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Penetrating the circle 

The act of being able to speak with the hot chick, if only for a fleeting moment, before her lame, fat, nasty friends that she came with realize you are there and launch a counter attack in order to get rid of you.
We wished Chris luck as he tried his hand at penetrating the circle. He stood in the shadows for some time, and just as 3 of the fat, nasty whore friends of the hot blonde broke off to swap clothes or change their tampons in the bathroom, he struck. He was able to have a conversation with the gorgeous woman for just under 30 seconds before another fat whore friend of hers, who was returning from the bar, saw what was happening and drug her away.
Penetrating the circle by Dasspam November 8, 2009
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deca-penetration  

Penetration by 10 similar objects at any given time simultaneously. See also decaphilia.
Dag yo! Did you hear Julie got deca-penetration ? She totally got annihilated by 10 garden hoses last night, shit was whack!

ur family vacation anal penetration

This is a very godly insult. No other insult can beat this.
Ted: ur mom gay
Timmy: ur dad lesbian
Ted: ur granny tranny
Timmy: ur grandpap a trap
The whole earth is shaking.
Ted: ur sister a mister
Timmy: ur brother a mother
Ted: ur niece obeser
Timmy: ur aunt a crossiant
Antarctica is the first continent to collapse and burn up.
Ted: ur uncle nick has no dick
Timmy: ur family tree LGBT
Ted: ur poo LGBTQ
Timmy: ur family reunion homosexual communion
All of the Earth except Timmy and Ted's homes have collapsed.
Ted: ur ancestors incestors
Timmy: ur genome gives gnome dome
Ted: ur god a fraud
Timmy: ur genus likes penis
Ted: ur social media penile encyclopedia
Timmy: ur family vacation anal penetration
Ted instantly dies and explodes into dust. All of the Earth except Ted returns back to normal.

Sexual penetration 

it's wot i did to ur mum last night
Sexual penetration by Shnief February 5, 2014

Penetration 

Sometimes in a homosexual relation ship the penis will penetrate the anus
"Was their Penetration?"
Penetration by DefDigital July 22, 2015

Penetrateables 

Anything that can be penetrated with a penis, including:

vaginas, ani (anuses), mouths, tightly closed armpits, squeezed together breasts, holes in the walls of public toilets, wounds, empty eye sockets, flesh lights, nostrils, ear holes, pushed together feet, warm pies, ripe fruit, bin bags, two-week old corpses, animal cages and sauce bottle with the lids removed.

It should be noted that most of these are not reccomended in any way, shape or form.
"That girl had more penetrateables than a two-week dead pirate."
Penetrateables by H.S. Willsy August 25, 2011

penetrated 

she got penetrated
penetrated by sparkly dragon February 25, 2015