Failed in some computer-related crime at a bank and got sentenced to a couple years in a really really low-security prison of some kind. It was more like I was going to camp than prison; K. drops me off, I have two bags of clothing and stuff (CD player, etc.), she walks me up to the lobby, and a guard just shows me to my room-- no cuffs, no searching me, nothing, but I was unsurprised in the dream. My room is this big, comfy room with hardwood floors and a big window (it did have bars, at least) which had a nice view of the bank and the trucks pulling up to drop huge bags of money off at it. My counselor comes in and brings in my two roommates, a couple of women whose names I don't recall (I think one was Bess)-- they weren't their real names. I was to use the name "Kelly". The fake names were so that none of us would know who other prisoners had been in the outside world-- we were all high-profile media criminals and they didn't want us mixing or something.
So we toured the prison facility and Bess (I think; she was really short) told me they liked me but I wasn't wearing any underwear, and I was having a hard time convincing her that I was and I knew it, but then there was this huge sound of screaming and destruction somewhere across the facility. So the four of us start calmly walking in that direction, past lots of rooms with open/ajar doors (nothing was locked in this place) and through a gym full of junior-high age kids playing basketball. Then I woke up, without ever finding out what the destructive sound was.