It started with Maleficent. Rumpelstiltskin didn't mean to marry her. But they were beasties, shapeshifting freaks who were to be feared among men. They had no place to belong in the world they dominated. People hated and feared them. They were addicted to magic in their own ways. There was an understanding between them; it made sense at the time. Maleficent told him that he was free to marry anyone else that he wanted. She was open-minded like that. Just as long as she could as well. She had another husband tucked away somewhere. He didn't know who, or who the father of the baby was when she told him she was pregnant, but he knew it wasn't him. At least biologically. They'd talked about it at length and decided that he'd be the father of the child. Maleficent told him that the father was in no place to be any sort of father, and it would make no difference to Rumple whether it was a child by blood or not. Well, that was before the Charmings took it from them.
Cruella was next. They got drunk. It took a lot of liquor to inebriate the Dark One but Cruella somehow had a supply. And one night when Maleficent was seeing her other spouse (Spouses?) they decided to get drunk and somehow it seemed like a good idea to get married. He didn't know if he regretted it or not. It was very rare that they…indulged. But at least she always made sure he was immaculate…while insulting him as she did so. It was a weird sort of relationship. But he was pretty sure he loved her in their own little way.
Ursula WOULD have been next, they dated for a bit. Then she asked him how he felt about tentacles. He didn't feel anything good about tentacles. But apparently Cruella felt LOTS of things about tentacles. So that turned into something between the two.
Belle was after them. A spark of light in the ocean of darkness (and there was a lot of darkness in that castle.) He didn't mean to fall in love with the maid that was brought in to help clean up. But he did. Maleficent didn't mind her, Cruella was a lot harder to convince. Not because she loved him, she claimed, but because she didn't want to surrender her power as newest wife to a younger prettier thing. But before the curse, he finally convinced her, they were married. His first wife that preferred just him.
Then the curse came, the curse placed him with Regina for 28 years. For 28 years, Regina rebuffed his cursed advances; snarked at him in ways that confused him and finally talked him into adopted a son. A son named Henry. She named him after her father and that was weird, he thought her father's name was Larry. But she brought him back and he loved the boy like his own son. Then Emma came and he remembered, and Regina tried to poison her to get her out of the way. Henry got sacrificed. The curse got broken when Emma fought his first wife under the vault. But Emma didn't kill her, Rumpelstiltskin couldn't bear the thought that his first wife should get hurt from the curse. So instead he had something that would knock her out and extract the egg. The curse broke; he and Regina decided to make a go of it. They were both, that was the mantra. He believed if they were both, then the vows he believed he made should hold up. She stayed with him because he understood her and was one of the few people in town that didn't want to rip her to shreds. Plus doing so would break apart the only family that Henry ever knew until Emma came along. And on his visits, he'd be surrounded by three other stepmoms NOT her. Anyway, for Mr. Gold to have made vows to her, Regina supposed the cursed self that he thought she was made vows as well. And Regina never broke a vow. That was Snow's territory. Promises MAYBE. After all, there was a difference. Even if the memories weren't hers and were fake for him, she made a fake vow! Meanwhile Rumple just didn't choose to think about the time he spent with Cora and now her daughter. Just like Leopold! Their family tree was complicated enough. Wanting to make it work with the daughter of his lover who curse married him wasn't the creepiest thing he ever did….but it was sort of up there.
And then there came Emma. Honestly he didn't know what he was thinking when they eloped. She was Bae's love. His grandson/adopted son's mother. He supposed maybe that's why he did it. He married Emma; Henry could have his father and two mothers, and three stepmothers all in one household. He'd jokingly said they could make a deal when Emma was visiting. Emma jumped on board with it. Maybe she was drunk too and really good at hiding it. Maybe she secretly really liked older guys. He didn't know. Of all his wives, Emma was the one that didn't make much sense but he sort of went with it. Emma wasn't too dark, she wasn't too light, there was greyness to her that he found refreshing. He enjoyed her company.
So he had five wives in a six bedroom house. Even then that didn't feel like enough room. He wasn't sure the largest castle in the world was enough room.
And then one day, Belle got pregnant.
A/N: I don't even know, this was an idea I had at 7 in the morning, we'll see how it goes. There's enough crack, snark, and potential friendships and relationships in it to work in a weird sort of way, so I'm going to see where it goes.