Takeaway: Anal stretching is a key component of higher-level anal play - and it isn't as scary as it sounds. If you're new to anal play , you might be thinking, "what?! Why would I want to stretch my butt?! But anal stretching is actually a key component of higher level anal play - and it isn't nearly as scary as it sounds. Technically, anal stretching is anything that gradually stretches the anus and allows you to insert toys or a penis that you couldn't comfortably take in the past.

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What about butt plugs?
If you buy something through a link on this page, we may earn a small commission. How this works. Like other muscles, your anal sphincter is only accustomed to stretching so far. Your anus is full of sensitive nerve endings that make anal play feel oh so good. Anal training can make anal penetration of any kind pleasurable. It can also help you work up to larger anal toys and other butt play, like gaping. This makes it more prone to tearing and infection, including sexually transmitted infections STIs. Taking it slow, using lots of lube , and practicing safer sex can help. Along with elasticity in your tissues that help them flex and contract, mental relaxation is a big part of anal training.
You mean like doing weights with my butt?
It's understandable, I used to have a pretty hard time with this myself when I first started banging guys. For a long time I just thought that it was part of anal and I would just have to learn to like it or something, that it was an acquired taste I just wasn't acquiring fast enough for my liking. But, anal sex isn't like stout beer, black licorice, or stinky cheeses - anal sex is sex and should be enjoyed for what it is, not what you think it should be. The simple fact of the matter is that, in the beginning, anal sex does tend to hurt a bit. However, there are ways to ease yourself through this troubling and, possibly, confusing part of anal sexual exploration. I'm talking, of course, about anal stretching! It's pretty much there in the name! It's a method of working your way up through the insertion of progressively larger sized objects to achieve a more receptive, less painful butthole.
Training and stretching your ass takes practice and patience. Whether you want to have anal sex, use bigger dildos, or you simply enjoy feeling stretched, the same principles apply. But if you want a more exact idea of what size you should begin with, play with your fingers. Lube them up, see how many you can fit in your butt, then measure their circumference. Divide your measurement by pi and choose a plug with a diameter as close to this as possible.