A story in the sex date universe of stories. Updated and edited for clarity May 2024.

This story takes place in a universe created by EazinAlong where parents set up sex dates for their teens. Pretty simple concept. I consulted with EazinAlong about the story and he reviewed it, though all punctuation errors etc. are mine alone.

In this story, a neighbor boy Zack has a sex date with his best friend Hannah.

Nashville – 2029

Zack caught himself staring out his bedroom window late in the afternoon. His neighbor Hannah had just stepped out of her mom’s Range Rover in a short white tennis skirt showing off a lot of tan leg. Hannah grabbed her tennis bag from the back and headed up the driveway to her house. Zack enjoyed watching the skinny blonde-haired girl with a cute smile as she pranced up the driveway. On the steps before the front door, she suddenly paused and looked back across the cul-de-sac at Zack’s house.

He was not sure if she saw him, but it did not matter as she was marching down her driveway toward his house. Her mom said something, but Hannah just waved her off as she went inside grabbing Hannah’s tennis bag as she went.

The front doorbell rang as Zack was still crossing the living room. Before he could get to the door it opened and she walked in. Hannah smiled but he could see by the look on her face she was upset. They all lived in a private gated Nashville neighborhood and rarely locked their front doors plus they had known each other most of their young lives. Hannah was fourteen and he was fifteen, he was a sophomore, and she was a freshman at Saint Ursala Catholic High School.

Zack kept quiet as she stood before him, her small chest rising as she took a deep breath and then again before she spoke. Her white tennis dress was sleeveless showing off her tan shoulders and toned athletic arms. She had a slim pink smartwatch on her left wrist and her blonde hair was cut fashionably short. They were at that age when girls were spurting up but not fully out with breasts yet, she stood at just over 5-foot almost eye to eye. The look on her face showed anger and he saw fresh tears on her cheeks. He opened his arms to her.

Her body felt nice in his embrace, but then she always did when they had such a moment. Hannah had seemed a bit different the last couple of weeks. More self-assured about herself a little wiser perhaps. He had noticed but was not sure why. Today she was acting the opposite.

“You want to tell me?”, he said as he released her taking both her hands in his and pulling her towards a couch. He sat her on one end and then went to the kitchen to get her a drink while she talked.

“I just had a bad afternoon, I ran into someone I thought was a friend, and well he ignored me,” she said looking at her hands and then over at the dark TV screen on the wall.

“How can I help?” he said from the kitchen as he poured two cold glasses of lemonade.

Zack returned to the room handing her a lemonade while she sat lost in thought. He just sat next to her waiting sipping his drink.

“Emma, start the hot tub,” Hannah said to the room, knowing her voice was keyed into Zack’s ‘smart home’ system.

“Let’s go soak in the hot water and I am sure I will feel better.” Now looking him straight in the eyes, “Plus I want to ask you something.”

They moved to the back of the house towards the backyard where a large hot tub was located. Once outside on the wood deck that held the tub of now swirling bubbling hot water, they paused in unison by a wooden bench. Without looking at each other they began to strip. Hannah turned her back to Zack and he just pulled down her zipper far enough so she could shrug off her tennis dress letting it fall to her feet. Today she had on tight spandex shorts underneath cupping her small firm ass. She had been playing tennis for a year and had a nice fit look to her skinny figure. As she turned to face him, he enjoyed the sight of her small budding breasts with their puffy pink nipples the size of dimes.

Zack pulled his t-shirt over his head and then dropped his sweatpants while she pushed down her spandex shorts to her ankles while turning away from him. It was a game they had started playing a while ago called ‘getting a peek’. He did the same turning away as he dropped his boxer shorts to his feet. He was barefoot and she stood a couple of feet away and kicked off her tennis shoes with practiced ease followed by her sweaty spandex into the small pile of clothes between them.

Now she started to act her goofy self as she put one hand on her small ass as if to cover it while keeping the other over her chest as she looked over her shoulder at him. Then she quickly switched hands again as if undecided. Zack stood in front of her one hand over his groin hiding a slowly growing cock watching her antics.

They had been using the sauna and soaking nude together in the hot tub since he and his father returned from living in Germany last Fall. At the time he had explained German sauna culture and that if she wanted to use their new sauna, which was in a wood building next to the hot tub, she had to do it like the Europeans, no clothes. It did not take much convincing, just a VR (virtual reality) video to prove the truth of his claim and they were soon naked together.

Zack watched as Hannah tested the water with a toe then slid in oohing and ahhing as her body adjusted to the hot water and came to rest against an underwater jet. Zack did the same though pulling his hand away as he slid in letting her see his semi-hard dick rising out of a dark patch of pubic hair. Now after several months nude of bathing together, he was seldom embarrassed with her.

They sat across from one another while underwater their legs and feet playfully touched, finding comfort in the moment. He watched Hannah as she took time to collect her thoughts. She had told him once that he was the most empathetic boy she knew. He had said the same of her. The water did feel good. He looked at her chest seeing her dime-sized pink nipples just visible through the bubbling water. When they had started getting naked together, her chest was flat, just puffy nipples and she was shy but now several months later she had small budding breasts that he often thought about and today she was less shy. He could tell she was searching for words that she had something important to share.

Before she spoke, he reflected on how important she had become to him, a connection to home while he had lived in Berlin for two years with his family. In the middle of his dad’s assignment, a short war brutal war broke out in Poland, now known as ‘The 12-Day War’. He was mostly alone in Berlin with his mom and sister having moved to Vienna so Heidi could study music at the conservatory.

Seeking to punish Poland for their perceived support for Ukraine in their fight against the illegal war launched against them in February 2022, Russia launched a surprise attack in July 2028. His dad was a Major in the Army Reserve and had arranged to do his reserve duty in Poznan at the V Corps Headquarters. When the war started, he raced from Berlin to Poznan and was soon in combat.

Berlin had been hit by Russian missiles mostly to intimidate Germany into inaction, which was mostly successful until Poland and the US Army turned the tide outside of Warsaw. Zack felt the explosions and heard the air defense batteries shooting back. One night debris from an attack landed in a park outside his apartment building in a ball of fire. At the time Hannah was his link to back home as they talked on their devices late into the night. Hannah and his dad’s favorite escort Eva kept him sane and calm.

In the hot tub, his right foot had pried open her skinny thighs and now his feet were resting in her lap when she spoke.

“Ask your dad to call my mom and tell her you want a date with me,” she said in a serious voice.

He had not seen her looking this serious in some time, not since her cat died two months previous. They did things all the time together so was confused by the word ‘date’. Was she suddenly interested in him? He was not sure how he felt. But he would do as she asked. They had playdates when they were in elementary school but had not had such a planned meeting since he moved back in the Fall when his dad became COO of Pegasus Group. Teenagers didn’t have ‘play dates’ set up by their parents.

“Okay, I will but when will you tell me what is bothering you?” Zack said.

“I promise after our date you will understand, and I will tell you why,” she said now with a shy smile.

Changing the subject, they talked about her tennis and his baseball preseason, and the fantasy role-playing games he was playing and designing.

The message from his dad asked him to be home this evening. He did not elaborate. Zack was upstairs working on the next storyline for an upcoming Advanced Dungeons & Dragons game he was running when his father’s Mercedes SUV pulled into the driveway. He had a couple of bags of take-out food with him when he came in the front door.

They shared the Thai food sitting in the living room in front of the TV where they caught up on the latest in world news. Zack did not ask his dad why he asked him to stay home this evening. Perhaps it had something to do with Hannah’s mysterious request just yesterday. That same night his dad had done as Zack asked but instead of calling, he had walked across the street to talk with Hannah’s Mom. He was gone a long time then disappeared into his office closing the door.

Now with dinner finished they were sitting together, both dressed casually in Addidas track suits in the office in front of his dad’s personal computer. His father had a nice 50” 8K VR-enabled terminal. Brock brought two gin and tonics with him handing one to Zack.

His Father could be rather direct. As a former military man, though still in the reserves, he was used to just getting right to the point.

“So, I had a long talk with Hannah’s Mom Lisa yesterday as you know. I learned a lot about our small community. Our country has changed a lot in the last few years and with us being in Germany for two years we did not keep as up-to-date as we should have on what was happening. What I am about to talk about with you would have been handled by your mother.” He said.

Zack just nodded as his dad talked and entered some commands into his keyboard.

“While we were living in Berlin you and I got used to using an escort service to provide a girl when we had an itch to scratch,” his dad’s old-fashioned way of saying needing sex, “but over here things were moving in a different direction.”

Zack continued to nod, his mind thinking of the cute Estonian escort Eva, whom he and his father shared and who was his first sexual experience when he was fourteen, his first blow job and putting his hands on a girl’s breasts, hers were fantastic. On his 15^th birthday, he lost his virginity to Eva, a gift from his dad. She now worked for his dad’s company here in Nashville and was his dad’s regular companion.

He continued, “Lisa let me know that parents in the last few years began organizing sex hookups or dates for their teens to encourage them to have good sex and improve sexual knowledge. There is a huge new philosophy behind all this, but I’ll skip that for now. I guess we came back to the US at the right time.” He said with a grin.

“So how does that work?” Zack said,” And how does Hannah fit into all this?” Hannah’s request for the ‘date’ now made a little more sense but he wanted to hear it from his dad.

“That is why I have the computer on. There is a private cloud server for the participants and their families. Lisa gave me a temporary passcode,” he said then entered a code into a box on an open browser page, Saint-U Community Dating. Enter Pass Code.

Zack watched as a blonde face he knew well appeared on the screen. They both put on wire-rimmed VR assist glasses. Now, her face was way more present and had depth and lifelike clarity. The familiar short bob of her blonde hair and her smile in a headshot. The frame was frozen while Zack and his dad pushed themselves back from the screen to a more comfortable distance.

“I’ll warn you. You will see Hannah in a new way after this video. Lisa also provided me with some clips from their family’s private cloud server.”

“Okay Dad.” he said a bit apprehensive but also keenly interested in the screen with his friends’ image.”

Zack sat back as a smiling Hannah introduced herself. Just a close-up of her face as she talked about herself, her age (14), hobbies, and the music she liked, until the video pulled back revealing Hannah sitting naked on the edge of her bed her skinny legs crossed as she held her favorite teddy bear in her lap. Her chest was not her biggest asset, that was her pretty face and personality. Her breasts were the small pink buds he was used to, her cheeks were flush, and red, like someone had pinched them or highlighted them with blush. Hannah said she was a virgin and wanted to become better at sex and have as many partners as she could in her first-year Sex Dating.

She was asked what type of boy was her ideal sex date. She thought for a moment glancing at a photograph on her nightstand.

“My ideal guy, well he would be like a friend of mine who lives nearby. He would be smart, a bit of a dork, but also athletic, and funny. He would like to do things for me. I think a boy like him would be a good lover. At least until I learn more. But really any boy with a nice cock,” She answered a combination of truth and naughty, her blue eyes looking into the camera giving it one last smile and a little wave with her right hand.

Watching his best girlfriend sitting naked on her bed talking about ‘sex dating’ had got his cock hard. As a short introduction, it was effective. Got to know a little about her, saw her naked, goodbye.

This first video was short, unsurprisingly his cock reacted to Hannah seeing her in a sexy pose and her talk about sex. On the TV and his VR glasses, the video transitioned to the same bedroom, but she was with a teenage boy. He didn’t know the guy, but he was in good shape, an athlete, and older by a couple of years he guessed. The date imprinted in a corner was only two weeks ago.

He checked his emotions, and he was more fascinated than anything, if he felt jealousy, it was that he wanted to be in the boy’s place.

“We are watching outtakes from Lisa’s in-home camera system, she wanted you to see Hannah, to see her on her first Sex Date, and to understand what a sex date is like.” His dad said as he handed him a bottle of lotion.

He did not have to ask why his dad handed him the lotion.

The video continued cutting to different scenes of the older boy kissing Hannah, stripping her, her small budding breasts being kissed and teased and on her back as the boy slowly entered her virgin pussy. The boy had to slow down but then Hannah’s moans and commands for more were urgent a bit over the top as she tossed her short blonde hair around as she lay on her back pulling his down. Watching her have sex he found his pulse racing as stroked his cock.

Zack reached for the keyboard and typed in new commands and the scene twisted and zoomed to get close-ups of the sex, balls slapping Hannah’s small cunt then over her slender chest finished in the god view from above the bed. For the next 15 minutes, he and his father watched young Hannah being fucked by the boy and even a quick scene as she buried her face in her mom’s wet pussy.

When the video ended, Zack sat a bit stunned or confused. His cock was hard and somewhere during the viewing he had pushed his sweatpants down and he had started jacking his lotion-covered cock with his right fist.

Taking off his glasses he saw his dad was also in an excited state with his hand around his long thick shaft.

“As you can see an interesting program this new ‘sex dating’ project. I wish it had been around when I was your age. I had to work for it, and find girls who were willing to give it up.” Brock said.

Zack just nodded his head still processing. The images of Hannah having sex with a stranger still fresh.

“You and I have a date with Hannah and her mom tomorrow, so don’t stay up too late.” His dad said as he stood pulling his sweatpants up over his stiff cock.

“Hello, hello,” a young woman’s voice rang out from the front of the house.

Zack recognized the softly accented voice of Eva, his dad’s former escort and now company employee. He smiled, she was great, a cute short dirty blonde from Estonia with perfectly sized conical tits for her small compact body. She was also a very kind person.

“I’ll be right out,” his dad said pulling up his sweatpants.

“Feel free to join us in the sauna if you like,” he said to Zack as he headed for the door.

“If it’s okay with you, I think I’ll look at a couple more of Hannah’s family videos and then come out for a soak?” With that, he gave commands to Emma, the house AI, to start the hot tub and warm up the sauna for his dad and Eva. His Dad enjoyed his time with Eva every Friday evening; she had become like an older sister to him over the last year.

He thought about calling Hannah but decided not to say or do anything for the moment as his thoughts went to all the things he and Hannah might do together. But still, why did she ask for him now? And when could he look at all the other date videos? He smiled to himself and typed in commands bringing up the long version of the date video while adjusting his hand in his lap. Twenty minutes later, he felt satisfied and a little disturbed, as he tossed a wad of Kleenex in the toilet bowl. He took off his tracksuit and headed out to the hot tub to join Eva and his dad.

Zack was up early on Saturday for preseason baseball practice at Saint-U. His dad picked him up at noon and they swung through the Chick-fil-A drive-through on the way home. They didn’t talk about the upcoming Sex Date just baseball and other weekend plans.

After he finished his chicken sandwich and Dr. Pepper, he took a shower and brushed his teeth. He checked himself in the mirror and trimmed his pubes, his nails were cut and clean. A little pump of Polo cologne. Zack looked good, he thought. At 1 o’clock they walked across the cul-de-sac to Hannah’s house. They had both dressed casually in chinos and polo shirts. His Dad carried a bottle of red wine from the Napa region and Zack held a box of dark chocolates along with a single red rose. Eva’s touch, she left the flower on his computer desk with a nice note for him.

They met Hannah’s dad Jack and younger sister Alice in the driveway as he loaded golf bags into the back of his Audi SUV. They all shook hands.

“You two have fun. Alice and I are off to the Country Club for the afternoon. We’re doing a father-daughter golf date, so the house is yours.” Jack said, as if super normal he was leaving his wife and daughter alone for an afternoon of fucking with his neighbors.

“We appreciate being invited to use your house for Zack’s sex date with Hannah,” Brock replied.

“Brock, you know my family is your family, have a great time with Lisa and Hannah,” he said with a straight knowing face.

Zack watched the exchange between the two men. He had noticed since returning from Germany and his dad’s war service, that men were more deferential to his dad, other men seemed to want to please his dad and stay on his good side.

Alice was younger by a year and dark whereas Hannah was light-complected. Alice had long brown hair and already a big developed bust on thick athletic legs. She did not even look at Zack as she got in the passenger seat of the SUV.

“Jack, I appreciate the thought,” said Brock as they headed to the front door. The Audi backed out of the driveway behind them.

They met Lisa at the open front door. Like the men, she dressed casually in khaki shorts and a short-sleeved diaphanous blouse of fine white fabric. The pink nipples of her round breasts pressed firmly against the tight material. Zack had never seen Hannah’s mom’s naked tits before. Lisa was blonde and fair-skinned like Hannah with the trim figure of a woman who did yoga 4 days a week and ate healthy foods. Her curly blonde hair fell loosely on her shoulders framing a welcoming intelligent smile.

“Welcome Brock, Zack, let’s go to the living room. Hannah is upstairs and will be down shortly,” she said leading the way.

In the large living room, the two of them sat on a comfortable leather couch in front of an entertainment system while Lisa took the bottle of wine from Brock and went to the kitchen.

Speaking from the kitchen, “I thought we would start off by showing you the promo video for the upcoming Saint-U Prep Brothel Night fundraiser and a little something our family filmed last weekend,” Lisa said.

Zack and his dad both nodded sitting side by side on the couch. To the left of the wall-mounted TV were the stairs that led up to the bedrooms on the upper floor and Zack kept an eye on them anticipating his friend Hannah.

Using verbal commands, Lisa lowered the window shades darkening the room as the screen came to life in front of them.

Zack had not heard of this Brothel Night event and a sideways look at his dad’s smiling face said he probably had. As the video started a woman’s voice narrated over an aerial view of a large country estate while a couple of electric passenger buses arrived dropping off men at the front of the palatial ranch-style home.

The voice-over introduced the Brothel Night 2029 Spring event, talking about the fundraising aspect of the evening including the school scholarship and relief funds. The video cut to inside where casually dressed men stood around taking drinks from and talking with scantily clad young teen girls who circulated through the small crowd of men. From the look of it, people appeared to know each other, and a festive atmosphere permeated the room.

The video cut to show the bedrooms showing the luxury of the individual rooms, one with a hot tub, others with sex toys, and a massage table. Back in the main room, the video showed an ongoing auction of young girls as people raised their voices bidding as the partially nude teenage girls were led on stage. The girls all looked happy, they were smiling, laughing showing themselves in erotic playful ways as they tried to raise the bids higher. Zack thought he recognized the faces of a couple of girls from his private high school.

The woman continued to narrate the video as the scene switched to girls being led to private rooms by their winning bidders. The voice said this auction was for the first hour after which each girl had a fixed price for her time. Hence ‘Brothel Night’. It was for charity as all the young girls were still learning about sex and looking for older patrons. Various scenes showed girls undressing with their ‘client’ and then descending into various sexual acts as the camera cut from room to room and then back to the main room.

Attractive girls who wore very little clothing circulated through the tables offering drinks and lap company as the men were watching screens live fed from various rooms or just shooting pool in the billiard room. Men would tap on their devices, choose a girl, then head upstairs to meet their ‘date’. The teenage girls were from Saint-U and were ‘working’ at the brothel for charity. The video ended by giving the date and contact information to request an invitation to the exclusive event. The Brothel Night weekend was only a month away.

From the kitchen, Lisa spoke up “That scenes in the video are from the Fall event. Hannah will be participating this year. I’m the Chairwoman of the organizing committee this year. I’m so happy that Pegasus Group is underwriting the Spring event. Zack, Brothel Night is for charity, raising funds for the school’s scholarship kids, her voice soft and sweet as she entered the room with a tray holding three glasses of wine along with cheese and crackers.

Zack watched his dad as the room lights came up, he appeared deep in thought before reaching for a glass of red wine. Lisa sat in a comfortable matching chair to their left.

“Yes, I know, Pegasus Group was approached about sponsoring the Spring event and I approved it, with conditions,” Brock said.

“Yes, I heard, our last sponsor pulled out, cold feet or the price was too high, or both, so thank you,” Lisa said.

“How often do you hold these events?” Brock asked for Zack’s benefit, he knew the answer as he had inked the deal for the next two Brothel Nights, with conditions.

“They are held three times a year Fall, Spring, and for the first time a summer pool party this year. Hannah’s Dad has been a patron since Hannah was a freshman and he became eligible to attend as the dad of a student enrolled at Saint-U.” Lisa answered matter of fact.

She continued, “Now don’t think that the men get all the fun, the ladies have a couple of their own smaller events,” she said turning an eye to Zack and giving a slight wink with her smile.

“But let me start the second video then I’ll invite Hannah down.”

“Hannah had her first date two weeks ago,” Lisa said. “My husband had always wanted to be the first ‘adult’ to shoot a load of cum on Hannah’s face, but we wanted to wait for the right moment. Last weekend, after her first date, he and Hannah had some fun together. For your viewing pleasure, here is a short clip.” This time Lisa handed each of them a pair of wireframe VR glasses before she headed up the stairs.

Inside, Zack felt a bit shocked to hear this frank talk from Mrs. Strong about his platonic friend Hannah and her dad, but at the same time, his cock was twitching in his pants in anticipation.

Setting the glasses on his face he took a sip of his Cabernet. He was still learning about wine, but it wasn’t bad. On the screen and in his VR glasses a scene started to unfold with a nude Hannah in her parents’ large master bedroom. Lisa was lying naked on the bed while at the foot of the bed stood Hanna’s dad. Of medium height, a little belly, but golfer fit, a dad bod, clean shaven with a nice haircut. Her mom looked good.

Hannah, naked, entered the room and presented herself to her dad, stopping in front of him. Over the next few minutes, Zack watched as Hannah knelt and took her dad’s cock in her small hands and worked at his shaft with her mouth and tongue until he was hard. Her mom encouraged Hannah from the bed while she played with a small pink vibrator on her pussy lips.

Zack’s heart melted a bit when Hannah looked up with her big eyes at her dad, on her knees holding his large ball sack in her small hands his long hard cock pressing deep into her gaping mouth as he started to rock his hips then held her blonde head still with his hands. Zack could see Hannah fighting off her gag reflex as her dad shot two streams of milky white cum into her mouth.

The corners of her eyes began to tear up as she held on, one hand reaching around for her dad’s hairy ass and the other the shaft, white cum on the corners of her wet red lips. Suddenly he let go of her head and stepped back allowing his daughter to swallow and breathe again. White cum dripped down her chin as she reached up with the back of a hand to wipe her lips smiling at her dad. Hannah stood as her dad embraced her as her smiling mom clapped proudly from the bed. Turning she presented her small, cute ass to one of the room’s cameras before she jumped on the bed joining her mom, falling into her arms for a cuddle. Her dad watching from where he stood.

Zack was excited, his heart rate up when the video ended with his hand rubbing his crotch. Pulling off the VR glasses he glanced to his left at his dad who had a hand down the front of his unzipped pants, a smile on his face. That was unexpected, at his house she had just been a tease as they played at getting naked before going into the hot tub or sauna.

As the lights came up Lisa came down the stairs, Hannah behind her. Lisa had a short leash in her hand that was attached to a belt of copper rings around Hannah’s waist. All 5 foot nothing and skinny she wore a tight sheer tube top of the same material as her mother’s blouse. Her small pink nipples pressed hard against the material. She had on matching white sheer panties dotted with little bows. Lisa had also gotten rid of her shorts and now wore a matching pair of sheer panties like Hannah’s.

Zack locked eyes with Hannah as she found his seat. She smiled at him and gave her blonde hair a little toss. As she stepped barefoot onto the carpet Lisa turned to them both.

Hannah’s mom looked addressed Zack.

“I give Hannah over to your care Zack as your slave, do as you see fit for the afternoon,” Lisa said in a sweet voice. She took the end of the leash and walked over to Zack.

Zack was mesmerized by his friend as she approached. Her cheeks and chest sparkled in the light as her mother led Hannah to him handing him the looped end of the leash. His heart was racing his cock growing harder in his pants.

“Go on take her upstairs she knows where to go.” Hannah just tilted her head and grinned at him.

“So, I can ask her to do anything on this date?” Zack said without taking his eyes off his nearly naked friend who was now in her slave role, just looked down at the carpet.