Dare Me (new 5/23)

[neverdoubted]

Dare Me - Chapter 17 - Little Sister, Big Sister (Part 4)

I could practically hear the trap snap shut on the poor, defenseless prey. I sat my pencil down and looked at her like...well, like a hunter spying a poor, defenseless prey. I saw relief on her face mixed with excitement and a little fear. Part of her was already regretting her words. But it was too late to back out now!

"Ok, fine," I said, "but first, I want you to explain why there's a naked picture of me hanging in the cheer team's locker room."

BUSTED! Her face went white, and she started blubbering excuses mixed with apologies. It was the other girls, you see, the older ones, who insisted on keeping it up. She might have won the team spirit vote at camp, but now that school had started, she was back to just being a scrub. She had no influence!

"That's a shame," I growled with a menacing grin, "because you're gonna need all the influence you can spare to complete your dare."

When I ordered her to retrieve her health textbook and bring it to me, she gave me a confused look, but left without a word. Now that her dare had officially begun, she had conditioned herself to be ready to adapt to any request, no matter how unusual or absurd. I used her absence to adjust the growing bulge in my boxers. You could say my libido had been conditioned to react to those words as well, but in a different way.

She returned shortly and placed the health textbook on my desk. I thumbed through the pages until I got to the one I had been searching for. Eureka!

"All I wanted this year was a fair chance to get a girlfriend and possibly score. But your little poster stunt has ruined my reputation with every cheerleader in our school and most of the other girls too," I explained, "so you're going to make it up to me."

I turned the book around so she could read it. Page 69 (he he, nice!) contained a box explaining the four distinct types of physical interactions experts generally grouped under the umbrella of a "sex act". It went on to briefly describe each type. The first was manual, like a hand job. It's kind of a long story, but you could say I had already come very close to experiencing one of those. The second was oral - a blowjob, if you will. The third was traditional vaginal sex. They pointed out that this was the kind that makes babies if you aren't careful. And the fourth was anal.

Pointing to the box, I laid out my objective, "you're going to help me restore my reputation by getting one of the cheerleaders to have sex with me."

She looked up at me with her mouth hanging open, scandalized by the indecent proposal, but also more than a little confused. This didn't sound like any dare I had given her in the past. But I was getting to that part. I continued, "it doesn't matter which girl or what kind of sex. I just figure this will be the quickest way to put an end to the rumors about me."

I wasn't lying about not caring which girl. Sure, I had formally ranked every single cheerleader according to her hotness and sex appeal. But honestly, there wasn't that much gap between the top and the bottom of that incredible list. I would be thrilled to lose my virginity with any of them.

Lucy opened her mouth to ask the obvious question: what did any of this have to do with her dare? But before she could speak, I cut her off with a solemn voice. "Lucy Jenkins, I dare you-"

Immediately, her eyes started fluttering. This was going to be fun!

The terms of her dare, while unorthodox, couldn't have been clearer. Deliver me a cheerleader willing to perform one of the sex acts from her health textbook. But the consequences of failure are what made the whole thing so devious. For every day she failed her assignment, she would have to expose herself to another person at school.

Unfortunately for her, even if she had a candidate in mind, the late hour made executing and completing the assignment tonight next to impossible. That meant she had to perform her first punishment task the very next day. And thanks to my advanced scouting, I had already lined one up.

It was late in the school day, Tuesday afternoon. Lucy's final period was cheer practice which she and the other cheerleaders got to count as their P.E. credit. She walked anxiously past the open door to the wood shop classroom, peering intently to make sure it was empty of students before doubling back to stand in the hallway just out of sight and gather her nerves.

The only occupant was the grizzled teacher, Mr. Frenzel. He didn't have a class for seventh period because he needed time to clean up his shop at the end of each day and put all the tools away.

I had generously given Lucy a choice between getting naked in front of a student or a teacher. Not much of a choice, really. I knew before I asked which one she would choose. As embarrassing as it may be showing your naked body off to one of the teaching staff, she would pick it any day over a student. At least the teacher wasn't likely to go blabbing about the humiliating exhibition to the whole school!

That's not to say there wasn't some risk involved. I can say from personal experience that, no matter what the circumstances, once you take your clothes off, you are vulnerable. And doing it at school could only heighten the risk. You never know how the teacher might react. They could haul you off straight to the principal's office for detention. Or worse, an unsavory individual might view it as an invitation to misbehave. Things can quickly get out of hand for a girl in such a compromising situation.

I had chosen Mr. Frenzel specifically because I had taken his introduction to woodworking class for a semester last year and had a pretty good handle on his personality. He didn't care much about academics and was only interested in his craft. But he wasn't immune to the pretty girls who passed through his classroom either. He wouldn't hesitate to get up close and personal and give his most attractive female students hands-on guidance when operating the lathe, for example.

Lucy took one last, deep breath, then sealed her fate by rushing into the classroom. She hugged the wall, stepping only a few paces into the room before coming to a stop. Looking back over her shoulder, she pretended not to notice Mr. Frenzel holding a screwdriver and making an adjustment to one of the planing tools across the room. Since the inexperienced kids couldn't be trusted around power tools, other than the lathe and a jig saw, every other tool in his class was hand operated.

Eyeing the door warily, the beautiful, unlikely intruder dropped her backpack and began to strip. Where she stood, just out of sight of the hallway but close enough to hear the students scurrying past on their way to their next class, it was understandable why she would be so intent on watching the open doorway. After kicking off her shoes and socks, she finished shedding her outer clothes and reached back to unhook her bra.

The excuse I had fed her for accidentally giving Mr. Frenzel a private strip show required her to act quickly, like she was in a hurry. Tucked away in the elective hall, his wood shop was conveniently located near the gymnasium. It was just believable enough that a harried, young cheerleader, still learning the school layout and running late for practice, might decide to use what she thought was an empty classroom as a makeshift changing room.

It didn't explain how changing in the middle of some random class was any faster than waiting until she made it safely to the locker room. Nor did it make much sense that a cheerleader would need to remove her underwear just to change into her uniform. Admittedly, the entire excuse was shaky and unlikely to hold up under intense scrutiny. But I was betting Mr. Frenzel would forget to employ his scruples once Lucy's clothes came off. I was right.

She had to pretend like she didn't know he was in there watching her undress. Even when he put down the tools and made his way around the room toward her, she forced herself not to notice the motion as her bra came down her arms to join the pile of discarded clothes on the floor and leave her topless.

Acting like she thought she was alone meant resisting the urge to cover her newly bared breasts even as she felt her bubblegum pink nipples stiffen in the open air. Instead, she simply had to keep stripping like there was no time to waste. Now, she only had one piece left to remove before she was completely naked.

Her elementary school career had included more than a few embarrassing experiences. To her credit, she had managed to make it almost a month into junior high without getting naked outside the safe confines of the locker room. Sadly, this moment would mark the end of that modesty streak.

Unable to even hesitate or risk raising suspicion, she had to rapidly peel an especially cute pair of pristine white panties, with pretty, pink trim, down those beautiful, strong legs and innocently discard them. At least her back was turned to him, so he only got to see her impressive bottom at first. The naked cheerleader then bent over and unzipped her backpack, counting silently to herself as she did so.

You would think, now that she had completed the assignment to get completely naked in front of a teacher, that she would want to get dressed again as quickly as possible. But she wasn't allowed to start putting on clothes again until she had counted down from one hundred to zero first. I made her count backward because I knew that would be harder to do in such a stressful situation and take her longer to complete. I had thought of everything! It's almost like I was getting good at this dare business.

Naked, bent over, and completely exposed, she pretended to rustle around in her backpack looking for her uniform. All the while, she recited numbers in her head as fast as she could so she could get dressed again. But it wasn't fast enough. Mr. Frenzel had enough time to make his way around the room and reach her. When she saw the shadow fall over her, she gulped knowing she couldn't pretend to ignore something as obvious as that.

"Noticing" him for the first time, she bolted upright. She didn't have to pretend to squeal in alarm. That was genuine. Then her arms and hands automatically moved to protect her most private parts, one over her puckered pussy lips and one insufficiently draped over both her breasts. They had grown too large for a mere, skinny forearm to fully contain. But then, with immense effort, she overruled her body's natural preservation instinct and forced her hands uselessly to either side. That was another tasty rule I had thrown in. No covering up until you reach zero.

Just then, the tardy bell rang out signaling that she really was late for her next class. But it was just cheer practice and Coach Easterling wasn't strict about such things. Eager to end the encounter, Lucy began counting again. Her plump little lips silently mouthed the numbers as her cheeks turned several shades redder than normal. Unable to concentrate on two things at once, she had to pause her counting again when he asked her a question.

"Excuse me, missy," he asked, unabashedly looking her bare body up and down a couple times, "would you mind explaining what's going on here?"

Using all her willpower to keep her body exposed as instructed, she delivered the excuse I had fed her just like a distressed student would.

"Yes, um, I'm sorry, s-sir. I'm a new student-I couldn't find the gym-I'm supposed to be at cheer practice right now...and...I thought this room was empty-I just needed to change real quick..."

Mr. Frenzel processing her words gave Lucy enough time to finish counting. Her task technically complete, she attempted to end the encounter right then.

"I'm sorry for bothering you," she said, scooping up her clothes and backpack and intending to flee to the nearest restroom so she could get dressed in private. But he was closer to the exit and simply slid over to fill the doorway and block her only escape route.

"Hold on, there, missy," he said, cracking a sly smile, "how do I know you're not feedin' me a load of bull hockey? If you really are a cheerleader, then you won't have any trouble proving it. Give us a little cheer, eh?" Lucy shrank back as the menacing teacher advanced on her.

He uncrossed his long arms and stretched them out toward her backpack and clothes, saying, "I can hold these for you." Don't presume him a gentleman, coming to her aid. He was clearly only removing the obstruction which was blocking the view of her budding body. The true nature of his unsavory character was revealed when he took the opportunity to cop a feel! Lucy jumped when his hands, rough as sandpaper, "accidentally" slid over the outside of her breasts as he was taking her possessions.

But looking past him, she realized something. There was an opening now! If she moved quickly, she could just slip by him and get out of the room. But where would that leave her? Stuck naked in school, huddling in some restroom while students went about their day all around her? Believe it or not, it wouldn't be the first time that had happened to her. It's kind of a long story, but something very similar had happened to her on her very last day of elementary school. Only this time, there would be no knight in shining armor coming to save the damsel in distress and bring her a dress. Also, all the developing she had done in the last six months made her even more aware of the importance of preserving her body's secrets from her fellow students.

When the leering teacher cleared his throat impatiently, she turned her attention back to him. With fleeing out of the question, her options were limited. It was wildly inappropriate for a teacher to request a student perform a naked cheer for him. But she didn't want to find out what would happen if she refused. He had every right to march her straight to the principal's office. After all, it's not like he had forced her to take her clothes off in his classroom. She was the intruder.

Lucy couldn't bear the thought of being forcibly escorted to detention her current state. How many open doorways would they pass? How many students would see her being paraded completely naked down the halls?

Her only real option was to hope he would honor his word and give her clothes back if she did what he asked and proved she really was a cheerleader. You would think, after all the naked cheers she had performed in her short career, she wouldn't be so nervous about it. But I guess it's a little different when you're performing right in front of a lecherous shop teacher.

Taking a nervous step back, the naked girl clasped her hands in front of her and forced a perky smile onto her blushing face. Clapping in time, she began a common chant, bouncing alternately on the balls of her feet with every clap and trying not to think about how much it was making her bare body jiggle with every bounce. She spun in place several times before finishing with a flourish - leaping in a near split and stretching her arms to touch her bare toes in mid-air.

Her perky smile faltered when she finished her routine and went back to just being a naked student. Luckily, Mr. Frenzel was satisfied with her humiliating performance.

"Well, missy, I can't argue with that," he grinned, dropping her things in a heap at his feet and walking away. With a chuckle, he called back, "if you ever find yourself running late again, my door's always open!"

[student]

"Well, missy, I can't argue with that," he grinned, dropping her things in a heap at his feet and walking away. With a chuckle, he called back, "if you ever find yourself running late again, my door's always open!"

Lucy isn't out of the woods yet--she hasn't even gotten to the tree line!

Now Lucy has to go to class--late--with Coach Easterling knowing that Lucy has issues with wearing clothes. Lucy comes in late to class blushing and stammering. What will Coach Easterling jump to the wrong conclusion and make Lucy practice naked in order to calm the girl down?

[Azrael]

But wait a second. He said it could be ANYONE on the cheer team. Lucy is on the cheer team.

[neverdoubted]

But wait a second. He said it could be ANYONE on the cheer team. Lucy is on the cheer team.

Damn! Either you guys are getting better at your predictions or I'm becoming too predictable. I won't confirm or deny. But if Lucy gets desperate enough, could you blame her for starting to look for loopholes?

[fuwafuwataimu]

It's always a rush to load my Dare Me tab and see the new chapter date advance!

Man, Lucy is going to end up with quite a reputation at this school, isn't she? I wonder what's going to happen when Lucy runs out of known-pedo teachers to show off to. This would be a dangerous stunt to pull in front of a straight laced teacher (or just one who wants to keep out of jail), could just imagine him calling a female teacher to tug Lucy by her ear right up to the principals office!

[fuwafuwataimu]

I'll have to wait for The Lost Years to see if an adult Lucy asks her brother, "Dare me!" Lucy is having too much fun to give up the thrilling hobby she shares with Mikey.

Let's not forget that Lucy has a condition - she's gonna have to keep showing off for the rest (?) of her life. Will it be Mikey giving the orders, though...? (I kinda hope so! )

[student]

I'm predicting that the Lost Years will resume with adult Mikey and Lucy reminiscing on when Lucy stopped asking Mikey for dares. As Lucy is in junior high and gaining more independence, she can find others to give her dares. Eventually, Lucy gets a boyfriend. With Lucy gaining a reputation, will other girls join her in her dares--as happened at cheer camp? Lucy had initiation there on top of her dare with Mikey.

[neverdoubted]

It's always a rush to load my Dare Me tab and see the new chapter date advance!

Today is your lucky day!

[neverdoubted]

Dare Me - Chapter 17 - Little Sister, Big Sister (Part 5)

That evening, Lucy avoided me, but I cornered her after dinner and made her give me a progress report. To my surprise, she hadn't even talked to any of the cheerleaders yet! I couldn't believe her nerve - openly defying me like that.

"Fine," I thought to myself, "she can stall all she wants, even refuse to participate. But she can't ignore her dare. I have a plethora of ways to motivate her to get in gear, starting with tomorrow's task."

While I pondered her next challenge, I made her tell me about her encounter with Mr. Frenzel. It was an amusing story. I was a little unnerved to hear that he had actually touched her. None of her elementary school teachers had been so bold.

The ending of her story came with more shocking news. Lucy hadn't wasted any time getting out of there. Not even bothering to get dressed, she had scooped up her things and, after making sure the coast was clear, ran down the elective hallway to the nearest bathroom to finish changing. If it sounds like she dodged a bullet with that creep of a teacher, you don't know the half of it! When she extracted her cheer uniform from her backpack and spread out her school clothes, she discovered that he had snuck her bra and panties into his overalls to keep as a memento while she was doing her nude spins.

She ended up going on to the gym with nothing to wear under her uniform! Luckily, it was just cheer practice and there were no boys around to see it. I had just given her permission and funds to buy a couple bigger bras at the start of school and was not pleased to hear she had already lost one of them. I vowed to reckon with that later before turning my attention to the next order of business.

"Well, it looks like you failed the assignment. You know what that means. Who do you want to surprise tomorrow, student or teacher?" I asked.

Fully intending to teach her an unforgettable lesson about defying me, I was pondering a few especially embarrassing options for her next task. But her odd response threw me for a loop.

"Is tomorrow gonna be the last day?" she innocently asked with a look of genuine bewilderment.

Something was…off. Instead of giving her a task, I paused to reassess the situation. What was I missing here?

"...you do know you have keep doing tasks until...you know," I cautiously answered.

I watched her eyes go wide as the comprehension slowly dawned on her face. Then the adorable blush came. Reading her reaction told me everything I needed to know to figure out what was going on.

She wasn't accustomed to dividing her energies like this during a dare and had lost track of the real assignment. Usually, the dare itself was the assignment and surviving it warranted all her attention. But this time, I had made the humiliating task just a punishment if she failed to complete the actual objective.

So, that's why she hadn't done any work to secure a cheerleader for me! It's not that she was actively defying my instructions, she just didn't have a handle on the new dynamic yet. Facing down not just one more day of humiliation, but a limitless number, her shoulders slumped, and she muttered, "teacher".

Believe it or not, I am capable of showing mercy. To help her out, I called an audible and decided to give her a less difficult task just this once. That would give her another chance to complete the real assignment before the consequences got more severe. Because it still had to involve getting naked in front of a male teacher, I wouldn't say the task was any less humiliating. But at least she was going to have some female support this time.

Having finally gotten my little sister to focus on the right goal, I slept quite soundly that night. Now that she was on the case and properly motivated, I had to assume my lifelong celibacy would be coming to an end very soon. I awoke with a massive erection and a huge smile. Hang in there, Mikey Jr. Perhaps today will be the day!

I doubt Lucy had as peaceful a slumber. She probably tossed and turned all night wrestling with the predicament I had put her in. She couldn't afford to carelessly let another day go to waste.

The next morning, I awoke to find she had, sometime during the night, slipped a cd case under my bedroom door. A sticky note on the front only had one word, "sorry". I don't know if she felt guilty for the dare she had given me and was trying to make up for never making it "worth my while" like she had promised. Or maybe she was just trying to stay on my good side so I might go easy on her with her current dare. Either way, she failed.

While mix tapes on cassette were a common thing, mix cd's were relatively new back then. You had to have special equipment to make them. I don't know where Lucy got the knowledge or how she got access to a computer to make these - the case held two discs - but she must have done it wrong. The disks were unlabeled and apparently defective. They both threw up an error when I put them in our cd player.

Did her peace offering earn any leniency from me? Fat chance! Shoving the case into my desk drawer, I stood up and got dressed. It was earlier than usual, but I had gotten up early on purpose. After getting ready for school, I made my way across the hall to Lucy's bedroom. It was time to reveal another wrinkle. She still had to pay for losing her bra.

"Wake up, Goosey," I called, barging into her room, and rudely turning on the overhead lights, "I have a new rule for you."

Rubbing her tired eyes, she forced herself to sit up and pay attention. It wasn't the first time I had disturbed her slumber in the middle of a dare. Usually, that meant trouble.

"Since you apparently can't be trusted to take care of your expensive underwear," I explained, "until you complete your dare, you aren't allowed to wear panties or bras to school anymore."

"Mikeeey," she started to complain, "please don't make me do that. It's not fair!"

"It is too fair," I shot back, "you know how tight our budget is. And you just lost a brand-new bra and perfectly good pair of panties! Clearly, you can't be trusted to keep up with such things... I tell you what, if you want to go back to Mr. Frenzel and ask him to give back your underwear, I'll let you wear them again. But until then, forget it."

She groaned and threw herself backward onto her pillow, covering her face like she was in pain. I'm sure she never wanted to set foot in that creep's classroom again. And she certainly never wanted to have to discuss the whereabouts of her missing underwear with him!

When she heard her closet door, her eyes shot open, and she rolled over.

"Wait, what are you doing?" she asked.

"Helping you pick out an outfit for school," I replied, "It's going to be such a nice, warm day. You shouldn't need much."

She groaned again. Now I think she really was in pain.

[student]

There is a fine line between motivating someone and being mean. The person being motivated can't tell the difference.

Will this be the final dare Lucy asks Mikey to provide?