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pencil in a trashcan 

normal sized penis and a large stretched out vagina, or, a normal vagina and a itty-bitty penis interacting
hey bob, i banged melissa the other night! she was so loose, it was like putting a pencil in a trashcan

not the sharpest pencil in the drawer 

a clever euphamism for someone who lacks intelligence

see also a few bricks shy of a load, not the brightest bulb on the porch
Seth - "Did you hear about Werner? He tried to start his car with lighter fluid."

Taylor - "I'm not surprised; he's not the sharpest pencil in the drawer."

Sharpest Pencil in the Pack 

A lazy person; a pencil that is still sharp has obviously not been used, and is therefore not doing a lot of work. It also sounds like a compliment, so you can troll people with it.
Why are you here? You really are the sharpest pencil in the pack, aren't you?

I'll pencil you in 

This is what a person says when he is making a tentative appointment.

"I'll Pencil" (because the appointment can be erased) "you in" (to my schedule book).
Ozzy: Hey, can I come up to your big fancy office and make fun of you?
Boohiss: Er. I'm kinda busy this week. Tell you what, I'll pencil you in for 4:30 on Thursday.
I'll pencil you in by boohiss May 20, 2004
Word of the Day on April 26, 2008

lead in pencil 

it is said of people of little strength, character or resolve. also said about men who can't get an erection during sex.
I slept with Roger last night. He couldn't get it up. he's got no lead in pencil (or no lead in his pencil).
lead in pencil by Yoova September 17, 2006

i'll lightly pencil you in 

To pencil someone into a schedule but using a light amount of pressure. This way, as you know they will always cancel, when you erase, there is no visual indent of their name in your schedule.
Guy: sorry I keep cancelling on you, would you like to go to the cinema on Friday?

Girl: yes, I'll lightly pencil you in.
Guy cancels
Girl to friend: I am glad I only lightly penciled him in, as there is no indent to remind me that he cancelled AGAIN!