Why would you be interested in pursuing anal stretching? The most obvious reason is if you're trying to take a larger item than you're currently comfortable with, but anal stretching is also great for warm-up and for enabling you to take a current toy more easily.
What do anuses and the elephants of adages have in common? They never forget. Truthfully this isn't strictly accurate, but what is true is that it takes a lot of work to make an anus (and the person connected with it) forget a painful experience. Yes, it sounds odd for me to talk about a person and their anus as both having memories in the same sentence, but I do it for a very good reason: the anal area has both consciously and subconsciously controlled muscles, and you need to get them both to cooperate in order to have anything more than the most basic buttfun. Any time you're engaged in buttplay do your best to ensure that there won't be any painful experiences for either to remember.
There are two main approaches to anal stretching, insertive stretching and removal stretching. For both of them you'll need lube, toys, a comfortable place to put yourself, and plenty of time.
Before you get ready give some thought to your preparations. I find to start with a position that enables me to completely relax is best, often lying on my back with my legs propped up against something. The other thing that I find helps are warm toys. A bowl full of warm water with the toys in it is a good way to accomplish this. Before playing at all with your bottom it's best to make sure you aren't worried, because worry = a tense anus. One thing to address is the fear of mess. Make sure you've gone to the bathroom recently and put down a towel or newspaper. If I'm using oil lube or am otherwise concerned about mess I put down some paper towels on top to they protect the fabric. If you would feel more relaxed knowing you're clean then you can clean out before with a small enema or glycerin suppository.
The last thing I'll say before we get started is be careful of the genitals. Yes, most people love to stimulate their genitals, but in most cases genital stimulation leads to anal tightening – so don't, at least while you're actively stretching. You can do a little play once a toy is in place, or as a diversion between thrusts, but stop and give your anus time to relax again before giving your toy another push.
I'll start off with insertive stretching first, because it's the place where everybody starts and also is required for removal stretching. At its most basic it is simple: lube something up and shove it up your ass. Even though it sounds simple, there are still some tricks that make it work better.
First is to start off with an anal massage. Lube up your fingers and rub around your anus. Enjoy the feelings and start to relax. Eventually you can insert a finger or two. Then move on to toys.
There are two ways to approach insertive stretching: the first is step play. In step play you start with a toy you know you can handle, play with it a while, then move to a bigger toy, play with that, etc. It's a good way to warm up, but when you're near your limits the steps between toys feel much bigger. Many dildos or probes provide step play, as do fingers.
The second method uses tapered toys, often buttplugs. Take your time with these, lube up well, and insert to where it just starts to feel like your limit. Rest it there a while, back off a bit and do mini-thrusts, twist the toy, gyrate the toy, whatever you feel like, but concentrate on relaxing. As your anus opens up let a bit more go in and start again. If you reach a limit go ahead and take a break for a minute or two, then try again. “Pushing out” like you're going to the bathroom can help, but make sure you don't push the plug in too much - remember about elephants and anuses...
The other strategy, one I fancy myself on elaborating if not devising, is what I call removal stretching. Removal stretching does the bulk of the “opening” when the toy is coming out. For this a buttplug is the best tool, because they have tapers on both the tip and the neck side of the body.
Removal stretching takes advantage of the physiological operation of your anus. When feces accumulate in the rectum they bump against the inside of the anus, triggering relaxation and a need to use the toilet. By using the relaxation reflex, removal stretching can be easier to accomplish. In a nutshell, what you do for relaxation stretching is insert a plug and then pull slightly on the base so the body taper is pulled up against the anus. Eventually the anus will relax enough for the plug to come out. Don't hurry it too much, otherwise you'll hurt yourself and elephants and anuses(...) - what you want is a gradual opening of the anus until the plug comes out on its own. Once it comes out gently reinsert and let the process repeat until you can easily and gently thrust the plug in and out, then if you want move up to a larger size and repeat.
I'm sure that everyone has seen the potential problem by now. In order for a plug to slide out of the rectum it must first be inside the rectum, and in most cases this means that you have to be able to push the plug through the anus, which requires an anus that can open that much, which means it needs to be stretched already ... and so on. Though it sounds circular you can use this method to open up in two different ways.
First, the repeated relaxation from the inside helps the anus to take a larger plug afterwards, so you can start with something you can insert and move up from there in the step play manner. The second is choosing a plug that can be tweaked in order to have it be smaller going in than going out. While an inflatable plug seems ideal for this, I haven't tried one out yet because I don't like the look of most inflatable plugs – cheap materials and questionable durability have kept me from these. The other option is to try a toy such as the Doc Johnson Sexy Spades or Sasha Grey Signature plug, where it can be inserted at an angle for a slightly smaller maximum body circumference. Personally, I use my Sasha Grey Signature Large to work up to the Tantus A-Bomb and it seems to work quite well with the removal method.
The Doc Johnson Sexy Spades Medium
The Doc Johnson Sasha Grey Signature Large - similar design
Finding a good toy for stretching can be difficult. The ideal toy for insertive stretching is a gentle cone with a base that takes you up an inch in diameter over about 7” of length, but there are few of these, especially in the larger sizes. Removal stretching toys can be easier to find, but again things get hard when you're over about 2” of diameter. There are some insertive probes with nice graduations, for instance the Tantus Cowboy, but of such a length that you might be pushing your limits for both depth and width – never a good idea. Always stick with one at a time. What toys have you found that you like for stretching/training/warmup?
The Tantus Cowboy - one big chunk of silicone, but it does feel good.







