Milking time... somehow!?

Hello all,

Me and my GF are newly experimenting with femdom and chastity and denial and all that, and we were wondering about using an aneros to milk. From what I've read though that might not be the best idea, so maybe we should do something else?

Part of the problem is that we haven't had a successful milking using any other techniques yet. I'm sure it's possible and maybe we're getting closer - sometimes I feel that "need to pee" sensation, but nothing more than a few drips ever come out, and it seems they only sort of work their way out when we're done and I stand up or bend over or otherwise push things through the tubes by happenstance.

Part of *that* problem might be that I really can't find my prostate, and never know when I'm massaging it except that I guess it correlates with "need to pee". Obviously I have one, but it's hard to feel for from the outside, and when I go inside and reach as far as I can - then I think I can find it, but it doesn't feel like a walnut at all and it's right at the tip of my fingers. Maybe I have short arms?

Anyway, basically I'm asking if anyone can help us work out how to do milking :/

Thanks!
O

Edit: The problem with an aneros is that it sounds like it might be too pleasurable (definitely not allowed - and also extremely painful if it results in an erection, since I'm now wearing one of these pretty much 24/7: http://www.clubfem.com/mcd1.htm ).