Back in my academic days, a criticism professor told me to look at every work of art as a new planet: unique, self-contained, unexplored. I do not know how much astrology she actually knew, but the metaphor was well chosen. A planet has its own gravity, its own atmosphere, its own day and night cycle, its moons, its sky, its own climate system, and, if the planet can support life, a whole new biology. It has its own rules: days might last minutes or weeks, the moon (or moons) might rise or set in the North, and the winds might change the landscape every day – or hour. Are you asking what this has to do with fisting yet?

For me, one of the most exciting parts of being a fisting top is discovering a new bottom. And this is where the metaphor comes in. I see that process like exploring a new planet. You come armed with the skills and experiences you have gained in the planets you have encountered before, but old rules do not apply. Prepare to be surprised. Even after all these years, I still learn something from every bottom I play with, whether they are experienced, in which case they might guide me to a discovery, or not, meaning that we are exploring new things together.

This is why I refuse to respond to the question: “What is your fisting style?” That is like asking me to make someone a three-piece suit before taking their measurements. I develop my “style”, if we must call it that, each time I play with someone, by being receptive to the feedback I am getting from them, whether it is spoken or non-verbal. Bottoms have very different communication styles, and as a top learning to pick up on subtle signs is part of the job description. And if that’s not working, do not be afraid to ask questions. It will be more fun for everyone at the end.

So what are some of the questions you can ask while performing this exploration, whether for yourself as a bottom, or with each partner as a top? They are far more than what I can list here, and some are more important than others to each individual, but this will get you started:

  • What position or positions work best for the bottom? Are some positions better for certain things? Do they tire easily in some positions (such as on their knees)?
  • Which lube or combination of lubes works best? This is not just a physical question, a lot of bottoms have an almost “aesthetic” preference on this subject. Some like to feel wet and sloppy, others are minimalists.
  • What is the best way to start? Some bottoms have a negative reaction to too much “teasing”, while others find it the best way to relax.
  • Will toys help? What kind of toys? Once you understand what sensations work best for the bottom, you will have a good idea of what toys you might want to use. I mentioned this before, but I use toys to achieve effects that I cannot create with my hands. For example, when I recognise that a guy really gets off on the moment I pull my fist out of them, I will bring out the anal beads: using them I can give them that same sensation three, four, or five times in a row, depending on how many beads they can take inside them.
  • What is the best way to manage time? Short sessions with small breaks, one long marathon, two sessions with a longer break? Of course it depends on what other activities you have planned for the evening, if you are fitting fisting into a bigger scene. In general, a warning: if you are having multiple sessions with breaks expect each successive section to last less than the previous one.
  • Following from the previous question, after a break, is it back to square one? Some bottoms will tense back up, whereas others will stay relaxed, even gaping during your break.
  • What do they derive most of their pleasure from? The stretch of the sphincter? Prostate stimulation? Friction? Vibration? How can you adjust your technique for that?
  • Are there any sensations you need to avoid? For example too much rotation of the hand can wear some guys out very quickly.
  • Does verbal encouragement (and what kind of verbal encouragement!) help? I find this important with bottoms who tend to hold their breath at “critical” moments – and holding your breath is the worst thing you can do while getting fisted.
  • Does the bottom know when it is time to stop? You might not agree with their judgment. Sometimes you will be able to tell that they have had enough before they do. Sometimes you will be certain that they can push themselves a bit more and finish on a high note, but unless you know the person well it is better to err on the conservative side.

You can probably tell there are many more questions that can be asked, some of them as simple as “how rough”, “how fast”, “how deep”. The more sessions you have with a bottom, the more complete your exploration will be, and the more useful your discoveries. And of course from the bottom’s perspective, you need to be asking these questions for yourself, to figure out what works for you. The key here is experimenting.Try every position, try every kind of lube, latex and nitrile gloves, different kinds of poppers if that’s your thing: you get the idea. When you are just starting out, finding a reliable top who is open to helping you with that exploration is the fastest way to make progress.

Discovering a new bottom – like a new planet – is exciting and invigorating. It is embarking on a new adventure. However, playing with a well-explored, familiar bottom is rewarding too. It feels like putting on a well-worn shoe – or Handschuh. Especially if you have not seen each other for a while, it feels a lot like coming home. But you need to put in the effort first: ask the questions, look for the signs, don’t make assumptions, map the territory and respond to the environment you find. You are being welcomed into a whole new world.