Give him a safe word and start testing things out ;)
if he's really a masochist then marry him. he will be the happiest man in the world.
Try maxing out his credit card shopping for gifts for other men. He should enjoy that.
yup. Asking him is best because all masochists like different things. Some prefer mental or emotional sadism while others prefer physical abuse.
You are TOO young to be dating someone who is masochistic.
Not really. I knew from a _very_ young age that I enjoyed being treated roughly. Who's to say that her beau isn't another bird of the same feather?
My boyfriend is a masochist as well. Since we aren't actually married, I feel it's best to keep things easy and simple, and things that are easy to hide. Generally I just tie him up in different ways. It's simple, there are plenty of reasons to have rope, and if you're caught in the act, say you were just practicing in case someone ties you up or self defense. If you want to take more of a part in it, tickle him while he's tied up. Just don't tie too too tight so he still has blood circulation.