If anal play is something you or your keyholder wants to do, some training is needed. The way I learned to accept butt plugs and dildos was by toughing through the initial pain and eventually learned to relax enough to painlessly accept objects back there. The key to accepting anal visitors is to learn to relax the sphincter. This is achieved by learning to accept small objects and once comfortable, moving on to a larger size.
First and foremost, lube is very important. We use Boy Butter. This product is very slippery and washes off easily. Use a lot. Some people get medicine syringes, the device used to shoot medicine into a child’s mouth. First, using your finger, lube the anus outside and and in. Then, fill the syringe with the lube. It holds about a teaspoon. Insert the syringe in the lubed anus and squirt the lube inside. This will make insertion easier and safer. Most pain associated with anal play is caused by lack of lube.
Many keyholders start with a finger. If you wear an examination glove, it smooths out the bumps on your finger and is easier to take. Lube your finger and slowly insert. Hold it inside for a while. Give him time to get used to it. Now, gently remove your finger and insert two. The idea is to allow him to relax to accept larger objects. I’ve always wanted to be fisted, have Mrs. Lion get her entire hand up to her wrist inside me. So far we have been unsuccessful; more about that later. Once he is comfortable with two or three fingers, you can move on to a dildo or butt plug. Start small and work up the sizes. Bear in mind that in the beginning he won’t be able to hold something up there very long. If you continue his training on a regular basis (highly recommended), every other day work on size and endurance. It won’t take very long before he is trained to accept what you would like to insert. Once he is comfortable holding an object up his ass, start training him to take movement. Use a dildo and slowly fuck with it. Don’t pull it all the way out, just gently in and out. Over time he will learn to manage it. Once he has, try removing it all the way and thrusting it right back. This increases the sensation for him. He won’t like it at first, but will learn to accept and even enjoy it.
In the beginning, or after a long time since his last insertion, an anesthetic cream will make it easier for him. Res-Q is a reasonably priced product that will help. About 20 minutes before you want to start, apply it liberally to his anus, inside and out. It takes at least 15 minutes for the anesthetic to work. Even if you want him to experience the discomfort of anal play, this is a very good way to start or restart activity. After a couple of sessions with the anesthetic, you won’t need it any more. Using it makes it easier for him to deal with the initial discomfort. After that, he still has to learn to handle what you want to do back there.
Bear in mind that you can’t just shove a big dildo or butt plug up his ass. You can injure him. Take his complaints seriously. This is one activity where you need to go slow and minimize his discomfort. If at any point you see red blood, stop what you are doing. If there isn’t much blood, it is probably a little tear or hemorrhoid that has been disturbed. Keep an eye on him. If there is more than a little bit of blood, you should go to the ER to have him checked out. It’s very rare that there will be blood. Anal bleeding is never normal and should be watched. Gradually increasing device size and letting him control how much you do will help prevent any injury.
I mentioned fisting before. I’ve wanted to experience this. Some years ago I asked an acquaintance who fisted almost every man she did a scene with, how she did it. The image at the beginning of this post is the proper hand position to use for fisting. The idea is to very slowly, it takes at least 45 minutes, insert your hand past his anal sphincters into his large intestine. There are two anal sphincters, the obvious anus, and another a bit inside. You will feel them both. Remember, this is a very gradual process. If you are very determined and he can take the discomfort, you can do this in a single session. Most guys need at least several sessions before you will get your entire hand in. Using a glove makes the insertion more comfortable for him (smoother). Remember, safety first. Take his feedback very seriously. Have fun!