Everyone's "needs" will be different, but the usuals include gloves, lube, the toys, disposable pads, towels, paper towels, and condoms. If you need some Liberator sex furniture to comfortably reach your butt, don't forget to grab that too.
Use so much lube
The biggest "secret" (and please, let's stop making this a 'secret'!) to pleasurable anal play is lubrication.
Lots and lots and lots of lubrication.
The butt doesn't provide any amount of slickness. When you're inserting a toy, you need to provide all of the slickness for it. This means lots and lots of sexual-specific lube. Before you insert the toy, slather the toy in lube. If you are using a silicone toy, stay away from silicone lube, as they degrade each other...a water-based lube is best. If it is a stainless steel or glass toy, sticking with silicone lube is great; the long lasting slipperiness of silicone is going to be your friend!
Rub lube in and gently around the entrance to your butt, too. If you think you've used enough lube, it probably isn't enough. Throw more on there. If you'd describe your toy as "caked in lube," you're probably at the right level.
Take it slow
No matter what type of anal toy you're using, you still need to take it slow. Gently press the toy up against your entrance and allow yourself to feel the gentle stretch as the toy slowly stretches your body open. Don't "shove". Instead, gently apply pressure until you've reached a spot where it feels pretty intense. It will feel very full - and like there's a lot of pressure.
Let your body rest there before proceeding. In fact, if it never stops being "intense," you've just reached your limit for the day. Don't try to go past that. You may not insert the entire toy your first time, and that's a-okay. It's a fun challenge that you get to conquer over time!
There should be no sharp pain at any part in this process. If there is, back off from going as deep as you are or add more lubricant. If the pain continues, call it a day and give it a try some other time.
You can continue playing with your toy in a way that is pleasurable for you. Consider wiggling or jiggling it. Do small, tiny thrusts. Pull out entirely and insert back to the same depth that you were before. While butt plugs weren't necessarily designed for thrusting, the Odile's design or flared base dildos can be great for full thrusting.
Experiment with various movements and see what feels best for you with this particular toy. The sensations and enjoyment vary with every individual toy, but you can get to know this toy and learn more about your body and your pleasure potential in the process.
Clean up and put away
Once you've achieved your desired "end" (whether that's orgasm, moving onto something else, or just being done for the day), it's time to clean up. I know it can be easy to put this off or forget about it, but this really has to be done within a half-hour of finishing up your playtime.
Cleaning the toy as soon as you're done with it will help prevent the toy from retaining any scent. Not only that, but warm water and anti-bacterial soap will remove any gunk and bacteria from the surface of the toy - getting ready for your next play! If, after your wash, you find the toy is still retaining any scent, let it sit in a bath of soapy water for as long as humanly possible.
You can even get a bowl just for filling with water for this purpose. I've let mine soak for three days before. Clean it thoroughly again after you've let it soak. The scent will gradually fade the longer the toy stays in the water. I don't know the scientific reason for this - it's just always what has worked for us.
Are There Ways to Make This Go Quicker?
Hold on, cowboys, cowgirls, and cowpeople! Part of the fun (and safety!) of anal training is going at your body's own speed. This isn't something that's supposed to happen overnight. Trying to "force" it to happen overnight can cause tears and potential health issues.
That being said, there are some ways to make it move along a bit faster. The easiest one is the rule of simple frequency. If you use your anal training kit toys more often, your body will acclimate to the stretching and size of the toys faster.
I'm not saying you should try playing four times a day, but if you increase your play sessions from once a week to three times a week, you'll move more quickly through the various sizes in your anal training kit.
The other way to help it move along faster is to use toys that "stay" in place for longer sessions. While you might get tired of holding a dildo in place for a couple of hours while you play a video game, keeping a toy inserted becomes a whole lot easier when it's a butt plug and it stays in by itself. This gives your body even longer to acclimate to the "stretch", and since it's time where you're focused on something else, it's probably just bonus pleasure time to you!
Read: A Beginner's Guide to Anal Stretching
How Do I Know When It's Time to Move to the Next Toy?
If this is your first anal training kit, you're probably still new to the feeling of anal sensations. So how do you know when it's time to pick the next-largest toy in your kit?
Well, there are a couple of signs. First, you should find your body simply and easily taking the entirety of your current toy. While you may still need to pause to take little breaks during the insertion, you'll notice the entire process has become a lot smoother - and it may only take a minute or less to get the entire toy in.
Another sign of being ready for a larger toy is the lack of the "intense stretch" that you used to feel. When your body doesn't feel stretched out as far as it used to when you started, that means that it's getting used to the stretch of the size of the current plug. That's not a bad thing! It just means that it's time to consider changing to the toy of the next-largest size.
Finally, the last "sign" of changing to a new toy is the feeling of boredom. If you're not particularly excited by the toy, even if you haven't "mastered" it, there's no reason to keep playing with it. Maybe your body just doesn't like the shape of it. Maybe it just aesthetically isn't a turn-on for you.
Whatever the reason, as long as you're not injuring your body by playing with a different toy in your anal training kit, there's no reason to stay on a smaller toy when you aren't enjoying it.
When Should I Buy New Anal Toys?
When should you think about "upgrading" past your anal training kit? The honest answer is: "whenever you want."
Has your anal play piqued your interest in another body safe sex toy? Have your experimentations led you to think that another toy might hit your pleasure points better? Do you just want to upgrade to a different type of materials or color scheme?
Whatever the reason, you can really stop using your anal training kit whenever you want. Who cares if you're half-way through the middle size and can't take the large one yet? As long as you find a toy that's smaller than the large size, you'll be fine.
We have a lot of guides here on Kinkly to help you select a great anal toy for your toy box once you've settled on adding something to your collection:
Just remember that you own the anal training kit in case you ever want to stretch yourself for larger toys in the future. That way you don't accidentally buy another one!