A Wayward Wager

It was Carly’s idea to get married upstate. If it had been up to her fiancé Blake they would have tied the knot somewhere else. 

In fact, Blake would have imagined a far more lavish destination. A stunning European castle; a sun-soaked private island in the Maldives, or perhaps the Great Pyramids in Egypt.

Carly, however, was a Rochester girl at heart and so she had insisted on following her childhood dream. That was a wedding set in New York’s Finger Lakes, a series of narrow, picturesque waterways directly south of Lake Ontario.

It was where her family had taken many of their summer vacations, located as it was barely an hour’s drive from their hometown. It was in the Finger Lakes that Carly, as a little girl, had first set eyes on a castle. She fell in love with it at first sight. When she learned, soon afterwards, that the place hosted weddings she vowed that one day she too would get married there.

Years later, she learned that her dream castle was hardly the genuine, medieval article that one might find in Europe.  It was in fact a late nineteenth century Romanesque revival perched on the shore of the largest of the Finger Lakes. 

It had been built by a ridiculously wealthy robber baron who had been something big in steel. Yet, what caught Carly’s imagination was the story of his wife. Springing from far more humble origins than her husband, she had eventually become the lady of the manor after her philandering and wayward spouse had contracted syphilis. He had later been declared insane and finally confined to an asylum to pass his final years. 

“You must be kidding,” Blake said when she told him of her choice of wedding locations. “Of all the places we could get married, and you want to do it there?”

“Wait until you see it, you’ll love it,” Carly responded. “Besides, it will make things super easy for my family and some of my old friends. You know as well as I do that it wouldn’t be realistic for them to get to Lake Como or some private island halfway across the world.”

Blake smirked with more than a hint of derision.

“Of course, the brokies!” he sneered. “We’ve got to make it easy for them. We know people who are talking about getting married in space and we are going to do it in good old New York state.”

Not for the first time in their two-year relationship, Carly realized that her beau really wasn’t the nicest person.

“Oh, come on Blake, not everyone can make millions in tech before they are thirty-years old.”

That seemed to mollify him a little. He puffed his chest out, proud that his fiancée rated his talent and success. 

“Ok,” he said, holding his hands up. “If it really is your childhood dream, let’s do it there.”

Carly knew that Blake would acquiesce, eventually. He did care about appearances, up to a point. But he cared even more about having fun and making money. Ultimately, a Finger Lakes wedding would not prevent him doing either.

Benton Castle would allow the couple to invite up to 250 guests. The majority of those would, of course, be Blake’s family and friends. His wealthy parents were still based on the West Coast as were many of his friends. Those friends were mainly fellow “tech bros” he had met through Stanford, Google and the plethora of start-ups he had gone on to work in. 

It was in fact Blake’s latest venture, an AI text-to-game generation company, that had brought him to New York City three years ago. His father’s venture capital company had kicked in a significant slice of funding to the company that had been co-founded by Blake and his friend Anshu. 

Blake had taken the CEO role while Anshu, acknowledged in the industry as one of the most gifted architects of the “large language models” at the heart of AI, was the chief technology officer. Various tax and recruitment considerations, as well as Anshu’s strong lobbying, had led them to set up shop in the Big Apple, rather than on the West coast, which would have been Blake’s preference.

It was in New York City that Blake and Carly had met. She had studied undergraduate at New York University and then gone on to Columbia School of Journalism. She had, however, then never actually practiced the gritty trade of news reporting. Instead, she had landed a role as an editor of non-fiction books at a major publisher. It was a job she loved. 

The social side of the business was just as important as the time she spent at her desk. It had been at some high-end reception or other that she had met the overgrown frat boy who would now become her husband.

Carly had felt instantly drawn to Blake’s world of wealth and seemingly effortless success. Everybody else she knew had to struggle and hustle to get far less. It was true that she overlooked some of his less-than-ideal personal traits. Yet, there was a roguish charm and a magnetism to him that was hard to ignore.

Now, with their wedding at Benton Castle beckoning, the bride-to-be threw herself into the preparations. 

Going against the tradition that demanded bride and groom stay apart until the big day, she decided that the event would be a three-day affair in line with the special package that the place offered. That would mean a smaller party traveling to the venue a couple of days before the ceremony to enjoy rafting and kayaking on the lakes as well as some golf and a pre-wedding dinner.

That group would essentially be Carly’s bridesmaids and Blake’s groomsmen.

She asked her oldest friend Heather to serve as maid of honor. Carly wanted someone level-headed to be in her corner through the most important weekend of her life. She also wanted someone who could keep the more excitable of her bridesmaids in line. Heather fitted the bill perfectly. Unmarried and unattached and somewhat plain, her friend was one of life’s natural nurturers.

Together, they finalized the list of six other bridesmaids. Three came from Carly’s more recent Manhattan set. Heather barely knew them so could hardly object. The other three were old friends from Rochester. Two of them were solid, uncontroversial choices but one did raise some protests from Heather.

There was something about Emma that had always intrigued Carly. Blessed with beauty and sex appeal, she had been the boys’ favorite in high school. It was a status that she enjoyed unapologetically and gave rise to a lifestyle that Emma continued into adulthood. To all appearances, she pursued serial monogamy with the most eligible men in Rochester she could lay her hands on. 

Nonetheless, many in her circle suspected she did not hesitate to indulge her impulses in an extracurricular fashion when the opportunity arose. She was, however, also known to draw the line firmly against unwanted advances, sometimes almost after the fact. As far as her friend group, at least a couple of guys had seriously overstepped the mark with their attentions toward Emma.

“Are you sure Carly?” Heather said. “I hate to say it but I have to be blunt: She is a bit of a slut.”

“Perhaps, but she is fun. She will help us get the party started.”

Carly herself had always been regarded as physically attractive. Let’s face it there is no way she would have drawn the attentions of a somewhat superficial minded man like Blake if she did not pass muster on that front. Yet she had never had the kind of looks that would stop traffic or drive men crazy. 

Emma, on the other hand, was just such a siren. And it didn’t threaten Carly one bit. It just fascinated her.

Heather finally relented, realizing her friend was set on this risky choice. 

“Ok, I hope you know what you are doing.”

---

It had taken Blake a few days to get his head around the fact that he wasn’t going to have the kind of glamorous international wedding that he had attended for other friends. After that, however, he didn’t dwell on it too much. One of the things he liked about Carly was that she was far humbler than most of the bratty rich girls that he had known.

Blake’s parents had nagged him a little about at least considering some kind of pre-nuptial agreement. After all, there was a significant difference in the wealth of the two families. However, being good West Coast liberals, they hadn’t pushed the matter too hard. 

Their son had waved any concerns away with his usual nonchalance. Not out of sentimentality but more from the complacency and recklessness that were his trademark.

So, Blake resigned himself to the Finger Lakes and turned his thoughts to how he could make the weekend as enjoyable as possible.

The first order of business was to choose a best man. He suspected that Carly would have preferred he choose his sensible and sober business partner Anshu. Strangely though she didn’t push the issue. That was another plus about his fiancée: she gave him the space to live his life.

As much as he loved Anshu, Blake knew he needed a different kind of ringmaster to produce blockbuster weekend he wanted. He turned therefore to another dear friend, the biggest hellraiser he knew, Scott.

In another era, Scott would have been a buccaneer. In modern times, he was the closest thing, a swashbuckling venture capitalist who knew how to enjoy himself both in business and in life. He had a voracious appetite for partying and for women, pursuits that filled his weekends to the brim. However, despite all the fun he allowed himself, Scott would always be fresh and crisp on a Monday morning, ready to do battle in the boardroom.

Fittingly, for a venture capitalist who bet on which technologies and business models would win, Scott loved to gamble on just about anything. He was at home at a casino table, at the racetrack or just passing time on the Fanduel app.

Therefore, Blake wasn’t completely surprised when, over an after-work drink one day, his best man proposed a rather unusual wager.

“Let’s inject a little bit of fun into the weekend,” Scott said.

“What do you have in mind?” Blake asked, intrigued.

“Well, you get married on the Saturday so Thursday and Friday will be your last days of freedom.”

“True,” Blake said, still not entirely sure where Scott was going with this.

“I think we should find a way to make sure you enjoy those final days to the full, don’t you?”

“Yes, but we will be at castle on the lake with the advance party. It’s not as if the fellas can slip away to a strip club or something,” Blake said.

“You won’t have to,” Scott said.

Blake raised a quizzical eyebrow.

“There will be six bridesmaids there right?” Scott continued.

The penny dropped for Blake. He thrust both palms up in the air.

“Whoa! Hang on their buddy! What are you suggesting?”

Scott grinned and fixed his friend with a mischievous look.

“I think you can guess but I will spell it out. Let’s have a little wager. If you can bang one of the bridesmaids before you get married you win. If you can’t then I win. Simple.”

“You are one sick puppy, you know that,” Blake said. 

But the groom was already smiling.  

Scott continued: “Here are the stakes. A gentleman’s agreement. You win then my firm kicks in some serious cash into your company in your next round of funding. I win, then you figure out a way to get us some stock in the next round at a very healthy discount. Are you in?”

Blake pretended to look shocked but then burst out laughing.

“I’m in!” he exclaimed, slapping Scott’s hand with a particularly enthusiastic high five.

---

After weeks of planning, the wedding weekend finally arrived. Carly could hardly contain her excitement. This was really going to happen.

She and Blake had decided to travel to the venue independently of one another to maintain at least some sense of tradition. They would have separate rooms for the Thursday and Friday nights before reuniting for Saturday, their wedding night.

As her car passed through Benton Castle’s wrought iron gates, Carly felt her heart flutter. Nestled on the shore of the lake, the castle rose majestically from the lush green gardens that surrounded it. The sunlight glistened off its rounded turrets and large imposing entryway, giving it an ethereal glow. 

She and Blake had visited just a couple of months prior for a planning meeting and Carly had been there many times before. This time, however, felt different. There was a new and intoxicating magic around the place.

As she stepped out of the vehicle, Carly felt as if she was in a fairytale. She smelled the air, fresh and clean with a hint of mist. The next thing that struck her was the potent aroma of the blooming flowers that adorned the surrounding gardens.

This is where her dream would happen.

Thursday afternoon saw the advance wedding party settle into the venue. Splitting into two groups, the boys hit the nearby golf course while the girls opted for a long lunch and a leisurely walk around the lakefront gardens.

That evening it was drinks and dinner at the castle. The two groups would fraternize in earnest for the first time.

Some of the groomsmen and bridesmaids knew each other from the couple’s New York circle. None of Blake’s male friends, however, had ever laid eyes on Emma.

Most of the advance wedding party had already assembled in the castle’s main bar by the time Emma breezed in. Without trying she drew the eyes of every man and woman. Her bolt upright carriage and head titled slightly upwards screamed sexual confidence. Then there was her black dress hugging her curves and her long hair cascading down her back. Her makeup was minimal, but it didn’t do anything to stop her natural beauty from shining through.

Heather, the maid of honor, looked at Carly and subtly rolled her eyes. But the bride-to-be only smiled back at Heather and turned to greet her beautiful bridesmaid. She didn’t feel overshadowed in any way. In fact, she was happy to see Emma looking so captivating. 

Carly looked over towards Blake and his best man. She saw Scott clap a hand on Blake’s back and motion with his head toward Emma. That was a little strange, Carly thought. But the thought didn’t linger long. She was happy in the fantasy world of the castle and her friends. It felt as though they had all been transported to a very different place. A place where the rules may not be quite the same as in the real world.

Perhaps that was why she did not worry as all the guys, including Blake, eventually found themselves in conversations with her bridesmaids. To the outside observer, some of these exchanges may have appeared downright flirty.

Carly did, however, do a double take late in the evening as she passed by the bar to see Emma with her back against a pillar and Blake with his hand reaching across to the same pillar. It was almost as if he was pinning the bridesmaid into an enclosed space as the two talked. 

Blake certainly looked more than a little worse for wear. As soon as he spotted Carly he withdrew the hand that was reaching across Emma as though it had suddenly been scalded by a hot plate. 

Carly just smiled back and continued to the bathroom. Despite the lecherous looking antics of her husband-to-be, she felt a strange calm. Whatever the castle’s plan was for her wedding weekend, it would unfold the way it was meant to. She thought about the woman who had become the lady of the manor more than a century earlier. Perhaps Carly would find a way to follow in her footsteps.

On Friday, the female and male sides of the wedding party would come together during the daytime. Again, it seemed to run counter to tradition. But that was just the way that things were done these days.

The plan was to do some kayaking and rafting on the lake in smaller groups in the morning, and then bring everyone together on a pontoon boat for a relaxing afternoon.

The morning started out with high spirits, which got even higher as the day wore on. Perhaps some of the party were still intoxicated from the previous evening. Or perhaps it was the surreal feeling of hanging out with a couple in a group that would never, ever convene again. Or maybe it was just the magical atmosphere of the shimmering castle on the lake. 

Whatever was in the air, it soon brought out some crazy behavior.

At one point, Blake and Scott were on a raft with Emma and another bridesmaid called Susan. Scott had brought his hipflask of bourbon and all four rafters in the group partook enthusiastically. They giggled, at times uncontrollably. It was as though they didn’t have a care in the world.

Then another boat came close to them. It seemed to be an all-male group completely unrelated to Carly and Blake’s wedding party.

Scott looked at Emma.

“Why not give them a show?” he said.

The bridesmaid feigned ignorance.

“What on earth could you mean?” Emma said sarcastically.

Blake took over.

“Get those boobs out,” he said.

Emma laughed loudly and, to the surprise of the two men and Susan, complied. She lifted her shirt and turned to the other boat. There was no bra underneath. 

Later that evening, the entire wedding party sat around a large table in a private dining room at the castle. Once again, the drinks were flowing freely and everyone seemed to be having fun. Suddenly, however, Carly noticed that two of the group were missing. Her fiancé and Emma were nowhere to be found.

Carly felt her heart race. Could Blake really cross such a line, at this own wedding of all places? Something compelled her to get up from the dinner table. She didn’t know what she was going to do or where she was going to look but she had to find out what was happening.

She saw Scott notice her rising and he shot her a look. He didn’t look particularly worried. Nothing ever concerned Scott. But there was a strange look of guilt on his face.

Carly stumbled out of the dining private room and into the ornate hallway. Something drew her toward the elegant men’s restroom. She stopped for a moment outside the stained-glass door and the sound was unmistakable: the groans of a couple having sex.

For some reason, Carly was not surprised in the least. She took a deep breath and gently opened the main door of the men’s restroom. She then passed the area with marble sinks and their elaborate bronze taps, all the while hearing the groans getting louder. 

She reached the old-fashioned urinals and saw a middle-aged man unrelated to the wedding party zip up his pants in a hurry. He showed no signs of surprise to see a young woman in the men’s lavatory. Instead, he gave her a look of pity and then was on his way.

Carly steadied herself with another sharp intake of breath and walked towards the stalls. There was no doubt about where the noise was coming from.

In fact, they were doing it in the penultimate stall. They hadn’t even bothered to shut the door. Carly saw Blake’s black dress pants puddled around his ankles, the tails of his previously crisp white shirt floating around his bare backside. That backside continued pumping, a couple of slim and tanned legs wrapped around it. Some of Emma’s long tresses were visible behind Blake’s head.

The fornicating couple were utterly oblivious.

Time seemed to freeze for Carly as she stood with the horrific scene in front of her. Another deep breath, then she did what she knew she had to.

“You fucker!” she screamed at the top of her lungs. “You absolute fucker! You fucker! What the hell are you doing!”

Afterwards, she was surprised that much noise could come out of her slender frame. She was sure half the castle heard her.

Blake reacted surprisingly slowly, given the gravity of the situation. He turned his head around and Carly could see in his eyes that he was utterly inebriated. How he had managed to coax his member into action in this state was anyone’s guess. He pulled off of Carly’s bridesmaid and reached to pull up his pants, hands fumbling for the waist of the garment that lay at his feet. He almost keeled over with the effort.

Blaked looked blankly at his fiancée.

“Oh fuck!” he slurred.

Meanwhile, after Blake had pulled off her, Emma has slumped back onto the toilet seat in the stall. If anything, she seemed even worse for wear than her new sex partner.

“I didn’t mean it,” she said, unable to look past Blake to Carly. “He made me do it. He forced me.”

---

On Saturday, the bulk of Blake and Carly’s guests arrived for the ceremony and the banquet that was to follow. They included the parents of the groom and bride as well as dozens of other relatives and friends.

The assembled group of well over two hundred sat in Benton Castle’s opulent ballroom. Sunlight streamed in through the stained-glass windows. Then, at around 3pm, the sun shut off abruptly when a bank of dark clouds interrupted its path. Moments after that, Carly looked at Blake and said, softly, “I do”.

Carly’s maid of honor Heather had spent most of Friday night trying to talk her friend out of marrying the fiend who now stood in front of her. However, to Heather’s amazement and utter consternation, Carly’s mind was made up. The bride was, or so she told maid of honor, going to stick by her man. Through thick and thin.

After the ceremony, the bride and groom sat at the head of the banquet table. The entire room was alive with fun and anyone who hadn’t been there the night before could have guessed the depravity of the events that unfolded in the men’s restroom just down the hallway. Unless someone had told them. 

Nobody heard the three squad cars that pulled up in the castle driveway. The uniformed officers that emerged from them were barely noticed as they strode through the lobby and into the banqueting hall.

Heads did turn finally turn in bewilderment as the Seneca County deputies reached the head of the table. Everything, however, happened far too quickly for anyone to process it properly. 

Anyone, that is except for Carly.

“Blake Carlton?” said the lead officer looking sternly at Carly’s new husband.

“Yes.”

“You are under arrest for the rape of a member of this wedding party. You have the right to remain silent. Anything you say can and will be used against you in a court of law. You have the right to speak to an attorney, and to have an attorney present during questioning.”

In that moment, with guests paralyzed by shock, Carly looked around the walls of the huge hall and into the manicured grounds beyond. She felt as though this magnificent and magical kingdom was now all hers.