A woman seeks to learn the basics of male prostate massage:
The main thing you need to remember is lubrication, lubrication,
lubrication. Use a good lube, try to stay away from KY and other water-based
lubes (unless you’re using a condem) they tend to break down quickly. Have
him (or tie him) on his back, go slowly, there are 2 sets of sphincter
muscles you have to get past. If you hurry the process you can really hurt
him (btdt, not fun for 2 days). If it’s his first time start with just
touching around the area. As for massaging his prostate, crook your finger
up slightly, like your pointing at his belly button and rub. My Master
highly appreciates this as it’s not something I’m really comfortable doing,
but do for him.
And:
I also like to use a glove just in case the fingernail isn’t filed
perfectly (yes, I am paranoid about causing unintended pain).I’ve used several lubricants and they all seemed to work just fine.
I don’t put a whole lot on my finger at first, I keep the container
there and add more as I feel it is needed.For the actual penetration, what works best with some men is gentle
but steady pressure inwards. Other men do better with intermittantly
applying pressure and releasing it by withdrawing. I think you just
have to experiment and find out what works with the individual involved.