Dare Me – Book 2
Halloween Sleepover Spectacular
Goosey’s Gorgeous Gaggle
Chapter Three
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 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 each 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!

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