Tom Hiddleston one shot/drabble collection

What if Oakley had said yes?

Summary: Anna invites Oakley to stay the night with her. She knows she would be cheating on her husband, but she wants to enjoy herself while she's on holiday, even if that includes rolling around with her best friend's son. At first he is nervous about saying yes, but he accepts her hand and is led into her room. Although, once inside she worries that he's going to run out on her, but to her relief he stays.

Warnings: smut, oral sex, vaginal sex, fingering, cheating wife, mentions of skinny-dipping, swearing, rough sex and age difference - all of age

—————————–

"You can come in, if you want." Anna said with a hint of eagerness and a sparkle in her eyes.

Oakley stood there a moment looking sheepishly at the older woman. Their constant back and forth flirting, and side glances have come down to this, her inviting him into her quarters for the night. He knew that he was of age, an adult and she clearly liked him. His younger age made her feel younger, but he was intelligent when he wanted to be and asked a lot of questions, sometimes too many. He even thought that he over stepped the mark when asking too many questions, especially when they were about her and her husband Alex's sex life. More importantly when he asked about why they didn't have any kids of their own. Despite that though she still liked him and Anna seemed to enjoy his boyish charms, as well as his misspent youth ways. So much so it seemed, as she dabbled with smoking pot, went skinny dipping and she covered for the 'youngs.' Covered for them when the borrowed old banger of a car had been towed away. She went along with his story about a maniacal issue (an oil leak), instead of his cousin Badge's reckless driving around in a field, and ultimately ending up in a ditch. He allowed her to drive when she didn't even have a licence, as well as next to no experience with driving in the first place. Clearly he was a bad influence on Anna, yet she craved it. She craved him. Although at the start he kind of pitied her, because his own Dad's cousin Verena told embarrassing stories about Anna, and made jokes about her best friend. Jokes about how she was a goody two shoes back in the day, and no one ever really invited Anna to anything. Even after a few days he realised she didn't really fit in with the 'olds.' Also he knew without him the rest of the 'youngs' wouldn't have accepted her into their little circle. She was after all one of the 'olds' herself. The others probably thought that she was trying to weasel her way into the dynamic of the group. An outsider, as she's the only one who isn't a related member of the family on the holiday. He knew Alex was meant to come with her, albeit according to her story upon arrival he has prior work commitments. He doesn't believe her. Especially since he's spent so much time with her, and her answers about how rocky her marriage is and the lack of a sex life, only add up the odds against her.

Oakley and Anna bounded well together, but they also tried to hide their mutual growing feelings. Although even to the untrained eye it wasn't difficult to see what was going on between the two, except for the other 'olds,' who were completely and utterly oblivious to Anna's troubles. Never mind her attraction towards Oakley nor his towards her.

"I-I er...I mean if you want me to." Oakley replied shyly, with an innocent expression and rosy cheeks.

Anna held out her hand to him with a smile. Oakley wiped his sweaty palm on his shorts, before accepting Anna's hand. As she began leading him in he glanced over his shoulder to check if anyone was watching. He couldn't see anyone, luckily. Once inside she closed the door behind them and left Oakley standing nervously by it, as she headed further into the room and switched on the bedside lamp. Oakley had passed her room many times, but he'd never stepped foot inside before, it was almost as if he'd crossed an invisible line of sorts. An invisible line of no return, although deep down he'd been wanting to cross it since getting to know Anna. She was different compared to the other 'olds,' she was fun and easier to talk to for instance. She didn't treat him like a child either. Also she wasn't a child either, she was all woman and more mature. He liked that aspect a lot.