Sailing the BVI (British Virgin Islands) 1 to 12

By WhoDaMan
who.da.man.2000@gmail.com

Copyright 2021 by WhoDaMan, all rights reserved

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and sexual activity of preteen and young teen children for the purpose of punishment. None of the behaviors in this story should be attempted in real life, as that would be harmful and/or illegal. If you are not of legal age in your community to read or view such material, please leave now.

Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 1 - Surprise!

It was a week before summer break. Tad was looking forward to the end of classes and getting to hang with his buddies for the summer. He would be moving from the 8^th grade to high school next fall. It was an extremely exciting time for him. Most kids don’t enjoy school that much (or at least they say they don’t) but he did enjoy it, but he was also looking forward to the break.

Tad’s family had sat down for dinner, he, his dad, his mom, his two younger sisters. His dad interrupted the jostling for food. “Kids, I have some really great news. So, your mother and I have picked a vacation destination for us. We have been talking with the Walkers. Well, more than talking, planning. We came up with a really great vacation. We will be going sailing on a catamaran. It’s a huge boat. It has 4 cabins, a nice kitchen, a really good lounging area below deck, a great deck on the back of the boat. We added noodles, paddle boards, snorkeling gear, the works. Ben Walker is a certified skipper, so he will show us how to operate the sails and get across the water. We are going to the British Virgin Islands!”

The kids just stared for a minute. They were in disbelief. They had all been mapping out what they were going to do as soon as school let out, and this vacation caught them all off guard. Tad’s sister Katie had been planning her outings and sleep overs with her other 12-year-old friends. His littlest sister Amy has been into detective work recently, and she had planned to solve some mysteries that her friends and she had discovered (or invented) involving her friend Casey’s older brother.

All three kids started complaining on queue. Mom shushed them all. “Now, we’ve been saving for a while for this vacation. We all talked about this. I don’t want to hear a bunch of whining. We leave Saturday the week after school lets out. We have some shopping to do, packing… We’re going to need all of you to help on this. You each need to take care of your part. We made some checklists of things we need you each to do. After dinner we’ll have a family meeting and go over it all. Besides, a couple of other families said they were going to do the same vacation, they just can’t leave the same day we do. Some of your friends from school might be there. We even agreed to meet up early in the trip.”

The kids all knew to not continue complaining. It was quiet for a while. At some point Katie broke the ice asking about the place they we’re going. Mom told her that it was a spot the parents had gone to when they were just out of college. It was supposed to be the best snorkeling and sailing in the world. For Katie, mom added “and there will be plenty of cute guys running around”. This made Katie smile, but she was still disappointed having her summer plans changed.

The good news was that the Walker kids were really good friends with the Comptons. Amy’s best friend and fellow detective was Sally Walker. They were both 10 years old and ready to solve all the world’s issues. 12-year-old Mary Walker was one of Katie’s circle of best friends. There were 4 of them and they all were pretty tight.

For Tad, there was Winifred, or Winnie Walker. She was his age, 13 going on 14. They weren’t friends and didn’t hang out, but Tad was obsessed with Winnie. He always blushed when he saw her or she spoke to him. She was very cute, had blossomed well as puberty hit her. She was a cheerleader in Middle School and would likely continue that in High School. Winnie played it down, but she had a thing for Tad as well, so this would be an interesting vacation. Tad started thinking maybe he could use this time to his advantage.

That left the Walker’s oldest son Brett. He was 16 and a bit of a bully. He had made it his goal in life to make Tad’s life miserable. It was the only reason Tad hated going to the Walker’s for dinner or having them come to his house. It didn’t happen that often, but when it did, Brett was too much for Tad. Brett’s parents were having trouble controlling him.

The last time they had come to the Compton’s for dinner, about 3 months ago, Brett embarrassed Tad in front of the girls. The Walkers were supposed to arrive at 6:30. Tad had taken a shower, as he wanted to be clean and smell nice in case he ended up talking to or sitting next to Winnie. The Walkers arrived at 6:00, a half hour early. Tad was in the bathroom getting ready. Mrs. Compton had said as much when she invited the family in. The parents all headed for the kitchen.

Knowing Tad was in there, Brett walked over to the door to the bathroom which also connected to Tad’s bedroom. Normally Tad would have locked the door, but his sisters shared a bathroom upstairs and his parents had a bathroom of their own in the master suite. He didn’t expect any one to try to enter, so he was not always diligent about locking the door to the living room and hallway. Brett grabbed the door, quickly twisting the handle and whipping the door open. There stood Tad drying off with a towel. The girls only got fleeting glances as Tad covered up really quickly, but he wasn’t sure how much they saw. Brett was laughing so hard, he had let go of the doorknob, and Tad quickly slammed it shut.

Tad later told the parents what had happened. They half-heartedly scolded Brett and told Tad not to worry too much about it, “no one is interested in seeing you naked, and besides, boys are way too modest for their own good. Why when I was a kid…” and the conversation deteriorated into a discussion about playing naked in the sprinkler and at the beach, skinny dipping in the creek, naked spankings and corner time, and forced nude swimming in school for boys. It was a familiar conversation that came up time and time again. During the conversation, the parents did note that boys were better behaved back then.

All evening, Tad avoided making eye contact or speaking to any of the girls as he was thoroughly embarrassed and could not imagine finding out that they had seen anything. Each time he did look in the direction of any of the girls, they just grinned at him with that knowing smile. It made his insides knot up. He was very body shy. He had been made to shower and dress in PE with the other boys. It took some getting used to, but then again, these were boys, not girls, and the other boys had to change as well. It was a different matter being exposed to a bunch of clothed kids of both genders.

As the evening was winding down, Tad quietly walked towards his room. He passed Winnie. Without looking up, he gave her a quick greeting, “Goodnight Winnie”, then he hurried to his room and locked the door behind him. He pounced on his bed on his stomach and pounded the pillow in anger. Brett had managed to ruin another chance for him to spend time with Winnie.

Tad slowly opened up conversation with Winnie at school. She never mentioned the incident. ‘Maybe she didn’t see anything’, Tad thought to himself. Over time, he forgot all about it. Winnie had seen a little something. Just a glance, but it was enough to pique her interest and, since she already had a bit of a crush on Tad, it added to her daydreams that girls have about boys.

You see, girls have a lot of the same thoughts that boys have. They have a lot of the same conversations boys have about the opposite sex. They get excited looking at paintings and sculptures of naked males. The difference is, girls giggle about it and hide it pretty well, and no one wants to think their little girls are hormone crazed youths anxious to devour boys. No, we try to put all that onto the boys who, let’s be honest, are just as crazed, but not as good at hiding it. It doesn’t help that people expect obnoxious behavior and comments from boys, which makes them look for it and find it, even if sometimes it’s not there.

And now they will be spending over two weeks with wonderful Winnie, Brett the bully, and their whole family. Not only that, they will be sharing a very tight spaced catamaran! Tad was both excited and worried. Worried what Brett would do, but anxious to finally be in a position to make a move to get Winnie to go out with him.





Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 2 - The Departure

The end of school finally came and went. It was a stressful week. Tad’s mom and Dad were constantly going over lists of things to take, making sure their provisions would be ready when they arrived, confirming the boat reservation, selecting the options to have on board. The worst was packing. Tad’s mom was trying to be the consummate organizer with packing. They needed to divvy up stuff to be put in the checked bags luggage. Flippers, snorkeling masks, changes of clothes, swim wear, snacks… The list goes on. Tad’s mom made a list of items the kids would each carry in their back packs, which would be their carry-on personal item.

Tad had been given socks and underwear. Yuck he thought at first. Everyone’s underwear… Then his teenage mind took over. He had his sisters’ panties in there… It didn’t take him to perv-nirvana, it was his two younger sisters we’re talking about, but it was girls panties after all. A taboo in their house. You didn’t talk about them or the bras. You certainly weren’t allowed to touch them. The girls didn’t want a boy touching or even looking at them. Sure, the girls handled his underwear when helping with the laundry, but then, that’s different, right? Girls would never pick them up, look at them, make stupid comments, etc. Naw, never.

Anyway, his sister Katie was given swimwear. She was confused. How had Tad gotten to carry her underwear and she had to lug around his swimsuit? His mother had explained it based on volume. There were fewer swimsuits, so it left more room in her backpack for her other stuff. Tad had taken Katie his swimsuit. Katie snatched it angrily from his hands. When she delivered her underwear, she had placed them in a zip lock bag all rolled up tight and sealed away from curious eyes.

A little later, as she was walking past Tad’s room. He had heard her coming. He pulled out one of her pairs of panties and as she passed his door, he made sure she saw he was holding them. He wasn’t doing anything dirty with them, just holding them, and gloating at her to annoy her. She went over and took the panties, rolled them up, placed them back in the zip lock, and took her zip lock from him. She would have the last laugh. She put them into a makeup bag she had that she could put a small padlock on. Then she walked over to her backpack and took his swimsuit out and hid it in cabinet in her bathroom. She returned with the locked bag and a smug look on her face. Tad kind of chuckled inside. ‘Well played little girl, well played.’ If he had only known she had hidden his swim trunks. Later she returned his swim trunks to his dresser so it would look like he had forgotten them.

The rest of the stuff was divvied up and placed in bags. Taxi cabs arrived. They would be gone way too long to pay for parking at the airport. The families loaded up and their adventure was about to begin. They travelled to the airport as separate families. The parents wanted one last opportunity to talk to the kids about their behavior and what was expected of them before combining their lives for the next 3 plus weeks. There were the usual topics about respecting people’s privacy (a stern look was given Brett’s way), being polite and respectful to the adults, and then a surprise set of instructions.

It was decided that there would be consequences for bad behavior. These consequences would be handed out in front of the whole group on the deck of the boat. The thought was that that might deter some of the expected behavior. They were instructed that whatever your bad behavior was, it would be met with a similar type of punishment. If you strike someone or hurt them, then you would get a spanking. A few gasps were heard at this description, as neither family had used corporal punishment for a long time. Another, if you invade someone’s privacy, you will have yours invaded to a similar degree, in front of everyone. More gasps. If you took something belonging to someone else without permission, you would lose something similar of yours for the remainder of the trip. If your behavior was bad enough, some of the punishments may be lengthened to days ow even weeks.

The parents were sure by the quietness in the vans that they had made their point. They were hoping for the best behavior from the kids for 3 weeks. Fat chance. Long hot days, sun burn, close proximity, no TV… it was a recipe for danger. After a quiet and uneventful trip, they arrived at the airport. They carted their bags to the departure counter, checked them in, and went though security.

The security lines were longer than usual. Its actually expected as everyone is heading out on vacation, but no one is prepared for it. Of course, Ben Walker had expected this. He had signed up for TSA pre-check. He had also convinced Tom Compton to do the same for his family. Everyone was delighted as they were allowed to pass the long line and enter a different path-way and straight to the screening area. ‘Belts, shoes, laptops, empty your pockets…’ the usual dance. Everyone got through and redressed. To the gate!

It was over 4 hours, but they touched down at St. Thomas. They went to baggage claim, grabbed their bags, and then loaded up in the charter pane for the short hop to Tortola. The had to take 2 different flights to get everyone over. Just when you think its about over and you can finally start your vacation, Oh, yes, customs. Ten dollars a bag. Long waits. The officials are in no hurry. After a long grueling day, you are loaded into vans, and the taxi’s take you to the Yatch Marina.

The company does a check out on the boat and declares your group good to go. Yea!. Finally. The Catamaran has 6 cabins. The cabins will be kind of close quarters. The parents have 1 of the cabins each, the two older girls have a cabin, The three younger girls have a cabin, and the boys have a cabin. The last cabin is for storage. Tad is beside himself. He had never imagined ending up with Brett as a room mate. What makes matters worse, the beds are really just a mattress and a half, on a board structure that essentially makes it one bed!

This is starting to look like the vacation from hell….



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 3 - Night 1 – In the Thick of It

After some grumbling and listening to the parents tell them that there just wasn’t any other way, Everyone moved their stuff into their cabins. The girls did a pretty good job of sharing storage space and bathroom space. It was apparent that the boys were going to have a problem. In anticipation, Mrs. Compton had told her husband that she would put their stuff away if he would over see the boys getting settled in. He was less than thrilled, but this is what they agreed to before they travelled here.

Mr. Compton entered in the middle of a dispute. “OK, boys, here’s how this is going to work. Brett, you’re the oldest, pick a side of the bed.” Brett chose the side by the small narrow window. “Tad, you get this side of the bed. You both will share half of the closet to hang your shirts in. You both get the compartments in the shelf on your side of the bed. Brett, pick one of the other storage bins.” Brett chose the one below the closet. About that time, Katie entered, reached in Tad’s backpack and grabbed her and her sister’s underwear and threw Tads shorts on the bed. She quickly exited.

“Tad, you get this one.” He opened the one that didn’t actually look like storage and it was actually the biggest one. Brett started to say something. Mr. Compton stopped him. I let you choose both first. It’s done. You boys can store your backpack at the end of your bed, or in the spare cabin. Feel free to use 1 storage locker in there if you want. I will give you 15 minutes before I let the girls have a look for storage. You can use the shirt locker, but it will be shared by everyone.

As Mr. Compton was about to leave, the boys started arguing. “Boys, this is the sort of thing that will get you in trouble. Now, cooperate, stay off each other’s side of the bed, stay out of each other’s stuff. That’s the end of it.” He walked off. Tad elected to move most of his stuff he didn’t want Brett getting into over to the spare cabin. He chose a storage locker near the back of the bed. He didn’t need the large storage he had been granted after Brett chose, so he told Brett he could have it. Tad was hoping that would keep Brett out of the spare cabin. Brett was surprised. “Thanks, little bro”. Tad was quick to reply, “I’m not your little bro, I’m not that much younger than you.” With that, Tad walked out of the cabin.

He was going to go somewhere, but all the cabins opened into one big space once you stepped upstairs. Tad walked out and around to the front deck. There was a trampoline between the two pontoons. There were also some bean bag chairs up next to the window of the family space. Tad dropped into a bean bag chair to sulk. His summer was ruined. Just then, Winnie plopped down in the chair next to him. Tad got a bit of a smile on his face.

“Finally, a smile!” Winnie pointed out. “Sorry, it’s just, this isn’t what I had planned for my summer, and now I have to room with Brett.” “Oh, it’s not that bad is it?” “Well, then you room with him” Tad replied comically. “No way! I get it. I hope you don’t let it ruin the whole trip. I think it could be fun.” “Yea, me too, I guess. Thanks for cheering me up.” “Hey, glad I could help.” Winnie reached over and put her hand on Tad’s bicep next to tad’s hand as she said that. Tad started to blush and tense up.

“Relax, I don’t bite” she said, “At least not until I get to know you better, if you know what I mean.” Tad wasn’t sure what she meant. He looked confused, but not wanting to seem stupid replied “Yea, sorry.” He smiled and put his hand on top of hers. Then he started over-thinking again. He looked to see if what he did was OK, she was smiling, so he relaxed a little and let their hands slide down to her forearm. Winnie slid them down on top of his hand. They sat and chatted for a little while.

The sun had set, and it wasn’t really late, but it felt late. Because they are at the beginning of the eastern time zone, the sun rises early and sets early. The mom’s started on dinner. Winnie jumped up. “I’m going to go help mom with dinner. Thanks for sitting with me.” Tad wanted to respond in kind. “Oh, it was no problem. Great. I was, it Um…” he replied, fumbling over his words. Winnie nervously giggled and headed to the family area. Tad leaned back and kicked his feet out. It was then that he noticed he had a raging hard on. ‘Oh, shit! Did she see that? Oh damn….’ Tad wasn’t sure what to think.

Inside, the moms saw Tad and Winnie sitting and chatting. When Winnie came in, they commented on how cute they looked together. Now it was Winnie’s turn to blush. “Well, he’s a nice guy. We had a good chat. I think he likes me” and she giggled. The moms were curious. “What makes you say that?” they asked. “Well, uh… he got a, uh, an uh, erection while we were talking. It was so cute. We learned about that in health class.” She was really blushing now, having pointed out a boy’s erection.

The moms were gently laughing. “What?” Winnie wasn’t sure why they were laughing at her. “Well, honey” her mom said, “I’m sure he does like you. He always has, but boys can’t control those things either. At that age, they are constantly going up and down.” Sally made a motion with her index finger pointing up then curving down and then back. The moms both laughed. “If only they kept working like that” she added. They looked at each other and started laughing harder. Winnie wasn’t sure what was going on at this point. The moms had gotten a little weird talking about Tad’s boner.

Tad’s sister Katie was on her way to the family space and stopped to listen. She heard everything. She walked in as the moms were laughing and carrying on. “So, Tadpole got a boner?” Winnie blushed really red at this point. She was both embarrassed and worried that it would get back to Tad that she talked about his penis getting erect. “That’s OK, he gets them at home all the time too. Luckily he knows had to get rid of them…” She turned towards her mother and finished with “right?” And tried to giggle.

It was a nervous giggle. He timing was off though. The moms stopped laughing and looked at each other. They had just been laughing about one of their sons’ boner and now they were about to talk about masturbating… The moms both cracked up again. “Choking the snake” “Tossing the cookies” “Pounding the pud” “Choking the chicken”. With each quip they laughed harder. When little Amy entered and said, “beating the meat”, they quickly stopped in shock. “Ooops” one of the moms said.

They both cracked up but then tried to set a straight face. “So, are you girls here to help with dinner?” Amy quickly replied, “Oh, I thought we were going to talk about boys doing that stuff.” Amy’s mom jumped in, “Honey, what do you know about that?” “Well, my friend Casey says her brother does it. We’re investigating to find out what it is. She heard her mom talking about it to Casey’s older sister. They were saying stuff like you guys were. We were going to try to google it and learn more about it.”

“Well, I can see it’s about time to have the talk!” Carol Compton finished with. “Honey, we will pick this up another time, but please don’t google that until we can talk about it, OK?” “Sure Mom. What’s for dinner?” she said innocently. Everyone else cracked up. They started working on dinner. Eventually everyone gathered, got a plate and started separating to find a spot to eat at. Some of them used the table in the family space. Tad retreated to the bean bag chair. It had been good so far. Winnie plopped down next to him again. Unfortunately, Katie plopped down on the other side.

After a little idle conversation, Katie looked at Tad and said “So, you popped wood in front of Winnie huh? Bet that was embarrassing. Glad I don’t have one of those things!” Winnie and Tad both blushed. They had a shocked look on their faces. They both just looked at Katie in disbelief. “What? Look, everyone in the kitchen was talking about it.”

With that, Tad got up, walked through the kitchen, dropped off his plate and headed to his cabin. He went in and locked the door. Everyone could tell something was wrong as he sped through. Winnie had tried to follow him to apologize. Katie followed to feed off the drama she had just cause. As the two girls entered the common area, everyone looked at them as if expecting an explanation. “I just said ‘so, I heard he popped wood in front of Winnie’. What’s the big deal?”

Her mother looked at her angrily. Partially because Katie was being an ass, partially because she felt guilty for letting that conversation get out of hand. She had a quick thought, “So, Katie, did you get your period yet?” Katie was floored. She ran out of the room and to her cabin. Now they had two children locked in their rooms, and everyone else was sitting in shock except Brett, who was laughing. He couldn’t help himself, “Better keep those two apart, she might end up pregnant.” Winnie punched him in the arm. Her mother admonished her, “Winnie, we said no hitting! You, we, you… We will have to talk about this. Go back up front and stay there until I come see you.” Winnie did as she was told.

Sally Walker had the parents all squeeze into one of the cabins to talk. They talked about what to do about Katie embarrassing Tad and about Winnie punching Brett. It was decided Winnie would get a spanking for punching Brett and Katie, while she was already reeling from getting a taste of her own medicine, would apologize to Tad and would do three of his chores.

Everyone was summoned to the family area. They were warned that anyone joking around would get a punishment as well. Everyone was quiet. Tad entered, blushing. He didn’t know what was going on, but he looked at Winnie who looked back at him with tears in her eyes.

Carol Compton got everyone’s attention. “OK, so, its punishment time. Katie, for embarrassing your brother, later, alone, you will apologize to your brother. We will ask him if he thought you were sincere, and you will do his next three chores. Katie started to object. Her father quickly shut her down. “Yes, ma-am.”

“Winnie, we warned everyone that hitting would result in a spanking, so I’m sorry to tell you that you will receive 3 swats with a stirring spoon.” Winnie started crying quietly. Everyone was shocked. No one had been spanked like, forever, and girls didn’t get punishments like that. Tad was shocked as well. He didn’t even know what had happened. He stepped forward. His dad went to pull him back and sit him down. Tad put his hand up to stop him. “This isn’t Winnie’s fault, its mine. I don’t think it’s right that she should have to get the spanking. I will take her spanking for her.

You could have heard a pin drop. No one could have expected that. The parents looked at each other not knowing what to do. They started shaking their heads yes as if to indicate OK. At this pint they all felt they should stop this and no one get a spanking, but no one spoke up. Finally, Carol spoke up, “OK, Tad, over here. Now, you know the same rules apply, this is with your pants down, on your underwear?” “Yes ma-am. Tad slowly undid his shorts, let them fall to the floor, and leaned over for his mother to spank him. Carol was crying, Winnie was crying, everyone else was in shock.

Carol gave Tad the swats on his cotton covered but. They had sounded really loud in the small space. She wasn’t sure how hard to swing but ended up giving them like she will for future infractions. Tad had started tearing up from the swats. They were very painful. He was rubbing his butt. His mom grabbed his shorts and lifted them up. He grabbed them and zipped up and headed to his room. Everyone just sat there in shock with Winnie still crying. After a short but quiet while, Mr. Compton suggested everyone call it a night and head off to their cabins. “Lights out at 9:30”.

Everyone got up and started to their rooms. Winnie went to Tad’s cabin and knocked. “Tad” she said through her tears, “I need to talk to you.” “Tomorrow Winnie, I just… Tomorrow, OK?” “OK” Winnie said, her crying intensifying. She headed to her cabin. She would eventually cry herself to sleep.

Brett entered their cabin. After some silence, he spoke up. “Bro, that was some next level shit right there.” Tad was expecting to be harassed. He was surprised by the statement. “What do you mean?” “Dude, you just stepped in and took her whacks, didn’t even hesitate. I think they all think you’re a rock start right now. I think Winpin is all yours too…”

“Her name is Winnie. And I am not a rock star. Rock stars don’t get embarrassed in front of everyone and then have to drop their pants and get their ass beat.” “Well, never seen nothin like it bro.” Tad thought for a second then added “Does this mean your gonna quit harassing me?” “Well, don’t get carried away…” Brett replied.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 4 - Day 2 – Dawn of a new Day

Tad woke up early. He thought it was early. The sun was well up. He had to look at his phone to get the time - 6:15. Wow, it seemed later. He got up and headed for the bathroom. He entered, turned and locked the door, and proceeded to pee. Next, he went to brush his teeth. As he moved in front of the mirror, there, written on his forehead, was the word ‘wood’ with a picture of a penis and balls. Tad quickly scrubbed it off. It was magic marker, so it wasn’t hard to remove. He brushed his teeth and headed up the coupe of steps up into the family space. He could see the back of Winnie’s head. She was sitting on their bean bags out front. He decided to face the music.

He started around on his way up. ‘What to say? Sorry I am immature and can’t control my hormones? Sorry I started this whole mess?’ Just as he rounded the corner, Winnie heard a sound, looked his way, and jumped up. She had been up before the sun, waiting to talk to him. She ran the few steps and grabbed him in a hug. “I am so sorry! I should have never said anything to our moms, and Katie overheard and then she said that to you, I’m so embarrassed, then I hit Brett, and you took my spanking! Oh my god, you are the best!” With that she leaned back and kissed him.

He kissed back. It wasn’t a Hollywood style kiss, they were inexperienced 14-year-olds, but it was both of their first kisses, they would remember this one. They kissed for what seemed like forever but was more like 15 seconds. Katie had been sitting there watching the whole time. She couldn’t help but think, well done brother, very well done. As they broke their embrace, Katie spoke up, “Get a room!”. They stared at each other, not knowing what to do then Tad gave her a quick peck on the lips and swung around to have seat, his hand still around her waist.

“Um, I, Uh… You hit your brother?” Tad was not there for the actions that happened after his embarrassment. “Yes, of course. I couldn’t let him talk to you like that. I am so sorry I embarrassed you. I didn’t know Katie was listening” she said giving Katie a mean look, “and I didn’t know our moms would joke around about it.” “Oh, god, they were joking around? Can this get any worse?” Winnie tilted her head, “well, then your little sister came in and was talking about stuff she didn’t understand and investigating, then the moms said they wanted to have ‘the talk’ with her and the others. I am so sorry.”

Then she leaned forward to whisper in his ear, “I think its a cute boner. I thought so ever since I got a peek at it a few months ago.” She leaned back with an embarrassed look but an evil grin on her face. Tad closed his eyes and shook his head. Winnie kissed him again. “If you love birds are just gonna keep this up, I’m out of here.” With that Katie headed back to the family area.

Breakfast was ready and people were migrating to the area. Tad and Winnie headed there too. It was obvious they were going to be attached to each other the rest of the trip. As Tad entered, his mom dropped what she was doing and rushed to give him a hug. “I am so sorry. Everything just happened so fast last night. I should have stopped it. You never should have had to be embarrassed again and then get a spanking. I am the worst mother ever.” Her voice was cracking and she was tearing up.

“I have never met a man that stepped up like you did last night. I was so proud of you stepping in and protecting Winnie.” She pulled him in for an even tighter hug. “Well, remember that next time I screw up!” They both laughed. As she headed back over to the kitchen area, she playfully swatted his butt. “Well, you did make my week harder dealing with your little sister you know! Now I have to have the talk with her.” “Maybe we’ll have some visual aids!” Katie had to add. Her mother was quick though, and responded “Oh, like a tampon?” Katie quickly shut up, not wanting to go there again.

It was time to set off for there first destination. The Marina crew helped them shove off, and they motored out to open water. They headed for Little harbor to do some snorkeling and swimming. As they arrived, Mr. Walker had the helm, and Mr. Compton showed the boys how to tie up to a mooring ball. There were a few jokes between them, as there always are when balls are involved. They got hooked up. Everyone went off to get changed to swim.

Brett went in the cabin and changed first. There really wasn’t enough space for them both to change at the same time, and that suited both of them. They were both a bit shy about being naked in front of others. Brett, because he was a bigger guy, at 16, but hadn’t gotten far into puberty yet and didn’t really want anyone to know, and Tad because he had always been shyer as a little kid ever since being embarrassed by being made to play in the sprinkler naked with his sister and neighbor kids. He was the only one naked, and the innocent little girls kept getting touchy feely.

Once Brett was changed, Tad went in to find his suit and get changed. He looked everywhere, but couldn’t find it, which is expected since his sister left it at home. He marched over to his sister and Winnie’s cabin. He knocked. “What?” was the annoyed sounding response. He turned the handle and opened the door. To his shock and their horror, there stood two naked girls in the midst of changing into their suits. He slammed the door closed just as Katie screamed. He ran back to his cabin not knowing what to do. In the meantime, the girls had locked the door and finished changing. Katie was furious, Winnie, not so much.

It wasn’t long before Mr. Compton entered Tad’s cabin. “So, I know the guy that made us all proud last night would not just go peeking in on girls dressing. Care to explain?“ Tad paused for a second, then explained. “I went to change into my swimsuit. I couldn’t find it. Katie had brought them in her backpack. I went to ask her to look in there for it. I knocked, she said ‘what’ and I opened the door. I never thought for a minute that they were naked, or I promise I would have never…”

His dad cut him off. “Well, first, I believe you. Second, never open a girl’s door. Always let them open it. It’s the safe play. I am going to have to meet with the other parents to talk about this, but your sister is pretty pissed. She asking for the punishment we promised on our way here. You know, if you see someone naked, naked in front of the group.” “But dad,” Tad interrupted. “Let me finish. I need to talk to the other adults and just get a consensus. That punishment was meant for someone committing a bad act. This was an innocent mistake. Just let me see what they have to say.”

Tad just stayed in his cabin. He couldn’t face Katie or Winnie after seeing them naked. Truth be told, he didn’t even see anything. He was caught off guard and slammed the door so fast, all he really saw was a flurry of suit material. It was a little while before his dad came back.

The adults had gathered. They listened to Katie and Winnie explain what they perceived, then excused the girls. The moms were upset. Their little girls had been seen naked. It really didn’t matter why. They refused to back down. Their decision, since he already didn’t have swim trunks, he could just swim naked. He would spend the day naked and then his punishment would be over. The dads were unable to change their minds. They called a family meeting in the family space.

Tad, as if in repeat of his previous entrance, came in staring at the ground. He couldn’t look the girls in the face. Mr. Compton spoke up. “So, we explained the rules of punishment to everyone on the way here. Tad opened the girls’ door and saw them naked. As a punishment, he will spend the day swimming in the nude. In fact, he will stay nude for the rest of the day. The punishment is to begin immediately. Tad, I will take that shirt, those shorts, and your underwear. Should we go somewhere, you will be allowed to wear shoes or flip flops.” “But dad, this isn’t fair!” “Tell me why?” “Well, a few months ago, Brett opened the bathroom door and they all saw me naked and you all acted like it was no big deal. Seems like a double standard. Treat Tad one way and treat the girls another!” “Well, get used to it son. Now give me those clothes.”

Tad started crying. All the girls were shocked. They were going to get to see a real naked 14-year-old boy! Mrs. Compton started feeling bad again. She knew Tad was right. Once again, she felt like she should stop this, but she didn’t. Tad removed his shirt. Each step caused him to cry harder. He removed his shorts. He stopped at that point, unable to continue. His father reached forward and swiped his underwear down to his ankles and had him step out of them. Tad covered with his hands. Mrs. Walker started to say something. Mr. Compton stopped her.

Tad, I know you want to cover up, and that is fine for now, but you will participate fully in the activities we have planned and you will have to stop covering up at some point. If it goes on for long, I will make you stop covering or you will end up with more naked days. As it is, you will remain nude until bedtime tonight.” Tad, understanding the inevitable, turned to walk to the back of the boat and then removed his hands. The women and girls were expecting him to have to stand there on display. They seemed upset that they didn’t get their performance.

The little girls jumped up and ran to get another look at Tad, the other girls were right behind them. Mr. Compton had a warning for them all. “Any touching, harassing comments, or bullying, and you will join him in being naked. The girls slowed their assault but did not stop. As they were rushing to the back of the boat, Katie, not thinking about what she was saying, commented to Winnie “Good thing I left his suit at home!” Winnie drew in a gasp of air.

Tad was sitting on the swim platform putting on his mask and fins. As soon as he was ready, he was in the water. The girls rushed to get ready and pursue him. They couldn’t have cared less about the fish, turtles, any of it. They wanted to see his package. Mr. Compton told the others how wrong this was. “Just wait ‘til one of the girls does something and they have to get naked, then we’ll see where you really stand.” Then he walked off. The women knew he was right.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 5 - Tad’s Escape and Surprise

Tad was a good swimmer. With fins on, he was gone like a bullet. The girls never stood a chance of catching up to him until he started to return to the boat. Tad swam around and actually took some time to check out the fish. Every so often he would look up to see where the girls were. He would then duck under water and swim away. He was headed for the caves.

As he swam, he was curious, so he put his thumb on the top of his snorkel and ducked his head down. Looking back, he saw his cock just drifting along, moving with the water. It looked kind of weird seeing himself naked, in the water, out in public. He felt freer for some reason. He felt a little happier at being naked. Maybe he could get through this. He reached back and just lightly fondled himself. He wasn’t erect by any means. Far from it. The water was cool enough, his flaccid dick had retracked some back into his body, but he still felt aroused mentally. He tried to take a breath. He realized he still had his other hand over his snorkel and it was underwater. He popped his head up and was brought back to reality. He swam on.

He was swimming looking down at the fish, breathing through his snorkel. He had been so caught up in looking behind him, that he failed to notice the boats moored just up ahead of him. He was swimming and watching a school of blue and yellow fish when movement caught his attention just ahead of him.

At the exact same time he and a girl stopped just before colliding and surfaced. ‘Oh god!’ Tad thought. It was a girl from his class at school. Angie. He had heard from another girl that Angie had a thing for him. He pulled his snorkel out of his mouth and blurted out in surprise, “Angie! What are you doing here?” Suddenly he snapped back to the fact that he was naked. Maybe she didn’t notice. The whole situation made him start feeling a tingle below. Angie pulled her snorkel out. “Hey Tad. SO, I hear your family is responsible for my parents changing our summer plans.”

Just then another girl surfaced next to Angie. She seemed a little frantic. She ripped her snorkel out and tried to whisper in Angie’s ear “Oh my god! He’s naked!” She said it a little loud then ducked back underwater. Tad heard her as well. Angie still had her mask on. She ducked under water really quick before Tad could cover up. He was already at half-mast and rising. Tad tried to clamp a hand over his cock while he was treading water.

Angie resurfaced. She spit out her snorkel. Almost laughing and in shock, she said “Tad! Your naked! I saw your dick!” Tad was quickly sporting a full boner. He started to say something, but Angie dove back under water. She pulled the hand he was trying to cover with away to get a better look. Her friend Sarah was already underwater taking photos with her camera. She got the whole package and now he was sporting a raging hard on.

Tad didn’t know what to do, so he just turned and swam away as fast as he could. Sarah got a few more photos as he swam away with his rudder plunging down into the water. The girls could not keep up with him. Tad’s group had been told to be back before lunch anyway, so Tad started for the boat. By this time, the girls were all quite a way away from the boat, so he swam wide and avoided them and was able to climb on board without too much fanfare. Mrs. Walker had gone snorkeling, his mom stayed on the boat.

As Tad climbed on board, she turned and saw him. Tad saw his mom a few seconds later. He went to cover. “Tad, please don’t do that. It just makes me feel worse and you know you have to uncover at some point. I don’t know how we got here, but I promise this vacation will get better at some point.” “That’s easy for you to say. You not the one standing here naked. You’re not the one all the pure and innocent little girls are rushing to get a view of. You’re not the one being punished for a simple mistake, and I didn’t even see anything. And, you’re not the one whose mom was joking with all the girls about his boner! Plus, now some girls from school have pictures of me naked!”

Now Mrs. Compton really felt guilty. Maybe there was something to the double standard that she didn’t realize she was enforcing. Meanwhile, Winnie had not gone swimming either. She walked out just then to see Tad standing there facing his mom, not covering up. She saw everything. Tad saw her a moment later and covered up. He was still mostly erect.

Winnie walked over to Mrs. Compton. “Mrs. C, Uh, I don’t know how to tell you this, but as they were heading into the water, Katie told me she left Tad’s swimsuit at home on purpose.” Mrs. Compton had a look of surprise on her face. This could be really bad she thought. Her husband had decided not to go swimming and was up on the front deck downing a few beers. She headed over there.

Winnie turned to Tad, grabbed his elbows, reached up and kiss him. She hadn’t intended anything by grabbing his elbows except to steady herself, but as she stepped back from kissing him, Tad had moved his hands away and now she could see his boner. It quickly finished its rise to full mast. She put her hand to her mouth but still kept her eyes glued to his penis. He was circumcised and extended to a good 5 plus or so inches. She was impressed. She knew from health class that he would continue to grow as he went through puberty. She could only imagine how long he would get.

No one was around, so he took her hand and wrapped it around his shaft. She was startled, but proceeded to feel and move back and forth, and then felt his balls. She heard a noise and let go. Just then Mr. and Mrs. Compton bounded up the steps. The both were shocked to see an erect Tad standing there in front of Winnie. “This is so messed up!” Mr. Compton said. Tad, thinking he was talking about him and his boner spoke up, “What? I can’t help it!” Y’all did this…” With that he headed for his cabin. Winnie left for her cabin, but at the bottom of the stairs she turned around and went to Tad’s.

Mr. Compton looked at his wife. “You know Katie caused all this. You know what we have to do.” Mrs. Compton was trying to find a way out of this for her daughter. “We just can’t make our daughter strip naked, in front of everyone? You, Ben, Brett, and Tad?” she said, her voice cracking. “You had no problem making your son strip naked and his was a mistake, not on purpose.” “It’s different for boys! Girls are more sensitive, more modest. This is something girls don’t get over!” “Do you hear yourself? Tad was right, you do wield a double standard.” Mrs. Compton started to tear up at the thought of making her daughter strip. “And you get to tell her” Mr. Compton added. “I’m thinking about letting Tad get dressed!”

True to her Prurient interests, Mrs. Compton replied “Well, he still saw the girls naked, that was what the punishment was for.” (She remembered that Tad had told her he didn’t even see anything.) “I don’t know who you are” Mr. Compton replied. He went to get a couple of more beers and head back up to the front deck.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 6 - Facing the music

Meanwhile, in Tads room, they had locked the door after Winnie entered. Tad had Winnie sit next to him. He guided her hand to his cock. “It feels really good if you stroke up and down. Winnie started stroking. What a week. She got saved by a prince, got to see him naked, got to hold his cock, and now she was stroking him. She worked her hand up and down. Tad was prompting her to go faster. She sped up. He was getting short of breath. Winnie asked if he was OK. “More than OK, don’t stop!” She kept going. Suddenly he tightened his muscle and pushed his pelvis out and started to shoot. Winnie freaked and pulled her hand back. “Don’t stop!” Tad whispered forcefully. Winnie grabbed his cock and continued as he shot stream after stream until it was just dribbling out. Tad relaxed and then fell back on the bed. Winnie just sat there trying to take it all in. This was a lot for a 14-year-old girl to process in a short number of hours.

“We better clean this up. Everyone will be back in a minute and come looking for us.” Winnie said as she started looking around. Tad grabbed a roll of toilet paper Brett had snagged and put in their room. He started wiping up the floor. Winnie started wiping his now deflating penis. Tad chuckled. “I don’t know how you can do this. I would just die” Winnie said, the thought trailing off. “Well, I never thought someone as pretty and smart as you would go for a guy like me. I never thought I would get to kiss you, and I sure never thought you would give me a hand job!” “I just gave you a hand job? Wow… You think I’m pretty?” she said, switching from thought to thought. “Are you kidding? You’re the prettiest girl in school, hell, prettiest anywhere!” “I could get used to this. No one ever tells me I’m pretty. No even talks to me that much. I think they’re afraid to talk to me.”

They finished cleaning up. Winnie left first and went to her cabin. A little while later, Mrs. Compton made her way to Tad’s cabin. “Tad, honey, you need to come have some lunch. Remember your father said you needed to fully participate!” Tad checked himself, stood, and opened his door. She did her compulsory look at his crotch, “good, you took care of that” indicating his limp penis. “Uh, yea. Can’t run around with it sticking up all the time.” He replied, blushing “Look, if it gets to be a little much, its ok if you need to go to the bathroom or here and take care of it from time to time, like you did now. You look more relaxed.” His mom said nervously. She never imagined having a conversation about her son’s erections and standing there talking to him while he was naked. “Oh, I know I will have to take care of it. You sure it’s OK if I do it JUST like I did right now.” Mrs. Compton shook her head and headed back to the family area not actually knowing that he meant letting Winnie take care of it…

Tad made his entrance. The room got quiet at first, as everyone stared at the naked boy. He was no longer covering up or swimming away from them. Then the chatter started, and it got a lot louder. Tad got his food and headed up to the front deck. There were only 4 bean bag chairs. He took 1, Winnie took one, Mr. Compton was already there with his beer. Unknowing of the fate that awaited her, Katie took the other one, enjoying her brother’s embarrassment and enjoying looking at a penis some more. The little girls all piled out and sat on the trampoline, staring right at Tad’s crotch.

“So, Katie Poo, how are we today?” her father asked. “What do you mean dad?” she replied. “Well, I mean, is the day going as you planned?” “Dad, what do you mean? Of course, it’s not going how I planned. I planned on my summer being at home with my friends. Although there have been some interesting things going on here!” she answered. “Well, I’m glad you think it’s interesting. You know what I find interesting?” he said, setting her up. “What daddy?” Time to drop the hammer, “I find it interesting that we put you in charge of swimsuits, and then suddenly Tad doesn’t have one. And then you change in your room and you don’t lock the door. You always lock the door. Isn’t that interesting? It’s almost like you expected someone to open the door, isn’t it?”

By this time Katie was starting to get nervous. She was contemplating what to do. Should she run, hide? How long could she get away with that? She started tearing up, knowing where this was headed. Truth be told, it was actually an accident that she forgot to lock the door. She no longer was eating her food. She set her plate down. All but the four of them were not even paying attention. They were staring at Tad’s penis. “We are going to have a family meeting after lunch to discuss this further honey. I just want you to think about what you did. Why don’t you spend a few minutes in your cabin alone, instead of staring at naked Tad, your prize, naked Tad, OK?”

Katie quietly and somberly got up and went to her cabin. She laid down on her pillow and suddenly the water works started. Meanwhile, Mr. Compton explained what was going on to Tad. How Katie had purposely left his suit at home and then bragged to Winnie about it after he was made to strip. “What do you think about all this son? Because so far, I think you have gotten screwed-over on this vacation, and I’m sure not having the fun I planned on either.”

Tad didn’t reply right away. He thought for a moment. “Dad, I don’t like how all this came about, especially how us boys are being treated differently than the girls. It’s like they get 9 lives before they get in trouble, and I started out in trouble and almost have to fight my way out of it. But even then, I am glad that I got to kiss Winnie, and I am glad that I think we are going to be boyfriend and girlfriend. I’m not sure why, but I like being naked around her. So, this vacation is the best thing that could have happened to me in a totally unfair way. I don’t really like all the predators sitting there staring at me while pretending to be innocent little girls.”

“Well, we are not sure what is to happen with Katie. She caused you to have to get naked, so by rule, she should have to join you naked. I can’t believe my kids are going through this. This is shit that happens to other people, not to us. Pardon my curse words.”

“Dad, Katie would be devastated having to get naked in front of everybody. She might not ever talk to you again, or me for all that matter. I don’t think you should do that to her. It was my fault. Like you said, I shouldn’t have opened her door. If you have to impose punishment, then do what you have to do, but not because you think I deserve revenge. I wouldn’t do that to my sister.”

Winnie grabbed his head, wrenched it around and kissed him. “Where can we find more boys like you!” she said. “Well, son, I will be meeting with the adults and they will decide, but I am proud how well you have handled this and how mature you are and protective of the ladies around you. I’d be furious. I would want more than revenge.” With that, Mr. Compton got up and went to get a fresh beer and talk to the other adults. Tad just sat there while Winnie rubbed his chest and the little girls sat and stared. Suddenly, Tad was feeling those familiar feelings. He had to have Winnie stop. She playfully kept rubbing and Tad ended up getting a boner, right in front of the little girls.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 7 - Impromptu Lesson

Mrs. Compton had been in the kitchen watching everything. She couldn’t hear, but she could see. She saw that Tad was getting hard again. She quickly headed up front. It was time for the talk and a demonstration in front of all the girls.

“Ok girls… Scoot a little closer. It’s time for a talk about boys. Tad, could you stand for me. To keep you from getting too distracted, let’s start with the back side. Tad turn around. OK, so you all know this is a butt. It is a little wider than your legs for sitting and cushioning your body. Boys butts tend to be more proportionate to their bodies than girls. Girls have wider hips for giving birth to babies. Tad flex your shoulders. See how strong his upper back is. Boys are geared more to strength than girls are. We are both built for different purposes. “

“OK, Tad turn around.” With that all the girls clapped. Tad had relaxed a little and was now only semi erect. “Girls, you will notice that he has a lot more muscles on his chest than a girl. Girls of course have breasts that enlarge as they grow, unlike boys. Tad has started growing little hairs on his chest. It’s not very visible yet but will start to darken and get longer as he gets older. The part you all want to talk about, his penis. Boys are born with a skin that covers the end of their penis. Many parents have it removed when the boys are babies. Tad, can you push some skin forward to make it look like you aren’t circumcised?”

Tad grabbed the skin on his cock and slid it as far forward as he could. It felt stupid to him and the girls giggled. “That’s good, you can let go now.” His skin moved back into its normal position. “A boy pees out of this hole here.” With that she grabbed his penis with 2 fingers and pointed at his pee hole. “It is also used for making babies. When a boy and girl get married, they have what we call sex or intercourse. The boy will get excited. Tad, can you help me out here?” Tad looked at her like she was crazy, he wasn’t going to masturbate in front of these little girls. Besides, he was already having a semi on his way to a boner with the discussion and her touching it.

Mrs. Compton started to reach, when Winnie interceded. “Here, let me help” and she grabbed his cock. Mrs. Compton was momentarily shocked. She took a gasp of air. A girl had a hold of her son’s cock right in front of her. Winnie started stroking and it wasn’t but a few seconds and Tad was hard as a rock. Mrs. Compton looked at Winnie, not knowing what to say. ‘How did we get here’ Mrs. C said to herself. All the girls had gotten quiet staring at this now ‘huge’ (to them) erection.

“This, girls, is an erection. When a boy gets erect like this, he can put his penis in his wife’s vagina and they will have sex for a little bit, then he will ejaculate or shoot his semen into her vagina. The sperm swim up to the cervix which picks up the sperm and if she has an egg, fertilizes the egg. 9 months later, they have a baby. Many boys and girls start playing at having sex as teenagers before they are married and end up making a baby before they are ready. It is always better to wait.”

“Any questions?” “Her own daughter Amy spoke up, “So that thing is supposed to fit inside us?” She said that with a disbelieving look on her face. “Yes dear, when you are older, it will be able to fit. Any other questions?” “He has sea men inside him?” the other 10-year-old asked. “No dear, it’s called semen. Its spelled s-e-m-e-n. It’s a whitish fluid that comes out after he is excited and stimulated.” “Can we see that?” she added. “Uh, well, I… um…”

Winnie to the rescue. She didn’t hesitate. She grabbed Tad’s cock, started stroking, and then looked at Mrs. Compton as if for permission. Mrs. Compton shrugged as if to indicate it was OK. Truth is, she wasn’t sure what to say. Winnie proceeded to give Tad his second hand job of the day. She had already done it once, so she was better this time. She stroked with one hand and fondled his balls with the other. In no time he was shooting his wad. Mr. Compton walked out just as Tad was ejaculating and saw Winnie stroking his son. He blurted out “Oh my god!” then turned and left.

“OK, I need a little helper to go get some paper towels and clean this up?” Amy raised her hand first and jumped up. She ran and got the towels. She started wiping the semen up and then grabbed Tad’s cock and started wiping. “Oh my” said Mrs. Compton seeing her youngest daughter’s hand on her son’s still mostly erect cock. Amy wiped up the semen, then smelled it. She rubbed some with her finger, then tasted it. She spit it out.

Mrs. Compton laughed. “Ok, girls, that’s all for now. Let’s try not to bug Tad too much while he recovers from our little demonstration. The girls let out a collective sigh of disappointment, then some started to walk off. A couple sat there and kept staring. Mrs. Compton headed back to the kitchen area. She poured herself a rather full glass of wine. Winnie grabbed Tad’s arm and pulled. “Come on” she said, then led him back towards his cabin.

When they arrived at his cabin, Winnie turned and locked the door. Tad wasn’t sure what was going on. He was thinking she was maybe going to play with his dick some more. ‘A blow job?’ he thought. He was standing next to her when she pushed him back on the bed. He fell backwards and landed leaning back on his elbows. He kind of pushed his hips forward presenting his cock which she was constantly looking at. Winnie did not meet his expectation.

“So, we’re a thing now, and I know you have been put through a lot. I keep feeling like you have been so great so far and I just thought you should get a reward. ‘Now are you going to…’ He didn’t even finish the thought when Winnie reached back and undid her Bikini top. Tad was shocked. Winnie pulled the straps forward but was holding the cups in place with her other arm. She wasn’t a 100% sure about this. She looked down and saw his boner growing. She pulled the top forward and down, showing her chest to Tad.

Tad’s eyes were sticking out of his head. Winnie didn’t have the largest breasts in their class, but he thought they were perfect. He was hard again. He sat up, bringing him closer to her. Winnie stepped back a half step. She hadn’t planned on any contact. Tad reached out and took her hands. “You are so beautiful! I can’t believe I’m getting to see this!” I could just…” He didn’t finish. Winnie was thrilled at his words and decided to continue. She wasn’t sure before, but she was now. She pulled her hands free and in 1 quick motion, pulled her bikini bottoms down and kicked then to the side. Tad almost orgasmed right then.

“Oh my god Winnie! Oh, I love you, but… Thank you!” Winnie stepped forward and took Tad’s hands and placed them on her breasts. Her nipples were hard as a rock. Tad wasn’t sure what he was supposed to do, so he just started massage them gently. He flattened his hands and rubbed her nipples with his palms. Winnie was quivering. This felt so good for her and she was climbing that mountain. Tad stretched and put a nipple in his mouth. Winnie shook unexpectedly. Tad thought he did something wrong. He pulled back as Winnie reached down and rubbed her clitoris to continue the orgasm she was having. When it got to be too much to keep rubbing, she clamped her thighs together and then pulled her hand away. She spun and let herself drop onto the bed.

Tad had an even better view of her hot little tinder box. He just stared at first. Then, thinking about the fact that she had previously reached out and grabbed his cock with out asking, he thought it would be OK to reach out and touch her most private area. He started at her landing strip of pubic hair. Like most girls she knew, she trimmed so that nothing showed in the skimpy bikini, but also liked it trimmed on the sides. He moved down and gently rubbed over her beautiful lips. Winnie shuddered and almost had to move his hands away.

Instead, she slowly opened her legs, giving Tad an even better view. He took this as an invitation to explore. He started to slide his finger in between her labia. Winnie slammed her legs closed. Tad sensed that he needed to stop. He leaned back and kissed her. Winnie kissed back, then stood and pulled on her bottoms.

Tad resisted the urge to grab his throbbing cock and masturbate. Winnie saw him place his hand right next to it, but not grab it. She put her top back on. Next, she sat back down and grabbed his cock. “I ‘m sorry, I can’t go too fast. I’ve never…” She let her voice trail off. “Its perfectly fine!” Tad told her. “It was awesome. You are so beautiful. Thank you!” “Thank You!” Winnie said. That was the best orgasm I ever had! It’s never felt like that before. It still feels tingly!” She said as she reached down with her free hand to touch herself while still rubbing his cock.

Bang, Bang, Bang! Came the surprise knock on the door.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 8 - Katie’s Moment of Reckoning

They hadn’t heard the handle rattle as they were entranced with each other. “Winnie, are you in there?” Katie asked. Winnie stood, unlocked the door, and let Katie in. Katie entered and was drawn straight to Tad’s erect cock. She let out a gasp. This was definitely taking a while to get used to. “Where were you, I look everywhere for you.” Katie asked. “Well, I just wanted to get Tad away from all the gawking eyes.

“Oh, I can see what you just…” Katie let the accusation sit for a moment. “So, what did you need?” Katie asked. “Well, I just wanted to talk to you” Katie replied. She was worried about later and possibly having to strip. She also hadn’t been able to talk to her about Tad and his nakedness. It was definitely a topic all girls want to chatter about. Tad for his part, sat there with a shit eating grin on his face and kept his legs open so the two girls could stare-away at his throbbing cock. Winnie gave Tad a kiss on the cheek, then leaned down and gave him a kiss on the head of his cock. Both Katie and Tad were caught off guard by that. Winnie stood and grabbed Katie’s hand. She was dragging her out of the room. Katie spun her head around to look at Tad’s cock one more time before allowing herself to be dragged to the girls’ room.

Tad relaxed and fell back on the bed with his hands behind his head. He was lost in his thoughts when he slowly dozed off to sleep. He didn’t even think about the fact that his door was open and he still had a hard on, laying exposed to the door for anyone passing by. Of course, no one would just ‘pass by’. His room was in the corner down the stairs. You would have to intend to be going there to stumble on the view he was providing.

Back in the girls’ room, Katie was both excited and scared. “OMG, I can’t believe we are seeing his penis all day!” Katie said. Winnie stared at her with a concerned look. She was talking about Winnie’s new boyfriend here and her own brother. Winnie found herself a little offended (or jealous) at the thought now, that all the girls are getting to see him naked. “Well, I know all the girls have learned a lot!” Winnie added, not knowing what else to say. “Uh, Yea! With you giving him a hand job and all. That was like, off the charts! I can’t believe mom let that happen. And then Amy took hold of his cock! Innocent little Amy!” Katie added. “Well, not so innocent anymore!” Winnie relied, and both girls laughed.

“So, what about what your Dad said?” Winnie asked. Katie started tearing up. “I just can’t be forced to strip in front of everyone. I can’t stay naked all day. There’s no way they would do that, would they?” Katie asked in fear. Winnie tried to console her. “Well, your brother, who you caused to have to get naked in front of all of us, pleaded with your dad not to make you strip naked.” “He did, He what… why would he…” Katie had trouble understanding why her brother wasn’t mad and didn’t jump at the chance to see her naked.

“Look, he told your dad he didn’t think you could handle it and not to do this if it was to get Tad some revenge.” Katie was shocked. She would have never done that for her brother. In fact, she didn’t. Why would he do that for her. She was scared but felt a different feeling for her brother. He really cared about her. She didn’t know what to say. “Well,” Winnie added, “I heard the adults go off to talk, so you will know the fate soon enough. I hope they just give you a spanking. That will be much easier for you. You might be embarrassed to be in your underwear, but its just like being in a bikini, hell, it covers more than a bikini!” Katie looked at her, nodded, but was working out all the thoughts running through her head.

Soon enough, everyone was summoned to the main area for a family meeting. Everyone came in and took a seat, even naked Tad. Of course, he was the main focus for most of the people in the room. All the ladies and girls were soaking up as many views of his cock as they could. He sat on the floor and crossed his shins, but then laid his hands over his cock as if to say ‘stop!’

Mrs. Compton, having been told by her husband that she had to MC the conversation, spoke up. “So, we called this family meeting to discuss a very serious issue. It seems that Katie had planned to try to get Tad naked by leaving his swim suit at home, on purpose. This led to the events that resulted in Tad going to see Katie to try to find his swimsuit, and seeing the girls while they were undressed. In addition, Katie left her door unlocked, which she never does. This seems to show that she wanted him to get a glimpse of them changing so he would get into trouble.”

Katie at this point had tears rolling down her face and had her head down, embarrassed. They didn’t have all the facts right, but mostly. Surprisingly, Tad too was crying. He felt bad for his sister. He had always felt like he needed to protect her, even if she was a pain in the ass. Mr. Compton and a few others had looked over at Tad when he was mentioned, and saw his tears.

Mrs. Compton continued, “It has been discussed, and we had previously agreed that if you cause someone to be seen naked, you would have to get naked too. So, Katie, you need to get up, stand in the middle of the room, and remove your cloths. As she said this, Mrs. Compton had tears running down her cheeks as well. Katie didn’t move, she went from tears to openly sobbing. Mr. Compton, incensed by the absurdity of the whole thing, yelled “NOW!”

Katie slowly stood. She was hesitant to move. Suddenly she felt a push from the side. Tad had stood and pushed his way past her. He went to the middle of the room, naked and all. “I don’t know if you all are right about what she did or what she thought. I know you were wrong about the accusations against me. You can’t make her strip. Not in front of everyone. It’s too much!”

Mr. Compton interrupted. “Son, this needs to happen if we are going to follow the rules we set. If someone causes someone else to get naked, then someone has to serve that punishment. It’s been decided. We can’t go back on that. It would mean that you kids wouldn’t feel like we would follow through on any of our rules and punishments. As bad as it sounds for Katie, the punishment stands.

“Well, then I will serve her punishment for her” Tad announced. Brett jumped in. He was all too eager to see Katie naked. “But your already naked” Brett announced, as if no one knew. Tad was quick with a reply, “Well then you step up as a gentleman and offer to serve her punishment!” Brett lowered his head. He had no plans to let everyone see him naked. Winnie offered an alternative for her friend Katie. “Tad could serve it tomorrow. He certainly didn’t want to get naked for us today. I’m sure he is looking forward to getting his clothes back tomorrow. He could serve an extra day and the punishment will be fulfilled.”

Mr. Compton was intrigued by the offer. He was conflicted because he thought Tad had gotten a raw deal. He also didn’t forget that everyone had seen him naked already, so he was over the initial embarrassment. It would mean his little girl wouldn’t be scarred, maybe for life, by having to strip in front of everyone. “Look, Winnie. I know you females like seeing naked boys” he threw a disapproving glance towards the ladies, “But Katie wouldn’t serve any punishment and would be rewarded with getting to see her naked brother for another day.”

Tad, with tears rolling down his face, not wanting his sister to be treated like that spoke up again, “I don’t care if its unfair. This whole thing is unfair! But I don’t want my sister to have to go through this!” Tad stopped. Everyone was anticipating him saying something, but he had nothing else. Winnie jumped back in. “Maybe Tad can serve her punishment if he chooses to, and Katie can get a spanking, so she doesn’t get off Scott free. That seems like a fairer punishment anyway. “

The adults were looking at each other considering this. Mr. Compton didn’t want his baby girl to get stripped in front of everyone, the ladies didn’t want a girl to be exposed to the boys and men (even though they had no problem enjoying naked Tad). Mr. Compton spoke up, “We’ll be right back.” He got up and indicated for the other adults to follow him. The went downstairs again to one of the adult’s bedrooms.

After some discussion, they re-entered. Mrs. Compton resumed her duties as MC. So, it has been decided that we will grant Tad’s request that he can serve Katie’s naked day Tomorrow.” The girls were all excited at the prospect of seeing more of naked boy. “It was also decided that Katie should not get off scott free. She will receive the spanking, and Tad will give it to her. If we feel he was too lenient on her, I will repeat the spanking to make sure she learns something from this. Katie ran and hugged her brother.

Mrs. Compton handed the paddle to Tad and offered him her seat. He sat down. Katie was nervous but this would be some much better than stripping naked in front of everyone. Still, she just stood there. Mrs. Compton prompted her, “Katie” and she indicated for her to get prepared and into the position. She was wearing just her bikini top and shorts over her underwear. She dropped her pants. She had changed out of her thong so she wouldn’t get into trouble for bringing that. She kneeled down to go over Tad’s lap. He was now mostly erect, so his penis was sticking up. She wasn’t sure what to do. Mrs. Compton just pushed her forward so she sort of fell on his lap, pushing his hard on down. It was lodged against her stomach.

Tad, fully aware that this was going from bad to worse for him, wanted to get this over with. He couldn’t figure out why he got hard hearing that he was going to spank his sister. Mrs. Compton, indicating he should start, said “12 Tad. And they better be firm.” She blushed at saying firm, right after having seen his hard on. Tad swung the paddle and made contact with the cotton covered butt cheek. It was firm but not his best. Katie’s body shifted forward at the contact and, at the surprise at how much it stung, she started to cry immediately.

Mrs. Compton wanted her daughter to feel remorse for the way she planned this out. Even though she and the other females were enjoying Tad’s exposure, she did not want her daughter to become a calculating bully. “That was a little light Tad. If I need to take over, just let me know.” Tad knew this meant he needed to get into it more. He also couldn’t help feeling the sensation of his cock rubbing on her stomach. It was both a turn on and wrong at the same time. He swung again, harder. Katie lurched forward and started bawling while Tad was feeling her stomach slide along his cock.

‘Smack!’ A third stroke. Katie was trying to move her hands down to rub her but. Tad had her left arm trapped up against him. He moved his left arm from her side to grab her arm and hold it. ‘Smack!’ Tad was now getting into the groove of spanking her, but he also felt sorry for her. He was riding an emotional roller coaster. He was rubbing his cock on his sister’s stomach and both enjoying and regretting spanking her. ‘Smack!’

Tad administered the 12 spankings. By now, he was ignoring the pleasure of rubbing on her stomach. In fact, he had lost his erection. He was openly crying. Katie stood bawling. Her ass was on fire. She was rubbing her butt furiously. Tad stood and hugged her while they both cried. ‘What a tender moment’, thought Mr. Compton. ‘A wronged boy, crying and hugging his sister after having to spank her while standing there naked because of her.’ ‘Irony’, he thought.

Winnie grabbed Katie’s shorts, grabbed her arm, and rushed her to their room. Tad sat back down, crying. All eyes in the room were now back on him, which was normal, for today anyway. Mr. Compton spoke up. “Tad” he said, “I know this has been unfair for you. I know you didn’t deserve this situation. I can tell it bothered you to spank your sister, but you know this also means you will be naked for another day.

“I know dad. It’s OK, I can do the punishment easier than she could.” He wiped the tears from his eyes. With a sobbing voice he added “but I can’t do that ever again.” His mother ran over and hugged him. “OK” Mrs. Compton announced, “shows over. You all can go do something else, somewhere else…” She wanted Tad to not be the center of so much attention. The adults left the room. Brett left the room. The little girls just sat there. “Go on. Go do something” Mrs. Compton told them. They left too.

“Tad, I am so sorry you had to deal with that. I love you so much. I can’t believe how much you have protected the girls!” She stopped, not knowing what to add. “Can I just go to my room?” he asked. “Sure”, and Mrs. Compton helped him stand up. She helped lead him towards the stairs to his room. He really didn’t need the help and sort of pushed away from her. He went to his room and closed the door. He fell on the bed and was openly sobbing. He couldn’t believe how much he hurt his sister.

In their room, Winnie had gotten a wet towel and some cream for the pain. Katie took off her underwear and held the towel to it. She had stopped crying openly and was sniffling in between breaths. Eventually she asked Katie to rub some of the cream on her red butt. Winnie did as she asked. It felt weird to Winnie to be rubbing her friend’s ass. It felt weird for Katie too. At one point they looked at each other and broke out in a laugh, with Katie trying to laugh and sniffle at the same time.

Finally, Katie took the towel and wiped the cream off. She got dressed. She had a million thoughts running through her head. She SO owed her brother. She knew she probably deserved everything she got AND everything he got. Her brother could not be elevated any higher in her mind. He was her saint, her savior. She rushed over to his room. Even though the door was unlocked, and she hadn’t knocked before… ever… she knocked. Tad answered. “Go away!” he announced for whoever was disturbing him. “I need to talk to you” Katie announced.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 9 - Katie Makes Amends

Tad quickly opened the door. “I am so sorry.” He was now crying again as he hugged her. “Its OK. I’ll be fine in a while. You had to do that. But you didn’t have to take my punishment. I don’t know how to tell how grateful I am that I don’t have to get naked. I can’t believe you didn’t want to see me naked. Especially after I left..” Tad put his hand over her mouth. She was rambling.

“I couldn’t bear to see you embarrassed like that. Its not a fair punishment. And I can’t believe they made me spank you. I used to think it would be fun to spank you and feel superior to you, but… It wasn’t fun.” He was crying again. Katie hugged him again. They sat on the bed. Neither was saying anything. They didn’t know what to say. Katie also couldn’t help herself. She kept looking down at his penis.

“Stop already” he said. “I can’t help it. I don’t know why but my brain just keeps making me look down” She said. Tad grabbed the covers and slid them over his lap. “Better?” he said. They both laughed. “Look” Katie said. “Its been fun seeing a naked boy. It was great watching and learning all that stuff earlier. And let’s not forget, you got a girlfriend, a hand job, and you seem to like parading naked in front of everyone.”

“OK, I will admit, I never thought I had a chance at being Winnie’s boyfriend. And yes, I did enjoy the hand jobs she’s given me” Katie interrupted, “Hand jobs? There’s been more?” “Stop” Tad said. “I don’t know why, but I do like having all the girls look at me. I don’t get that kind of attention, ever. And its also good that no one has said anything humiliating and comment on how immature I look or anything. I even freaked when I saw the girls from our class earlier while I was snorkeling. They saw me naked too. Oh my god! And they have pictures. Anyway, it was thrilling and scary. I don’t know what to think, but I am kind of enjoying it, especially since I don’t have a choice, so I can’t chicken out.”

“Well, I am no expert, but you do not look immature. I… We all think you have a nice cock, uh penis…” Katie was stumbling over her words. “I think it has worked out good for you in a weird way. I am sorry for leaving your trunks at home”. Katie looked down again, this time at the tenting blanket. Tad slid his hands over his erecting cock. Katie stood to leave.

“Thank you!’ she said. As she reached for the door, she paused, then turned the lock. She turned. Quickly, so she wouldn’t lose her nerve, she removed her bikini top. She undid her shorts and let them fall. She paused again, then grabbed her panties and slid them to the floor. She stepped one foot out of them and stood there on full display, with her feet about shoulder width apart. Her nipples immediately went hard. So did Tad’s penis. Katie stood there for a moment nervous. She didn’t know where to look. She folded her arms across her stomach. She had one hand up messing with her face.

Tad was in shock. He had not expected to see his sister naked. “Wow!” he said. “What does that mean, Wow?” She asked. “Well, you are very pretty. And I can’t believe you let me see you naked. I… I’m..“ Katie reached down and put her panties back on. She pulled up her shorts and snapped them. She looked into Tad’s eyes. He was not looking at her face. She paused for a moment, then grabbed her top and put it on. “Please don’t tell anybody” she said as she unlocked the door and opened it. “Well, I have to tell Winnie. I don’t want any secrets from her.” “OK” Katie said and then left, running almost like a gazelle, prancing, light on her feet. She had gotten a thrill from stripping for her brother. It was exciting and scary at the same time.

Tad closed the door and locked it. He needed to get some relief. He had been hard multiple times and now he saw his sister naked. It was overwhelming him. He started to masturbate. There was a knock on the door. “Who is it?” he asked. “Its me, Winnie” was the reply. He stopped what he was doing and opened the door. As all the girls have been doing, the second she entered, Winnie looked straight at his cock.

“So, I am just so proud of you. You are the best brother and the best boyfriend. I can’t believe what you did for your sister. And I can’t believe your want to be naked for another day!” Tad gave her a strange look. “I don’t want to be naked for another day. At least not all the time. I like being naked with you, but I don’t like everyone always staring at me, at my dick.” Winnie involuntarily looked down at it. “See, even you can’t stop looking at it. I can’t believe how obsessed you girls are. “

“You mean if one of the girls was naked, you wouldn’t look at their boobs or their… thing… every chance you got?” “Pussy, its their pussy” Tad replied, almost laughing. “I don’t like that word.” Well you haven’t had a problem with dick, cock, penis.” Tad replied. “Well, I don’t have one of those.” She was kind of embarrassed at how immature she thought that sounded, that she could openly use any word to describe boy parts but was embarrassed to use words that describe girl parts. They both heard noises outside and the boat moved a little. They weren’t sure what it was, but they ignored it.

Winnie reached over and started stroking Tad. “I’m not sure why you haven’t taken care of that. I think it would drive me crazy to be that horny.” “Well, I, uh..” “What?” Winnie asked. “I was actually about to when you showed up. But I would rather spend time with you than jerk off.” “Well, maybe I can help with that.” Winnie leaned down and took his cock into her mouth. Tad let out a gasp. The look on his face was priceless. She really had no idea what to do, but he didn’t know that.

She sucked him off for a good two minutes. He couldn’t last any longer. He had been trying to make it last as long as he could. “Win, I’m about to…” She sped up. She had heard about swallowing a boy’s load from girls at school in the locker room. Tad tensed up, thrust his hips forward and shot his strongest orgasm ever. Winnie gagged a little on the juice flooding into her mouth. She couldn’t figure out how to swallow with his cock still in her mouth. She just kept going. Sperm was oozing out the corners of her mouth. Finally, she needed to breath and swallow. She pulled back as the last eruption fired softly in her face.

“Oh my god, I’m sorry” Tad pleaded. Winnie, swallowed. Took a deep breath. Swallowed some more. “Its OK” she said as she was wiping his cum off her face and into her mouth. It didn’t really taste good, but it wasn’t too bad. It was a taste she hadn’t expected. She didn’t know what to expect, but she wanted to seem like she knew what she was doing.

There was a knock at the door. Thinking they were done, Winnie opened the door. Mrs. Compton was standing there. “We, uh, have some guests. You might want to stay in your room a bit.” Tad looked out the curtain. The boat from the caves was now moored next to them. They had also tied up to another boat in between the two of them, essentially making 3 boats into 1 long boat. Tad panicked. It was the girls from his class at school. Two of them had seen him naked, even taken a photo. Tad had a look of fear on his face. Maybe he really didn’t like always running around naked.

“Oh, and Winnie, you have sone stuff right there.” And Mrs. Compton put her finger to her own face to indicate her right cheek. Winnie slid her finger over it and collected some more cum. Winnie’s and Tad’s eyes got big as saucers. It wasn’t a lot, but it was obvious and now Mrs. Compton knew. Mrs. Compton turned and left smiling. Winnie looked at Tad and they both started laughing. She put her finger in her mouth and cleaned it.

“What are you going to do?” Winnie asked. “Well, I am going to hide out as long as I can. Maybe I can eat dinner in my room.” Tad replied. “You mean you don’t want to show off your big ol’ dick for all the new girls?” Winnie said, half joking, half serious and jealous. “Are you kidding me?” I don’t want them to see me, naked. And I don’t want to be the talk of school when we get back. And that one girl has pictures of me naked in the water! With a boner!”

About that time, Mr. Compton showed up. “Tad, I know you probably want to be scarce right now. I know I would. But its almost dinner time, and you will be joining us up top side. You know the rules, full participation. Sorry buddy.” “But mom said I might want to stay in my cabin for a bit. I thought I might eat dinner here.” Mr. Compton shook his head no. “You know the rules.” With that, Mr. Compton left. He had been compelled by the other ladies to speak to Tad. They still wanted to see some naked flesh, even at Tad’s expense. Tad and Winnie just stayed there not knowing what to do.

Soon it was dinner time. Brett showed up. “Hey, uh, I need to change, and Tad, your on the duty roster to help with dinner. Y’all need to vacate.” Tad looked at Winnie with fear in his eyes. “Winnie, could you take my turn?” Tad asked. “Uh, she’s on the duty roster too. You both are. Mr. C said to get a move on.” Brett tried to usher them out of the room. Once in the hallway, Brett locked the door to change. Tad, for some strange reason, was getting hard again. “That happens a lot doesn’t it?” Winnie asked. “You have no idea” Tad said.

They weren’t sure what to do. They were just standing there when they heard footsteps. Down the stairs came 2 of the 10-year-old girls and the girls Tad saw earlier. “Oh, uh, we were just giving them the tour” Amy said, as they all stared at Tads rising boner. “Hi Tad” Angie said, “It’s so nice to see you again.” They had been hoping to find him and see him naked. The families had been warned about the rules and punishment they had instituted and Tad’s current predicament. The other families told everyone that the same rules would apply to them.

They all just stood there for a few minutes not knowing what to do. Tad’s erection was so hard, it was twitching with every heartbeat. Winnie was looking at the girls’ faces and then at Tad, then down to his cock. Suddenly Mr. Compton appeared behind the girls. “Tad, kitchen duty” he said. Tad started walking to the stairs, his fate sealed. The girls made room for him but did not move out of the way. As he passed Angie, she grabbed his cock. Winnie slapped her hand. “What the hell” Angie said. “Oh, wait until I tell the adults what you just did!” Now Angie was worried. She wasn’t sure how all the rules applied.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 10 - Facing the Music, Again

Tad walked up on deck. He would have thought he was at a Hawaiian Tropic photo shoot. There were so many girls in bikinis, he almost fainted. Every head turned as he walked out, fully erect. Hands went to mouths, comments “Oh my!” “He really is naked!” “Look, he has a boner!”. Apparently, the cheerleading squads had arranged to do their vacation together, and it looked like they were almost all here. There was a mysterious lack of boys in the crowd. Tad hurried over to the sink. He faced away from the crowd. “What do I need to do?” he said with a crack in his voice. “Well, you can start by peeling the potatoes” was Mrs. Walker’s reply as she was staring at his cock.

Winnie walked over to Mr. Compton. “Sir, when we were coming up the stairs, uh, Angie reached over and grabbed Tad’s penis. She was saying things and trying to humiliate him. Mr. Compton just stood there. ‘Not again’ he thought. Winnie went to join the crew in the kitchen. She tried to stay between Tad and all the girls who were straining to get a look. Some of them had left reluctantly, as there was cooking being done on all three boats. Mr. Compton walked over to the parents on the next boat to discuss Angie’s actions.

Angie’s parents for their part, were shocked. They hadn’t actually gone over to the Compton’s & Walker’s boat, nor had they seen the naked teen boy. Truth be told, they thought it couldn’t really be true. Who would do that, and with all the girls around? When they heard their sweet little angel had grabbed the boy’s penis, they were beside themselves. They tried several reasons to excuse her behavior. When it came down to it, Mr. Compton told them “You know what you have to do.” Then he walked back to his own boat.

Meanwhile, all the girls from all three boats were crowded, staring at the Compton’s boat to watch Tad as he was forced to parade around naked. Mrs. Compton noticed this ‘herd behavior’. She started thinking maybe there was a double standard. She was just glad she was on the female end of it. She went back to working in the kitchen and stealing glances at her naked and still erect son.

Dinner was cooked. To limit the crowdedness on the Compton’s boat, It was decided that the adults would dine on the Stillwater’s boat, the teen girls would dine on the Taylor’s boat, the one in the middle with all the cheerleaders, and the rest of the kids and the boys would dine on the Compton’s boat. The teen girls still watched to see if Tad ate inside or on the front. When he chose the front of the boat, they chose the front of their boat.

Mr. Compton made an observation to the group of adults. “So, it seems none of the females will get anything done with a naked boy running around. They all gravitate there and then just constantly stare. Don’t they get enough? You would think they would get more used to it and not let it dominate their thoughts.” Mrs. Taylor spoke up. “Well, lets see how preoccupied you guys get when you make Angie strip. I still can’t believe we are even allowing that. Girls should not be punished that way.”

“Well, your daughter did grab the boy’s equipment. No one made her do it. And we had just gotten through having the talk with them. It just shows, the teenage mind cannot control itself, male or female” Mr. Compton added. “Well, your boy seems to be OK with it all” Mrs. Taylor snapped. “Oh, don’t kid yourself. He had no desired to strip on this trip. Hell, he didn’t even want to be swimming without his shirt on. Now he’s being forced to parade naked in front of all his classmates, who will, after this trip is over, tease him at school and anytime they see him the rest of the summer. He didn’t even want to come out of his room for supper. I made him, because we have to enforce the rules.” “Hmmph” replied Mrs. Taylor.

When dinner was finished, those on the clean up duty roster did the post meal chores. It was some of the girls, Brett, and a few dads. The cook never has clean-up duties after a meal. Tad went to hide in his cabin. The girls were all disappointed when he left. They were goading Brett to get naked for them. Brett turned a dark shade of red. His behavior on this trip had been exemplary minus the 1^st day when he wrote on Tad’s forehead. Truth is, he could not imagine being forced to get naked. A few of the girls were in his class and he would be so embarrassed for people to find out he was still in the early stages of puberty.

Games were on the agenda for the evening. Tad was told by his dad that he had to participate. He came out of hiding. He hung out in the corner of the family area where the table provided him some cover. The group split up. The girls had fought to sit near Tad. Winnie had flanked him on one side, and Katie on the other. They were doing what they could to protect him from the predators. One of the really cute girls, Jennifer, leaned in as close as she could and told Tad that some of them were going to go for a midnight swim. They might even do it with less clothes than normal.

Winnie and Katie also heard her. They both gave her a nasty look and then as they were turning back, taking their customary look at Tad’s cock, noticed that he was getting hard again. Apparently, the idea of seeing naked cheerleaders turned him on. This should not have been a surprise, but the girls were upset, especially Winnie. She wanted him to only have eyes for her. She elbowed him to show her disapproval. The other girls kept stealing glances and the ones sitting on the floor just openly stared at his cock under the table, as it rose to full mast. They would never tire of seeing that.

After playing for a few hours, Tad told the group that he had been playing with that he was heading off to bed. As he got up, he was still hard as a rock. Some of the girls guessed that he was going to go play with himself to relieve the pressure from all the excitement. “Do you want me to come with you?” Winnie asked. “I don’t know. I was thinking it might be nice to be alone for a little while. You know, no one gawking at my… at me.” “Oh, OK” Winnie replied in disappointment. She was looking forward to more intimate contact.

Tad worked his way through the crowd of girls. He had to step over some of them on the floor which was awkward. He headed down the steps to his room. When he got there, the door was locked. He knocked. After about 30 seconds, Brett answered and let him in. “What are you doing dude?” Tad asked. “What do you think numb nuts? Cheerleaders everywhere. Bikinis. They keep asking to see me naked. I had to rub one out.” “Dude… spare me the details” Tad told him. Tad dropped onto the bed and pulled the covers over himself. It was the most he was able to cover himself all day.

Just then the head cheerleader, Nancy, came into their room, without knocking. ‘Damn, I should have locked that door’ Tad thought to himself. Nancy made herself at home. She sat down on the foot of Tad’s bed. She put her hand on his ankle and started rubbing her thumb over it. Tad tried to pull his ankle up and stop the contact. Nancy tightened her grip. “Don’t be like that” she said. I’m just being friendly.

Tad did not want to chance upsetting Winnie, especially with a witness, Brett, there. “I know what you were just. You girls all act offended when a guy flashes you for his own enjoyment and then when someone has no choice, the true you comes out. Your all fighting to get another look and try to get your hands on the goods. Why can’t I get a little peace and quiet!” Nancy paused. She wasn’t sure what to say or if she should be mad. Then she replied.

“You know, when some guy or old man flashes us, its doesn’t feel safe. Yes, we want to see, but we want to feel safe and we don’t want people to judge us as pervs. This shit right now, you running around with a ‘stiffie’ cause your being punished, that’s safe and we know if we ALL act interested, no one can single us out as pervs. People are born wired to want to see the opposite sex. I can’t believe you are surprised. Maybe you’re not surprised, you just don’t like being treated as a sex object like us girls are.”

“Don’t give me that. You girls wear clothes showing so much of the ‘goods’ and do all that make up and stuff because you want to be looked at. Your all trying to be the sexiest one, so why wouldn’t we think of it in a sexual way. If y’all would admit your just like us, maybe worse, this shit wouldn’t be so hard”

They both had good points. There was a brief tensioned silence in the room. Tad had started relaxing before Nancy entered but this surge of adrenaline had him back to rock hard. His erection was tenting the blanket and it was obvious. Nancy lunged forward and grabbed his cock along with the blanket that was around it. “Give it to me! Give it to me!” she started almost yelling, acting like a zombie.

Tad didn’t stop her. He was under the covers, so this wasn’t his fault and he did like girls handling his cock. He was playing with fire here, but his brain was spinning a hundred miles per hour. Brett was sitting on his bed up in the corner with his covers pulled up to his chest, quietly watching all this. Nancy started trying to reach under the covers with her other hand and to get to his cock. She repeated her request. “Give it to me naked boy. I need some dick!” She wasn’t sure they could tell she was over doing it, but she was having fun and hoping to hold a dick in her hand too.

Brett was thinking ‘come grab my dick!’ He undid his zipper under the covers, and pulled out his didck. He started to stroke himself gently under the covers. He fantasized about girls, even cheerleaders craving his cock. He closed his eyes and listened, pretending Nancy was talking to him. Both Nancy and Tad noticed what Brett was doing. Tad looked at Nancy and shrugged his head towards Brett indicating for her to attack him. Nancy stared back and adamantly pointed at Tad’s blanket covered cock. Tad shook his head no.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 11 - Brett’s Fantasy Comes True

Nancy withdrew from attacking Tad and turned towards Brett. She played it up, “I’m gonna get that cock if it’s the last thing I do!” she said. Brett, with his eyes still closed and still fantasizing that she was talking to him, sped up his motion. Nancy slid her hands up under the covers, making sure not to touch Brett yet. She was ready to pounce. Suddenly she lurched forward and grabbed Brett’s balls in one hand and his hand that was wrapped around his cock in the other. She could tell it wasn’t going to be as huge as Tad’s. She looked over at Tad with a frown.

Brett in the meantime was startled. His natural reaction was to reach up and pull the covers tight to his neck. This gave Nancy the opportunity to grab his now free cock. Brett had a deer in the headlights loo on his face.

“Hey there big boy” she said to Brett from under the covers. Brett just sat there with a shocked look on his face. Here was his fantasy coming true, but he did not know how to react. “You like me touching you?” she asked as she started stroking him. Brett reacted, quickly shaking his head yes. “Then get naked, now!” she demanded. Brett looked over at Tad then back at Nancy. HE quickly reached under the covers and removed his shorts and underwear, finishing by kicking them off. He sat up and pulled his shirt over his head, then pulled the covers back up.

“Uh, Uh, Uh! We lose these” she said as she started pulling the sheet away. Brett let go. She unveiled his cock. She looked over at Tad. She tried to say it so she wouldn’t embarrass Brett, “if I have to settle for this, you gotta at least let me look at yours while I’m doing it.” Tad shook his head no. Brett, not wanting this to end, spoke up. “Dude, you’re not really allowed to cover up, remember?” Tad slowly slid the covers down to reveal his engorged cock. Nancy wanted to pounce on it but continued to stroke Brett.

She could tell he wasn’t going to last long. Brett was squirming, almost as if every sensation was over stimulating him. Staring at Tad’s cock, she took Bret into her mouth and started sucking while still stroking him with a couple of fingers. Tad had never watched someone else get a hand job or a blow job before. He was feeling sexually charged too. He stared at Nancy as she sucked Brett off and started stroking his cock at the same time. Nancy was turned on even more and sped up while staring at Tad’s cock.

Brett didn’t last long. He erupted in Nancy’s mouth. She was intently staring at Tad and swallowing. Brett was finished. It didn’t take long for him to be overstimulated to the point he couldn’t stand it. Nancy kept going. Tad closed his eyes and pretended it was Winnie sucking him off. He went faster and faster and then raised his hips off the bed. As he erupted, Nancy launched herself and grabbed his dick away from him and went straight into her mouth. Some of his spunk had already landed on her face. Tad, caught in the moment just let go and put his hand on the back of her head. She sucked him dry.

It was one of Tad’s best orgasms. He looked like he had the ‘O’ from ‘OH NO’ permanently stuck on his face. Nancy continued to stroke him to make sure he completely finished, then took one long sucking drag on his cock as she released it. She leaned down and licked his balls and then slid off the bed. She stuck her fingers in her mouth and sucked off any juices letting out a “mmmmm” with each one. She turned, unlocked the door, and exited.

Tad and Brett looked at each other. They were still naked and exposed but neither seemed to care after what they just experienced. They leaned towards each other and did a high five. Just then, Winnie walked in. She started giggling seeing Brett naked for the first time. “What’s going on here?” she asked. Both boys just laid there in the euphoria of an orgasm. “Ah, nothing…” Tad said. “Nothing hell!” Brett said, “the head cheerleader just sucked my dick!” The comment shocked Winnie. All kinds of thoughts were trying to enter her head. “What? Why would she…” She didn’t get to finish her question.

Brett excitedly started filling her in. “Nancy wanted Tad’s dick. He wouldn’t let her, so she sucked my dick instead! She even swallowed my cum and everything! Holy shit!” Winnie was shocked hearing this. She looked at Tad who shrugged and kind of nodded. “Yea, and pervo here jacked off while he watched.” Tad was afraid he was going to tell about Nancy jumping over and swallowing Tad’s cum as well, but Brett stopped.

“Uh, Brett, you know I can see your dick?” Winnie said, expecting him to cover up. Katie rounded the corner. Brett slowly slid the covers making sure Katie saw the goods. She started giggling. It wasn’t a shock seeing Tad since he had been naked all day, but Brett had always been super modest up until now. Then Brett responded to Winnie’s comment. “Hey, if girls are going to suck my dick, I will stay naked all the time!” Of course, he might change his mind later when he’s not riding the high.

Katie looked at Winnie as if to ask what Brett was talking about. “Well, apparently Nancy sucked Brett’s dick while porn star here jacked off. He was probably performing for her.” Katie was shocked. This would be useful information in her circle of friends later. “Did she suck your dick too?” Katie asked Tad. “What? No, how can somebody suck your dick while your jacking off?” Tad said coyly. “Wait, I can’t be having this conversation with my sister. Get out of here!” he demanded.

“Whatever. Mom wants you two up on deck now.” She and Winnie just stood there. They were waiting to see what Brett would do. Even though he had a smaller cock, it was still a cock. Brett started to get dressed. “She said now, just go!” Katie said. Tad got up worked his way to the door, squeezing passed Winnie and Katie. Winnie pushed into him so he had to rub his cock on her. Katie felt the push and pushed back getting his butt across her belly button. Brett continued to try to slide his pants and underwear on. With his hands preoccupied with his underwear, Katie pulled the sheet off of him. He was now exposed again. Both girls stared at his wilting dick which was getting embarrassingly small. Brett managed to get his underwear on as the girls started pulling his arms to get him out of bed. They weren’t told to get the boys no matter what state of dress they were in, but the girls thought it would be funny to embarrass Brett a little.

Brett in turn was going to play this a little to see where it would go. “You know, you two barged in here and saw me naked. No knocking, no permission. I could get you stripped for a whole day.” He had a smile on his face at the thought. “Well, mister, Winnie said while waving her pinkie, “The door was open when I walked in, and you admitted that Nancy just sucked you off in your room. I wonder who will be in trouble in that scenario? Us, or you and Nancy?” Brett grabbed his shorts so he could try to put them on as he was ushered up on deck.

As they arrived in the family area, Brett stopped kind of in the corner and put his shorts on while everyone watched. When he looked up, he turned red. “Next time you can finish dressing in your cabin, OK?” Mrs. Walker told her son. “Well, they, uh…, I mean…” “Just sit down. We need to go over some stuff” she replied. Brett took a seat.

Mr. Taylor started, “so, we went over some rules that had been established before we got here and we all agreed to follow them. Some of the rules had very dire consequences and that was intended to make sure no one broke those rules. Now, before we all got here, Tad had been accused of breaking a couple of those rules and as a result he got a spanking in his underpants, and as you all know, he was then forced to strip after entering a girl’s cabin without knocking and the girls were changing. He was required to remain nude the rest of the day as part of that punishment and ordered not to cover his private parts during his punishment.”

While he was speaking, Tad’s mom wanted to correct him about the spanking, but he didn’t leave room to butt in.

“Everyone was warned not to tease him and were also warned that there would be no touching. If someone was to openly tease someone being punished and we thought it was bad enough, they would be forced to join him, I mean them in their punishment. The same goes for touching. If someone touched them inappropriately, that person would also join him, they in their punishment. It was asked what would happen if it was almost the end of the day. Would the punishment be met or completed. We decided that if the punishment started before noon, it would have been completed by the time they go to bed. If it happened after noon, it would go until the same time it started but the next day.”

At this point a few girls were getting nervous. Truth be told, almost all the girls had groped him at one time or another, either while playing games, or during the sex talk. Winnie, Amy, Katie, Angie, Nancy, and few other girls were getting nervous. They knew they had all broken the rules.



Sailing the BVI (British Virgin Islands)

By Who Da Man



Chapter 12 - Tad saves the Girl…. Again

“Honey” he said, indicating for his wife to go next. “Well” Mrs. Taylor said with tears forming in her eyes, “it has come to our attention that to further embarrass Tad and sexually assault him…” She said that last part and looked at the men who insisted that it was an assault once they established that the women would have considered it an assault if one of the girls was naked and one of the boys touched her inappropriately. “That Tad had his, uh… member grabbed without consent and inappropriately. By the rules that were given, that person is required to join him in his punishment.” Mrs. Taylor now had tears running down her face.

“Angie dear, please come up here” her father said, as Mrs. Taylor could not continue. Angie started crying as she walked to the center of the room. “Honey, we had multiple witnesses confirm that you grabbed him almost immediately after getting on the boat.” Angie wrapped her arms around herself and was bawling. “You are going to have to remove your clothes honey” he continued. Angie turned and ran to her room. She locked herself in. She could not let this happen to her. Mr. Taylor followed her.

Winnie was both relieved and glad. Relieved that she was not implicated and glad that the girl that grabbed Winnie’s boyfriend’s cock was going to get humiliated. What was weird for her was, she also didn’t really want all the boys to see a naked girl. It was a strange conflict going on in her head. The other girls were relieved when they weren’t called up.

As the Taylors were trying to tend to the issue with their defiant daughter, Mr. Compton stepped to the middle of the floor. “So, I want to address a few issues too. We have had some things go on aboard the boat that are really crazy compared to normal. We really didn’t expect anyone to break the nudity rule. When Tad did it, it was an accident and sort of caused by Katies actions. Not sure he deserved to be humiliated like that and I let him know that. Some of you took advantage of the situation and made him into an anatomy lesson for the girls. There was some inappropriate touching and sexual activity that clearly breaks the rules”

The girls were all once again getting really nervous. “I want to set the record straight” he continued. “There will be no more of that. PERIOD. It was inappropriate and some of it was way inappropriate for minors. You Carol” he said indicating his wife, “Winnie, Amy, and all of you who were in the audience, later will apologize to Tad for embarrassing him like that and taking advantage of him during a time he was confused about what was OK and what was not.“

The girls let out a sigh of relief. “Any more of that, and you will all be running around naked for the rest of the trip!” That last part, no one had agreed to. Some of the women started to speak up, but their husbands stopped them. No one had any intentions of have a bunch of kids running around naked for a whole week. At this point Tad stepped into the middle. A place he seemed to be finding himself a lot. At least this time he wasn’t sporting a boner.

“Look, I don’t like what Angie did. I think she deserves a punishment. Probably deserves to be naked. I think this is getting carried away. Since I was the one she ‘assaulted’” he said using quotes with his fingers, “I think I should have some say in the punishment. I will give her the same spanking I gave Katie when she wasn’t forced to strip.” There were some surprised looks all around. No one had heard about that.

Mrs. Taylor clasped her hand to her face. She was overwhelmed at the idea that her daughter wouldn’t have to be embarrassed by being stripped in front of everyone. Mr. Compton agreed with Tad. He gave him the OK without even asking the other parents. Brett was a little upset. He wanted to see some naked female flesh. Tad, not knowing what else to do, went to Angie’s cabin where Mr. Taylor was still trying to get her to open the door. Mr. Taylor looked at Tad, surprised to see him there.

“Angie,” Tad said loudly, “ I told them I didn’t think it was fair to make you strip. If you want to avoid getting stripped for a whole day, you need to come out now and I am going to give you a spanking. Twelve whacks. Its gonna hurt, but it will go away. And it will be a little embarrassing because you have to be in your under pants for it, but its not as bad as what you were promised. I’m going back upstairs. You have 5 minutes to report in your underpants. Otherwise, you get to join the naked club.”

Tad headed back up the stairs to the family area. His mom had already moved the chair into place and got Tad a towel to put on his lap. Tad was glad for the towel. He did not want to end up rubbing Angie’s stomach like he had Winnie’s.

A few moments later, Mr. Taylor came upstairs. He said nothing. Everyone just stared wondering what was going to happen. Two minutes later Angie came up in her bikini bottoms and a t-shirt. “No, underpants!” Tad said authoritatively. Angie started crying a little harder and went to change. Everyone waited in silence. Angie reappeared in her panties. She walked over to Tad. She leaned down and hugged him and then apologized, then dropped to one knee, then the other. She laid over his lap and grabbed the legs of the chair. It seemed she was used to this procedure.

Tad did not want to prolong this. He started administering swats immediately. He almost seemed rushed. By the time he was at 6 he had tears streaming down his face again. Angie had started bawling after about 4 strokes. She took it like a pro. When Tad was finished Angie stood rubbing her butt and crying. She looked to her parents as if to ask what to do? Was she looking for a corner to stand in?

Tad stood, still crying, and gave her a hug. He made sure to keep the towel between them. “He whispered in her ear, “you can go now. With that she rushed back to her room. She had a really long cry. Not just from the pain, but the pressure of the whole situation. Mrs. Taylor had tried to follow her. As she passed Tad, she put her hand on his arm as if to say thank you. Tad turned and headed to his room. He was upset at himself. ‘Why was I crying?’ he thought, ‘and why do I have another boner?’

Tad was still lying on his bed when Brett started to enter about 5 minutes later. “Give me a few minutes bro” Tad said. Brett left quietly. He had acquired a newfound respect for Tad in the last couple of days. Tad finished his cry and reflecting on what happened. He stopped in the bathroom and washed his face. He came upstairs to get a drink. Of course, he had to do it naked. His punishment at this point wasn’t going to end until tomorrow night. He was also sort of getting used to it plus it was quite arousing at times.

When he entered the family area, Angie was waiting. She rushed and hugged him. He tried to lean forward so his junk wasn’t touching her. “I don’t know what to say! I am so sorry for being a nasty bitch and grabbing you. I’m sorry for not considering your feelings or the fact that you were suffering through embarrassment and I ignored all that. Can you ever forgive me?” She was tearing up again.

“All is forgiven. Can you forgive me for that spanking I gave you? I think I was mad and maybe I hit you too hard” he replied. “Oh, there’s nothing to forgive. I deserved that spanking and more. You saved me from being naked. I don’t know if I will ever be able to make it up to you.”

“Well, while we’re clearing the air, Winnie is my girlfriend. Deal with it. Stop constantly coming after me. I like you as a friend, a good friend, but its Winnie, got it?” He spoke so confidently and authoritatively. This was not the boy that boarded the boat a couple of days ago. Angie dropped her head slightly, “Yes sir. I got it. Thank you for being so nice to me.” Tad lifted her chin. “You’re a pretty girl. There are plenty of guys out there that would be lucky to have you for a girlfriend.” They both looked over. Brett was standing there. They glanced at him and then cracked up laughing. “What?” was all Brett could say.

It was getting late. The parents thought it might be a good idea for the kids to go to their cabins early after all that had happened. Some of the teens had talked about staying up all night. Others had mentioned the naked swim at midnight. Now they were all being shuffled to their cabins.