Tickling and Stripping Chrissie's Little Brother

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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TheBlushingPrincess
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Tickling and Stripping Chrissie's Little Brother

Post by TheBlushingPrincess »

Here's a single-parter. I hope you like it.

Tickling and Stripping Chrissie's Little Brother

I'm not sure the best way to tell this, so I'll just tell it.

When my friend Chrissie and I were 16, we were hanging out at her house. Her brother was just a year younger than us. Maybe 18 months, but just a year behind us in school. He was cute, but kind of annoying sometimes. As younger brothers are. He was kind of late to develop. Still very young looking. I'm not even sure if he was shaving yet, and if I had to put money on it, I'd say he hadn't matured much yet down below. Not that I was interested in the least. I mean, he was a nice enough guy, but I wasn't going to go out with my best friend's little brother.

So he comes into Chrissie's room asking for this or that. She's annoyed with him and tells him to get out, but he keeps staying. Okay, it's been clear for some time that he's got a kind of a thing for me. I get it. Older, pretty, blonde. Okay, I mean, sure. I'd make out with him if he made a move, but he's not going to, and really. That's just fine.

Okay. But to the good part of why I'm sharing any of this.

Chrissie says, "James, get out. Or I'm telling Lindsey what you said."

Then he gets all flustered and I start smiling and teasing.

"Oh? What did you say, James???"

He's not leaving but he's not talking.

"You're not going to tell me?" I ask, slyly.

"Chrissie! Come on!"

And then, well, I just couldn't resist it.

I say, "Okay, James. Come here." He walks over. And I say, "If you won't tell me, we're going to tickle it out of you!"

He gets all indignant and says, "Whatever. I'm not even ticklish."

And I'm like, "Bullshit. You've got 'ticklish' written all over you."

"Nope. Sorry to disappoint."

So I say, "Tell you what. We'll tie you to the bed. If you can make it five minutes without begging us to stop, you win. If not, you tell me what you said."

I shoot Chrissie a smile. And James is like, "You're kidding."

"No, I'm not." I get up and walk over to him. "You lay down on the bed, we tie your hands above your head, and we tickle you for five minutes. You make it the whole time without begging to stop, and you win."

I really am hoping he'll agree. I've never tied anyone up before. This would really be fun!

And Chrissie prods him, "Okay, tough guy. You say you're not ticklish. So prove it!"

"Fine!" he shouts. So we bring him to the bed and we grab a couple of scarves from Chrissie's dresser.

"Hands over your head, James," I say, sweetly. He does look cute. So he puts his hands over his head and we tie his wrists to the headboard, both wrists tied together in the center of the headboard, all stretched out."

"Aw, James. Look at you! Ready for your tickling?"

"You'll see," he says, squirming already. "I won't even laugh. Not once."

Chrissie and I hop up on the bed, kneeling on either side of him.

"Okay, James," I say. "Let the tickling begin!"

And we just pounce on his belly, through his shirt. Four hands digging and twisting. And yeah. He was totally lying because he starts screaming and laughing right away. And of course, the laughter is totally contagious, and we start laughing too."

We keep working our fingers, and I say, "Isn't this great, James? Two is soooo much better than one, isn't it?"

Chrissie says, "Double the pleasure!"

And I add, as I dig in even harder, "Double the bitchiness!!!" Ha!

And Chrissie says, "Listen to him scream, Lindsey. Do you think he wants us to stop?" She kind of works her fingers over to his side, still through his shirt.

"Stop?" I answer. "Why, this is WAY too much fun. I don't think I'd EVER stop!"

The screaming is wild, and Chrissie and I are just laughing quietly watching him squirm.

And I remind James, "Now remember, you can just tell me what you said and we'll stop!"

"No! No! I won't tell!!! Chrissie, you bitch!"

We both smile at that. And Chrissie says, jokingly, "Well, you know, calling me a bitch didn't really help your cause!" And she moves up to his armpits, still through his shirt. That makes him go wild, so I go up to his other armpit on the other side. He's really laughing and moving now.

Then I tease him, "Unfortunately for you, James, I forgot to look at my phone before we started, so I have no idea how long we've been going. But whatever. This is so much fun!"

And he shouts back through his laughter, "THIS... IS... NOT... FUN!!!"

But Chrissie says, "I don't know what you're talking about, James. I'm having the BEST time!"

Then I say, "Let's explore a little bit. Let's see about those feet!"

So Chrissie and I bounce down to the foot of the bed and pull his socks off.

"What are you doing???" he yells.

And I'm like, "Hey, we need to explore a bit. You don't want us getting bored do you? Now hold still!"

And Chrissie and I both grab an ankle, hold him still, and start working the soles of his feet. And wow. He just goes nuts.

"WHAT DID I DO TO DESERVE THIS???"

Chrissie stops and thinks, looking at me. "Hm. What DID he do to deserve this?"

And I just say, "He didn't do anything. We just wanted to have some fun. It's just what we do!"

So Chrissie goes back to his feet, and she says, "Now hold still. We need to count your cute little toes. One little piggie... two little piggies..." And he's thrashing like wild.

But then I got an idea. I mean, you know how I get. And I stop tickling him for a minute. Chrissie is still teasing his foot with her fingernail, but it's light and he's kind of calmed down for a minute, catching his breath.

And I say, "You know, we really can't get to most of your skin because you're wearing all those clothes."

And I just watch his face as he realizes what I'm saying. He starts to shake and pull at the scarves, but he's not going anywhere.

"Lindsey! What are you talking about?"

And I just very matter-of-factly state the obvious. "Well, if we really want to tickle you all over, we'd have to take off your clothes. Because right now, we can really only get to your feet and your belly. But if I want to tickle your legs, I'd have to go through your jeans, and that wouldn't be very good. I mean, I need access to skin, right? Right, Chrissie?"

She's really having a good time watching her brother squirm like this.

James is kind of panicking, and pleads, "Chrissie!"

But I just keep talking. "See, the thing is, James, with you all tied up like that, I could pull your shirt over your head and you couldn't do a thing about it. Like this, see?" And I grab his shirt and slowly pull it over his belly and hairless chest. "Aw. Look at those cute little nipples! Hewwo! Hewwo!" I say, in kind of a baby voice, waving at his little nipples.

"Lindsey! Come on!"

He's twisting his neck and head to keep me from pulling his shirt up, but really, it's not an issue.

"There! See? Now I have access to so much more skin to tickle!" I dig my fingers into his ribs a little and he jumps and screams."

"Wow, James. Even I didn't know you were this ticklish!" Chrissie says through a grin.

"Okay, Lindsey. Okay. You win! Okay? You win!"

"So you're going to tell me what you said?"

"CHRISSIE! MAKE HER STOP!"

But Chrissie just smiles. "You got yourself into this mess, James. You can get out of it."

He pulls at the scarves and says, "No! I CAN'T get out of it!"

"Well," she tells him, "you'll have to suffer the consequences of your decisions, then."

So now I'm thinking, do I really want to take this further. But I don't have to think about it long.

"See, James. That was easy. I just pulled your shirt up and there was nothing you could do to stop me."

"LINDSEY! COME ON!"

"But as much as I want to tickle your chest, I think I want to tickle your legs even more. But I can't do it through these jeans."

And without saying a word, I start to unbutton his fly. He's really struggling now. For good measure, Chrissie moves to the head of the bed and holds his hands still so he really can't break out.

"There, James. See! This will be so much better." And I start to pull his jeans down. He's really begging and squirming, but this is way too much fun to stop now.

"See, James? Nothing you can do to stop me." I get his jeans down to his knees. "Aw. And tighty-whities! So adorable! Love it!" And I maneuver his jeans all the way off. I hold them up in my hands like a trophy and taunt him with them. There, James, see? Nothing to it! You're making this so easy!" And I carelessly toss them across the room.

"Now, back to the tickling..." And I kneel back on the bed next to his legs.

"Lindsey! Please! I'm warning you!!!"

"Warning me how, exactly, James? How are you warning me? What are you going to do? You're practically naked and I'm about to tickle the shit out of you. So how is it that you're warning me?"

And without waiting for a response, I bring my hands to his thighs and start tickling him. He thrashes like crazy.

"Oh, wow! There's the spot!" I dig in more. "James, your legs are so smooth and soft! Really! I could do this FOREVER!"

But then I look. And I notice. I see it. Oh, shit. This is too funny.

"Um, James?" I stop the tickling.

"WHAT???"

"Um, it seems that your, um, thing is, um, a little, um, excited."

He turns bright red and Chrissie starts laughing.

"LINDSEY! COME ON!!!"

"You know, James, it occurs to me that just like you couldn't stop me from pulling your shirt over your head, and just like you couldn't stop me from taking off your jeans, I don't think you'd be able to stop me if I wanted to pull down your little tighty-whities. Could you? Do you think you could stop me?"

"LINDSEY! CHRISSIE! DON'T LET HER!"

"Hey, I'm not saying I'm going to. I just want to know if you think you could stop me. Do you think you could stop me?"

Chrissie is just dying laughing. Not that she has any interest in seeing James naked, but I think she's enjoying his humiliation. At least, she's not stopping me from teasing him.

"So what do you think, James. If I wanted to take your tighty-whities off, do you think you could stop me? It's really just a yes or no question."

Finally he yells, "No! Okay! I couldn't stop you! Now let me go!"

"Yeah. I didn't think you'd be able to stop me. But just to be sure, let's find out."

"WHAT????"

"Yeah. Let's just take them off."

"NOOOOO!!!! LINDSEY! CHRISSIE!"

But I'm done fooling around. I grab onto those shorts and very slowly, I start pulling them down.

"So let's see what James has got down there! Oh, wow! Look at that! So hard! James! You must really be enjoying the tickling!"

Chrissie isn't looking at it. I don't think she wants to see it. She's kind of looking away, but she's dying laughing and holding onto his hands and arms for dear life. This is WAY too good.

"Okay, James. Please stop kicking for a minute. I don't want to get hurt while I slide these off your legs." His thrashing is insane.

Then, with his shorts down and off, I stand next to him, dangling them from my finger. "And there you are James. See? I did it! I took off your shorts without you being able to stop me. And now I'm just holding them in my hand. What about that! I pulled up your shirt, took off your jeans, and now I've got your shorts. And there you are. All naked, tied up, and I could just do whatever I want. I could tickle you some more, I could just sit and look at you. Oh, I mean, I could get some ice and torture you. Really, the possibilities are endless. Or... you could tell me what you said before."

"FINE! FINE! YOU WIN! I'LL TELL YOU!"

"Oh, good!"

"But not out loud. Come here. I'll whisper it to you."

So I leaned in. He whispered it in my ear.

It was actually very sweet.

So I whispered something back in his ear.

We looked at each other a minute.

And then I said, "Okay, James. You can go now." And I untied his hands. And this was really cute and funny. He gets up, all naked (I couldn't help from saying "Cute butt!") and he came over to me to collect his clothes. But I pulled them away. "Nope. I want to see you streak down the hall back to your room."

Well, he wasn't waiting around to argue with me. Off he ran, his dick and balls bouncing every step, out of Chrissie's room.

Wow. I'll tell you. It was really about the funniest thing I had ever seen.

I teased him pretty hard about it next day. You know, with the tickling and the naked and the boner. Sorry I didn't take any pictures. Oh, well. Next time, right?
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Re: Tickling and Stripping Chrissie's Little Brother

Post by Darky »

I’m normally not into ENM but this one was hot!
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Re: Tickling and Stripping Chrissie's Little Brother

Post by TheBlushingPrincess »

Darky wrote: Fri May 03, 2024 5:01 pm I’m normally not into ENM but this one was hot!
Always happy to find another convert. As for me, I go both ways, but I think we all knew that. :lol:
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Re: Tickling and Stripping Chrissie's Little Brother

Post by chwipiwr »

So now she knows about James’s crush and ticklishness will she be back for more? And will she give him a chance to get his own back?
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Re: Tickling and Stripping Chrissie's Little Brother

Post by Britguy »

Fun story. Thanks.
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Re: Tickling and Stripping Chrissie's Little Brother

Post by Trundle »

Great to have you back and a really well written fun story as always !

Will there be a way for us to read any of your old stories again?
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Re: Tickling and Stripping Chrissie's Little Brother

Post by TheBlushingPrincess »

Trundle wrote: Fri May 03, 2024 8:25 pm Great to have you back and a really well written fun story as always !
Thank you. It was a fun piece to write. Something I've had in my mind for a long time, but I always make it too complicated and give up. So I just kept it short, sweet, and simple!
Trundle wrote: Fri May 03, 2024 8:25 pm Will there be a way for us to read any of your old stories again?
https://www.deviantart.com/theblushingp ... -988496606

Not everything is there, but most of it is. I was also thinking of doing some gender-swaps with a couple of old stories. I was thinking of retelling "Kelly's Hazing" with a male victim. So we'll see.
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Re: Tickling and Stripping Chrissie's Little Brother

Post by TheBlushingPrincess »

chwipiwr wrote: Fri May 03, 2024 6:17 pm So now she knows about James’s crush and ticklishness will she be back for more? And will she give him a chance to get his own back?
Well, this was a one-parter. (It always feels good to actually end a story with the words "The end.") So if there are future episodes between James and Lindsey, they will likely be in our collective imaginations. :lol:
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Re: Tickling and Stripping Chrissie's Little Brother

Post by Lefanto »

As always, a pleasure! :)
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