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Home / Stormy Night Publications Newsletter / Beyond Oak Street: Their Billionaire Daddies by Emily Tilton – Extended Preview

Beyond Oak Street: Their Billionaire Daddies by Emily Tilton – Extended Preview

Tricia didn’t even make it to Italy without another forgetful incident. From the way she had reacted the previous night to the news that she would be subject to anal discipline like Luisa, Joe supposed he should have expected it, but it still took him aback when she tearfully confessed, on the private jet carrying them and four other couples from New York to Rome, that she had neglected to pack her underwear.

Joe felt his brow furrow. “How could you forget your panties, sweetheart? I could understand forgetting a bathing suit, maybe, but I thought underwear was the first thing anyone packed.”

“I’m sorry, Daddy,” Tricia whispered up to him from her luxurious leather seat next to the window, through which Joe could see the Atlantic sliding by far, far below.

“And how did you just realize it now?”

“What did she do?” Luisa asked from the row behind them, where she had the window with Paul on the aisle.

Tricia turned in her seat to look back through the opening next to Joe’s shoulder. “None of your business, Luisa,” she said, the petulance rising in her voice.

“It’s my business if it means we can’t go straight to the hotel and take a nap,” Luisa shot back, her voice getting louder with indignation.

Joe looked over to the other side of the aisle, to see whether any of the other Institute couples had caught on to the fact that the Barbera brothers were having trouble with their bed girls. Joe and Paul were the only Oak Street owners aboard; two of the other couples seemed like New Modesty types that must come either from the Thoroughly Trained program or from Extreme Marriage.

The remaining two appeared to come from what Joe thought of as the European-lifestyle end of the Institute spectrum: the bed girls had on dresses that didn’t differ from lingerie in any important respect—and they wore them as if they were evening wear. Joe had had to suppress a laugh as he watched one of the New Modesty girls, dressed herself in an ankle-length skirt and blouse worthy of a Victorian schoolroom, look with pink cheeks at Starla, the platinum-haired, rail-skinny concubine who had a stylish leather collar around her neck with a subtle but unmistakable D-ring at its front.

The New Modesty couple seated just across from Joe had caught on, it appeared, to the difficulty with the Barberas’ schoolgirls. The young wife in the long skirt, whom her husband, Hank Granby had introduced only as ‘Mrs. Granby,’ had begun to whisper to her husband, with significant glances at the Giuliani girls. Mrs. Granby couldn’t be more than a year older than Tricia, if that, but the Oak Street girls had on their school uniforms, of course, and so the contrast appeared quite stark, and rather arousing.

“Princess,” Paul put in, his voice carrying a warning, “mind your own business.”

“But, Daddy,” Luisa protested, stressing the word enough that Joe saw Mrs. Granby’s eyes go wide, “I just said that it’s my business.”

Joe turned to the younger girl. “Luisa, I will go and buy new underwear for Tricia in Rome, or we’ll ask the concierge to do it.”

Luisa’s eyes went wide with incredulity. “She forgot her underwear?” she demanded. “Tricia, how do you forget your underwear?”

Joe thought back to his conversation with Charlotte the previous afternoon.

“You need to expect that both girls are going to act out. You and Paul will have to discipline them, of course, but you should understand that it’s not really willful misbehavior. In fact, if Tricia does forget something tomorrow or the day after, it’s probably a good sign—and then if Luisa reacts with naughtiness on her own part, it will mean that we’re getting somewhere.”

Joe had considered for a moment, looking out the window of his corner office at Barbera Financial.

“Do you mean that threatening to plug her backside will actually make her forget?” he had asked, then. “That doesn’t seem like progress to me.”

“I get that,” Charlotte had replied, her voice crystal clear over the Institute’s encryption system despite the distance and the signal compression. Those Institute coders knew their stuff. “But look at it this way. These memory lapses are, in their own way, like, say, Tricia sneaking a cookie from the cookie jar—but instead of giving her a spanking for sneaking the cookie, you punish her for leaving crumbs on her comforter. Then imagine that Luisa is also sneaking cookies, but getting disciplined anally for the sneaking—and the crumbs. Given who both girls are, you can imagine Tricia continuing to sneak cookies, right?”

Joe had chuckled as he began to understand. “So by giving her the same special punishment Luisa gets we make it clear that we understand that she’s ‘forgetting’ because she’s jealous of Luisa—even though she probably doesn’t even know it.”

“Yes. And that poses a problem for Luisa, too, since her special punishments make her feel, well, special.”

Joe had protested a little at that part. “Tricia has her special punishments, too, though.”

“Spanking her between her legs,” Charlotte had said. “Yes, but here’s the thing—when Paul plugs Tricia, she has to keep it in for a while, doesn’t she? It reminds her that it’s there, if you know what I mean.”

Now, on the plane, Joe knew what he had to do—and he had put what he needed to do it with in his inside breast pocket before leaving the apartment. The informational email with details about the event in Rome and the travel arrangements had made it clear that owners should feel free to discipline their concubines at any time, including on this flight. Given the unique opportunity presented by having four other owners whose bed girls had graduated from the Institute in one training program or another, Joe decided to make sure Tricia understood that her daddy intended her new punishment regime to become an important part of her life.

“Sweetheart,” he said, calmly but sternly, “you and I are going to go to the bathroom, now. I’m going to plug your bottom.”

“No, Daddy, please!” Tricia wailed. The concubine with the platinum hair and the collar turned to look back at them from the front row of seats on Joe and Tricia’s side of the aisle. He glanced over to see that Mrs. Granby’s face had gone bright red. Joan Riley, the other New Modesty girl, who wore a demure red dress that looked like it had come from the 1950s, turned with wide eyes to look at them.

“You heard me, sweetheart,” Joe said, starting to stand up. “If you don’t get going right now, you’re going to get a spanking, too.”

“Daddy, please!” Tricia repeated. “Please, not the plug!”

Joe felt his eyebrows go up quite a ways, as he heard, even above the noise of the jet engines, other girls start to whisper to their owners, and some of the men growl warnings to mind their own business in return. Joe had to assume that at least of few of his fellow owners used anal discipline with their bed girls, but Mrs. Granby’s pink cheeks indicated that even if she did have her own young bottom opened by Mr. Granby when he thought his wife needed a lesson in proper behavior, she found it shameful to have another girl mention the possibility.

“Not another word, Tricia,” Joe said. “You know I won’t hesitate to march you in there if I have to.”

With tears in her eyes, and a last look at Luisa, who seemed chastened by Paul’s implicit promise to plug her, too, Tricia got up from the seat and joined Joe in the aisle. She cast her face down, her cheeks showing her blush a little despite their olive complexion. As she walked ahead of Joe to the bathroom at the rear of the jet, Joan Riley asked her husband very audibly, “Is that girl getting punished?”

The bathroom, for an airplane, was quite big and even rather sumptuous—almost like a hotel bathroom, really. Tricia turned to Joe as soon as he had closed the door behind them and locked it, to make the lights go on, just like on an airliner.

“Daddy, please? I’m sorry I forgot. I’ll… I’ll pay for the new panties with my allowance. Please don’t plug me.”

“Tricia,” Joe said patiently, sure from the contrite, fearful look on her face that he had made the right decision, “turn around and bend over the toilet. Palms right on the cover and knees bent.”

She gave him a final look, her brows knit in consternation, and then she obeyed, turning and presenting her rear end in her uniform skirt, over her trim thighs and white knee socks.

“Arch your back, sweetheart,” Joe said as he flipped up her skirt. “Push your bottom out.”

Tricia gave a little sob as she complied, her lovely hind-cheeks swelling a little in the thick white briefs. Joe stepped forward a little and took her right hip in his left hand. He couldn’t resist fondling his schoolgirl’s sweet bottom in those innocent panties, letting her know that part of her belonged to him utterly. He held each cheek in his hand and squeezed it gently as Tricia emitted tiny whines from her throat to feel her daddy’s ownership of her tushy, and the hairless pussy he cupped, then, through the heavy fabric of her schoolgirl underwear, making the whines turn to a long moan.

Joe’s cock had grown as hard as iron, and the urge to fuck his bed girl before he plugged her came over him so strongly that he had to fight hard against it. He put his right hand in the waistband of the briefs and pulled them down, all the way past her knees, so that they dropped to the floor, as Tricia gave a little cry of surprise.

“Your punishment for forgetting to pack your panties isn’t just going to be the plug, sweetheart,” Joe said into her ear. “You’ve lost your panties for the whole trip.”

“Oh, Daddy,” Tricia wailed. “No, please. Please. Our skirts are so short! And… and now… they’ll see!”

“You should have thought of that when you were packing, Tricia. And yes, the people on the plane will see the plug, but not because they’re sneaking peeks up your skirt. They’re going to see it because you’re going to show it to them.”

Tricia tried to straighten up and turn around at that, but Joe held her down over the toilet and fetched the lube out of his pocket. One-handed, he flipped the top open.

“Daddy… no!” She struggled against his restraining arm, but he managed to drip a healthy stream of the clear, viscous liquid onto her backside, just above the crease between her squirming bottom-cheeks.

The roar of the engines drowned out a good deal of the sound in the bathroom, but Tricia put up a fuss now that Joe thought must be audible in the main cabin. Twisting against him as he got her tiny ring ready to take something big and hold it inside her, she screeched loudly in protest.

“Stop! I… I can’t! I’ve seen Luisa’s. It’s too big!”

“Shh, sweetheart. You know Luisa’s younger, and her bottom is smaller, so that’s nonsense. I should have plugged you the way Daddy Paul does with her a long time ago. And you know you already get Daddy’s penis there when he decides you need it. Hold still, now. Hands on the toilet cover. Keep this bottom pushed out.”

She quietened a little as he put the lube back in his pocket and began to work her little flower on his fingers, putting two in as soon as she relaxed for one, and making her cry out in need as much as in discomfort at the insistent invasion of her most private place. He got the purple plug—the same size as Luisa’s but a different color so they could tell them apart—from his pocket.

Tricia whimpered when she felt the rounded head of it against her anus, but Joe meant to make her understand she was being punished, and he pushed firmly. His schoolgirl emitted a cry of pain as she felt her bottom stretched as never before, and then a sob when the widest part of the plug had passed inside her. Her anus tightened around the narrower place, just in front of the flared base, that would hold her young bottom open until her daddy decided she had learned her lesson.

Tricia gave another sob when Joe pressed gently on the base of the plug, her backside bouncing with discomfort. Now he couldn’t resist, and he didn’t have to. He let her hip go, but as Tricia started to straighten up, he said, “Stay there, sweetheart. Daddy’s going to fuck your pussy now.”

Out in the cabin, where Luisa sat next to her daddy wondering what would happen to Tricia in the bathroom, the sounds from the bathroom, which had gone silent for a few moments, suddenly came back. Luisa looked around at the other couples on the plane, especially the other girls, all of them about her age but, because Luisa was an Oak Street girl in a school uniform, seeming so much older that it made Luisa’s face get hot—especially in view of the fact that her ‘sister’ Tricia had just had to go to the airplane bathroom to be punished by her daddy.

The light brown-haired girl named Joan gave Luisa a sympathetic look from right across the aisle, but redheaded Mrs. Granby in front of Joan, who seemed much too young to be a Mrs., and even younger to look so censorious, clearly disapproved of naughtiness on principle. She looked back at Luisa with an expression in her blue eyes that said she felt sure the girl in the bathroom’s younger sister required just as much old-fashioned discipline as the girl in the bathroom herself did.

Tricia cried out once, and then she repeated the sound. Then the cry came over and over. Luisa’s cheeks burned and her pussy tingled as she understood what Daddy Joe was doing to his Oak Street girl—Luisa herself made almost exactly the same sounds when her own daddy fucked her with the plug inside her bottom.

The blonde girl, Starla, in the front row of the Giulianis’ side of the cabin, giggled then, and said something to her boyfriend, or… Luisa swallowed hard, as her mind supplied the true identity of the well-dressed older man Starla accompanied. Her owner. Her master. Starla wore a collar around her neck, and Luisa couldn’t seem to take her eyes off it.

Or the anklet the girl in the front row on the other side of the aisle wore, because something about it—the strange triple-ring design on the charm, maybe—seemed to Luisa to be like Starla’s collar. Linda, her owner had told the daddies her name was.

Her master, who bought her. The way the daddies bought us.

A master was like a daddy, but more…

Luisa wondered how to fill in that gap, then bit her lip as the word came to her, just as Tricia’s muffled cries stopped.

More demanding.

She found it hard to see how a master could be more demanding than Daddy Joe had just been with Tricia, to judge from the sounds she had made in the airplane bathroom. Tricia hadn’t even gotten to come, Luisa could tell beyond a shadow of a doubt from the way her sex noises had just abruptly ceased.

“What’s going to happen now?” she whispered to her daddy fearfully, tugging on the sleeve of his blue Oxford. Luisa half expected Daddy Paul to tell her she would go into the bathroom with him, next. Somehow, too, she half wanted him to say it.

That thought really set her thoughts whirling and her tummy jumping. Luisa could never have imagined, back on Oak Street or in the daddies’ apartment, wanting something so terribly embarrassing to happen to her. When other girls—especially Tricia—got disciplined, Luisa had to admit she couldn’t help watching very closely, and finding the sight terribly moving. But she had never before felt jealous of Tricia or any other girl she had seen being made to learn a bare-bottom lesson.

“Wait and see,” said Daddy Paul. He kissed her forehead, and then her lips.

Across the aisle, Mrs. Granby said to Mr. Granby, in a voice so distinct she must have wanted Luisa to hear what she said, “How old is that girl, Henry? And the other one, in the bathroom? She’s not much older.”

The words made Luisa’s whole body flash hot, and her mind replied to the woman’s evident disapproval of her daddy kissing her on the lips in a way that made her embarrassment even greater, Old enough to have the same kind of big-girl time I bet you have with your husband. Old enough to have a plug in her bottom—the way your husband should do to you, to remind you to keep your nose out of other people’s business.

The bathroom door opened, and Tricia came out first, her eyes bright with unfallen tears. Luisa’s cheeks burned anew when she saw what the older girl carried in her hands: her white cotton briefs. Luisa felt her brow furrow as she thought about what it meant, about what Tricia must feel like under her pleated plaid skirt.

Mrs. Granby, whose husband had replied to her question about the Giulianis’ age in a low voice that had seemed to Luisa to have a warning in it, said in an outraged stage whisper, “What is she holding? Are those her panties?”

Tricia’s face remained fixed on the carpeted aisle in front of her as she walked slowly forward with Daddy Joe behind her.

“Why is she walking like that?” asked Mrs. Granby.

Mr. Granby lost his patience with his wife, then. “Jenny, one more word,” he said in a voice audible to everyone in the cabin, “and you’re going in the bathroom for your own lesson. You have a spanking coming as soon as we get to the hotel, in any case.”

Luisa’s eyes went very wide. She saw Tricia turn a little to look at the Granbys, whom she had almost reached in her slow, shameful progress up the aisle, and then return her eyes to the floor of the jet.

Mrs. Granby’s pretty face had gone beet red. “Henry!” she said, and then she turned to the window.

Luisa remembered what the daddies had told them about the people they would meet on the plane and at the hotel. All the girls had something to do with the Institute, but the daddies had said that could mean a lot of different things. Mrs. Granby didn’t seem much like the other wife, Joan, let alone Starla and Linda—let alone Tricia and Luisa.

And yet her husband had just told her she would go over his knee in their hotel room, the same way Luisa went over Daddy Paul’s knee when she was naughty. Through her blush, Luisa felt again that strange little wave of envy. Did it have something to do with not being the only girl in the Barbera household who had her bottom plugged for misbehavior?

Luisa looked at Tricia walking gingerly up the aisle, a deep crease in her forehead at the burden in her bottom and her cheeks the dark red that showed a Mediterranean blush, at her gait and at being made to carry the panties her daddy had removed. Luisa expected her to turn and start to get into her airplane seat, but instead she kept going, up to the front of the plane where the flight attendant sat in her blue uniform coat-dress.

Daddy Joe, on the other hand sat down in his own seat, while Tricia bent to whisper something into the pretty stewardess’ ear. The flight attendant nodded, a grave look on her face, and then she reached out to give Tricia’s hand a little squeeze. Luisa’s heart jumped a bit, and her affection for her older ‘sibling’ overcame the strange jealousy for a moment.

Poor Trish. She must be more embarrassed than she’s ever been in her life. Luisa bit her lip, then, though, because the jealousy came back in what felt like an inner tidal wave, saying that she should be up there talking to the flight attendant with a plug up her backside. For the first time, Luisa thought she might understand what the daddies had to think about when they tried to figure out how to help Tricia remember better and get punished less.

Maybe some of that jealousy had been in the older girl’s mind, too—maybe Tricia hadn’t even known it was there? It seemed so strange to think that anyone—Tricia or Luisa or Mrs. Granby or anybody—could feel jealous of another girl getting a big plug pushed deep into her anus. As Luisa watched the scene at the front of the jet unfold, though, she had to admit the possibility nevertheless. Despite being very, very glad it wasn’t her saying to the stewardess whatever humiliating thing Tricia had to say, Luisa also wished it were.

Am I losing my mind?

If she had thought the scene of Tricia’s first anal punishment had brought conflicting feelings to her mind and body up until now, what happened then made the problem much worse.

The stewardess fetched the PA microphone from its place on the wall, and said over the speakers, “Hi, folks. This young lady tells me she has to say something to everyone.”

Luisa felt her whole body tense up as she saw the look of utter mortification on Tricia’s face. Down below, her pussy got so warm and needy that she had to fidget in her seat to keep from whimpering with arousal and alerting her daddy to the embarrassing state into which she had put her own white school panties. The thick stretch cotton always seemed to try to deny the sensations in the pussy Daddy Paul loved to keep so smooth for him to kiss and kiss and kiss until Luisa begged him to stop because she would pass out if she came again. When Luisa got it damp, though, it stayed damp for a long time, and that always increased her shame and made her think of what would happen if Daddy Paul inspected her underwear the way Mrs. Giuliani had sometimes when the girls lived on Oak Street.

Tricia looked at Daddy Joe with a final plea to be spared saying whatever he had told her she must, but Daddy Joe nodded to her to go ahead.

Miserably, Tricia began, “My daddy wants you all to know that I’m a forgetful girl, and I’m being punished for not packing any underwear. That’s why I’m not allowed to wear panties now, and…”

She had focused on the carpet as she delivered the humiliating little speech, but now she tried again to persuade Daddy Joe to spare her this awful lesson, lifting her tearful eyes to where he sat watching.

“Please, Daddy? Isn’t that enough?”

But Daddy Joe shook his head. “Keep going, sweetheart,” he said in a loud enough voice that all the passengers could hear it. Looking around the cabin as best she could from her seat, Luisa saw between the seatbacks that Starla and Linda had amused, almost giggly looks on their faces.

Joan Riley, across the aisle, had spots of pink on her cheeks, and her chest rose and fell with rapid, shallow breathing. Her husband had put his right hand on her thigh, and Joan had laid her own hands on top of it, lightly, as if she couldn’t decide whether to push it away or pull it toward her. Luisa gave out a little whine as she watched Mr. Riley move the hand up, and begin to fondle his modest wife between her legs.

The whine got louder as at the very same moment Daddy Paul put his own left hand under Luisa’s skirt and cupped her bare pussy through her thick panties. She found herself doing the very same thing with her hands she had seen Joan do: Luisa put them on Daddy Paul’s possessive hand, wanting to beg him to stop and wanting to beg him to put his hand inside her panties, and settling for feeling her daddy do exactly as he wanted down there.

Mrs. Granby had her hands balled into little fists in her lap, and she looked at Tricia with an air of horrified fascination. Mr. Granby had put his hand on his wife’s knee, almost as if he meant to restrain her from rising and trying to interrupt the proceedings.

Tricia looked at the flight attendant, and then at the carpet again. She mumbled, “And I have a plug in my bottom, to help me remember, and…”

She didn’t try another look at her daddy, which made Luisa think that Daddy Joe’s face must have had a very deep frown on it when Tricia had interrupted herself before. Luisa moved against her daddy’s rubbing hand and tried a “Please?” of her own, in a whisper into Daddy Paul’s ear. Then she gave a happy cry, because her daddy had worked his fingers inside the waistband of Luisa’s panties, to touch her tiny bud of a clit the way only he knew how to do.

“And I have to show you.” Luisa cried out, and so did Joan Riley, as Tricia handed the microphone back to the stewardess, then turned very quickly—clearly wanting to get it over with—and bent over, putting her hands behind her to raise her pleated skirt and show all the passengers the rectangular purple base of the butt plug peeping between the trim cheeks of her schoolgirl bottom.

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