Chapter Text
Dean could best describe his mood as...trepidatious.
Jess was a whirlwind of excitement and planning, as they made their way downtown.
When they arrived at the men's clothing store, Jess entered, beaming, with the terrified Winchesters in tow. Dean gave Sam a dark look, and they both braced themselves for the oncoming storm of try-on-a-thon that lay ahead of them.
“What can I help you with today?” an older gentleman with white hair and a gold pinky ring stepped over to help them. Sam smiled weakly at the man, and Dean tried not to think about how much this trip was going to cost him.
“These handsome men need suits for a wedding,” Jess smiled as she took Sam's hand. The man from the store looked from Jess to Sam, smiling at the happy couple.
“Congratulations!” His smile was warm and genuine this time around. “When is your big day?”
“Not theirs!” Dean burst in – he wasn't old enough to even START thinking about Sam getting married. “Mine.” Dean stepped forward, glaring at Sam, as if to say 'don't get any ideas', “I'm the one getting married. In June. Outside.” The salesman turned his gaze to Dean and nodded.
“Excellent,” he rubbed his hands together, “we will steer clear of black, then.” Jess picked up the conversation then, explaining that she had an 'entire palate' picked out already, and she had looked on the store's website ahead of time to find exactly what they needed.
Pulling out a notepad covered with her delicate, looping penmanship, Jess began asking to see the suits she had chosen for each of the men in her charge. Dean did his best not to tune the conversation out, and looked around the store, noting the suits hanging in neat rows. He couldn't tell one from another. Black, almost black, brown, weird pattern.... He was definitely in over his head. Turning around, Dean noticed the wall of shirts in a rainbow of colors; pinks, blues, whites, yellows, patterns and plain. It was overwhelming. By the time he turned to look at the ties, he was on sensory overload. He had to sit down. Dean rubbed a hand across his face.
It was a frenzy of movement around him, and Dean could hardly focus, let alone keep up. Fifteen minutes later, Jess handed him three suits, a half-dozen shirts and countless ties. It took him over an hour to try on all the combinations she had chosen.
At long last, Dean stood in front of a three-way mirror in a white shirt, pale, three piece, stone-gray suit, and paisley tie in blues, tans and silvers the same shade as his suit. He turned to Jess, throwing his arms out to his sides.
“Well?” he sounded exhausted. Sam snickered from the armchair he had quickly claimed while Jess ran Dean through the wringer. “Laugh it up, Sasquatch. You're next.” Dean straightened the jacket.
Jess' smile widened.
“That's it!” She turned Dean around to face the mirror once more, fiddling with his tie. She placed her hands on his shoulders, stretched up to her toes, and placed a kiss to his cheek. “Cas will be speechless when he sees you.” Dean blushed under her attentions.
“Alright, alright,” he waved her off, the color high in his cheeks. “Can I get out of this thing yet?”
“Nope,” Jess shook her head. “We need to get it fit, first.” Dean rolled his eyes. The salesman slipped to the back room to call the tailor out. Moments later, a tiny woman with a heavy Italian accent was fussing over him, pinning and marking the suit.
“You look good, this suit,” she said to Dean. “Lucky man.” She reached up, on her tip toes, and patted his cheek before she turned to leave. She spied Sam sitting in the chair. Even sitting Sam was nearly a head taller than her, she was so short. She looked from Sam to Jess. “This yours?” Jess nodded. “Lucky girl,” the woman smiled knowingly at her. With that, the woman slipped back through the door she'd come from. Dean crowed with laughter as he strutted back to the fitting room to get out of his suit.
“Oh, Sammy!” Dean laughed. “Better watch out, Jess, looks like someone's after your man.” Sam rolled his eyes, and Jess pulled Sam up out of the chair.
“Can't say I'd blame her.” She placed a gentle kiss to his flushed cheeks, and began holding suits up against him. It took considerably less time to choose Sam's suit, shirt and tie.
Twenty minutes after Dean had changed, it was his brother's turn to stand in front of the three-way mirror. He was dressed in a French blue shirt, and a suit the salesman had referred to as 'camel', with a pattern to it that made it look like linen. Dean said it was brown. Sam amended it to LIGHT brown, and Jess rolled her eyes at both of them. Jess draped ties over the suit, trying to choose between stripes and solid. In the end, she settled for a silver tie with tiny pink dots embroidered into the silk.
Dean watched as Jess fussed over Sam's outfit. When she turned to the salesman, Dean caught Sam's eye in the mirror.
“Gird your loins, Romeo,” Dean smiled wickedly. Sam heaved a sigh as the little tailor came back out to the fitting area, her face lighting up as she ogled the tall, young man in front of her. She barely came up to his waist. Shamelessly, she looked him up and down before she started fitting his suit. A stepstool was needed to allow her to reach the collar of Sam's suit, and she peered over his shoulder and winked suggestively at his reflection. Sam's face turned crimson. It was an endlessly entertaining ten minutes for Dean, and an excruciating lifetime for Sam.
When the little tailor, Nina, she told Sam, had finished, she stood in front of him and beckoned him to bend down. With a glance to Jess and a glare to Dean, he leaned down slowly. Nina took his face in her hands and kissed both sides of his face. She patted his cheek gently, mumbling in Italian, before she turned to go. They caught the word 'bello', and Sam turned to Dean, who looked like he'd just won the lottery; eyes bright and gleaming, Cheshire-cat grin, and face flushed with restrained laughter.
“Not a word,” Sam pointed to him, “or, so help me...” Before the brothers could start up anything embarrassing, Jess pushed Sam toward the fitting room to change.
Shirts and ties in hand, the men made their way to the register. Dean braced himself for the final cost. He was pleased to see they had gotten everything on sale, and the total came in well under budget.
“Whaddya say we celebrate?” Dean asked as they headed out the door. Sam and Jess both nodded, smiling. “Good. Let's go get Cas and Sweet Pea.” They piled into the Impala, and headed for home.