Chapter 1

Brothel Night – Wilks Estate Outside of Nashville

Auction

The pretty redheaded waitress, her slender teenage body sheathed in a sheer black lace chemise, set Zack’s drink in front of him, a draft beer. Malory was a recent graduate of Holy Saint-Ursula Preparatory and a former participant in Brothel Night. She was pretty and smiled at him as he admired the small perky nipples that peeked at him through the sheer fabric. Looking around he was the only teen boy among the crowd of older men. At the moment his mind was elsewhere, not on Malory’s smile or tits he was thinking of another girl.

Zack had finished his first date with a girl from the ‘Brothel’ and was down at the parlor lounge. He had been one of the first into a room with his girl so was one of the first out after his hour. The two large first-floor rooms were tastefully decorated with leather club chairs, love seats, and a few cloth, and leather couches with low tables in front of them. Half a dozen Gold and Platinum Recording Industry Awards hung on the walls, along photographs, and a few pieces of memorabilia from Charlie’s time touring with his band.

On the east wall was a bar with a fine oak top and three bar stools where a good-looking blonde bartender directed the two waitresses. At the far end sat a billiards table and a large-screen TV. On the west side of the rooms, the series of glass doors that normally gave the room a view of rolling hills were folded open onto a large patio. Outside a portion of the patio was covered by a white-striped party tent that contained a small buffet area, stage, and metal café style tables and chairs.

His attention was on his device (phone) and the dot displayed on the floor map. The dot represented the location of his best friend and neighbor Hannah. On his device, Zack could see where any of the thirty-one teenage girls who were ‘working’ this evening were at any time as it was tied to the biometric wristband that they each wore. The wristband didn’t replace the girl’s devices, they just provided biomedical data on the wearer’s body to the nurses. In 2029 the ‘device’ had everything a modern teenager needed.

At the moment Hannah was on the second floor, in the second bedroom from the end of the west wing. The west wing had fewer rooms than the south wing according to the layout.

Zack sat in a comfortable leather club chair near the bar sipping his beer. Around him were men who hadn’t bid on a girl for the first hour. They were talking with the scantly clad teenagers from Saint-U Preparatory over drinks or even shooting a game of pool at the far end of the room while they waited for rooms to open up. His cock was climbing back to hardness just watching all of his peers walking around with nearly nothing on, just sexy revealing lingerie. Most ignored him a few waived or winked as they strolled by.

Tonight, the girls were dressed in revealing sexy body cage-style lingerie that highlighted their young bodies, and breasts, and drew attention to their ass or vulva. Many of the 25 invited male guests were still upstairs with a ‘date’. According to his dad, probably a third of the men were fathers of some of the teenage high school girls who were ‘selling their bodies’ for charity tonight. The rest of the men either had teens attending the 9-12^th grade Prep School or were alumni connected to the Prep School and could afford to attend tonight’s fundraiser.

Holy Saint-Ursula was an exclusive institution, after all, founded back in 1983 as a private Catholic High School. Tonight, Friday was the first of the weekend’s two Brothel nights. Each with around thirty ‘eager volunteers’ from the small but prestigious Nashville Prep School. Tomorrow, Saturday, was the new ‘all family’ invitation-only Brothel Night fundraiser.

Zack had spent an hour fucking his school’s seventeen-year-old head cheerleader. Before today Maria didn’t even know his name, now she did, he left his mark. Having a fresh fuck under his belt, he shouldn’t be feeling jealous knowing that his best friend Hannah was entertaining another man, probably one of their friend’s fathers, upstairs. But he was a little, even after banging big-tittied Maria for an hour.

Hannah was fourteen years old, blonde, skinny with a shy personality until she warmed to you. She was his neighbor and first sext date experience. His mind wouldn’t let go. Was she done yet? She had been ‘bought’ in the auction, so she had gone with a client for a full hour of sex. With slightly staggered start times it was hard to guess when she would be done.

He was tempted to request her room’s video feed on one of the 50-inch 8K monitors placed strategically around the room or he could just walk upstairs and look in on them. The house rules encouraged voyeurism, but he wasn’t really in the mood. Zack slowly sipped his beer, a lager from Germany, and watched men and girls having sex on the random room feeds that changed every 30 seconds. After a couple of minutes, he caught a glimpse of Hannah on her back skinny legs wrapped around a man’s hips in the closest monitor.

On his list of girls that he desired, was a busty Saint-U cheerleader named Maria Gomez. She was an unapproachable senior he had admired from a distance as she led the cheerleading squad. Maria was his first choice, the one he wanted to win in the silent auction.

A big ask of his dad, who had agreed to pay for his son’s first choice or second if it came to that. Brock had to outbid other admirers for the gorgeous Latino teen. She was a busty DD (so it said so her profile) seventeen-year-old Hispanic girl, with an attractive face, who could dance and bend like a Las Vegas showgirl. Maria was not even aware of Zack, a sophomore, existing much less giving him the time of day on campus if they passed in the hallway.

So, this evening he made it his goal to make her remember him. His dad came through winning her first date during the silent auction. His dad gave him some fatherly advice before they went their separate ways.

“Zack before you go. Some advice.” His dad said as he looked at the assigned room number on his device.

He nodded his head as he watched Maria head upstairs in the green cadge lingerie she wore for tonight. Green for Saint-U perhaps, one of the two school colors.

“If you want to have ‘fun’ with her. Find out her motivation, and what she wants from tonight. Do that and you will have a better time. Maybe even make a friend.” Brock said as he tightened his kimono’s belt.

Zack must have had a blank look on his face.

“Think about it. Maria is the top dog on the cheer squad and one of the popular girls. She wants to win tonight. Wants to walk away with that gold Tiffany’s bracelet that says she was the best ‘whore’.” Brock said as he drank the last of his lager.

“Thanks, Dad. I’ll try.” Zack said his mind was already working with the information his dad gave him.

Zack ran Maria through the paces during the hour they had. She was not very happy when she found out her ‘date’ was another teenager. But she had to do what he told her, those were the rules. His eyes roamed over Maria’s body, all 5’4” of her and those big tan DD hangers wrapped in the green straps of the cadge top. Her waist was narrow, her legs strong, a dancer’s figure. Her long black hair hung in a tight braid down her back like most of the girls tonight.

They stood by the bed. “Kiss me then get on your knees.” He said as he took off his kimono and tossed it on the bed.

He could see Maria’s hands ball into fists at her sides as she tried to stare down Zack.

“Listen Maria. I know you want to win tonight.” He said.

Maria’s face softened “Yes, I do.” She said, still not moving.

“Do what I say, and I guarantee a few extras that will up your standing in the totals.” Every date, after the auction, was a fixed price but extras like deep throating and anal cost more. The winner was whoever had the most money raised at the end, simple.

“Like what?” Maria said now turning on her teen whore charm and stepping closer into Zack’s space.

“Submit to me. Suck my cock and we will call that a deep throating and toss in anal, even if we don’t do it. I bet my dad would even take you for a date later, I can ask. He’s good for extras too.” Zack said though he had no idea if his dad was interested.

Maria smiled for the first time. They shook hands and she stepped into his personal space lifting her face to his.

“You want to kiss the head cheerleader then go ahead,” Maria said as she opened her mouth to his.

They kissed as his cock sprung up between them. His hands went right to her breasts lifting her heavy tits, squeezing them. Fulfilling a dream to put his hands on her boobs. Maria’s mouth was warm and wet, and she moaned as his hands pulled at her breasts. They broke the kiss after a couple of minutes, and he pushed her to her knees.

On her knees, Maria held his cock in her hand pulling at him not looking up at him concentrating on his cock and hairy balls.

“Do you like sex?” Zack asked, just for conversation.

Maria looked up at him. “It’s a thing, I have to do it. Sometimes I like it, sometimes I don’t.” She took his cockhead in her mouth as he put both his hands on her head. She began to take him deeper in her warm wet mouth.

He made the cheerleader submit to his needs. He had probably watched too many videos of other Brothel Nights and the debauched sex that took place. He wanted to do a lot of things to Maria, but he only had an hour. They went to the 69 position with Maria on top after she took off her lingerie in a sexy little dance for him while shaking her boobs in his face. He ate out her bald pussy sucking and using his tongue until she orgasmed with his cock in her mouth. They had sex in the missionary position, and he came for the first time on her tits. He played with her asshole fingering her as she lay there talking with him.

They had sex again after she sucked his cock back to life. Maria was on top and more willing as he explored her asshole with his fingers, she seemed to like it. She let him spank her after he came inside her just before the Madam called time on the date. He left his mark and Maria knew his name now. He liked her and they had an understanding, she would say ‘hi’ the next time they met at school.

Zack reflected on another of his dad’s pieces of advice, something he had said to him when he turned fifteen. Sex was sex, his dad said, don’t confuse it with love. Something he still found confusing at times but was already putting to practice tonight starting with the oh-so-distant and previously untouchable cheerleader.

The girls with long hair had it tied in ponytails or braids. Most had a light dusting of makeup covering up a teen imperfection and accenting a beauty point. Their mothers would not have sent them here otherwise to be seen by the men. Hair tied back and good makeup were better for their work and being seen on an HD video system that would record their every move in the smallest detail.

Some girls wore strappy bralettes with sheer panels, many were in cage-style body harnesses that left all their tits hanging out along with a few cupless and ¼ cup bras and the like. Most all the teens wore crotchless panties of some type of various colors from black to bright pink while a couple went bold with a small thong and garter belt with stockings.

The girls all chose styles that accented their boobs, nipples, and crotches for the men to enjoy and run the occasional hand over. A few girls were dressed more conservatively with sheer panels over breasts and crotch, doing a little more to hide their nipples or pussy. Most complimented their skimpy lingerie with some type of micro purse strung over their shoulder to carry their device or things like extra stim patches or lotion. While each girl wore a slender biometric band on her wrist. Before attending the girls all had attended a two-hour seminar on ‘how to be a Saint-U escort’.

Olivia

Done with Maria and after a quick wash of his dick, he was back in the bar area watching the girls come back in from ‘dates’ or waiting to be chosen. He drank a fresh beer and considered the list of girls on his device’s open brothel app. Comparing what he saw with the list of available ‘escorts’. He needed to rest for a little while and wanted to see if Hannah or his dad would come down.

Soon, Hannah’s friend Olivia, a pretty olive-skinned teen with long black hair was walking in his direction topless, her hair and makeup a mess. Olivia’s tiny black thong was crotchless so he could see the trimmed patch of dark hair from ten paces away as she came to him holding a glass of red wine. Tonight, even fourteen-year-old girls like Olivia were encouraged to drink or take whatever pill they needed to get through the long night of debauchery.

“Hey Zack, can I join you?” she said, slightly slurring her words as she plopped down on the cushioned loveseat across from him.

Where Hannah, his reference point for a lot of girls, had a small, barely developed chest. Olivia already had nice firm conical breasts topped with dark puffy nipples on her short compact body. She was a scholarship kid at their school, being raised by her widowed Mom. Zack would try to keep a protective eye on her, he told Hannah, even as he felt his cock reacting to her exotic nudity.

“How was your date?” he said, pulling his eyes from her chest to her dark brown eyes. ‘Date’ a long-understood code word for a meeting between a prostitute and a client. Tonight, she was a whore, and he was a paying client, or technically his dad was.

“Good, Mr. Burns tipped for a couple of extras so that was nice.” Her cheeks reddened a bit as she said that. Perhaps the alcohol loosened her lips as she spoke the truth.

The half-hour or hour dates all had a fixed rate just like a real brothel. Where the girls could earn extra was on tips for doing things like deep throating, ass play, and other things that were listed in the tip section in the app. Even getting fucked while passed out earned a sizable tip. Some men’s fantasy.

“You mean the Assistant Dean?” Mr. Burns was in his 60s, a bit of a paunch on him but everyone at the private school seemed to like him. His much younger wife was a science teacher at the school. She was around here somewhere helping to keep things running efficiently.

“Is there another? Yes him. He is nice but kinky. You’ll have to watch our feed once it’s posted.” Olivia said her eyes on Zack.

She was referring to a webpage that Holy Saint Ursula Preparatory maintained. Brothel Nights digitally recorded what happened in each room. Along with maintaining the profiles of past and current girls. Everything was encrypted and kept on a very secure server with access limited to past participants and those like Zack’s dad who had provided some of the funding.

Once Zack had found out from his dad about the school’s trove of brothel videos going back a couple of years, he had spent hours masturbating to some really wild stuff. He came to Brothel Night filled with ideas.

While he and Olivia were making small talk, he was watching the boobs and assess of the lingerie-clad girls stopping by the lounge and bar to drum up business, grab a drink or just say hello to friends. It was odd seeing girls, some of them his classmates who earlier in the day had been in their conservative green and white school uniforms. Now the same girls, mostly naked walking right past him, a few giving him a knowing smile.

He smiled at a couple of volleyball players. He saw AD Burns’ niece who was a blonde tennis player and the cute Bianca sisters, honor students, exchange students, and quiet shy teens who were here just to be accepted. Some girls were clearly awkward teenagers just old enough to be here. While on the other end of the scale were girls like Maria whose bodies were closer to full womanhood.

The first hour had just ended when all the auctioned girls had been fucked. A few girls were already starting a second date. About a dozen men now sat in the area drinking and socializing with the girls who were also drinking and working the room. Most clients knew how to pace themselves and to wait for the girls they wanted.

Now that the second hour was starting, the ‘clients’ had to make their date requests via the SU-Brothel app. The menu consisted of skinny little blondes like Hannah to fully developed seventeen- and eighteen-year-olds, like Maria, who physically were ready for adulthood and everything in between on the development and looks scale.

It was truly a beautiful sight to see all the young flesh walking around. Big boobs, small, tall thin girls, and stocky short girls, blonde, brunettes, and redheads. There was something for all the men’s tastes, girls of Asian and Native American descent and even a couple of pretty light-skinned black sisters (real sisters) participating tonight mixed in with all the others. A true multicultural experience for the most part.

He continued to study the app as he sat with Olivia. As this was a Saint-U event there was not an unattractive girl among them, though not all were beauties. Over the last week Zack had studied the girl’s profiles and short-listed a half dozen girls he would try and ‘date’ if he could.

In the first hour of the event, all the ‘clients’ had silently bid on the girls as they enjoyed the buffet. Hannah’s mom Mrs. Strong or Lisa to him was the master of ceremonies as the volunteer chairwoman for the event. Dressed in a black sheer mesh chemise that showed off a lot and hid little of her trim womanly figure, she had done a great job making sure bids kept coming during the hour of the silent auction. Someone even asked to bid on her, but she politely declined with a smile.

The men ate catered BBQ ribs and chicken as they watched the stage show while the girls were introduced. The teens playfully flashed their boobs, shook their asses, and did little dances to entice and attract a winning bid. With only about fifteen rooms and spaces converted for use as bedrooms not every girl would be sold tonight for the first hour and not every man would come away with an auction date. It would be a pricy endeavor to get the girl you wanted, and the bidding was not for the faint of heart.

He had fun watching as girls worked the crowd to up the bids. During the show, his father kept tapping away on his device increasing bids on the four girls they shortlisted, two of Zack’s and two of his own. Brock had snagged snooty busty Maria at the very end for Zack. Brock got himself a freshman volleyball player who had just turned fourteen. Maria’s fake smile had been priceless when she realized it was Zack, not his dad who was her date.

Turning his attention back on Olivia, “So what did Mr. Burns do with you?” He could pull up the video next week, but it was better to hear from Olivia herself.

She drank the last of her red wine before answering. “You want to hear this stuff?” Olivia said, watching him.

“Yeah, go ahead and if you want, I’ll tell you about Maria.” He replied.

“Okay. Well, before he took me doggy with that cubby dick of his I had to eat his ass and suck his balls. Balls were included. Ass work is extra.” Said before her device chirped. A message appeared on her device. A room number and the time paid for, client ID number. ‘2B. ½. 13’

Hannah was currently in 2C, he knew.

“Well, that was mostly what we did. It looks like I have a half-hour date with ‘client’ 13.” Olivia sighed.

He nodded seeing the information on the device.

“Zack, would you give me a hand? Put this stim patch on me.” She held up a small skin-colored patch that he just needed to peel the backing off of.

“You’re hitting the stim juice early,” he said not judging, just wondering.

“It helps with my sensitivity levels. I can really feel everything when the juice from the patch is flowing.”

She took a scrunchy from her small purse and tied her messy long hair back while he found a spot just above her left shoulder blade. The patch blended in with her skin as he smoothed it down, making it difficult to see unless you were looking closely.

“Thank you and thanks for keeping an eye out for me tonight. Hannah told me you were going to.”

“No problem. Send me a message if you need me,” he said putting a hand on her ass as she turned to leave.

She smiled at him. Her eyes lingering on him for a moment before turning her attention to her next date.

Olivia looked at the podium by the stairs. An older redheaded woman the acting house Madam dressed in the same black sheer mesh chemise as Lisa waved at her.

“Do you know who he is?” Zack asked.

“Nah, after the auction, it’s all a secret on which ‘client’ puts in the request. We don’t know who our ‘date’ is until they walk in the room.” She said. “Adds a bit of a thrill, the wait.”

Zack understood. No chance for a girl to try and back out either.

Olivia kissed him on the cheek and gave him a little wiggle of her ass as he watched the topless fourteen-year-old stop by the Madam before heading upstairs. On his device, he saw her name on the app go from green to red. There was no electronic queuing for a girl as she was either available or not. He was told that this way business kept flowing.

He shouldn’t waste the evening talking to friends, so he started checking the Brothel app in earnest to see who was available. His game plan was to try and fuck the girls who wouldn’t accept a ‘sex date’ outside of Brothel Night from him. A dorky fifteen-year-old who played baseball and designed hybrid role-playing games, he wasn’t super popular with the ladies yet. Here they couldn’t turn down a paying client for any reason short of a personal health emergency.

A message from his dad popped up. ’Just finished with Sonya. Coming down for a drink.’

Sonya was just barely legal in Tennessee as according to her profile she just turned fourteen the month before.

He knew she was new to the school, a tall athletic brunette with a sweet smile who played volleyball on the freshman squad. He had seen her around campus.

Another video he would have to watch later with a bottle of lotion.

’Maria was good. I’m looking for my next date. Just finished my beer after talking with Olivia.’ He messaged back, more details than his dad probably needed.

New Girl

Hmm, on his favorites list, he saw one of the girls go from red to green.

Danika Van Winter. Theatre and Latin clubs. Her life’s goal was to join the SpaceX-NASA Mars mission. Good luck with that! Danika was a reddish blonde with a perfect ass. At sixteen she was always hanging out with the theatre dorks and never spoke with him, ever. He had not seen much in her ‘sex date’ profile, just one or two references when he looked. So, a quick tap on the app to request a half-hour date, the standard length of a date.

Bing, accepted by the Madam. Danika would get no rest between clients. 2A was the next message. Her name went from green to red.

At the bottom of the stairs, he ran into his dad. Brock wearing his short gray kimono and sandals was just coming down. They fist-bumped in passing and kept on going knowing they each had business to attend to.

A few steps behind his dad he was surprised to see Hannah walking slowly down the steps, swaying a little bracing herself on the wooden staircase’s handrail. She was completely naked except for the sandals on her feet. Her makeup was smeared, and blonde hair spilled out of her once tight ponytail. As he got closer, he saw what looked like drying cum in her hair and on her chest.

She tried to steady herself by holding onto the banister then smiled when she saw her best guy friend reaching out for her.

“You okay?” he said with a concerned voice taking in the ‘damage’ as he reached a hand out to her. Yup cum in hair and on her chest, mascara a mess. She still had her small clutch purse in hand, which was good.

“Oh, hi Zack.” She stopped at the bottom of the stairs, holding the banister. “My client Mr. Abrams the Rabbi guy was a little rough but fun.” She must have seen the worried look on his face.

“Don’t worry I just need a stim patch and drink and I’ll be ready for the next. The fun life of a Saint-U call girl, right,” she said with a weak smile.

He was tempted to stop and hug her. Instead, Zack reached out and ran a hand over one of her small, perky, cum-covered breasts.

“Yeah, he was a shooter, fucker went everywhere. I need to give myself a quick wash before I go up again.”

“Do that, I am heading up to Danika in 2A. I’ll see you at the bar later.”

“Ohh, the stuck-up drama girl with the ass you like.” She smiled getting her feet back under herself now. “I see the Madam waving at me, so I better get moving.”

They headed in opposite directions. The good news is that Hannah just finished her auction date. Again, he thought, why did he care how many dates she had done? They would both fuck a lot of new partners by the end of the night.

For a moment he watched her walk to the Madam’s podium and saw she had a heck of a fiery red mark on her ass, the size of a big man’s hand.

He smiled to himself as he went up the stairs to 2A. He knew of Mr. Abram’s daughter Rebekah she acted like the quintessential stuck-up JAP – Jewish American Princess. Her sex date profile said she only wanted to fuck older men and while at school she was always studying in the library with other ‘Princesses’. Definitely on his list for tonight. Mr. Abrams was a friend of his dad’s and the local Reform Rabbi, a strong-looking bearded man, a veteran of the IDF’s wars protecting Israel. He had commanded a company of paratroopers in Gaza during the Israel-Hamas war after October 7^th, so he had heard from his dad.

“Hello Mrs. Burns,” Zack said spying the 40something willowy dark-haired science teacher in the second-floor hallway. Her figure was wrapped in the same sheer piece of lacy fabric as the other women, giving him a nice look at her perfectly round breasts with the small hard nips poking at the fabric. He was surprised to see small gold bars in each of her nipples. She was carrying a wicker basket of fresh towels and sheets heading in the same direction.

She smiled when she saw his eyes pause at her chest. “Like them? Mr. Burns paid for these when I hit the 40 last year, gave my girls a bump in size, firmed ‘em up too.”

Zack had stopped a few steps from 2A. Mrs. Burns and her basket between the two of them.

“Give them a feel, go ahead,” she leaned toward him.

He reached across and cupped each with both hands then thumbed each nipple. They were perfectly round and soft even through the thin mesh fabric. They did feel great, firm no hint she had work done. Not that he had any experience with breast implants. It felt strange to feel the nipple piercings, the contrast between the hard metal and soft flesh was new to him.

“Wow, I love them. I’m sure Mr. Burns does too.” He said in the way of a compliment.

She smiled. Instead of replying she leaned even closer and lowered her voice. “Be gentle with Danika, will you? That sweet girl had a tough one, rode her real hard. Word is you are a pretty sensitive guy, go easy for a bit. She’s worth it.”

He just nodded as she stepped to the side moving her basket out of the way so he could pass. Damn, why did she have to say that? The plan for his cock was to own the snooty drama girl.

He stood at the open doorway to room 2A and knocked once on the empty door frame. Danika stood with her back to him in the center of the room. From behind, he saw she still wore her dark blue strappy bralette the small thong riding up her perfectly shaped white ass. He was surprised she hadn’t just stayed naked, like Hannah. Now he would get to unwrap her, like a present.

From behind, he admired her tight firm looking ass, the flawless appearance of her pink skin, and the way her reddish blonde hair fell easily just below her shoulders. He was not certain, but he thought she might have been crying from the way she held her hands up to her face. Zack realized he had not cared about her feelings until Mrs. Burns poked at his kind empathetic nature. Yeah, maybe he had watched too many videos over the last two weeks where ‘clients’ just went in and had their way no matter what with the girl.

What had his dad said, get to know their motivation. Maybe. He was horny again. Danika had consented when she signed up. His motivation was to fuck the second girl he had on his short list and have fun.

He just wanted to own her, make her do what he wanted, that was the deal for tonight he thought. Like he had put Maria the cheerleader on her knees in front of his dick after a short conversation.

Zack, like all the male guests, wore a short gray dressing gown-style silk kimono belted at the waist. A party gift from his dad’s company for all the men this evening.

“Hello Danika, I’m your date,” he said as he moved toward the bed that dominated the small room. A fresh white sheet covered the bed, Mrs. Burns’ work.

Danika’s strawberry blonde head turned to look over her shoulder, seeing him she turned to face him. Wow! Her large round breasts were held up by a sheer strappy bralette while she held herself with the poise of a dancer, head up and back straight she covered her chest with her arms on seeing him, another teenager. She was on the tall side, about 5’6 almost his eye level.