first time or your an anal connoisseur, those muscles are tight and need time to relax, adjust and accommodate what is being inserted. Do not try to ram stuff in there at high speed no matter how horny you are. Believe me it will not end up in a fun filled orgasm, just pain and possibly bleeding. Not fun at all. 

For beginners I would suggest using fingers until you are completely comfortable with the sensation. Pleasuring other parts of your body at the same time may help you to relax and get into it more. This can take time, every body is unique. If you are not comfortable with using anything bigger then don’t. No pressure, it is not a competition. 

Once you are happy and feel you would like something larger, that could be after a day, week or a year. I would suggest using smaller toys as a step before using a cock (or cock sized toy).  

Anal training plugs

I think the training plugs are a great next step. Although I have never owned an actual set, I have bought over the years a lot of plugs and toys that get progressively bigger in diameter so are similar to a set. If trying to work up to anal sex, getting used to each plug is a great way of feeling comfortable with accommodating lager sizes.  

Again take it slow. Slow insertion and slow progression to the next size. Some days you might not be able to take a size you could previously. This is completely normal, your body and mind are responsive to so many different things that you might just not be able to at that time. Stop and try again another time, don’t force it.

There are also different materials of toys to try out that provide different sensations. Personally, I really enjoy the hard and smooth textures like glass or metal toys in my arse, but others may not. Some people enjoy bumps or ridges on their toys or even ones that vibrate. Have fun and play around, you never know what you might find that hits the right spot.

Anal Training: Expert level 

I wouldn’t regard myself as an expert in anything, I may have just thought it was a funny title.

When I am wanting to use a toy that is larger than a cock there are certainly steps I would now go through before insertion. 

Personally for larger toys I like to make sure I am a bit cleaner by using an enema bulb. This is totally an individual choice as I know some people absolutely hate the feeling of it. But for me, the larger the toy is, the more clean I want to be. This directly relates to experience of the larger the thing that goes in, the more you are filled and have potential for poop to cling to the object. Logically I know that ‘if you are knocking at the back door, you might find that someone is home’ and that IS FINE. We are adults, just deal with it. But in myself I know I am more comfortable once cleaning out a bit first. The only drawback I find from cleaning out is that you do have to wait a bit to make sure all the water is out, so you need to sort of plan it in 30 minutes beforehand. Not great for impromptu situations. On a side note I have written before about Enema play if you would like to have a look.

The next thing I would do is a quick run through the list above. Getting into the right mood, usually with the help from PS touching and caressing me. I would pick out two or three of my medium to larger toys or plugs that would lead up to the size of the toy I ultimately want to enjoy and play with them for a little bit. 

Starting of course with the smaller of the three, cover it and myself in lube and then start to circle the toy around my arse, when I feel my excitement and anticipation rising I would then gently press it to my hole. Something PS likes is if I do this by putting on a ‘show’ for him. Lying on the sex blanket in front of him so he has full view of what I am doing. He may also choose to touch his cock at this point to really heat up the moment, giving a great visual for me too.  

Personally I like to fuck myself with the toy for a bit before fully inserting it in. For me the sensation of the toy going in and out is what I like best. This can still be done slowly though, it’s certainly not a race. If at any point you start to feel uncomfortable then stop.

Once the toy is nestled in I let it sit there for a bit, allowing my body to get used to it before I slowly start to remove. Then I move onto the next toy, progressively bigger in size and repeat the same steps. This allows my muscles to relax and for my arse to be used to being opened up. Then when I finally get to the big toy that I had in my sights all along, it’s not so much of a shock for my body. My anal sphincter has been suitably prepped and trained in that moment for the big object (or fist) that I want to play with, thrust and climax whilst deep inside my butt. 

After thoughts

This does not mean your anal training is complete. These steps should be repeated every time you engage in anal activity. Perhaps not to the same degree. I can now go from ‘nothing’ to full on anal penetration with PS’s cock,

 so I would skip out the toy sizing stage. But I would still use the other steps. Everyone is different and really it is better to take it slow if you are not sure of your body’s limitations and most importantly respect your body’s limitations when you do know them.