Anal Sex for Beginners

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Q: My girlfriend has been curious about trying anal sex for the first time. I was wondering if you have any pro tips on how to make her first anal experience as comfortable and pleasurable as possible. My first experiences bottoming were less than pleasant, and I’m sure you understand my desire to make it as pleasurable and pain free as possible.

A: Patience and lots of lube are the keys to a good first anal sex experience. If she hasn’t had anything in her butt before, plan on taking at least a few weeks before you move up to anything cock-like in her bottom.

First, she will have to be fully aroused in other manners. Makeout, play with her nipples, rub her clit, you know whatever gets her motor running. It is always easier to try new things when you’re both pretty aroused before you start. Then use a good thick lube (I recommend Maximus) to rub around her anus. It is a good idea to rub the lube in your fingers a bit to warm it up first especially in the winter months. The first time you do this, don’t have the goal of actually going inside of her anus unless she insists. The goal is more for her to get used to feeling arousal from that area of her body. So many of us aren’t used to feeling good sensations coming from our butts if we haven’t experienced anal play before. Try pressing and rubbing all around the sides of her anus. If she begs for more, then let her have the first one or two knuckles of one finger. But no more than that. You’ll have plenty of time to explore in the next few weeks. And only play with her ass for as long as she can take it. The anus can wear itself out from extended play.

The next couple times just use one finger and still lots of lube and arousal. The more of a tease you are, not giving in to her full desires to be penetrated in her ass, the more she will crave it. And it is always better to go too slow than too fast when it comes to the butt.

Now, you may think you’re ready as you move from one finger to two fingers. But no, you are not ready to stick your dick in her yet. Like I told you before, the anus gets tired. Wiggling your fingers around can feel pretty nice, but if you want to move onto a cock you’re going to need to purchase some butt plugs. Tristan Taormino taught me that the more you mess with the butt, the more likely it is to say “no more tonight honey.” So the best way to warm up to anal sex isn’t going to be by going in and out of her butt with your fingers, but slowly stretching it out to prepare for your dick.

Bootie is a great beginner plug. Then you could maybe move up to something like Ryder. Or for convenience you could just get every size of the Pop Plugs which are relatively inexpensive silicone plugs that work their way up in size. But whatever you do, don’t forget the lube in all of this. It is SO important!

When you’re first starting out with plugs feel free to switch between them and fingers, but make sure that the fingers you use for her vulva/vagina are not the same fingers you are using for her butt.

Once your girlfriend has become comfortable with the biggest butt plug in your repertoire you can then move on to your dick. Just remember that you have to do finger, then small butt plug, then bigger butt plug, then maybe an even bigger butt plug, and then your dick each time you do this. It will become easier with time and she can also warm her ass up for you in preparation for a hot night of ass sex.

Things to keep in mind:

  • Do NOT use any sort of anal desensitizer!!! I cannot say this enough. The tissues in your rectum are very delicate and can easily be torn. Desensitizing your ass means that you won’t be able to feel something going seriously wrong.
  • And on that note, if something hurts, stop. Slowly take whatever is in the butt out and do not try again until she is comfortable with it in a day or more.
  • Use lots of lube! There’s never enough lube!
  • Shit Happens
  • Wear a condom!! I don’t care how monogamous or disease free you are. Bacteria in your urethra is a big no no and there’s a lot of that in everyone’s butt.
  • Communicate with each other about how things are going.
  • Remember, butt sex is supposed to feel good for both people. So if she’s not enjoying it, then its probably not worth pursuing.

4 comments to Anal Sex for Beginners

  • Hah. I *just* had someone email me with a similar question yesterday! I gave her some info and resources, but just sent her this link, too.

    I also recommended Bootie, Ryder, and Maximus. Good to know we’re on the same page!

  • Great minds think alike!

  • I am curios about anal sex. Me and my husband discuss it but we are waiting on the right time. I was wondering what is the best position for beginners?

  • Christopher

    First of all you cant enter her ass with your penis first time. You must try with something smaller firts, like finger, or sex toy, or if you don’t like that idea penis is ok, but very very slowly. Stuff you need: baby ass wet wipes (if shit happen, and its good to have them near), lube (water based, makes less mess), baby oil (helps in relaxation and its fun) and patience.

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