Tales from the Tail —Going Deep into Fisting

Client’s Tale

When most people hear the word “fisting”, they immediately clench their butt. It’s a pretty interesting topic of conversation, wouldn’t you say? Lately, it seems it’s becoming quite popular among NYC’s young gay scene (and probably beyond). What used to once be an isolated kink, reserved for guys who hung out in leather and fetish bars, is now becoming a routine act within the queer community, even for the twink next door. I spoke with our Aesthetic Nurse, Chris Bustamante, recently and he said that this past month alone, he’s had three friends tell him about their experiences being fisted, all of which were very different. So, buckle up your hole because it’s going to be a deep and knuckley ride.

Friend 1:

It was just another casual Friday night and I found myself hitting up my FWB because it’s been a minute since I’ve been dicked down, and that’s not cute. Once he got back to me, I had already started the process of getting ready and cleaned out. I don’t consider myself a size queen by any means, but lately I’ve really enjoyed the feeling of being really filled up. My friend and I have been toying (no pun intended) with the idea of fisting my hole. I don’t even really know how it started. The first time he tried, it was just two to three fingers and him massaging my prostate (bliss). The second time, he got all four fingers inside me and I found myself loving it (total euphoria). It feels like a challenge. I don’t think I’ve felt that from sex in a while. Something to work up to feels exciting and completely gets me hyped up to fool around. Then, the last time we fucked, we were really going at it. It wasn’t too long before he was ready to finish, but I was saving myself because I had other plans on my agenda. Shortly after he came, his hand made its way to my hole. I was completely relaxed, lubed up, and ready for it. He started playing with my hole — first, three fingers in, then four, and then… his entire hand. Once the thumb went in, it was a completely different feeling. I’m not sure if it was more physical or psychological, to be honest. I had accomplished this sexual taboo, this anatomical feat, and suddenly I felt incredibly sexy and that “full” sensation I thought I knew was taken to a hole new level (in a good way). Needless to say, I got off — hard. I’m not sure where this fisting journey will go from here. I enjoyed it, but I certainly don’t feel like it’s something I need to keep doing on a regular basis. Only time will tell, I suppose, but for now, mission accomplished.

Friend 2:

It’s Saturday night and I’m pretty tipsy. I had been chatting this guy up on Grindr for the last week and we were supposed to meet up the night before. I decide to dip out of the bar and head to his place. First time encounters always have a little bit of that initial awkwardness about them, but things smoothed out quickly since we were both buzzed. The forelay was hot and we quickly got down to business. I hadn’t douched, but I know my body and felt ready. He’s down there eating me out and I’m feeling all sorts of right. As he starts fingering me, I immediately open up and I can’t help but get lost in the moment. Between the kissing and sucking, my hole is in ecstasy. Before I knew it, he had all of his fingers inside me. Woah! I’ve been down this road once before, but it was post-sex and my hookup was just playing around with my relaxed hole. I was kind of shocked that this happened before fucking, but there was no pause. He eventually took his hand out and proceeded to fuck my brains out. I left the next morning extremely satisfied, yet slightly confused about where last night’s hole play would take me next. I don’t think “fisting” is appropriate here because neither time did the top make it up to their wrist, but maybe that’s just me being a prude.

Friend 3:

It was the weekend and I decided I wanted to do something different other than going out to the local bars. I met up with some new people, one being some dude I was chatting with on Instagram. We met in person and he was kind of weird, but I went along with it. We went to a house party, one thing led to the next, and suddenly the party had escalated into an orgy. We were all making out and groping each other, when one of the guys started eating me out and playing with my hole. I returned the favor and after sucking his dick for a bit, we both realized that he wasn’t going to get hard enough to fuck me. Not letting this get in our way, we started getting handsy with each other’s holes. He started fingering me, and all I could think of was, “I want his fucking fist inside me!” I had never been fisted before, but I was feeling extra adventurous that night. Well, he wasted no time and dove right in. First, three fingers, then four, and then his whole hand was inside me. It was aggressive, but I wanted it and when you’re on the same page mentally and physically, everything just fits (pun intended). However, eventually, I started to feel more pain than pleasure and asked him to stop. The rest of the night carried on, but my hole took a break. The next morning, I noticed that my hole was more sore than I’ve ever experienced before. Then, I noticed I was bleeding and it felt terrible. I went and got it checked out and learned that my hole had been torn in four different spots and, as a result, I had developed hemorrhoids. I started using PreparationH and stopped engaging in anal play to let my hole heal. Fortunately, within a week, I felt almost normal again, but I’m continuing to play it safe and lay off anal play for a full month, until I know things are back to normal. Fisting was definitely something I can now check off my bucket list, but I’m not sure yet how soon I’ll be running back to getting fisted.

My Discussion

Fisting has been around for ages, even though most people think of it as an act developed in the 20th century that’s only practiced among gay men. Believe it or not, those outside the queer community also engage in both anal and vaginal fisting and some theorists believe its origins actually date back thousands of years. It really hit its peak in the 70’s and 80’s within famous fisting clubs (the name I especially love is the Handball Express). However, shortly thereafter they were forced to close because of the concern of HIV viral transmission. Recently, we have seen quite a resurgence, specifically in our youth, and with the lack of formal education and training, we felt the addition of fisting to your sexual repertoire needed its own blog post.

The art of fisting is indeed an art. That said, the finished product, or full-fist acceptance, needs to be a planned approach, not an accidental slip of the… hand. Both major and minor complications can arise when proper form is not used. And just like cock-in-ass penetration, experienced participants — both top and bottom — is a requirement, specifically with these more advanced practices.

First and foremost, if you can’t even take dick, forget about a fist (for a while at least). As with any sexual acts involving the ass, the best is to start with sequential anal dilators or butt plugs over a series of weeks to work on stretching both the skin and underlying muscles. 2–3 times a week with gradual pressure in and out for 2 sets of 15 or so. I find that many people can fully open their internal muscles; however, the skin is their limiting factor. Gradual manipulation with controlled pressures can slowly start to work these regions, eventually allowing for complete relaxation. It can takes weeks to months, depending on your limitations.

Once you’ve mastered the full dilator set, next comes adding in larger dildos or toys that mimic fisting’s girth, length, and angulation. Again, this requires incremental advancements and any forced entry can lead to injury. I cannot stress how you can never use too much lube. When it comes to bigger things, most people turn to Crisco or J-lube because of its slickness and longevity. Remember that the distal muscles are the first barriers you will encounter, but as you snake your toys (and eventually a fist) upwards, the anatomy is such that an angle in present, usually to your left. The fister should know how to manipulate around everything; however, you can arch your back, choose better positioning, and/or sit more upright to open up that angle. I suggest using these larger toys on your own to see how to incorporate breath and also change your pelvic angle, as well as your torso, to be able to accept whatever is being inserted.

At this point, if you feel confident that everything has been strengthened and you have been successful with toys and the like — boom! You are ready for the beginnings of fisting. However, I think it’s important to manage expectations because your first attempt is most likely not going to be 100% successful. It’s all about baby steps and setting realistic goals. Find a partner who is aware of the appropriate techniques for fisting and also implement a safe word or pre-game discussion, making sure you don’t find yourself exploring parts unknown without a plan in place. Another thing: it’s called fisting and not punching for a reason. Fisting is slow and steady with gentle, controlled pleasures. It should be thought of as: Fine Insertion Stretching Technique. Use your toys first as this not only allows for complete relaxation, but also deeper pre-lubrication. Second, you may have seen a fister’s hand position look a “silent duck” or be referred to as “duck-billing” and that’s simply because all five fingers are kept aligned as tight as possible, resembling the beak of the duck. Before you can get into all five fingers, start again with gradual insertion and slowly lead up the grand finale of the coveted five.

For the most part, the hardest component of fisting is the initial entry. Hence the reason why the duckbill shape is important. This overcomes the tightest region — the three distal muscles or sphincters — subsequently allowing the wrist to be gripped by this underlying muscle. Clearly, even if you have big wrists, the girth of your wrist is smaller and more manageable than your fist, so once you make it over this hump, you should be in a better position (no pun intended). Next, it’s important to remember the angles from anatomy class. After you insert beyond the muscles, most people’s colons turn to the left and that needs to be taken into account. Many toys don’t pre-lubricate that high up, so more lube is absolutely necessary. Please make sure you are constantly slowly maneuvering in and out with a twisting motion to allow for complete lubrication and relaxation. And I can’t mention this enough: slow and steady wins this race and don’t get discouraged — it may not be a full fisting success at the beginning. Stay with it. Be present and persistent.

Sometimes, no matter what you do, it just isn’t gonna happen. Either the skin rips, the muscle limits your expansion, or you just can’t navigate fully in. All of these are inevitable for some, so do not feel as if you should quit what you have set out to do. From proper evaluations in our offices, to Botox for relaxation, to surgical techniques — you have options. There are myriad approaches that are available to successfully marry your sexual desires with the physicality of fisting.

What about cleaning out? I do have some final thoughts on all the preparation that is required for fisting. The above dilation protocols are paramount to successful engagements. But it doesn’t stop there. Many people use either laxatives to flush things out or gut de-motility agents (like Imodium) to slow things down, or a combination of both. Please keep in mind that chronic use of these pharmaceuticals can create dependency, leading to permanently altered mechanics.

When it comes to douching, aggressive cleansing with larger douches or shower hoses are needed for upper rectal and lower colon cleansing. However, these methods strip the lining of the anal canal and rectum, ridding your homeostatic flora, and increasing potential complications, such as STDs and injury.

Lastly, the bigger we take, the larger our holes get. The best analogy is the gauges that people put in their ears. Over time, you need larger and larger plugs to fill the space, and then, at some point, the skin simply can’t go back to its original size. The same theory can be applied to our asses or colon. The recoil of normal muscle may be chronically altered so much so that you could be constipated or, worse yet, develop rectal prolapse where your insides come fully out of your ass. If you started fisting at a younger age, it’s important that we prevent all of these potential complications from occurring, since so many of them are inevitable if fisting is not performed correctly or if preventative measures are not put into place.

At the end of the day, I don’t have all of the answers. And I am sorry if I have not painted a very sexy picture when I described everything that goes into implementing fisting into your sexual play. However, I do want to reassure you that it feels good for some, hence the reason why people try it, and why wouldn’t it? We have so many nerve endings in that region. It’s simply imperative we all understand the risks and benefits of any sexual play, particularly fisting for the purpose of this post. I hope these tales and our discussion have provided a resource to not only educate everyone on all things fisting — the good, the bad, and the ugly — but also to help minimize any potential complications. At Bespoke Surgical, we even have a pelvic floor therapist on staff who can help with the mechanics of fisting so that you can better achieve your goals. We are always here for all of your anal questions and should you still find yourself looking for more info, or if a visit to our office is warranted to help you through this or any sexual act you desire, by all means, please let us know. Your hole is our hole.

Don’t forget to stay in touch on Instagram: me and Bespoke Surgical.