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1.
Derived from a situation in which you are cock blocked by an asshole friend. While he is fucking the girl he stole from you, steal his shoes and jerk off on his insoles.
Man, that dick head cock blocked me again!
what'd you do?
I gave him the doctor scholl's!
whats that?
I jizzed all over the inside of his shoes!
I bet he's gellin now!
de MC Barlow 17 mars 2008
 
2.
When, after engaging in intercourse with a woman, one, unbeknownst to the woman, ejaculates into her shoes.
The Doctor Scholl's is self-explanatory.
de Bennington 9 août 2010