Reader Question: How to get my girl to go anal

Posted by Lilith on April 11, 2011

I recently received a facebook message from a reader asking for anal sex advice. He really wants to have it, but his girlfriend is afraid of the pain. So I put together a few notes for him …

Dear Facebook friend,

Thanks for contacting me. I am happy to help as much as I can!
I have to admit that I somewhat share your girlfriend’s hesitation about anal sex. Going up the butt wasn’t on the table in my relationship for a really long time, and even now, it is reserved for the most special occasions or when I’m drunk enough to agree to it.
That being said, here is some of the advice I received when I was considering the butt.

• Let her ease into it. This could take a night, but it could also take days or weeks (depending on how into it she is).
• Start with a little anal play. Maybe when you go down on her just flick the tip of your tongue around the area. See how comfortable she is with that.
• Then maybe move to a finger (with her permission of course). Use lube of some kind and just start by playing with the area until you and her are comfortable with you slipping in your finger. I usually like this when Ash is fucking me, especially if I’m close, or when he is going down on me. If I’m at that point, he could probably do just about anything to me. I’m relaxed, turned on, and as long as it doesn’t ruin my orgasm, I’m pretty much down for anything.
• After there is some comfort with that, I would suggest moving up to a small plug — bigger than a finger, smaller than your dick.
• At that point, encourage her to practice, practice, practice — both with and without you around.
• Having her explore her ass on her own is a good thing. She’ll learn what she likes, what she doesn’t, and there won’t be any pressure.
• But it’s also fun to have her insert it while you are fucking her. If she can relax, enjoy herself, and ultimately come like this, you are a lucky man!
• After that, I’d say the ass is fair game for you and your junk. One idea I heard, but haven’t tried is if you guys know you’re going to have anal sex that night, she could insert her plug and wear it for a few hours. I’ve hear this is incredible foreplay, and it prepares the area for you.

Alexis Texas has the best ass I've ever seen!

And here are just a few tips:

• Always, always use some kind of lube — and lots of it.
• Try to wait until she is relaxed as possible. If she’s stressed or tense, it’s going to be a bit harder.
• If she lets you enter her starfish, do what she tells you. It’s a big deal for a lot of women, and if you don’t listen, I can pretty much guarantee that that will be the last time you’re ever close to her ass.
• A good friend (male) once told me, “If he wants to put it in your ass, he should be okay with you sticking a dildo in his ass. He will respect you and that area if he’s worried about his own asshole.” So what would you be comfortable with?
• This is a bit of a dirty detail, but it could be part of your experience. Anal sex can be messy. How will you react to that? Because most likely it will be mortifying to her, and if you can’t just laugh it off, tell her it just makes you love her more, etc., it can be a traumatic experience, and one that may not be repeated

Finally, and most importantly, is she even open to having anal sex? This will pretty much be the crux of the entire experience. If she is, then get to work on the above and consider yourself lucky, and tell her how lucky you are. If she isn’t, then it probably doesn’t matter how many ideas you have to try, it’s most likely won’t happen. And I guess at that point, you have to decide how important going up the butt is to you.

Hope this helps. Keep me posted.

xoxo Lilith