If you are a first time fisting top playing with an experienced fisting bottom, then the key is to listen to directions given by the bottom. A good fisting bottom will communicate how he wants you to play with his hole – it may be anything from “go slow” to “trash my hole,” but the key is to listen and follow directions. If you are unsure about what to do then ask your bottom for directions.
The more you play with a regular partner the more you get to know how they enjoy their assplay. Regular play builds a connection and as play develops can be more relaxed and more intense.
If you are a first time fisting bottom playing with an experienced (and considerate) fisting top, then you are most likely in good hands. A good top will communicate clearly with you and also prompt you to communicate. He will also respond appropriately to your verbal directions and your body language.
I may be mistaken, but I believe it would be rare for someone to go from fucking to taking a fist straight away. Most guys will stretch their hole with dildo play as they build up to the width of a fist. To best prepare, a bottom will ideally have played with varying lengths and widths of dildos to train their hole to take a fist.
The best way to open your hole is by regular play (both with dildos and fists), and regularly pushing your limits. A tiny (and I mean tiny) dollop of mint toothpaste with baking soda (ie Arm & Hammer) can also help to open your hole. Place a tiny dollop on the end of a dildo, add your lube, then insert into your hole. Your hole will get warm, then your ass will start to excrete its natural juices, and your ass will get really hungry for action. For some, numbing your hole using lube with clove oil (ie the black Boy Butter) or gum numbing gel can help.
Aside from training your hole for width and depth, you can also train mentally for fisting. When you exercise it requires both neural and physical adaption to see improvements in your fitness. Fisting play can also benefit from neural adaption by training your brain. To train your brain for fisting, gradually increase the length of time you play with your ass. This can mean longer and longer sessions. Or you can increase the length of time you have a dildo inside you. Quite often when you play, you get to a point when you feel the need to take the dildo out. Instead keep the dildo inside you and try to go longer. Another way is to increase the length of time before you take a snort of poppers/amyl or if you can, eliminate poppers all together. When you get to playing with a fist, you will find you should be able to take a fist for longer period of time.
Some guys like to use drugs to enable them to take a fist. Some guys can only take a fist (or only want to take a fist) when they are on drugs. Drugs can make fisting a very sexually intense experience, however, fisting can be just intense without drugs. What you do and what you take is up to you, but keep in mind that the risks increase when drugs are used for play (higher risk of injury, risks related to unsafe sex play, etc). I personally do not use drugs for play, except for poppers.
Don’t Make it a Goal to Take a Fist the First Time You Play
Don’t make the object of the night to take a fist. It may happen the first time trying, however, it is more likely to take a couple of sessions before the bottoms hole relaxes enough to take a fist. Take the time to stretch and slowly work his hole with your fingers and dildos rather that pushing a fist in straight away.
Ambiance - Create an environment where the bottom feels most comfortable. Usually I things that remove distractions in a subtle way. Like having the lights low, curtains drawn, and energetic music on low in the background. Sometimes I like the lights on and the windows open. Whatever it is, set up the play space in a way that makes the bottom comfortable.
Set-up – Make sure you have all the things you need set up and on hand: Lube (J-lube or crisco), rags, poppers, gloves, dildos, chairs, mirror, drinks, camera, etc.
Top - Make sure your nails are cut short and filed smooth.
Bottom - You should do a thorough clean-out.
As always, practice safe sex. The risks of contracting HIV and other sexually transmitted infections is much greater for an unprotected (ungloved) top than it is for the bottom. This is because the top has his fists deep in anal secretions and bodily fluids. If a top has any cuts or abrasions on their hands, this constant and extended contact with bodily fluids increases the chance of transmission.
Don’t go straight to a lubed up fist. Really take the time to open the bottoms hole. Rimming, fingering, and fucking are good starters, then move on to two or three dildos that the bottom has played with before. You will know when to move up to the next sized dildo when his hole relaxes and takes the dildo easily. It may also help to run one, two, or three fingers around the inside circumference of his hole (in a circular type action), stretching and massaging his hole to stretch and relax. When ready, you can then start working your fist into his hole.
Taking a Fist
Some guys may spontaneously cum as soon as the fist slips in. Another response is to experience a full body orgasm that last for a few minutes each time. Or even multiple full body orgasms as the play progresses. What ever the response, allow the bottom to experience all the sensations without forcing your fist onto him. Depending on how the bottom feels, he may want to stop after this. Some guys may have a huge release of emotion and may even spontaneously start to cry. As taking a fist is a new sensation and can be intense the first time, the bottom may tell you to fist him for short periods then stop, or he may just say: “Don’t stop!”. As a top, the key is to listen and be aware of your bottom’s reactions and allow them to occur, and respond in a considerate and mindful manner.
Next Play Session
Once you have taken a fist, and have taken 3-4 days to recover, the next time you play the bottom will be able to take a fist a little easier, however, it is still wise to follow the steps above until you get to know your own play preferences.
Can’t Seem to Take a Fist -
Some guys, even after doing all of the above, reach a boundary which seems impossible to breach. Guys often comment that their ass is too small, or their bone structure is too narrow to take a fist. Even after numerous tries with the same or different tops, or with different sized fists, they still can’t seem to take a fist. When I hear this, I know it is not a physical barrier but a mental one. It requires you to push past the perceived physical barrier, but it is that last mental push past the sensations you are experiencing that is required. Once you do this you will be taking a fist.
Seeing Red – A little pink in the lube is usually okay, however, if you start seeing dark red blood then it’s a good time to stop the play session.
Going Deep – Deep fisting requires an experienced top and/or bottom. As a newbie, keep to wrist deep fisting until you build experience.
As a bottom, experience relaxing your hole and relaxing your mind, do more of what feels good, and communicate with your play partner. As a top, listen to your bottom’s verbal cues and body language, and respond in a mindful and considerate way and it will be a special experience for both of you.