These are excellent questions!
Lots of lube is a good tip but even before that, the starting point is being relaxed and aroused. So if you’re exploring early on, starting it in a bath after a good long edge is perfect. The other benefit of exploring in the bath is you aren’t worried about cleanliness so much.
In terms of what you should start with, not a dildo, not even a butt plug, but just your finger! Make sure you have short nails and just try gently playing around your bottom as you play with your clit with your other hand. I often get girls to copy, front and back, as a fun little game. Masturbating your asshole, hot.
The majority of pleasure nerve endings back there are around the entrance, and just inside so enjoy that. Then as you feel ready, just push the tip of your finger in and out a little, get used to it. It won’t tend to feel amazing, just okay, it’s the thrill of being so naughty that’s a bit part of it. As you relax with that you can start to enjoy how it feels more.
Don’t go too deep, just the first part of your finger, get used to how it feels, get relaxed about it. Then you’re ready to use a toy. A small dildo or butt plug, or even a very smooth handle of a hairbrush will do nicely (that’s what I started with, when I was a young teen).
The golden rule with any anal play is whatever you stick up there has to have a wide base that cannot let it be sucked up inside. Your bottom will eat things, don’t even try it, it’s a hungry little fucker. The ONLY thing safe to put up there without a flange is a smooth, melting icecube, because it melts (that’s how they cool dogs down who have overheated!). But ice play is Anal Play 102.
So, it’s definitely worth getting a butt plug because they’re designed to fit nicely there. See my toys recommendation page for the ones we use.
Plugs, once you get used to them, are great for keeping you secretly very aware of being a naughty little slut. Just build up the amount of time slowly.
And don’t think you’re being clever getting a thin one to start, they are TOO thin and you just feel like they are slipping out all the time, which is awful. A bit wider, with a think ‘neck’ is what you need.
In terms of keeping clean, which is obviously a big issue for many of us thinking about anal play, you need to be aware that poo isn’t actually right at the entrance of your butt. It stays higher up in your colon until you actually push. So the first part of your bottom, the rectum, where toys and fingers and penises go, is mostly empty most of the time. So the major tip is go to the loo a few hours before you plan to play and you can be sure there’s nothing much up there.
Then you need to go from ‘almost’ empty to properly washed out, and the best way to do that is in the shower, stick a soapy finger up your bottom and give it a good rinse with the water. Give the outside a good soap and scrub too, and that will do you for most cases.
For extra security you can ‘douche’ it, which is spray a bit of water up there (best done in the shower or you can do it on the toilet) and that rinses out that bit further.
The full washout is called an ‘enema’ where you put up to 1 litre of water up there, but this actually washes the poo down from your colon, so you need to do it a few times to get clean.
If I’m planning on getting it up the arse then I do an in between option of pushing the power shower head against my bottom and letting the water go up and bit, and then sitting on the loo, rinse and repeat, finish off with a soapy wash.
But be careful with that as you only want a small amount of water up there. Also, enemas aren’t great for the natural balance of good bacteria in your colon so don’t do it too often.
Having said all that, sometimes the risk is that there’s still a bit of poop involved in anal sex. That’s life. So a condom is always a good plan (beyond the need for it for safe sex) as if that happens, you can just pull it off backwards and bin it.
In terms of fingering and fisting your bottom, you can try it from the front, side or back and see which is least uncomfortable, but unless you’re very flexible they’re all a bit tricky. A toy is best.
Also, be careful about wide things up your butt. Making your ass gape is all very porny but it’s not like your vagina, which is designed to stretch, you can do serious damage if you stretch it too much.
Can I also add, if you’re thinking of letting him fuck your arse, make sure you get him to lick it too because analingus feels AMAZING. Remember how I said most of the nerves are there on the outside, yep, that’s why it feels so good. Just trust me, try it.
Lovehoney have a good guide on some of the toy practicalities
I hope that covers what you wanted to know! Have fun!