Sexy Fun Advice Advice,Featured,Kinks Beginner’s Guide to Anal Sex

Beginner’s Guide to Anal Sex

So you have decided to try allowing a penis to enter through the backdoor. First off, congratulations…but first, there are some things you need to do to make it a good experience.

You do need to keep in mind that anytime you go knocking on poop’s door, there is a chance he might shake your hand so to speak. While nothing you can do can totally prevent it every single time, there are steps you can do to minimize contact with any chocolate residue. We have a guide to Cleaning Up For Butt Play that you should start off with to make sure you are as clean as possible.

A few extra things you should have handy include:

  • Baby wipes
  • Towel
  • Disposable Gloves (optional)
  • Condoms (optional)
  • Lube (and lots of it)

Unlike the vagina, the anal cavity does not produce and lubrication on its own. For anal sex to have any measure of success, there will need to be a good supply of quality lube available. There are lubes that are formulated specifically for anal sex that are thicker and will last longer.

Under no circumstances do we recommend using any form of numbing cream. Anal sex should NOT be painful in any way and any hint of pain means that something is wrong and you need to stop immediately and figure it out. A numbing cream can prevent you from feeling any pain and not realize that you could actually be doing some physical damage.

I did mention condoms above and they are totally optional unless there is an STD concern. Some people still prefer to use a condom “just in case” there is some fecal residue, making for quick cleanup. If you are using a condom, then I suggest a water-based lube to ensure it doesn’t degrade the condom.

Starting off Slow

Very, very rarely does anal sex just happen for the first time and it works out to be a pleasurable experience for everyone. The key is to work up to it. A penis is not a small object to be forcing through your starfish so starting slow and working your way up will pretty much always end up as a success.

Getting ready for anal is a process, a journey if you will. It can take a few sessions up to numerous depending on the person. I suggest you start off very slow. Lube up a finger and just massage the butthole, get her used to that sensation. Constant checking in and communication is the goal here. If she is really enjoying that, ASK if you can try putting a finger in. Again, making sure there is plenty of lube in play. If she is good, work it in nice and slow, no quick moves here. At any sign of pain, stop, communicate. Is it time to stop for the day? Did you move too quick? Figure out what is going on before proceeding.

Maybe this is enough for the first session, next time do the exact same thing, and after she is comfortable with one finger, ASK if she is ready to try two. Maybe the next time you try a small toy, she can also try butt plugs before a session.

Tips for Success

  • Make sure she is properly aroused first, don’t lay her down and go right for the brown taco
  • Mindset is everything! Being relaxed and comfortable is one of the most important things
  • Any time you insert anything, stop, let her get used to the feeling before probing around or doing any other movements.
  • Focus on small goals each time e.g. one finger, two fingers, small dildo, etc


While anal sex may seem to be a dominant/submissive act, you have to let the receiving person be in control The receiver sets the pace. If the giver is in control, things can go downhill very quickly. The receiver needs to call the shots here, nobody wants a runaway penis jackhammering their fart box out of control.


The best positions for your are going to what you find comfortable and enjoyable, it doesn’t always have to be doggy or spooning. You can do missionary, cowgirl, and others. You just need to figure out what works for you.


As I said, anal sex is journey, not a goal. It will take some time to get used to things being in the exit hole, it will take time to learn to relax with different size objects. Make sure the giver is on board with “no means no” and “stop means stop right this instant!”. All along this journey you will find different types of pleasure and even orgasms. Enjoy the ride!

Come join the discussion on Reddit at r/SexyFunAdvice

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