You've been sent down. You're going to go grey in chokey, you're doing 5 to 10 in the Pen. They've got your number, bang to rights. You've been sentenced to some time in prison, is probably the main point that I am trying to make right now.
As well as whatever it is that you're allowed to take with you, you can also have anything that you can keep up your ass for 30 seconds without shitting it out when made to squat. What would you try and get in through the back door, so to speak?
I'll go first, it's only fair - my iPod and charger. And if there is any room left then Cluedo, obvs

vials of pure thc
A machine gun
You have serious rectum space.
a bottle of poppers
justifies itself
the keys
A laptop and FM2008
i don't even want to think about the size of your arse
if you can fit that up it
I would hope
my arse wasn't a general thought topic for you in any case.
Oooh!
You can share my cell, I've got Cluedo
Note to self -
if going to prison, don't ever excitedly exclaim 'Oooh!'
Aces!
I'll be Pompey, you can be Saints. South Coast war.
i downloaded cm97-98 recently
it rocks. i just won Euro 2012 with Italy
Where did you download it?
cant remember
just googled about the place for a bit and got it thru some torrent. utorrent maybe?
I second the iPod and charger
they'd find me swinging from the ceiling the first night otherwise.
Better shove
a rope up your arse in that case.
portable
yahtzee
A bloody massive fist
for fighting, and for scaring all the butch girls off.
that'd fit up there nicely ey..
well i havnt seen any suggestions better than mine so far
Cluedo?
Wimp. I'm taking monopoly. Go big or go home.