My girlfriend and I have tried to have anal sex but her butt is too tight to get my penis in, what can we do?

This reminds me of an episode of House I just watched, season 2 episode 18. Chase is giving a younger Emma Pillsbury a rectal exam when he says:

 

 

 

 

 

 

 

 

 

 

 

 

 

Younger, less perky looking Pillsbury is disinclined to acquiesce to his request and experiences some painful tube insertion.

 

 

 

 

 

 

 

 

 

 

Now, it doesn’t look like she’s loosened up a lot in the past two years, so I’m going to guess that she has not been abiding by important rule #1 of anal play. Warm up first.

 

 

 

 

 

 

 

 

 

 

 

In the anal canal are the sphincter muscles (the internal and the external) and you will  need to please both of these sphincters to obtain entrance. Once you warm up the external muscles, the internal ones will follow along. They work together. Once you have warmed up the ass enough to allow comfortable penetration you may not have to repeat the warming up process again, as long as you continue with the anal play.

A good way to warm up the ass is by using a lubed up finger and just teasing it. Don’t push in yet until you start to feelings open up. Then go slowly and steadily inwards will communicating with your partner. If this is a step that is easy for both of you to accomplish, you may want to try upgrading to a butt plug or anal beads.

It is likely that she does feel tight, but I assure you that it is not impossible to get your dick in her ass. You’ll need to work together by communicating constantly about what you’re experiencing and how fast or slow to go. The warming up process is critical, because you don’t want to tear anything. Lube is also critical because it will help you slide in, and the anus doesn’t produce it’s own lubrication.

A helpful tip for getting started is making sure your partner is aroused before getting into anal play, if it’s not something she is already comfortable with. Start with regular penetration or fingering or oral sex. Have her keep playing with her clit while you work the backdoor. Keeping aroused while you experiment can be helpful in resisting the urge to tense up to the new sensations.

Good luck.