Dare Me – Book 2

Halloween Sleepover Spectacular

Goosey’s Gorgeous Gaggle

Chapter Seven

I WISH I could say there was no fallout from Lucy’s Halloween sleepover spectacular and we all lived happily ever after. Unfortunately, this is the real world. So I have to tell you what happened next.

When I woke up, my stomach was grumbling and I remembered that playing with the girls had caused me to skip breakfast. It was almost noon. So I got dressed and cautiously ventured downstairs to find food but encountered Lucy instead. Part of me was relieved to hear the girls had already gone home. I wasn’t sure how I would be able to face them after what we had done earlier in my room; especially since I had agreed to be both of their boyfriend. Love triangles never work out, after all. But part of me was also disappointed that they were gone. Mikey Jr. certainly missed them.

Lucy was all smiles and seemed grateful for the fun night with her friends. She said the girls had had a fun time, too. She had a twinkle in her eye when she said it, but didn’t elaborate. She was exhausted and said she was going to go take a nap. She handed me an envelope then, in a flash, reached up an gave my nipple painful pinch.

“This is for last night!” she yelled then fled up to her room and locked the door before I could retaliate. I resolved to make her pay for that, but when I saw the envelope I decided to forgive her. On the outside she had handwritten “Here’s the two I owe you.” On the inside were two Polaroids; one of my Katherine standing naked in her devilish pose, and one of my naked angel Grace looking as innocent and chaste as ever.

I thought I was the luckiest boy in history and treasured those pictures as mementos right along with the other one they had given me last night. Everything seemed to have worked out perfectly. But then mom got home and it all started to fall apart. She looked horrible and went straight to bed, having clearly had a rough night. Apparently, her boss had subjected her to all kinds of humiliations on their “business trip”. Later that evening I overheard her recount every embarrassing detail over the phone to Aunt Julie, her sister.

Mom’s boss had been planning a night of poker with his buddies, or “clients” and decided at the last minute to make it into a Halloween party. There was a big convention center in Westfield about an hour away which was already hosting several bigger Halloween parties that evening. But he was going for something a little more intimate. So, he found a cheaper hotel nearby that wasn’t affiliated with the convention center and rented out their conference room for the night. He didn’t even really rent it. He just paid off the manager, who was also working the front desk, in cash to make sure they weren’t disturbed.

He got some cheap decorations and started calling around for a last minute DJ. He found one already who had another gig, but agreed to rent out his dance party lighting kit which he wasn’t using that evening, for a small fee. The room was already wired for sound, so the DJ helped with that, too while he was there setting up the lighting. Of course, mom’s boss didn’t tell mom about any of this. When she arrived, she was completely caught off guard.

She asked to go up to her room to at least freshen up, but instead of giving her a room key, her boss went with her. He berated her the entire ride up the elevator about how unprepared she always was and that she was making them so late by not being ready. When they got to the room, he went in with her. She was shocked to see it was one of those Jacuzzi suites with the bathtub right there in the open. He said, unless she started pulling her weight, he wasn’t going to pay for a separate room for her anymore on business trips. Then he told her to hurry up and get her costume on.

Mom said she didn’t have a costume because he hadn’t told her it was going to be a Halloween party. That made her boss even angrier. He accused her of not putting forth any effort and said he really expected her to make a good impression tonight with the clients, hinting that her job might be on the line. He ordered her to take a bath and make herself presentable while he would try to find a Halloween store that was still open.

Mom did what she was told and took a bath in the Jacuzzi. Only after she got out, did she notice her boss had taken her suitcase with him. Since she didn’t want to put her dirty travel clothes back on, she was sitting on the bed wrapped in a towel when he returned in a huff.

He had found a kinky shop nearby and had picked out a slutty nurse costume for her. He hadn’t brought her suitcase back up with him. When she asked for privacy to try it on, he roared at her in anger. He insisted that she had wasted too much of his time to be making demands like that. They would both have to get ready in the room together and there was no longer any room for modesty between them.

Mom was a pushover. She was a quite attractive woman in her early 30’s and probably got the same reaction every time a man saw her naked. But her boss just scowled when she let her towel fall to the ground. This time he was pissed that she hadn’t shaved her bush. He insisted she fill the Jacuzzi again and shave herself bald while he finished getting himself ready.

He didn’t even hand her a towel afterward, but just made her stand there dripping while he inspected her work. Then he threw the costume at her and told her to be in the conference room in 10 minutes, or else. There were several problems with the costume. Most importantly, it came with a strapless bustier which was supposed to be worn beneath a scandalously small jacket. She could get it zipped around her stomach, no problem. But the average sized bra cups were no match for her much larger breasts. She simply had too much up top and had to leave the bustier behind.

The panties were white silk and very skimpy with a huge cross cutout in the back, like a medical cross. And the skirt was little more than a notion. A pair of spike heels and garter belt with stockings came next. The heels made her butt stick out even more. The rest of her costume consisted of a hat with a red cross in the middle, a stethoscope, and white gloves that came up to her elbows.

She wore the jacket, which had no buttons. But without the bustier, it was her only option. Her nipples were barely covered, but the entire middle of her massive cleavage was exposed right down the middle to her slim stomach.

Her time was almost up, so she rushed to the elevator and headed to the basement where the client party had already begun. Only by holding the jacket stead with both her hands could she possibly hope to keep from flashing everything. A chorus of cheers met her when she entered. There were at least 20 people there, all men. Her boss led her around forcing her to vigorously shake hands with, and briefly flash at least one nipple to every client in the room. Then it was decided that, since she didn’t know how to play poker, she would be the bartender and serve them drinks while they played.

She spent an hour mixing and serving various drinks and hors d’oeuvres. When dirty dishes started to pile up, she had to carry them up to the kitchen, with her jacket hanging wide open, and wash them herself under the watchful gaze of the hotel manager.

Later in the evening, her boss was doing poorly. His chip stack had dwindled, but he insisted he was letting the clients win. It was just good for business, you see. He got eliminated but asked if he could buy back in. The table said “no” because he didn’t have anything of value left to bet. That’s when he suggested mom’s jacket. The poker table agreed that would be worth another buy in. Mom balked, but he insisted. After all, it wasn’t her jacket. He had paid for it (with the company credit card).

He promised that, after he won a few hands, he would have enough to buy it back for her. So she reluctantly stripped it off and handed it over. Of course, that was the end of her jacket for the rest of the evening. She ended up serving drinks topless all night. But it didn’t end there. Her boss soon found himself out of chips again and offered some more of her costume as collateral.

By the end of the night, mom was serving drinks in nothing but her hat, gloves, and shoes. And every time she went up to wash more dishes, the night manager got to see what else she had managed to lose at the poker game. Mom didn’t say specifically what happened after that. Only that the after party involved the Jacuzzi in her room.

Aunt Julie was furious and called him a “slimeball pig” and said mom should sue. I knew she had mom’s best interest at heart, but Aunt Julie was a twice-divorced feminist who called every man a “slimeball pig”. So, it didn’t exactly spur mom to action. Aunt Julie said she should start keeping evidence of his wrongdoing. Get some dirt on him. Mom didn’t like confrontation, though. And the idea of suing was too much for her. But she did promised to start gathering evidence of his wrongdoings. And several months later she did manage to nail that scumbag.

It wasn’t until the next day that things really started to fall apart. Apparently, Grace had let it slip that mom hadn’t been there to watch the girls at the sleepover and had instead left a 13-year-old boy in charge. When I got home from school, I learned that both the other moms were coming over to “talk” with our mom and they wanted me there, too. Uh oh!

I went to my room to put on my best clothes and figure out what I was going to say to convince them. While I was putting on my dress shirt, I was momentarily distracted by the image of Grace wearing my shirt and flouncing around in her blue panties. I got a boner, but pushed the thought out of my mind. If I got aroused in front of Grace or Kathrine’s mom, they might cut if off! If Grace or Katherine had cracked and told them everything that happened, their moms might cut it off anyway.

That evening, we sat around the table, just me and the three moms. I couldn’t help but notice where Grace and Katherine got their beauty from. They were like scaled up versions of their daughters and shared so may of the same mannerisms. Katherine’s mom had just come from work and had entered wearing a skirt suit. She smiled at me in a cordial greeting and I saw she had the exact same dimples as her daughter. Too bad that was the last time she smiled at me the entire meeting. I took one look at her lips and blushed when I realized that I knew the exactly what color her nipples were.

When she walked around the table, her spectacular butt flexed beneath her long pencil skirt. She took off her suit jacket before she sat down. Her blouse had the top couple buttons undone and I was treated to a peek of her unexpectedly large cleavage. I tried not to look, or at least not get caught looking, and pay attention to her speech, but I just couldn’t stop imagining what it would be like to pour a ton of acorns into her blouse and go for a stir.

Grace’s mom had the exact same pale blue eyes, strawberry blonde hair and upturned nose as her daughter. She must have been on her way to or from the gym because she was wearing a velour lounge suit. She didn’t take her jacket off, but it was unzipped showing off the biggest chest of the three women. I couldn’t help but imagine her straddling me naked while I held onto those massive mammaries and she flapped her wings for me. So much for not getting a boner in front of them, eh? The only thing that saved me was being able to hide it beneath the table.

They wanted to know what happened that night, in my words. I took that request as a good sign, because it meant the girls had probably not totally cracked. I tried to use my most mature voice as I spoke. I said mom got called away at the last second for an important, mandatory business trip and Lucy would have been devastated to cancel. So I agreed to step in even though I had other plans. The girls went trick-or-treating and came back to eat a hearty and healthy dinner that mom had prepared. Then we had played a game called “Blind Squirrel”, a silly game that a babysitter once taught Lucy and I. After that, they all went to bed. I stayed up and handed out treats until about 11:00 then went to bed myself.

The two moms listened intently to my story, seeking to detect any irregularity or deception. I had had to fabricate some of it, but stuck enough to the basics that it hopefully matched whatever their own daughters had told them. I made it intentionally generic, like a million other Halloween stories all over the country. But then the question of costumes came up. Apparently, a rumor was floating around the neighborhood gossip chain that some girls had been going around in extremely skimpy costumes; like, practically naked. Grace’s mom particularly wanted to make sure they weren’t talking about “my little Gracie”.

My mom was at a loss, because she hadn’t actually seen the costumes at all. The girls had both sworn it wasn’t them and, luckily, Lucy had already thrown the costumes away. That the trash truck happened to be running that day was the only thing that saved us. I played dumb and pretended I wasn’t really involved in that area. I explained that, while they were getting ready and leaving, I had been distracted making sure the pot pie, which is a healthy, wholesome dinner for hungry tweens, would be ready when they got back. I think I looked convincing when I tried, and failed, to remember what they had even gone as.

I did mention that Mr. Beski, a trusted adult, had made their costumes. He was a professional tailor and was just across the street if they wanted to talk to him. There were always stories like that floating around at school at Halloween, I told them, but everyone knew they were made up. I assured them there was no way that rumor could have anything to do with their girls and that I felt everyone had had a wholesome, good time. I think I said “wholesome” at least 9 times in total. I also, smartly, avoided any mention of a camera.

I think my story pretty much tracked with what the moms had already heard, but they were still very upset at our mom for leaving us kids alone. So I went on, explaining how hard it was for a single mother to provide for us – her poor, wholesome children. She was doing the best she could. Katherine’s mom seemed to soften at that. It tugged at her heartstrings.

But Grace’s mom was still on the warpath. She said she simply couldn’t risk something bad happening to her little angel (if only she knew, hehe) and was going to forbid Grace from being friends with Lucy. Katherine’s mom didn’t go that far, but said Katherine would no longer be allowed to come over to our house to play.

Lucy would be crushed by the news. But she was resilient and would recover eventually. To be honest, I was a little bummed too. With no apparent way to spend time with Katherine or Grace, I had effectively, in the span of 48 hours, gained and lost my first two girlfriends. Sadly, it would be several years before I managed to even get a third. But I will never forget that one spectacular Halloween…THE END

Thanks for reading! The story continues with Dare Me – Book 3
~ND

Other books by NeverDoubted

Dare Me Series

  1. Book 1 Compendium
  2. Halloween Sleepover Spectacular – Goosey’s Gorgeous Gaggle
  3. Book 3 Compendium
  4. The Lost Swimsuit Saga
  5. My Nightmare
  6. Hardship Study Buddy
  7. Mikey Gets a Dare
  8. Doctor’s Orders
  9. Wait, What Happened at Camp?
    …to be continued

Thornwood Series (Bystander Universe)

  1. The Tryout
  2. School Pride
  3. In Training
  4. The Champion

Caroline is Confused Series

  1. First day Jitters
  2. Creature of Habit
  3. Sins of the Mother
    …to be continued

Read these and more at neverdoubted.icu



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