The Halloween Bet

By Aldric

This story is intended for ADULTS ONLY. It contains depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

Comments may be sent to pietar_the_fearless@yahoo.com . Note that the underscores (between pietar, the, and fearless) are part of the name and must be included.

This story depicts minors in unusual conditions that may include unprotected, unsafe sex or extreme humiliation. Obviously, this does not describe real life and should not be taken as such. In the real world, behaviors as described in the story are not acceptable, tolerated, or legal. The reader should never confuse the difference between fiction and real life. This story is fictional.

The Halloween Bet

David and Darcy had the same birthday, October 31, Halloween. They looked alike, enough so that many people who didn’t know them thought they were twins. But they were slightly less than a day from being a year apart in age. David was born at seventeen minutes after midnight. Darcy a few minutes past eleven at night. But they were born a year apart.

Last Halloween, they had made a bet as to who would get the most candy. Each headed out at four in the afternoon. At that time, Darcy was seven hours from turning thirteen. David had been twelve for about fifteen hours. It was that one day, a portion of it only, when they were both the same age.

Now, two days short of eleven months later, David was worried. A year ago, with his bag full of candy, two older boys poured half of it into their bags and ran off. He told Darcy that the bet was off, but she just shook her head.

He pleaded with her. He had the most, but bigger kids had stolen most of it. He wanted to just declare it a tie. No bet.

“You were going to make me go trick or treating wearing nothing but a bath towel,” she said to him.

“And two clothes pins to hold it closed,” David muttered.

“If kids had stolen my candy, you would not have listened to any argument for why me, a few hours before turning thirteen, should not go in the costume you said I would wear if I lost the bet. A dozen of our friends heard the bet, and both of us asked them if it should be cancelled. Only two of your friends said yes. All the others said no.”

“But you would have been covered,” David pointed out. “They’d know you were naked under the towel, but they wouldn’t be able to see anything. But me? Everyone will see me!”

“Your dick is probably so small that nobody would notice it anyway,” his sister snickered.

She knew it was unfair. A boy who liked her had admitted that he and another boy had taken some of David’s candy. The boy was hoping to score a kiss with her. It was one she gladly paid. She was quite sure that David did not know any of that.

“Come on, quit stalling. You lost the bet. Try on the costume I got for you.”

She loved the way his face turned red. The way he pouted. The way his body seemed to get smaller as he stared at his costume. He was thirteen now, and had been for around fourteen hours. She was about to turn fourteen.

He started to pull it over his shorts.

“No, that won’t work,” she said. “You’ll have to take them off. And your underpants too. Let me see how you’re going to look going to seventy-five houses before you can stop.”

His chin quivered. He was close to crying. “Please? Come on Darcy, I’m a teenager now. I can’t be seen wearing this and nothing else. I’ll do anything.”

“Take your shirt off so you can try the top on too. Let me see the entire costume on you and maybe I’ll only make you go to fifty houses instead of seventy-five.” Hell, she thought to herself. She’d be happy if he only had to go to one house. Walking out the front door in his costume, with all of his friends seeing him, that was the real prize.

“Twenty-five?” he stuttered slightly.

“Thirty if you show me right now.” She knew he had to go. He couldn’t refuse; she knew too many things he’d done wrong. She wasn’t beyond blackmail and lies. And a session with their mother and a hairbrush would surely result if he refused to honor the bet.

With trembling hands, he removed his shirt. He couldn’t look at her as he slowly stripped. His shorts fell to his ankles, then removed. He stood there in his brand-new pair of boxers, a birthday gift to replace his white briefs.

“Those too,” she said when he stopped again.

He was her brother, and in truth, she loved him. But he was wild and reckless and had won more bets against her than he’d lost. But last year he went too far. Besides, he was now a teenager, even if only for a few hours so far. The oldest boy she’d ever seen naked was him, and that was back when he was seven. She wanted to see what he looked like.

He couldn’t look at her as he slowly pushed his boxers down to his ankle and stepped out of them. His sister still held his costume, so he had to face her and hold his hand out.

She was disappointed. She thought she knew what teen boys looked like, but what she saw didn’t impress her. His dick was no longer than her index finger and it hung down over a smooth sack that she could see held two small oblong shapes. His balls. At first, she thought he was hairless down there, but as she looked closer, she saw he did have a small growth of short hairs around the base of his penis. She handed him the ballerina costume.

He still remembered her words on the day he’d dared her with the bet. “And when you lose, which you will, you are going to wear a little ballerina costume and nothing else,” Darcy had said.

He quickly pulled on the tutu, noticing that it didn’t hang flat. It was stiff and it projected horizontally from his waist. It barely covered his privates, and any movement exposed them.

The top was a vest with two straps that went over his shoulder. It barely covered his nipples, and left the center of his chest and all of his belly exposed.

His sister went around behind him and fastened the straps to the back.

“Twirl,” she ordered. She laughed as the edges of the tutu rose an inch, exposing all of her brother’s private parts. When his back was to her, she could see all of his flat butt.

“Twenty-five houses,” she said. “But you have to go with your friends and start on Maple Street where so many of the kids you go to school with live. I’ll be behind you and counting the number of houses you visit, so don’t lose count and quit too soon or I’ll raise the number back to a hundred.”

“Please?” he begged again. “Everyone is going to see me naked.”

“Not naked. Your flat little nipples are hidden. You made the bet. I’ll let you out of the trick-or-treating, but only if you wear the costume at your party and get your birthday spanking from a girl you’ve invited.”

She knew he was already nervous about that. He was to celebrate his birthday at eight that evening. It was going to be his first boy-girl party since he was six. She knew that between 10 and 15 kids had been invited, and at least 6 of them were girls, including Brittney Harrison, a girl he had a crush on.

He shook his head. Bad enough going to twenty-five houses all but naked. But not in front of Brittney. But then a horrible thought occurred. Brittney Harrison lived on Maple Street. She might see him trick-or-treating. His dick began to grow as he thought about her seeing him in this stupid costume.

Darcy couldn’t help but notice her brother’s boner. She watched it grow. It twitched a few times. She saw him look up and knew she was looking at it. He quickly stripped off the costume and put his clothes back on.

“I won’t do it,” he said. “Tell Mom anything you want.”

“Even the thumb drive you have hidden in your closet? The one with the X-rated film that you and Casey Dewey watched on your computer?” Darcy saw his defiant expression melt away.

“You’re going, and you are going to carry two bags to collect candy. That will prevent you from being able to cover up. One house you have to go to is Brittney’s. Finish the dare including those two additions and Mom will never know the existence of that thumb drive.”

He was still standing there totally naked, his dick beginning to become flaccid. His mom could never know about what was on the drive he’d so carefully hidden. And Casey would kill him if he got in trouble for it too.

“Get back into the costume. It’s almost 3:30. Tell your friends you’ll meet them in the backyard at 4.”

His friends all knew about the bet. He had told them he wasn’t going to do it. Now he had no choice. Darcy knew too much. He wondered how she knew about it. Even where he had hidden the thumb drive. He was stuck. He put the costume back on, again letting his sister re-attach the straps on his back. Then he sent a group text and snuck though the house so that Mom wouldn’t see him. What he had to do next was going to be totally obscene.

He went out the back door, feeling horrible. His dick was hard, and he was hoping and praying that only a couple of his best friends would show up. But when they arrived, all hope was lost. There were seven of them. Four boys and three girls. Two sisters, but the third was Gretta Winslow. And he knew she like him.

“Oh, David,” she yelled. “I can, uh, see all of you!” The others laughed and gathered around. He felt hands on his butt and turned, causing Gretta’s hand to slide across his dick. She grabbed onto it for a second and gave it a slight squeeze before letting go.

“We really can see everything,” Casey said, feeling a bit bad for his friend. “How long to you have to stand out here like that?”

“I have to go to twenty-five houses on Maple Street. And one of them has to be Brittney’s.”

“Wow!” Steve Cartright said. “That’s like three blocks from here.”

Just then they all heard Darcy shout, “Linda Cartright! Turn that off immediately.”

They all turned and saw David’s sister coming out the back door. And then they looked at Steve’s older sister, who had her cell phone in her hand.

“I wasn’t…”

“You were recording it. I could see the image from the back door. Delete it. Steve, make sure she does.”

“I wasn’t going to show it to anybody,” Linda said. “I just wanted to, you know, have a look at it tonight. Then I was going to delete it.”

“It’s deleted,” Steve said.

“Look, David is paying off a very stupid bet he lost last year. And yes, you can see pretty much all of him. For that reason, he needs your help and protection. You’ve got to keep adults from seeing him. Keeping other kids from recording him. If I can’t trust you, then leave now.”

“We’ve got it, Darcy,” Casey said. “We’ll keep him safe. If it gets too hard, we’ll bring him back and maybe you can come up with something else.”

“Good. Glad to hear it. Just think what would happen if what Linda was recording ended up on a thumb drive somewhere and someone else found out about it.” She got the reaction she wanted from the only co-owner of the thumb drive. Neither of the other boys reacted at all.

“Get going. Right now, it is mostly preteens out. Kids your age will start trick-or-treating around in about an hour. Try to be back by then. Surround him to limit who can see him and who can get close.”

She watched as they closed around him and smiled as it was the three girls who took the sides and back so that they would be able to see him.

“Wait a second,” David said. “I gotta do something. You guys wait here.”

None of them waited. They followed David as he went behind his garage. Darcy kept her distance, but followed along as well.

“Shit, why couldn’t you guys wait back there,” her brother muttered. “I gotta do something before we get started.”

“Your sister said…”

“Yeah, Lucy, I heard her. But not in my backyard.”

Because of where his hand had gone the moment he was behind the garage, all the kids had a pretty good idea what it was he had to do. And none of them, especially the girls, wanted to miss out on that.

He swore when they all stood there watching him. But he couldn’t go prancing down the street with everything showing while he had a boner. He sighed and closed his eyes and gripped his dick and got started.

Only one of them had ever watched a boy do what he was doing. Casey and he had sat side-by-side jacking off while watching the X-rated film on the thumb drive. Casey had tried not to look, but he was curious. Now he watched with even greater interest since he wasn’t distracted by his own need and the fact that the movie was still playing.

Two minutes later, David’s breathing changed. His knees bent and his back arched. A moment later, three globs of white cum shot onto the back of his garage. He squeezed out a bit more, looked around and saw smiles on everyone’s faces, and shook his head. He’d just jacked off in front of 7 kids, including three girls. He hoped this afternoon wouldn’t get any worse.

Between crossing the street and gathering around him, they managed to keep any adults who were escorting younger kids from seeing that David was essentially naked. They made it to Maple Street without any encounters. But here, they needed to figure out how to go door-to-door without being caught.

It was Mia, Lucy McDonald’s twin sister, who solved the problem. “One of you will go to the door and say the words. If it is an adult, we’ll move on. But if it is a kid, we all go up.”

A girl of about fifteen answered. She laughed loudly when David said, “Trick or Treat.”

“Oh, I think a trick is in order,” the girl said. “You are either the stupidest or the bravest boy out tonight.” She looked from his crotch to his face. “Which one?”

As David answered, saying “The dumbest,” two kids, a boy and a girl both about ten ran up and pulled the edges of his Tutu up, exposing all of him. The girl leaned over and looked at his privates while the boy slapped David’s butt. Then they laughed and ran off laughing so hard they couldn’t catch their breath.

“I guess that’s a good trick,” the girl at the door said as David repositioned his substitute for clothing. She dropped a candy bar in each of his bags and then gave one to his friends. They hurried on to the next house.

They had to skip the next three as it was adults handing out the candy. Then David signed, knowing that the next house was Brittney Harrison’s, and she and two other girls in his grade were sitting on the front porch.

“David Brown, I love your costume,” Brittney said as she saw him and his friends gathered on the sidewalk in front of her house. “Come up here and let us have a better look.”

David felt his dick rising as he made his way up to the girl he loved.

“I think he likes you,” Beth Thompson said to Brittney as he approached.

“Well, at least part of him does.” Brittney knew that David liked her. And now she had a chance to see parts of him that interested her. She hadn’t ever seen any boy older than 7 naked, and never one with an erection.

“I like it,” she said as he stood n front of her and said the Halloween phrase. “I’ll give you your treat in a minute. But first, I need to know. How big is it? And don’t exaggerate or I’ll have to get a ruler and measure it myself.”

“I, uh don’t…”

“Don’t tell me you don’t know. I’ve heard that all boys measure their parts. But if you really don’t know, we have a ruler right here.” She had just remembered that they had left one used for pumpkin carving. She held it up. “In fact, let me just check for myself.”

David tried to back away, but Lucy and Mia held him in place. They wanted to hear the answer.

David’s whole body shook as the girl he loved touched his dick. She bent over, and he could feel her warm breath on it. It was too much for a boy who had only been thirteen years old for seventeen and a half hours. He managed to shoot twice before Brittney released his dick. Both bursts landed on the back of her wrist. Now he was horrified. She’d never like him after this.

“Well, at least I know you’re old enough to make stuff.” She held her wrist up. “Lick it clean, please.”

She didn’t sound at all angry. He bent over and licked his cum off the back of her hand.

“Four inches. Does that match your measurement?” she asked as he rose up again.

He was too overloaded with emotions to think. “Yeah, I guess. Last time I measured it was three and three-quarters. But that was a month ago.” Then he realized what he’d just admitted to.

She laughed, and gave him some candy. “I’ll see you in a few hours at your party.”

In a daze, he turned, and his friends, who were still holding out their bags for candy, failed for a few seconds to keep others from seeing him. Too late, they heard a deeper voice.

“Dance for us, ballerina.” “Dance, or lose the uniform.”

Matt Walker, age 15, was standing along with his ten-year-old brother and nine-year-old sister.

Scared that Matt might really leave him naked on Maple Street, David did all he knew about how to dance. Then he paused as his friends got between him and Matt.

“Don’t even begin to try and threaten me,” Matt hissed. “David, come here and let my sister get a good look at you.”

As David stepped forward, he heard Matt whisper. “His thing is hard. It’s called a boner. You can touch it if you want.”

The young girl smiled, and did reach out and gently touch him. “It’s solid, not like Johnny’s was that day when I got to touch him.” Her hand left his dick and gently felt around his balls. “But his balls feel the same.”

“You hear that, Brown? My sister thinks you’re the same size as our brother, who’s only ten.”

The girl’s hand dropped back to her side. “Thanks for letting me touch you,” she said.

Automatically, David said, “Your welcome.” Matt smiled and pushed his two younger siblings forward.

“Let’s get the hell out of here,” Casey whispered.

Darcy had been on the other side of the street, watching. She was seeing more and more teens hit the streets. She decided it was getting too dangerous to keep her brother out here while he was all but naked. She’d brought his shorts and caught up with them.

“Would you like to do the rest of the houses wearing your Halloween costume? Or would you rather wear just these and put the costume back on for your birthday party?” She held out his shorts.

“The shorts, please,” David whimpered. With his friends gathered around and looking, he stripped off the tutu and put on his shorts. He needed help getting the straps off to remove the top.

“I’ll be at home with these,” Darcy said. “You still have 23 more houses to do.” She turned and headed for home, knowing that her brother was still going to be embarrassed. He rarely went shirtless.

Going door-to-door now was only mildly embarrassing, and they got the required number of houses done in half an hour. Then the walk home.

“Mom and Dad are handing out candy now that the older teens are out and about,” Darcy said when her brother and friends arrived. “You can stay like you are, and everyone who helped you tonight is welcome to stay even if you didn’t invite them. But, before everyone goes home, Gretta is going to order you to remove your shorts for your birthday spanking. Don’t disappoint me by refusing.”

David’s eyes got wider, but he nodded his head. At least for the next hour, he had pants on.

Casey, Tom, Luis, and Sam, the boys who had gone to Maple Street with him, were all invited to the party, along with five other boys, so they stayed. Brittney and the two girls who had been with her were also on the invite list, plus three more. David was scared stiff that when it was time for his traditional birthday spanking that all of them were going to see him naked.

There was cake and ice cream, which Darcy brought out. The invitations had specified no presents, that he got enough from family. Something new was dancing, but only one boy was brave enough to dance. The others watched him and a girl he liked, Lindsay Atkins, dance to a couple of songs, and then they just talked.

Finally, the moment many of had been looking forward to, and the one David hoped would never happen, arrived.

“It’s nine o’clock,” Darcy said. “One thing left to do, and then it is time for all to go home. David, it’s time for your birthday spanking. And you told me you wanted to do something different this time, so why don’t you announce it yourself.” She loved the look of absolute horror on her brother’s face.

“I, uh, well, it was kind of Gretta’s idea, that, uh…”

“I’m going to spank him,” Gretta cut in. “Only, we agreed that just like a punishment spanking, he will be naked.” She looked at him. “David, please remove your shorts and bend over the table here.”

“No way he agreed to that,” Noah Flemming muttered. But he was as surprised as most of the other guests when David unsnapped his shorts and let them fall to his ankles, revealing that he had nothing on under them. David stepped out of them and moved to where Gretta stood and leaned over the table. He saw that she had picked the perfect spot, for once his chest was on the table, his dick and balls hung straight down, in clear view of all of his guests.

The slaps were birthday slaps. They wouldn’t have hurt a child. Everyone counted them out, but all eyes were on the thickening flesh hanging down from David’s groin. Behind it was a smooth sack where they could clearly see his two balls.

As soon as the fourteenth slap landed, David jumped up and looked for his shorts, but they were gone.

“Thank your guests for coming,” Darcy said to him.

The girls who were seeing him naked for the first time came forward. Once the first one hugged him and said goodbye, the others did the same. Then Brittney. Getta was last. The boys kept their distance, but did look at David as he stood there with nothing on but shoes and socks, his erection pointing up towards the stars.

Casey, Luis, and Tom had been invited to spend the night. Sam had been too, but he’d gotten into trouble and had to return home right after the party. The four boys went to David’s room.

“Man, I never could have done that,” Luis said, patting David on the back. “I’m almost jealous. You got to hug some of the prettiest girls in our grade.”

“Yeah, while his dick was pressing against them,” Tom pointed out. “Still, it was a hell of a show. What’s the bet for next year?”

“I’m never betting anything again,” David said.

“Guys, we have a surprise for you,” Casey said. “We managed to get hold of something, and you’re both going to want to be naked for this.” He nodded to David, who went to his closet while Casey locked the door to the bedroom.

On the other side of the wall, Darcy, Brittney, and Gretta could hear every word. More than that. The camera she’d hidden was working perfectly. It was too bad Sam wasn’t there; it would have been nice to see him.

They watched as the boys crowded together on David’s bed. Only David and Casey were naked, and Gretta was focused on Casey. She’d seen David.

“Don’t worry, they’ll all be naked soon,” Darcy said to her.

The thumb drive was inserted into the T.V. in David’s room and it started immediately.

What the fuck?” Casey asked as the image showed David standing in his room, completely naked. Then they heard Darcy’s voice.

“Come on, quit stalling. You lost the bet. Try on the costume I got for you.”

He started to pull it over his shorts.

“No, that won’t work,” she said. “You’ll have to take them off. And your underpants too. Let me see how you’re going to look going to seventy-five houses before you can stop.”

“Please? Come on Darcy, I’m a teenager now. I can’t be seen wearing this and nothing else. I’ll do anything.”

“Take your shirt off so you can try the top on too. Let me see the entire costume on you and maybe I’ll only make you go to fifty houses instead of seventy-five.”

“Twenty-five?” he stuttered slightly.

“Thirty if you show me right now.”

The boys watched as the on-screen David removed his shirt His shorts fell to his ankles, then removed. He stood there in his brand-new pair of boxers, a birthday gift to replace his white briefs.

“Those too,” she said when he stopped again.

The T.V. David slowly pushed his boxers down to his ankles and stepped out of them. His sister still held his costume, so he had to face her and hold his hand out.

“Twirl,” she ordered as soon as he had the full costume on.

“Twenty-five houses,” she said. “But you have to go with your friends and start on Maple Street where so many of the kids you go to school with live. I’ll be behind you and counting the number of houses you visit, so don’t lose count and quit too soon or I’ll raise the number back to a hundred.”

“Please?” he begged again. “Everyone is going to see me naked.”

“Not naked. Your flat little nipples are hidden. You made the bet. I’ll let you out of the trick-or-treating, but only if you wear the costume at your party and get your birthday spanking from a girl you’ve invited.”

The image on the screen faded, and then the movie that Casey and David had expected started.

“Wait, pause that a second,” Casey said. “Tell me you put that on the thumb drive and that your sister didn’t find it.”

“She did. I don’t know how. I didn’t know she got that video, or when she put it on the thumb drive. That’s how she got me to go out trick or treating while I was basically naked. She won’t tell; she promised that. And I did all that she demanded.”

Nobody said anything, and David resumed the movie.

Darcy had watched it, and knew how much time would go by before things in her brother’s room would get more interesting. She, Brittney, and Gretta talked until it was time. Then she went back to the image from the camera she had hidden in her brother’s room.

Luis and Tom were fidgeting. On one side, David was naked, his dick sticking up and he was stroking it. At the end side, Casey was doing the same. After a few minutes, Luis mumbled something and then he quickly removed his shorts and underpants, revealing his erection. He also began jacking off.

Seeing the two of them doing it, Tom lost his fear of being seen naked and hard by his friends.

The girls watched them though the entire movie. They got to see all four of them masturbate several times. “Remember, you can never tell anyone about this,” Darcy said.

“I won’t. Nobody would ever believe us anyway.”

Two days later, David had to face many kids who had heard about, or seen, his daring costume. He was teased, although most of it was friendly teasing. He realized that dozens of kids his age had seen him naked and several had watched him jack off. The only one who was rude was Matt Walker, who was in ninth grade. But when he talked about how David had asked his sister to touch him, kids turned on him. He stopped trying to embarrass David with it.

He was the topic of many conversations for a week or so, and then it gradually quieted down. He and Casey had watched social media, but saw nothing that could have been related to him. Sam, the boy who missed out on the overnight on David’ birthday was still in sixth grade, and he reported a lot of discussion that lasted for a day or two, and then he heard nothing.

And they did watch the movie again, this time with Sam there to watch. David even let him watch the part his sister had added. David watched as Sam played with his dick, and noticed that even though he had no hair, Sam was able to shoot a little cum.

Many kids proposed bets, but David turned them all down. He’d learned just how horrible a failed dare or bet could be.

The End