The Oak Street Method

by Emily Tilton

  “For what?” Wendy asked in a whisper. She looked at Tom, clearly coming to the natural conclusion that her daddy had imposed the punishment on Mommy.

  Serena spoke again. “Something sexual.”

  Tom knew exactly where to go with it. “Pumpkin, Mommy isn’t allowed to play with herself without asking Daddy. I caught her this morning, and now she has to have a paddling, and then she has to open up her bottom for Daddy’s penis.”

  He glanced at Wilma, who was chewing the inside of her cheek, for all the world like she were ashamed of herself and worried about her coming discipline, though knowing her Tom could tell she was actually suppressing a giggle.

  Wendy’s jaw dropped, and she started to breathe quite heavily. “You’re going to… to do that… in her bottom?”

  Tom nodded gravely. “Yes, pumpkin. A dominant daddy likes me uses anal sex to discipline girls sometimes.”

  Her eyes went wide. Serena said on the comm channel. “Perfect opening. Go ahead, Wilma.”

  Wilma reached out and took Wendy’s hand. “Soon you’re going to belong to a wealthy man, Wendy, and he’s going to discipline you that way, I’m sure. You’re going to be auctioned tomorrow, and a master will buy you, take you to a little honeymoon cottage they’ve got all ready for you, and have sex with you there.”

  Wendy’s panting, open-mouthed breaths seemed loud in the evening air.

  “Then you’ll be trained,” Tom said. “Your owner will decide exactly how, and you’ll probably come back to Oak Street for a while, so that the mommies and daddies can train you, but you may also be sent somewhere else called the Institute, where there are lots of girls like you and Frankie and Mary, being trained for the men who own them.”

  “I don’t understand,” Wendy said weakly, “about… about the training.”

  Wilma smiled. “Yes, you do, sweetie. I know you do, because I’m like you, too.”

  * * *

  They had Wendy get into her nightgown and brush her teeth before she came to the master bedroom on hesitating feet.

  “Come in, pumpkin,” Tom called when he saw her standing outside the door, looking in with wide eyes. Wilma, naked and looking amazingly fit from the hour a day all the Oak Street mommies spent at the gym, was kneeling before him with his cock deep in her mouth. Tom held the back of her head firmly as he pumped himself in and out in an easy rhythm. “Mommy always sucks Daddy’s cock before a spanking.”

  Wendy’s face displayed all the erotic confusion a twenty-year-old submissive could feel. Tom watched her hand drift to the front of her blue-flowered nightgown, and press a little there. She drew a sharp breath, and took her hand away with a guilty expression.

  “Go ahead and play with yourself, pumpkin,” Tom said. “Pull up your nighty and show me that cute pussy your mommy got so nice and smooth.”

  When Wendy complied, her eyes looking like those of someone in a trance, and stood with her nightgown gathered in her left hand and her fingers playing gently upon her rosy clit, Tom said, “Alright. Time for Mommy’s spanking.” He pulled his cock from Wilma’s mouth and looked down at her with all the dominance he had at his command. “Go get your hairbrush, Mrs. Kimball.”

  “Yes, sir,” Wilma said softly, looking up at him with adoring eyes.

  Tom glanced at Wendy and saw instantly the brilliance of the assessment team’s decision to have the girls watch their guardians fuck: she had noticed exactly how submissive Wilma was, and how happy it made her, and her eyes had grown very wide.

  “Mommy,” Wendy asked, “are you naked for your spankings, too, like me?”

  “Of course, sweetheart. It’s even more important for me to be naked, to show that I belong to Daddy.”

  Wilma smiled and rose to go to the dresser. Tom saw Wendy’s wide eyes go a little wider still. She knew her mommy’s hairbrush stayed there, just as her own stayed on the dresser in her room. Tom could see that Wendy had never realized what it meant: that Wendy’s mommy got punished just the way Wendy did, because Daddy had to teach Mommy to behave sometimes, too.

  As Wilma came back to lay herself over Tom’s naked lap as he sat on the edge of the big bed, he saw that Wendy had also puzzled out the more realistic layer of affairs on Oak Street. None of this would have been a source of pleasure and self-discovery if it weren’t also a kind of play. Wendy hadn’t pieced it all together, of course—Tom knew that only a much more extensive understanding of the intricate inner workings of the Institute could bring that about—but she had comprehended the basic idea that someone had figured out what she needed, and brought her here to live on Oak Street so that she could get it.

  Wilma said, turning her face to look up at the adorable dark-haired girl who held her nightgown up to show her guardians her virgin pussy, “Don’t be scared, sweetie. Daddy spanks Mommy very hard. But Mommy knows she needs it.”

  “Come stand right in front of me, pumpkin,” Tom said, rubbing Wilma’s taut bottom-cheeks to make her sigh and whimper. “I want you to masturbate while I punish Mommy. It will teach you that it’s okay for your body to get aroused, and your pussy to get wet, when you think about spanking and punishment.”

  He spanked Wilma, then, until her bottom was beet red and Wendy had come twice. Wilma, who Tom knew both loved the punishment dynamic and had a masochistic streak, had sobbed and cried and begged Tom to stop. Wendy had seemed a little distressed at first at the strength of her arousal, but she had no power to stop it, and when she realized that the scene wasn’t going to hurt Wilma, or make Wendy spontaneously combust, she gave herself over to the pleasure so beautifully that it made Tom’s heart ache.

  “Pumpkin,” he said, looking down with great satisfaction at the lovely bottom he had just punished, “would you please go get the little bottle on Mommy’s nightstand?”

  Silently, Wendy brought him the lube. Wilma had quieted over Tom’s lap, her face in the comforter. When Tom pulled her cheeks apart, she gave a moan.

  “Isn’t Mommy’s anus cute, pumpkin?”

  “Yes, Daddy,” Wendy whispered.

  “Would you like to get her ready for Daddy’s penis?”

  “Do I have to, Daddy?”

  Wilma gave another moan as Tom pushed his middle finger gently against the little brown dimple.

  “No, pumpkin, you don’t have to, but remember that you’re going to have a penis in your own bottom before too long. I want you to see how Mommy has learned to use her muscles so that she can open and even enjoy being fucked in her bottom. Here, give me the lube. I’ll start getting Mommy ready, and you can watch, and then you can feel what her anus is like if you want.”

  “Okay, Daddy,” Wendy said quietly. “Is it going to hurt?”

  “It hurts a little, sweetie,” Wilma said, turning a smiling face back over her shoulder to look at Wendy, “especially when Daddy fucks me there to punish me. But you’re going to be trained so that you understand that sometimes it’s even nice for it to hurt.”

  Wendy did finally put one finger and then, at her mommy’s encouragement, a second, inside Wilma’s bottom. She exclaimed over how open she found the little ring, and Tom could see she had indeed taken reassurance from it.

  As she watched her mommy fucked hard in her bottom, masturbating helplessly again, Tom saw Wendy start to understand exactly what Wilma had described: he saw his young ward develop a sudden yearning to be hurt, a little, that way. When at last he came inside Wilma’s backside, and called Wendy’s attention to the semen trickling out of the little hole in her mommy’s still red bottom, the shy smile on her face told him that tomorrow wasn’t too soon for her auction.

  Chapter Nine

  As her mommy and daddy had promised, Wendy was sold the next day to the highest bidder.

  An unmarked white van pulled up at ten a.m. in front of 6 Oak Street. The Kimballs had already told her to dress in her Sunday clothes, as usual, but to expect the rest of the day to go differently from an ordinary Sunday.

  Standing in the living room with her mommy
and daddy, Wendy watched a man in a dark suit get out of the van and walk to the door. Her daddy opened the door as he approached, while her mommy, with her arm around Wendy’s shoulders, said gently, “It will be a little scary, at first. But remember what we talked about, last night.”

  That made Wendy’s heart beat even faster, though, as she tried to process all the events of the day before. They had talked about so many things, and all of them had something to do, she knew, with what would happen now. The auction.

  Then Daddy took her hand and led her to the door, where the man in the dark suit waited. She noticed how tall he was, and how his muscles bulged a little in the elegant clothing.

  “Good morning, young lady,” said the stranger. “I’m Master G. It’s nice to meet you.”

  Wendy looked uncertainly at her daddy.

  “It’s alright, pumpkin,” he said. “Use your manners, please. You must call Master G Master. Remember that, but he doesn’t bite.”

  Trembling a little, Wendy turned to the man. “Good morning, Master,” she said.

  Then Daddy hugged her. “Be a good girl, now. We’ll see you soon.”

  As Wendy walked to the van, she looked around the quiet neighborhood. She thought she saw Ginnie’s face at her bedroom window, and she wondered what Ginnie must think, seeing Wendy taken away in a van, especially after Daddy had sent Ginnie and Heather home from the Woods, the day before. Wendy wondered how Frankie and Mary were, and whether their evening of watching Mr. and Mrs. Wood have sex had been as moving and as confusing as her own. Had their mommy and daddy told them they would be sold at auction, too?

  Inside the van, on one of the benches that ran along the sides sat another man, who also wore a dark suit. “Good morning, Wendy,” he said. “You look very pretty. I’m Master S.”

  “Good morning, Master,” Wendy said, without prompting. Master S seemed just as tall and muscular as Master G.

  The van pulled away, driven by Master G, and out of Oak Street.

  “How long…?” Wendy started to ask, very tentatively. She saw that Master S’s face had gone a little stern, and she hastily added, “Master?”

  “How long is the drive, do you mean, Wendy?” he said. “Not long.”

  “And…”

  Master G said from the front seat, “Don’t speak unless you’re spoken to, Wendy.” His voice sounded sharp, and Wendy heard in it the unmistakable implication: girls who speak out of turn get punished.

  Wendy felt her brow crease, and she looked down at Master S’s shiny black leather shoes.

  “Your guardians told you everything you need to know,” Master S said, a little more kindly. “When we arrive, I’ll take you into the house, and a nice lady named Miss Charlotte will take you to the room where you’ll be sold.”

  The van door opened at last to reveal a big house—a mansion, or a chateau, really. Wendy had never been inside a house like that before. Master S stepped out of the van, and then helped her step out, too. He walked her to the doorway, which opened as soon as they reached it, to show a beautiful blonde woman wearing a little white nightgown. She seemed ageless, but she was certainly older than the red-haired girl standing next to her, in a similar nightgown, though the younger woman’s was blue.

  “Welcome to the Institute, Wendy,” said the woman in white, very warmly. “I am Miss Charlotte. You may call me that, or simply Miss.” She turned to Master S. “Thank you, Master,” she said with a smile. So this Miss Charlotte had to call them Master, too?

  “My pleasure,” Master S replied. He turned to the red-haired girl standing next to Miss Charlotte. To Wendy’s surprise, as soon as the girl sensed his attention, she fell to her knees, her eyes downcast. “Janine, thank you for this morning. You were a good girl under my cock.”

  Wendy felt faint. Looking at Janine’s pinkening cheeks made her warm in her panties. What did it all mean?

  “Thank you, Master,” the kneeling girl said softly.

  “Wendy,” Master S said, turning to her. Suddenly Wendy wondered if she, too, should kneel. Somehow it seemed like the correct thing to do. And… she realized to her surprise that she envied Janine. She wanted to be like that. The thoughts and feelings grew so confusing that she found herself looking into the big man’s face without really seeing it.

  “Eyes down, Wendy,” said Miss Charlotte gently. “You may not look a master in the eye.”

  Wendy obeyed, feeling the heat come into her own face. She found herself looking at Master S’s silver belt buckle.

  “It was nice to meet you, Wendy,” he said. “I’ll see you again soon.”

  And what did that mean? Mommy and Daddy had said something about being trained at the Institute, hadn’t they? Would Master S be one of the people doing the training? Was Janine in training, and did she have to a good girl under his cock as part of her own special lessons?

  Master S turned and went back down the path in the morning sunlight. Janine closed the big front door of the mansion, and now for the first time Wendy saw that they were in a vast foyer, with a marble floor and a grand staircase leading up to a balcony.

  “Janine will take you to a waiting room, now, Wendy,” said Miss Charlotte. “The auction begins in twenty minutes, so you won’t have long to wait. You may ask her a few of your questions, but I’m afraid there won’t be time for a full explanation before you are sold. After that, your owner will decide what he wishes you to learn, and how he wishes you to be prepared for your defloration.”

  Janine rose and smiled at Wendy. “It’s nice to meet you,” she said, and reached out her hand. “I hear you’re from Oak Street.”

  * * *

  To Wendy’s surprise, everyone seemed to know all about Oak Street, when Janine led her into the enormous living room, where at least twenty well-dressed men sat waiting. They didn’t wear suits like Masters G and S, but had on the most elegant clothes Wendy had ever seen: some wore what must be silk shirts, others sports jackets that Wendy imagined must be made of cashmere. All of them had an air of wealth that seemed to glitter from gold cufflinks and shimmer from neat pocket squares.

  Miss Charlotte stood at a podium on a little dais. Next to the podium stood a strange piece of furniture, low and padded, with things attached to it that Wendy couldn’t immediately recognize. As Janine led Wendy in, she announced, “Please welcome Wendy, from Number Six, Oak Street.”

  The men applauded in a way that seemed to Wendy so enthusiastic that she thought being from Oak Street must have a special meaning for them that it didn’t, for her. Janine’s answers to her questions hadn’t been very helpful: mostly the sweet red-haired girl had said, “You’ll find that out from your owner” or “The trainers here will teach you about that.”

  Some of the mystery was taken away as Miss Charlotte continued, but her words seemed to leave Wendy with even more pressing questions.

  “You’ve all watched the progress of the Oak Street project with great interest, I know.”

  Many of the men chuckled at that: great interest must be an understatement. Wendy blushed: if twenty wealthy men had assembled to bid on her… on her virginity, on her body… Had they somehow been watching her ever since she arrived on Oak Street?

  “Now I present to you the first girl to be sold from the project. Janine, would you help Wendy out of her dress, please?”

  Wendy turned with wide eyes to the girl she couldn’t help thinking of as her new friend. Janine gave her a smile that she clearly meant to be reassuring, but Wendy’s heart wouldn’t stop racing. She remembered that she and Frankie and Mary had all been naked yesterday in the presence of their mommies and daddies, but to have that happen here in front of all these well-heeled men, who she could see were watching her so very closely, made what felt like her whole head and neck seem to get burning hot in a rush of embarrassment.

  What had Mommy said? About needing it? Needing this? Wendy knew somehow that she did, but that thought didn’t seem to make her tummy flutter any less as Janine unzipped the back of the b
lue Sunday dress, and helped her step out of it to show her modest beige bra, her suspender belt, and her pink panties.

  More self-conscious than she could ever have imagined a person could feel, Wendy tried to cover her underwear with her arms, but Miss Charlotte said, “Hands on your head, please, Wendy. These gentleman wish to see what their money will buy.”

  Wendy looked at her, and to her surprise she saw on this strange woman’s face the same kind of sympathy her mommy’s had worn the previous day. Miss Charlotte clearly had the very same knowledge of Wendy’s needs that Mrs. Kimball had. Had Miss Charlotte been watching her this whole time? Had Miss Charlotte chosen Wendy—and Frankie, and Mary, and… the others, too?

  Her lips parted, because though she knew she wouldn’t be allowed to ask any questions, they all seemed to gather in her chest to the point of overflowing into speech. Her hands stayed where they were, because the questions took up all her attention.

  “Janine,” said Miss Charlotte, “please get Wendy ready for a spanking.” She had taken something from somewhere in the podium. A leather thing… long and narrow, somewhere between a strap and a paddle. She held it in her right hand, the face of the implement resting on her left.

  “Oh, no,” Wendy said. “Please, no.” She moved her hands at last, put them on her head. She darted a glance out into the audience, and saw the men smiling, chuckling to one another.

  “What do you think, gentlemen?” asked Miss Charlotte. “All in favor of a spanking, say Aye.”

  The cultured voices, all of them, said, “Aye.”

  “Opposed, no?” Charlotte asked, and silence reigned.

  Janine said, “Lie down on the spanking bench, Wendy.” She pointed to the strange piece of furniture next to the podium, between Wendy and Miss Charlotte. Then she said, more softly, “Don’t worry. It was going to happen anyway.”

  Wendy had to lie over the bench, and Janine strapped her down at wrists, waist, and knees, as Wendy trembled. Janine lowered Wendy’s pink panties, and Wendy gave a little sob of shame, and of need. She felt the warmth and wetness rush to her pussy, and she knew that since her mommy had bared her down there, they would all see.