This story originally appeared in our Queer Issue on June 4, 2025.

You shouldn’t simply plunge your arm into a lover’s hot, tight, wet hole without a little know-how. Preparation goes a long way to avoiding sore bottoms and fronts, disappointments, and broken hearts. I went deep with a leatherdyke and a leather daddy who have a whole lot (40 years) of experience between them.

A rectal tear is the paper cut of anal sex. Not devastating, but honestly far more painful than you’d think, so we turned to Jim Drew, who started fisting 25 years ago. He’s a vers-leather daddy, board member at Seattle Men in Leather, and founder of the Seattle-area fisting group Menagerie.

How do you prepare a partner (and yourself) for fisting? 

For the bottom, they typically need to douche their rectum and the lower colon. Generally, you put water in and expel it until it comes out clean. The main thing tops need to do is inspect their hands and make sure their fingernails are clipped really short—all the way down where you can’t pick up a dime. Then they need to inspect the rest of the hand for cuts and scrapes. Wearing latex or nitrile gloves is the best way to prevent anything from [passing] between the bottom and the top. But these days, a lot of guys never use gloves. It depends on the partner and the situation, but I think gloves are valuable. PrEP protects against HIV. But it doesn’t do a damn thing against gonorrhea, syphilis, chlamydia, or hepatitis C. 

Let’s talk hand position.

Make a duck. Take your hand and collapse the fingers and thumb like a duck’s bill. That’s going to be about the smallest cross-section for the hand to enable it to go in. Once you have the hand in, then you can make other positions and stimulate sensations in different ways. There’s the standard fisting joke of, “Why are gay men lousy in a fight?” You make a duck with your hand and say, “Because this is what we think is a fist.” Once you have the hand in, then you can make these other positions and stimulate sensations in different ways. Though I recommend against jazz hands and finger spelling.

How much discomfort is too much discomfort?

In general, pressure is the sensation you’re going to feel. If you do feel something sharp and stabby, that’s an indication of “too much,” at least too much for the moment. Tops don’t want to abruptly pull out because that freaks out the bottom. We want to ease off and determine if there’s a need to pull out, to stop and look for injury, or change body positions. When you’re trying to go deep, you want to pay attention to the bottom’s muscle tension and body language, what they are saying or making noises about, to make sure you’re not pushing their boundaries. 

What’s the top mistake?

In any aspect of BDSM, we spend a lot of time talking about “what if ” things go wrong. If the people playing know what they’re doing, the odds of things going wrong are significantly lower. Other than not knowing what to do if there’s an injury, the thing that causes the most problems is having goals that are set too hard and pushing toward them when you’re not ready. You always have to be prepared for the person’s hand to be too large for where you are. Avoid setting things up where, if it fails, you blame yourself. Tops can do the same thing. The biggest sin is trying to push a bottom harder and faster than they are willing and able to take. Each fisting session is its own special, unique thing, that will be different from any other. Laying out expectations is a recipe for failure.

Why should more people try this?

I’m not necessarily sure that more people should try it. I think people should give some good thought to what they want out of their sex life before trying everything on the buffet. Before I got into fisting, I found that I liked bigger cocks and I liked it when somebody would finger my butt during, before, and after we were done fucking, and maybe get a finger or two or three in there. For me, it was a progression. I like this, and I think I would like more, bigger, thicker, deeper. 

Pussy is slicker and stretchier by default (see: childbirth), but less cavernous than ass. A hand could venture for miles up an ass, but here, all sane and sensible roads end at the cervix. Jae Marie is a kink educator, Ms. San Diego Leather 2016, and an experienced practitioner of BDSM. In the leather community, Marie is known as “cold hands,” as in “I’ve got cold hands, do you have somewhere warm to put them?” a pickup line that actually worked for her at a dyke event in 2016. “In four days, I fisted 14 people,” she says. 

How do you prepare your partner (and yourself) for fisting? 

I think it’s really important to understand the intent. Is it something intimate, or is it like, “I need to check it off the list”? When me and my hus-bitch first got together, and I would talk about fisting, I would say, “Have you ever wanted to crawl in someone like they’re a Tauntaun?” That’s what fisting is like. You want to be inside the person you’re in love with. 

As a top, I have to be very careful. I’ve had conversations with people who wanted me to fist them, and after I sussed it out, I was like “Oh, you’re going to fall in love with me.” As a top, I’m also worried about having the right kind of lube and doing my due diligence in making sure that person feels safe and secure. All the dykes that I know, we all joke about like, don’t show up with those Costco gloves. They’ve got a weird seam in them. People can feel the seam. I wear artificial nails. If I have a longer nail with a square tip where there can be a corner, I’ll go for thicker nitrile gloves. If I have shorter, rounder nails, I’ll just use a regular nitrile. I like the purple ones. I think those are cute. 

So nails aren’t disqualifying? 

You can have nails. Especially being a femme, I always have my nails done and I will find a way [laughs]. You just have to have the right equipment—and the right technique.

Let’s talk hand position.

Typically, I would start with two fingers. You go in and you spread them, stretching out the muscles and relaxing them. And when you get a little bit of give, you put in that third one, and fourth one. Once you get to that fifth one, you should have your hand completely closed. Then it’s all about moving it around in a circle until you find that sweet spot, like a key in a lock. At that point, I usually have someone bear down. As they let up, I advance all the way and then do “the tuck,” where you pull your thumb into your palm and then wrap your fingers around it. Then just stay there and wait for the cue. Typically, if your hand is in someone and they’re really into it, they start moving. The biggest barrier between getting a fist all the way in somebody or not isn’t always anatomy. It’s obviously a very stretchy part of your body. It’s typically all focus. And I’ve found that a lot of the hesitancy is from people who have been conditioned to this idea that you have to be tight, because if you’re loose, there’s something wrong with you. Your value isn’t how tight your vagina is. That’s patriarchal, misogynistic garbage. 

How much discomfort is too much discomfort?

It’s important to communicate when something feels off. Not that something feels different, or new, but something that feels off. There’s a risk of tearing—microscopic tears and not microscopic tears—in the vaginal wall. As a top, when you are looking at your wrist, if they’re producing enough blood that it’s coming out as you’re doing it (and they’re not on a menstrual cycle), you need to stop.

What’s the top mistake?

They go too fast. I would say the first time, you could take an hour or more. You have to be ready to hold space. Even people who’ve been fisted a lot, this is not a quickie. Nobody is going that shit they show you in porn where the girl lays down and all of a sudden the hand’s in. That’s for straight people. That is not reality. 

Why should more people try this? 

I think there’s something incredibly freeing about getting rid of the stereotypes about what our vagina should and shouldn’t be able to do. And there’s something so beautiful about finding a space where you can be that way, and be safe and know that you are in control of this happening to you. And that is a mind-boggling space that so many people have never gotten to.