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Her Sister's Babysitter - The girl Liam is babysitting has some plans for her older sister.

Part 1: Her Sister's Capture - The girl Liam is babysitting presents him with a unique opportunity.
Part 2: Her Sister's Pussy - The girl Liam is babysitting starts exploring her sister's pussy.

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*Bit of a twist on a classic. Hope you enjoy.*

“Thank you again so much for doing this, Liam,” Mrs. Kyson said.

“Yeah, no problem,” I said.

“Are you sure you’re okay to take care of her for two days?”

“Don’t worry about it,”

She nodded, smiling again and gathering up her things. “Haven will be in and out of the house, so she can help with any questions that you might have, and she’ll be here for the night so you don’t need to stay over. I’ve put money on the counter for the two of you to get pizza. Otherwise...” She turned to her 8-year-old daughter. “You be good, Sophia. Don’t give Liam here any trouble, okay?”

Sophia grinned, dimples in her face. “Mama, I’m an angel!” She giggled, and the sound made me chuckle.

“You best get out, Mrs. Kyson, or you’ll be late.”

She nodded, checking her watch and then scrambling out the door.

I turned to Haven who stood at the other end of the hall. “So...”

She rolled her eyes. “Just leave me alone. I’m going to a party, don’t know when I’ll be back.”

I blushed. She was nearly three years older than me, but that didn’t stop me from having a huge teenage and hormonal-driven crush on her all throughout high school until she graduated. I was 14 or 15 and she was 18. Now that we were both home from college for the summer, and I was 19 and she was 22, it took everything I had not to fawn all over her.

I raised my hands, as if in defeat. “Alright, you do you. I’ll stay here and take care of Sophia. Your mom just said to check in on Sophia around 6:00, okay?”

She groaned. “You’re not my babysitter. You can’t tell me what to do.”

I shrugged. “I don’t care what you do, I’m just telling you what Mrs. Kyson told me.”

“Fine. But I’m heading out right now.” She pushed past me.

From what I knew, Haven had always been a bit of a firecracker, and was one of the reasons why Mrs. Kyson wanted a second babysitter even though Haven was old enough to do so. And for some reason, Sophia liked me, so it worked out well for me to make a little extra cash.

As the door closed behind Haven, I turned to Sophia and grinned. “Want to watch a show?”

She clapped, jumping up and down. “Yay!”

I turned on the TV and pulled out some homework while Sophia watched. It was a silly little show, like Bugs Bunny or something. There was a bit where the main character, an animal, got tied up to some dynamite, only for the hero to escape and trick the villain, another animal into taking his place. Sophia cackled as the bad guy blew up in a puff of smoke, leaving him in only his “underwear” of fur.

“I’m hungry!” Sophia said.

I glanced down at my watch: 6:20. Haven was late.

Where are you? I texted Haven.

I’m on my way. Just chill, okay?

I’m going to get pizza. I messaged. I need you to stay with Sophia until I get back.

No way! I’m going right back to my party after your dumb check-in.

Please? It’ll only be a few minutes while I pick up the pizza.

Fine.

Eventually, her car pulled up and she came through the front door.

She rolled her eyes at me again. “You happy?”

“Great. I’ll just be a minute. Just hold tight, Sophia.” I glanced at Haven. “Make sure she doesn’t go anywhere.” I wasn’t sure if I was talking to Haven or Sophia

I zoomed to the store, but it felt like it was taking forever for them to pull the pizza out. Something about a broken oven.

What’s taking so long??? Haven texted me.

Pizza was delayed. Almost there. I was worried that Haven was going to leave Sophia alone. I hurried to my car and booked it back to the house.

When I opened the door to the front of the house, something felt off. There was rubbish all over the floor, like two animals had been fighting. “Sophia?” I panicked. Had something happened?

“Liam? Come in here!” Sophia shouted from the kitchen.

I ran in, relieved at the sight of Sophia unharmed.

What I didn’t expect, however, was the sight of Haven tied to a chair and gagged. Her eyes bulged at the sight of me, and she screamed into her gag. Her legs were bound to the legs of the chair, spreading her mini-skirt so I could see the slightest bit of her pink panties.

“She tried to leave, but I didn’t let her,” Sophia said, putting her hands on her hips. She seemed rather proud of herself.

“Umm...good job, Sophia.” Holy crap, what was I supposed to do? I couldn’t help but stare at Haven’s perfectly toned body, with her long, shaven legs and flat stomach.

“She’s been naughty,” Sophia said. “I think she should lose her clothes like the bad guy.”

“Wait--”

Before I could say anything, Sophia grabbed the hem of Haven’s skirt and pulled it down. Haven squirmed and bucked against her bonds, but it did nothing.

Sophia giggled as she reached over to unbutton the top two buttons of Haven’s blouse with her small hands, fumbling with them. She pulled them open a little too harshly, and the third button *popped* and flew out onto the floor. Haven groaned, knowing her pink opaque bra was now in full view.

She looked at me, her eyes wide and terrified. Sophia was on a warpath. Haven knew that I alone had the power to stop her sister. And that power was intoxicating.

Okay, maybe this was going a little too far, I decided. As I opened my mouth to tell Sophia to stop. However, I hesitated. As I looked over my childhood crush, her pink underwear completely in view and completely vulnerable, I felt something stir in my crotch. I would never do anything, but I was suddenly finding it difficult to find the words to tell Sophia to stop.

“Liam, don’t you want to help?” Sophia asked as she tore off the rest of Haven's blouse.

“What? Oh, yeah, sure.” I reached over and grabbed Haven’s bra. She screamed and recoiled from my touch, but she couldn’t go far. Her sudden movement put strain on her bra, and I heard a *pop* as the clip behind her back snapped, and her bra came apart in my fingers. Her squealing picked up a notch as her perfectly round and perky breasts came into view.

Sophia giggled at her sister’s predicament. “They’re so big.” She reached over and grabbed one of Haven’s breasts. “C’mere, Liam. Feel them.” She grabbed my hand and guided me to Haven’s other breasts. Haven’s screams turned into a purr as I stroked her breast, rolling her nipple with my finger.

“Uh-oh!” Sophia said. “Looks like she peed herself.”

I glanced down at Haven’s panties. They were definitely wet, but I didn’t tell Fiona that it wasn’t pee, instead content to watch as she grabbed the panties and tore them off, completing her sister’s stripping. Haven’s pussy was indeed very wet, and I found myself admiring her perfectly shaved slit, her lips just slightly protruding from her pussy.

Looking at my crush’s naked body was sending my own into overdrive. It took everything I had not to jerk off in front of the two girls, so instead I shoved my hands into my pockets.

“What should we do now?” Sophia asked. “I think we should punish her.”

I gawked at the little girl. What was she, some kind of sociopath? Punish her?

Unable to do much else, Haven was reduced to glaring at us, but to me it only served her highlight her vulnerability.

I shrugged, deciding to go all in. “Well, Haven, you did miss your check-in time. And I think you’re enjoying this a little too much. I think we should spank her.”

Haven moaned as she realized that she was getting no help from me.

“Yay!”

I untied Haven, making sure that I had a firm grip on the rope that bound her. I picked her up and repositioned her over the chair, so her stomach lay on the surface and her butt hung off the side. I spread her legs wide and tied them to the chair, so everything was in view from her pussy to her perfectly round and flawless butt.

Sophia went to town on her sister’s butt, giving her sister several loud and painful slaps. Haven moaned and sniffled as tears ran down her face. I admired the red splotches that emerged for a moment, taking a second to appreciate Haven’s vulnerability again before proceeding with my own spankings. With each strike, Haven squealed, a sound that I savored. As I proceeded, her squeals became softer and softer until she eventually became silent, completely submissive to her tormentors.

I stopped, admiring her very red butt and prone position. We took a break, eating our pizza and laughing about funny things in kids’ shows, all with our trophy lying on the chair in front of us.

Sophia wiped her mouth of pizza grease. “I have another idea for her punishment.”

“Yeah?”

“Did you know that my sister is ticklish?”

This started a whole new slew of protests as Haven begged through her gag. Sophia stooped down and started to tickle her legs and feet while I reached over and ran my fingers up and down her stomach, my hands wandering near her breasts and flicking her stiff nipples, eliciting a moan each time. With each run of my fingers, she screamed and thrashed, powerless to stop either of us.

I glanced at Sophia, who was having the time of her life attacking Haven’s feet. I reached down and pinched Haven’s clit and stuck my finger in deeply. Haven let out a long, drawn-out moan as her body shuddered. I pulled out just as globs of cum squirted out of her, splashing on the wood of the chair and soaking the carpet.

“Ewww...” Sophia said. “She peed a second time.”

Again, I didn’t correct her.

Haven slumped over, out of breath, out of energy, and completely defeated. She was too cute, I thought. There was no way I could let this end.

“Well, Sophia, I think it’s time we get you to bed,” I said.

“Awww...I want to play with Haven more!”

“I know,” I said. “We’ll play with her some more tomorrow, okay?” Haven peaked up at this, mumbling a soft complaint into her gag.

“You promise?”

“I promise.”

“What if she gets out at night?”

I looked at Sophia, and then at Haven, and grinned. “Don’t worry. I’ll make sure she doesn’t go anywhere.”

Enjoy the story? Got an idea for a Part 2? Let me know!*

I really enjoyed your refreshing twist on a classic trope! It touched on all the bases: stripping, spanking, and forced squirting. The fact that Haven was Liam’s older childhood crush made everything so much better. I am always partial to stories that feature an older, college girl humiliated in front of younger boys she thinks she’s superior to.

A couple ideas for part 2:
1. Since Sophia noticed that Haven “peed” herself, maybe she insists that her older sister wear diapers— just like her mom makes her wear when she has an accident. It’s only fair.
2. Since Haven was so insistent on going to the party, perhaps Liam and Sophia can host a party for Haven! They can invite all of Haven and Liam’s college friends! And I’m sure Haven would love to see some of her old high school friends!

You could also take it in a completely different direction and have Haven realize just how much she enjoys Liam’s touch. Maybe the supercilious Haven will realize that Liam is the right guy for her after-all.

mastergepetto wrote: Wed Jul 06, 2022 4:49 pm I really enjoyed your refreshing twist on a classic trope! It touched on all the bases: stripping, spanking, and forced squirting. The fact that Haven was Liam’s older childhood crush made everything so much better. I am always partial to stories that feature an older, college girl humiliated in front of younger boys she thinks she’s superior to.

A couple ideas for part 2:
1. Since Sophia noticed that Haven “peed” herself, maybe she insists that her older sister wear diapers— just like her mom makes her wear when she has an accident. It’s only fair.
2. Since Haven was so insistent on going to the party, perhaps Liam and Sophia can host a party for Haven! They can invite all of Haven and Liam’s college friends! And I’m sure Haven would love to see some of her old high school friends!

You could also take it in a completely different direction and have Haven realize just how much she enjoys Liam’s touch. Maybe the supercilious Haven will realize that Liam is the right guy for her after-all.

Thanks! I like how it similar but circumvents that "cliche" story for enf. That's also an interesting idea with the diaper, I might see what I can do with that.

Her Sister's Babysitter - The girl Liam is babysitting has some plans for her older sister.

Part 1: Her Sister's Capture - The girl Liam is babysitting presents him with a unique opportunity.
Part 2: Her Sister's Pussy - The girl Liam is babysitting starts exploring her sister's pussy.

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Sophia in bed, I grabbed a small pillowcase and slunked my way back down to the kitchen. My breath caught as I saw in the dark kitchen the silhouette of her perfectly round and soft butt, completely displayed in front of me. It was still surreal, seeing my crush completely naked, vulnerable, right here in front of me.

I stepped up to her quietly. She hung there, quietly, with her eyes closed. I had wondered if she would try to escape as I put Sophia to bed, but apparently, she was too defeated to try. Her hair was a mess, and her body was contorted from her efforts to escape her bonds during our tickling.

I reached down and started to untie her.

Her green eyes opened, a moment of panic, replaced with relief. “Mmmff...”

I realized that she thought I was freeing her. “Sorry, Haven,” I said. “Not yet. I made a promise to Sophia, so I can’t let you go.”

“Mmff!”

I pulled per onto the table and stretched her limbs to each corner, tying them to the table leg underneath until her body was bound in a spread-eagle position.

I took a moment to admire her very vulnerable and exposed position, with everything on display. I reached over and pinched her nipple, eliciting a squeal. I was mesmerized by her tits, how perfect they were. Smooth, pink flesh, not too big or too small, with large, distinct areolas with her pink nipples perfectly centered.

“Time for a little revenge for all those years you were mean to me,” I said. With Sophia in bed, I could be much rougher. I straddled Haven on the table, and bit down hard on one nipple with the edge of my teeth. One of my hands wandered from my chest, inserting itself into her pussy. She moaned, unable to do anything to stop me or even having a chance of relieving herself, given that she was dry from just orgasming.

I pulled myself off, looking Haven up and down. My crotch was throbbing. Her gorgeous green eyes were wide, looking at me with such vulnerability and terror. I reached over and pulled her hair back from her face. She moaned as my thumb stroked her cheek, and I felt a slight shudder of pleasure run from her body to my finger.

I grinned. “You’re enjoying this, aren’t you?”

She shook her head furiously, unable to use her words to defend herself.

I shrugged, rubbing her side boob with my fingers for a moment. I leaned down to kiss her on the cheek. She shuddered again at the feeling of my mouth on her skin. “It’s okay,” I whispered. “Sophia and I will get the truth out of you tomorrow. Sweet dreams.” I placed the pillowcase over her head and tied it lightly with some string.

I found my way to the guest room, not wanting to waste time driving the next morning. Despite my excitement of what was to come, I slept rather well that night.

“Liam! Liam!” Sophia was practically jumping on me as she woke me up. “Time to play!”

I pulled myself off the bed, letting Sophia guide me downstairs. Haven, her face still covered by the pillowcase, turned her head in our general direction. Sophia came up and pulled off the pillowcase. Her hair had come unraveled again in the night, and Sophia started to tidy her up. She was shaking furiously, her legs pulling against her very tight bonds. At first, I thought she was trying to make one last effort to escape, but then I realized that she was trying to stave off the feeling of needing to pee.

“Good morning, Haven,” I said with a grin.

She moaned against her gag. She knew that I knew that she needed to use the bathroom. She also knew that I wasn’t going to let her.

Sophia, unaware of what Haven needed, just giggled. “What is she doing?”

I shrugged. “I don’t know. Come on, let’s make breakfast.”

As Sophia and I stepped over to the fridge, Haven moaned and keeled over, nearly picking up the heavy chair she was bound to. She shuddered, and then the smell of urine filled the air. It dripped down Haven’s legs and deposited into a puddle at her crotch. She sniffled, her face completely red in humiliation.

“Ewwww!” Sophia said, plugging her nose with her fingers. “She peed again! That’s the third time!”

“Yeah, it is starting to be a problem,” I said. “Should we do something about it?”

“Mmf?”

Sophia scrunched up her face in deep thought. “Whenever I wet the bed when I was littler, Mom made me wear a diaper.” Her eyes lit up. “We have some diapers upstairs we never threw away!”

She ran up, and I stepped over to Haven, grabbing a tower to wipe up her piss. It hardly registered with me that her current state of undress wasn’t normal. It just felt right, like she was always meant to be naked and exposed.

Sophia returned with a box of unopened diapers. She helped me unfurl it and I wrapped it around Haven’s waist, letting my fingers drag across Haven’s pussy as I tucked it underneath her. She responded with her eyes nearly rolling into the back of her head in pleasure.

The diaper was very small and was very tight against her crotch, just barely wrapping around her pubic area but leaving her legs very exposed. I was disappointed that it covered her pussy now, but it served to highlight her bare chest. And it kept Sophia happy, which, to me, was key to keeping this whole experience from ending.

Up until this point, I was content to let Sophia lead in Haven’s humiliation, enjoying how easily Sophia inflicted embarrassment on her sister. But I wanted more.

“Sophia? I just got an idea of what we could do this morning,” I said.

“What is it?”

“How about we run some...experiments on your sister?”

Sophia clapped her hands. “I wanna see how wide her privates can go!”

I nodded. “Good idea. Grab a ruler and some pencils.”

Haven’s head fell back and she groaned as Sophia disappeared. Her eyes were closed shut, trying anything to block out the experience she was going through. I looked down at her. “I’m not going to let anything happen to you, Haven, but you are going to be subjected to whatever I want. Sophia may have been the one to tie you up, but you’re my prisoner now.”

I reached down and unraveled her diaper, exposing her pussy again, but I let the rest of the diaper just hang on her, cushioning her butt and wrapped around her hips. Already, her pussy was starting to glisten with wetness. She groaned, her eyes still closed.

Sophia returned with a couple of #2 pencils with unblemished erasers at the top, a plastic, 1-foot ruler, and some paper.

“You ready to measure?” I asked Sophia. She nodded and placed the ruler above Haven’s privates, who moaned at the sensation of the cold plastic on her skin.

I stuck both pencil, eraser-side up, into her pussy, and Haven screeched as I moved them apart, spreading her pussy as wide as possible. I held it there for a few seconds as Haven screamed gag-muffled obscenities.

“Got it!” Sophia yelled. I pulled out and looked at Sophia’s measurements. I whistled. “That’s quite a pussy you got there, Haven.”

“Your turn to do an experiment, Liam!” Sophia said.

“I think we should keep up with her pussy. Can you grab me a bag of ice, Sophie?”

Ice in hand, I stood over Haven. She looked at me, confusion and trepidation in her eyes. "We're going to see how long Haven can last with this on her privates. If she can last more than 2 minutes without moving, we’ll let her go.”

Sophia groaned. She didn’t like the idea of having to let Haven go. Haven herself looked at me, hope suddenly filling her eyes that I would release her.

I started the timer on my phone and pushed the bag of ice onto Haven’s privates. She moaned, unable to move her legs to protect herself or having any pubic hair to provide warmth.

30 seconds. I pressed down harder, my hands slick and cold from the melting ice. I could only imagine

45 seconds. Haven was shaking, twisting and pulling at her bonds any way she could,

A minute and 15. Haven’s eyes were glazed over, trying to retreat into herself.

A minute and 30. Something cracked. Haven’s shaking turned into panic. Her left hand broke free and her arm flew to her crotch, but she was unable to reach it. “Smf! Smf! Smfff!”

I kept the ice bag pushed up against her pussy “What was that?”

“Smfffff!”

“You want us to stop?”

“Ymf! Ymf!”

I pulled off the ice, and Haven collapsed, her stomach rising and falling as she struggled to breathe. Her face was streaked with tears, and her crotch, inner legs, and diaper were covered with cold water. The rest of her body was glistening with sweat. Her freed hand just hung there, not even trying to free herself.

I looked at the timer. “A minute 55, Haven. You just missed it. Guess we’ll have to do another experiment.” I pulled her arm tenderly behind her, retying her arm to the table leg. She groaned, realizing how close she was to ending her torment.

I turned to Sophia. “What’s next?”

*Got any ideas of what kind of "experiments" you want Sophia and Liam to perform on their poor test subject? Let me know!*