Q: How can a butch approach a femme about anal sex?
A: Anal sex is one of those things that usually has people at either extreme. Girls love it or they hate it, but almost no one is ambivalent about it.
Like all situations involving a new sexual activity, the easiest way to find out if you can try something new is to ask. You could just ask her if she wants to try anal with you. If you fear a look of shock and disgust in response, you could try a slower and more nonverbal method. Next time you and your femme are naked and happy together, touch her ass more than usual. Be very conscious as you do this and gauge her response. If she likes what you’re doing, go closer to her anus. As long as she’s enjoying what’s happening, you can bring yourself all the way to touching but not entering her anus. Make sure she knows how hot you think this is. Tell her exactly how hot you think this is. Feel free to even express your desires about further anal activity.
One possibility is that this is exactly what she’s been waiting to hear and she’ll encourage you right away. Another possibility is that she’s going to enjoy what is happening while trying to pretend that she didn’t hear that. In the case of the latter, don’t push it. After you’ve both enjoyed your orgasms and are calm and relaxed, you can bring it up again. This is a less threatening scenario, because no one is trying to get off. You can tell her again how hot you thought playing with her ass was and how much you would like to try anal sex with her. Listen to what she has to say. If she has fears, listen to her, acknowledge her fears, and address them if you can. Hopefully, the combination of liking what was done so far and knowing how much you want it will lead your lady to enter the well-lubed world of anal sex with you. Good luck!