He'd become a streak of light. His path ended at a young woman. She was already expecting, but it was early enough, and there was still room...
Nine months later, the Winchesters proudly brought home a set of twins. One named for Mary's father, and the other named for John's father Lucas.
Six months later, as Azazel bled into the mouth of the older twin Samuel, he found himself looking at the younger twin and frowning at the oddly familiar feeling the child was giving off.
It couldn't be.
Mary interrupted him before he could bleed into the mouth of the younger twin.
In the Pit, Lucifer halfheartedly picked at a weak point on one of the seals as he had done for the millennium that was the decade since Azazel had come and weakened it. He would be getting out in a couple of measly decades if Azazel did his job properly, but still, it was something to do...
Dean did his best to remain silent as he broke into the two bedroom apartment that the younger Winchesters had pooled their resources for. He had almost been at the fridge and the beer it contained when he had been attacked by Gigantor 1 and Gigantor 2.
Sammy, and Lucas - the rather handsome twin who was nearly as blonde as their mother had been, but couldn't be mistaken as anyone other than their father's child despite the obnoxious curls that he was constantly wasting money to straighten - had him pinned in under three seconds. Despite running off to Stanford to become lawyers or something, they apparently hadn't been neglecting their training.
As the three brothers were roughhousing on the floor, a blonde woman in a smurf shirt and undies came out of one room and a pair of naked brunette twins wrapped in a sheet and blanket respectively out of the other.
"Um, Jess..." Sam said, apparently trying to come up with an explanation for what was going on.
"Sarah, Sandra, I want you to meet our older brother Dean." Lucas said as he let Dean up.
Nearly Four Years Later:
Sam, Dean, and Lucas shielded their eyes from the bright light as one bright flash after another escaped from the Pit. A moment later, they opened their eyes to find themselves aboard an airplane. Once they landed, they stole a car and drove to Chuck's house to find Castiel.
Lucas had never personally met Castiel as he had spent the last year in physical therapy after Lilith had nearly killed him, and had only just gotten back into something approximating hunting shape. He was looking forward to doing so. Unfortunately, Castiel was a red smear on Chuck's wall by the time they had gotten there.
Eventually, events led to the three brothers finding their way to their father's storage locker. Zachariah was waiting for them. Zachariah gave his speech about Dean being Michael's vessel, and when Dean refused to say yes, he started torturing Sam. He turned to torture Lucas only to find himself falling backwards on his ass, in open-mouthed shock.
It was as he was beginning to recover that Castiel appeared, apparently back from the dead. Oddly enough, the first question that came out of Zachariah's vessel's mouth had nothing to do with this.
"I-If Lucifer's right there..." he started, pointing at Lucas. "Who got freed from the pit?"
Elsewhere:
"STRIPPERS!"
"GABRIEL, YOU'RE THE BEST BROTHER EVER!"
Back at the storage locker:
"The Grigori." Castiel replied.
"Son of a bitch." Zachariah said.