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Maria: The basic answer is yes, it's possible. It's called fisting, and it's a major area of play for gay men, both those into power exchange and those who are otherwise vanilla. I'm not super-knowledgeable about it--I've never done it, although I have watched it. Google 'gay fisting' and look for pages that offer instructions (as opposed to the porn, although that might be instructive for you).
1) Make sure your nails are trimmed down close to the finger--no points, sharp edges, or anything that could nick the colon. There are special disposable fisting gloves you can buy to reduce the risk. They're usually black rubber and quite slick. If you really get into it, get a pair of permanent rubber fisting gloves.
2) Get a lube intended for fisting. Regular lubes may not be greasy enough for it. Use LOTS of it. Fisting is messy that way, so make sure you have a supply of towels.
3) Give the fistee an enema, unless you really don't mind shit.
4) My understanding (and don't take my word for it) is that you should gradually loosen up the anus with one finger, then two, then three. When you're (meaning both you and the sub) ready to go all the way, bring all five fingers together in a loose point and SLOWLY work it in. The trick will be getting the knuckles in--that's the widest part of the hand.
5) Go VERY SLOWLY. The fistee has to feel relaxed in order to loosen up enough. If at any point he thinks he can't take it, pull out and let him relax before trying again. It might take a couple sessions before he feels ready to go all the way.
6) A small amount of blood is not uncommon with anal play, but if the fistee begins to actively bleed--dripping or trickling out, that might indicate a cut or tear. If so, it's time to go to the hospital and have it checked out.
7) Consider using a dildo or butt plug to loosen the anus first. There are also special anal speculums you can get to help spread the anus.
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