Valerie -- The Saturday before Halloween
A pair of torn frilly pink panties flapped in the breeze in a place of honor to one side of Valerie while red, ripped men's briefs were hanging off the opposite corner of the town sign. The sundered garments were due to serve as flags welcoming people into town until the last freeze of the coming winter.
The road was closed tonight, but most who drove through town would think they were tattered flags if they saw them at the top corners of the sign. One had to live in Ashen Hollow for long enough to be brought into their confidence or have been born here to participate in the yearly harvest ritual of renewal.
Legend held that several town elders were products of the ritual, though there had not been many conceptions since birth control became widespread. Condoms were forbidden, as was pulling out, but Valerie's IUD wasn't against the rules. Hopefully, no one could see through the beautifully-crafted regalia to tell that the Ashen Hollow's disgraced tomboy was on the raised dais beside the town sign being honored in their most vital ceremony.
Returning to town thirteen years after her near exile, hardly anyone would recognize her face, but anyone of age in the hamlet now knew what her waxed pussy looked like being split by a mammoth cock. The padding under her porcelain mask crinkled as she rolled her head to the side.
Every sense was heightened spectacularly by the ritual. Anyone who wasn't close enough to see the action on the well-lit stage could see her having sex on one of the two giant screens that abutted the Ashen Hollow welcome sign. It was a concession to keep the crowd from pressing too close to the structure and interrupting the ritual.
The male participant's cock jutted from a hairless crotch and disappeared into Valerie's cunt. The harsh term seemed appropriate for the situation in her mind. A surplus of natural lubrication was in creamy streaks along the thick penetrator. She was more turned on than any moment she could recall. The only thing that Val could tell about her mate for the night was that he was tall, extremely well-endowed, and had a pale shade of skin. He also had to be between eighteen and forty-five to have his number drawn at the Harvest and Hunt Festival's culmination.
Somewhere in the sea of very interested voyeurs, Valerie's best friend was watching her have sex and had no idea. Val hoped that he had been successful in finally asking Sarah out. She was a tall, gorgeous young woman who was kind, caring, intelligent, funny, and her best friend's type. Val knew that the woman was taken by the charming young man; it was hard not to be. All he needed to do was ask.
Gordon was the only reason Valerie took the job in the town that once shunned her family. Her unrequited feelings for the handsome young man would have to stay just that. She didn't need to take the risk and blow up the last remaining tether to her family's ancestral home.
"Unnh!" Valerie's scream of ecstasy was partially arrested by the dense foam gag between her teeth and fastened around the back of her head with a padded leather strap. The man fucking her had the skill and the natural gifts to coax multiple orgasms from her form. One of his gloved hands delicately fondled her exposed breasts while the other toyed with her clitty like he was playing an epic, tantalizing guitar solo. The quick movements of his fingers belayed the masterful precision of his aim.
The man was dressed as the Grim Reaper, the Avatar of Winter and Death in this town, his face entirely obscured by dark fabric. He, too, had a gag in his mouth, although that had not been placed until after he had gone down on her to get the ceremony started. It wasn't only his cock that the figure had a high level of skill with, and that wasn't something Valerie carelessly praised.
Her dress had obscured his work after the attendants had torn their undergarments from them to start the festivities. The anonymity of the two participants was of vital importance to the hamlet. It was the reason for the requirements of a costume and mask for all on the fairgrounds, to obscure anyone in the age range that could be chosen.
A few exceptions could disqualify people from the lottery everyone was desperate to win:
1. A woman couldn't be on the stage if already pregnant. The age range was due to the symbology of the woman being fertile and the man being considered virile.
2. Participants had to be free of sexually transmitted infections. Everyone in town who met all the requirements was tested before the festival began. Their results were somewhat anonymized to the best of their ability, removing candidates without explanation.
3. The two chosen could not have any familial relations with each other. The Keeper was the only one who knew both participants' identities and took a vow that prevented them from revealing that to anyone.
4. Once a man or woman had their number called, they could never be on the stage again. This was another purview of the Keeper, as no one else would ever be assured of who was on stage.
5. The most recent exception added to the scrolls was sexual orientation. If one was gay, they could not be chosen, but evidently, bisexuality did not disqualify Val.
Done on the closest full moon to Halloween, the ritual served the purpose of sowing new seeds after the bountiful harvest. It was a renewal of the good fortune that had nourished the burgeoning town for another year and was said to aid in hunting beast and fowl to provide meat for the winter. That was no longer a necessity for survival, as the town was now a suburb of a much larger city with all the modern amenities afforded to that location. Local folklore said that the ceremony was far older than the community and may even predate many of the tribes in the area.
Valerie was surprised that she had been selected. Rumors said the elders could override a selection if it was in the town's best interests. The Keeper knew her provenance and identity but still allowed her selection. Thirteen years ago, at the first grand finale that Valerie had been old enough to attend, her father was chosen in his last year of eligibility.
He refused to break his marriage vows to do his part even if his wife had passed a few years prior, but that had happened before. Val's mom had been gone for three years before his name was selected. His committing the cardinal sin of the night and unmasking started the family exile.
If that had been the end of things, that would have only been a black mark that besmirched the family name if it weren't for a wildfire that flared through the region a week later. Like it or not, the blame was put on him for the fire, not the careless camper and unusually dry year.
After that, her entire clan moved out of the area. Her dad was even let go from his place of business after twenty-five years of loyal service. It didn't matter that he was still grieving and doing his best to keep his family together as a single father of three. The elders zealously protected the town and its traditions.
"Unh! Unk! Gnnn! Gnn!" Valerie yelped out through layers of foam as the Reaper worked her over another precipice. Her whole core tightened as a robust climax shattered all thought. Her eyes clenched shut as a volcano of purples and oranges splattered against closed eyelids.
This orgasm burst joyfully from a pair of closely related nexuses of her pussy and clit. She screamed and thrashed as her sunset-colored thigh-high clad legs vibrated against the man's hips as he continued to stroke earnestly.
A half-decade without cock had been far too long. Vivian had been a great lover and could use a strap-on well, but it was never like this. The stretch and friction were heavenly and couldn't be imitated by someone who didn't have feeling in the thick rod. Her pussy contracted on her invader epically as her whole body thrummed with pleasure like a tuning fork struck and vibrating that bliss into the aether around her.
"Ffff... Ffff... Ffff!" Val tried to cuss, but her outburst was arrested by the gag. Her core took turns with the muscles in her back and ass as she futilely screamed to displace the electric pleasure surging through her. This second climax of the night was far more powerful, and her evening was only beginning. The man dressed as the Reaper was far from done with her. She could barely hear the crowd's cheering as her orgasm finally started to release her.
Val -- Three months Earlier
"This is the space, Val. It's yours if you want it." Thad walked her through the recently vacated warehouse on the edge of the town's fair and festival grounds. "Ashen Hollows doesn't have all that high of a population, but it's in a metropolitan area of nearly a million." He continued unnecessarily. Not only had Valerie done her up-to-date research, but she was also born and raised in Ashen Hollow. "The short drive and high pop density are thought of highly by our forecasters."
"I don't know, Thad." Valerie was waffling. This was the only opportunity to prove herself and manage a project. It was one of the two flagships. She needed to validate herself to move up in the company and maybe finally get one of her designs in place. However, she wasn't sure she could be in Ashen Hollows.
Her family's exile wasn't formal and didn't extend to her father's progeny. Even without the looming judgment of the town, Valerie wasn't sure she wanted to be here. Her high school experience wasn't something that had any pull of nostalgia to it. She was the tomboy who liked football, fishing, and hunting, not the popular girly activities. Once she could no longer be a part of her softball team, she only had a single close friend.
There were vicious rumors that she was a lesbian throughout high school, and she was mercilessly bullied by a vicious pack of cheerleaders headed up by a next-door neighbor who was oddly convinced Val had stolen her boyfriend. Their two principal complaints didn't seem to pass the logic test, but it was high school. Logic didn't often make an appearance.
The head cheerleader barely let Valerie breathe after Val's mother died in an auto accident. One point in the town's present favor was that the hateful shrew of a woman had been exiled from Ashen Hollow. Her banishment wasn't the nebulous variety that Valerie's family endured. A decade later, she would still be arrested for trespassing if seen in town.
"There are no other opportunities this year, and I don't think you want to return to HQ." Thad wasn't the greatest of salesmen, but he had a point. Back home, the general contractor was Vivian, and Valerie wasn't ready to be civil with the woman who broke off their engagement for another, younger woman. "Why don't I introduce you to our general contractor, and then you can decide."
"Thad, have you run this by the elders?" Valerie stopped them as they walked into the office on one of the corners. Thad's eyebrows shot up as if unaware of Val's history.
Interesting.
Valerie kept a smirk from her countenance. Not everyone did their research like she did.
Thad was a decade and a half older than her but another native of the town. Only natives or those who had earned the town's trust and went through the Rites of Belonging were privy to the existence of the hidden cabal that really ran the city.
