Use a Water Based Lube.
When fisting, Lubrication is mandatory and a polyurethane glove can do wonders as latex grabs the skin to much and can hurt. When you start to get "lubed up" feel free to make a mess, gently push lube into the orifice with your fingers. Make sure the stuff is all over your hands and fingers and once you start to play keep applying lube as you go, and once again use a water based lubricant like astro-glide(oil-based lubricants dissolve latex).
Start slow.
Start with one finger, and as they relax you can try and slide in more. NEVER force your way in, if they are only comfortably with 2 fingers, then play with them using two fingers for as many days or weeks it takes to stretch them out enough for 3. Keep giving them slow and gentle stretching sessions until they say no more or you can fit your hand inside.
The Fist.
When you get five fingers inside you need to be VERY aware of what your partner is feeling, they will either be in a great deal of pain or pleasure. If you feel them "grab" your fingers/hand with their rectum or vagina, don't move until it is over. This is their body telling you it has had enough for now so slowly pull your hand or fingers out AFTER the body stops contracting on your hand and fingers.
However if you can feel them gently trying to push you out which naturally opens them up more then it should be ok to slip your knuckles inside, folding your thumb inside your fingers. You DON'T need to clench your hand or anything else, and be careful with your nails as you form a fist.
Let her/him lead.
Listen to your partner and let her/him tell you what they like, this way you can always give them what they want, using more or less of your hand or fingers. Do not be rough with someone's insides when fisting or you can cause muscle and tissue injuries. Some discomfort during fisting is normal, but you have to take her/his word on the difference between a good hurt and a bad hurt.
All In.
The knuckles are the widest part of the hand and the most difficult part to get inside. As you feel their body resist at this point, wait for your partner to relax and let you in. You may want them to slide you in by taking your wrist in their hand and pushing you in or by bearing down (as if giving birth or in a bowel movement). Once your knuckles slip past the ring of muscles around the vaginal/anal entrance, you can roll your hand into a fist.
Voila!
At this point, your partner should be in control, let them use your hand as a sex toy and show you what they want, keep talking to them as you play and understand this will produce extremely intense sensations for them.
When you’re done, make your hand into the wedge shape again, and gently slide out slowly and naturally!
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