Big Shot

Three minutes to nine and you are cleaned up, freshened up, and dressed up. You had decided to play into the girls’ fantasy of this being some super exclusive, high-end entertainment by spiffing up in a steel gray collared shirt and charcoal dress pants. The trousers you hadn’t worn since your high school graduation and they were far more snug than you remembered. Fiona was right. You’d let yourself go soft. Surprisingly though it wasn’t so much your little paunch that tightened the pants as it above the belt line but your plump booty. It was only slipping into these old trousers that made you realize that most of the weight you’d gained had gathered in your behind. As you look at yourself in profile, your hands running over your booty, the memory of Fiona’s huge cock pressed up hard against it flashes through your mind. With minds of their own your anus quivers and your dick twitches. Mmmm. With a shake of your head you **** yourself back into the moment and continue looking yourself over. With the ass of the pants stretched taut it also meant that your crotch had been pulled snug as well making your bulge more obvious than it had in the past.

You pause, staring at your package as Fiona’s mocking laughter echoes in your ears, and consider whether to change back into your usual baggy clothes. Intellectually you knew you had nothing to be ashamed of down there but emotionally, after all of Fiona’s teasing and the many, MANY subtle digs that Allison had made over the years, you perpetually felt yourself lacking. Being the runt of the Bailey litter certainly hadn’t helped those feelings either. In the end you decide to stay as is. Despite her bulge dwarfing her older brother’s Elsie would never laugh at you and Zoey was a sweetheart through and through. Besides, with your face smooth and your shoulder length hair combed back, you were looking pretty damn dapper as you were. The only decision now was tie or no tie? Fuck it. You go all-in and put on your tie and your jacket as well. You really did look like a big shot, as close as you could anyway. You were just missing one crucial thing to pull off this high character but you knew just what to do. After a quick trip down stairs to raid the family’s Monopoly box you return with a pocket full of Benjamins.

There is an extra bounce to your step as you stride up and knock on Elsie’s door. You aren’t waiting long before the door swings open.

There to greet you is you beautiful little sister, this time with a smile on her face. “Hah!” She gasps as she sees your fresh look. Her dark eyes pan up and down your body too many times to be innocent. “Oh my goodness. You are looking very handsome tonight Mr. Bailey.”

“One must look their best for an EZ performance.”

“Of course.” She giggles.

“You are looking radiant yourself, Miss Elsie.” You take her hand, bow and kiss it lightly. She was still in her long robe but, in the spirit of the moment, it was a gown to your eyes.

“Oh! Um, thank you, Sir.” She says with a blush. “Please, do come in.”

The room looks the same as when you last saw it though the music had changed into some softer background tunes. Zoey was nowhere to be seen, meaning that she had to be jammed into the corner that the curtain covered. This is confirmed when you see a sky blue eye peek out to look at you followed by an excited titter. This was all so silly! You loved it.

“The show will begin shortly.” El says as she seats you.

With a snap you flick a C-note from your pocket and hand it over. “Thanks, babe.”

“Pffft!” It took all your sister hand not to burst out laughing as she sees the play money. Her huge eyes sparkle in playful delight like you hadn’t seen since she was little. “Oh my! A big spender!”

“Woo!” Zoey hoots from behind the curtain.

Elsie takes the bill and slips it into the pocket of her robe. With a wave toward her desk she brings your attention to a partly drank water bottle sitting on a couple of books. “Refreshment if you desire.”

“Very good.” You move the bottle to look at the books. “And something to peruse while I wait.” Elsie’s eyes widen as you pick up the top book. “**** Girl?”

“It’s a, um, historical, um…adventure story. Very educational.”

“Sounds intriguing.” As you lift the other book you notice Elsie’s blush brightening. “Son for Hire?”

“It’s a character driven, um…family…um…drama.” She snatches the tomes from your hands and tosses them behind her. “Never mind the books!”

You chuckle.

A flustered Elsie takes a second to collect herself then says. “If you are comfortable, Sir, we can begin.”

Leaning back in your seat you give a nod. “I’m ready.”