Naked in Front of Jenny (New 11/9)

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
EverythingOff
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Naked in Front of Jenny (New 11/9)

Post by EverythingOff »

The following is applicable to all chapters of “Naked in Front of Jenny:”

This is a work of fiction and is pure fantasy. Names, characters, places, and incidents are products of the author’s imagination and are used fictitiously. Any resemblance to actual events, locales, or persons, living or dead, is entirely coincidental.

For ages 18 and older only.

Part 1
Part 2

* * * * *

Naked in Front of Jenny - Part 1

When I was in fifth grade (11 years old), there was a girl who moved to our school in the middle of the school year. We'll call her "Jenny." I thought she was the prettiest girl I'd ever seen. She had blonde hair in a sort of bob, with piercing blue eyes and a cream-colored complexion. And I was so lucky because she had been assigned the desk right next to mine.

We hit it off right away. We'd spend recess together and we'd joke around a lot.

Then one night I had a dream about her. I don't remember the dream, but it was my first "romantic feelings" dream. Maybe we were kissing in the dream. I don't really remember. But when I woke up, I was absolutely head-over-heels in love with her. Absolutely my first crush ever. I don't know if she felt the same way about me—in fact, I'm quite sure she didn't. I'm pretty sure she just liked me as a friend. And that was okay with me. At least it gave me plenty of opportunities to be around her and spend time with her.

One Saturday over the summer between fifth and sixth grade, we were riding bikes together. We were both 11. We rode back to her house. It was a hot and sweaty day, so we took off our shoes and socks, and left them by the garage door. Then we went to the kitchen for lunch. Jenny opened a couple of cans of Spaghettios and we sat in the kitchen and ate them, right out of the can. I remember watching her eat. She was radiant.

Then her dog ran in. It was a small dog, but I was nervous around dogs. I tried to be brave, but when the dog started jumping on me, I jumped back, and my can of Spaghettios fell all into my lap, covering my shorts completely. After the initial surprise, Jenny started laughing at me as she went to get some paper towels, making fun of my fear of a tiny dog, making fun of my clumsiness, and making fun of how ridiculous I looked with the Spaghettios all over my shorts. And, of course, to make matters worse, her dog started licking the Spaghettios off of me, which only added to Jenny's amusement—and my ridicule.

She gave me the paper towels and I started to clean off. That's when her mom came in.

She took one look at me and told Jenny to run to her brother Nate's room and get another pair of shorts for me to wear. He was a couple of years older than me. Meanwhile, Jenny's mom brought me into the laundry room and she told me to take off my shorts. I really didn't want to take off my shorts in front of her, but I didn't feel I could talk back. I didn't want to be rude, and, after all, I had made a mess not only on myself, but also all over the kitchen floor. So I felt bad, and didn't feel I was in a position to argue. At least Jenny wasn't in the room.

So I started to pull down my shorts, and as I did it, more of the Spaghettios started to fall on the floor, which was clearly irritating Jenny's mom. She wasn't mean about it, but not wanting another mess to have to clean up, she took matters into her own hands. She curled up the bottoms of my shorts to catch any of the falling Spaghettios, and she slowly and carefully pulled my shorts down, telling me to step out of them. So I was now in the laundry room in just my shirt and underwear. Jenny's mom had her back to the window, and I was facing away from her, so I was looking out into the kitchen.

Just then, I heard Jenny's footsteps coming down the hall and into the kitchen. I started to panic. I knew she was about to see me in just my shirt and underwear.

And then it happened. Jenny turned the corner and saw me. And I will never forget her face in a million years. Her eyes went so wide and she literally started laughing. She laughed quietly because she didn't want to get in trouble with her mom, but she was absolutely laughing. I turned bright red. But what could I do?

I watched Jenny's eyes look me over, looking at my naked legs, and checking out my little white briefs. My heart started beating so fast. I couldn't believe it was happening. Literally, I couldn't believe it.

Jenny was holding a pair of Nate's shorts and she took her time bringing them over to me, with this devilish smirk on her face. She held them out and said, "Here you go." I was about to grab them and quickly put them on, hoping to end this embarrassment as quickly as possible. But her mom snatched the shorts out of her hand and sat them on top of the washing machine. To this day, I can still remember Jenny's eyes looking at me, as I looked longingly at the shorts that could save my modesty, but they were out of reach. She was really enjoying the moment. I don't know if she cared about seeing me in my underwear, but she sure was enjoying seeing me all embarrassed like that.

Still facing away from Jenny's mom, she told me to turn toward her. She looked at my shirt and noticed that I had sauce stains all over the bottom part of my shirt, too. Jenny was now standing right next to her mom, so I was facing both of them. And with zero warning, Jenny's mom lifted my shirt right off of me, pulling it over my chest and maneuvering my arms and hands to strip off my shirt. Again, Jenny's eyes went wider than ever. At first, she kind of gasped and put her hand over her mouth, but it quickly turned into a smile that literally went from ear to ear. Her entire face lit up, seeing me standing there, now in absolutely nothing but my little white briefs.

It was probably three seconds, but it felt like a lifetime.

Jenny's mom told her to run up to Nate's room again, and this time grab a t-shirt for me. Jenny took her time leaving, and the whole time she did, she had her eyes trained on my body, just looking it up and down, from my bare feet up to my face, and everything in between—with a big grin on her face the whole time. Her mom, of course was oblivious, focused primarily on trying to keep her floor clean. So Jenny ran to Nate's room. And she was going fast. I think she wanted to get back to the laundry room before I'd have time to cover up with anything.

At this point, I'm still in nothing but my white briefs, and Jenny's mom is rinsing the Spaghettios off my clothes into the laudry sink, in prepartion for putting my clothes into the wash. And meanwhile, I'm just standing there in my underwear, nervous about Jenny returning. I remember thinking about asking for a towel or something to cover with, but I was shy and didn't want to be rude to Jenny's mom. Again, she didn't seem upset about any of this. Maybe a bit annoyed. But she was just trying to handle the situation as effectively as she could.

Of course, in pops Jenny, all smiles, holding one of Nate's t-shirts. I was about to grab it from her and put it on. I figured I could at least pull it down over my underwear until I was allowed to put on Nate's shorts. But just as I reached for the shirt, Jenny's mom snatched it from Jenny, and sat it on top of the shorts.

I was standing there, looking longingly at those shorts and t-shirt, knowing it would save me from this embarrassing torture. And of course, I'm not saying a word the whole time. Not like there was anything I could have said, anyway.

Jenny saw me looking at the clothes, and she really seemed to enjoy the fact that her mom wasn't letting me put anything on. And Jenny actually said, "Don't worry. Mom will let you get dressed once you're cleaned up."

Then I really started to panic, because looking at her looking at me was starting to make me hard. And I didn't have much to show down there yet, at age 11. I don't think there was any hair. If there was, it was minimal. And it was still very much just a little-boy penis. Maybe some growth, but not much. Still, I was getting erections at that age and I had started to masturbate, even if nothing was yet coming out. So just the fact that I was getting hard under my shorts was really embarrassing. I just hoped that Jenny wouldn't notice. And maybe it wouldn't get all the way hard anyway. But, of course, when I'd start to think about not getting hard, that would just make it worse. And with Jenny in there and looking at me—and with me looking at her face with that blonde hair and blue eyes, it wasn't making things any easier.

Then Jenny's mom told Jenny to go get a damp dish towel from the kitchen. I didn't know why. But Jenny merrily trotted through the door into the kitchen, still within view, and took a dish towel out. She asked her mom, "How wet do you want it?" Her mom was a little exasperated by this point, with this whole ordeal taking longer than she wanted it to. And her mom said, "He's got sauce all over his waist. I need to clean him up."

Jenny came running back, and eagerly handed the damp towel to her mom. They were both standing right in front of me at that point. And then, again with zero warning, Jenny's mom grabbed onto the waistband of my underwear and swiftly pulled them all the way to my ankles. Jenny audibly gasped as my hard little penis popped out and came into view, her eyes even wider than before, and the craziest smile on her face. I immediately covered with both hands. I was probably only exposed for a second or two. But again, it felt like a lifetime.

Jenny's mom had me step out of my underwear, and there it was. I was completely nude in front of Jenny. Just absolutely, completely nude, head to toe. You should have seen her face. I swear, I will never forget it. Her perfect blonde hair and those beautiful eyes, and that perfect face. Just all wide and looking at me. She and I made eye contact, and I could just see the thoughts running through her mind. She clearly thought it was the funniest thing in the world. I, on the other hand, was absolutely mortified.

Then Jenny's mom told me, "Turn around. I need to clean up the sauce." So I dutifully turned, knowing that Jenny was going to get a close-up view of my butt. It was almost more than I could take, but I was in it now. I couldn't talk back to Jenny's mom. So I turned around. I couldn't see Jenny's face at that point, but I could only imagine her exploring every inch of my butt with her eyes. I felt like I was on fire.

Then I felt Jenny's mom wiping the sauce off my waist as I stood there facing the other way. It didn't take long, but it was sure long enough.

Then Jenny's mom said, "Okay. Turn around. Let's get the front."

So I turned around. At least I was covering with my hands, so as embarrassing as it was, it could have been worse. A lot worse.

Jenny's mom wiped the sauce off my waist and belly.

And then she said, "Okay. Put your hands out so I can clean up your sides."

And holy crap. You can't imagine the thoughts running through my mind in that instant. I would have to completely expose myself to Jenny. She was standing right there! Granted, she saw it already when her mom pulled down my underwear. But that was just for like a fraction of a second until I covered with my hands. But now? Jenny's mom had explicitly told me to put my hands out at my sides so she could finish cleaning me up. And who knew how long that would take!!!

And in that instant, between Jenny's mom telling me to move my hands—but before I moved them, Jenny and I locked eyes. I can't imagine the look of embarrassment on my face. And Jenny looked back at me with this smirk, basically saying, Okay. Let's see what you've got. Again, an instant that lasted a lifetime.

So what choice did I have? I moved my hands out to my side. And as little and hairless as it was, it sure was hard and pointing straight out. I think Jenny didn't have time previously to notice I was hard, because I had covered up so fast. But this time, it was just out there. She audibly gasped again and there was a muffled laugh as she just stared right at it. I couldn't believe she was staring so hard. She kind of took a little step backwards and to the side so her mom wouldn't see her staring. Not that her mom would have noticed anyway. She was too busy cleaning the sauce off my sides and hips.

As her mom was cleaning me off, Jenny looked right at me and mouthed something like, "I see you!" And she pointed right at my penis, and then she took her forefinger and stuck it straight out and up, calling my attention to the fact that she saw I was hard. And she gave me like this teasing head tilt, basically saying "Sucks to be you right now!"

Finally, having gotten me all clean, Jenny's mom told her to grab some paper towels and bring them back. She brought them in, and Jenny's mom told me to take the towels and dry myself off. And she told Jenny to run up to Nate's room to get me a pair of underwear. Jenny took off like lightning, wanting to get back without missing a minute.

Jenny's mom stood up to leave the laundry room. I felt really bad for having made a mess and for taking her time. I apologized for the mess and the aggrivation, and she said don't worry about it. And she left me there, naked.

I immediatly grabbed the t-shirt and put it on, pulling it down in the front as far as it would go so I could cover myself.

Jenny came back in, and saw it was just me, and that her mom had left.

She said to me, "Wow, that was something. Didn't think that was going to happen when I woke up today!"

I didn't even know what to say.

Then she said, "You looked pretty funny, standing there naked. Can you believe? I saw you naked—from the back—and from the front! Isn't that wild?"

I still couldn't say anything.

But she kept going. "You should have seen your face when my mom pulled your underwear down. Not that I was looking at your face. I mean, you know. I was looking..." And she pointed in the direction of my penis. "But seriously. Your face was wild. Were you embarrassed?"

Was I embarrassed??? Was she kidding???

"Nah. I wasn't embarrassed," I lied.

She smirked at me again and said, "I call bullshit."

She handed me the underwear and watched intently as I took them. Because in order to put them on, I'd have to let go of my shirt and it would ride up above my penis, giving her one more look. But again, not having any other option, I let go of my t-shirt. And she immediatily said, "Nate's is bigger. I see him coming out of the shower sometimes. His is bigger. But you're younger, so it's okay." She was half teasing, but it was also like she was trying to make me feel better. It didn't, of course. But I appreciated the thought.

I got my underwear back on and was starting to reach for the shirt and shorts.

Then she said, "So it was hard, huh?"

Oh my god. "Um, yeah. I guess so."

She had a million questions about it. Like why does it get hard, how often, when, how long does it stay hard. All kinds of things. They were super embarrassing questions. But she kept asking. I did my best to answer. What else could I do?

Anyway, I finished getting dressed, and we both stood there, looking at each other. I don't think either of us had any idea what to say or do next. I mean, what do you say or do after something like that?

Then she looked at me with a teasing smile and said, "So... you know, you're welcome to come over for Spaghettios anytime."

I'm sure I turned bright red again.
Last edited by EverythingOff on Sun Nov 09, 2025 10:09 pm, edited 3 times in total.
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Re: Naked in Front of Jenny

Post by steam train »

Wonderful short story!
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Re: Naked in Front of Jenny

Post by EverythingOff »

steam train wrote: Mon Nov 03, 2025 4:23 am Wonderful short story!
Thanks! Glad you liked it.
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Re: Naked in Front of Jenny

Post by TeenFan »

How come they never put in scenes like this (mainly shooting the scenes without editing out the bare skin) in Hollywood movies?
I can see this being filmed in Japan or India...but not the good Ol' USA.
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Re: Naked in Front of Jenny

Post by EverythingOff »

TeenFan wrote: Tue Nov 04, 2025 2:55 am How come they never put in scenes like this (mainly shooting the scenes without editing out the bare skin) in Hollywood movies?
I can see this being filmed in Japan or India...but not the good Ol' USA.
Gee. I wonder why. :lol:
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Re: Naked in Front of Jenny

Post by NudeBaG »

LOVED this!
Deserves a follow up😉
Maybe a bit of show and tell is in order?
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Re: Naked in Front of Jenny

Post by EverythingOff »

NudeBaG wrote: Sat Nov 08, 2025 6:52 pm LOVED this!
Deserves a follow up😉
Maybe a bit of show and tell is in order?
Thanks!

Show and tell??? :oops: I don't know if he could take it!
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Naked in Front of Jenny - Part 2

Post by EverythingOff »

Naked in Front of Jenny - Part 2

After the whole incident, we went up to her room just to hang out. I was sitting on the rug on her floor in front of her bed.

She closed the door and looked at me. She didn't know what to say. Neither did I.

Then she blurted out, "You looked funny naked!"

"Jenny!"

I got so embarrassed all over again.

"Well, what! You did! You looked funny. With your little penis sticking up like that!"

"It's not little."

"I disagree. It's little. I'm not making fun. Whatever. You haven't started puberty yet. That's fine. You know. Boys are later than girls."

I looked at her and raised an eyebrow. "Oh, like you're all grown up. You don't even have any boobs yet."

"I do too!"

"Do not. Look at you. Totally flat. I mean, again, I'm not criticizing. But so what. You don't have boobs yet. You'll have them some day."

"Right. And you'll have a big penis some day."

"Right."

"Right."

We just sat there in silence for a minute.

Then she said, "Show me again."

"NO!"

"Why not? I already saw it. What's the difference?"

"It's not fair. You saw me naked, but I haven't seen you. Tell you what. You show me, and then I'll show you again."

She thought.

"Well, I'll make you a deal. I'll show you up here," she said, gesturing to her chest, "but I can't show you down there. It wouldn't be ladylike."

"You're no lady. You're just a girl."

"Fine. But that's my deal. Because I'm going to make you show me yours again either way. So we can do it the easy way and I'll show you my chest first, or we can do it the hard way, and you get nothing. Your choice."

She was right. She'd already seen me naked. So what was there to lose. And it was true that she didn't have much of a chest, but there were little bumps. At least, that's what it seemed like.

"Okay, Jenny. Fine. You win. Take off your shirt for one minute and let me look. And then I'll show you again."

"30 seconds."

"That's fine. You show me for 30 seconds, I'll show you for 30 seconds."

She thought for a while. Then she said, "Okay. Fine. One minute."

"Deal." We shook on it.

Well, she was a girl of her word, I'll give her that. Just sitting there on the floor right in front of me, she just lifted up her t-shirt and pulled it over her head, and held it in her lap. Wow. My eyes fell out of my head. Okay, so it was true. Not much there. But just the idea that she was letting me see her without a shirt. It was incredible. I just looked and looked. I wanted to touch so bad, but I didn't. I got kind of shy about it. They were starting to come in. You could tell. She was really pretty.

Then she put her shirt back on.

"Wait! No way that was a minute."

She looked at her phone. "Nope. It was. Serious. No cheating."

"Wow. That went by fast. Can I have another minute?"

"Maybe. After you show me yours again. One minute."

I got nervous. I asked, "Okay. How do you want me to do it."

And she said, "Stand up and pull your pants and underwear all the way down. And then just stand there. One minute."

It's crazy, but I was even more nervous this time. More nervous than I was when we were downstairs and her mom was cleaning me off. Maybe because this time she was telling me what to do instead of just watching it happen. I thought that was pretty cool, that she wanted to see it so bad that she was basically ordering me around. It made me nervous and excited, but it was fun. I liked that look in her eyes and her tone of voice when she said, "Stand up and pull your pants and underwear all the way down. And then just stand there. One minute." She was nice about it, but she was very direct. Like she knew what she wanted. I was no exhibitionist, but if Jenny wanted to see me naked again, I didn't really mind, I guess. It was still embarrassing, but it was fun. And plus, she had taken off her shirt for me. So it seemed okay.

"Okay, Jenny," I said as I stood up. When I stood up, I realized that her face would be like two feet away, right in front of my penis. There'd be no hiding anything. But that's what I had to do.

"You ready?" I asked.

"Ready," she said with a big smile.

I hesitated just a second, but I did it. Just in one movement, down they came. My shorts and my underwear, just all the way down to my ankles. And I stood there. I had the timer going on my phone. One minute.

Then I looked at her looking at it, and I got really excited. You know what I mean. And it got that way FAST.

Jenny was really interested. Honestly, I was hoping she'd ask to touch it. But she didn't. Then I was thinking I could ask her if she wanted to touch it. But I didn't.

I saw her looking at it. She was moving her head all around to see it from different angles.

Then she said, "It is small. Again, not that I care. It'll get bigger someday. But it's pretty small."

I didn't really like her calling it small. But I guess I didn't care all that much. Either way, she seemed interested in it... and in me. And that was fine with me.

"Minute's up," I said, looking at my phone and reaching down to pull up.

But she said, "How about a little longer?"

"But you just showed me for a minute. That was the deal."

"I know. But yours is a lot more interesting than mine. I just have little bumps. You have a whole penis and balls. It's a lot to digest. I need more time."

"Um, okay, I guess."

It was embarrassing, but, again, I was enjoying the attention.

Looking right at it, maybe from just five or six inches away, she said, "Boys are lucky."

"Why do you say that?"

"I don't know. I just feel like boys are luckier than girls."

I didn't know what she was talking about, but I didn't ask.

"Step out of your underwear and shorts. I think you should stay naked."

"What???"

"Yeah. Step out. I'm not done looking yet, and I don't want to have to worry about the timer anymore. So just step out, and you'll stay naked until dinner."

I didn't know what to say, but she just took charge. She reached out and lifted my foot... and then the other foot... and she took my shorts and underwear and put them on a shelf.

"Now your shirt," she said.

"What??? I'll be totally naked!"

"Whatever. I've already seen you totally naked. Remember? Downstairs??? Now come on. Take off your shirt."

She was pretty demanding, and I couldn't figure out a way to say no. So I did. I pulled off the t-shirt and she took it from me.

Then she stepped back and looked at me. I was completely naked.

She smiled.

"I like it. Yes, we'll keep you this way until dinner. Are you staying for dinner?"

"Sure, I guess so. That's fine."

"Perfect. You're naked until dinner."

"Um, okay. But what are we going to do until then? That's like three hours away."

"Oh, don't worry. We'll come up with something."
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Re: Naked in Front of Jenny (New 11/9)

Post by Freesub »

I like the premise of him staying naked, though it would feel about more natural if he negotiated her staying topless as a part of it
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Re: Naked in Front of Jenny (New 11/9)

Post by EverythingOff »

Freesub wrote: Mon Nov 10, 2025 2:01 am I like the premise of him staying naked, though it would feel about more natural if he negotiated her staying topless as a part of it
Good idea. He may get some topless moments out of her. He seems relatively confident in front of her. Maybe even enjoying it a bit. But I think she has some plans that might surprise him a bit. :oops:
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