A taxonomy of assfuckers.
“Contrary to easy supposition, I do not believe that it is the arrogant, macho man who is the greatest ass-fucker: he is the asshole. That guy probably doesn’t even like women, he’s too busy competing with other men. In my limited experience, the great ass-fucker is the patient, gentle man, the one who knows how to listen to a woman, how to be with a woman, and has the equipment that can slow her down.”
— Toni Bentley, The Surrender
Not all assfuckers are created equal.
There are, in my experience, at least three types of assfuckers*, each of whom brings different assets and challenges to the table (or, if you prefer, the bed).
First there is the Selfish Assfucker, who is arguably the most common sort, owing to the fact that most people, generally, are selfish lovers, and assfuckers are, you know, just people.
Despite the name, the Selfish Assfucker is not necessarily a bad or ungenerous partner; to the contrary, I’ve had plenty of lovely experiences at the hands** of a Selfish Assfucker or two. They are selfish, not because they because they are inherently cruel or unkind, but because their primary motivation is the pleasure that they, themselves, receive from the act of fucking an ass.
The beauty of the Selfish Assfucker is that they will always show enthusiasm for fucking your ass. If you are the kind of person whose level of arousal is directly correlated to the strength of someone else’s desire for you, the Selfish Assfucker will do well for you on that front. The Selfish Assfucker overflows with desire, the Selfish Assfucker is always hungry, and your ass is the only meal that can leave them truly sated.
The problem with the Selfish Assfucker is that your pleasure is not their priority. This is not to say that they are against you experiencing enjoyment — to the contrary, many a Selfish Assfucker takes pride in knowing that you orgasmed after feeling them in your ass — but rather that when your enjoyment gets in the way of something that they want, it will automatically take a backseat.
At best, this means that being with a Selfish Assfucker requires taking responsibility for your own pleasure and being prepared to advocate for your own needs. At worst, it means, well, something rather dark. Those stories you’ve heard about anal lovers who ignore their partners’ cries of pain, or encourage them to employ numbing agents to their assholes rather than patiently and diligently doing some warm up? Selfish Assfuckers all. In my own life, Selfish Assfuckers have been the ones who have done the most damage, their enthusiasm for my ass matched only by their inability to comprehend my boundaries as something real and inviolable.
On the other end of the spectrum, we have the Reluctant Assfucker. It is hard to say how many Reluctant Assfuckers there are in existence, mostly owing to the fact that many Reluctant Assfuckers will never become assfuckers at all. As their name suggests, Reluctant Assfuckers are not driven by some primal, all-consuming desire to fuck an ass; to the contrary, they come to anal insertion out of a desire to please a partner.
If you are an extremely self-motivated assfuckee — the kind whose pleasure is derived purely from the sensation of something, anything, up the ass — I can certainly see a Reluctant Assfucker doing well for you. Reluctant Assfuckers are compliant and happy to oblige; even if it’s not their first choice of orifice, they will usually derive a fair amount of pleasure from the act of assfucking. And unlike Selfish Assfuckers, Reluctant Assfuckers are entirely here for your pleasure, and your pleasure alone: if you are not taking enjoyment from what they are doing for you, then the exercise isn’t one worth engaging in for anyone.
I must profess, however, that I, personally, do not enjoy a Reluctant Assfucker. In my own sex life, I’m the type of partner who needs to know that, whatever you are doing with me, you are truly into it. While I can respect someone’s attempt to be — in the words of Dan Savage — good, giving, and game; the knowledge that someone is merely doing me as a favor is the ultimate boner killer. If my partner, themself, is not all about that ass then it dampens my enthusiasm. And given the amount of work involved in prepping for anal, in preparing the ass, I need a lot of enthusiasm to get myself to do it. If the assfucking experience is for me, and me alone, there’s no need to involve a partner — I can just use a butt plug.
Lastly, we have the rarest assfucker of them all: the True Ass Romantic. In my decades of sexual activity, I have only encountered the True Ass Romantic twice.
Unlike the Selfish Assfucker or the Reluctant Assfucker, the True Ass Romantic is not motivated by the desire to simply pleasure or be pleased. The True Ass Romantic is motivated by a deep, pure, and all-encompassing love of the ass, one complete with the knowledge that the ass is a territory best approached with patience, skill, and romance***.
I do not know how one becomes a True Ass Romantic, I have only had the pleasure of meeting them when they are fully formed. I can say, however, that they tend to be — as Bentley surmises in the quote that opens this essay — gentle and caring people, truly invested in the well-being of those they take to bed. They are also, in my experience, intrigued by the asshole out of a desire to more fully know a person: the pussy and the mouth may easily offer up their secrets, but the asshole takes work. The True Ass Romantic understands that taking the time to do that work, and do it well, can offer one access to an entirely new plane of connection with a partner.
I first discovered the joy of a True Ass Romantic in my early twenties. We’d connected initially through a LiveJournal Meetup at held at Remote Lounge****, back when I was nineteen. A few years later, when I was a year or so out of an abusive relationship and maybe six months out of the heartbreaking rebound that had followed it, I found myself on a date with this True Ass Romantic.
I’ve written about this man before — he appears as a character named Malcolm in a comic collection I created based on some LiveJournal entries from my early twenties***** — but what I have never revealed is this. He was not merely a kind man twelve years my senior with whom I enjoyed a very lovely casual relationship for several years; he was also the first person to truly help me understand the beauty of what assfucking, what being assfucked, could be, a person who well and truly earned the nickname The Ass Whisperer******. He was the first person both willing and able to patiently open me up with fingers alone, the first person whose desire for my ass did not feel willing to run roughshod over my own safety and wellbeing.
He was, ultimately, the person who helped transform me, myself, from a Reluctant Assfuckee to one who understood the act, not merely as something that was hot because of other people’s desire for it, but something that could put me on the path to a greater and more fulfilling pleasure myself.
That, I think, is the power of the True Ass Romantic, and it is why I hope that everyone who opens their asshole up has the pleasure of encountering a True Ass Romantic at least once. They are rare — and sometimes our time with them is only intended to be brief! — but even in the scope of a single sexual encounter, they have the capability of wildly realigning one’s understanding of what it can mean to be fucked up the ass.
* In your experience there may be more! I do not profess to have caught all the existing types of assfuckers in my game of buttfucking Pokemon.
** And other body parts
*** I use romance here, not in the sense of chocolates and flowers, but in the sense of offering an inordinate amount of attention and care in the hopes of encouraging another to relinquish their barriers and open up for you
**** I am cringing at the sheer early aughtsness of that phrase
***** A comics collection you, yourself, can purchase by sending me $25
****** Look, Cesar Milan’s reality show had only just come out one year prior, okay?