One of the most common questions I get from beginner bottoms is “how long will it take before I can take a whole fist?” As I mentioned before, the most sincere response to this is along the lines of: “It depends, everyone is individual, you won’t know until you try, yadda yadda yadda”. Any answer giving a number is going to be a vast generalisation. There are many factors that will affect how long any given individual will take to “open up” their first time, including their physiological make-up, their level of experience with assplay in general, including how frequently they practice alone or with others, the state in which they play (obviously various chemicals of varying legality have a varying impact…), and so on.

In this post, however, I am going to risk making that generalisation, based on the couple of dozens of “virgins” I have trained in fisting, and then I will try to explain why, in my opinion, that number seems to apply to most people. In short, while this number is definitely not true of everyone, what seems to work for most bottoms is: two. Yes, I was able to fist most guys the second time we played together. Does it seem too short, too soon, too fast to you? Well, it does to me too. I wouldn’t have guessed this when I started. Because it seems so counter-intuitive I have spent a lot of time thinking about this. This is what I will be sharing with you in this blog, the three reasons I believe that twice is generally all it takes for a bottom to take a fist, in most cases.

Reason #1: Self-screening (and, I guess, regular screening too). Someone who decides to have one go at fisting might just be feeling curious, adventurous, or optimistic. Somebody who decides to give it a second go, is more or less committed. They probably enjoyed trying the first time, and think they can get even more pleasure by continuing. They also understand that it won’t be an easy, automatic process, and what the balance of effort/pain and pleasure is. (Nobody can tell me there isn’t some degree of pain associated with getting your asshole stretched, though I would argue that when done right fisting really shouldn’t hurt any more than vanilla sex). Those who were disappointed or disillusioned by their first experience, or even just their first experience with me (hey, you can’t please everyone), will obviously not return for seconds. Repeat customers know what they’re getting in to.

Reason #2: Trust and connection or, the survivor factor. One major factor I didn’t include in my introduction to this post that affects how easy or hard it is for one to get fisted is trust. I believe that 90% of bottoming is psychology – mind over matter, if you will. This is why so many guys think it’s impossible to do without drugs, even though some drugs arguably make it physically harder not easier to get fisted. Getting fisted is easy, compared to getting fisted by a stranger. Someone who meets with me a second time, naturally, is much more confident that they are safe with me, and that I know what I’m doing – after all they survived the first time and they came back. Moreover, they know it’s going to be fun, even if they don’t manage to take a whole fist this time either. They become much more comfortable with taking direction, trying different positions, and generally make the process a lot more fluid.

Reason #3: Duration. There are many aspects or “skills” a bottom can work in when they try to make progress in fisting, and I believe it’s best to focus on them one at a time. I’m talking about things like depth, width/stretch, speed, etc. Of all these I believe the most important one, and the one to work on first, even before you can take a fist, is duration, by which I mean how long you can make a session last. I guess you could also call it endurance. The problem is, if all your sessions are short, you can never make any other kind of progress. Why do I think duration is so often improved the second time? Ironically I think it is partly because the expectation of taking a whole fist is no longer there, since they realised the first time that that was not a requirement, neither for my enjoyment nor theirs. They realise there is no need to rush. Another aspect of this, especially of true of younger bottoms, is the fisting equivalent of premature ejaculation – this generally happens with guys who play with their penises during fisting. Most beginner bottoms cum very easily while being stretched, and that puts an end to the session. As they gain more experience, they understand that their penis doesn’t need to be involved in the process, and that their true orgasms come from inside. In addition, once I realise this problem the first time, I can make suggestions to prevent them from making themselves come, such as keeping a rubber jock strap on; a milder form of chastity.

I realise that by writing this I might be working against myself. If people have the expectation that it should (only) work the second time, it could ruin both the first (by giving up too easily) and the second (by creating unrealistic expectations). If you are a beginner, however, you should really not take this “prediction” very seriously. Relax and do what feels right, for as long as it feels right. At this point you’re not just trying to get fisted, but also learning a lot of about how  to get fisted: what positions work for you, whether starting with toys helps, what your response to poppers (if any) is, whether straight or turning entry feels better, whether certain things trigger you to tighten up, and many other things you will only learn by trying. Make a note of these things, and let the top know about them. This is teamwork. Nobody can really predict how long it will take, so just make sure the process is enjoyable for both of you.