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Anal Stretching Guide For Newbies

newbie guide to anal stretching

A lot of younger guys I meet complain about pain while having anal sex...

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!

What is Anal Stretching?

what is 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.

It's a little more complex than that but that's pretty much what we are talkin' about here. Putting something in your ass until it's no longer uncomfortable and then moving on to putting something larger in your ass and rinsing and repeating until you've achieved mastery of your anus.

FUN FACT: Nearly a quarter of gay men frequently get orgasms from anal sex alone

Now that we know what we are talking about here, let's move on to the meat of the issue. First, we'll look at some do's and don'ts.


anal training and stretching

Do - things to consider before anal stretching

  • Be sure to use the bathroom before you begin
  • If you're a little poopoophobic, you might want to consider an anal douche 3-4 hours before you start.
  • Stop without hesitation the moment you encounter any blood or experience strong pain. The point is to push yourself to the point of slight discomfort, not to tear your ass up. If it hurts you need to stop. If it is just uncomfortable, you're doing it right!
  • Start off with a smaller, smooth butt plug. Make sure it has a taper. Wouldn't want to lose it!
  • Use a lot of lube. Seriously, you can't use enough lube! This is especially true for complete beginners.
  • Use a lot of lube. No, that wasn't a mistake, I didn't double up on this one by accident. You seriously are going to need a lot of lube. Do yourself a favor and follow this advice. Don't get the cheap shit either! You'll be doing yourself a favor.
  • Don't use anal numbing lube for anal training. It's important you be able to feel to know when to move on to a larger sized plug or if you've gone too far too fast. Again, pain is an important indicator.

Don't - things to avoid when anal training

  • Don't force it if it hurts.
  • Don't get ahead of yourself. Be sure to exercise a little patience. There's no need to go thrusting about now, that's what you're working up to.
  • Train every day. It's a good idea to let your body adjust and rest after a good stretch session. I found a good 2-3 days to be sufficient, but you know your own body better than anyone and will find what works for you. Just be sure to give it a rest from time to time to avoid any injury.
  • Start with a plug larger than 4.5 inches in circumference. Remember, the idea is to start small and work up.

anal training kit

The basic supplies needed for anal training is a set of graduated butt plugs of increasing diameters and a high quality anal lubricant. Additional tools can be helpful such as a lube shooter to help deliver the right amount of lube into your ass, as well as an anal douche to help clear out any unwanted backdoor surprises. 

Technique - getting anal training done right

Now that we have the basic do's and don'ts out of the way, let's move on to technique...

Step 1 - getting warmed up and ready

First, you are going to want to find a position that's right for you. Then, relax and begin with your fingers. Don't just go jammin' them in there willy-nilly. This part of the exercise is to get you warmed up. You don't sprint a quarter mile to get warmed up for a marathon, the same idea applies here.

Just lube up your fingers and work them around your hole a little bit while trying to relax your anus. Using circular motions feel it out and massage it a bit. When you think you're ready, start to slowly insert them into your anus. Keep up that slight circular movement.

Once you are comfortable with the presence of one or more of your fingers in there, try to give a little stretch with your fingers and see how it feels. If you are comfortable with this, move on to step two.


Step 2 - training with anal plugs

Now, lube up your smallest sized plug and refresh the lube in your hole. Start to slowly insert the plug until it becomes uncomfortable. Remember, you want it to be uncomfortable, not hurt!

Once you reach the point of discomfort, leave it there for a few seconds and retract it. Then, slide'er back in there. Try to go a little further this time. If you can only reach the same point as before, no worries. Just keep repeating this process until you've managed to take the whole of your smallest sized plug.


Step 3 - becoming a master through practice

It get's pretty simple from here on out. You basically repeat the same process only with the next largest plug. Follow all of the same steps as the previous size. Remember, there's no need to rush. Did I mention you should use lots of lube?!

You'll want to keep this up until you reach master the largest plug you have. That's pretty much it! Just be sure you give yourself time to recover after each session and be sure to not attempt moving up to the next size plug to quickly, and you should be alright! You probably won't want to attempt more than one size plug per session when you first start out, but that's for you to decide. 



    I wrote this guide with the idea that you would be using a graduated series of plugs in mind. This is how I did it, and from talking with some people I know, that's pretty much the common way to go about it.

    Colt Anal Trainer KitColt Anal Trainer Kit

    I don't recommend using increasingly larger dildos, because the tapered shape and graduated thickness of butt plugs make them ideal for this purpose. Your mileage may vary.

    In any case, if you don't have a graduated series of butt plugs, they are pretty easy to find in any sex shop, on or offline, at prices that aren't going to rip you a new one. They usually come in sets of three, but I have seen some variation on that.

    In any case, you should now have all of the knowledge you need to go forth and conquer your butthole and, with a little practice, you'll be well on your way to enjoying painless anal in no time!

    FUN FACT: 45 percent say that they always — kiss after a blowjob.

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    anal started kit

    Anal Starter Kit

    This kit is great for those who are beginners in anal play. We took the guesswork out of your hands. We built this anal starter kit with everything you will need to get started with anal pleasure. We have included our popular Colt Anal Trainer Kit, which is great for beginners since it comes in 3 different sizes. We also added the Colt Anal Douche, which will allow you to clean up before you start playing with the butt plugs. The Pjur Water-Based Lube is the finest, smoothest lube out there, and the lube shooter will help you get the in every nook and cranny! Available for $69.99. Learn more.

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    • Hi!
      I came here looking for advice on how to train my anal hole for sex (I’m a woman and complete beginner). Thanks for all your useful tips! I was wondering a couple of things:

      1) You mention “Additional tools can be helpful such as a lube shooter to help deliver the right amount of lube into your ass” – Where can I get that? I’d love to buy one, I think that’s a great idea.

      2) I’m allergic to fragrances and prone to infections, so I need a fragrance-free lube that has no glycerine. Which one would you recommend?

      A few months ago I was trying some training already (I bought a set of butt plugs, different sizes, silicone, then tried out the medium-sized Tantus silky dildo, which slides wonderfully in, pain-free, much easier than the butt plugs). I did that everyday for several weeks. I didn’t start with my fingers at all, and maybe got a bit carried away, so I’ll try following your advice now. I think I have to be more careful with my skin tissue (to avoid tears, etc.). My impression was that even if I trained everyday, I always had to start with the smallest plug, then medium, then large, every time during the same session, it didn’t work to start with the largest one right away. Is that normal?


    • @katie, maybe try a small set of beads.

    • I’m Very tiny, including my anus. Ex: doc exam- 1 finger in my poop shoot painful. Purchased small ‘beginner’ dildo. Took me 45 min to get just 1/2 way- yes plenty lube; no farther w/ out pain. Can’t find smaller dildo to start with. Any ideas/ suggestions? Please~


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