Message: How Do I Get My Male Partner Interested in Anal Play?
Brook: For two years of our relationship he has been vocally anti anal… in the process of moving in together he saw my plugs and has made a passing comment about fucking me while I am wearing one.
How to I encourage this interest and hopefully convince him to eventually fuck my ass?
Ease him into it. He’s already gone from being completely anti-anal to expressing an interest in vaginal sex while you’re wearing a plug, so that’s progress.
Surprise him with one of your plugs in your ass when you have sex, and just leave it in during sex. If he enjoys it, make it a normal thing. When you have sex, put a plug in.
After a while of that becoming normal, try talking to him about it again and see if he’s interested in trying anything else, like fingering your ass or using a dildo in it during sex, and then from there, tell him you really enjoy anal play with him and you’d love him to have anal sex with you and ask if he’s open to the idea now. Don’t make him feel bad or put on the spot, just try to have an open conversation about it and see what his concerns are, tell him it feels really good for you and you love doing it, and try to address any fears he may have about it.