Crushes and Couture

Zack Bishop's hand shook slightly as his finger reached for the doorbell to the Woodsens' home. Hearing the series of chimes ring throughout the house, the teenager ran his hand through his short, dark brown hair in relief. The moment he dreamed of since he hit puberty had arrived. He, Zachary Bishop, would be taking his old crush, Hannah Woodsen, to a party as his date.

The series of extraordinary events started with an invitation by Fletcher Wynwick. Eighteen-years-old and a classmate of his, but not more than an acquaintance, Fletcher's life existed on a whole 'nother level than Zack and his closest friends. Not too many other high school seniors around the country were holding the grand reopening of their renovated historic lodge that they won in a card game from a distant relative before they graduated. But Fletcher was, and he sent out invitations to all the leading families in Azure Rocks. The Bishop family received one in honor of their long history of serving as doctors in town. Another invitation had been sent to the Woodsen family for the equally long history as the leading attorneys for the local citizenry.

Knowing that his sister, Taylor, would have her boyfriend and childhood friend, Peter Zander, as her date, and that Ashley Woodsen would bring her boyfriend, Brandon Cole, had left Zack dreading the possibility of being the third wheel at times. While he would have some friends at the party, he didn't want to be one of the few guests without a plus one at his side. So one evening Zack did the unthinkable; he mustered up the courage to wait outside for Hannah to leave after visiting Taylor, and popped the question: Would she go as his date to the party?

In all his dreams and nightmares, Zack never imagined the response Hannah gave him. "Well done, Zacky. Pick me up when you're all sharp and ready."

And so now Zack waited on the front porch, rubbing his sweaty palms against the pant legs of his nicest dark blue suit--the only suit he owned--a brand new one he pestered his parents into buying last week.

The moment the door opened and the gorgeous Hannah Woodsen stepped out, making his dreams spring alive, almost proved too much for Zack, who felt light-headed. Fighting off a fainting, Zack marveled at the voluptuous vision, who wore a snug, short scarlet red dress. Her wavy blonde hair flowed down her back as her mischievous baby-blue eyes stared into his icy-blue ones with a smug grin.

"It's Zack, Ash! I'll see you there," Hannah had briefly turned to yell back inside to her sister. "My, my, don't you clean up nicely. Looking very handsome, Mr. Bishop."

"And you look as breathtakingly beautiful as always, Miss Woodsen," responded Zack, wondering where the hell that came from, but he liked it. Her appraisal of his suit gave him a reason likewise to admire her, noticing her ample breasts straining against the velvet fabric.

"Smooth, very smooth," Hannah giggled, pleasantly surprised by his demeanor. Taylor had pleaded with her best friend to take it easy on her brother and not to go too far either. However, Hannah would have never done that to the teen who she knew had a crush on her when he first started to notice girls. She didn't want him to freeze up, ruining the night, nor would she hurt the feelings of the cute little twelve-year-old that gave her flowers he picked out of the Whites' flowerbed.

"Well, then, shall we be off?" Zack inquired, gently taking her hand into his.

"Yes, we shall. Let's go live life like the rich and shameless," Hannah barked out a laugh.

Zack led her to his mother's black sports utility vehicle, opening the passenger door for her like a gentleman. Sliding into the passenger seat proved a little tricky with her tight, short dress, but Hannah pulled it off. As Zack ran around the SUV to the driver's door, the blonde heard a voice from behind her.

"So, are you planning on purpose to pop those girls of yours out on the dance floor tonight?" Taylor asked with a smug grin, sitting behind the driver's side seat.

"I hope she's not planning on dumping Zack for the first lecherous businessman that wants a new trophy wife with real D-cups," Peter Zander piped in from behind his ex-girlfriend.

"Oh, great, you brought the chaperones," Hannah remarked to Zack as he got behind the wheel.

"Hey, what about me?" squeaked a voice from all the way in the back of the SUV.

"Sorry, we had to bring one of the kids with too," Zack joked. "You sure you okay back there, Chloe?"

"Just don't take any turns too fast," the redhead hopelessly requested, sitting in the trunk section of the vehicle, praying that her dress didn't get too wrinkled.

---

"The sexiest one?" Fiona repeated as her son walked over to her, near the large mirror. "Do you not realize how important tonight is to us? We have relatives coming from all over the country, many we haven't seen in years if not decades. The Canadian Wynwicks even sent a contingent for the reopening, and only a couple of them have ever set foot in Azure Rocks since they were banished after the family civil war over a hundred years ago."

"Yeah, yeah, I know all this, but who really cares. They can stay up in Canada for all I care. If it weren't for them this lodge wouldn't have been empty for nearly as long," Fletcher responded dismissively, having little patience for family politics.

"Well, your grandfather and his brother felt strongly enough about mending those fences that it cost them their lives. Never forget that," Fiona reminded her son, fighting to control her emotions. It had been thirteen years ago that her father, Fenton, his brother, Woodrow, and her cousin, Wyatt, died in the seaplane accident deep into the Canadian wilderness. It had taken a miracle for the fourth member of the party to survive. Time hadn't lessened the sting that Fiona felt over losing her beloved relatives.

"I haven't forgotten that if they would have sold this lodge to Uncle Woody like he wanted, then they would have never been in that plane," Fletcher bitterly added.

"Fletch, I know you resent how most of our relatives have treated us, but tonight is not the time to air those grievances," Fiona said, moving forward to put her hands on his shoulders. The act caused her son's eyes to lock in on her marvelous bosom, barely constrained in the skimpy, lacy black bra. "We need their goodwill at the moment. Kermit's only waiting for the day that Uncle Myles passes to make a move against me. He's going to be working any relatives that have votes in the foundation with that goal in mind tonight. So, please behave, darling. Do it for Mommy, okay?"

The combination of those jiggling, big tits and hearing the way she said the word "Mommy" caused Fletcher's cock to jerk. "Fine, I'll try and behave. But if they start calling you 'that teenage slut' I'm not going to be pulling any punches."

"I know you won't, Fletch, I know," Fiona softly remarked, patting his cheek. "Now, the fact that so many relatives still view me as that wild teenager who irresponsibly got knocked up, I certainly can not wear the sexiest dress. I need to look elegant and professional. Okay, maybe just a tad bit sexy," she added with a small grin.

"Well, that knocks the red dress out of the running. You wear that, and our relatives will be too busy trying to figure out how distantly related they are to you. And if that counts as being too distant not to be ." Fletcher's anger fully dissipated at the bright grin his complement brought to his mother's face. "Wait, why would you bring that dress if--oh, this was another of your little tests for me again. You know I hate when you do that."

"All part of being a parent, darling," Fiona noted, pleased that he recognized the test she laid out for him. "Okay, so the blue dress it is. Blue is my favorite, anyways."

"Nope, I don't like that shade of blue on you. I'm going to need a third option."

Fiona placed one hand on her hip, cocking it out in a teasing fashion. "And what makes you think there's a third option?"

"Mother, with you there's always a third option. And a fourth, and a fifth..."

"Okay, smartass, let's see if you can pick a better dress than I can," Fiona shot back. "But we need to hurry, some guests have already started to arrive."

"Already? It's not even six yet," the teenager remarked after glancing at the clock.

"Some of the older guests will want to arrive early and leave early. Not everyone is a teenager that plans to stay up to dawn dancing and drinking," Fiona replied, her words getting fainter as she walked away from him.

Fletcher turned back from the clock, only to clench his fists. Are you serious? With Fiona's back now to her son, he could see that her lacy, black panties were tinier than he expected with a thong back. That left her pale, flawless ass cheeks to torment him as they bounced with each of her steps. Why does she always do this to me? It's not normal to walk around half-naked in front of your son.

Standing, staring in awe, the eighteen-year-old watched as his thirty-four-year-old mother walked out his bedroom, leaving his door wide open, and opened the door directly across from his. Stepping into her room, Fiona took a moment to turn back, shooting him an impatient look. Springing into action, Fletcher moved to exit his master suite.

Initially, Fletcher had planned to fully restore the lodge to its original glory. However, he ended up reconfiguring the second floor due to extensive water damage to the original master bedroom. A giant hole in the floor down to the drawing-room made it an easy decision to scrap the whole bedroom, leaving now a great room with a cathedral ceiling in its place. The teenager then took two bedrooms and converted them into the new master bedroom with a modern bath suite. The new layout meant that just outside of his and his mother's bedrooms was a balcony overlooking the great room.

Exiting his door, Fletcher paused in surprise when he remembered the balcony only a dozen feet from his door. Considering his mother's concern over not looking too sexy, he couldn't figure out why she would risk someone downstairs looking up and catching a glimpse of her in her underwear. Sure, the risks were low, but it still felt like a careless move by her.

Entering his mother's bedroom, Fletcher scanned the large room. Like his newly renovated suite, his mother's room also had modern upgrades with a new bathroom and walk-in closet. Finding her browsing through a dozen dresses that hung inside, he smiled.

"Geez, Mom, do you think you brought enough dresses from home?"

"Well, I need to be ready if my son goes on a binge of party dinners at his new estate," Fiona teased. "Oh, and I needed to clear out some of my closets back at the condo."

"See, that's another reason you should agree with my plan to move to the lodge fulltime. The condo is too small for all our stuff."

"Darling, never call our penthouse condo too small around other people. It makes you sound like a spoiled, rich brat like your cousins," Fiona admonished him. "Always remember that not everyone is as fortunate as we are."

"I know," her son agreed, before pouting. "Still, it would have been nice to have a backyard to play in when I was little."

"You had all of Founders Park to play at."

The condominium that they lived in was one of the most exclusive properties in all of Azure Rocks, located in the heart of the downtown, on Founders Square. It was the only residential property on the square, but it never felt like home to Fletcher. As a five-year-old, he had hoped they would move into his grandparents' house with his widowed grandmother, but Fiona had zero interest in living on the same street with so many relatives that had shunned and shamed her. Instead, his mother's sister, Sela, moved her family in to keep his grandmother company.

A young Fletcher once dreamed of finding a way to gain control of Wynwick Manor, the historic family seat, located just a few doors down from his grandparents' house. It resided in the hands of his elderly Uncle Myles, the head of the family, but it most certainly would be handed down to his mother's cousin, Kermit, someday soon. Now, with the legendary Wynwick Lodge under his control, Fletcher finally had the home he always wanted, and one that nearly every relative envied or despised him for owning.

"Stop! That one right there, let me see it," the teenager ordered, snapping out of his thoughts as a silver dress caught his eye. As his mother held up the dress, Fletcher nodded several times. "Yes, that's one. It's perfect."

"I don't know, honey, it's a little more risqué than I wanted." The silver-haired beauty gave her son a doubtful look. "Maybe this other one will work better," Fiona suggested, pulling out a baby blue dress.

"No, no, no, that won't do at all. We don't have time to argue, the guests have started arriving, remember? Just hurry up and try it on."

Despite her concerns, Fiona figured it was easier to try the dress on and then argue with her son, rather than argue first. Taking the dress into the bathroom, she closed the door behind her. That left Fletcher a moment to reflect on the upcoming night.

Moving toward one of the windows, he admired the estate's lush grounds. Most people would expect an abandoned property to become overgrown, but the Wynwicks weren't most people. Although the of his ancestor, Lincoln Wynwick, resulted in the Canadian branch of the family becoming absentee owners, the Azure Rocks Wynwicks spent decades secretly sneaking gardeners onto the property to maintain the grounds. That love for their heritage left hardly any work to be needed when he won control. Which had been lucky since the rest of renovations cost a small fortune, far more than an eighteen-year-old like him possessed.

As he watched the caterers and party planners scurry around the grounds for last-minute work, his mother's vibrating phone pulled Fletcher from his thoughts. Wondering if it pertained to him, he moved over a few feet and checked the screen. A name very familiar to him flashed across the screen, along with a message intended for his mother.

"Well, what do you think of your choice?"

Spinning around, Fletcher let out a loud whistle at the sight of the woman before him. Standing in a long, silver strapless dress, it consisted of a slightly lighter shade of the color than her hair. It dipped low in front, showing off the top edges of the strapless, black lace bra she now wore underneath.

"That's the one. The perfect mix of elegant and sexy," Fletcher nodded, once again willing his dick to not get hard at the sight of his enticing mother. "It's very Silver St. Cloud."

"Fletch, I can't wear this one. It's cut far too low. I'll have to wear an even flimsier bra than this one," she gestured to her prodigious bust, ignoring his reference to the Batman character that he loved to say she looked like ever since he was a little boy. "I did say I didn't want to remind the family of my wild teenage reputation."

"And I want you to flaunt it to them. Remind them all how they underestimated you," he passionately stated, while walking over toward the door. "Besides, my existence reminds them of it every single day."

"Where are you going? I need help with the zipper of any dress!" Fiona yelled at her son as he started to walk out the door.

"Don't worry; your little spy just texted you that Aunt Sela arrived. She can help you finish getting ready," Fletcher revealed, after popping his back into the room. "Now, excuse me, but I need to get dressed."

"You're already dressed."

"Mother, the way you look in that gown means I need to step up my game."