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1.
The act of manipulating the prostate gland through the anus, so as to discharge as much seminal fluid as possible. Often used in BSDM circles.
Bob: Hey Steve, have fun with Cindy last night?
Steve: It was ungodly. She gave me the milking of a lifetime and I blew my load five times!
by Xenoce May 27, 2005
 
2.
when someone jerks off/ fucks a guy until every drop of cum comes out
He begged her to keep milking him because he loved how it felt.
by Dawn June 15, 2002
 
3.
1) To squeeze a cow's udders to collect milk.
2) A sexual term: to force a man to ejaculate repeatedly.
1) The farmer said, "Go and milk the cow.
2) She tied him up and milked his cock.
by Homer S. February 13, 2005
 
4.
When a man gets on all fours and the partner goes behind him reaches underneath and pulls the erect penis, into the position that his penis can be milked, such as a cow would be.
Did you hear when Jim was eating out Mary, Nancy was milking him!??

James brought a partner over last man, and he was milking me man.
by ninjawarriordex2 September 10, 2007
 
5.
A term used in West Sussex, South East England for taking bottles of milk from a moving milk float or stealing milk from doorsteps. This practice is usually performed by thirsty chavs who can run surprisingly fast.
Me and Phil went milking this morning, but we didn't get anything.
by AlexaJoy May 23, 2011
 
6.
When a man sticks his penis down a woman's throat and the woman then proceeds to do the swallowing action while the penis is still in the throat. this tightens and loosens the muscles around the penis in a downward motion like they are "milking" it.
The way you were milking my penis last night was awesome!
by penismilker April 13, 2009
 
7.
When a bong is being used to smoke or marijuana, when the tube of the bong is being filled with smoke it begins to milk. So therefore while the bong is ebing filled with smoke it is milking.
"Yo Jack don't hit that yet it is still milking"
by DG April 10, 2005