Thank you all for the kind welcome and the support for "The Tutor". I know it had less ENF and more other to it than many people might prefer, but it wasn't written for this site originally, and I wanted to know a little more about how my particular type of storytelling would be received here.
This is my first foray into more pure ENF territory, but I thought I'd give it a shot. All characters are purely fictional, and don't do bad things in the real world, please.
Feedback is always welcome.
A Small Price To Pay
by Fred Key
Chapter 1 - A Small Price to Pay
Ryan lay in his bed, waiting and pretending to sleep.
He was seventeen years old, just a month or so from his senior year in high school, and a generally quiet guy. Most of the time, he faded into the background, or at least that’s the impression he had. He wasn’t unpopular, but he wasn’t the kind of guys who fit with an “in” crowd. He had a couple of buddies, and mostly kept to himself.
If Ryan did have an unusual characteristic, it was his ability to read people. He was a good listener, and he paid attention to the small details that others might not see. He was an absolute terror when it came to games that depended on predicting an opponent’s choices. Tonight, for the first time, he was putting that ability to the test where it really counted.
As he lay there, naked under the sheet, he felt his face flush. If he was wrong, he had mortified himself in front of Elizabeth and her friends for nothing. In fact, he would be reliving that mortification repeatedly, as he knew they wouldn’t let an opportunity to tease him and humiliate him slip by. He felt his bare neck prickle with goosebumps at the thought.
Even if I’m right, he thought, I have to pay the price for the victory. He could feel his stomach churning as he contemplated what he thought was ahead. Could he make himself go through with this? There was still time, he thought—and then he heard the sound of the knob on his door turning. No turning back now, he thought.
He closed his eyes firmly and tried to breathe as normally as possible. It sounded like a hurricane in his lungs, and it took every bit of effort not to move.
Finally, he heard a quiet click as his door opened. There was a muted giggle, and someone hissed “Shhh!” He knew what was happening. Knew what was coming. He knew, but it didn’t make it any less terrifying. He was about to be naked in front of a room full of girls–schoolmates–and his STEPSISTER. His heart rate exploded.
Ryan tried to distract himself by trying to pick out names and numbers. It was too hard. He was just too nervous. The squeak of wood underfoot was too close. He could smell flowers.
When the sheet twitched, it took everything he had in him to keep still and not clutch at it. It’s a small price to pay, he repeated in his head like a mantra. It’s a small price to pay.
The sheet slowly slid down his torso. He knew it would happen in seconds now. He would be naked and on display, something that had never happened to him before. He couldn’t do it. He couldn’t! But somehow, he kept still, even as the sheet slid past his waist and the cool air played on his exposed privates. Publics now, I suppose.
There was a whispered “Oh, shit! Look at it!” Another voice: “is that big or small?”
“Looks plenty big to me,” a third answered.
“Shut UP!” A fourth voice, this with some one authority said. “You want to wake him up?”
Too late, Ryan thought, but he continued playing possum. He saw the bright light of a camera-phone through his tightly sealed eyes as it flashed. Oh, fuck! He thought. They’re taking pictures! He had been prepared for the exposure, and had even given himself a few strokes every few minutes over the last half hour to ensure he would be suitably “impressive” for the audience he was certain would come. The thought of a group of 16 year old girls circulating pictures of his dick around their group chat, however, almost made him panic and grab for the sheets. Instead, he remained as still as he could, trying not to let his pounding heart show. They were all staring at his cock. What if it was too small? What if it looked–funny? If they laughed, he’d lose it for sure. He’d never live it down.
“It’s so..is that how it’s supposed to look?”
“You should touch it!”
“NO!” hissed Elizabeth. “You’ll wake him for sure! You got the pictures, and that’s plenty. He’s my fucking stepbrother!”
“He’s your HOT stepbrother,” giggled someone else. Ryan heard more shushing. “That’s the whole point, isn’t it?”
“Whatever- I’m gonna touch it! If he wakes up, we have the pictures now. He’s already ours.”
“Sarah! Don’t!”
Even braced for what he knew was coming, Ryan almost lost it when he felt the finger on the tip of his penis. He felt his member twitch.
“Did you see that? It freaking moved! Oh, that’s so weird!”
The finger slowly slid down the length of his shaft, which grew almost instantly. Ryan kept his eyes closed, but moaned a little, as if he was dreaming. More giggles.
“Wonder what he’s dreaming about now, huh? Maybe you, Liz?”
“GROSS!” Elizabeth whispered.
The finger moves to the sensitive underside of his shaft now, and Ryan decided it was time to “wake up”. He moaned again, a little louder this time, and slid his hand towards his crotch. At the same time, he let his eyes flicker open.
The girls jumped back as he clearly saw them in the soft glow of the smartphone flash illumination. “What the fuck?” He grabbed for the sheet and pulled it up, sitting upright in the bed. “What are you doing in my bedroom? Wait, is that a camera? Were you…what the hell, Elizabeth?”
A girl stepped forward. When she spoke, he recognized her voice as the one who was named Sarah. “Hi, Ryan. Good dreams? Looked like you were enjoying them from what I could see…”
“Ok, give me the phone and get the hell out and maybe I won’t tell Mom and Dad about this, Liz. You were spying on me naked? Taking pictures of my dick? Who does that?”
“Oh, c’mon, Ryan,” Sarah said. “After that truth or dare game earlier tonight, you couldn’t have thought we’d be satisfied with hearing you describe it to us?”
“You won’t be telling anyone,” said Elizabeth, arms crossed. “Unless you want all these pics strewn around the cafeteria.”
Ryan looked panicked. “No! You can’t do that! Please!”
Sarah tapped her lip thoughtfully. “Well…I suppose we could make a trade. I have something you want, and as it happens, you have something we want. How about this—we’ll delete the pictures, but you have to follow our instructions—ALL of them, no matter what—for the rest of the night.”
“I’m not going to do anything for you! Give me the phone! This is so fucked up, guys…”
Sarah shook her head. “We have the photos, Ryan. We make the rules. The sooner you understand that, the easier this is going to be.”
Ryan looked at each of the girls in turn. Sarah, a thin, chestnut-haired girl, was one he knew pretty well from school, where she kept two or three boys on a string most of the time. Ryan wasn’t sure how—she wasn’t nice to much of anyone, and her almost-boyish body made her look like a freshman, in his opinion. Annie was a freckled redhead who kept her hair in a ponytail. Ryan had crushed on her for most of a year, but had never worked up the nerve to talk to her. She was a taller girl who played for the girl’s lacrosse team, so she was usually sporting a variety of bruises on her arms. He assumed she had them on her legs as well, but she basically lived in leggings, so he hadn’t had much of a chance to verify that.
Cassie was a tiny brunette who had been in Ryan’s programming class. She wore glasses and tended toward hoodies and jeans, which is why Ryan had hardly recognized her when she came in the first Friday of the football season in her colorguard outfit. The tight spandex top and fitted black pants showed off a chest that was generous on such a small frame, and a tight backside that might well make a boy forget her chest.
Jessica was an army brat. She was easygoing and had learned to make friends quickly moving place to place. She had an infectious grin that made her approachable, and had the cascading sandy blond hair that fell just past the shoulders and made her look like “the girl next door” in every movie.
Elizabeth was Ryan’s stepsister. When Ryan was seven and Liz was six, their parents had met on an outdoor group hike. The two had quickly discovered a mutual fondness for camping and music, and compatible politics had made for an easy transition from friends to dating, and then to marriage. Both Liz and Ryan had been wary at first, but they both found it hard not to genuinely like their stepparents.
As for one another, Ryan had been fine with Liz. He was already more of an introvert, and at age seven he was a quiet kid who spent better than half his time in his room. As he got older, that continued, with him preferring to spend his time learning to program, watching movies, and running, all things he could do without having to talk when he didn’t feel like it. Liz hadn’t had much in common with her new sibling, and was much more social, so she spent most of her time with friends playing, gossiping, and navigating the dangerously hostile waters of teen girls in middle and high school.
Liz liked Ryan, who had always been willing to help her if she needed a homework assignment checked, and on the one occasion a boy at school had started harassing her, he had told the kid that if he didn’t leave her alone that he would beat the snot out of him. Ryan wasn’t a jock or even intimidating, but the threat was so far out of character that the younger boy backed off immediately.
Two years ago, when Liz had started showing curves, she had decided to quit jogging on her own after a guy had yelled something out a window at her. The incident had rattled her mother, and it had shaken Liz a bit, too, as she realized how empty their suburban neighborhood could be. She had asked Ryan if he would mind her running with him, and the two would go out 4 or 5 times a week and run a few miles just to keep in shape.
Liz had matured into a very attractive young woman. She kept her hair in a braid, wearing it down only when she wanted to make an impression. Her body was made to rock a bikini, and the running kept her legs toned and muscular. Boys lined up to date Liz, but she rarely went out with them, preferring to focus on school. Chem textbooks didn’t try to grab your boobs during a movie, and they didn’t act like morons around their friends.
“Liz, you actually let them do this to me?” Ryan asked, genuinely surprised. “Why? I thought we were cool.”
“We ARE cool, but they were gonna do this whether I was on board or not. Do you really want let them have total control over you without me to keep them from going too far?” Liz looked a bit ashamed as she answered, but she was still standing there.
“Keep them from going too far? Like, you know, taking naked pics of your brother and blackmailing him?” Ryan asked, disbelieving. “How much farther can you go than that?”
“Look, just play along with them and I promise they will delete all the pics. I’ll make sure of it.”
“Just pay along, Liz? Are you kidding me?”
“Ryan, I know this is weird, ok, but all of us were talking after the game—you know, about boys and THAT (she pointed to his crotch), and someone said, “hey, we have a good-looking guy right here, and if we could make him, we could have him show us everything!”
Jessica piped up, “We knew you wouldn’t go for it—you’re so shy and all—but you really should be kinda flattered that you have all these girls here wanting to check you out because they think you’re hot..”
“And you guys pull this sort of shit all the time with us,” Sarah said. “You’re always staring, trying to get us undressed, and you flip out if we say no and dump us or lie about it or whatever so you can be “cool” with your friends,”
“Yeah—you guys owe us,” chimed in Cassie.
Ryan looked around the room at the girls. “And you all feel this way? You’re all fine with doing this to me, threatening to put my photos
In the hands of all my classmates? Blackmailing me? That’s just fine?”
Cassie giggled. “It looked pretty fine to me!”
“Is it nice of us? No. But it is what it is, Ryan,” Sarah said. “We have you, and if you don’t play ball, we’ll make sure everyone else has you too.”
“Liz,” Ryan said to his stepsister, “do you really want to do this? You could walk away, let me go…”
Liz shook her head. “I can’t. These are my girls, and I’m sorry, but I can’t choose you over them.”
Ryan shrugged. “I tried. Okay, you want to see me? Take a good look.” He threw back his sheet, exposing himself fully, and hurried to his dresser, quickly pulling on a pair of boxers.
“Bad boy!” Sarah scolded. “We didn’t tell you you could cover up. I think that’s going to require some punishment.”
Ryan ignored her and walked over to his closet door. He threw it open, revealing the camera inside. He then went to his desk, peeling the electrical tape off that was covering up the “active” light on his laptop. He then brought the brightness up on the screen, and a clear image of about half the girls and Ryan’s bed was visible on the screen. Finally, he reached under the bed and pulled out a small broadcasting microphone.
“So you want to play blackmail, huh? Well, I think we can play, but I have a few different rules,” Ryan said to the stunned group of teens.
***
It had started with a game of Truth or Dare.
Well, actually, it had started earlier than that, when Liz had casually mentioned that Jessica had said he was really cute during one of their runs together. Ryan had acted like he thought Liz was joking with him, but the thought that one of Liz’s hot friends was into him was enough to make him hard right then and there. If Liz had noticed, she hadn’t said anything, but from then on Ryan had started paying a lot more attention to Liz’s friend group, and had started trying to figure out the individual girls. The more he watched, the more he noticed them checking out his lean body or how they often would “just happen” to be running at the same time as he and Liz.
When he finally became convinced that there was something there, and that the girls weren’t playing some sort of elaborate prank on him designed to humiliate him, Ryan started thinking about what to do. He needed to know more before he could ask any of them out. Which one was the most interested? What did they like about him? What did they look for in a guy? He read articles on picking up on women’s signals, and he read books about how to catch a girl’s eye, but it was all too vague for him. He needed something more. He needed hard data.
It was a fairly simple matter to plant the wireless microphone in his sister’s room. It was a “mouse”, a mike usually used for theater productions, and he had no problem snagging one from the school. Since they were black already, they tended to disappear in the dark, and so he taped it to the inside of Liz’s closet, above the accordion doors, where it fit nearly perfectly above a piece of the door frame. Liz almost always had her closet open - neat was NOT her thing - and so the next time Liz had one of her friends by, Ryan was able to listen in on their conversations.
90 percent of it was tedious and dull. However, that last 10 percent had been more than enough for him to figure out that almost all the girls - his stepsister included - were largely inexperienced with boys. A couple had kissed, and Cassie admitted to having been felt up under a blanket on the band bus by her ex-boyfriend one night on the ride home, but beyond that, they were still in the dark. Sure, they had seen pictures of male anatomy, some quite explicit, but they hadn’t had any sort of personal experience. And they clearly were interested.
It wasn’t until the last time Liz had some of her friends sleep over that the idea had formed. Jessica and Cassie had convinced the others to play Truth or Dare, and at one point, Cassie had been dared to walk into Ryan’s room and, without a word, French kiss him. Cassie had taken a truth instead, and had admitted that the thought of kissing him kind of turned her on, but that she didn’t want him to think she was a skank who jumps anything around her. Then she had turned on her friend, Sarah, who had given the dare, and dared her to either flash Ryan or to get Ryan to flash her. She, too, took a truth, but when asked “If you could see anyone at school naked, who would you choose?” she apparently refused to answer, and was “punished” for it by having to spend the next round naked and unable to cover up. It was tempting for Ryan to barge in on some pretext at that point, but he had already started to hatch a plan in his mind.
The next time Liz had her friends over, Ryan had made a point of taking off his shirt and mowing the lawn outside. His sweaty, lean body wasn’t muscular, but it wasn’t the opposite either. When he checked the recording after taking a shower, he heard several of the girls complimenting his physique, and a couple who would have loved to see him all soaped up in the shower. Ryan played on this interest, coming down after his shower and chatting with all the girls. When Jessica, ever the risk-taker, had suggested they play Truth or Dare and invited him to join - and no one objected - he felt pretty sure about the accuracy of his prediction. He teased the girls just enough by deliberately taking a couple of dares that showed him off to his best advantage. But would they crack?
Yes, as it turned out– they would.
A Small Price To Pay (Poll-what happens next?)
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Fred Key
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A Small Price To Pay (Poll-what happens next?)
Last edited by Fred Key on Mon Sep 18, 2023 4:16 pm, edited 14 times in total.
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Fred Key
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Re: A Small Price To Pay (Ch. 2 6/16)
Chapter 2 - Reversal of Fortune
The Truth or Dare game had gone pretty much as Ryan had hoped. It was clear from early on that the girls were ganging up on him, as he was the recipient of almost every other question or dare. Ryan had decided that the right way to play it was to be “reluctant” about the truths - answering, but making sure he had just a bit of shame or discomfort in his voice, and making sure that when he made eye contact with a girl he looked away immediately. He wanted them to see him as timid and uncertain. When Cassie bluntly asked him how often he jerked off, he didn’t need to work hard to seem embarrassed, but he answered “maybe once every day or two”, and the girls squeals of laughter at his confession made him turn even redder. “Eww! TMI!” said Liz, rolling her eyes.
The dares were even easier to play. When he was dared to take off his shirt and flex, he did it, but made a big show of reluctance, even turning around to take the shirt off facing away from the girls. He overhead one of them (Annie?) whisper to Sarah, who had dared him, “I’m not doing stripping dares! Ease up!”, but pretended not to notice. Of course, when it was his turn next, he looked around, then fixed on Cassie and said, “I ought to dare YOU to take off your shirt and flex, but I don’t want this to get out of hand. I dare you to…do ten star jumps!” Cassie had been embarrassed enough to do those, her breasts bouncing as she threw her body up and into the jumps like she did at practice. Ryan’s erection had been almost immediate.
When Liz had dared Cassie to kiss Ryan, he had let her take the lead, not initiating anything, but following her. She had boldly stepped into a kiss with him, flipping off Liz at the same time, but she kept her tongue in her mouth, just barely licking along his lips. He had also made a point of giving her a wide-eyed “Whoa. Uh…thanks!” after, which made Cassie smirk.
In other words, he had played the innocent, hopeless, passive, safe guy. The guy that the girls could trust. Could count on. The guy who was kind of hot, but didn’t realize he was hot, and who wasn’t all that sharp. The kind who, after a few rounds, excused himself saying “I…I think I better go. I have to wank up early tomorrow–I mean wake up–oh, fuck!” and scurrying out of the room to peals of female laughter.
He listened in to the girls on his hidden mic afterwards as they changed for bed up in Liz’s room. “I bet he had to wank up!” Cassie crowed.
“Ugh! Stop it! He’s my brother!” Liz said.
“Did you see his pants? He was pitching a tent there for sure!”
“I’d go camping there!”
“GROSS!!”
“Oh, come on…I wish he would have played a little longer. I was all set to dare him to take off those pants.”
“Seriously…I wonder what it looks like!” Jessica giggled. “You think it’s like those porn guys?”
“No, those guys are freaks,” Sarah replied. “I bet it’s small the way he kept backing down on everything.”
“It looked big enough to me,” Jessica retorted. “You could see it poking out like, three inches or something!”
“You know…” Cassie said quietly, “We could find out…”
Silence. Sarah was the first to speak. “What are you talking about, Cassie?”
“We could find out. We wait until he goes to sleep, sneak into his room, and we check him out.”
“Just sneak into his room and pull down his pants? Oh, that’s a GREAT idea,” Annie said. “No issues there.”
“Hear me out,” Cassie said. “I’ve got my sleeping pills–you know, the ones for my insomnia? We put one in a Coke or something so he’s totally out. Then we go in and look for ourselves. He won’t even know we’re there.”
“You want to DRUG my brother?” Liz asked in disbelief.
“I’m not talking about giving the guy a roofie, Liz. Just knocking him out.”
“NO. Absolutely not. That’s like rape.”
“Ok, Ok,” Cassie said. “Don’t get your panties in a knot, Liz. But you have to admit that Ryan could use a little confidence in the sex department. The guy isn’t half-bad looking, but he’s gonna be a virgin forever. He’s too scared to do anything.”
“It would almost be a service,” Jessica said impishly. “We could get him over some of his hang-ups. If he saw that we thought he was really sexy naked, he might be more self-confident!”
“I can’t believe I’m hearing this conversation,” grumbled Liz.
“Ok, no drugs–but what about this? Does your brother wear pajamas to bed?” Cassie asked.
“Um…no, he wears his boxers most of the time, I think. He’s always complaining how hot it is in the house this time of year,” Liz replied.
“Good. We sneak in, we lift his sheet, and we get a couple of pics. Maybe something is showing! Then we wake him. We tell him that he’s gotten our attention after the Truth or Dare game, and that we want to see what he’s packing under there. If he won’t show us, we tell him about the pictures. We get a good look, and then we delete everything.”
“For fuck’s sake, Cassie! You’re talking about blackmailing him with dick pics?” Liz said disbelievingly. “If a guy did this you’d be ready to castrate him!”
“Look, it isn’t the same. I’d even help him out a bit with his problem as a thank you - you know, give him a handjob or something. Tit for tat, but without the tits,” she joked. “Do you really think Ryan would be upset about getting jacked off by four of his sister’s hot friends? That’s, like, a boy fantasy.”
“She’s right,” Sarah said. “He’ll probably cream himself just seeing Annie in that nightshirt.”
“What’s wrong with my nightshirt?” Annie asked.
“Nothing…and nice panties, by the way,” Sarah replied.
“Seriously? Fuck! You guys…”
“Oh, calm down, Annie, she’s pulling your leg.”
“Well, I’M not pulling anyone’s anything,” Annie retorted.
“I’ll do it,” Cassie said. “I want to know what it feels like.”
The conversation went on from there, but Ryan was already thinking through his next moves. It didn’t take long for him to decide on a plan to turn the tables on the girls if they went through with their plan. Sure, it would mean letting them see him naked, but he was willing to trade a few minutes of being naked in front of them for control over the five. He would have plenty of time to get over his exposure, and make sure everyone else know that sharing pics of him would be a disaster.
He began placing equipment around his room and hiding it. Then he shucked off his boxers, climbed into bed, and began to wait.
***
Liz stared at the camera, its red light blinking, and at the newly revealed green light at the top of Ryan’s laptop–clearly signifying the camera was active. He has it all on tape! Fuck! We are totally screwed!
“So you want to play blackmail, huh? Well, I think we can play, but I have a few different rules,” Ryan said to the stunned group of teens. Cassie was looking at him with her mouth open, still staring at his dick. It was clearly the largest she’d seen, not that she had much experience in that department. Jessica was standing silently, but her eyes showed the fear she was feeling. Annie fell back against the wall in stunned silence.
Sarah tried to put a tough front on. “You think that a few grainy pics of us in your room is going to matter? We’ll just tell everyone the truth - that you invited all of us to come up and wanted it to be a surprise. Who’s going to believe that five girls tried to blackmail an older guy?”
Ryan looked back at her, meeting her gaze squarely. “I think that the recording will persuade them,” he said. “The part about drugging me? That’s a felony right there.”
Cassie went white as a ghost. “How do you…”
Liz looked at him in disbelief. “Were you SPYING on us, Ryan?”
“I wasn’t,” he lied. “I just guessed. But…I think that threatening me with even more abuse is pretty ballsy, especially after getting caught like this. In fact, I think that it deserves some punishment.”
“Punishment?” Annie asked nervously.
“Punishment. For Sarah, specifically, since she seems to believe she has all the answers.” He walked over to the teen, who shrank away a bit. Snatching her arm, he pulled a protesting Sarah over to his bed and threw her across his lap. She struggled, threatening him the whole time. He ignored her, and she continued to rant at him until she froze instantly. Ryan had seized her PJ bottoms and the waistband of her underpants.. He’s not going to… she thought, redoubling her struggles, but he absolutely WAS, and did pull them down to her knees. Her bright, unmarred backside was now bared to the window as well, and she wailed in embarrassment as he adjusted her a bit more. Finally, her bare bottom was right where he wanted it, and he brought his hand down with a thundering SMACK!
“OW!”
*SMACK*
“OH! FU-”
*SMACK!!
“YEOWCH! Ow, please, please, Ryan–”
Ryan paused, and Sarah breathed a sigh of relief. “Oh, god…”
Ryan looked at her lightly pink backside. Not bad for three spanks, he thought to himself, but I can do a LOT better.
For the next five minutes, that’s exactly what he did. Ignoring the yells of protest from Sarah, he methodically set about turning her backside a bright red from the tops of her sit-spots to the bottom of her waist. When he finally stopped, he looked up at the rest of the girls, who were all pressed against the wall as if they were sheep trying put as much distance between them and a mountain lion as possible.
“This is only the beginning, ladies. Each of you is going to get a turn over my lap, and then we’ll get started with the REAL punishment.”
The Truth or Dare game had gone pretty much as Ryan had hoped. It was clear from early on that the girls were ganging up on him, as he was the recipient of almost every other question or dare. Ryan had decided that the right way to play it was to be “reluctant” about the truths - answering, but making sure he had just a bit of shame or discomfort in his voice, and making sure that when he made eye contact with a girl he looked away immediately. He wanted them to see him as timid and uncertain. When Cassie bluntly asked him how often he jerked off, he didn’t need to work hard to seem embarrassed, but he answered “maybe once every day or two”, and the girls squeals of laughter at his confession made him turn even redder. “Eww! TMI!” said Liz, rolling her eyes.
The dares were even easier to play. When he was dared to take off his shirt and flex, he did it, but made a big show of reluctance, even turning around to take the shirt off facing away from the girls. He overhead one of them (Annie?) whisper to Sarah, who had dared him, “I’m not doing stripping dares! Ease up!”, but pretended not to notice. Of course, when it was his turn next, he looked around, then fixed on Cassie and said, “I ought to dare YOU to take off your shirt and flex, but I don’t want this to get out of hand. I dare you to…do ten star jumps!” Cassie had been embarrassed enough to do those, her breasts bouncing as she threw her body up and into the jumps like she did at practice. Ryan’s erection had been almost immediate.
When Liz had dared Cassie to kiss Ryan, he had let her take the lead, not initiating anything, but following her. She had boldly stepped into a kiss with him, flipping off Liz at the same time, but she kept her tongue in her mouth, just barely licking along his lips. He had also made a point of giving her a wide-eyed “Whoa. Uh…thanks!” after, which made Cassie smirk.
In other words, he had played the innocent, hopeless, passive, safe guy. The guy that the girls could trust. Could count on. The guy who was kind of hot, but didn’t realize he was hot, and who wasn’t all that sharp. The kind who, after a few rounds, excused himself saying “I…I think I better go. I have to wank up early tomorrow–I mean wake up–oh, fuck!” and scurrying out of the room to peals of female laughter.
He listened in to the girls on his hidden mic afterwards as they changed for bed up in Liz’s room. “I bet he had to wank up!” Cassie crowed.
“Ugh! Stop it! He’s my brother!” Liz said.
“Did you see his pants? He was pitching a tent there for sure!”
“I’d go camping there!”
“GROSS!!”
“Oh, come on…I wish he would have played a little longer. I was all set to dare him to take off those pants.”
“Seriously…I wonder what it looks like!” Jessica giggled. “You think it’s like those porn guys?”
“No, those guys are freaks,” Sarah replied. “I bet it’s small the way he kept backing down on everything.”
“It looked big enough to me,” Jessica retorted. “You could see it poking out like, three inches or something!”
“You know…” Cassie said quietly, “We could find out…”
Silence. Sarah was the first to speak. “What are you talking about, Cassie?”
“We could find out. We wait until he goes to sleep, sneak into his room, and we check him out.”
“Just sneak into his room and pull down his pants? Oh, that’s a GREAT idea,” Annie said. “No issues there.”
“Hear me out,” Cassie said. “I’ve got my sleeping pills–you know, the ones for my insomnia? We put one in a Coke or something so he’s totally out. Then we go in and look for ourselves. He won’t even know we’re there.”
“You want to DRUG my brother?” Liz asked in disbelief.
“I’m not talking about giving the guy a roofie, Liz. Just knocking him out.”
“NO. Absolutely not. That’s like rape.”
“Ok, Ok,” Cassie said. “Don’t get your panties in a knot, Liz. But you have to admit that Ryan could use a little confidence in the sex department. The guy isn’t half-bad looking, but he’s gonna be a virgin forever. He’s too scared to do anything.”
“It would almost be a service,” Jessica said impishly. “We could get him over some of his hang-ups. If he saw that we thought he was really sexy naked, he might be more self-confident!”
“I can’t believe I’m hearing this conversation,” grumbled Liz.
“Ok, no drugs–but what about this? Does your brother wear pajamas to bed?” Cassie asked.
“Um…no, he wears his boxers most of the time, I think. He’s always complaining how hot it is in the house this time of year,” Liz replied.
“Good. We sneak in, we lift his sheet, and we get a couple of pics. Maybe something is showing! Then we wake him. We tell him that he’s gotten our attention after the Truth or Dare game, and that we want to see what he’s packing under there. If he won’t show us, we tell him about the pictures. We get a good look, and then we delete everything.”
“For fuck’s sake, Cassie! You’re talking about blackmailing him with dick pics?” Liz said disbelievingly. “If a guy did this you’d be ready to castrate him!”
“Look, it isn’t the same. I’d even help him out a bit with his problem as a thank you - you know, give him a handjob or something. Tit for tat, but without the tits,” she joked. “Do you really think Ryan would be upset about getting jacked off by four of his sister’s hot friends? That’s, like, a boy fantasy.”
“She’s right,” Sarah said. “He’ll probably cream himself just seeing Annie in that nightshirt.”
“What’s wrong with my nightshirt?” Annie asked.
“Nothing…and nice panties, by the way,” Sarah replied.
“Seriously? Fuck! You guys…”
“Oh, calm down, Annie, she’s pulling your leg.”
“Well, I’M not pulling anyone’s anything,” Annie retorted.
“I’ll do it,” Cassie said. “I want to know what it feels like.”
The conversation went on from there, but Ryan was already thinking through his next moves. It didn’t take long for him to decide on a plan to turn the tables on the girls if they went through with their plan. Sure, it would mean letting them see him naked, but he was willing to trade a few minutes of being naked in front of them for control over the five. He would have plenty of time to get over his exposure, and make sure everyone else know that sharing pics of him would be a disaster.
He began placing equipment around his room and hiding it. Then he shucked off his boxers, climbed into bed, and began to wait.
***
Liz stared at the camera, its red light blinking, and at the newly revealed green light at the top of Ryan’s laptop–clearly signifying the camera was active. He has it all on tape! Fuck! We are totally screwed!
“So you want to play blackmail, huh? Well, I think we can play, but I have a few different rules,” Ryan said to the stunned group of teens. Cassie was looking at him with her mouth open, still staring at his dick. It was clearly the largest she’d seen, not that she had much experience in that department. Jessica was standing silently, but her eyes showed the fear she was feeling. Annie fell back against the wall in stunned silence.
Sarah tried to put a tough front on. “You think that a few grainy pics of us in your room is going to matter? We’ll just tell everyone the truth - that you invited all of us to come up and wanted it to be a surprise. Who’s going to believe that five girls tried to blackmail an older guy?”
Ryan looked back at her, meeting her gaze squarely. “I think that the recording will persuade them,” he said. “The part about drugging me? That’s a felony right there.”
Cassie went white as a ghost. “How do you…”
Liz looked at him in disbelief. “Were you SPYING on us, Ryan?”
“I wasn’t,” he lied. “I just guessed. But…I think that threatening me with even more abuse is pretty ballsy, especially after getting caught like this. In fact, I think that it deserves some punishment.”
“Punishment?” Annie asked nervously.
“Punishment. For Sarah, specifically, since she seems to believe she has all the answers.” He walked over to the teen, who shrank away a bit. Snatching her arm, he pulled a protesting Sarah over to his bed and threw her across his lap. She struggled, threatening him the whole time. He ignored her, and she continued to rant at him until she froze instantly. Ryan had seized her PJ bottoms and the waistband of her underpants.. He’s not going to… she thought, redoubling her struggles, but he absolutely WAS, and did pull them down to her knees. Her bright, unmarred backside was now bared to the window as well, and she wailed in embarrassment as he adjusted her a bit more. Finally, her bare bottom was right where he wanted it, and he brought his hand down with a thundering SMACK!
“OW!”
*SMACK*
“OH! FU-”
*SMACK!!
“YEOWCH! Ow, please, please, Ryan–”
Ryan paused, and Sarah breathed a sigh of relief. “Oh, god…”
Ryan looked at her lightly pink backside. Not bad for three spanks, he thought to himself, but I can do a LOT better.
For the next five minutes, that’s exactly what he did. Ignoring the yells of protest from Sarah, he methodically set about turning her backside a bright red from the tops of her sit-spots to the bottom of her waist. When he finally stopped, he looked up at the rest of the girls, who were all pressed against the wall as if they were sheep trying put as much distance between them and a mountain lion as possible.
“This is only the beginning, ladies. Each of you is going to get a turn over my lap, and then we’ll get started with the REAL punishment.”
Last edited by Fred Key on Mon Jun 26, 2023 10:31 pm, edited 1 time in total.
Re: A Small Price To Pay (Ch. 2 6/16))
Great story so far. Reminds me of some of the best oldies on GetDare. I normally don't comment but I rarely see a story that gets me excited just from the intro. I personally am a big fan of classic setups like these, and Truth or Dare with the sister's hot friends might just be my favorite ENF trope. Really hoping he takes full advantage of them, and don't be afraid to indulge us with lots of details!
Re: A Small Price To Pay (Ch. 2 6/16))
Youre really on a roll with this and the tutor. Idk how your making these setups so good im excited before the end of the first post. Also appreciate you spicing it up with the spanking, great work
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Fred Key
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Re: A Small Price To Pay (Ch. 2 6/16))
Chapter 3 - The pain you know
Sarah was still moaning “OW! OW! OH!” and desperately rubbing her flaming backside a minute after Ryan had let her up from his lap. Her pajama pants and pink panties were still in a puddle around her ankles, and the only concession she made to modesty was to turn away from Ryan, which suited him just fine - he was perfectly content with seeing her bright red butt at the moment as a reminder of how firmly in charge he was.
“Who’s next?” he asked, looking at the other four girls. They all looked at each other as if this was a trick question or as if one of them was going to nobly step up and offer to take the punishment for the other three as well as for herself. Unfortunately for the four, this was real life, and none of the girls was particularly eager to put herself where Sarah had been moments ago - certainly not with Sarah, who had always been the more aggressive of the group members, so clearly cowed.
Ryan pointed to Cassie. “OK, Cassie, let’s go.”
Cassie, who had proven herself more spunky than most would have thought, shook her head and waved her phone. “I don’t think so. Remember this? Ok, you may have us on tape, but we have you and your dick on camera. That seems like a standoff to me. You don’t share and we don’t share.”
Nice try, Ryan thought. Would have been disappointing if no one had at least made the effort, really. “That would make sense if I actually trusted any of you, I suppose. It isn’t like I want you spreading those pics everywhere. The problem is that I don’t trust any of you. I mean, seriously? You snuck into my room, took nude pics of me, threatened me with blackmail, and generally crossed every line you can tonight. Why would I believe for a minute that you won’t share those with your friends? For that matter, why would I be ok with letting all of you keep them? Forget it. That ship has sailed.”
“I can send these to the entire school with two emails,” Cassie warned.
Ryan sighed. “Cassie, you aren’t listening. As far as I’m concerned, there’s nothing I can do to KEEP you from doing that. This isn’t about me keeping my privacy anymore. That’s out of my control. This is now about whether I take this tape of you five to your parents–OUR parents, Liz–to the school board, or to the police.”
“Ryan! You can’t!” Liz said incredulously. “Mom and Dad would disown me!”
Annie was looking panicked. “The police? Over a little prank?”
“I’m pretty sure that you leave prank behind around blackmail,” Ryan snapped. “And don’t forget your coach, Annie–bet she’ll love the publicity for the lacrosse team.”
Now Cassie looked a lot more nervous. “What if we let YOU delete the pictures from our phones? Then you’d know you were in the clear.”
Ryan shook his head again. “How would I know you didn’t already save them to the cloud? Besides, it seems like a pretty uneven swap - you see me naked, and I just delete the pictures and move on.”
Still rubbing her sore butt, Sarah snarled, “What, you think WE should all get naked for YOU? Keep dreaming.”
Ryan looked Sarah up and down, then chuckled. “Frankly, I don’t think that seeing you naked would be much of a dream.” Sarah sputtered angrily, crossing her arms instinctively. While she had always had multiple boys vying for her attention, she had also long been highly self-conscious about her chest. Her breasts were A cup, and while they suited her skinny torso, she had endured plenty of itty-bitty-titty jokes through middle school.
Ryan turned his attention back to Cassie. “So - your call. Either you get yourself over here across my lap, or you start planning how you’re going to answer the reporters when they get a hold of this story.”
Cassie looked to her friends. Jessica’s usual grin was gone, replaced by a very serious expression. “He’s not joking, Cass. Besides, you said it yourself - he’s hot. You know that pics of his cock would be embarrassing, but how many girls would he suddenly have the attention of? You were all but drooling.”
“Jessica!”
“It’s true!” her friend continued. She looked at the other girls. “I don’t know about you guys, but as far as I’m concerned, he’s got all the high cards.” She looked to Ryan now. “OK. You win. You can fuck up our lives. So how do you propose we get out of this situation? I mean, the same thing you said applies to us, too - if there’s no way for us to know that you’ll get rid of those tapes, we might as well take our chances, right? So what do you have in mind?”
Ryan nodded. He hadn’t really figured Jessica would be the one to cut to the chase, but he liked her for being honest. “Like I said - I’m going to give each of you a spanking to start with, and then we’ll talk actual punishment.”
Now it was Jessica’s turn to shake her head. “Nope. Not good enough. We get all of the terms out on the table, right here and now, or we all take our chances.”
“Jessica, what are you DOING?” Liz hissed. “Don’t piss him off more!”
“I’m not going to piss him off more,” Jessica said calmly. “But I’m not going to be his slave for the rest of my life, either. We’re going to agree to terms, and then we’ll deal with it.” She turned back to Ryan. “I’m assuming that there’s no way we can get out of this with a simple spanking, right? It would mean you get to see everyone’s bare asses, plus there’s got to be some value in getting to lord it over five good looking girls.”
“Much as I plan to enjoy spanking each of you, that’s not going to be enough for me to give you the tapes. I suppose that sex with the four of you – NOT you, Liz, that’s just wrong – would be off the table as well?”
Annie looked like she was going to be sick. “You’re fucking right that’s off the table!” Cassie said angrily. “Not gonna happen!”
Ryan raised his hands in surrender. “I didn’t expect it would. So somewhere in between, then.”
“Somewhere between,” Jessica nodded. She took a deep breath. “Okay - how about you get your spankings, and then you get to see each of us naked?”
There was an eruption of noise as several of the girls began shouting objections at once.
“There’s no way!”
“I’m not getting naked in front of my STEPBROTHER!” Liz protested.
“I’m not either!” Annie agreed.
“SHUT UP!” Jessica yelled, and suddenly everyone was quiet.
The army brat looked around at the others. “You guys better get real about this QUICK. What part of ‘he can have us arrested’ are you not following? Look, I don’t like this any more than you do, and I think it’s pretty fucking clear that Ryan trapped us, but the bottom line is that WE FUCKED UP. We were the ones who came into his room, and we were the ones who tried to blackmail him.” She shook her head, smiling ruefully. “It’s always the boys who are being pulled around by their dicks, right, but we were just as stupid horny as they are this time. All it took was one good looking guy and the thought that we might get a look at him naked and we turned into idiots.”
She turned back to Ryan. “Like I said - spankings for each of us, plus you get a look at us naked. Deal?”
“No, no deal,” Ryan answered. “You make a pretty good case for me, Jessica. You’d count yourself lucky if I took that offer, wouldn’t you? No, here’s how this is going to work, and you can take it or leave it. No one is going to be here but us until around noon tomorrow, which gives me a whole night and morning to enjoy. I’m willing to agree that actual sex is off the table. I’m not even going to demand total control over you.”
“Then what?” Jessica asked.
“Then we’re going to play a few games. I’ll set the games and the rules. Each game will have one loser, and that loser will have to perform a punishment I set. The winner will also get a prize - she will get to pick one other girl to join the loser in taking the punishment for that game. We play five games, and after that, we’re even. I’ll delete my videos, and you delete yours.”
“Wait,” Annie asked hopefully. “Doesn’t that mean that if we win all the games, we could get out without any extra punishment beyond the spanking?”
“That’s possible, yes,” Ryan answered with a smile. “You could get that lucky.”
The tall girl pulled on her ponytail. “And you promise that you’ll delete the tape?”
“That’s the deal,” he replied.
“But how do we know we can trust YOU?” Sarah asked angrily. “You set all this up!”
“We don’t know,” Jessica answered.
Liz looked at Ryan. “Ryan - I know that this was totally wrong of me to let happen. I get that. I’m even….I guess….willing to accept that we deserve some sort of punishment for that. I want your word, though, that those tapes go away if we agree to this. I know you aren’t a liar. If you say you’ll do this, you will. So, do we have your word?”
“You do,” Ryan said. “And nothing about what happens here will ever be talked about by me.”
Liz looked at the other girls. “He really doesn’t lie,” she said. “If he says it, he means it.”
“This is as good a deal as we’re going to get,” Jessica agreed. “We should take it.”
“No!” Sarah retorted. “I am NOT letting him do ANYTHING to me.”
“You are,” said Jessica firmly. “If everyone else is on board, you’re in too. All of us or none. If you try to bail on us, Sarah, we’re done with you. You take your lumps with the rest of us, or you can explain to the rest of the school when we tell them you ditched on your friends.”
No one else objected. Sarah growled, then said, reluctantly, “Fine. Whatever.”
“OK, you have your deal,” Jessica said, sighing.
“Cassie,” Ryan said, turning back to the girl, who was now wearing a look of resignation. “I think we were about to take care of some business here?”
The petite brunette shuffled over reluctantly to his side, and Ryan patted his lap. Cassie lowered herself over, carefully avoiding letting her breasts brush his legs, but then she gave a sudden yelp of surprise as she felt something poke her in the groin. “What’s the matter?” Ryan asked innocently.
“Your…your dick!” Cassie blushed furiously. “It’s poking me…You know what’s wrong!”
“A few minutes ago you were ready to blackmail me with pictures of my dick, and now you’re upset that it’s hard? Would you rather have it poking you this way, or would you prefer I poke you somewhere else, Cassie? I could be flexible about this. But to be honest,” he said, “I’d just as soon stick with this spanking for the moment.” Ryan rubbed the girl’s tight little bottom, watching her squirm under his touch. “I don’t think many people realize what an amazing ass you have, Cassie. I do, though. You sat in front of me in Spanish last year, remember? I loved football Fridays, because that meant you were in that spandex color guard gear, and I could stare all period long. You never noticed, did you?”
Cassie’s brain was whirling. On the one hand, there was Ryan’s hand, which was currently rubbing her bottom as if that was perfectly normal, letting his fingers slip into the shallow space left between her cheeks, which she had clenched as tightly as she could. On the other hand, RYAN’S hand was on her butt, and it felt so NICE the way he was rubbing, and he said he had been staring ALL SEMESTER at HER. No one stared at her. And now his fingers… “HEY!” she squealed as Ryan’s hand slid under her shorts and over her cotton panties. Cassie tried to roll off, but he easily pinned her in place with one leg across her own and his other hand holding her shoulder firmly. She struggled, but even as she did, she felt warmth spreading from between her legs. Everywhere his fingers slid, little lines of heat sparked across her bottom, and she gasped as they brushed just close enough to the juncture of her thighs to send a tingle through her body.
Before she could do anything, however, Cassie felt herself tip forward, and was barely able to get her hands out to catch herself and keep from hitting her head. Her butt was now right on the edge of Ryan’s lap, and her thighs flat and vulnerable. It was the PERFECT position if you wanted to maximize the impact and embarrassment of a spanking, at least as soon as…
Cassie moaned as she felt her shorts come down. Now only her black and white striped panties were protecting her modesty, and she was acutely aware that at this angle, Ryan would have NO problem seeing everything. “Oh, god - Ryan, please let me keep my panties! Please!”
“Um….no.” Ryan’s words were followed by a quick tug, and Cassie could only whimper as her secrets were completely revealed to him. “But don’t worry - I’ll give you a distraction so you don’t have to think about how you’re on display for me.”
Before Cassie could utter a word, the echoes of a firm-handed spanking once again filled the room. Cassie wept and clutched at Ryan’s leg, but nothing slowed the assault on her tiny derriere. The warmth that had been between her legs was now replaced by a fire across the surface of her butt and thighs that was intensifying by the second. Cassie grit her teeth, willing herself not to give in to the pain, but it was only a short minute or two before the girl began weeping openly and pleading for mercy.
SMACK! SMACK! SMACK!
The taut flesh of Cassie’s bottom was now burning, and each repeated slap to her wobbling cheeks added fuel to the bonfire. Then suddenly the spanks stopped coming, and there was just Ryan’s hand rubbing her gently, back and forth, massaging the sting from her backside. She gulped down a sob and tried to breathe, ignoring the fact that a boy was currently feeling up her ass and focusing on the pleasure of the touch against her skin.
CRACK!
The unexpected sound made Cassie’s head pop up for just a second, looking around for the source of the noise. Then her bottom registered that the noise had been the impact of a hairbrush against her left cheek, and a howl of agony made the other girls in the room wince. A second CRACK! against the right globe of her tiny tush drew the same response, and from there it was simply a question of how much noise Cassie could produce before her voice gave out entirely. Each successive blow of the wooden implement seemed to increase both the volume and the pitch of her cries. Cassie tried to beg for Ryan to stop, but she couldn’t catch enough of a breath to speak. She bawled like she hadn’t bawled in years, not since the last time her own father had lit her backside on fire when he caught her messing around with his power tools.
After what seemed to Cassie to be a month, the rain of pain finally stopped. Cassie blubbered on, unable to even try to lever herself up from across Ryan’s lap. He rubbed her back and waited for her to get control of herself, and Liz eventually brought her a washcloth, which Cassie gratefully used to wipe down her tear-lined face. She gingerly pulled up her panties, wincing as the cloth brushed against the painfully inflamed skin, and opted to leave her shorts off rather than add any more pressure back there. She looked at Ryan, meek and chastised. “I’m sorry. Really sorry. I was wrong, and I…I deserved the spanking.”
Ryan nodded approvingly. He looked at the three remaining girls, then pointed to Jessica. “You took charge, so I guess you’re up next.”
Jessica nodded, trying to maintain her composure, and stepped forward. “Ok. I’m ready.” This part is going to be the easy part, she thought to herself. The pain you know isn’t what gets you. She wondered if the second half of the night would be as straightforward as this.
She doubted it.
Sarah was still moaning “OW! OW! OH!” and desperately rubbing her flaming backside a minute after Ryan had let her up from his lap. Her pajama pants and pink panties were still in a puddle around her ankles, and the only concession she made to modesty was to turn away from Ryan, which suited him just fine - he was perfectly content with seeing her bright red butt at the moment as a reminder of how firmly in charge he was.
“Who’s next?” he asked, looking at the other four girls. They all looked at each other as if this was a trick question or as if one of them was going to nobly step up and offer to take the punishment for the other three as well as for herself. Unfortunately for the four, this was real life, and none of the girls was particularly eager to put herself where Sarah had been moments ago - certainly not with Sarah, who had always been the more aggressive of the group members, so clearly cowed.
Ryan pointed to Cassie. “OK, Cassie, let’s go.”
Cassie, who had proven herself more spunky than most would have thought, shook her head and waved her phone. “I don’t think so. Remember this? Ok, you may have us on tape, but we have you and your dick on camera. That seems like a standoff to me. You don’t share and we don’t share.”
Nice try, Ryan thought. Would have been disappointing if no one had at least made the effort, really. “That would make sense if I actually trusted any of you, I suppose. It isn’t like I want you spreading those pics everywhere. The problem is that I don’t trust any of you. I mean, seriously? You snuck into my room, took nude pics of me, threatened me with blackmail, and generally crossed every line you can tonight. Why would I believe for a minute that you won’t share those with your friends? For that matter, why would I be ok with letting all of you keep them? Forget it. That ship has sailed.”
“I can send these to the entire school with two emails,” Cassie warned.
Ryan sighed. “Cassie, you aren’t listening. As far as I’m concerned, there’s nothing I can do to KEEP you from doing that. This isn’t about me keeping my privacy anymore. That’s out of my control. This is now about whether I take this tape of you five to your parents–OUR parents, Liz–to the school board, or to the police.”
“Ryan! You can’t!” Liz said incredulously. “Mom and Dad would disown me!”
Annie was looking panicked. “The police? Over a little prank?”
“I’m pretty sure that you leave prank behind around blackmail,” Ryan snapped. “And don’t forget your coach, Annie–bet she’ll love the publicity for the lacrosse team.”
Now Cassie looked a lot more nervous. “What if we let YOU delete the pictures from our phones? Then you’d know you were in the clear.”
Ryan shook his head again. “How would I know you didn’t already save them to the cloud? Besides, it seems like a pretty uneven swap - you see me naked, and I just delete the pictures and move on.”
Still rubbing her sore butt, Sarah snarled, “What, you think WE should all get naked for YOU? Keep dreaming.”
Ryan looked Sarah up and down, then chuckled. “Frankly, I don’t think that seeing you naked would be much of a dream.” Sarah sputtered angrily, crossing her arms instinctively. While she had always had multiple boys vying for her attention, she had also long been highly self-conscious about her chest. Her breasts were A cup, and while they suited her skinny torso, she had endured plenty of itty-bitty-titty jokes through middle school.
Ryan turned his attention back to Cassie. “So - your call. Either you get yourself over here across my lap, or you start planning how you’re going to answer the reporters when they get a hold of this story.”
Cassie looked to her friends. Jessica’s usual grin was gone, replaced by a very serious expression. “He’s not joking, Cass. Besides, you said it yourself - he’s hot. You know that pics of his cock would be embarrassing, but how many girls would he suddenly have the attention of? You were all but drooling.”
“Jessica!”
“It’s true!” her friend continued. She looked at the other girls. “I don’t know about you guys, but as far as I’m concerned, he’s got all the high cards.” She looked to Ryan now. “OK. You win. You can fuck up our lives. So how do you propose we get out of this situation? I mean, the same thing you said applies to us, too - if there’s no way for us to know that you’ll get rid of those tapes, we might as well take our chances, right? So what do you have in mind?”
Ryan nodded. He hadn’t really figured Jessica would be the one to cut to the chase, but he liked her for being honest. “Like I said - I’m going to give each of you a spanking to start with, and then we’ll talk actual punishment.”
Now it was Jessica’s turn to shake her head. “Nope. Not good enough. We get all of the terms out on the table, right here and now, or we all take our chances.”
“Jessica, what are you DOING?” Liz hissed. “Don’t piss him off more!”
“I’m not going to piss him off more,” Jessica said calmly. “But I’m not going to be his slave for the rest of my life, either. We’re going to agree to terms, and then we’ll deal with it.” She turned back to Ryan. “I’m assuming that there’s no way we can get out of this with a simple spanking, right? It would mean you get to see everyone’s bare asses, plus there’s got to be some value in getting to lord it over five good looking girls.”
“Much as I plan to enjoy spanking each of you, that’s not going to be enough for me to give you the tapes. I suppose that sex with the four of you – NOT you, Liz, that’s just wrong – would be off the table as well?”
Annie looked like she was going to be sick. “You’re fucking right that’s off the table!” Cassie said angrily. “Not gonna happen!”
Ryan raised his hands in surrender. “I didn’t expect it would. So somewhere in between, then.”
“Somewhere between,” Jessica nodded. She took a deep breath. “Okay - how about you get your spankings, and then you get to see each of us naked?”
There was an eruption of noise as several of the girls began shouting objections at once.
“There’s no way!”
“I’m not getting naked in front of my STEPBROTHER!” Liz protested.
“I’m not either!” Annie agreed.
“SHUT UP!” Jessica yelled, and suddenly everyone was quiet.
The army brat looked around at the others. “You guys better get real about this QUICK. What part of ‘he can have us arrested’ are you not following? Look, I don’t like this any more than you do, and I think it’s pretty fucking clear that Ryan trapped us, but the bottom line is that WE FUCKED UP. We were the ones who came into his room, and we were the ones who tried to blackmail him.” She shook her head, smiling ruefully. “It’s always the boys who are being pulled around by their dicks, right, but we were just as stupid horny as they are this time. All it took was one good looking guy and the thought that we might get a look at him naked and we turned into idiots.”
She turned back to Ryan. “Like I said - spankings for each of us, plus you get a look at us naked. Deal?”
“No, no deal,” Ryan answered. “You make a pretty good case for me, Jessica. You’d count yourself lucky if I took that offer, wouldn’t you? No, here’s how this is going to work, and you can take it or leave it. No one is going to be here but us until around noon tomorrow, which gives me a whole night and morning to enjoy. I’m willing to agree that actual sex is off the table. I’m not even going to demand total control over you.”
“Then what?” Jessica asked.
“Then we’re going to play a few games. I’ll set the games and the rules. Each game will have one loser, and that loser will have to perform a punishment I set. The winner will also get a prize - she will get to pick one other girl to join the loser in taking the punishment for that game. We play five games, and after that, we’re even. I’ll delete my videos, and you delete yours.”
“Wait,” Annie asked hopefully. “Doesn’t that mean that if we win all the games, we could get out without any extra punishment beyond the spanking?”
“That’s possible, yes,” Ryan answered with a smile. “You could get that lucky.”
The tall girl pulled on her ponytail. “And you promise that you’ll delete the tape?”
“That’s the deal,” he replied.
“But how do we know we can trust YOU?” Sarah asked angrily. “You set all this up!”
“We don’t know,” Jessica answered.
Liz looked at Ryan. “Ryan - I know that this was totally wrong of me to let happen. I get that. I’m even….I guess….willing to accept that we deserve some sort of punishment for that. I want your word, though, that those tapes go away if we agree to this. I know you aren’t a liar. If you say you’ll do this, you will. So, do we have your word?”
“You do,” Ryan said. “And nothing about what happens here will ever be talked about by me.”
Liz looked at the other girls. “He really doesn’t lie,” she said. “If he says it, he means it.”
“This is as good a deal as we’re going to get,” Jessica agreed. “We should take it.”
“No!” Sarah retorted. “I am NOT letting him do ANYTHING to me.”
“You are,” said Jessica firmly. “If everyone else is on board, you’re in too. All of us or none. If you try to bail on us, Sarah, we’re done with you. You take your lumps with the rest of us, or you can explain to the rest of the school when we tell them you ditched on your friends.”
No one else objected. Sarah growled, then said, reluctantly, “Fine. Whatever.”
“OK, you have your deal,” Jessica said, sighing.
“Cassie,” Ryan said, turning back to the girl, who was now wearing a look of resignation. “I think we were about to take care of some business here?”
The petite brunette shuffled over reluctantly to his side, and Ryan patted his lap. Cassie lowered herself over, carefully avoiding letting her breasts brush his legs, but then she gave a sudden yelp of surprise as she felt something poke her in the groin. “What’s the matter?” Ryan asked innocently.
“Your…your dick!” Cassie blushed furiously. “It’s poking me…You know what’s wrong!”
“A few minutes ago you were ready to blackmail me with pictures of my dick, and now you’re upset that it’s hard? Would you rather have it poking you this way, or would you prefer I poke you somewhere else, Cassie? I could be flexible about this. But to be honest,” he said, “I’d just as soon stick with this spanking for the moment.” Ryan rubbed the girl’s tight little bottom, watching her squirm under his touch. “I don’t think many people realize what an amazing ass you have, Cassie. I do, though. You sat in front of me in Spanish last year, remember? I loved football Fridays, because that meant you were in that spandex color guard gear, and I could stare all period long. You never noticed, did you?”
Cassie’s brain was whirling. On the one hand, there was Ryan’s hand, which was currently rubbing her bottom as if that was perfectly normal, letting his fingers slip into the shallow space left between her cheeks, which she had clenched as tightly as she could. On the other hand, RYAN’S hand was on her butt, and it felt so NICE the way he was rubbing, and he said he had been staring ALL SEMESTER at HER. No one stared at her. And now his fingers… “HEY!” she squealed as Ryan’s hand slid under her shorts and over her cotton panties. Cassie tried to roll off, but he easily pinned her in place with one leg across her own and his other hand holding her shoulder firmly. She struggled, but even as she did, she felt warmth spreading from between her legs. Everywhere his fingers slid, little lines of heat sparked across her bottom, and she gasped as they brushed just close enough to the juncture of her thighs to send a tingle through her body.
Before she could do anything, however, Cassie felt herself tip forward, and was barely able to get her hands out to catch herself and keep from hitting her head. Her butt was now right on the edge of Ryan’s lap, and her thighs flat and vulnerable. It was the PERFECT position if you wanted to maximize the impact and embarrassment of a spanking, at least as soon as…
Cassie moaned as she felt her shorts come down. Now only her black and white striped panties were protecting her modesty, and she was acutely aware that at this angle, Ryan would have NO problem seeing everything. “Oh, god - Ryan, please let me keep my panties! Please!”
“Um….no.” Ryan’s words were followed by a quick tug, and Cassie could only whimper as her secrets were completely revealed to him. “But don’t worry - I’ll give you a distraction so you don’t have to think about how you’re on display for me.”
Before Cassie could utter a word, the echoes of a firm-handed spanking once again filled the room. Cassie wept and clutched at Ryan’s leg, but nothing slowed the assault on her tiny derriere. The warmth that had been between her legs was now replaced by a fire across the surface of her butt and thighs that was intensifying by the second. Cassie grit her teeth, willing herself not to give in to the pain, but it was only a short minute or two before the girl began weeping openly and pleading for mercy.
SMACK! SMACK! SMACK!
The taut flesh of Cassie’s bottom was now burning, and each repeated slap to her wobbling cheeks added fuel to the bonfire. Then suddenly the spanks stopped coming, and there was just Ryan’s hand rubbing her gently, back and forth, massaging the sting from her backside. She gulped down a sob and tried to breathe, ignoring the fact that a boy was currently feeling up her ass and focusing on the pleasure of the touch against her skin.
CRACK!
The unexpected sound made Cassie’s head pop up for just a second, looking around for the source of the noise. Then her bottom registered that the noise had been the impact of a hairbrush against her left cheek, and a howl of agony made the other girls in the room wince. A second CRACK! against the right globe of her tiny tush drew the same response, and from there it was simply a question of how much noise Cassie could produce before her voice gave out entirely. Each successive blow of the wooden implement seemed to increase both the volume and the pitch of her cries. Cassie tried to beg for Ryan to stop, but she couldn’t catch enough of a breath to speak. She bawled like she hadn’t bawled in years, not since the last time her own father had lit her backside on fire when he caught her messing around with his power tools.
After what seemed to Cassie to be a month, the rain of pain finally stopped. Cassie blubbered on, unable to even try to lever herself up from across Ryan’s lap. He rubbed her back and waited for her to get control of herself, and Liz eventually brought her a washcloth, which Cassie gratefully used to wipe down her tear-lined face. She gingerly pulled up her panties, wincing as the cloth brushed against the painfully inflamed skin, and opted to leave her shorts off rather than add any more pressure back there. She looked at Ryan, meek and chastised. “I’m sorry. Really sorry. I was wrong, and I…I deserved the spanking.”
Ryan nodded approvingly. He looked at the three remaining girls, then pointed to Jessica. “You took charge, so I guess you’re up next.”
Jessica nodded, trying to maintain her composure, and stepped forward. “Ok. I’m ready.” This part is going to be the easy part, she thought to herself. The pain you know isn’t what gets you. She wondered if the second half of the night would be as straightforward as this.
She doubted it.
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Fred Key
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Re: A Small Price To Pay (Ch. 3 6/20))
Chapter 4 - Strength can be a Weakness
Jessica had grown up as an Army brat, and had moved many times over the years. She had no problems making friends with her winning smile and upbeat nature, and since she wasn’t the sort of girl who was interested in makeup and attracting attention, the cliques in high school generally left her alone - she just wasn’t enough of a threat to their position to be on their radar. It probably also helped that she clearly wasn’t easy prey.
Years of running and fitness classes had given her a well-toned body and a sense of self-confidence that projected easily. Most of the time, when Jessica stepped in and spoke up, people quieted down. She also could hold her own in a fight if she needed to, as one would-be bully at the high school could attest. Jessica had seen her grab a younger girl by the arm and sling her into a locker; before the first girl could take another step, Jessica had her on the ground with her arm twisted awkwardly. She had made the bully apologize before letting her up, then had walked off to class like nothing had happened.
Corporal punishment was nothing new for Jessica either. Her mother, now a Captain, was the career officer in the family, and she had been a firm believer in establishing discipline both through grounding and through the application of a wooden spoon to Jessica’s backside as needed.
She swept her sandy blond hair back out of her eyes and looked at Ryan. He was a good looking, reasonably fit guy who also happened to be naked at the moment. Jessica was irritated with herself that she kept checking out his cock, but to be fair, it was the first one she’d seen in person, and in her opinion, it was a very nice one. Even in a semi-flaccid state, she couldn’t help but wonder how that thing would fit into her, especially since two fingers seemed like the most she could comfortably insert into herself when she masturbated.
Stop thinking about that! She scolded herself for losing focus. You need to focus on not showing any fear. Show him you aren’t going to give in to him, even if you have to do what he says. He’s fit, but he’s not your mom, and any spanking he gives you, even with the brush, isn’t going to be close to what your mom can dish out.
“Over your lap?” she asked Ryan calmly.
Ryan tilted his head a little, checking her out. She straightened up, drawing her shoulders back to emphasize her curves a little while presenting an expressionless face. Can’t hurt anything, she thought.
“Are you in a hurry?” the boy asked her. “I wouldn’t think you’d be so eager to get your butt roasted. Or maybe you ARE eager?”
Jessica rolled her eyes. “Oh, yeah. That’s it. I love to be spanked. You caught me. Please, spank me until I cum. Spank me, baby. Yeah. Oooh. Oh. So sexy.”
Ryan laughed. “You are funny. No wonder people like you so much.”
“I try,” Jessica replied. “Let’s just do this, ok? You want to redden my ass, fine, but the sooner we’re done with all this the better.”
“So you’re fine with me reddening your ass?”
“I’m not scared, if that’s what you mean. You really aren’t particularly intimidating, you know,” the girl answered.
“Huh. Well, then, how about we make this a little more interesting? You’re not intimidated, and I like a good challenge. I can already spank you as long and hard as I like, so I’ll give you a break - I’ll only give you 25 swats total. However, if you move your hands or break position at any point while I’m giving them, you have to take off a piece of clothing. I’m assuming you are wearing a bra and undies under there, right? Not sure what girl etiquette is at a sleepover. Anyway, if you can get through the 25 without moving, I’ll call you done. Otherwise, we could have a nice long session of lap time if you prefer, and I KNOW that I can make you cry with this hairbrush if I use it long enough.”
Jessica considered this for a moment. On the one hand, she had no interest in stripping for Ryan, but she was pretty certain that she would end up doing that regardless of her choices here and now. If she took his deal, maybe it would happen a little sooner, but if it was going to happen anyway, and it got her out of what Cassie had just endured….
“Deal - on one condition. You can’t use the hairbrush for your 25 swats. No paddle or belt, either.”
“Done,” Ryan answered quickly. Before she could say anything more, he stood up and pulled on a pair of running shorts lying on the floor. He then turned and guided Jessica over to his desk chair. “Hands on the top of the chair. Stick out your backside, please. Remember, if you break position, it’s a piece of clothing. But obviously, this doesn’t count.” He carefully lowered her shorts to just below her butt, leaving a pair of pale lavender underpants as her only protection. With a gentle but insistent pair of fingers, he pulled each side of her underwear upward into the crack between her legs, largely exposing her backside. Stretched taut by the angle she was bent at, she knew there would be precious little between her and the painful spanks she was about to endure.
The first “pop” hardly even registered for Jessica. It was only when Ryan said, “Since the bet is for 25 swats, I think you should count them out loud,” that she realized he had given her the first spank. She couldn’t help but grin. If that was the best he could do, this was going to be a breeze. “One,” she said firmly.
The second swat landed on her other cheek, again barely enough to get her to notice. “Two,” she said, wondering what Ryan was up to.
“Three!”
“Four!”
“Five!”
Three quick spanks, again with little result. She was already a fifth of the way there, and he hadn’t even gotten a wince out of her.
“I can see I’m not really having much of an impact, am I,” Ryan said cheerfully. “I’ll try a bit harder for you.”
“Don’t bother on my account,” Jessica muttered.
This time the “pop” against her rear stung a bit. Ryan’s hand arced down before she had even gotten the word “six” out, and another stinger struck her right cheek. A bit more bite, but nothing that would make her break position. “Seven,” she counted.
Whap! Whap! Whap! The eighth, ninth, and tenth swats were still harder, this time enough to draw a wince from Jessica. Her butt was beginning to feel the cumulative effect of the spanks.
WHAP! “OW! Eleven!” This one was MUCH harder than before. It felt like Ryan had wound up before delivering the smack, and it caught her right on her left sit-spot.
WHAP! “Twelve!” Another hard swat, again to that same place where her thigh met her bottom. Jessica fought the urge to move her hands and rub that tender place.
WHAAPPP! “AAHH! Thirteen!” Right in the same spot. Jessica let out a strangled cry of pain as the burning became an inferno. That’s when she understood what Ryan had done. He hadn’t misjudged her strength.
He had counted on it. He had used it to goad her into taking the bet.
Jessica didn’t even hear the fourteenth slap. It struck in the EXACT same place, just below her left bottom cheek, and she was up and on her feet before she realized it, wailing in pain. She almost tripped on her shorts and panties, which had long since puddled at her feet, and she couldn’t care less that her neatly trimmed pubic region was now on full display.
Ryan graciously waited until she had calmed a bit before he held out his hand. After a moment, Jessica realized what he was waiting for. Trying to recover some of her lost dignity, she pulled her sleep shirt off, revealing the tank top she was wearing underneath. It wasn’t as if she was showing anything in doing so - the tank had a shelf bra and was perfectly decent - but even so, Jessica felt a twinge as she handed him her top. A tiny sense that this was only the first of more humiliations to come, and a fear that grew from that sense.
Grudgingly, Jessica resumed her position. Only seven more to go, she thought. I can hold on. I can do this. She gritted her teeth and squeezed her eyes closed tightly.
WHAP! “Oh, FUCK! FUCK! SIX-FUCKING-TEEN-FUCK-FUCK FUCK!” Did he have a laser sight on that hand of his? The same spot again, and Jessica knew her bottom must be an ugly red there now.
WHAP!! “AHHHAHHAHAA!” The tears burst from her eyes as her bottom flamed once again into agony. She couldn’t take it. Not another swat there! Her hand flew back to cover the tender curve.
“That’s breaking position,” Ryan said. “I was starting to think you were going to win this bet, Jessica, but you still have another eight spanks coming, and I believe you owe me your shorts. Since you already kicked them off, we’ll just count that as a loss and move on, yes?”
“Please, Ryan - please pick somewhere else to spank! You can’t keep smacking that one place - it hurts too much!” Jessica’s tear-streaked face was clearly showing her pain - both the pain from her seat and the pain of admitting her own weakness.
“That wasn’t the deal, Jessica. The deal was 25 spanks, no belt or hairbrush or whatever. I thought it was pretty generous, really.”
Jessica flushed bright red. She was already bottomless, with one foot still in her lavender underpants. She stepped clear of them. “Look, we know where this is going, right?” she said, and before Ryan could reply, she pulled her tank top off. I can’t believe I’m doing this, standing here naked in front of Liz’s brother. I can’t believe I’m standing here NAKED! My ass is on fire, and my boobs are out, and everyone can see everything. Somehow, the blonde girl managed to blush even more at this realization. She had one arm over her breasts, but the other was still trying to massage the pain out of her left cheek, and she could see Ryan staring directly at her uncovered crotch, and she knew he could see the faint hint of her lower lips, and she forced herself to look him in the eye, and said “There. I’m naked. Just PLEASE put the last spanks somewhere else. PLEASE.”
The other girls were silent, staring at their friend. Each one had the same thing running through her head. Am I next?
“But Jessica,” Ryan said. “I still owe you eight good ones, and if you don’t want them all on that poor, abused cheek, it’s going to cost you.”
“You already have me naked, asshole,” Jessica growled. “What else is there?”
Ryan paused to look at the girl. Her breasts, covered though they were, were still showing a hint of pale pink nipple, and he very much wanted to see more. “Hands to your sides. I want to see you fully naked.”
Jessica hesitated. “You already can see everything!”
“I want to see you on MY terms. No covering. And while you’re at it, spread your legs a bit wider, too. I want to be able to see everything. You stand there for me for the next five minutes, and I’ll let you off the last eight swats.”
The teen squirmed. She knew what spreading her legs would make visible, and she knew that Ryan wouldn’t be shy about looking her over from head to toe. Jessica had never let a boy do more than slip a hand under her shirt for a quick feel during a make-out session, and now here she was, more on display than she could have possibly imagined. She desperately wanted to grab her clothing and run, but she knew she had no options.
Her hands fell to her sides, and she shuffled her feet apart a little more. Her breasts, which were high and perky, were now there for him to see. She felt his eyes on her, taking in the handfuls, the quarter-sized areolas, and her nipples, which were suddenly stiffening. The awareness only added to the humiliation of the moment. What the fuck? She thought to herself. I’m naked in front of Liz’s brother! I am NOT turned on. It must just be the chill. Even as she told herself that, however, she felt a tingle from below that she couldn’t ignore. THAT wasn’t the air, she thought. What the hell is wrong with me?
If she had asked that out loud, Ryan would have said, “Absolutely nothing.” He was feasting his eyes on Jessica’s fit and tanned body, taking in those tempting pink nipples atop those swelling breasts. As he knelt in front of her to take a close look at her pussy, printing into his mind her most private of places, she was sure he could hear the crashing beat of her heart and the moan of shame that was inside her. God help her, she WANTED him to touch her right now, to touch her and make that shiver grow to a full-blown, body-shaking orgasm. She wanted to push her hips forward just a little, just enough to brush his face, enough to get him to bury his tongue deep in her…
Ryan was so close she could feel his breath on her lower lips. She moaned in shame at the thought of how utterly exposed she was, and how her own decisions had placed her here in this moment.
The boy looked up at the teen, her eyes tightly closed, and smiled. Better than I could have possibly hoped for, he thought to himself. He stood and delivered a sharp smack across Jessica’s bare ass that made her eyes pop open in surprise.
“You can get dressed again,” he said. “I’ll come back to you in a bit. Right now, though, there are still two of your friends who are waiting their turn, and I don’t want to disappoint them. Liz, I hope you’ll forgive me, but I think I’m going to save you for last here, so I guess that means it’s your turn, Annie…”
The tall redhead moaned a sad “noooooooo!” as Ryan took her hand and pulled her to the center of the room for her turn as the center of his attention.
Jessica had grown up as an Army brat, and had moved many times over the years. She had no problems making friends with her winning smile and upbeat nature, and since she wasn’t the sort of girl who was interested in makeup and attracting attention, the cliques in high school generally left her alone - she just wasn’t enough of a threat to their position to be on their radar. It probably also helped that she clearly wasn’t easy prey.
Years of running and fitness classes had given her a well-toned body and a sense of self-confidence that projected easily. Most of the time, when Jessica stepped in and spoke up, people quieted down. She also could hold her own in a fight if she needed to, as one would-be bully at the high school could attest. Jessica had seen her grab a younger girl by the arm and sling her into a locker; before the first girl could take another step, Jessica had her on the ground with her arm twisted awkwardly. She had made the bully apologize before letting her up, then had walked off to class like nothing had happened.
Corporal punishment was nothing new for Jessica either. Her mother, now a Captain, was the career officer in the family, and she had been a firm believer in establishing discipline both through grounding and through the application of a wooden spoon to Jessica’s backside as needed.
She swept her sandy blond hair back out of her eyes and looked at Ryan. He was a good looking, reasonably fit guy who also happened to be naked at the moment. Jessica was irritated with herself that she kept checking out his cock, but to be fair, it was the first one she’d seen in person, and in her opinion, it was a very nice one. Even in a semi-flaccid state, she couldn’t help but wonder how that thing would fit into her, especially since two fingers seemed like the most she could comfortably insert into herself when she masturbated.
Stop thinking about that! She scolded herself for losing focus. You need to focus on not showing any fear. Show him you aren’t going to give in to him, even if you have to do what he says. He’s fit, but he’s not your mom, and any spanking he gives you, even with the brush, isn’t going to be close to what your mom can dish out.
“Over your lap?” she asked Ryan calmly.
Ryan tilted his head a little, checking her out. She straightened up, drawing her shoulders back to emphasize her curves a little while presenting an expressionless face. Can’t hurt anything, she thought.
“Are you in a hurry?” the boy asked her. “I wouldn’t think you’d be so eager to get your butt roasted. Or maybe you ARE eager?”
Jessica rolled her eyes. “Oh, yeah. That’s it. I love to be spanked. You caught me. Please, spank me until I cum. Spank me, baby. Yeah. Oooh. Oh. So sexy.”
Ryan laughed. “You are funny. No wonder people like you so much.”
“I try,” Jessica replied. “Let’s just do this, ok? You want to redden my ass, fine, but the sooner we’re done with all this the better.”
“So you’re fine with me reddening your ass?”
“I’m not scared, if that’s what you mean. You really aren’t particularly intimidating, you know,” the girl answered.
“Huh. Well, then, how about we make this a little more interesting? You’re not intimidated, and I like a good challenge. I can already spank you as long and hard as I like, so I’ll give you a break - I’ll only give you 25 swats total. However, if you move your hands or break position at any point while I’m giving them, you have to take off a piece of clothing. I’m assuming you are wearing a bra and undies under there, right? Not sure what girl etiquette is at a sleepover. Anyway, if you can get through the 25 without moving, I’ll call you done. Otherwise, we could have a nice long session of lap time if you prefer, and I KNOW that I can make you cry with this hairbrush if I use it long enough.”
Jessica considered this for a moment. On the one hand, she had no interest in stripping for Ryan, but she was pretty certain that she would end up doing that regardless of her choices here and now. If she took his deal, maybe it would happen a little sooner, but if it was going to happen anyway, and it got her out of what Cassie had just endured….
“Deal - on one condition. You can’t use the hairbrush for your 25 swats. No paddle or belt, either.”
“Done,” Ryan answered quickly. Before she could say anything more, he stood up and pulled on a pair of running shorts lying on the floor. He then turned and guided Jessica over to his desk chair. “Hands on the top of the chair. Stick out your backside, please. Remember, if you break position, it’s a piece of clothing. But obviously, this doesn’t count.” He carefully lowered her shorts to just below her butt, leaving a pair of pale lavender underpants as her only protection. With a gentle but insistent pair of fingers, he pulled each side of her underwear upward into the crack between her legs, largely exposing her backside. Stretched taut by the angle she was bent at, she knew there would be precious little between her and the painful spanks she was about to endure.
The first “pop” hardly even registered for Jessica. It was only when Ryan said, “Since the bet is for 25 swats, I think you should count them out loud,” that she realized he had given her the first spank. She couldn’t help but grin. If that was the best he could do, this was going to be a breeze. “One,” she said firmly.
The second swat landed on her other cheek, again barely enough to get her to notice. “Two,” she said, wondering what Ryan was up to.
“Three!”
“Four!”
“Five!”
Three quick spanks, again with little result. She was already a fifth of the way there, and he hadn’t even gotten a wince out of her.
“I can see I’m not really having much of an impact, am I,” Ryan said cheerfully. “I’ll try a bit harder for you.”
“Don’t bother on my account,” Jessica muttered.
This time the “pop” against her rear stung a bit. Ryan’s hand arced down before she had even gotten the word “six” out, and another stinger struck her right cheek. A bit more bite, but nothing that would make her break position. “Seven,” she counted.
Whap! Whap! Whap! The eighth, ninth, and tenth swats were still harder, this time enough to draw a wince from Jessica. Her butt was beginning to feel the cumulative effect of the spanks.
WHAP! “OW! Eleven!” This one was MUCH harder than before. It felt like Ryan had wound up before delivering the smack, and it caught her right on her left sit-spot.
WHAP! “Twelve!” Another hard swat, again to that same place where her thigh met her bottom. Jessica fought the urge to move her hands and rub that tender place.
WHAAPPP! “AAHH! Thirteen!” Right in the same spot. Jessica let out a strangled cry of pain as the burning became an inferno. That’s when she understood what Ryan had done. He hadn’t misjudged her strength.
He had counted on it. He had used it to goad her into taking the bet.
Jessica didn’t even hear the fourteenth slap. It struck in the EXACT same place, just below her left bottom cheek, and she was up and on her feet before she realized it, wailing in pain. She almost tripped on her shorts and panties, which had long since puddled at her feet, and she couldn’t care less that her neatly trimmed pubic region was now on full display.
Ryan graciously waited until she had calmed a bit before he held out his hand. After a moment, Jessica realized what he was waiting for. Trying to recover some of her lost dignity, she pulled her sleep shirt off, revealing the tank top she was wearing underneath. It wasn’t as if she was showing anything in doing so - the tank had a shelf bra and was perfectly decent - but even so, Jessica felt a twinge as she handed him her top. A tiny sense that this was only the first of more humiliations to come, and a fear that grew from that sense.
Grudgingly, Jessica resumed her position. Only seven more to go, she thought. I can hold on. I can do this. She gritted her teeth and squeezed her eyes closed tightly.
WHAP! “Oh, FUCK! FUCK! SIX-FUCKING-TEEN-FUCK-FUCK FUCK!” Did he have a laser sight on that hand of his? The same spot again, and Jessica knew her bottom must be an ugly red there now.
WHAP!! “AHHHAHHAHAA!” The tears burst from her eyes as her bottom flamed once again into agony. She couldn’t take it. Not another swat there! Her hand flew back to cover the tender curve.
“That’s breaking position,” Ryan said. “I was starting to think you were going to win this bet, Jessica, but you still have another eight spanks coming, and I believe you owe me your shorts. Since you already kicked them off, we’ll just count that as a loss and move on, yes?”
“Please, Ryan - please pick somewhere else to spank! You can’t keep smacking that one place - it hurts too much!” Jessica’s tear-streaked face was clearly showing her pain - both the pain from her seat and the pain of admitting her own weakness.
“That wasn’t the deal, Jessica. The deal was 25 spanks, no belt or hairbrush or whatever. I thought it was pretty generous, really.”
Jessica flushed bright red. She was already bottomless, with one foot still in her lavender underpants. She stepped clear of them. “Look, we know where this is going, right?” she said, and before Ryan could reply, she pulled her tank top off. I can’t believe I’m doing this, standing here naked in front of Liz’s brother. I can’t believe I’m standing here NAKED! My ass is on fire, and my boobs are out, and everyone can see everything. Somehow, the blonde girl managed to blush even more at this realization. She had one arm over her breasts, but the other was still trying to massage the pain out of her left cheek, and she could see Ryan staring directly at her uncovered crotch, and she knew he could see the faint hint of her lower lips, and she forced herself to look him in the eye, and said “There. I’m naked. Just PLEASE put the last spanks somewhere else. PLEASE.”
The other girls were silent, staring at their friend. Each one had the same thing running through her head. Am I next?
“But Jessica,” Ryan said. “I still owe you eight good ones, and if you don’t want them all on that poor, abused cheek, it’s going to cost you.”
“You already have me naked, asshole,” Jessica growled. “What else is there?”
Ryan paused to look at the girl. Her breasts, covered though they were, were still showing a hint of pale pink nipple, and he very much wanted to see more. “Hands to your sides. I want to see you fully naked.”
Jessica hesitated. “You already can see everything!”
“I want to see you on MY terms. No covering. And while you’re at it, spread your legs a bit wider, too. I want to be able to see everything. You stand there for me for the next five minutes, and I’ll let you off the last eight swats.”
The teen squirmed. She knew what spreading her legs would make visible, and she knew that Ryan wouldn’t be shy about looking her over from head to toe. Jessica had never let a boy do more than slip a hand under her shirt for a quick feel during a make-out session, and now here she was, more on display than she could have possibly imagined. She desperately wanted to grab her clothing and run, but she knew she had no options.
Her hands fell to her sides, and she shuffled her feet apart a little more. Her breasts, which were high and perky, were now there for him to see. She felt his eyes on her, taking in the handfuls, the quarter-sized areolas, and her nipples, which were suddenly stiffening. The awareness only added to the humiliation of the moment. What the fuck? She thought to herself. I’m naked in front of Liz’s brother! I am NOT turned on. It must just be the chill. Even as she told herself that, however, she felt a tingle from below that she couldn’t ignore. THAT wasn’t the air, she thought. What the hell is wrong with me?
If she had asked that out loud, Ryan would have said, “Absolutely nothing.” He was feasting his eyes on Jessica’s fit and tanned body, taking in those tempting pink nipples atop those swelling breasts. As he knelt in front of her to take a close look at her pussy, printing into his mind her most private of places, she was sure he could hear the crashing beat of her heart and the moan of shame that was inside her. God help her, she WANTED him to touch her right now, to touch her and make that shiver grow to a full-blown, body-shaking orgasm. She wanted to push her hips forward just a little, just enough to brush his face, enough to get him to bury his tongue deep in her…
Ryan was so close she could feel his breath on her lower lips. She moaned in shame at the thought of how utterly exposed she was, and how her own decisions had placed her here in this moment.
The boy looked up at the teen, her eyes tightly closed, and smiled. Better than I could have possibly hoped for, he thought to himself. He stood and delivered a sharp smack across Jessica’s bare ass that made her eyes pop open in surprise.
“You can get dressed again,” he said. “I’ll come back to you in a bit. Right now, though, there are still two of your friends who are waiting their turn, and I don’t want to disappoint them. Liz, I hope you’ll forgive me, but I think I’m going to save you for last here, so I guess that means it’s your turn, Annie…”
The tall redhead moaned a sad “noooooooo!” as Ryan took her hand and pulled her to the center of the room for her turn as the center of his attention.
-
Fred Key
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Re: A Small Price To Pay (Ch. 3 6/20))
OK, short pause here. It's taking a bit longer for me to get through this opening round of punishments before we get to some ENF gamey fun, and I am a bit worried that this is too drawn out even for one of my stories. On the plus side, I've been able to write more over the past few weeks, which is making it possible for me to update with remarkable speed (for me, at least) on totally new material--"The Tutor" was a revision, so I was able to keep it flowing at a very fast clip onto the board while still teasing it out a bit. There's no guarantee that I can maintain that sort of pace, but I don't think the majority of people on here are going to lose it when an author takes as much as a week to post an update (I know we have stories that hang for months, too, but mars, if you keep me waiting that long for the continuation of Boyd vs. Girls, I'll never forgive you. 
) Anyhow, I guess I'm going to continue as things come to me, and we only have two more girls (Annie and Liz) before we get through the first phase, so if you are not happy with the level of ENF just yet, please hang in there. I have plans. 
For those of you who are reading and feel like answering, are you OK with the pacing here so far, or would you like to see it pick up a bit? I'm always open to feedback/suggestions. Frankly, with some of the truly outstanding writers who are on this site and have been around for some time, the bar for excellence is pretty high, which makes writing for this group a lot more of a challenge -- and a lot more interesting, too.
) Anyhow, I guess I'm going to continue as things come to me, and we only have two more girls (Annie and Liz) before we get through the first phase, so if you are not happy with the level of ENF just yet, please hang in there. I have plans. For those of you who are reading and feel like answering, are you OK with the pacing here so far, or would you like to see it pick up a bit? I'm always open to feedback/suggestions. Frankly, with some of the truly outstanding writers who are on this site and have been around for some time, the bar for excellence is pretty high, which makes writing for this group a lot more of a challenge -- and a lot more interesting, too.
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Darky
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Re: A Small Price To Pay (Ch. 3 6/20))
If waiting a bit means more fantastic chapters (like the last one or even better) I’ll be happy to wait. Although I think you are not losing pace and strong content at all, so keep it going. But I also have to admit, I hate waiting in a good story. Sometimes it is needed, so I’ll waitFred Key wrote: ↑Wed Jun 21, 2023 9:42 pm OK, short pause here. It's taking a bit longer for me to get through this opening round of punishments before we get to some ENF gamey fun, and I am a bit worried that this is too drawn out even for one of my stories. On the plus side, I've been able to write more over the past few weeks, which is making it possible for me to update with remarkable speed (for me, at least) on totally new material--"The Tutor" was a revision, so I was able to keep it flowing at a very fast clip onto the board while still teasing it out a bit. There's no guarantee that I can maintain that sort of pace, but I don't think the majority of people on here are going to lose it when an author takes as much as a week to post an update (I know we have stories that hang for months, too, but mars, if you keep me waiting that long for the continuation of Boyd vs. Girls, I'll never forgive you.
For those of you who are reading and feel like answering, are you OK with the pacing here so far, or would you like to see it pick up a bit? I'm always open to feedback/suggestions. Frankly, with some of the truly outstanding writers who are on this site and have been around for some time, the bar for excellence is pretty high, which makes writing for this group a lot more of a challenge -- and a lot more interesting, too.
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jimmythehand
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Re: A Small Price To Pay (Ch. 3 6/20))
The pace is good. The story is clearly building and I for one am enjoying each brick.Fred Key wrote: ↑Wed Jun 21, 2023 9:42 pm For those of you who are reading and feel like answering, are you OK with the pacing here so far, or would you like to see it pick up a bit? I'm always open to feedback/suggestions. Frankly, with some of the truly outstanding writers who are on this site and have been around for some time, the bar for excellence is pretty high, which makes writing for this group a lot more of a challenge -- and a lot more interesting, too.
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Drax6119
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Re: A Small Price To Pay (Ch. 3 6/20))
I am a particular fan of the "slow-burn buildup", ESPECIALLY when the writing is quality, like it is here.Fred Key wrote: ↑Wed Jun 21, 2023 9:42 pm OK, short pause here. It's taking a bit longer for me to get through this opening round of punishments before we get to some ENF gamey fun, and I am a bit worried that this is too drawn out even for one of my stories. On the plus side, I've been able to write more over the past few weeks, which is making it possible for me to update with remarkable speed (for me, at least) on totally new material--"The Tutor" was a revision, so I was able to keep it flowing at a very fast clip onto the board while still teasing it out a bit. There's no guarantee that I can maintain that sort of pace, but I don't think the majority of people on here are going to lose it when an author takes as much as a week to post an update (I know we have stories that hang for months, too, but mars, if you keep me waiting that long for the continuation of Boyd vs. Girls, I'll never forgive you.
For those of you who are reading and feel like answering, are you OK with the pacing here so far, or would you like to see it pick up a bit? I'm always open to feedback/suggestions. Frankly, with some of the truly outstanding writers who are on this site and have been around for some time, the bar for excellence is pretty high, which makes writing for this group a lot more of a challenge -- and a lot more interesting, too.
You just keep doing what you're doing.
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