Diddler on the roof

In prison, it is the inmate who sleeps above the person which they rape.

"You got bunked up with Steve? That is not the diddler on the roof that you want to have."

by zaztastic September 01, 2013

Diddler On The Roof

When a man with a small penis cannot satisfy his partner and chooses to strap on a dildo underneath his penis while penetrating his partner with the strap on he uses his small penis to diddle her clitoris.

I couldn't get Ramona off last night so I had to strap it on and give her the diddler on the roof.

by Icepen15 April 06, 2011