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If male milking is of interest to you then you might want to take a look at this old discussion of prostate manipulation:
For my Mistress/wife, Ms Nancy, and I, itís a very erotic experience. We take it verrryyy slowwwwwly. We make sure we are both in comfortable positions with lots of pillows. We also put on some relaxing new age music and light some candles. For us, this is a special occasion, rather than something we have to do. We are both naked. Iím on my hands and knees, my head on the floor with pillows under my head and chest. Ms Nancy sits or kneels behind me. We set a couple of mirrors on the floor so that we can maintain eye contact the entire time.