Dare Me - Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle

[neverdoubted]

Contents:
Part 1
Part 2
Part 3
Part 4
Part 5
Part 6
Part 7 (end)

Author's Note: This story is part of the "Dare Me" universe. It is set after chapter 7. Might be useful to read those first to understand the backstory. For those wondering about the vote, a truckload of ballots was dropped off after the poll closed. This story won in a landslide. You'll thank me later.

And now, by popular demand...

Dare Me - Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle - Part 1

That fall, for the first time, Lucy and I were in different schools. As we settled into the routine, we both seemed to be flourishing. I perhaps was taking a bit longer to adjust to my new environment. But Lucy, as the big fish sixth grader in her small pond of elementary school, practically ran the place. Popular kids gravitated to her, which I guess made her popular too. It didn't hurt that she had done a lot of growing over the summer and was a classic beauty. The best-looking girls tended to flock together for some reason.

She attracted lots of friends which created an interesting new dynamic around our house. I never knew when I got home from school which of Lucy's cute classmates would be hanging around. I think I held a certain intrigue for them as the mysterious older brother who was a...teenager. Their eyes would track me everywhere I went, and I often heard fits of giggles pass between them when I left a room. I admit, I tended to strut around them, enjoying the attention; especially since none of the girls in my school showed the least bit of interest in me.

Mom seemed relieved that we were doing so well in school. One less thing for her to worry about. She was having a hard time at work, and I often heard her complaining over the phone to her sister. She was on a sales team that had landed some big clients recently. Her boss always took her with him on sales calls if he thought an attractive woman at the table would make a difference.

She told Aunt Julie about the inappropriate comments he made about her, that her clothes were too frumpy, and she should open more buttons on her blouse. Unfortunately, mom had a hang-up about authority figures and tended to do whatever he suggested. Despite all her hard work to learn the product and be a good salesperson, the type of clients her boss targeted only saw her as a piece of eye candy.

It didn't help that her current position did not pay commission. She couldn't prove it, but she suspected he was passing over her for promotions and holding her back so he could keep the commissions for himself. Aunt Julie called him a "slimeball pig" and, from mom's descriptions, I couldn't disagree. It sounded like he was a jerk who treated her like a glorified secretary, or worse a piece of meat, and stole the rewards of her labors.

One day, in early October while we were sitting with mom around the table, the subject of Halloween came up. I was in that weird in-between age where I felt too old for trick-or-treating, but not old enough to join the party scene. I said I could find some friends to hang out with and maybe we would hit a haunted house.

Lucy, on the other hand, was in the Halloween sweet spot. She was old enough to have stronger opinions about her costume choices. The prospect of getting to wear make-up and do her hair up special was exciting. But the child in her was just as excited about getting to eat a ton of candy.

There was only one problem. Her Halloween costume had to be just perfect, and Lucy tended to have expensive tastes. She would never accept the pathetic cookie-cutter selections at Wal-Mart. But we didn't have any extra money for perfect. That's when mom, in an attempt to think outside the box, made an interesting suggestion. Why not have Mr. Beski make a costume?

It actually made a lot of sense. Mr. Beski had made her a beautiful dress over the summer which was a huge hit at school. Whenever she wore it, she got lots of compliments and proudly told people it was a "custom, designer dress" (whatever that means). Despite the humiliation she had endured to get it, Mr. Beski had certainly delivered. He was clearly a skilled artisan, and as a lonely retiree, he would probably jump at the chance to make something else for her. It's not like she could make a better costume herself.

Since we couldn't afford the boutique stores and Lucy wouldn't consider the imported cookie-cutter crap, I guess she was willing to swallow her pride and ask him for help. Mom couldn't help with money, but she did offer something else to make the evening special.

"I don't have anything scheduled for work that weekend." Mom said, then added "Do you want to invite some of your friends over to spend the night on Halloween?"

Lucy was ecstatic and immediately started transforming mom's simple offer into a Halloween sleepover spectacular. She asked how many friends she could invite. Could they make cookies? What about decorations? Balloons? Entertainment? She had seen a home makeover kit at the store. And of course, there was dinner to think about. Maybe a taco bar? NO! Pancakes, even better!

Mom shot me a worried look. Lucy was getting carried away like she always did, and she needed someone to step in and help manage expectations. I was the closest thing she had to a co-parent.

"Pancakes...and cookies?" I interjected myself into the conversation, "don't you think that's a little much? I mean, there will already be plenty of candy. I think you should plan something simpler. Trick-or-treating is the main entertainment. Mom can have a frozen pot pie ready when you get back and everyone will probably be pretty wiped out by then."

Lucy seemed to accept that logic and withdrew her unreasonable requests. After all, it was better than nothing. Now the only remaining point of negotiation was the number of attendees. She insisted on inviting her two closest friends, Grace, and Katherine. But she was shooting for at least three more. she tried to argue that she had to invite them all. It wouldn't be fair to leave one out and invite the other two. But mom looked stressed. If I was gone at a friend's house all evening, she alone would be woefully outnumbered by six girls hopped up on candy. I determined it would just be too much for mom and made Lucy settle for just Grace and Katherine. She was still overjoyed and ran to the phone to invite them.

Once the party was confirmed, she now had to come up with a costume idea. Naturally, the idea of matching costumes came up. But what could three girls go as for Halloween? The Three Musketeers? Not exactly exciting for three 12-year-old girls (or 11.9 in Lucy's case). Then there were the old traditionals; ghosts, vampires, witches. But nobody wanted to wear green paint on their face. For a while, they were seriously considering asking Mr. Beski to make them into black cats. It probably would have made a cute sight. But then, Lucy got hooked on a vision and couldn't let it go: devils and angels.

Not bad, but how do you make it work with three people? She brainstormed and came up with a clever solution. One would dress up as a devil while the other would be an angel. And Lucy would stand in the middle dressed up as half a devil and half an angel; like her soul was hanging in the balance and the other girls were each trying to lure her to their side.

It was actually kinda genius. To do all that yourself would be very expensive. Basically, you would have to buy two complete costumes, cut them down the middle, then sew the two halves back together. Fortunately, they had access to a very skilled tailor who was willing to make it from scratch and didn't charge for labor.

She went over after school the next day to make her request in person; fully dressed, this time. If you're wondering why, it was worth noting that Lucy wore clothes to visit Mr. Beski...it's a long story. He was delighted and agreed on the spot. He even refused our offer to pay for the fabric. His only request was that the three girls submit to a measurement’s session and perhaps a final fitting when the time got closer.

Lucy balked at that request. She knew what Mr. Beski's measuring session was like and didn't want to submit her friends to that humiliation. Instead, she offered herself and asked if he could just use her measurements as a pattern for all three. He reluctantly accepted and had Lucy strip naked so he could update his measurements for her. It had been a couple months since he had last taken them, after all. Once that was done, it looked like smooth sailing. But almost immediately, things started to go wrong, and they kept going wrong right up until Halloween night. And Lucy's Halloween Sleepover Spectacular nearly turned into a nightmare.

The first setback could have been chalked up to cultural idiosyncrasies. I had agreed, after she begged me, to accompany her over to Mr. Beski's house a couple weeks later to check in on the progress. It turns out old Hungarians have a different idea of what a devil looks like. His first attempt at that costume looked more like an ugly sheep. It was very lumpy and unattractive; nothing like Lucy's original vision. She was expecting a modern, American devil.

She ran home and came back with a magazine she had bought of costume ideas. She explained that all three costumes had to have a cohesive look. But they also needed to be cute. That was the whole point of having them custom-made. She showed him a bunch of different costumes and called out various things or features she liked about them. I was kind of bored. Why hadn't she done this before he wasted his time and money on something that would have to be thrown out?

Slowly, Mr. Beski started to get the idea. He suggested starting with a leotard base and working from there. I noticed he kept turning back to one page that had a spread of sexy costumes for adults; probably because there were lots of costumes on that page with a leotard base. I had already perused that page on my own time so I knew what it contained. Slutty nurses, sexy mummies, plenty of skin and miles of gauze. There was even one woman dressed like an angel. But the fabric of her top was so sheer, she had her hands over her breasts to keep the photo from being too racy for public consumption.

He asked if he could keep the magazine for reference. As expected, he would have to throw out his work and start over. He would also have to order all new material, white for the angel and red for the devil. That is, until Lucy suggested black with red trim for the devil. She said black would make a better contrast on Lucy's middle costume. It was going to be close, and they would have to scrap the rehearsal fitting, but he estimated he could still have them all done in time for Halloween night.

While Mr. Beski did the bulk of the work, Lucy and her friends were far from idle. Aside from the main costume which he was working on, they were responsible for shoes and accessories. The girls spent every day after school (and too much money) on it. They tried to make a pitchfork before giving up and buying one along with a headband they found with red horns on it. They also planned to get a shiny new pair of black open-toe shoes with straps running up her legs and even a little heel.

For the angel, they were actually able to build a harp out of cardboard with string for the, uh, strings. They also got her a white skirt which they glued cotton balls all over to look like she would have a cloud floating around her wherever she went. A pair of white ballerina shoes would make for appropriate footwear. And to top it off, she would get a sparkly, silver halo. The decision on tights or socks was still up in the air and could be a night-time decision.

I wasn't sure how Lucy's accessories were coming together. For example, we couldn't afford two new pairs of shoes just so she could wear one of each style. But she kept working on it and I expected she would figure something out. Of course, I wasn't involved in any of the shopping or preparation. I was in the dark about it all until Halloween night. However, I did notice mom's looks of distress whenever they returned from yet another supplies run. It wasn't just the costume. There was also hair and make-up to consider. What a racket!

One day, I guess it suddenly occurred to Lucy to ask me what I was going to be for Halloween. She had wanted to run to the store again, but mom was gone to work. When I told her I didn't even know if I was going trick-or-treating this year and was probably going to just hang out with my friends, she was stunned. Like she didn't even know that was something people did. When she realized for the first time that I probably wouldn't be around for Halloween evening, she started pouting.

"Come on, Mikeeee!" she whined, "You have to go trick-or-treating. Why don't you go with us?"

"As what?" I replied. "I don't have a costume. Besides, you girls have a whole theme. I would just look out of place."

I hadn't meant to make her pout, so I tried to cheer her up. "Hey, look on the bright side." I said, "Maybe your costumes won't be ready in time."

She looked up at me in fright. Oof, that backfired. I quickly tried to salvage things by clumsily turning it into a joke. "I meant, uh, if they're not ready, you won't have anything to wear either. Then we could all go together, as nudists!"

Lucy blinked at my salacious attempt at humor. But at least her pouting stopped. She pondered for a moment then said something unexpected.

"They like you; you know? Grace and Katherine. They think you're cute."

My heart skipped a beat. I tried to play it cool.

"Oh, yeah?" I asked.

"Yeah, " she replied, "they keep asking if you have a girlfriend. And they were hoping you were going to be here to hang out on Halloween. Oh, well, I’m sure someone will take pictures. I think Grace has a Polaroid camera."

HOLY SHIT. Katherine and Grace think I'm cute?! What did she mean by "they keep asking"? As in, they couldn't stop asking about me? I desperately wanted to interrogate her for more information, but instead I managed a hopefully disinterested "Hmm".

After about a minute, I excused myself and went to ponder the implications alone. I even considered cancelling my own plans. But how desperate would I look in front of my classmates if they found out I bailed on them just to go spend the evening with some sixth graders who had shown some interest in me?

But Katherine and Grace were no ordinary sixth graders. Other than Lucy they were, by far, the hottest girls in their school. If Lucy was a 10, they were 9.9's. I didn't go through with cancelling, but I did very seriously consider it and had trouble falling asleep that night.

When the big night finally arrived, Lucy had so much nervous energy, she looked like she would explode. She bounded from room to room like a caged kangaroo. At one point, she literally bounced off the wall. Remember when I said the whole event was almost a nightmare? That was the reason for her nerves. Mr. Beski had called earlier in the day to say the girls' costumes still weren't ready. He was working furiously and would call to let us know when we could come pick them up. The other girls were due to arrive any second and would need time to get ready before hitting the neighborhood.

I was about to walk out the door to bike to my own evening festivities when the phone finally rang. Lucy beat everyone to it and answered it with a glimmer of hope. But it was just mom's boss.

"Why would he be calling so late?" mom wondered aloud, then took the phone from Lucy. My sister didn't move away, though. She needed mom to get off the phone quickly in case Mr. Beski was trying to call. As she listened to the man talk, mom's face gradually turned from happiness to dismay. Lucy was watching, too. And by the time mom hung up, Lucy was bawling. She didn't even know what had happened yet, but she just knew the news was bad.

Apparently, A couple of clients were grumbling about not being appreciated. They played poker with mom's boss all the time. So, he figured an evening of explaining the benefits of our product over a poker table could smooth things over. He had booked a conference room at a hotel about an hour away and they were going to host these clients for an evening of poker and schmoozing.

Mom looked so distraught. She was ready to help her daughter have a spectacular and memorable Halloween evening and sleepover. And now her boss had just called an emergency overnight business trip. Worst of all, she wouldn't be any help. She didn't even know how to play poker! But her boss made it clear that attendance was mandatory. Or she would be fired. Lucy somehow started crying even harder as her evening prospects circled the drain. What else could I do?

"It's OK, mom. You go on. I'll stay here." I offered. I was a little bummed to be missing out on the haunted house, but I couldn't stand to see my sister so devastated.

Lucy continued lightly sobbing, but it looked like the waterworks were slowing down as she tried to follow what was happening. Had she been in her right mind, mom would have called the other parents to see if the sleepover could have a last-minute venue change. Or maybe let me be in charge for trick-or-treating then send Katherine and Grace home.

Had she been in her right mind, she would have told her boss to shove this last minute "business trip" which was really an excuse to play poker with his buddies on Halloween night up his ass. But none of that happened. Instead, she turned to me, her surrogate co-parent, and said "Thanks, Michael. I know you're disappointed. I'm disappointed, too. But you know how much tonight means to Lucy."

I nodded solemnly. When Lucy realized what was happening, she ran over and gave me the biggest hug which made it all worthwhile. Mom said, "Lucy, Michael is giving up his night for you. You better think up some way to make it up to him."

Between sniffles she said, "Oh, Yes, mama! I will, I promise!"

Just then, two things rang at once: the doorbell and the phone. The evening had begun!

[neverdoubted]

Dare Me - Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle - Part 2

While Lucy went to welcome the other girls in at the front door, mom talked to Mr. Beski on the phone. The costumes were, in his words, "as ready as they can be". The girls appeared at the doorway to the kitchen talking a mile a minute. It looked like Lucy had rallied and was now, once again, excited about her evening. Katherine and Grace were each carrying an overnight bag as well as make-up and hair supplies. I bashfully said "hi" to them (they think I'm cute!) then excused myself to go get the costumes.

Mr. Beski invited me in. He was muttering to himself about how he didn't like being rushed. I was worried he would invite me to sit down for tea or something. Did he know the girls were back at our house waiting for their costumes right this minute?

"T'vas very difficult, dis materiel." he was trying to explain through his thick accent. He seemed particularly concerned about Lucy's costume. Apparently, the two different colors of her fabric had been a challenge to sew together without an ugly seam showing right down the middle. He had resorted to hand-stitching it which is why it had taken so long. But I wasn't here for a soliloquy about his difficulties.

I swept the three costumes off the table and into my arms, underestimating how light they would be. It caused my arm motions to be exaggerated and I swung them too high when I lifted. I heard something tear as one of the costumes snagged on lamp that had been bolted to the worktable. It was Lucy's costume. Mr. Beski flinched and showed me where I had ripped out some of the stitching at the collar. He said I had to be more careful and explained it was very delicate, only good for one night.

He offered to fix the tear, but I knew we didn't have time for that. It didn't look too bad to me. Where it would be on her, right in the middle up close to her neck would almost look intentional. I thanked him and said he could see the girls later when they made it around to his house. I rushed back home to see mom had thrown together her own overnight bag for her business trip. She looked disheveled and tired but assured me she would be fine. I told her not to worry and that I would take care of things here, which seemed to calm her. She thanked me again and then she was gone. My heart picked that moment to start pounding, for some reason.

As I climbed the staircase to deliver the girls' costumes, constant peals of laughter wafted down from the direction of Lucy's room. I knocked on her door and everything went quiet inside. Lucy was wearing a robe when she answered the door. Katherine peeked around from behind the door.

She had straight black hair that would have come down to her shoulders, except it curled in the bottom and framed her face. Her big, brown eyes studied me with an occasional slow blink which accentuated her long eyelashes. She was lithe like a cat and had a devilish grin on her face which came with the cutest dimples. She was mostly concealed behind the door, but I could still see one strap of her training bra on her shoulder. That meant she wasn't wearing a robe and was likely just in her underwear. She played with the doorknob, moving the door back and forth, teasing me with the chance of letting me have a peek at what was behind it.

Just then I noticed some motion on my periphery. I turned just in time to see the briefest white flash disappear. It was Grace. She had gone to the bathroom and was coming back. Since she, too, was only wearing her underwear, she must have fled when she saw me standing in the hall. Sure enough, a few seconds later, she re-emerged, this time wrapped in a white towel, and came toward me.

Grace was the shortest girl in the trio, if only by an inch or two. And while the towel did cover everything important, I was enthralled by the way she walked. Her feet fell in a straight line causing her legs to almost cross over each other and her hips to swivel back and forth as she walked. And even though she wasn't really showing anything intimate, other than maybe the bra straps peeking over the top, there's something alluring about a girl in a towel.

Grace's hair was straight, similar to Katherine's only a bit longer and blonde. It also didn't curve in at the bottom, but just rested on her shoulders. She wasn't as blonde as Lucy, though. More like the lightest shade of strawberry blonde.

She stared at the floor as she approached, squeezing the top of her towel in one fist. She kept darting her eyes up at me nervously, as if I was a viper who would strike if she let her guard down. She finally acknowledged me with a blushing smile as she passed by and disappeared into Lucy's room, her eyes were big and pale blue like the sky, not as piercing as Lucy's.

Lucy said "Thanks Mikey" as I handed her the costumes. Katherine added a playful "Yeah, thanks Mikey!"

Lucy then instructed that they were going to need the entire upstairs to get ready. So, would I please stay downstairs and give them some privacy? I wanted to explain that I wasn't spying on them and meant to give them space as soon as I had delivered their costumes. But it was pointless to argue, so I just I agreed. As soon as her door closed, the entire room exploded in a cacophony of giggles.

I left the upstairs to the girls and went to double-check the instructions for the pot pie that mom had already started thawing. I set the oven preheating, then settled in the living room to wait, occasionally answering the door for an early trick-or-treater. It was still light out and only the very young children were out at this time. Since our neighborhood was full of old people, it didn't get nearly as much traffic on Halloween night as others nearby, but there were always a few kids.

Knowing Lucy, I had expected to be waiting a long time. She was practically 12 and already took forever to get ready. I couldn't imagine what it would be like once she was a teenager. But she surprised me when, only few minutes later, I heard her yell "Miiiikeeeeeeey, we neeeeed you!".

What now? I jumped up and rushed to her aid. This time there was a lump in my shorts as well as my throat.

Lucy met me at the door to her bedroom. This time she only opened it a crack and was hiding behind it, but I could tell she was now wearing her costume. "We need your opinion on something, Mikey." she said, then slowly opened the door. Katherine and Grace were standing across the room in their costumes, awaiting my entrance. Lucy let me enter then went over to stand between them.

They were far from ready. They hadn't even started on their hair or make-up. But they must have been eager to try on their costumes, first. The effect was exactly as Lucy had envisioned. Katherine stood on her right side in her black and red devil costume. Grace was on her left dressed in the pure white of an angel. And, of course, Lucy, with her half-and-half costume, belonged right in the middle. It reminded me of those stories where a little angel and devil would each sit on a person's shoulder and act as their conscience. Grace and Katherine were both vying to attract Lucy to their side, and by the colors she was wearing, her conscience was split 50-50 at the moment.

As far as Halloween costume theming went, it was a grand slam. But in the execution, there were a few glaring issues. Most importantly, all three costumes were practically transparent. I stared at the girls for a few seconds wondering if I had suddenly been granted the superpower of x-ray vision. Then I realized my eyes were bulging and forced myself to blink.

Mr. Beski, may every blessing be upon him, had tried to follow Lucy's instructions. He had indeed made all three costumes in a leotard style like the magazine she had given him. But he must have chosen his material from one of the "adult" pages. The leotards outlined the girls, fitting their bodies like one-piece swimsuits, except with long sleeves attached. However, they did nothing to keep their bodies from showing through. The only variation between each was the color of the fabric.

Of the three, little Grace was the most covered because of her cotton ball cloud skirt. But her upper torso only had a thin layer of white gauze. I could see every detail of her little bra through the material of her costume. I was surprised to see it wasn't a training bra, but a real one! Grace was developing a bit faster than the other girls in that area, so it made sense. Instead of a camisole, she actually had two little cups encasing her boobs. She was probably no more than an "A" cup, but on her small frame, they did look proportionally bigger. The bra cups narrowed into a latch right in the middle of her chest. She had other accessories yet to put on, white tights, angel wings, her harp, and of course, a halo.

In attempt to avoid lingering too long on Grace's skimpy costume, I turned my attention over to Katherine. That was a mistake because I'm sure ended up leering just as lecherously at her. Katherine's situation was sort of an inverse of Grace. On her shoulders, she wore a rich black cape with shiny red lining and a velvet rope trim. Well, it was more of a half-cape because it didn't even reach down to her waist.

Her leotard was naturally the opposite color of Grace's, but equally thin and transparent. The black coloring made a nice contrast to her creamy, white skin. Her cape tied at the neck and made to lay down her back, but perhaps too shy to let me see her training bra, she currently held her cape wrapped tightly around her upper torso like a shawl. However, unlike Grace, she did not have the benefit of a skirt to protect her lower half or her long legs.

While grace stood confidently in her skirt, Katherine had a more reserved stance with one foot on top of the other and her knees almost touching. Her white panties showed clearly through the leotard, its fabric wrinkling the smooth shape of her hips and its stark color ruining the red and black motif Mr. Beski had been aiming for.

All three girls were statuesque in their appearance with only minor differences. Grace seemed proud of the fact that she was ahead of the other girls in her breast development. Also, she kept licking her lips which were a little fuller than the others and had a slight, natural pucker to them. When she smiled, her little, upturned nose wrinkled in an adorable manner.

Katherine was taller but also slimmer. She hadn't caught up to Lucy or Grace in the breast department yet, but she more than made up for it down below. I later learned that Katherine's grandparents had bought her a horse and she loved to go horseback riding. Apparently, that sort of exercise can really develop your bottom. Her ass was so tight, that when she stood, the two halves of her bottom separated. But it wasn't just her bottom. Her entire legs, from the thighs on down, were sculpted perfection. And she had the most noticeable thigh gap of the three, even with her knees closed tightly to the world.

Don't get me wrong, while each girl had exceptional attributes here and there, Lucy was the total package. When she spoke just then, it snapped me out of the trance I had been in.

"Mikey, we have a problem and need your opinion." She explained.

Then she stared to say, "Grace thinks that...", but then Grace huffed loudly and shot her a death stare. Grace didn't want to be thrown under the bus. So, Lucy changed the wording. "Grace, and Katherine, think that these costumes are too thin. I don't think that's the problem, but I agree something is wrong. Can you help?"

Lucy had neither the benefit of a skirt, nor a cape. So, she was just standing there in her leotard with one hand on her hip. She probably should have been a bit more scandalized to be showing me so much skin; especially in front of her two best friends. But I had already seen so much more of her that this was pretty mild. The fact that she showed no embarrassment probably worked in her favor.

"Hmm..." I appraised them with a hand on my chin, trying my best to look more like a fashion critic and less like a horny 13-year-old boy. Without a word, I twirled my finger in the air indicating that they should turn around. I only did it so I could get a good look at Katherine from behind. While I was trying to calculate how far a quarter would bounce off her ass, it did remind me of one actual problem. Her white panties were a distraction, and they did look out of place beneath her black leotard.

Lucy too had an underwear problem. She had put on mismatched pair with a white training bra and black panties in a poor attempt at color balance. It didn't look right at all and messed up the vertical half-and-half image she was striving for. In addition, her underwear bulged out weirdly in all the wrong places under the leotard.

I was ready to state my opinion. "I don't think you have anything to worry about." I assured them. "It only looks a little weird in here under the harsh lights. It will look totally fine outside at night."

Then I added, "There is one thing, Katherine." She looked at me in terror at being called out by name. "I don't know how to say this delicately, but your underwear does kind of show through, only because it's white, I think?" I pretended I couldn't really tell what color her panties were even though they were obviously white. She blushed and somehow squeezed her legs even closer together but nodded at my advice.

Then I noted, "Lucy, you have the same problem." I glanced over at Grace. She looked mortified that I was going to start discussing her underwear next. But because of her skirt, I had no idea what color her panties where. And it didn't really matter. I could have mentioned how her bra stretched out the fabric of her leotard in ways Mr. Beski probably didn't intend. But I felt that was going a bit too far.

Having said my peace, I expected to be dismissed. But the girls kicked into problem-solving mode, turned to each other, and all started talking at once. Katherine asked if she could trade panties with Lucy. That would help her situation some. But what about her training bra? It was white, too! Grace had a black bra, but it would be too big for Katherine's smaller chest. And that left poor Lucy. She had not planned this through very well, because she couldn't wear black or white underwear!

I realized they must have forgotten I was still when they began discussing intimate matters that weren't appropriate for me. So, I decided to dismiss myself. I reached the end of the hall and started back down the stairs when Lucy came running up to me from behind. She gave me another huge hug of thanks.

"Thank you, Mikey!" She said with a quiver of relief in her voice. "When they saw the costumes, they were about to back out. But I think you convinced them. I owe you one. I really didn't want these crummy costumes to make us miss trick-or-treating."

"You don't owe me one," I assured her, "you actually owe me two; one for this, and one for making me miss the haunted house. Anyway, your costumes are not crummy. They're really cool. You did a good job on the design. When you all stand together, you all just look perfect!"

She beamed at my compliment, but then her smile faded. "Katherine and Grace will look perfect. But mine is still all messed up because of my stupid underwear."

Then almost as a joke I said "Hey, maybe you don't need underwear!" That got her attention!

"I bet Mr. Beski designed these costumes to be worn without underwear. That's why they don't fit you right, either. You've been wearing them all wrong!"

She looked down at herself and I could see she was considering it. That was one brave little girl. Or reckless, who knows? Then she looked back up at me with a smirk and a gleam in her eye.

"...Dare me?"

I should have immediately said "No, way!". Without her underwear, my sister would be woefully underdressed. Trick-or-treating from house to house in a transparent costume where you're meant to be seen by all your neighbors, not to mention all the other kids out roaming around. That was not the time to attempt daring exploits. I should have convinced her to wear something else, or just go as she is. I should have said her underwear wouldn't show that badly in the dark. I...might be a bad person. Because instead of doing what I should, Mikey Jr. took control and I doubled down.

"It wouldn't be fair, Goosey." I began with a heaping of feigned regret in my voice.

When she was very little, Lucy wanted to be just like me. She used to follow me around everywhere like a baby duckling follows their mother. I started calling her "Lucy Goosey", then just "Goosey". She would get so mad and stomp her feet saying in her fiercest little girl voice "I am not a Goosey! I'm a Lucy!"

But now that she was older, I meant it as a term of endearment. Goosey was growing up, and she had her own gaggle of gorgeous girls following her everywhere she went, wanting to be just like her.

Lucy looked disappointed and confused, but then I clarified my meaning. "It wouldn't be fair to your guests if you take the dare all for yourself."

The confusion disappeared from her face and wide-eyed astonishment replaced it.

"Also, I doubt your friends would accept a dare from me directly. That's why I need your help. If you do this for me, even though you owe me two, we'll call it even. Deal?"

While I spoke, she started buzzing with excitement at the prospect of another dare. She accepted the deal immediately then stood in quiet anticipation of my next words.

"Lucy, I dare you to go trick-or-treating tonight in your costume, but without any underwear on. Furthermore, I know you have a lot of influence on your friends. They look up to you. So, I want you to use tonight to find ways to get your friends to loosen up. I dare you to convince Katherine and Grace to each let me see them naked before the end of the sleepover."

Lucy's eyes fluttered and I smiled to myself. I knew she would do everything in her power to complete that dare. And no matter how much she accomplished, I knew I was going to be the beneficiary of her efforts.

Before she left to resume getting ready, I noticed a loose gossamer thread dangling from her costume near her neck. I would have ignored it, but it was right there front and center and caught the light whenever she moved. I reached out to helpfully yank it free, but it proved more stubborn than I had anticipated. Instead of yanking the thread free, I accidentally ripped the seam in the middle of her costume open all the way down to her training bra. Oops!

I assured her the costume still looked ok and the rip just made it look like a V neck. Then I took off before I did any more damage and headed downstairs. My brain was so filled with distracting fantasies, I saw the pot pie on the counter and almost put it back in the freezer! I had to be more careful. I put it in the oven and set the timer. It would be ready in about 1 1/2 hours, but could keep warm for hours, if I remembered to turn the oven down.

I answered the door on and off for the next hour, handing out treats and trying to imagine what was going on upstairs. Was Lucy already working her influence on them? Or was she just focused on getting through the first part of the dare? No one had bolted from the house in a cloud of outrage. At least that was a good sign, right? One thing, I knew for sure. Lucy would not chicken out. Something was going to happen tonight!

I had the biggest woody in my life to that point and desperately wanted to take care of it. I hadn't done it since the day before. That was a long stretch for a 13-year-old boy. But my primary jacking spots, my bedroom and the upstairs bathroom were off limits at the moment. Even though the flood of pleasurable hormones kept coming in waves, I decided to be a man and tough it out.

After sunset, the crowds of kids started getting older. Some were my age and even a few groups looked older than me. But I felt like they were almost doing it ironically and didn't put much effort into their costumes. I only gave them a single treat each. There were a few good costumes, and some good themes. But nothing compared to what Lucy had come up with. When the traffic got more sparce, I started to get nervous that the girls would not finish getting ready in time. How long do old people stay up on Halloween before they turn their porch lights off and go to bed?

Then, finally, that musical siren call came to me. "Miiikeeey, come heeere!"

It was Lucy. I burst from my spot and rushed up the stairs, on the way adjusting my erection to be less obvious. I wiped my sweating hands on my shorts then knocked on the door. My sister answered, only opening it a crack.

"Are you ready to see?" she asked.

I nodded silently.

"Ok, close your eyes." she said.

With my eyes firmly closed, she opened the door fully and led me into the room. I had to wait while she got herself into position between her friends. Then she told me to count to three and open my eyes. I took a deep, unsteady breath. This was it.

"One...two...three."

Nipples. I think I stopped breathing. I think my heart might have stopped beating. I think time itself might have even stopped. The first thing I noticed, standing across the room, and pointing right at me, were three pairs of nipples. Six beautiful, perfect, perky nipples belonging to three of the hottest girls in existence, and they were right there for my pleasure.

Lucy must have borrowed my theory that Mr. Beski's custom design did not leave room for frumpy old bras. Somehow, she had convinced them to go without bras and just wear their leotards on top. I was so dumbstruck by the six unexpected nipples, I realized I was staring, but I didn't care. I needed more time to fully appreciate the scene and reassess the girls in light of their new exposure.

I started with Grace. Her nipples were small, but perfectly round with little pointed tips. They looked pale, but that might have been the white-tinted clear fabric encasing them. They sat atop her perky rounded breasts which were just big enough to cast a shadow beneath them; an impressive accomplishment for a 12-year-old. Even without her bra, the fabric distorted a bit around her breasts, especially when she drew in a breath. But then I remembered Mr. Beski had used Lucy as a model for Grace's costume. That's why she was stretched to the limit up there.

The leotard material molded perfectly, not only to her bare chest, but to every curve on her upper body. It was truly a magical creation. But there was even more to look at. Her hair had been put up in a sophisticated updo with white ribbons and curly blonde tendrils hanging down. That looked like Lucy's doing. She was getting really good at hair.

There was white glitter on her eyelids which caused her eyes to sparkle when she blinked, and she wore silver earrings and silver halo which also both twinkled. I couldn't tell if she was wearing any lipstick on her perfectly puckered lips. Perhaps they decided it was not appropriate for an angel to be tarted up like that. She truly did look angelic as she was and didn't need any more make-up.

She wore white tights on her legs. But to my surprise, they were thigh high stockings and did not even reach the bottom of her skirt. That left a little stripe of white cherubic thigh peeking out. She had white, flat ballet slippers on her feet.

I could see something peeking out from behind her and wanted a better look. So, I silently twirled my finger to indicate that she should give me a turn. Her costume may not have come with a fancy cape, buy Mr. Beski had not left her out. The leotards all scooped down in back. And in that spot between Grace's shoulder blades sprouted the most beautiful pair of angel wings. The wings were delicate and impossibly thin, like dragonfly wings, but with an intricate design on them. Unlike some cheap store-bought wings, these came with a special adhesive so they could be glued directly onto her bare back.

She was holding her cardboard harp in one hand. As she slowly finished her spin, I got to watch her little developing breasts once again rotate into sight. She noticed me looking at her boobies and started to lift the harp to cover her chest, but then caught herself and lowered it back to her side. Lucy must have coached her up ahead of time not to do that and that it would ruin the scene. She instead stared at a spot on the floor as a light blush formed on her cheeks. It looked way better than any make-up she could have put on.

I committed the sight to memory then moved my attention to Katherine. Lucy must have coached her up as well because she now had her cape drawn back behind her as it was meant to be worn. That gave me an unobstructed view of her little developing fruits. She was perhaps a few months behind the other girls in the breast department, but she did have a nice pair sprouting from her chest. Not quite big enough to require a proper bra yet, but they would have certainly been more than capable of filling out a training bra.

They sloped out in front of her chest with enough volume to distort the front of her black leotard. Her breast cones were capped by the cutest little pokeys. Her little engorged nipples looked darker than the other girls, almost red. But that might have been the black fabric playing tricks on me.

Her hair had similarly been put up in a sophisticated do with little red serpents woven in to hold it together and a hairband with red horns on top. She wasn't wearing a skirt, so I could see that Lucy had loaned her a pair of black panties to wear under her leotard. It didn't do too much to ruin the curve of her body. She was not wearing tights, so was bare from her thighs down to her sandals.

She had bright red lipstick on, which accentuated her nipples nicely, and was holding a toy pitchfork. I guess devils didn't have to worry about looking like tarts. She had also painted her finger and toenails black and wore a black choker around her neck.

I twirled my finger at her, and she performed a slow turn for me. Now that she was wearing heels, her legs and ass looked even more amazing. I took a mental picture of her incredibly tight behind, now encased in black panties beneath her leotard, before she completed her spin. She looked at me for approval and I nodded my head knowingly. It made her blush and smile and I got to see those adorable dimples again. Then I turned my attention to Lucy.

Lucy's costume didn't come with as many extras as the other girls. She didn't have wings or a cape, for example. No harp or pitchfork. Not even shoes. The leotard itself was meant to be the focal point. And, boy, did it draw my focus! Because, staying true to her dare, Lucy was wearing no underwear on at all.

Her swelling breasts and pale nipples stood proud on her chest; one black and one white from the fabric of the costume. I noticed the split in her center seam had widened. It now came down to her belly button leaving her breastbone and the inner edges of her breasts exposed. Not that the gap mattered much, because you could basically see the rest of her breasts just by looking through the fabric.

But the black and white seam came together at her flat tummy and continued down her body as if drawing attention to the real prize. The leotard narrowed at her hip bones, and everything converged at her protruding mound. There the leotard encased each of her plump little pussy lips in fabric, one black and one white. Cradling them but not doing a very good job of concealing them. The seam also molded to her body very closely and served to pull her pussy lips apart from each other. There nestled in the middle of her slightly spread pussy was...something. I didn't really know female anatomy at the time. I just knew it looked juicy and pink and made me want more. The seam disappeared into the gap between her legs.

I tried to swallow then realized I couldn't because my mouth was bone dry. So, I tried to lick my lips instead. Stupid me! That was an utter failure, too. I think Lucy's display had broken my mind. I gave up trying to squeeze any moisture from my uncooperative saliva glands and just twirled my finger at her.

Like I said, she wasn't wearing a skirt or a cape, so basically her entire backside was naked, except for a little section of nearly transparent fabric encasing her beautiful round bottom. Her legs were bare like Katherine's. But unlike Katherine, she was barefoot. But she had glued cotton balls around her left leg and had painted flames up the other to make it look like she had one foot in heaven and one in hell. For her head, she had made a special hairband with one horn and half a halo, split right down the middle.

"So, what do you think?" she asked once she had completed her turn.

I told her she had pulled off an epic, spectacular Halloween costume idea for the ages, and that she should be proud to have such amazing, supportive friends. At least, I opened my mouth to start to say something to that effect. But instead of words coming out, my jaw just hung open and I drooled a little bit. Talk about the absolute worst time for my stupid saliva glands to start working again!

Lucy grinned and said to her friends, "I think he likes it, girls!" which drew nervous giggles in response.

I was supposed to be directing the evening, but those three beautiful girls and their revealing costumes rendered me useless. So, Lucy took charge.

"Come on, girls, we have to hurry if we're going to get any candy. Grace, grab your camera. Mikey can take some pictures of our costumes before we leave."

At the mention of candy, the girls tittered with excitement and sprang into action. After spending so much time obsessing over their maturing bodies, I forgot how immature they could still be. I think they were actually more excited about the candy than they had been about the costumes. I, on the other hand, was more excited about the mention of a camera!

They gathered up their accessories along with one plastic pumpkin each, for candy, and hustled downstairs. I met them at the front door and Grace handed me her Polaroid camera. I had never used one before, but it seemed easy enough.

They posed together in the entryway, Katherine on the right with her hip cocked to one side and a devilish grin. Grace stood on the left and adopted a serene, angelic pose. And Lucy stood in the middle with her legs apart, her arms wrapped around each friend's shoulders, and the biggest smile on her face. I took a moment to appreciate the six adorable nipples poking up at me, then I looked through the viewfinder and said, "everyone say 'trick-or-treat'!"

They had me take three, so each girl could have one copy. When the last flash went off, the girls came running and huddled around watching for the image to appear. I was hit by an intoxicating scent and tried not to gawk at their scantily clad bodies while we waited. Like magic, about a minute later, an image of three woefully underdressed girls appeared in my hand. I took one last look at it, then reluctantly handed it over. That single photograph could have sustained my erotic fantasies for years! Lucy must have sensed my disappointment because she then made a suggestion.

"Hey, why don't we take a picture for Mikey?" she proposed. "After all, we wouldn't have made it without him!"

She then decided I should be in the picture with Grace and Katherine on either side. It didn't make any sense from a theming standpoint, but I wasn't going to argue. She positioned me in front of the door where the lighting was best then told Katherine and Grace to go stand next to me. I stood awkwardly in the middle, suddenly too shy to even look at the girls, much less touch them. Grace hugged her harp to her chest and stared at the ground again while Katherine pulled her cape around her. Apparently, the sudden shyness was spreading.

Lucy was having none of it. She cajoled the girls into a better pose and said, "Remember what we talked about?"

Reluctantly, they both corrected their costumes, effectively baring their chests for the picture. Then Lucy ordered them to put an arm around me. First Grace, then Katherine complied and I, hardly knowing how to respond, gently lifted my arms to hug their shoulders. They both seemed to relax at that, so I did too.

Then Lucy lined up the viewfinder and said, "On the count of 3, everyone, say 'girlfriend'! 1-2-3!"

Grace and Katherine both called out "girlfriend!" then erupted in a chorus of laughter after the flash went off.

I, too, had tried to say it, I really did. But the resulting picture proved otherwise. It showed my mouth agape and nowhere near the shape of the word "girlfriend". Still, the girls looked great. They were both smiling perfectly in the picture and posing for the camera like professional models. Their barely encased breasts with high beams showing were the highlight of the picture. Lucy presented it to me as reward for my contribution. I still treasure that picture to this day and often take it out whenever I feel like...reminiscing.

Katherine and Grace then went onto the porch eager to get started, but Lucy tarried.

"I don't know if I can do this, Mikey!' she said nervously. I knew she was talking about her dare. To complete it, she had to go trick-or-treating in her costume with no underwear. That alone would have been embarrassing enough, but since accepting the dare, the situation had only deteriorated. Her center seam had unraveled even further. The gap now started well below her waist and only a couple inches above her pussy. She had resorted to regularly pulling the top halves back together to keep her boobs from popping out.

"You're doing great, Goosey." I assured her. "Don't worry, you'll be done trick-or-treating before you know it and back here with a huge sack of candy."

That seemed to motivate her. I was sure to add, "But don't forget. That's just the first half of your dare."

She grinned and said with fierce determination, "Don't worry, I know I still owe you two. I haven't forgotten. And I never fail!" She gave me a hug and as she turned away to step out the door, I got to appreciate her spectacular bottom once more. That's when I noticed the rear seam at the small of her back was starting to unravel and a gap was forming. All that tugging in front must have been putting too much strain on the back. I briefly considered warning her but figured it would only make her more anxious. So, I just let her go. I doubted anybody would be looking at the small of her back when there were other much more interesting parts of her body on display.

Once the girls were gone, I checked on the pot pie. It was finished, so I switched the oven to "keep warm". Then, still on trick-or-treating duty, I returned to the living room. I stared at my new Polaroid picture of Katherine and Grace, my own personal angel and devil, who I knew for a fact thought I was cute. I still had rather strong urge to, ahem, take care of myself. But I had already decided to tough it out and wanted to see if I could make it the rest of the evening. I suspected it was somehow contributing to my feelings of euphoria and I sure didn't want to risk the feeling ending.

The girls were gone for well over an hour. I was beginning to wonder how much candy those pumpkins could possibly hold. When they finally did return, they rang our own doorbell and gave me a pretty good idea of how every house interaction must have gone.

"Trick-or-treat" they yelled when I opened the door. Their pumpkins were already overflowing with candy. I couldn't imagine being able to fit even a single additional candy corn inside. It looks like Katherine had decided to take good advantage of her cape to protect her little boobies from prying eyes. Similarly, Grace hugged her harp, the cardboard doing a pretty good job concealing her plump little treasures.

Unfortunately, poor little Lucy had no such accessories to hide behind. In fact, things had taken a terrible turn for her. She had lost the battle with her seam and her costume was now split completely in two, from top to bottom. The white and black fabric which had originally encased her growing breasts, now ran uselessly down either side of her. Her smooth stomach and abdomen were similarly exposed. Even the mound of her pussy, which had previously been encased in delicate strips of fabric was now hanging bare. Instead, the fabric bunched up on each side of her pussy lips and framed them. If anything, the fabric squeezed them together and made them even more prominent. The little extra wrinkle at the top of her cleft was also more prominent than I had ever seen and the whole thing was covered in a sheen of moisture.

I wondered how many houses she had gone to with her boobs exposed and her little pussy bulging
out like that. How many times had she been forced to meekly lift her pumpkin to receive a neighbor's treat, then treating them right back with the sight of her naked bottom as she turned and walked away? It must have been utterly humiliating having her costume gradually disintegrate around her as they traveled from house to house. But to her credit, she had completed her task and honored the dare; well, the first half, at least.

It felt like midnight but was only around 10:00. The girls were hungry but wanted to change out of their costumes before dinner. I was a bit bummed at that. I had been hoping to see more of the girls in their skimpy costumes. But Lucy was desperate to put something else on and Grace said she was sick of running into things and wanted to take her wings off. So, while I set the table, they ran upstairs to change.

Katherine was the first to emerge. Sadly, my personal devil was gone and the cute girl with regular play clothes had returned. I was disappointed to see she was wearing her training bra under her shirt. But she was still a knockout. Grace came down soon after, also wearing play clothes and a bra, and I started to wonder if the spell had been broken and the girls were done with their daring adventures. Did that mean evening excitement was over? Had I been holding out hope for nothing? I should have known better. Lucy still had half a dare to complete, and she wasn't going to fail.

Lucy emerged last and we started eating. We devoured the pot pie; no surprise as it was so late, and even an extra box of mac and cheese I had made. Then the girls started into their candy. I guess all that sugar gave them an energy boost because they then started brainstorming things to do next. Someone suggested a scary movie, but we didn't own any scary movies and had no way to get to Blockbuster. Besides, all the scary movies were surely checked out by then.

One of the neighbor ladies had been rude to them earlier. She had called the girls "harlots" and slammed the door in their faces. They wanted to go do a trick on her house. I didn't mind. The old lady sounded like a bitch. But they couldn't think of anything good to do to her. Then someone said tonight was supposed to be a party. Why not play a party game? That's when Lucy, with a gleam in her eye, dropped a bomb.

She excitedly asked, "Hey girls, have you ever played Blind Squirrel?"

[Firebomb]

Wow this Halloween story is awesome, even if slightly late. i am a big fan of the dare me stories, very masterfully written. Great new additions, can’t wait to see what happens to those girls next

[TeenFan]

Will one of the girl's go for the "Nuts" Mikey has hidden somewhere within his clothing. One of the girl's should at least make a try for it. And
there's plenty of material to make blindfolds.

[neverdoubted]

Dare Me - Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle - Part 3

Just when I thought the evening was winding down and my fun over, Lucy revved it back up. Of course, Katherine and Grace had never even heard of Blind Squirrel. That's because it was a game completely made up by one of our babysitters one night when we were younger. I'm not going to describe the whole evening again, but let's just say the game ended with one very naked little Lucy.

My heart beat faster as I watched the wheels turning in Lucy's mind. She still had half a dare to complete. And along the way, she was supposed to find ways to get Grace and Katherine to loosen up about their modesty. Considering they had just returned from trick-or-treating in transparent costumes; I'd say she was doing a pretty good job of that. But that wasn't the whole challenge. I was still holding out hope that she would figure out a way to convince each of them to let me see them naked before the end of the sleepover.

I didn't know exactly how, or even if she could do that, but Blind Squirrel was sure to factor in somehow. Lucy's genuine pre-excitement for the game was contagious, and soon Grace and Katherine were eager to find out more. She promised to explain everything but said they all should get ready for bed first and then they could play.

The two girls exchanged glances at that suggestion. Why get ready for bed if they weren’t going to bed? Why not just play the game first? But Grace had started itching the glittery places on her skin and conceded a shower wasn't a bad idea. Katherine, too, wanted to get out of her make-up and let her hair down. That settled, Lucy sent me outside to find some Seeds of Spring then left to, I guess, make sure the girls were properly prepped for the game and to get ready for bed herself.

Last time we had played, during phase 1 of Blind Squirrel, Lucy had been maneuvered out of her nightgown; forced to turn it into a sack to carry her acorns. She ended up participating in Phase 2 topless wearing only her panties. But she had been younger then and completely flat-chested. Katherine or Grace were further along in their maturation journey. If they were going to be put in a similar situation I was in for a much more titillating sight. My prick surged with excitement at the mere thought. But with some extra willpower, I suppressed my urges and stayed on my task.

A Seed of Spring was a special type of acorn necessary to play the game. It was supposed to be just like any other acorn, except pure white in color. Only I had discovered that they actually had little, microscopic grooves in them which had given me an unfair advantage last time around. It turns out Seeds of Spring were nowhere near as rare as I thought, and I found three good ones in pretty quick order.

I was leaving the particulars of the game up to Lucy this time around and didn’t know completely what she had planned. But she had specifically requested only three Seeds of Spring. Did that mean she only meant for the three girls to participate, and I wouldn’t be playing? Possibly, but I wasn't taking any chances. Just in case, I took some time to study the ones I had found. I felt around each one, carefully memorizing every crevasse. I even mixed them up with some regular acorns and practiced picking them out from among a little group until I was able to consistently pick out the Seeds of Spring with my eyes closed.

A few minutes after that, the girls joined me on the porch with Lucy in the lead. She was carrying a blindfold with her but had strangely also brought three belts. I tried think back. I knew the blindfold was for the blind squirrel to wear. I didn't remember using belts last time. Maybe she intended to make some tweaks to the rules. She had removed the tattered remains of her Halloween costume and taken a quick shower without washing her hair. She wore a white tank top that was nearly long enough to count as a nightgown. But I could still see the bottoms of her white panties poking out underneath. That wasn't the only thing poking out. It was obvious she was not wearing a bra and her nipples stood out proudly beneath her top. She was barefoot.

Katherine came behind her. She had taken a shower as well and removed her make-up. She hadn't washed her hair but had let it down so that it now framed her face. She looked younger without her sophisticated hairstyle and bright lipstick. She wore a pink pajama top with a loose, almost scoop-style neck. It came down so far on her chest that it was obvious she wasn't wearing a bra, either.

Her pajama top flared out at the bottom and swished around her waist as she walked. Lucy must have instituted a "no pants" rule for this game. Because she wasn’t wearing the matching pajama pants that would have made it into a set. I couldn’t see her panties at first, but as soon as she turned away from me, I seized the opportunity to sneak a peek. I saw she had picked out pink panties with cute little ruffles on them that also swished when she walked.

I didn’t look away fast enough and she caught me staring at her cute little panty-clad bottom. As much as I had already seen of her body, she still had moments of bashfulness around me. She pulled her shirt down and stood like she had done upstairs with one foot on top of the other and her thighs squeezed at tightly as she could manage. It was adorable.

Grace won the prize for the most shocking pajama reveal of the night, though. Because she came through the door wearing one of my shirts! Lucy explained that Grace had only brought a fancy nighty to wear to the sleepover and didn't want to get it dirty playing outside. So, Lucy had generously volunteered provided my only dress shirt for her to wear instead. If you've ever seen a woman in a man's dress shirt, you can imagine what Grace looked like.

It was white, an appropriate color for an angel, and hung down just past her waist on the sides but went lower in the front and back. She wore no pants and her curvaceous legs stuck out beneath in a way that drove me wild. I would never be able to look at that shirt again without getting a boner. Up top, she had rolled up the sleeves and left most of the center buttons undone. The shirt sloped out over her more developed bust. The way her boobies flexed beneath the fabric made it apparent she wasn’t wearing her bra either. I couldn't see her panties at all; at least not at first, but she was barefoot like the other girls.

She had taken her shower to remove the glitter makeup. But she had additionally washed and dried her blonde hair which now fell straight to her shoulders. She saw me studying her every move and asked Lucy if she could borrow the hair tie around her wrist. On the surface, it was an innocent request. But when she moved to make a ponytail, my eyes nearly popped out of my head. The shirt, with most of its buttons undone, spread open as she raised her arms until there was a huge gap revealing almost all of her squeaky-clean chest. From a better angle, I would have been able to see directly in and gotten a complete view of one of her hanging mammaries. But since she was facing me directly, I could only see the space between them.

I stared agape at the inner bulge of Grace's little developing breasts silently begging the shirt to open just a little further and reveal her nipples. She fiddled innocently with her hair to make sure it was just right, perhaps taking a little longer than necessary. That's when I realized my little angel had been waiting for me to notice something else. I looked down her body and this time my eyes actually did pop out and my soul left my body. By keeping her arms above her head, Grace was giving me a peek at her panties.

I hadn't had the opportunity to appreciate Grace's bottom half thus far in the evening because her costume had come with a skirt. The girls both seemed to pay close attention to wherever my attention drifted. I sensed a competition forming. Maybe she had grown jealous of the looks I kept giving Katherine's ass and wanted to show me that she had plenty to offer in that department as well. Facing right at me, it was almost like she wanted me to notice that she, too, had a perfect little thigh gap between her legs.

Her hips, which had been concealed all evening beneath a cloud, did have more curve to them than I expected. I couldn't see much of her bottom, but it looked both ripe and firm. I later learned that came from years of gymnastics and ballet and that she was looking forward to trying out for the junior high cheerleading team next year. She was a shoe-in.

But the piece de resistance were her panties. Grace was wearing the tiniest pair of panties I had ever seen. They were sky blue with white lace trim and matched her eyes perfectly. A tiny stripe of material encircled her waist. And in front, a narrow blue triangle came down to embrace the mound around her pussy. The material was too thin to provide any support and simply followed the contours of her plump little pussy lips before disappearing into her thigh gap. If this was a matching part of her evening attire, I desperately wanted to see what the rest of her nighty looked like! Having accomplished her mission, she finished her hair and dropped her arms back down. The show was over...for now, but the competition was just beginning.

Lucy started describing the game's lore with the voice of a mysterious storyteller and explaining the rules of phase 1. As anticipated, and to my disappointment, she said I would not get to participate in the competition. My role would be to follow the girls around, keep time, and make sure everyone was following the rules; resolving any disputes that may arise. I was sent inside to retrieve the kitchen timer and when I got back, I saw she had instructed the girls to tie the belt around them. My suspicion was correct. She had added her own twist to the game. The belts were not tied around their waist, though. They sat much higher, on the girls' rib cages just beneath their chests.

I figured it out. Rather than make the girls fashion sacks from their clothing like we had done last time, Lucy was going to have them collect the acorns in their clothes while they were still wearing them. My hopes of seeing the girls running around topless gathering acorns were dashed. But my disappointment was short-lived when Katherine asked something, and Lucy's answer made everything better.

"What are we playing for again?" she asked. "I mean, what do I get when I win? Wait...how do you even win this game?"

Lucy smiled, then with a quick glance over at me, she pulled out the three special acorns and revealed the rest of the game.

"When phase 1 is over, each of you gets to divide your acorns however you want between your opponents. Then we will add one of these Seeds of Spring to each sack. Mikey is going to be the blind squirrel. He'll take turns picking acorns out of our sacks. As soon as he finds a Seed of Spring, that person is the winner. So, the more acorns you can add to your opponents' sacks, the better your chances will be."

"But what is the prize for winning?" Katherine asked.

"The winner can relax and gets to sleep in tomorrow. The loser has to get up early and bring Mikey breakfast in bed in their Halloween costume. Only, the winner gets to pick how much of it they get to wear!"

Grace blushed and Katherine's mouth dropped open for a moment. Lucy watched the reality sink into my face with a mischievous grin. The last time someone had served me breakfast in bed, it had been Lucy, and she had been completely naked. Could she possibly convince Katherine or Grace to do something like that?

My face burned with embarrassment as I pondered the possibilities but fortunately the girls didn't notice because they were looking at each other. Perhaps they were checking to see if the other one was going to chicken out. Then Katherine, the little devil, stuck her tongue out at Grace. Grace's eyes narrowed and I could tell from the look in her eyes that she wasn't going to back down. She was going to win and would savor sending Katherine into the lion's den.

I'm not sure if Lucy guessed I had figured out a foolproof method for picking the correct acorn every time. She had accused me of cheating last time we played this game. Perhaps she suspected I had a way of manipulating the game to make whomever I wanted the winner. If so, surely, I would work it out so Lucy won and Grace or Katherine lost. Or maybe she was just willing to take her chances. After all, she knew where to get a huge pile of acorns. Maybe she was just counting on that to carry her to victory.

I didn't really care. I had already decided I was going to let Lucy win. The real decision was between Grace or Katherine. The angel or the devil. Who did I want serving me breakfast in bed tomorrow?

But as I was pondering that dilemma, Grace made a critical observation. "Wait a minute. Won't there be two losers? How come second place gets to sleep in, too. That's not fair."

"Good point," Lucy replied, "in that case, both losers have to get up and help make breakfast. Then one can deliver the food to Mikey and the other will pick it up. The winner picks the costume for second place, and second place picks for third."

That really raised the stakes sky-high. Instead of a 33% chance of losing and being sent to my room in whatever the winner wanted them to wear (or not wear), the girls now had a 66% chance of losing. The girls clearly didn't like that new rule, but I was loving it. Now I didn't have to choose. I only had to make sure Lucy won and the rest would take care of itself!

[clockspinning]

Let me guess. Three-way tie.

[perseus]

Fantastic story! This was the one I voted for so I'm glad all those ballots showed up last minute

Do you plan on doing "the list swimsuit" also?

[neverdoubted]

Fantastic story! This was the one I voted for so I'm glad all those ballots showed up last minute

Do you plan on doing "the list swimsuit" also?

Yes, this story has 7 parts total. The original story will continue after that.

[perseus]

Fantastic story! This was the one I voted for so I'm glad all those ballots showed up last minute

Do you plan on doing "the list swimsuit" also?

Yes, this story has 7 parts total. The original story will continue after that.

Awesome! Can't wait to read the rest of this story! And very much looking forward to the next chapter of the mainline Dare story!

[neverdoubted]

Dare Me - Halloween Sleepover Spectacular - Goosey's Gorgeous Gaggle - Part 4

It was nearing midnight when the girls set out to collect their acorns. The trick-or-treaters were long gone, and We had the night to ourselves. Porch lights were all off and the moon added only a sliver of light; not much help to the three cute bare-legged squirrels desperately scavenging through the grass for acorns. Whenever someone found one, she would squeal with delight and drop it into her shirt for safe keeping. The belts cinched tightly just below their chests kept the acorns from falling out the bottom.

Despite some success, the pickings were slim. I saw Lucy surreptitiously distancing herself from the group and guessed she was following my playbook from last time. She wanted to make for the grove of old oak trees behind our neighborhood where the acorn could be found in real quantities. But the other girls, perhaps suspecting she was up to something, stayed close to her and prevented her from sneaking off.

Eventually, she gave up sneaking and suggested they all head to the grove together. I agreed but called a timeout to go get a flashlight. As their escort, it was my duty to keep them safe. Then the three girls set out down the sidewalk with me a few feet behind.

Trailing behind them, I had the opportunity to really study the way they walked. Katherine looked to be wrestling with the fact that she wasn't wearing pants. She started out with her arms straight holding down the hem of her top on each side. I could still see all the way to the tops of her legs, but her bottom was covered.

Her long legs carried her with confident strides. But it was an awkward way to walk because it didn't allow her to swing her arms. So, whenever she started to fall behind the other girls, she would give up and walk normally for a little while. Whenever she did that, I got to watch the ruffly hem of her top slowly creep up until the lower half of her muscular bottom was once again hanging out.

She had a little crease at the tops of her legs right where they met her bottom which would disappear on alternating strides. And her bottom curved out from there like a shelf. Her pink panties were pulled tight across her butt cheeks. Her bottom was so tight it didn't jiggle much when she walked. But the little ruffles across the seat made up for it, swishing adorably with every step.

Grace, with the benefit of shirt tails walked more freely. In fact, she pranced around like a young burgeoning cheerleader hopped up on Halloween candy. I tried to direct my flashlight around in a random pattern as if revealing the terrain ahead of the girls. But I think Katherine caught me shining it right at her backside because she would modestly pull her shirt down with a shy glance in my direction. I also frequently pointed it at Grace's backside in the hope of catching a particularly perky bounce. More than once, I was rewarded by a flash of her entire ripe bottom with its smooth creamy skin clad only in the tiniest pale blue triangle.

Lucy's backside got turns under the flashlight, too. Her tank top had been sinched up by the belt so that it no longer covered her bottom at all. But she wasn't fighting it like Katherine. She just let her panties hang out. It made a beautiful sight, but I must admit the novelty of seeing her two young friends flashing me their panties attracted most of my attention.

We made it to the grove where the girls had much better luck finding acorns. Pretty soon they all three had comical bulges in their shirts like they were playing dress-up and stuffing socks up top. They kept coming up to each other trying to compare and see who had the biggest chest. From the fits of laughter, I could tell they were genuinely having fun, but there was also an ominous undertone to the game. To lose focus could mean disaster for them. More than once I caught Lucy eyeing the storm drain. There was a huge cache of acorns down there, but she had to be smart about making her move to avoid giving it away.

I watched the timer dwindle and when I called out that there were 2 minutes remaining, Lucy was ready to act. But first she had to make a diversion. She started running in a feigned panic and "accidentally" let her belt come untied. She cried out in dismay as the acorns poured out from beneath her shirt, scattering across the ground and bouncing away from her in every direction. Grace and Katherine came running at the commotion.

"Don't touch those!" She warned when Grace went to pick up some of the dropped acorns. "Mikeeeey, my belt came untied! Please, I need a timeout. You have to pause the game so I can pick my acorns back up."

"That's not fair!" Grace shot back. "Any acorn on the ground should be free for anyone to pick up."

"Sorry, Goosey" I handed down my ruling, "squirrels don't get to call timeouts. It's survival of the fittest. And you better hurry if you're going to survive the winter. 1 minute left!"

Grace and Katherine excitedly jumped into action, ruthlessly scavenging over Lucy's lost haul. Those girls were out for blood! Lucy muttered "bitch" under her breath and stomped off as if to go pout by herself. But actually, she was headed right toward the storm drain where tons of acorns always collected in the grate. The other girls ignored her completely and let her go, and while they were greedily picking through her leftovers, Lucy was loading up. They were shocked when I called "time's up" and Lucy returned with a bigger haul than either of them. She looked like she had gotten breast implants.

We returned to our porch to prepare for phase 2. Each girl unloaded her haul into a pile. Grace and Katherine's were about the same size with Lucy's being a fair bit bigger. They clearly suspected some sort of foul play from Lucy and couldn't figure out how she had managed such a big haul in only 1 minute. Had this been a two-player game like last time, Lucy would be positioned well to win easily. But she had woefully miscalculated the dynamics of a three-player version of the game.

It was time for each girl to divide her pile and decide how much to give to each opponent. Lucy diplomatically divided her pile evenly between Grace and Katherine, scooping them up and pouring them back into their shirts. But Katherine, that scheming devil took her entire haul and poured it into Lucy's shirt. Grace followed suit and did the exact same thing.

"That's for calling me a 'bitch'." she said with an air of satisfaction.

Poor Lucy thought she had played smartly. But the entire thing backfired in her face. Her chances of winning seemed next to impossible with that many acorns to sift through. Lucky for her, she had a secret weapon on her side; a horny, and extraordinarily talented blind squirrel. One white acorn was added to each shirt and the girls were instructed to jump around until it was completely mixed in. I thoroughly enjoyed the sight of them giddily bouncing around me for a minute. They were so excited about the next phase; I think they completely forgot they were all flashing me their panties.

We had a small park bench on our porch. Lucy had me sit down and fastened the blindfold on me. As the world disappeared, a sudden realization struck me. As the blind squirrel, I was responsible for pulling acorns out of the girls' sacks. Only, they didn't have sacks. The acorns were inside their shirts! Lucy had set it up so that I was going to be reaching inside the girls' tops over and over until I found the right seed.

Suddenly my hands started sweating and my heart started pounding. It was decided that the girls would roll a die to determine the pick order each round to make things fair and random. As soon as a seed was found that person would be the winner. But the other two had to keep going to see who got second.

As my erection grew to full staff, I wished I had taken time to adjust my prick before sitting down. I couldn't tell for sure in my blindfold, but it felt like it was sticking straight out and tenting my shorts obscenely. And worse, it was kind of throbbing up and down with my heartbeat.

I think the first girl noticed, because when she knelt between my legs, she let out a little gasp followed by a suppressed giggle. I recognized Katherine's giggle which meant she had been selected to go first. But the other girls quickly shushed her. The order of play was supposed to be anonymous. Any future sounds could give the blind squirrel a clue who was next. Although, knowing the girl would in no way taint the integrity of the game, as far as they knew. I think it just gave them some comfort, with a boy about to start rummaging around inside their shirts, if they could remain anonymous to him.

Katherine had been instructed to lean forward and hold her shirt open for me. I could only imagine what a sight she was making. Seriously! With a blindfold on, I couldn't see it. I could only imagine. Anyway, I cautiously reached my hand out in front of me, unsure of how far away she was kneeling. Then suddenly my hand reached her. I had aimed too high and was touching her cheek. Slowly, I traced my hand down the side of her face and onto her neck. As I passed her collarbone, she sucked in her breath with a little gasp and held it.

I paused. I was in unfamiliar territory. I had never come this close to touching a girl anywhere private before, unless you count snuggling with Lucy on the couch ages ago. That had been fun, but this felt serious. Katherine was wearing a scoop neck shirt and was supposed to be holding it open for me. So, wherever I moved, I was likely to encounter more skin and flesh before I reached any acorns. Should I move left or right first? I was just inches from her beautiful breast cones and cute little nipples. She was practically offering her breasts up to be fondled, but I was too shy to go for it. Instead, I continued moving my hand down. My fingers traced down Katherine's breastbone and I could feel her own heart pounding in her chest.

Just then I grazed an acorn, and my fingers automatically grasped it. I had pulled it out before I knew what was happening. Of course, I wanted, to draw this game out to explore these girls' bodies as long as possible. Had I accidentally picked the Seed of Spring on my first attempt, Katherine would have won the game right there. I warned myself to be more careful in the future. But luckily this was a regular old acorn, and Katherine's part of the round was over.

The next girl positioned herself between my legs and held open her shirt. This time I aimed a little lower when I reached out. See? I can learn! The first thing I came in contact with was hair. A little strand brushed against the back of my hand. Immediately, I guessed I was dealing with Lucy because Grace had put her hair up in a ponytail and it wouldn't be hanging down in front of her like that. I took note, thinking I might be able to use that information in the future, and proceeded downward to grab an acorn. This time, I made extra sure there were no grooves before pulling it out.

The third girl got into position, and I reached out a little too fast. Also, I had forgotten that Grace was a little shorter than the other two. So, my fingers bumped right into her little puckered lips. Grace opened her mouth in surprise and my fingers slipped in between them for a second. The other girls couldn't help but giggle at that. But then, remembering the stakes, they went quiet again. This was serious business. I extracted my fingers from between Grace's lips and traced down her face noticing the differences. Going forward, it cheered me to see it was actually going to be pretty easy to tell each girl apart. Their features were distinct in ways my fingers were really good at picking up. I made sure Grace, too, produced a dud on her first round and it was time to roll the dice again.

This cycle repeated, round after round, with a random order each time. I was proud of the fact that I could soon tell with a simple brush of my fingers against a cheek or collarbone which girl was kneeling in front of me. After a few rounds, I grew bolder. Instead of just plucking the first acorn I came across on top, I started burrowing my hand deeper into the pile. I would carefully pick one out from the middle then dramatically pull it out with a flourish. I like to think the girls appreciated my pageantry. I'm sure anything to distract them from their impending likely defeat was welcome.

As the rounds continued, I could feel the piles dwindling. Even poor Lucy's mountainous treasure chest (see what I did there?) was starting to shrink. But she still had so far to go! That reminded me, I had to start thinking about my endgame. How was I going to make sure Lucy won? Could I really locate that one special acorn among so many? As I was pondering my conundrum, Katherine made an outburst.

"Hey, Grace is cheating!" she accused.

"I am not. I didn't do anything wrong." Grace replied.

"Yes! I saw you move your Seed of Spring to the top your pile just now."

"Well, it was all the way at the bottom. I was just moving it to the middle."

I really wanted to pull off my blindfold to see what was going on. It would have given me a better idea how many acorns each girl had left. But to maintain the integrity of the game I resisted the urge. I did interject, however, by ordering that no girl was allowed to move her acorns around. Instead, I said I, as a neutral party, would stir their piles every round before picking to make sure nothing was getting stuck at the bottom. I'd like you to think my new rule was purely altruistic and made in the interest of fairness. So please pretend that any ancillary benefit to me that followed was purely accidental.

As much fun as I was having, I sensed it was time to pick a winner and wrap up this game. I decided I was going to end it on the next round when Lucy came up. The new stir rule went into effect starting that round and Lucy happened to be up first. I plunged my hand into her still substantial stash and began stirring it around. If you've ever stirred acorns in a girl's blouse before, you probably already know what happened next. The palm of my hand incidentally brushed the outside curve of one of her boobs. As if on instinct, my hand moved that direction and formed into a cup. And in a flash, I found myself cradling Lucy's little boob in my hand.

I'm not sure I can accurately describe it. It was pliable and by far the softest thing ever. Lucy cleared her throat impatiently and I immediately let go. A blush formed on my cheeks and head was swimming. I had just felt up a girl for the first time. I wanted more! Fortunate for me, there were literally two other girls already lined up to go next! No way could I let the game end now! So, I abandoned my plan to locate the Seed of Spring within Lucy's shirt and eagerly pulled out a regular acorn instead so the next girl could step in line.

The next girl knelt between my legs and held her shirt open for me like she had already done so many times before; oblivious to what was about to happen. I nervously lowered my hand in and started stirring. It was Katherine. She gasped when the back of my hand cautiously grazed her boob for the first time. I let my hand linger for just a second, then politely moved away to pick an acorn.

Grace went last that round. She, too, gasped when the back of my hand brushed against her boob. The other girls, knowing what was about to happen, couldn't hold in their giggles. Now that I had officially touched three girls' boobies, I felt like I could die in peace. I didn't want to push my luck and risk being labeled a pervert. So, with some willpower, and before things got out of hand or Mikey Jr. started calling the shots, I resolved to end the game on the next round, no matter what.

The girls rolled for the next round and Katherine came up first. Everyone was silent as I stirred her acorns. Then, just before picking one, I dared to make contact with her little chest one last time. This time, I led with the front of my hand, making a larger than usual circle around the outside of the pile under the auspices of getting a really good stir in. Along the way, my fingers brushed all the way across the front of her chest, following the sloping contour of her cones. This time, her nipples were rock hard from all the stimulation and excitement. She sucked in her breath as those little pebbles gave way beneath my moving fingers. But her brief excitement quickly turned to disappointment as I pulled out a regular acorn.

Grace was next. I repeated the process with her. Only, my hand had further to travel across her more developed mounds. Her nipples felt a little smaller but were also rock hard and she couldn't help but gasp when my fingers grazed each one. Alas, her hopes were similarly dashed when I pulled a regular acorn from her shirt as well.

I would have enjoyed exploring Lucy's chest next like I had the other girls. Unfortunately, I had an important job to do. So, I went right to work feeling around for the correct acorn. I started to think there were just too many to sort through and maybe I had messed things up again. But then I felt it. The Seed of Spring! I tucked it into my palm, but before I withdrew my hand, I just couldn’t resist the urge to do something I had been wanting to try for a long time. I found one of Lucy's stiff little nipples and gave it a good pinch. She tensed up, jerking back a bit, probably from the pain, but didn't audibly react.

If she was mad at me for that, I think all was forgiven as I pulled out the white acorn to astonished gasps and one thrilling scream. Against all odds, and to the other girls' great dismay, Lucy had won! After that brief outburst of excitement, it was kind of downhill from there. It was well after 1:00am and I actually started to hear yawning. As much fun as I had been having blindly getting to know the girls' bosoms, the late hour was catching up to me, too. And my thoughts started to turn to what would happen in the morning.

It didn't really matter to me who was second and who was third. If everything went according to plan, they would both be sent to my room tomorrow wearing next to nothing. So, I let a couple rounds pass just to avoid any suspicion of foul play, then I let the dice decide. Whoever came up next would be second. Grace won the honors of second spot. She would be deciding on Katherine's attire, while Lucy would decide for her.

The sugar rush long since spent and the excitement now over, everyone trudged heavily inside and headed for bed. I was exhausted, but I took the time to straighten up my room, making sure it was presentable for morning guests. I even made my bed. Then I brushed my teeth and changed into my own pajamas to sleep. By this point, I had gone over 24 hours without masturbating. That must have been some kind of record for me at that age. But somehow, I was able to resist the urge in my loins. I wanted to see just how far I could push myself and kind of felt good.

At first, I tossed and turned fitfully and couldn't get comfortable. It was so hot in my room that I took off my shirt. My pants soon followed, and I decided to just sleep in my boxers. But I was still too hot and bothered. Finally, I cracked the window to let in some cool air and was able to relax. Overwhelmed by fatigue, sleep came quickly after that. I dreamt I was a farmer with an orchard full of all kinds of fruit trees. I spend my days picking the ripest fruits, from sugarplums to oranges, lemons to peaches. And every fruit I sampled had the absolute sweetest nectar!

It was a wonderful dream that ended too soon with a jarring sound of knocking at my bedroom door.