A/N: If you are following my prompt stories, Danny's 712 Additional Things To Rant About, you'll know that there was one prompt so far that has inspired a full chaptered story, this is that tale.
Chapter 1: Family Vacation
"I hate flying. I hate flying. I hate flying," Dean Winchester mumbled to himself as he and his brother stood in line to check their baggage and sign into their flight.
"You know what, this will be good for us. We gotta just get away from the men of letters for a while and let them wear themselves out over a continent that's way too big for their eradication plans," Sam said as he leaned in and whispered in his brother's ear.
"Sure, but I have to leave my baby behind. I have to leave my arsenal behind. I have to fly over water for seven hours. How are we supposed to hunt in Hawaii?" Dean grumbled in retort.
"We have connection over there, calm down, they are prepared to help us out if we need them," Sam tried to reassure his brother as quietly as he could but he knew damn well he was failing and Dean just needed to get it out or the anxiety of flying would be too much.
"And why do you have to hunt?" Mary Winchester asked as she spun around on her boys. "Maybe we just go and work on our relationship. Maybe we have our first ever family vacation. Maybe we learn about a new culture and people and not worry about our problems here. Maybe, heaven forbid, we act normal for once and relax," she said with conviction and desperation.
"You just wanna lie on a beach, don't you mom?" Sam asked and winked.
"I've always dreamed of Hawaii," Mary confessed. "Ever since I saw Blue Hawaii as a girl."
"And that's the only reason I'm doing this," Dean said and his anxiety showed through his stoic exterior.
"Big bad Dean is afraid of flying," Sam said as they inched closer to the check in counter.
"Honey, is this true?" Mary asked with concern.
"Yeah Ma, I do not like flying at all," Dean answered. "Give me twice as long in my car or torture at the hands of demons, I can handle it, but flying, flying is worse than the apocalypse."
"Everyone needs at least one crippling phobia," Sam said in tones of teasing but knew very well his brother's struggle.
"I'm sorry you feel that way," Mary said just as the line opened up to lead them to the counter. "But suck it up, we're going."
"Don't worry mom, I brought some over the counter sedatives. We'll get him settled and then knock him out," Sam said as he stepped around his brother and lifted her suitcase onto the scale for her.
"As soon as we're through security I'm getting drunk," Dean mumbled as he moved forward.
"Whatever it takes dear, whatever it takes to get you on that plane," Mary said happily and handed the tickets to the man at the counter.