I want to share some anal sex advice with you (minus personally identifying information, of course). Maybe you’re going through the same thing and it can help or at least just start the ball rolling toward an interesting discussion on the topic of anal sex. Do leave a comment if you have something to add to my advice, or if you want to ask a follow up question.

A wrote:

I have a question on how to approach the act of anal. My fiance is open to anal but deathly afraid to make it happen. She’s very sensitive and kinky and freaky and like it once we devirginize her of it.

I’ve done anal in the past several times with others but not with her yet. The others have either had experience or well, I didn’t really know what I was doing beyond lube and going slow.

So how should we go into things? I was thinking maybe using my fingers while we’re having sex or maybe using a bullet for vibration while during sex.

How should I approach the situation so that she’ll be ok to do it again and enjoy it? She gets off very easily. Anything I do to her she’ll cum with and she usually gets off 10 times during sex.

Any advice would be great.

You already know what to do. Get her off first, then while she’s getting off, introduce your finger into her anus. This will teach her body to equate her orgasm with anal sex. Take it slow, build up in size a little at a time. She may feel uncomfortable with accommodating your cock at first. I know I was. Part of the discomfort was the fear that I might make an embarrassing mess. It took me some time to learn how to relax while taking it in, but once I learned to let it go, I started having orgasms while having anal sex. Have fun!

Here’s another question about anal sex, from someone with more experience. M wrote:

I told you that you inspired me to get my wife into anal sex, which she is, and which is great (STILL have a hard time believing I got this little firebrand for my own). We’re learning the ins and outs (sorry, HAD to be said), and there’s a question I hope you can help me with.

We normally couple up anally in either a doggy position, or with her on her back and legs stretched out. The last time, however, she wanted it while she was lying face down, prone. She likes that position for normal sex, and it excites me, but afterwards she said we should have used more lube.

Is that position, where her legs are together, naturally so much tighter that it’s likely to be painful? I can certainly go wild with the lube, but I don’t want to use a position that is going to be TOO tight.

Thoughts?

I’ve been in that position as well, and as your wife found out, it is much tighter. I’m not sure if the anus is much tighter when the legs are straight together as much as the thighs are getting a lot of friction. You also have your full weight on top of her.

I personally like this position, though not more than the others. We certainly don’t do this position too often. It is part of the repertoire, and we enjoy it for what it’s good for: a tight hot and heavy fuck.

Love, Lust and Liberty,
May Ling Su