Frank's Halloween dare

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Re: Frank's Halloween dare

Post by WillyWanka »

Jeepman89 wrote: Sat Mar 21, 2020 7:14 pm Damn. I had a long entry and I lost it all while trying to post it. It was Frank's Dare at the pool. Very upsetting since I worked on it for a while. I have no idea how it got deleted. Grrrrrrrrrrrrr
This is horrible and sad. My advice, write it in a txt file before posting it. Had the same with other forums when writing over a longer time, that the connection somehow fckd up and all was gone.
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Re: Frank's Halloween dare

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I
Last edited by Jeepman89 on Fri Sep 22, 2023 4:18 am, edited 1 time in total.
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Re: Frank's Halloween dare

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The girls in Tyler's class are 9-11. She is 14 and Frank is 17
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Re: Frank's Halloween dare

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Part 3 Frank's Pool Dare

After doing the schoolyard dare for Carly and her friends, I was excited that I got away with it without getting into trouble. I managed to go through that schoolyard wearing just a hat and sunglasses for a large group of schoolgirls and then back to the park to get my clothes and bike.

The following Saturday morning, I was back at the park when I noticed Carly with her sister Cammie and an older girl who I hadn't seen before. They were sitting on the swings and as I approached them, the 2 sisters jumped up and down very excited to see me. Carly introduced her friend as Tyler who was 14. Just to recap, Carly is 12 and Cammie is 10. "Hey Frank! Nice to see you again!" she said. "I told Tyler all about you and she still doesn't believe it."

Cammie told Tyler all about the schoolyard dare and how she and her friends followed me around and were close enough to even slap my balls, penis, and ass. "It was crazy! He didn't care who saw him and was right there in our yard wearing just a hat and sunglasses. Then we even followed him to the park." A few pics from Carly's phone were all that was needed to convince Tyler. She showed her a few of my Halloween dare in the park and a few of the schoolyard dare. Tyler was in shock saying, "Oh my God! You're just wearing a mask with all those girls around you. Weren't you embarrassed to be seen totally bare naked?" Then she laughed when she saw a pic of me being chased by all those schoolgirls in the yard. She couldn't help but notice that I had quite a hardon in a few pics. I told her that as embarrassing as it was, it was also quite exciting and that's why I did it.

Carly went on to explain that I was 17 and liked doing crazy dares that involved me being naked in public where people could actually see me. Before then, none of the girls had seen a naked guy in person and it was the same for Tyler as it turned out. "You guys are lucky!" she told them. "Too bad I missed it." Carly told her all she had to do was to give me a dare. "Yes, the crazier the dare, the better." I said. "The riskier the dare, the more excited I get!" Cammie said, "How about at the pool tonight, Tyler?" Apparently Tyler gave swimming lessons on Saturday evenings to a group of ten girls aged 9-12 at the community pool and the 2 sisters were part of that group.

"Oh, wow, that's perfect!" Tyler said. "I dare you to show up tonight at the Jefferson outdoor Pool just after 7 pm. I dare you to get naked in the pool with all the girls there! Also, you have to wear a speedo to the pool and that's all." Carly and Cammie laughed and showed their approval and I did not hesitate to accept the dare. "It sounds risky but as long as I don't get arrested, I'll do it." Tyler explained that I was to call her when I arrived and she would let me in through the gate. The pool was surrounded by a fence which was mostly lined with trees that would provide some cover. We exchanged phone numbers and I got on my bike to the sound of high fives and uproarious laughter.

Later that day, I managed to find an old speedo I used to wear in swim class that was way too small for me. As luck would have it, my parents were away for the weekend so I had the run of the house. Not having a choice, I put on the speedo, locked the door, hid the house key under a pot, grabbed my phone, got on my bike and pedalled away. The speedos were very tight and the large bulge in them was obvious. I got more than a few looks as I made my way through the streets to Jefferson Pool. After all, all I was wearing was a small speedo and was barefoot as well. I was very excited as I saw the Community Centre and rode around the back towards the outdoor pool.

Tyler and her 10 pupils made their way to the pool from the locker room wearing their matching blue one piece bathing suits. Most of the girls expected a typical lesson of doing the various strokes and possibly diving techniques. Only Tyler, Carly, and Cammie knew that this would be a special lesson and found it hard to control their giggling. Luckily, the moms never stayed for practice and would be back in an hour to pick up the girls. Tyler blew her whistle and her pupils got into the pool waiting for instructions. Tyler stayed on the deck while the younger girls remained in the shallow end.

I parked my bike between 2 trees and walked to the gate with my phone. I could see all the girls through the fence when I dialled Tyler's number. I hid my phone with my bike as she made her way to the gate, opened it and let me in. "Wow, you actually came!" she said. "Of course." I replied. "A dare is a dare!" She couldn't help but giggle when she saw me in my speedos and her eyes went straight to my bulge which was prominent due to my excitement. "Frank, I want you to show the girls how to dive. When you get to the diving board, take your suit off and dive in totally naked. Do 3 dives then swim to the shallow end. That's the dare! The girls will freak out!"

As I followed Tyler towards the girls, I couldn't help but notice how good she looked in her bathing suit. She had a nice bubble butt which had a serious effect on my speedos. Their eyes were all on me as we both stopped on the deck in front of them. They were staring, giggling and whispering amongst themselves no doubt wondering who I was and why I was there and why this older guy was wearing a skimpy little speedo with a huge bulge to boot. Tyler introduced me to all the girls and told them that I would be assisting in this evening's lesson. Carly and Cammie fought hard to keep a straight face as she said, "Frank has offered to show us some diving techniques which we will all be practicing later."

She nodded to me and I walked towards the deep end and climbed the 3 foot ladder leading to the diving board. I was so excited that I could hardly control my shaking as I grabbed the sides of my speedo and quickly pulled them down to my ankles before kicking them off into the pool below. All the girls were in total shock when I raised my arms in preparation for my first dive. Not being a large pool, the girls had a pretty good view of me in all my glory. The eruption of laughter was insane. It was an exhibitionist's dream. I remained on the board as all the girls couldn't believe what they were seeing. Cammie and Carly had seen it all before but they didn't show it. They seemed as excited as all the others. Tyler couldn't wipe the smile off her face as her eyes locked onto my swollen penis which jetted out towards the water in front of all the girls.

"Oh my God! He's completely naked! Look at his wiener! It's so big! I see his balls too! Is this for real! Isn't he embarrassed that we see everything! Wow!" I soaked it all in and proceeded to dive into the water to the applause of all the girls. Luckily, I took swimming lessons for a few years and was an excellent swimmer and diver. Tyler was worried that some of the younger girls might be upset at what they were witnessing but she didn't have to worry. They were all having a great time and I have to admit that I was too. Cammie and Carly were happy to have more girls to share memories with- memories of me totally bare ass naked.

When I climbed out of the pool for my next dive, the girls hooted and hollered as I attempted my second dive. One of the girls yelled, "Don't hurt your peepee!" before I plunged into the water again. By the time I was ready for my 3rd dive, I had a rock hard penis and I didn't care who knew it. I even got many comments about my ass every time I walked towards the diving board. After diving in, I started to swim towards the shallow end where all the girls were assembled jumping up and down in anticipation of my arrival.

By this time, Tyler had joined the other girls in the pool and as I reached the shallow end, Carly was the first to welcome me as she pulled me towards the group of girls. She was also the first to put her hands on my ass and invite the others to join in. Cammie was even bolder and grabbed my dick and even pulled me towards the others using that method. I did not resist and just allowed the girls to touch me wherever they wanted. Tyler was surprised at what these girls were doing and just laughed before blowing her whistle. "Everybody out of the pool!" she yelled. "That means you too, Frank!"

The girls wasted no time in getting out onto the deck and lining up. I was the last to get out and all eyes were on me as I climbed out and joined them on the deck. Tyler and her 10 pupils wearing their one piece bathing suits and me wearing my birthday suit! With each and every dare I did, I was getting more and more daring. There was no better high than being totally bare naked in front of girls in a place where you shouldn't be naked. The fact that most of them were seeing a naked guy for the first time made it even more exciting.

Tyler told me to get to the front of the line and as I walked past them, I made sure to have my hard cock rub against their legs, stomachs, asses. Some were swatting at my dick as I went by as I kept apologizing for my erection until I reached the front of the line. Now that I was not hidden by the water and I was very close to the girls, they had a great view of everything I had to offer and I showed it all. I swung my hard cock, allowing them to see my balls and shook my naked ass at them as they exploded in laughter at the scene I was creating. I don't think Tyler, Carly, and Cammie expected me to put on this kind of show for the swimming class.

We proceeded to walk towards the deep end for the diving session. One by one we would climb the ladder and dive into the water until everyone had 5 dives. Needless to say, waiting in line was an experience of being rubbed, poked, groped, slapped. When a girl was in front of me in line, my dick would be poking her in the butt resulting in a lot of giggling and outright laughing. I noticed that my speedo was nowhere to be found. At this point, I really didn't care and was wondering how the session would end.

Tyler blew her whistle, ending the diving session and assembling the girls in the bleachers where they put their towels around themselves and sat down. Tyler asked me to stand in front of them all wet and bare naked. My cock was still semi hard at this point and the water didn't seem to have its normal effect. She instructed Carly to towel me off as she spoke. "Girls, I hope you enjoyed today's lesson and learned something about diving." The girls all laughed loudly at that comment. She invited the girls to make comments about what they learned and they didn't hold back. Diving wasn't even mentioned.

"I learned that Frank has a big wiener! I got to touch his balls! I learned he has a nice ass! I got to swim with a naked boy! He's not a boy! He's a man! Look at his big boner! I swam with a naked guy! He poked my butt with his wiener! His dick got bigger and harder when we touched him!" The comments made me even harder if that's even possible. The comments plus Carly rubbing my body with that towel almost put me over the edge.

Tyler was happy that they all had a good time but warned them that it was to be a secret or they would all be in trouble. I was the one that had the most to lose actually but the excitement I felt during my dares seemed to nullify that fear for some reason. Tyler explained that maybe I would agree to help with further lessons in the future and I'm sure that information would guarantee their silence. They all promised to keep what they saw to themselves and all thanked me by applauding wildly. There wasn't much time left as the moms would be arriving soon. Carly threw the towel towards the bleachers leaving me totally bare naked in front of the girls again. She proceeded to grab my dick which made all the girls pay close attention. "Watch this guys!" she said as she started rubbing her hand on my hard cock. She actually started stroking my cock up and down. I couldn't stop her. I chose not to stop her. These young girls were all watching intently as Tyler joined her and both girls now had their hands on my hard cock. Two hands stroking my dick at the same time, up and down, harder and harder. The girls' eyes were glued to my big throbbing cock as I could not take much more. "Watch this guys!" Tyler said, as I reached the point of no return. The girls mouths were open in shock taking in a scene that would be a highlight for years to come. It was at that very moment when I knew the inevitable would happen. As my body shook, Carly and Tyler sensed it too and let go of my cock, allowing me to stand in front of all the girls with my dick pointing straight at them all. It was an explosion of cum streaming from my cock that the girls all saw for the first time in their lives! Stream after stream splashing onto the pool deck in front of them as they all screamed. The looks on their faces told the story. I had just cum in front of these girls aged 9-12 and it was incredible. There was no going back now. I had no more secrets from them.

The next few moments were hectic to say the least. Once it was all over, the girls could not contain their excitement and crowded around me talking about what they had just seen and staring not only at my cock but at the mess I had made on the deck tiles. Tyler was worried about the moms showing up and quickly threw me a towel so that I could clean myself off. The girls made their way to the locker room as Tyler and I reached the gate. She let me out and told me to leave quickly before anyone would see me. When I asked for my speedos, Tyler laughed and said, "That's the final dare, Frank. I dare you to ride home completely naked! Hopefully nobody will see you! Thanks for everything! The girls loved the show, Frank. Hope to see you soon.....all of you! Hahahahaha." With that I hopped on my bike, held on to my phone and pedalled away, naked as the day I was born.
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Frank's next dare

Post by Jeepman89 »

Any ideas for Frank's next dare?
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Re: Frank's Halloween dare

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Who should be at this picnic?
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Re: Frank's Halloween dare

Post by Themarble »

That 3rd chapter was soo good. :D
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Re: Frank's Halloween dare

Post by Jeepman89 »

Thanks, Marble. Any ideas for Frank's next dare?
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Re: Frank's Halloween dare

Post by Themarble »

The way i see this going is that Frank is gonna take more and more risks and the girls are gonna egg him on, fueling the fire that is inside Frank. I think maybe for Frank's next dare it could include an aspect that he will be in a more public setting. You mentioned in the brief about his character that he did stuff in a waterpark so it maybe a good idea for him to encounter the girls there as there are many ways to go with that or something else could be something like a library.
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Re: Frank's Halloween dare

Post by Themarble »

If you want me to elaborate a bit more on it feel free to ask as I have ideas to each of those but id rather see what becomes of it. For a basic idea for the water park he can strip under the water and be shown off to more girls. This would make the girls more likely to touch him as no one else can dee what they are seeing😂.
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