Strictly speaking, anal play has no direct relationship to male chastity. However, when we open the Pandora’s box of caging our cocks, we also open other kinky topics as well. I have mixed feelings about anal play. I really like the idea of Mrs. Lion training me to take butt plugs, dildos, and her hand. It turns me on to think about her doing this to me. When we actually play, I rarely find it arousing and frequently uncomfortable. I think that is part of the appeal. It’s like spanking. I love to hate it. There is a silver lining. As I am better trained, the discomfort will become arousal, I think. For example, I now find the Njoy plug comfortable to accept and hold.
There are a few things I have learned about anal play that I would like to share. The first is for caged males. Anal play is not gay sex. Everyone, male and female, has a large number of nerve endings in the anal area. Stimulation of this area can be sexually arousing. Most men have experienced a finger up there while their partner was giving them oral sex. Once you get over the surprise, it really feels hot. So, keep an open mind.
Second, hygiene is very important. Your partner will probably not enjoy dealing with a smelly butt. Cleaning is easy. The anus is largely self cleaning. All you have to do is make sure the exterior areas are nice and clean. There is no substitute for washing. Either a shower or a soapy washcloth in your crack will ensure your keyholder will have a good experience. The second issue is a bit delicate. The primary function of the anus and colon is excretion. That means there is a good chance some poop is being stored up there. Generally, poop is not down in the lower eight or ten inches of the colon, but it is possible some will be there. This creates two challenges: The first is that it hurts when an object is inserted and pushes poop back up. In my experience, most of my discomfort is caused by this. Second, when the toy comes out, there could be poop on the end of it. You and your keyholder need to be aware of this and provide a paper towel or something to put the toy on until you wash it. By the way, silicone toys can be boiled or run through the dishwasher for extra sanitation.
When Mrs. Lion and I started playing years ago, she began each session by administering a disposable enema to me. Disposables don’t put a lot of fluid up there and are not uncomfortable. Holding it for about fifteen minutes and then taking the time to let everything out eliminated mess on the toys and my discomfort from a toy hitting poop. You don’t have to do this. Just keep it in mind if you are finding insertions uncomfortable or messy.
The keys to comfortable insertion are lube and insertion speed. Most anal pain from toys is caused by lack of adequate lubrication. Use a good lube and plenty of it. We use Boy Butter. It’s inexpensive and long lasting. Use plenty. If during insertion, things get painful, withdraw the object and add more lube. Chances are very good that will cure the problem. Speed of insertion is also key. Slow and steady wins this race. If it starts to get too uncomfortable during insertion, back off a bit (remove an inch or so of the object) and hold it there. Then begin again. Don’t give up or stop. Just take your time. It is important to make it clear by your actions that your male will be anally trained.
What if he just can’t accept the object? If you are convinced he just can’t do it, you have two choices: You can remove the object and give him a rest. Let him know you will resume the next day. He needs to know that the object will be up his ass sooner or later. The second alternative is to remove the object and insert a smaller one if you have it.
The key to anal training, or any training for that matter, is to always reach your goal. If you want to peg your male and he agreed that you should, then nothing should prevent you from reaching that goal. It may take time because he needs to learn to accept objects and then learn to handle the fucking motion. That’s fine. What isn’t fine is abandoning your plan. A key to caged male happiness that is frequently overlooked is that your male needs consistency and the sure knowledge that if you say that he will learn or do something, that nothing will stop that from happening. That doesn’t mean you need to be abusive by forcing painful objects up his ass. It means that you will do whatever it takes to eventually reach your goal.
Being caged puts the male in a dependent position. Just as with a child or pet, the caged male needs to know that if you say something will happen, then it will. This knowledge, whether he knows it or not, will bring comfort and contentment.
Not every couple will want to embark on anal play. I’m glad that Mrs. Lion is training me. Give it a try. You may like it too.