"The minute Henry brought home that motorcycle, Regina started enchanting it. It never crashes, it never breaks, it never runs out of gas. And if it's stolen, it reappears to him in less than twelve hours.
Henry: Can you make it fly like Hagrid's?
Regina: No Henry. Muggles would notice."
Mainly based upon The-Queen-Of-The-Merry-Men's headcannon with a few other's ideas thrown in and also based on season 7's spoilers so avoid if you don't want spoilers. I know a lot of people have done this already but I couldn't resist and this headcanon (and that tear-jerking bit added on) has been on my mind for a while now and I knew I just had to write it so I hope you don't mind and I hope I've done it justice. Enjoy :)
Spoilers for season 7.
She knew this day was coming. It was always there, in the back of her mind, even if she didn't always think about it, it was there.
She knew he wouldn't stay a little boy forever. Knew he wouldn't stay home forever.
It was time to leave the nest and fly. Something Regina had to come to terms with, even if she didn't like it.
He comes into her view as she reaches the gate. Sat upon the motorcycle that once belonged to August, his teeth biting his bottom lip as he adjusts the helmet, he looks more like a man now, more than he ever has and Regina guesses he is now.
"Hey, Mom." Henry says when he notices her. She gives him a sad smile, the lump in her throat allowing her to do nothing else.
Regina crosses her arms over herself, feeling the gloominess of the air around them, the way the world seems quiet, even just for this moment.
"You have everything?"
She tries to keep the sadness out of her voice, tries to sound happy and supportive. This is what Henry wants- he wanted to go to college, wanted to see the world outside of Storybrooke and he isn't going far, not really, it would be simple to come back and visit on weekends. That's what Regina has to hold on to, to hope that he does come back and see her, see everyone, again, that he doesn't just slip away from her like everyone else.
"I think so." Henry says. He has a backpack and perhaps another bag but that's all and Regina can't help but feel like it isn't enough. That, for the eighteen years he'd been alive for, he should have more to show for it, not just two bags.
Of course, he'd only taken what he needed so there are still things back in his room that, if collected together, could possibly fill up another bag but he hadn't wanted much luggage, he'd told her when she asked about the things still left on the shelves. It was right, practical, he had no need for that stuff anyway anymore.
"Good," Regina says, reaching forward and fixing the straps on his backpack- a habit or perhaps it's something to do, something to distract her from reality.
"Emma said you'd enchanted the bike." There's amusement to his tone. Of course she'd enchanted the bike. She hadn't liked it when she first saw it, wanted to kill Emma for bringing it out of Marco's shed and she'd almost told Henry that he was driving a car yet when Regina saw the look on Henry's face, she knew she had to let him have it, especially when he told her that it was the closest thing to a horse in this world. She'd laughed at that, remembering her own love for actual horses at eighteen and let it go. Yet she couldn't stand the thought of anything happening to him on the death trap and had sneaked down stairs when he was asleep, putting all sorts of enchantments on it much to Emma's amusement when she told her.
"Yeah," Regina says, nodding and beginning to list off all the spells she placed on it. "It won't crash, break, run out of gas, and if it's stolen, it will return to you in less than twelve hours." She made sure to cover all the basics.
"Wow," says Henry, smiling and looking down at the vehicle. "You really have it covered." Then the smile turns into a smirk and he looks at her, almost childishly, asking, "Can you make it fly like Hagrid's?"
Despite the sadness and memories (he'd once asked, when he was seven, if he could have a motorbike that could fly for his eighth birthday) Regina laughs and unlike the shocked Don't be silly, Henry answer she'd given him when he was seven, she instead replies with, "No, Henry. Muggles would notice."
The smirk turns back into a smile and a Of course they would and it breaks the moment for a bit before Regina knows that they're only avoiding the inevitable and that darkness is cast over them once more.
"You don't want me to go, do you?"
Regina looks down, running her hand up and down her arm and biting her lip. It's wrong and she should let him go, it's his choice and he wants this, yet she can't help but want the little boy who climbed into her bed at night because of a nightmare about a dragon.
He doesn't wait for her reply, he already knows the answer.
"I'll be back, Mom. I promise. I'll visit every weekend if I can."
She smiles, on the outside agreeing, but she knows on the inside that it's just a dream, just something to reassure her because soon, he'll have his own friends, his own life. Coming back home to a town built out of magic (that could possibly not even exist soon) will be the last thing on his mind.
It's getting late, Regina knows, and the last thing she wants is for Henry to be the reason he's caught in rush hour. She needs to let a grip, let him go and move on with his life but the words still feel traitorous as they leave her mouth.
"It's getting late," she says and Henry nods picking up his helmet. "You need to get going if you don't want to be caught in the traffic."
Henry nods, there's a sadness in his eyes and she stares at her for a while.
"Goodbye, Mom."
It's words she's only been scared of hearing once before, the first time Emma came to town and each day she wondered if Henry was going to say bye to her and live with Emma because she was a 'hero' and Regina was nothing more than a villain from some tale. How it was much more complicated than that, Regina thinks.
Still, she reaches forward and embraces him and he's fully receptive, wrapping his arms around her. Sitting down, Henry's shorter than her and Regina's able to press a kiss to the top of his head, leaning her cheek against it. For one last time.
He's the one to break it, whispering that he has to go now and Regina nods, letting him go. The helmet goes over his head, shielding his face from her (the first thing to disappear, she thinks) and his foot placed on the ledge as he starts the engine, kicking the stand away and driving off.
Regina watches him go, tears forming as he rides off down the road, towards the main part of town and finally, to the town line where Emma's waiting for him to wish him off. She wishes she could be there, knows how easily it would be just to poof to the town line and see him one last time, say goodbye one last time. But that isn't fair on Henry, he's feeling it as much as she is, standing outside the gate of the house she raised him in, knowing that he'll be okay.
Time for the bird to leave the nest and fly on its own.