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It's entirely possible that self-administering anal stimulation may help you know how it will feel for him, even though each person's experience differs. However, providing anal sexual actions to yourself and to another person are quite different things, in terms of position, where you can reach and what you can do.

If you don't enjoy anal stimulation, it might not be a great idea to "train" yourself. It's something that one has to gradually and willingly start doing. However, it does not mean that you and your boyfriend can't experiment just on him. There are plenty of people who provide anal stimulation who have never felt it for themselves, or simply didn't like it. As he is an individual, it is best for you two to explore together, slowly. It can be an immense bonding experience and you will both learn a lot together.

As for what you can do, there are numerous guides on the Internet. I don't recommend going straight for full-blown prostate massage immediately, though you likely already know that. Instead, try some external stimulation by itself at first. While it may not be widely considered as having the same pleasure potential as the prostate, external anal stimulation can be immensely satisfying. Start with that, keep it slow and sensual, and explore your feelings on the matter. It's especially good to start with something not explicitly sexual at first, like a body massage.

Simply proceed with what feels good, and communicate throughout the whole process. I'm not sure how much of this advice will be helpful, but I hope it clarifies things a little for you.

I would think open and honest communication would be the best bet. The sensation isn't going to be the same for you that it will be for him. Take your time and go slowly. Use lots of lubricant and ask questions. Does this feel okay? Do you like this? You could even have him show you. Let him start off and watch the movements and the way he responds to them.

Communication is key, and so is taking your time and using lots of lube!

Although there are differences in the male and female anatomy in this area - I fully support your concept. My self anal play helped me understand the pains and pleasures of this activity. Learning to lubricate - when to re-apply lube, how to pause after penetration to allow for adjustment, how to thrust in a pleasurable way - and how to gradually increase size.

For what it's worth our play goes from 1 finger to 2, then a small toy or plug - followed by the toy that will be used to bring about orgasm.

Good luck and enjoy.

If you 2 can communicate effectively, and read his body language you wouldn't need to practice on yourself. But I think you would have a better sense of anticipation as to what you should do if you practice on yourself.