Anal Stretching for Beginners: Tips and Tricks Revealed Anal Stretching for Beginners: Tips and Tricks Revealed

Anal Stretching for Beginners: Tips and Tricks Revealed Anal Stretching for Beginners: Tips and Tricks Revealed

Have you ever tried to fit a square peg in a round hole? That’s kinda like what anal sex feels like without some careful planning and anal stretching. Unlike a vagina (or your mouth), the anus only stretches so far. The good news is, with enough practice, relaxation, and lube, you can stretch your anal canal so receiving that big cock or dildo you love so much is not only comfortable but extremely satisfying.

Anal sex, like any sex act, should feel good!

Yes, there’s no denying that, at first, anal sex can be uncomfortable and sometimes painful. But if it’s something you’re interested in trying, you need to approach it with an open mind. You also need to ditch any preconceived notions of what you think anal sex should be and accept it for what it is! The anal canal is packed with lots of feel-good nerve endings. A relaxed approach to anal sex that starts with anal play and anal stretching can lead to some heart-pounding orgasms! 

What Exactly is Anal Stretching?

Everything you need to know is pretty much right there in the name. Anal stretching involves inserting progressively larger objects into the anus to help stretch and widen the opening. The end goal is having more anal comfortable sex and a more receptive butthole. 

There are anal stretching kits designed specifically for this purpose, but you can also progress using fingers, butt plugs, beads, and other anal dildos and toys. Pick your pleasure!

The Dos and Don’ts of Anal Stretching for Beginners

So, you’re ready to start warming up your anus for full penetration. Congratulations! But before you get started, here are a few things to keep in mind to make your anal stretching adventures more fun, less scary, and a lot more successful.


  • Use the bathroom and/or use a douche if you’re worried about making a mess.
  • Start with smaller toys or fingers first.
  • Stop the minute you feel pain, resistance, or see blood (But don’t freak out! This is completely normal and as long as you stop immediately, you’re not in danger of doing damage.)
  • Use plenty of lube and get the right kind. Silicone lube is often the best because it’s thicker and doesn’t get sticky the same way water-based lube can. Remember, your anus isn’t self-lubricating so it’s your job to provide all the lube you need for safe and comfortable fun.
  • Practice makes perfect. Similar to the training you do in the gym, anal stretching is sort of like a training regime. You should practice stretching 2-3 days a week with adequate rest and breaks in between. You want to be consistent without overdoing it. Listen to your body.


  • Don’t use anal ease or other numbing lubricants. Remember, pain is actually a good indicator when you’re pushing your body too far, too fast. If you have to numb your ass, chances are you need to back off and take a break. Not to mention, you’ll be numbing both the pain and the pleasure, which kind of defeats the purpose! 
  • Don’t do too much, too fast. Anal stretching is all about patience and progression. It will take several attempts before you work your way up to having unobstructed, pleasurable anal sex (but it’ll be well worth the wait)!
  • Don’t force it. This goes for both physically and mentally. If you hit a roadblock, don’t push the toy, penis, or fingers any further. Remove it, wait a bit, and then try to ease it in again. The trick here is to respect the resistance you feel, like jam your way past it. Also, don’t force the entire idea of anal stretching or penetration if you or your partner aren’t fully on board. 

Here’s How It’s Done: A Step-by-Step Guide 

Ok, it’s time to get into the specifics of anal stretching and how exactly it’s done. You’ve prepared yourself both physically and mentally (showers, pep-talks, lubes, and deep breathing) and now it’s time to get down to the nitty-gritty!

Step One: Warm-Up

Similar to exercise, you need to warm up before starting your anal stretching routine. First, find a position that’s most comfortable for you. For some people that’s on their back, others prefer to lay on their side or even on all fours, reaching back between their legs. Try out a few positions and see which one feels best.

Once you’ve settled in, get your lube and finger (or fingers) ready. Place a good amount of lube on your fingertips and the outside rim of your anus. Circle your hole with your fingertips until it feels good. Once you’re ready, slowly insert the tip. At the same time, take deep breaths and try relaxing your anal muscles. Continue using a circular motion and avoid shoving your fingers in and out (you’ll progress to this eventually).

If you’re able to get two fingers inserted, try to slowly spread them apart, stretching your anus every so slightly. If this is overly painful, stop and try again another time. If it feels okay, or even good, you’re probably ready for step two.

Step Two: Bring on the Toys

The next best thing to your fingers is anal toys designed for anal play and anal stretching. Some favorites are butt plugs, anal beads, and small dildos. 

Start with a small butt plug that’s tapered at the end (so it doesn’t get lost inside your body). Add more lube to the tip and slowly insert it. If it goes in smoothly, continue breathing and relax your anal muscles as much as possible. You’re trying to move past the point of resistance so that your sphincter muscle will naturally pull the toy into place inside your anal canal. You’ll know it when it happens and it may take a few tries. 

Step Three: Try an Anal Stretching Kit

Anal stretching kits are basically one-stop shopping for anal stretching for beginners. No two kits are the same but they usually offer 3-4 butt plugs of various sizes, each one gradually bigger. Start with the smallest toy and work your way up until you can comfortably insert the largest option.

Once you have the technique down, the process of anal stretching is fairly simple. You’ll repeat the same process of relaxing, applying lube, and inserting and removing anal toys until you reach the point of resistance or discomfort that borders on pain. Take breaks in between and over time, your anus will get wider, and inserting larger toys or a penis will not only be easy but arousing and pleasing!

Anal Stretching and Kink Play

If you want to take anal stretching to an entirely new level, you may have a fetish for butt play. This involves stretching the anus far beyond the point needed for comfortable sex. Once you blow through this anal stretching guide and master penetration, you may want to dabble in the kinky world of anal fisting and even gaping. 

Intrigued? Check out this article and take your anal game to the next level! 

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