Milfmaid 

A MILF at a swimming pool. Often spotted wading in the shallow end with offspring.

Dude, throw me my goggles, there's a whole school of Milfmaids over there.

Milfmaid by sweet_thang July 6, 2016

Dirty Milkmaid 

A man kneels on his hands and knees, pushing his penis and testicles between his legs. All the while, his sexual counterpart kneels behind him, performs analingus and masturbates the tucked, downward-pointing penis. The masturbatory act looks similar to that of a milkmaid milking a cow's udders.

This act differs from that of a Rusty Trombone, in that the masturbatory act of the Rusty Trombone is a "reach-around" with a back-and-forth jerking motion with the pleasure-getter remaining standing; a Dirty Milkmaid's participant is kneeling and the hand manipulation is between the legs, using an up/down motion.

You might as well call me Bessie the Cow, because that filthy whore gave me a Dirty Milkmaid.

While I knew she could play a skin-flute, I had no idea she was also a Dirty Milkmaid.

That girl must work on a farm, because not only did she she tounge-dive my dirt-pipe, but she gave me a Dirty Milkmaid.

Dirty Milkmaid by West Coast Buckeye December 25, 2011

Milkmaid 

A woman who performs oral sex on a man or men, particularly on an ongoing or regular basis, where the oral sex is the primary dimension to the relationship.

John: "Man, I need a milkmaid who can drain my balls a couple of times a week."
Randy: "Why not place an ad on Craigslist for that?"

Milkmaid by Been There, Done That October 18, 2012

Milkmaid Express 

A quick, downward yanking hand job performed by a female. The male leans face first against a wall at a 45 degree angle allowing the penis and ballsack to dangle freely from the fly like an engorged udder. The female, while kneeling, squatting or seated on a small stool vigorously yanks and pulls on the man bits like she’s milking a cow until a rope of nut is milked to completion.

My manager gave me a milkmaid Express in the stockroom last night after close.

Rachel pulled up the ottoman and the next thing I know I was getting the milkmaid express.

Milkmaid Express by Eaton Holgoode January 23, 2018

Swiss Milkmaid 

When two guys are sucking on a lady's nipples while jacking themselves off.

So these freshmen guys were giving me a swiss milkmaid last weekend!

Swiss Milkmaid by amzwarrior288 December 14, 2012

milkmaid 

When a female sucks her own breast(s)

Hey check out Jane in the corner, she's milkmaiding - this ain't no party foul!

milkmaid by pidgey January 4, 2005

milkmaid 

a woman with a extremely curvy figure

Damn baby, you have got to be a milkmaid with those kind of curves!

milkmaid by Peru April 30, 2005