Headcannon: Hugh and Fiona
Hugh and Fiona had a lot of sex on Cairnholm. They were very careful to keep this from Miss Peregrine; if she found out, at best they'd get a whooping and lots of privileges taken away, and at worse, she'd permanently send them to separate loops in different centuries and countries. Still, they went at it like rabbits.
They almost got caught four times; the first was sometime in the sixties when they first started, Horace had seen it in a dream (and was horrified), and Hugh and Fiona had to bribe him by giving him their desserts and doing his chores for two whole years so he wouldn't tell.
The second was still in the sixties, and they were doing it in the middle of the woods where they were sure so one would see them. But nearby Olive was playing ball with some of the other children and the ball bounced really far into the woods. Olive went to look for it, and saw them. She screamed and was crying for an hour after that. Hugh and Fiona got their clothes back on in the three seconds it took for Miss Peregrine to come see what was wrong. Neither of them could ever fathom how they'd gotten away with it that time, and they never brought it up.
The third time, it was the eighties and everyone was outside except the two of them (or so they thought) so they locked themselves in Hugh's room and took their clothes off. The closet door suddenly opened just as Fiona was straddling Hugh; Millard had been reading a horror book in the closet the whole time. Luckily, he was real chill about it; "you'd be surprised what I've seen in my life." was all he said, then he walked out, and he never told anyone.
The fourth and final time was during the first few weeks Jacob was there (you know, the time everything was perfect). They were in an empty house in the village so that no one would bother them. Unfortunately, they had no idea that the other children were playing hide-and-seek. Emma decided to hide in the house Hugh and Fiona were fucking in, and she was mortified as well as disgusted. She scolded them until the moment the seeker found her. Hugh and Fiona thought they were screwed that time, but they begged her anyway to not tell. Luckily, she didn't tell.
(Sorry bout that, guys; I don't know what goes on in my head sometimes.)
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