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I milk my husband and he enjoys it. I locked him up for a year and all he got was milkings. I read a lot about prostate massages, watched whatever videos I could find and began to practice. First, yes, you need to trim your nails. The prostate is very sensitive and the skin extremely thin. Second, take your time and don't use too much force. Milking | Wife Wants to Play - Cuckold Forum - Amateur Please note: You are currently browsing img prostate milking sissy chastity caption datawav that is 684x719px in size. This image is listed in cuckold milking category. Milking Wife Wants to Play Cuckold Forum Amateur, 684x719 in 78.50 KB.