Dare Me – Book 2
Halloween Sleepover Spectacular
Goosey’s Gorgeous Gaggle
Chapter Four
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 cinched 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’s not that she didn’t make a beautiful sight, but I must admit the novelty of seeing two other girls 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 while they jumped.
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.

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