The most important thing is to find someone who ENJOYS doing prostate massage. They will usually initiate some teasing there to let you know or to see if you are interested so let the poor girl know if you are (ie. spread those cheeks, raise that bottom, use a pointer, draw a map with directions, stick a post it note there with an arrow! LOL) And please, before anything, go through the appropriate actions to assure her that you are not LE.
Prostate massage takes a certain amount of knowledge, talent and caring...too rough and the very delicate tissue there can be irritated or even torn. (YOU DON'T WANT THAT...unless you're into S&m ;o) Too light and you're deprived of some great stimulation that makes it so popular. Your therapist also needs to know where 'the hot spot' is and that is purely by feel.
It's a matter of trial and error finding a therapist who provides you with what you desire because they can't openly admit to what they do. Hopefully someone will steer you in the right direction.
If you are willing to go to Las Vegas you will find a lady who is great at prostate massage's. CindySpice. She has given me experinces I never dreamed of.
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