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1.
Ejaculation technique performed by an oject, usually finger, being inserted up the rectum and stroke the prostate gland. This is allegedly where the male G-spot resides.
Angela was milking my prostate last night. I came so hard that it smashed the light bulb!!! Then the dirty bitch sucked her fingers...... I haven't kissed her since.
by SpaccaDayNightFever July 26, 2003
 
2.
when and if a pregnant woman rubs her breasts upward/downward and inside the asscrack of her lover or sexual partner. (strait orientation)
and so she continued to satisfy me in bed with new sexual positions like milking the prostate with her tits up and down my ass
by cam-o flazsh July 02, 2011