How do you even get to the prison? Really annoying running back and forth looking for scenes because devs love sandbox. A lot of the content is quite good other than that.
It's a little complicated to get there, you'll need to be arrested for not using a penis cage and you'll need to have a low relationship with Rayne so she doesn't pick you up at the police station.
what I did was:
first lower the relationship with Rayne to about half the bar
then ask Rayne to take off the penis cage, when she is at home on the computer
then go to the club and ask the dancer for a service and pay for the second service too you will need 500 credits
and when she asks you for a kiss you run away, at that point you are arrested