Chapter 1 - Pajama Hide and Seek
Chapter 2 - The Birthday Suit
Chapter 3 - Blind Squirrel
Chapter 4 - Mr. Beski
Chapter 5 - The Sleepwalker
Chapter 6 - Lucy's First Bra
Chapter 7 - The Fitting
Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle
Chapter 8 - Heat, Pressure, Time
Chapter 9 - Lucy makes a Diamond (Part 1) (Part 2)
Chapter 10 - History Buff (Part 1) (Part 2) (Part 3)
Chapter 11 - Severance Package (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9)
The Lost Swimsuit Saga
Chapter 12 - My Nightmare (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10)
Chapter 13 - Hardship Study Buddy (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10) (Part 11) (Part 12) (Part 13) (Part 14) (Part 15) (Part 16) (Part 17) (Part 18) (Part 19) (Part 20) (Part 21) (Part 22) (Part 23) (Part 24)
Chapter 14 - Mikey Gets a Dare (enm) (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10) (Part 11) (Part 12) (Part 13) (Part 14) (Part 15) (Part 16) (Part 17) (Part 18) (Part 19) (Part 20) (Part 21) (Part 22) (Part 23) (Part 24) (Part 25) (Part 26) (Part 27) (Part 28) (Part 29) (Part 30)
Chapter 15 - Doctor's Orders (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10)
Chapter 16 - Wait, What Happened at Camp? (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10) (Part 11) (Part 12) (Part 13) (Part 14) (Part 15) (Part 16) (Part 17) (Part 18) (Part 19)
Chapter 17 - Little Sister, Big Sister (Part 1) (Part 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) (Part 8) (Part 9) (Part 10) (Part 11) (Part 12) (Part 13) (Part 14) (Part 15) (Part 16) (Part 17) (Part 18) (Part 19) (Part 20) (Part 21) (Part 22) (Part 23) (Part 24) (Part 25) (Part 26) (Part 27) (Part 28)
future additions (only if there's enough interest, subject to change)
Chapter 18 - The Lost Years
Chapter 19 - Goosey Lays an Egg
Chapter 20 - The Summer of a Thousand Diamonds (End)
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Copyright NeverDoubted. No usage or copy without permission.
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Author's Note: Chapter 1 does not actually contain a dare, but it does set the stage for what is to come. If you're here for a dare, feel free to move along
![Wink ;)](./images/smilies/icon_e_wink.gif)
Dare Me - Chapter 1 - Pajama Hide and Seek
It started with a slightly creepy babysitter. I don't recall much, but his name was Kevin and he only watched us twice. He must have been in his late teens and was chosen because he had a car and was willing to drive himself. And probably because mom was desperate. She never paid enough to keep a regular around.
It was one of the last times we had a babysitter. Within a year, I guess, mom decided I was old enough to watch us. Or maybe she just ran out of money. She did that a lot. Anyway, he wouldn't have been memorable except for the things he got my sister to do which awoke something inside her and changed everything.
I was almost 11 at the time which would have made her 9. Babysitters typically ignored us while we watched TV or played board games (we couldn't afford video games). But Kevin took a peculiar interest in us. The fact that he was so keen to play Connect 4 or Uno with a 9-year-old should have served as a warning. Even I couldn’t stand to play more than a few rounds with my sister before getting bored at that age.
But Kevin persevered. That he was game for anything my sister and I pulled out of the closet (even if some of the pieces were missing) probably bought him a healthy amount of goodwill and trust. I didn't realize until much older that he had a perverse ulterior motive and was building a rapport for a reason. It wasn't until almost bedtime that he finally made his move.
He declared the evening to be over by announcing "I know you don't want to, kiddos, but if I don't get you cleaned up and tucked in bed before your mom gets home, I'll get fired."
Of course, we immediately started to protest. For once we'd actually had an entertaining evening and didn't want it to end.
He offered a compromise. "I tell you what, I know a way we can make it fun and get in one more game. We can turn it into a contest."
I've always been pretty competitive and figured I could beat my little sister at whatever game he proposed. It sounded like a good idea to me, and Lucy nodded along.
"OK" he continued with a conspiratorial gleam, "this game is called 'Pajama Hide and Seek'. I want each of you to go get your PJ's and meet me at the front door."
As we each bolted off toward our bedrooms, he called out behind us, "This is not part of the contest. You don't have to rush. Don't forget clean underwear!"
I dug around in my closet and came up with a matching set of pajama shorts and shirt and some underwear and headed to the front door. Lucy arrived at the same time and had chosen a simple nightgown and a pair of panties. Kevin was fiddling with a kitchen timer. He collected our PJ’s then began explaining the rules.
"We used to play this game all the time growing up." that was surely a lie, but we were too gullible to notice.
"When I say 'Go', Lucy, you will go take your bath. Michael, you will go hide Lucy's PJ's somewhere outside. Now, it has to be on a front porch, and it has to be somewhere on this street. Understood?"
We both nodded as he set the timer to 20 minutes and handed it to me along with Lucy's PJ’s, then continued.
"Michael, you have to be back before the timer goes off or you're disqualified. Then you'll switch and Lucy will hide your PJ's while you take your bath. And no cheating by hiding them, either. The PJ's must be visible from the street. Ok, ready? Go!"
He started the timer and opened the door, calling out "Good Luck" as I set off into the night.
We lived near the middle of our street, so I just kind of picked a direction and started walking. Our neighborhood was pretty nice. It was full of retirees who must have made lots of money in their career. We really couldn't afford to live there, but it was the one thing of any value dad had left us.
I had about 30 houses to choose from, and about half had their front lights on. I figured it would be better to pick a house without a light to make it harder for Lucy to see from the street. I wanted every edge in this contest. But then I found something even better. Someone had built a little playhouse for their grandkid and placed it in their front yard off to the side.
It did technically fit all the rules Kevin had laid out. It was on our street, and it had a small porch. I folded Lucy's nightgown and placed it on the porch with her panties on top. It was completely in shadows but was still visible from the road if you were looking right at it.
I checked the timer and made sure to get back to our house with plenty of time to spare. Lucy came down wrapped in a towel. Her medium-short blonde hair was still wet and clung to her. It carried a scent of the strawberry shampoo she liked to use.
Kevin reset the timer and handed it to her along with my PJ's then said "Ready, set, Go!".
When Lucy bounded out the doorway, a strange thought briefly crossed my mind as I turned toward the stairs. "Did our babysitter just send my sister out into the neighborhood wearing nothing but a towel?"
But I didn't think much else of it since Lucy hadn't seemed bothered.
When my bath was finished, I dried off, wrapped myself in a towel, and headed downstairs like Lucy had done a few minutes earlier. When she got back, she was breathing heavy like she had been running. I took that as a clue that she must have picked somewhere far away to hide my PJ's. Kevin gave her a minute to catch her breath, then led us back onto our own porch and explained the rest of the game.
"The final rules are simple. Whoever is the first to find their PJ's and make it back to this porch is the winner. The winner gets a reward that the loser has to pay."
My heart started beating faster. I just knew I was going to win. I was a faster runner and there was no way Lucy was going to find my hiding spot. Kevin must have noticed my confidence or Lucy's lack of it because he decided the playing field needed rebalancing at the last moment.
"Now, since Lucy is younger, she will get a 5-minute head start" he announced.
"5 minutes!" I thought in exasperation. That was totally unfair. You could make it the entire length of the street in 5 minutes, even with a stop at every porch. I started to protest, but Kevin was having none of it.
Lucy beamed with delight at her unexpected turn of fortune. She started toward the steps to begin the seek but Kevin had one last twist in store.
"Nuh, uh, uh, Lucy, darling. You have to give me your towel before you can begin." he said with his hand outstretched.
Lucy's eyes went wide as saucers and I'm sure mine weren't much smaller. This game wasn't just about two children going up and down the street on a scavenger hunt. This was about two naked children desperately searching right outside every neighbor’s house for something to wear.
When she hesitated, Kevin added "I'm starting the timer now. Michael, you can begin when you hear the beep."
That was just the thing needed to motivate her into action. She couldn't lose her time advantage. So, in a flash, she threw off her towel, tossed it into Kevin's waiting hand, and took off in the wrong direction (yes!). Her skinny white bottom practically left an after-image on the dark canvas of the night. I probably would have laughed at the performance if I weren't shortly doomed to repeat it myself.
As my eyes adjusted, I was able to see further and further. At one point, I saw her streak past on the other side of the street. She was definitely in a hurry. It was abundantly clear that she was naked, which made me think about my own impending situation. I just had to hope the old people in our neighborhood didn't have as good of eyesight as me and were hopefully already asleep. I could be in a lot of trouble if one of them caught me poking around their porch without any clothes on.
Then a couple minutes later she came back up on our side of the street. She was still naked, which meant she had skipped right over her nightgown, and was starting to look worried. That's when I knew I had won. She had already made a complete circuit of the street and never saw where I hid her nightgown.
Feeling cocky, I quietly called out a taunt, "What's the matter, little girl? Did you lose your clothes?"
I could practically see her blush and could definitely read her body language when, in an act of desperate futility, she wrapped her little arms around her torso. She did not answer but stuck out her tongue in my direction then turned straight ahead and stomped away to begin her second loop.
Finally, the timer beeped, and I whipped off my own towel and took off. It was a surreal feeling to be enveloped by nothing but the night. But I didn't have time to explore the feeling. I had a mission to complete. I set off toward what I estimated to be the furthest house from us, stopping to carefully gaze at each porch along the way just in case.
If I guessed correctly, I could be back to our house fully dressed and take a front row seat to resume watching my naked sister aimlessly wander the neighborhood. Alas, it was not to be. The prime porch I had guessed was bare. Maybe my sister wasn't so predictable after all. I picked up my pace and began more urgently searching for my clothes.
When I passed the playhouse, I checked my own hiding place to make sure Lucy's nightgown was still there. But I was careful not to slow down or draw attention to it.
When I had made my own complete loop of the street, I started to get nervous. I had made sure to check every single house. There was no way I would have missed it...unless. Maybe…she cheated. She must have hidden my clothes somewhere not visible from the street. Of course!
I set out once again, this time checking around hedges and other obstacles. One time a car came down the street and I thought my mom was home. Was I going to have to explain that our babysitter had tricked me and my sister to take off all our clothes and run around outside? But luckily it was only another neighbor, and I was able to hide until it passed.
When I got back to the furthest house, I was starting to despair enough to wonder what the punishment for losing would be. But just then I saw something lumpy in the shadow behind a giant flowerpot. It was my PJ's!
Victory!
I quickly got dressed and started strutting back home. Then I remembered that the contest didn't end until one of us made it back to our porch, and I started running. I ran into my sister coming the other way. She was completely out of breath and frantic. When she saw that I was already dressed, her scrawny little shoulders drooped in defeat.
"Mikey, you cheated!" she accused with tears welling up in her eyes. "I checked every porch 3 times!"
"I did not cheat. You just can't admit you're bad at looking for things." I teased.
"Ok, fine", she challenged, "then show me where you hid my PJ's. We'll let Mr. Kevin decide."
I accepted and we walked back up the street together; I, fully clothed, savoring my victory lap. My still naked sister trudged along beside, a vanquished foe hoping the babysitter would grant her a last minute reprieve by ruling in her favor.
But when I led her and Kevin to the playhouse, Kevin was on my side.
"Sorry, kiddo." He said with an air of authority, "He didn't break any rules. That porch is pretty small, but it still counts."
"B..but, it's not visible from the street. He cheated!" Lucy appealed one last time.
"You cheated" I shot back. "My PJ’s were behind a flowerpot! How is that fair?"
"They didn't start out there. I only moved them once I thought Mikey was cheating." Lucy offered feebly, but she was only hurting her own case.
Finally, she admitted defeat and went to retrieve her clothes. But Kevin got there first.
"Hold on there, kiddo." he declared as he tucked her nightgown safely under his arm. "You lost fair and square. And this is part of your punishment. You may not wear anything the rest of the night. Furthermore, you must make your brother breakfast in the morning and serve it to him in bed dressed exactly as you are right now. That is the reward you must pay to your brother because he won. Only then, once breakfast is served, may you get dressed again. Do promise to honor these terms?"
Lucy flinched and her eyes darted around as the magnitude of her punishment sunk in. But to her credit, she raised her glassy eyes to meet his and solemnly whispered "I promise", then stoically turned and headed for home.
When we got home, Lucy was subjected to another round of humiliation as her naked body was revealed under the harsh indoor lights. She was still very much a kid and didn't have much to look at. She was all limbs and very skinny. But it was still a novelty seeing a girl without any clothes on, especially the intriguing little crease between her legs. And I suppose most people would call her cute with her striking blue eyes and fair skin, even though I mostly thought of her as just a pest at that age. She certainly hadn’t sprouted yet into the head-turner she became as a teenager.
Even though it was well past our bedtime, Kevin found a few ways to extend her humiliation. He made her carry her own nightgown and panties upstairs and put them away, then come back down still naked and put every toy and game we had gotten out back in the closet while he and I just watched. Then he made her get a washcloth and clean her and my feet which had gotten dirty from running around outside.
To her credit, Lucy obeyed every request without hesitating. She wore a light blush on her cheeks; the only outward indication that she was embarrassed to be naked around her brother and her male babysitter.
Finally, out of ideas, Kevin sent us to bed. I was exhausted and fell asleep immediately. I could only assume he had sent my sister to bed naked.
And lest anyone accuse her of ever breaking a promise, let me assure you, I was awoken the next morning by my sister standing over my bed holding a tray of cereal, a pop tart (all she was allowed to cook at that age), and some juice. And all she was wearing was a light blush on her cheeks and a happy smile.