“How do I introduce my boyfriend to the concept of pegging [the act of inserting an object, usually a dildo, into another person’s anus]? We have done butt stuff but I’m worried he will freak out.”
Okay, so the fact that you have already explored anal on your side is very reassuring. Not that one butthole equals another, but at least we know that he is not scared off by the whole concept.
The best way to move through this is not with the intent to convince, but rather the intent to build the kind of trust that makes asking for what you want easy and low-stakes. You should never punish his fear or disinterest. And start slow, asking questions like “are you ever curious about how it feels?” If he is very disinterested, it has to be okay. You are allowed to have feelings of disappointment, but men also struggle with sexual expectation. The last thing you want to do is establish a precedent that his ‘no’ means less than yours. The best trust building exercise is a “no” followed by an “all right, that’s fine. I’m happy to do something else.” A comfortable no is a sign of good sexual boundaries.
But! If he says yes, there is a world of products and safety procedures to consider (yay!). First, go read the MHN piece about anal by the former Never Fear columnist and love of my life, Rachel Richards. You will need a harness and a toy (or many!), so shop around and choose together. If you buy non-porous silicone, use water-based lube. If you only have silicone-based lube, use a condom. I would also suggest getting other fun toys that give you many options — vibration, plugs and beads. I know that can stack up price-wise, but both of you can use them! And it’s endlessly better to have choices if things aren’t working. In the end, anal is about communication. Emotional safety is just as important as physical safety.
If you have a question you’d like our columnist to answer, send it to
neverfearmhc@gmail.com.