How Jacqui Saw Me Naked

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by MaireadM »

Great twist in the story and he has some hope.
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by steam train »

Another wonderful chapter. Very high quality writing, thank you. I doubt he has a chance of winning but there is certainly a great reward to strive for.
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by EverythingOff »

MaireadM wrote: Mon Oct 06, 2025 9:19 pm Great twist in the story and he has some hope.
Yes, he has hope. The question is: are you rooting for him to win, or would you rather see him lose???
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by Debbifan »

He has to lose, otherwise the story is in the wrong section ;)
My stories at CHYOA ( different username )
https://chyoa.com/story/Debbi%27s-Shame ... ures.14847
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by Freesub »

Debbifan wrote: Tue Oct 07, 2025 11:55 am He has to lose, otherwise the story is in the wrong section ;)
Not necessarily. He could always win now, and while he is busy enjoying his reward, end up agreeing to and losing the revenge bet, forcing him into getting naked for the other girls while Jacqui redresses.

In fact I would argue it would almost be too stereotypical if he was to lose just as the timer was about to run out.
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by EverythingOff »

Debbifan wrote: Tue Oct 07, 2025 11:55 am He has to lose, otherwise the story is in the wrong section ;)
That is an excellent point! :lol:
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by EverythingOff »

Freesub wrote: Tue Oct 07, 2025 12:10 pm In fact I would argue it would almost be too stereotypical if he was to lose just as the timer was about to run out.
That's a great point, actually. I suppose we'll find out how much of an ENM purist I am... or not! ;)
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by steam train »

EverythingOff wrote: Tue Oct 07, 2025 5:39 pm
Freesub wrote: Tue Oct 07, 2025 12:10 pm In fact I would argue it would almost be too stereotypical if he was to lose just as the timer was about to run out.
That's a great point, actually. I suppose we'll find out how much of an ENM purist I am... or not! ;)
I hope you’re not too much of a purist:) I have always enjoyed mixing things up a bit in a lot of my stories and Jacqui is certainly not your atypical story girl who has excessive modesty!
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Re: How Jacqui Saw Me Naked_New Oct. 6

Post by EverythingOff »

steam train wrote: Wed Oct 08, 2025 12:15 am I hope you’re not too much of a purist:) I have always enjoyed mixing things up a bit in a lot of my stories and Jacqui is certainly not your atypical story girl who has excessive modesty!
I plan to release the next chapter on Thursday, so we will find out then! I'm going back through one more time to see if there are any more opportunities for her to twist the screws a bit. :evil: :evil: :evil:
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How Jacqui Saw Me Naked: Chapter 5

Post by EverythingOff »

Chapter 5: Simon Says

I couldn't believe it. I'd actually agreed to play a naked game of Simon Says with my friend, Jacqui. If I won, I'd get my clothes back and I'd get to see her naked. But if I lost, I would have to stay naked all afternoon... and she might even invite over a couple of other girls to look at me. But she clearly laid out the rules, and I felt very confident I'd win.

I waited for the first command as I stood naked in front of Jacqui, carefully cupping my hands in front of me.

She wore her brightest smile. "Alright, James. Here... we... go! Simon says: stand on one foot."

I did it. This was a piece of cake. I'd have my clothes back in no time!

"Simon says: stand on the other foot."

I did it. I was still covering with my hands, but I was doing it and following her instructions.

She was shooting these rapid fire now.

"Simon says: jump three times."

I jumped three times.

"Jump two times."

I jumped two times.

"Simon didn't say!" she sang, grinning and reaching for the pad and making a little tick mark on it.

Okay. Okay. Simple mistake. I just needed to pay more attention. Head in the game... head in the game...

"Simon says: jump two times."

I jumped two times.

"Simon says: spin around."

Oh my god. She hadn't seen my butt yet. If I did a spin, she'd see it! But I knew I had to do it, or I'd get a penalty point, and I wouldn't get my clothes back or see her naked.

"Oops. Sorry, James. That's another penalty point. Remember, no stalling." She marked another tick on the pad.

"But..." then I cut myself off. I saw her raise an eyebrow at me, warning me to not talk back. And I sure didn't want another penalty point.

"Okay, James. I won't do a penalty point for that one, since you stopped yourself. But remember, no talking back. Now, back to the game. Oh, yes. Simon says: spin around." She was smiling so big. It was a genuine smile, too. Not just a teasing one. She was really having fun watching me make a fool out myself.

I didn't hesitate this time. I spun around. I kept my hands covering my front, and I spun as fast as I could so she wouldn't be able to stare at my butt.

When I finished my spin, she was smiling so big.

"Cute butt, James. We'll need to have a longer look at that! Haha! Plus, congratulations! Seems like you're starting to figure out how this game works! Only problem is..." and she looked at her paper... "you've already got four penalty points, and we're only about a minute and a half into the game. So you're going to really have to step it up. Do you think you can do that?"

I nodded enthusiastically. I really wanted to win. I'd do anything, no matter how humiliating. I wanted my clothes back and I wanted to see Jacqui naked. Plus, there was no way I was going to let her invite Christine, Tracy, or Laura to come over and see me like this. Oh my god. Never in a million years.

"Alright, James. Let's continue. Simon says: turn away from me and jump five times."

Jeez. Not only was she going to see my butt, she was going to see it bounce up and down! But okay. Here goes. I didn't hesitate. I turned away from her, still with my hands on my front, and I bounced. 1... 2... 3... 4... 5. Then I turned back around. Boy, was she happy. I don't know if I'd ever seen her smiling so big.

She was laughing a little. "Wow, James. Your butt's super cute when it bounces! I might need to give that command again later! In fact, let's see it right now. Simon says: turn away from me and jump five times." I had no choice but to do it. So I did, and she started laughing harder. "Oh my god, James! Again!!! Simon says: turn away from me and jump five times!" This was the worst. But I did it. And with each bounce, she started yelling, "Higher! Higher! Higher!" Boy, was she laughing. I could have done without that.

When I was done, I turned and faced her again. Her smirk really made me blush. But I didn't say anything.

"You're doing a great job of following instructions. Really. I think you might actually be seeing me naked soon! Here's hoping, right? Just stay focused! Okay. Let's get going. Simon says: touch your nose."

Still cupping with my left hand, I took my right hand and touched it to my nose.

"Simon says: touch your forehead."

Easy. I moved the same hand to my forehead, still covering in front.

"Simon says: cover your ears!"

She grinned a smug grin. She knew I had no choice now but to uncover and let her see my penis and balls. Otherwise, I'd get a penalty point. It was as embarrassing as anything, but hey. She'd seen it before, right? It was sort of hard, but not all the way. I got up all my courage and lifted both my hands and covered both my ears. Her eyes focused like a laser between my legs, and I saw her starting to laugh under her breath. She didn't want me to notice, but she was definitely laughing, and that was starting to make me hard.

"Oh my god, James. I just realized! This is the first time I'm seeing it since the exam room. Well, except for the peek down your shorts. But other than that, this is my first time really looking at it since the exam room."

And then she stopped talking and she just stared. She just stared and stared and stared. It felt like forever. I was frozen and my heart was pounding, knowing I was fully exposed in front of her.

Then she said, "This isn't part of the game, James, but move your thing out of the way. I want to get a better look at your balls."

"Not part of the game?"

"No. No penalty points. You can hesitate if you want. I think it's cute that you're shy and you like to hesitate. But when you're ready, move your thing out of the way. I want to see those cute little ballies."

Was she kidding? She wanted to see my "cute little ballies?" I just stood there, not knowing what to do. Then she started to get impatient.

"Okay, James. Move your thing already. I'm tired of waiting. Or if you want, I can just make it part of the Simon Says game, and then you'll have to do it."

"No, okay. I'll do it. I'll move it. That's okay."

I was nervous, but I moved it up and out of the way, and her eyes just zoomed in to look right at my balls.

"Wow." She actually seemed mesmerized by them. "They look so soft and smooth."

"Um, yeah." I was shaking.

"Come here. I need a better look." I hesitated. "Seriously, James. I'm not going to bite. Just come here."

I took a few steps toward her.

"Closer, please."

I took another step. She leaned way in. I thought I could almost feel her breath on my balls. She lifted her finger, and I thought she was going to touch them. That made me shiver a little. But she was just kind of pointing to them and examining them without saying anything.

Then she snapped out of it and said, "Okay. That's fine. You can step back now. Go back to your hands on your ears, and we'll pick up the game."

I stepped back and put my hands on my ears right away. I didn't want another penalty point. And my thing was really pointing straight out now, after she had been looking at it so close.

"Simon says: hop on one foot."

Oh my god, this was humiliating. Naked, with my hands on my ears, all hard and bouncing, hopping on one foot. But no choice. I did it.

"Hop on the other foot!" she commanded through her laughter.

I immediately switched feet and started hopping on the other foot.

"Oh, James. Simon didn't say!" And she marked another tick mark on her pad. But I didn't say anything. She made a mocking 'tsk tsk' sound at me, like she was saying, "Shame on you for not paying better attention." But I was ready for the next thing. Still covering my ears and awaiting her command.

"Simon says: get on the floor and crawl to the bookshelf and back."

This was really getting more humiliating by the second. But I figured, how much worse could she make it? So I didn't delay. I got down on my hands and knees and crawled over to the bookshelf and back.

"Simon says: stand up."

I did, covering again.

"Simon says: put your hands behind your back."

I did. It popped out. Mostly soft now. It was crazy how fast it kept getting hard and soft and hard and soft again. And she seemed to be enjoying the show.

"Simon says: grab your thing."

Oh my god. No! How could I do that in front of her??? Then I realized that I had hesitated! And she caught it right away.

"Oops, James. You stalled! Remember, no stalling." Then she snickered as she made another tick mark on the page.

"Look, James. I'd love nothing more than to give you your clothes back and let you see me naked, but you're going to have to start paying more attention. So let's try again. Simon says: grab your thing."

I immediately grabbed it with my right hand.

"Simon says: get yourself hard again."

No way!!! Was she kidding??? But I wasn't going to hesitate. I started playing with it. It didn't take long, and it was all hard again in seconds.

"Put your hands on your head and skip around the room."

I wasn't falling for it. She didn't say "Simon says." So I stayed put. She actually seemed impressed.

"Nice job, James! Maybe you'll win this thing after all. I bet you'd like that, wouldn't you? You'd get your clothes back, and you'd see me naked! So I'm rooting for you, I really am. Just keep paying attention. Now then, Simon says: Put your hands on your head and skip around the room."

This was certainly the most humiliating thing she had asked so far. But I did it. I immediately put both hands on the top of my head, and I started running around the whole perimeter of the room as fast as I could. I didn't want to take a chance that she would say I cut corners or something.

As I was running, she just kept staring at me. I think she said something like, "Look at it bounce, James! Look at it bounce! Oh my god! Does that hurt with it flopping around like that???" She was laughing pretty hard, and even thought I couldn't believe she was making me do this, I kept going. I was going to win!

It wasn't a long run, but my heart was pounding like I'd just sprinted 100 yards.

I came back to where I started, and put my hands back down to cover. I figured that was okay. It was like the neutral position, and she hadn't given me any penalty points for it so far, so I figured it was fine.

She looked at me, with this look of concern. "Hmm," she said.

"Hmm?" I repeated back.

She tapped the pen to her lips, like she was deep in thought. "Well, and maybe this was my mistake, so I won't give you a penalty point for it, but I had said to skip around the room, but you actually ran around the room. So no penalty point. Probably my mistake for not being clearer. But you know what skipping is, right?"

Oh my god. She was going to make me do it again? And running naked was bad enough. But to have to skip like a little kid?

"Um, yeah. I know what skipping is."

"Okay. So I'm going to need for you to do it again, but this time, you need to skip. You know. Like a little girl. Can you do that? Skip like a little girl?"

Why did she have to keep saying 'like a little girl'???

"Um, yeah, Jacqui. I can do that."

"Great!" She smiled a genuine smile, like she really wanted me to succeed. "But just to be safe, let's see you skip just over to the pool table and back, so I can make sure you're skipping properly. You can keep covering with your hands for now, if you want. I'm just looking for form."

Seriously??? But okay. I kept my hands cupped over my privates and started to skip over to the pool table. I saw her staring at me every step (or ever skip) of the way. She was wide eyed and smiling, especially once I got past her and she could see my butt. It was super embarrassing to have to skip naked like that, even while I was covering. Then I skipped back to my spot and stood there.

"How was that?" I asked.

She looked a little disappointed, and it wasn't even like she was teasing me. She genuinely looked disappointed. "Well, yeah, you were skipping. But I was hoping for a little more... I don't know... merriment in it. Seriously. Like a little girl holding her bookbag and lunchbox, skipping across the playground on the first day of school. Do you think you could do that? You know. Just a little more energy and enthusiasm? And maybe smile a little? Could you try that?"

Oh my god! This was insane!

"So I think you should do one more practice, just to make sure you get it right. Because if you do the whole thing and it's still not right, I'd have to give you another penalty point. And neither of us want that. I mean, I'm rooting for you to win. I really am. So just do another practice over to the pool table and back. You know. With some pep and energy and a smile. Maybe sing a little song or something."

"Sing a song???"

"Yeah. Like... um... oh I know! 'This is the way we go to school, go to school. go to school. This is the way we go to school so early in the morning!' Yes! Sing that and skip to the pool table and back! Whenever you're ready." She looked at me like she was directing a movie and it was time for another take.

On the bright side, at least she was letting me cover up. Because if I had to do this with my hands on my head with my thing bouncing around... oh my god.

"Any time now, James. Whenever you're ready. Peppy and with the song. And... go!"

I couldn't believe it, but I did it. Hands firmly over my privates, I started skipping over to the pool table, singing:

This is the way we go to school
Go to school
Go to school
This is the way we go to school so early in the morning!


I returned and waited for her approval. But she still looked unsatisfied.

She tapped her pen to her lips again, thinking. Then she perked up all of a sudden!

"I've got it! I know what's missing!"

And she ran to her closet and started rummaging around. She got down on her hands and knees, looking for something on the bottom shelf. And then she turned to me with two objects in her hand. Oh my god! She walked over and held them out for me.

"Here you go, James," she beamed. "Here's my backpack and lunchbox from when I was in kindergarten." She was so pleased with herself.

I just stared at the items. This wasn't happening!

"But Jacqui! This backpack has princesses all over it! Ariel and Rapunzel and Jasmine and Belle. And I don't even know who this one is!"

Without missing a beat, she said, "Merida."

"And that lunchbox? A Cinderella lunchbox???"

"Exactly!" she said with a broad smile. "Here, take them. Put on the backpack and hold the lunchbox. Then try skipping. I think that will really make it all come together!"

Then she flashed me a smirk. Then I knew. She really was out to humiliate me as bad as she could. My heart sank a little.

"Jacqui, come on. This is ridiculous. I can't do this! I won't!"

She took the backpack and lunchbox and started to head back to the closet to put them away. "That's fine, James. You don't have to do it. We don't have to keep playing Simon Says at all," she said flatly.

"We don't?" I was a little hopeful that she would just give me my clothes back.

"No, we don't. You can just forfeit. So I'll put the backpack and lunchbox away, and you can just forfeit." She tossed the lunchbox and backpack into the closet and closed the door. "There. All done. You can just forfeit."

"Does that mean I get my clothes back?"

She ran back to me, all excited. "No, silly. It means you forfeit, and we jump right to your penalties!"

"My penalties?"

"That's right. You stay naked all afternoon and I invite over Tracy, Christine, and Laura. That's what we agreed to at the beginning."

"No!" I shouted. I was stuck. "Okay, okay. Bring me the backpack and lunchbox. I'll do it, okay? Just don't have them come over!"

Boy, was Jacqui happy with this situation that she had created. I was just hers to embarrass and humiliate however she wanted, and she knew it.

"Great! I think you made the right decision, James. And I really do think you can win, and that you'll get to see me naked. I really think so!"

She trotted back to the closet and fetched the backpack and lunchbox.

"Here, put this on," she said, carefully wrapping the pink straps of the princess backpack over my arms and shoulders. "And hold this in your hand," she said, giving me the lunchbox. At least I could still cover my privates with my other hand.

She stepped back to look at her handiwork. "Oh, you're going to look great skipping around the room and singing! Just great!"

She looked at me again from a little further back. "Wait, hold on. Something's missing." She thought. "Oh, I know!!!"

And she ran back to her closet, once again rummaging through. Then she found something and ran back to me.

"Here! You can hold this in your other hand!"

"What is it?"

"It's a fairy wand! You know! You wave it and all your dreams come true!" Then she looked at me and waved the wand, saying, "I wish for James to skip around the room like a little girl on the way to school!" And then she burst out in a full-on belly laugh.

"Here, take the wand, James! Take it!" She continued laughing at me as I was forced to uncover with my other hand so I could hold the wand."

"There! You look amazing!" Doubled over laughing, she sat back down on the couch. "All naked with your princess backpack, fairy wand, and Cinderella lunchbox. Come here. Let's look in the mirror!"

She took me by the arm and dragged me into the bathroom, and I saw myself in the mirror. Oh my god!!!

"Don't you look adorable???" She was actually being really sweet. For real! Like she was in preschool and we were playing dress up!

"Jacqui!!!" Come on!!!"

Then she dragged me back out into the rec room and stood me in front of the couch.

"Okay, James. The game is back on. Simon says: Merrily skip around the room three times like a little school girl, singing the song we practiced."

I knew I had to go. If I delayed, I'd get another penalty point. So off I ran... or should I say, skipped.

This is the way we go to school
Go to school
Go to school
This is the way we go to school so early in the morning!


My penis was completely soft and my balls were bouncing with every skip. I looked over at Jacqui, and she was laughing her butt off.

I made it the first time around, and she called out, "This time, wave your wand a little more! Higher and in little circles! Like you're making a magic wish!!!"

And I did exactly what she said! I was singing that stupid song, smiling, and waving that ridiculous wand in little circles.

This is the way we go to school
Go to school
Go to school
This is the way we go to school so early in the morning!


Then she called out, "Third time! But this time louder, make bigger circles with the wand, and skip nice and high!

I was sure in it now. I just couldn't believe it. I was skipping and flopping and singing. I was so focused on what I was doing, I didn't even remember to be embarrassed about it. But believe me. As soon as I stopped after the third circle, I dropped everything I was holding, put my hands over myself, and turned bright red.

She looked at me with a grin and said, "That was great, James. Really, really great. I'm proud of you!"

I slipped out of the backpack and dropped it on the floor.

"You're a good boy, James. A really good boy. Now get on your knees and kiss my feet."

Oh my god. But I couldn't not do it. I immediately got on my knees and knee-walked over to her, and kissed her bare feet. They were really soft, actually, and I kind of liked it. But I wasn't going to say that, of course. And even though I was soft when I was skipping, as soon as I kissed her feet, I got totally hard again.

"Very nice, James. But you know what? Simon didn't say for you to kiss my feet!" She laughed and made another tick mark. That even made it more humiliating! She had totally tricked me! But I couldn't call her on it, because she'd give me another penalty point for talking back! Holy shit! I had gotten on my knees and kissed her feet for no reason!

"Now then, Simon says: Kiss my feet."

I bowed down and started kissing her feet. I kissed each foot very gently on the top. She had pretty feet. I guess I never noticed before. They were very small and very soft. I actually didn't mind doing that.

"Okay, James. Simon says: stand up and face me."

I did, covering again.

"You're doing great," she said, trying to reassure me. "Ready to go on?"

I nodded. I was pumped and ready. I was in it to win it!

"Simon says: tell the truth. Who would you be most embarrassed to be naked in front of? Laura, Christine, or Tracy? You have ten seconds to answer."

Oh my god. I was afraid to know what she was going to do with that information. I mean, it would be Laura, for sure. She lived right next door to me. We used to play together when we were really little. Like three years old. She'd come over and we'd play in the sprinklers together. And I don't remember it, but she even teases me sometimes that we used to run around the house naked back then! So I think that would be particularly embarrassing. Christine and Tracy, yeah, absolutely, it would be awful. But I think if Laura saw me, that would be the worst.

So I said, "Laura."

Jacqui seemed impressed that I answered. Then she smiled at me and said, "Simon says: say 'I want Laura to come over and see me naked.'"

Oh, no. It wasn't true, but she was making me say it. I couldn't get another penalty point. So I said it. "I want Laura to come over and see me naked."

Jacqui grinned at me. "That's great, James. So if you lose the game, that's who we'll invite over first. Sound good?"

"First...?"

"Well, of course. I mean, if you lose, we'll have to invite all three of them over. But we'll have Laura come over first. Unless you think it would be more fun to save the worst for last. What do you think?"

I didn't want to be accused of talking back. So I just stood there.

"Okay. Well, you haven't lost yet. So you might still pull it out." She looked at the clock. "Looks like we've got about three minutes left of the game, and you've got..." she counted up the marks on her paper... "Look at that. You've got seven penalty points. So you can afford to get two more. And if you can get through the next three minutes and just get two more penalty points, then you win! You get your clothes back, and I'll strip for you! Of course, if you get three more penalty points in the next three minutes, well, I think we both know what that means. Honestly, I'm fine either way. I would have stripped for you earlier, if you had simply told me that you wanted to see me naked. But you hesitated, and so you missed out. Because if you'd been honest, then you'd be dressed and I'd be naked right now. Do you realize that? I'd just be laying there all naked for your inspection. So always tell the truth, James. I think that's an important lesson from today, don't you think?"

I nodded. Wow. You have no idea how mad I was at myself for not saying I wanted to see her naked earlier. I mean, maybe she was just teasing me, and maybe she had no intention of stripping before. But at least there was a possibility!

"Alright, James. Three more minutes. Good luck."

I focused as hard as I could.

"Simon says: tell the truth. Do you like me?"

No hesitation. "Yes."

Then she clarified. "I don't mean do you 'like' me. I mean, Simon says: do you like like me?"

Oh my god. Yes, of course I did! I had such a crush on her. But it would be embarrassing enough to admit that in any situation... let alone while I was naked and at her mercy. I didn't know what to do.

"Ooohhh, too bad, James. You hesitated." With a wide grin, she made a tick mark. "One more penalty point." Oh my god!

Then she went on with the game.

"Simon says: stand on the pool table, spread your feet real far apart, put your hands over your eyes, and say, 'I love being naked for Jacqui!'"

This was almost too much. But I could only afford one more penalty point. So I ran over, climbed up on the pool table, I spread my feet, put my hands over my eyes, and said, "I love being naked for Jacqui." This was maybe the most humiliating thing she had made me do. Alright. Maybe not as bad as the skipping around the room. But this was really bad.

"Simon says: hold your pose."

I didn't move.

"Simon says, say it louder. 'I love being naked for Jacqui.'"

I maintained the pose, my penis now standing straight up. And I proclaimed, "I love being naked for Jacqui."

"Get down from the pool table."

I hopped down, but then I realized... oh no!!!

"Oops! Simon didn't say!" she beamed. And she made another tick mark on the page.

"Okay, James. Looks like that's nine tick marks. One more, and you'll be at ten. And if you get ten, you lose. Remember? And we just have one minute left in the game. So here comes the lightning round. Are you ready?"

I nodded. I was ready. I was so focused, I wasn't going to make a mistake. No matter how humiliating the task, there would be zero delay.

"Simon says: hands on your head."

I did it.

"Simon says: grab your thing with your right hand."

I did it.

"Simon says: cup your balls with your left hand."

I did it.

"Switch hands."

I held still. Simon didn't say. I had this! She gave me a nod of approval, like, "Good going, James!"

"Simon says: switch hands."

I switched, holding my penis in my left hand and cupping my balls with my right.

"Simon says: turn around and bend over like you're about to get a spanking."

Oh my god. But I did it.

"Simon says: stand up."

I did it.

"Simon says: say 'I want to see Jacqui naked.'"

No problem. "I want to see Jacqui naked."

Simon says: spank yourself two times.

I did it.

"Spank yourself one time."

I did it. OH NOOOOO!!!!!

Jacqui was all smiles. "Simon didn't saaaaayyyy!!!!"

Oh my god oh my god oh my god!

She made one final tick mark on the page, and held it up proudly so I could see it. Like she was smugly showing off an "A+" on a spelling test or something.

My heart sank. The game was over. I had lost.

"James," she said, "don't be sad. Really, I think this is best. Trust me. It'll be fun. But you know what this means, right?"

"Jacqui! Come on. This isn't fair!" I literally kneeled down in front of her, naked and begging at her feet. "Please. That's fine. I'll stay naked for you. Whatever you want. Anything! I'll even put on the princess backpack and skip around the room all afternoon! But please! Please don't let Laura come over and see me like this!"

She was having way too much fun teasing me. And I was praying it was all just teasing and that she wouldn't really invite Laura over.

"Can't we just keep it just us? Please?" I was literally begging, naked on my knees in front of her.

"But James, you lost the game. I mean, if you had won, I was going to get naked for you. So there needed to be a penalty, too. And that was the penalty. I told you right from the beginning. I said, 'Here's what you get if you win, and here's what happens if you lose,' and you still agreed to play the game. You could have said that you didn't want to play."

"I didn't know that was an option!"

"Well, it's always an option, right? But since you agreed, played, and lost, that's what happens. You're so silly, James. But I'll tell you what, to make it fair. We can go downstairs and shoot free throws. First person to make five in a row, wins. If you win, just Laura comes over. But if I win, I text all three of them—Laura, Tracy, and Christine—to all come over. What do you say?"

"But Jacqui! You know you're better at free throws than me."

"Yup. I know," she smirked. "But it's my rules. So that's the deal. Do you want to try or not? Oh, and you'll have to go out there naked. I'm not giving you your clothes back."

"Jacqui!!!"

"Fine. Have it your way," she teased. We'll just have Laura come over. We'll save Christine and Tracy for later. Now get up off the floor and go into the bathroom and grab a towel."

"Grab a towel?"

"Yes. Grab a towel and wrap it around yourself. I can't have Laura coming over and seeing you naked right away. Wasn't that your whole fantasy? That you want her to strip you? And how can she strip you if you're already naked? So go on. Go get a towel and wrap yourself up."

Resigned, I headed for the bathroom. Then I heard her call, "Oh, James! I think there's a princess towel in the closet. I want you to use that one. Not up for discussion. After all, you look so cute in pink!" She laughed out loud.

"And while you 'get ready', I'll text Laura to come over."

This wasn't happening... this wasn't happening...
Last edited by EverythingOff on Thu Oct 09, 2025 9:07 pm, edited 2 times in total.
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