Disclaimer: I do not own the characters and I am not affiliated in any way, shape or form with anyone who does.
Sitting on the beach, Desmond remembered standing up in front of his class as a child; all of them having to declare what they wanted to be when they became adults. Quite a few were firemen, some were doctors and a couple wanted to be sweet shop owners so that they had access to candy when their parents weren't looking, but Desmond had a different answer entirely.
"I'm going to be a pirate."
There had been giggles going around the classroom, including those of his teacher; "Desmond, pirates don't really exist."
"Yes they do!"
Then his classmates had joined in, "don't be stupid! You're not a pirate!"
"Yes I am!"
"Not not not!"
"You just wait… I'll be a pirate someday."
He had held onto his dream for a few years before he had decided that they had all been right; he had to pick a career that meant something. He'd half fallen and half been pressured into joining the army but it hadn't worked out. He just wasn't capable of following the idiotic commanders and it cost him his freedom.
The nights he spent lying in jail he wondered what had happened to himself as a child, wondering what had happened to those carefree dreams of sailing the high seas looking for treasure and women and experiencing the freedom. Well, as a kid he'd only been interested in the treasure and the freedom but as an adult he wouldn't say no to the women.
Then he was free, and he wanted to find a way to get revenge for losing Penny and the idea had seemed so simple, he would win the race and win the girl…
And he'd get to play pirate while he was at it.
But it had ended up harder than he thought it would be. Being battered by the waves felt like too much for him to handle, and he had been sure that this was the end of him. Until he woke up, and was dragged down into a hatch that tantalized him before consuming him with feelings of anger and hatred once he realised that Kelvin had done nothing more than lock him inside another jail.
The first chance he had, he'd run back to his ship. Back to the desire for freedom. But there was none to be had, he'd ended up going in circles, and slowly decided that he wouldn't be able to get back to Penny, or the real world. Then he'd done the final thing he considered pirates to do, he'd opened up a drink.
So now he was back on the beach, feeling sorry for himself, downing as much alcohol as he could stomach and through the haze it almost felt like he had finally become a real pirate.