How many times have I thought I've gotten out? Only three, before now. I suppose they keep these illusions few and far between because otherwise I would just learn to expect it. I'll give them one thing; they're clever. They never start the dreams in the same way.
The first time was possibly the worst, because I actually believed it. I hadn't been in Hell very long, and I was still fighting their system. Testing them. Taunting them. That sort of thing. So when I spat out an answer to one of their little games, and they told me I was correct and I could leave, well, I was surprised. But the dream felt so real. I was dropped in a forest somewhere, and then Castiel was there. He told me that I was safe now. I believed him. I was happy for two weeks in that dream. But what made it realistic was that it wasn't perfect. I would have nightmares when I slept. I didn't have my grace. There were no moments that were skipped; time passed in a not-dream kind of way.
But then one time, the nightmare wouldn't stop. I tried to wake up, but it didn't work. I screamed for Cas, knowing he would come and wake me if he heard me. But he never came, and that's when I knew I was wrong. I had never left. I wasn't asleep; I had only woken up. It was just a new kind of torture.
The second time was very different. I didn't win a game to get out. I was rescued by Castiel and Sam and Dean Winchester. "We defeated Lucifer," they said. "He told us that he had you down here. Come on, we're here to save you." It was really believable, too, when they explained. They had thought out their story really well. But in the end, just before we should have reached the surface, the three people who were supposedly helping me morphed into demons. They dragged me back down. They were laughing. I wasn't.
It was a long time before the next "escape dream". I was pretty far gone, very close to being broken. And this cut the last string I was clinging to: snapped it right in half. They started the dream right in the middle of me getting ripped into shreds. It started similarly to the first one. I appeared somewhere not in Hell, only this time I was screaming. Then the pain disappeared. Someone was shouting at me to wake up. The memories of Hell started to fade away, and suddenly I was young again. Like, really young. Only a couple thousand years old, and my favorite older brother was standing over me. "Are you okay, Gabriel? I think you were having a nightmare."
"Yeah, Luci, I'm okay. Thanks for waking me. I don't know what I was dreaming about, but thanks."
"It must have been pretty bad."
"Don't worry about it."
"Okay. Come on, we could go and fly to a star! Maybe it'll sing to us again."
Yeah, so that was my childhood. And right then, I couldn't remember anything from either the 'dream' I had just 'woken' from or, well, the rest of my life. I really was just a kid again. And I spent ages there. I never had another nightmare in this dream. I was just…okay. There was absolutely nothing to suggest it wasn't real, because I had no reason to be suspicious.
Until I woke up back in Hell and remembered everything and knew that it had all been false. I'll admit it, I snapped. I broke. I swore I would never fall for another one again. I suppose that was their way of ensuring that even if I ever really did get out, they would still be tormenting me for the rest of my life.
Well, look-y at that. It worked.