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Woodstock Dick 

A Woodstock Dick is when you look like you attend the woodstock festival and you take a lot of speedy drugs and you have a huge bush of public hair. Your clothes become a burden so you get naked and walk around with your mushroom cap sticking out of the bushes as seen at the woodstock festival I'm archival photos.
Random hippy chick: Hey peace man you're really groovy . It takes a lot of guts to be naked in public when you have a Woodstock Dick
Woodstock Dick by moman86 September 30, 2016

tattered windsock 

To render one's anus or vagina in a graphical state of distress, as a result of a particularly violent bowel movement or penetrative intercourse.
The description comes from the similar appearance to the ripped edges of a windsock (an item of metrological equipment used to establish wind speed/direction) as used at airports/flying schools, etc., which have become tattered as a result of excessive weather conditions.
"God, that curry last night was awesome - my arse puckered starrusty sheriff's badgechocolate tea towel holder this morning was like a tattered windsock"

"He was hung like a horse; my twat vadgegrowleryeti's welly looked like a tattered windsock afterwards"

woodstock skank 

dirty, stinky, indie chick that (1)wears all natural clothes and perfume, (2)sleeps with every member of the band, (3)is "too cool" to work, but constantly complains about not having money (refuses to be "corporate slave"), (4) holds useless liberal arts degree(s); most likely encountered at open-air music festival, occupy xyz protest, posh cafés, abstract art museums, parks, wherever there is free food/drinks provided
This woodstock skank hasn't showered in three weeks.

She is a real woodstock skank down there.

Look at that woodstock skank. She has an entire bird nest in her hair.

Woodstock 

one of the biggest friggin concerts ever. over a million hippies all in the same place. probably the biggest pot cloud ever. you could walk into the crowd sober, wearing a t-shirt, shorts, and sneakers and come out red-eyed stoned, wearing a poncho, beads/peace sign necklace, bell bottoms, and sandals. and jimi hendrix played there, too.
"Woodstock's the name of a bird in the Peanuts comics, too"
Woodstock by Tommy F. September 22, 2005

Woodstock High School 

A school which was unfortunately opened in 1996 and has possibly the highest number of sexual violations (many involving staff) in the Metro Atlanta area. From coaches banging cheerleaders to various forms of sexual harassment from the teachers, to girls sending pictures of their tits to their boyfriends (which then seem to somehow spread around the entire school), it's safe to say that Woodstock High School is a walking STD.
Typical conversation at Woodstock High School-

Guy 1- "Dude, did you see Victoria's tits?"

Guy 2- "Psh, that pair spread around two weeks ago... I got Shayli's on my phone now"

Woodstock, Illinois 

Woodstock Illinois is a small town located in the far northwest of Chicago. It’s hightlight is their town square where Grounghog Day was filmed in the 90s. The town is a Mecca for illegal immigrants, wannabe gangsters, hippies, homeless, and drug abusers. The older residents, who’ve never left town, wonder how this quaint little town has gone to shit over the years. On weekends, the “downtown” bar whores run aloof; they’re diseased so beware of them. There are multiple Mexican restaurants.. hardly anything else. If you’re looking for a good taco, some cocaine, or an easy chick to take home just hop on the Metra train from Olgilvie Station and have them drop you off at the second to last stop from the end of the line.
Where are you from?

I’m from Woodstock, ILLINOIS.
Is that near Chicago?
Yes (easier than explaining it is nowhere)