A crude term for an individual with an alarmingly large number of STD/STIs or love bugs, regardless of whether they show signs of them or not.
Shit Monkey: "That whore of a man, Testicle Tim, has slept around so much that he's finally contracted every STD known to man."
Fuckhead Fred: "Hey, he be gots them 50 Shades of AIDS!"
Shit Monkey: "You fucking dumbass, there are way more VDs than AIDS."
Fuckhead Fred: "Hey, he be gots them 50 Shades of AIDS!"
Shit Monkey: "You fucking dumbass, there are way more VDs than AIDS."
by Testostices McSourpenis August 30, 2019

1; Performing advanced erotic (sometimes dangerous) sexual acts to Kayla-May.
2; to broaden Kayla-May's sexual horizon, and knowledge of her sexuality through the demanding instructions, and stern discipline of her "Master".
2; to broaden Kayla-May's sexual horizon, and knowledge of her sexuality through the demanding instructions, and stern discipline of her "Master".
"Man last night was lit af, she let me go 50 shades of May on her ass with some nylon rope, a bullwhip, and a gag ring!"
Kayla-May patiently waited for her Master to begin the days "50 shades of May" lesson.
Kayla-May patiently waited for her Master to begin the days "50 shades of May" lesson.
by Batsquirrel May 13, 2019

Derived from Ex-British Prime Minister, Theresa May. When a British prime minister enjoys the practice of BDSM.
50 Shades Of May extract:
"Before I know it, Donald's got both of my hands in his orange grip above my head, and he’s pinning me to the wheat field gate using his tiny hand … His other small hand grabs my short hair and yanks down, bringing my face up, and his crusty lips are on mine …"
"Before I know it, Donald's got both of my hands in his orange grip above my head, and he’s pinning me to the wheat field gate using his tiny hand … His other small hand grabs my short hair and yanks down, bringing my face up, and his crusty lips are on mine …"
by C L G March 24, 2020

*boy shoots a basketball and airballs*
"Damn bro you're 50 shades of ass right now! Sit on the bench!!"
"Damn bro you're 50 shades of ass right now! Sit on the bench!!"
by KurtBrusselsprouts December 13, 2015
