Babysitter Bondage Bet (f/m) Pt. I

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GameOverGuys
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Babysitter Bondage Bet (f/m) Pt. I

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"I'm warning you, no parties, and keep an eye on your sister. If she's too much for you to handle, just call Aunt Becca." Hurriedly gathering her bags for her weekend-long trip, my mom sternly wagged her finger at me while I pretended pay attention.

"I know, Mom. Stop worrying so much, this is the easiest job I'll ever have."

Unconvinced, she stared at me in silence for a few seconds before repeating, "If you need help, call-"

"-Aunt Becca, I know!"

All I could think about was having my girlfriend spend the night, and couldn't wait to send her the all clear as soon as Mom's car was out of sight. Trying not to seem impatient, I stood outside and helped her pack her bags into her Uber. After finally waving her out of the driveway, I casually strolled back into the house and reached for my phone. Patting down all the pockets of my jeans, I sighed and trotted up the steps to my bedroom. I searched through all of the usual spots I normally leave it but found nothing until I gave up and sat down at my computer instead. But it didn't turn on, and when I checked the cables in the back I found that the power cable was missing. Annoyed, I immediately went to confront Cassie only to find her waiting for me at the top of the stairs. She was wearing her favorite pair of lulu lemon leggings under a pair of tiny gym shorts that barely reached the top of her thighs, a matching pink camisole, and a pair of striped, knee-high socks. Leaning against the wooden banister with a mischievous smirk on her face, she was acting so cocky that it was obvious she was trying to piss me off.

"Looking for something?"

"Give it back."

Innocently batting her eyes, Cassie replies, "Give what back? I don't know what you're talking about."

Quickly losing my patience, I take a menacing step forward threaten, "If you don't give them back now I'm going to stuff you in the hamper again."

Playfully laughing while jumping back a few steps, she held her hand out and continued, "If you do that you'll NEVER find them."

My mind was of a singular purpose, and the thought of getting blocked by this little brat almost drove me to follow through on my threat. But instead, I listened while offering the most intimidating glare I could muster.

"I'll give you your phone and cable back, and I'll stay out of your way while you and Jessica make out all weekend...if you'll do a challenge video for my Youtube channel."

I rolled my eyes and groaned, "What kind of challenge."

"Follow me." Cassie skipped down the hall with a hyper, peppy energy that was nauseating.

Begrudgingly I chased after her until we both stood in the center of her room next to a chair she'd taken from the kitchen. Motioning for me to sit, Cassie watched me eye up the items gathered on her desk and answered my question before I asked it.

"It's an escape challenge. You get ten minutes to escape, no matter what you'll get your stuff back. But if you don't, you'll have to be my assistant in the next video."

There were only two lengths of jump rope, an almost entirely spent roll of duct tape, and a couple of zip ties, which seemed pretty much par for the course based on the escape challenges I've seen. Anxious to get this over with and confident I'd escape within seconds, I huffed and hawed over how stupid this all was while sitting down in the chair. But Cassie ignored me while busily going to work with what she had, tying my wrists to the arms of the chair with the jump rope. Moving behind me, she snaked the zip ties through the belt loops of my jeans and ratcheted them as tightly closed as she could manage until my hips her locked in place. Waiting for her to reach for the duct tape next, I kept looking from it to the monitor. Watching the scene play out from the camera's point of view, I caught Cassie trying to silently slide her sock from her leg.

"What do you think you're doing with that?" I start pulling on my wrist restraints and try to stand up, "Oh hell no, get away from me!"

Cassie tried to shove me back down by the shoulders but couldn't manage the strength, so she instead hopped on top of my lap to keep me seated in place, "Hey, stop! I'm not done yet! Hold still!"

"No! Cassie, I said n-no, no-mmmpph. Nummgggfff! Stofff! Caffeee stofff! Ugh mmm goff!" I coughed and gagged on the wadded up ball of wool and sweat, trying to push it away with my tongue.

"Mmmmmm! Doesn't that taste so good?" Her legs were wrapped around my torso to keep herself latched in place while I kicked and tested the zip ties anchoring my hips.

"Gnngg mmm mmmf! Gmmmff mmmff mm!" I was too disgusted to think straight, and played right into her trap when I spent the next few minutes sputtering and gurgling ridiculous sounds to the beat of her favorite pop songs.

Meghan Traynor's 'Lips are Movin' began to play, setting up a groan inducing joke from Cassie, "Your lips aren't moving anymore, are they?"

With one hand over my stuffed mouth, Cassie reached with the other into one of her desk drawers, revealing a brand new roll of silver duct tape. Singing along as she steadily wrapped tape around my face, she started to rock her hips in time to the music, and as the song progressed I realized that I was trapped in a music video. With a flourish she smoothed out the last of the tape over my mouth, standing up and strutting circles around me in a routine that had clearly been practiced well ahead of time. Once again I'd let hormones do the thinking for me, and now I'd failed as a babysitter less than an hour into my watch.

"Gnnffmm! Mmmfff nmmmff fnnnmm. Lmm mmm gmm. Lmmm mm gmmm!" I shook my head at her and the camera while trying to shout over the music, but she forced her hand over my taped mouth and held my head against her bobbing hip.

The thought of anybody else actually seeing this kept me desperately squirming through the entire video, despite knowing that it was exactly what she wanted. She's pulled off a few impressive revenge pranks against me over the years, but this was an escalation I never thought possible. I could see the angry, dumbstruck look on my face thanks to full screen view of Cassie's computer monitor, but there was nothing I could do to snap myself out of it. Always dancing in time to the music, Cassie duct taped my legs to the chair, wrapping up and down my thighs until they were strictly pinned apart. More jump rope from other desk drawers came out, and despite my best efforts she easily finished completely tying me up. By the end of the song, I was being squeezed in a tight web of tape and rope, with a homemade dunce cap strapped to my head as a finishing touch. She swaggers off screen at the final notes of the song, leaving me to awkwardly wiggle around to total silence.

"Nnmm-mm! Gmmffhmmm! Lmmm mmm gmmmm! Mmmm gmmm gnnngg ymmm!" Titled beyond belief, I rocked the chair back and forth in a fit of rage.

"Annnd...CUT!" Turning off the camera, Cassie stood in front of me with her hands resting on her hips, which were popped to the side in a sassy victory pose, "That.Was.AMAZING! Did you see the part where I did that spin around the chair, or when-"

"MMMMPHH! Mmmhmmm gnnngg gmmmff mm mmmf!"

"Oh, right. You want your stuff back."

Cassie reached back into her desk drawer and pulled out my phone, setting it on the chair between my legs, "Wow, Jessica's really been blowing you up."

"Lmmmff mmm gmmm! Gnnnffhmm, lmmm mmm gmmm rnn nmmm!" I demanded she let me go like we agreed, already knowing that she never said she'd let me go if I failed.

As I expected, instead of letting me go, she used my missing power cable to reinforce the zip ties keeping my hips held to a vigorous wiggle. As she expected, I didn't take this well, and for the next two hours she watched me struggle while editing the video, "If you don't tell me, I'm just going to tickle it out of you."

Without looking away from the screen, Cassie peels off her other sock with her toes, scrunching it up and rubbing it against my face. With one foot planted over my face to keep her sock pressed against my nose, her other foot dug into my ribs and sent me into a ticklish spasm.

She cued the next song on her list, and I was forced to endure an unending chorus of, "Who runs the world?! Girls! Girls! Who runs the world?! GIrls! Girls!"

"Now, what was that about stuffing me in the hamper?"

"Nnn-mm. Nmmphh! Nmm-mmm! Dmmmfff ymmm drrr! Gnnffhmm! Gnnffhmmm lmmm mmm gmmm!"

"Take a nice, big, deep whiff, because that's what you're gonna be smelling all weekend. Doesn't that sound like fun!?"

"Nmmff mm dmmff. Nnn-mm. Nmmm!" I could feel my phone vibrating against the chair as I bucked around, and could barely make out that it was Jessica calling.

Trying to block my vision with her foot, Cassie unleashed her full brat and proceeded to grind my pride into dust, smothering me into muffled grunts of disgust while laughing at my attempts to answer the phone.

"Should I get that for you? You look a little too tied up to talk right now." Without waiting for an answer, she picked up the phone and leaned back in her chair, propping both of her feet against my face.

"Hello?"

"Mmmfff! Nmm-mmm mmmmfff! Mmmmfff mmfff mmff! Mmmmfff mmmm mmmm mmmm mmmmmm gnnng ymmm fmmmf!"




To Be Continued?

gaggedbyawoman
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Post by gaggedbyawoman »

Wow :P such a great story so far :D maybe in part 2 can 1 of the girls be wearing leather leggings???

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The skeleton Beam
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Post by The skeleton Beam »

A really great read ! :D It seems he may Be in for a Looooooong Weekend of " fun ", Look forward to the next part, thanks for sharing !

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Post by guardian741 »

Fantastic story!
One of my favorites to-date. Reminds me of Infmed’s style if you ever read his stuff.

This has everything i love in it and i hope the next chapter continues the same way! Sounds like he’ll get real familiar with Cassie’s feet!

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Post by GameOverGuys »

guardian741 wrote:
2 weeks ago
Fantastic story!
One of my favorites to-date. Reminds me of Infmed’s style if you ever read his stuff.

This has everything i love in it and i hope the next chapter continues the same way! Sounds like he’ll get real familiar with Cassie’s feet!
Funny you should say that, because that was my old account before I made this one. I'm glad you're enjoying it!

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Post by guardian741 »

Dude!!!
You’re my favorite author ever!
I was super bummed when you vanished off of deviantart!

Anyway, very excited about this story and future ones! Would love to chat sometime!

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The skeleton Beam
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Post by The skeleton Beam »

GameOverGuys wrote:
2 weeks ago
guardian741 wrote:
2 weeks ago
Fantastic story!
One of my favorites to-date. Reminds me of Infmed’s style if you ever read his stuff.

This has everything i love in it and i hope the next chapter continues the same way! Sounds like he’ll get real familiar with Cassie’s feet!
Funny you should say that, because that was my old account before I made this one. I'm glad you're enjoying it!
Was about to come back to comment something similar :D ( I thought the writing style seemed familiar ) anyway, just want to say then, love your work and hope your doing well, and can't wait to see what else you dish up lol

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Post by harveygasson »

Fantastic start!

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Post by GameOverGuys »

Babysitter Bondage Bet Pt II.



"Josh? He's all tied up at the moment. Wanna see?" Cassie smiled as she idly curled her chestnut hair around her finger.

To make herself more comfortable, Cassie had tipped my chair onto its back so that I was staring up at the ceiling, or at least I would have been if her feet weren't roughly kneading my face. When I tried to shout for help, she'd slide her soles over my nose or pinch it shut between her toes to smother me into total silence. I couldn't hear a word that was being said with her music playing in my ears, but I could feel her shaking with laughter when my grunting tickled her feet. In between songs I could hear Jessica gushing over the pictures Cassie had sent, complementing her on "finally shutting me up". When I wasn't being smothered, I was trying to push the sock out of my mouth and gagging on the taste to the delight of both of them. Emasculated at the hands of a girl half my size in front of my girlfriend, I stopped trying to peek out from around Cassie's soles and let them hide my bright red face.


Cassie dragged out the conversation as long as she could while casually torturing me, going so far as to invite Jessica to a video call so that I could see the look on her face as she watched me grunt and grovel. I had to listen to Meghan Traynor and Beyonce for what felt like another hour as the two of them brainstormed ideas on what to do with me for the weekend, intermittently pausing to tease me over the way I was squirming or to imitate my noises of disgust when I'd find another pocket of flavor in my gag. By the time Cassie hung up the phone, I was too exhausted to manage anything more than impotent writhing while I watched her root through my history and contacts.

Leaning forward in her chair, Cassie propped her elbows on her knees and rested her chin the palms of her hands, spreading her toes over my face so I could see her smirking down at me, "Give up already?"

She nodded my head for me before reaching for my socked soles, "What if I gave you some motivation?"

As soon as her fingers touched my feet I began thrashing against my bondage, "Nnn-mmm! NNNNNNHMMMHMMHMMHMMHMMHMM! NMMHMMM! NMMHMM! MMMMMMMMMHMMMHMMMMHMMHMMHMMMHMMMMHMMMHMMM!"

"Tickle, tickle, tickle! Oh that's much better, I knew you had it in you!" Her toes dug into my ribs and under my arms, bringing me to tears as I howled through my gag.

"Poor, Josh. All tied up and nowhere to go. Maybe this'll teach you not to mess with me anymore, hmm? What do you say, bro? Who runs the world?"

Even if my mouth wasn't stuffed and I wasn't tickled into breathlessness I wouldn't have said it. The answer Cassie was looking for was playing in my ears again, cued up by her just to hammer her point home: Who runs the world?! Girls! Girls! Who runs the world?! GIrls! Girls!

"Oh right, you can't answer because my dirty sock is in your mouth. Here, I'll let you 'study' for a while, but we have to start getting ready for people to come over." She nodded her head in time with me shaking mine, standing up from her seat and dragging me to her closet.

She had the song repeating the same ten seconds over and over again so that i was listening to the chorus on an unending loop. I was confused when she started to untie me from the chair, but quickly realized what her plan was when she opened the lid of her hamper after painstakingly trapping me in a degrading hogtie. Trading duct tape for jump rope and pantyhose, I was ungracefully wrestled into a strict web that left me helplessly rocking back and forth on my stomach. I didn't make it easy on her, but there was also nothing I could realistically do. She was careful to never give me a chance to escape, and when she was finished she proudly stood over me with her foot triumphantly pressing down where my wrists were tied to my ankles. With one hand on her hip and the other on the hamper's lid, she gleefully listened to me protest until finally forcing me inside by tipping the hamper over and rolling me in.

I tried to hit her with me knees, my elbows, anything to wipe the smile from her face while I was stuffed up to my shoulder in her dirty laundry so that only my head was sticking out, "Ha! How do you like it, huh?! Here, have a new hat."

She pulled a pair of her panties over my head so that my nose was trapped in the crotch, taping it in place before shoving one of her gym shoes over my mouth after that, "Mmmff mm gnnndd, MMMFF MM GNNNNDD. Nnngg gnnndd mmmff fmm grmmff! Mm-mmm gnnd...mmmmmfff!"

"That's it. Nice, and, tight!" Cassie wrapped more tape around the shoe, sealing it place over my hooded face.

As if the new smell wasn't bad enough, she danced her fingers across my neck to tickle me into another fit of squirming, but was stopped short by the doorbell. Even as a sense of relief passed through me when she left to answer the door, I knew it wouldn't last long. Assuming Jessica had come to personally tease me face to face, I urgently called after my sister when she closed the lid on the hamper and left to answer the door. Trapped in a wicker basket of sweaty socks and worn leggings, I was left to helplessly wiggle around like a helpless damsel in distress while my senses were assaulted on every front. I tried dislodging Cassie's sneaker from my face, tipping the hamper over so I could wiggle out, but none of it worked. I couldn't see a thing, and with the same lyrics repeating in my ears it became impossible to tell how much time had passed. When the lid was finally lifted again, it wasn't Jessica and Cassie looming over me as I expected, but Cassie and two of her friends.

Covering their mouths with their hands while giggling at me, the girl's stared with wonder as I threw my head around, "Mmmmff! Mmmmm-mmmmm mmmmm! Hlllff mmmm! Lmmmff mmm gmmm!"

My sister stood between and behind them while watching our reactions, "Maria, Chelsea, this is my loser brother, Josh."

"Oh my God! Cassie, you're hilarious!" Chelsea kept fussing with her blonde hair while bashfully inching closer.

Maria wasn't so shy, and giggled as she playfully shoved my head, "What do you think he's trying to say?"

"Lmmmff mmm gmmm! Lmmmff mmm gmmm, llmmm mmm gmmm."

Cassie cupped a hand to her ear and bet over at the waist, "I...think he's singing along to the song."

"Nmm-mmm! Nmmm mmm nmmff!"

"What's in his mouth?" Chelsea pulled out her phone and started taking pictures, raising her voice over the sounds of my displeasure.

Cassie gripped my jaw and squeezed my cheeks, "Josh is eating a nice, big, yummy sock I was wearing when I tied him all up. Isn't that right, Josh?"

"Fmmmff ymmm! Gnngg mmmff mmmmff mmm mmm!"

While Maria and Chelsea treated me like a new toy to play with, Cassie unzipped a duffel bag they'd brought over with them and squealed with delight, "Chelsea, I LOVE it!"

When I saw Cassie unfurl a cheerleader uniform about two sizes too small for me, I began thrusting and thrashing so hard that the girls watched me tip the hamper over and spill out onto the floor. The full extent on my bondage revealed, they burst into a loud gaggle of giggles while kneeling down over me to test them. They rolled me around on the floor and quizzed Cassie on where she learned to tie people up and if she could teach them. And teach them she did. Easily keeping me pinned by sitting on top of me, the girls had blast wrestling me out the rope and my clothes until I was sporting a skirt and sleeveless top.

It was more than just a skirt and top they stuffed me into though. In a new low, a pair of pantyhose were forced up my legs along with a pair of knee-high socks. A bra was fastened in place and filled until I had a giant pair of fake breasts sticking out in front of me. A long, blonde haired wig was snugly fastened on top of my head, and a pair of pom poms were fastened to my wrists. When they finished, I was left awkwardly standing in the middle of the room, my pom poms bristling behind my back as I looked in my sister's mirror horrified. My midriff was left exposed, the full length skirt on them was a mini skirt on me, and was barely long enough to cover anything at all. They all stood in a circle around me laughing, recording my reaction to seeing myself turned into a cheerleader. I would've spent the weekend stuffed in Cassie's hamper over this, and was so embarrassed that I tried to hop away towards my room.

"Where ya goin, pretty girl?" Maria gripped the jump rope keeping my elbows pinned together and made me hop back in front of Cassie's computer.

"Wait," Chelsea adjusted my fake boobs and brushed the wig's hair out of my face, "I think he needs a touch up."

"Nmm-mmm! Nmmm! Nmmfff mmm dmmm!"

Cassie straddled my lap while Maria held me down by my shoulders, providing a Chelsea a semi stable canvas to work on, "Look how excited Josh is, he can't sit still!"

"What's wrong, got ants in your panties?" Maria teased.

"Your panties aren't too tight are they? Maybe you'd fit better in a pair of Mom's?"

"When he's ready let's have him practice doing cheers outside!"

"Stop getting him all riled up, I'm trying to make him pretty!"

"MMMMPPHH! Mmmmfff mmmmfff mmmmm! Nnnggg gnnnd nmmmm nmmfff lnnff mmmfff. Nnnmmfff...nmm-mmm....nmm-mmm."

It was an immeasurably emasculating experience to be held down and caked in makeup while being taunted for the sounds I made, and it ended with a pair of bright red lips being drawn on over the duct tape plastered over my mouth. When they were finished they stood me up in front of a mirror and forced me to take a long look at myself. Maria, in her skin-tight spandex leggings and crop top leaned against me with an arm on my shoulder while Cassie leaned on me from the other side, both of them ignoring me as I shimmied my shoulders in an attempt to shove them away. They each inserted an earbud into one of my ears, and kept me standing in front of the mirror while picking out cheer routines to make me listen to. Unable to take my eyes off the train wreck that was my outfit, I pulled my eyes shut and let out a long, frustrated groan, cursing my sister and her friends while they high fived each other to the sound of peppy pop music...

To be continued?

gaggedbyawoman
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Post by gaggedbyawoman »

I can't wait for part 3 :) this is so good.

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Post by gaggedbyawoman »

I can't wait for part 3 :) this is so good.

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Post by guardian741 »

SO Good!
Would love to read a continuation!

Should he smell & “appreciate” the girls cheer shoes?
Does a friend visit and get roped-in to being a footstool as well?
Does his girlfriend come to visit?
Foot-rubs all night?

Friendly reminder: your work is my favorite!

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Post by The skeleton Beam »

Awesome ! love the cheer outfit, the humiliation will only continue now I imagine :lol: thanks for update !

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Post by Bondwriter »

Great story so far. One shouldn't make bets with devious siblings ...

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Post by slackywacky »

Bondwriter wrote:
1 week ago
One shouldn't make bets with devious siblings ...
Isn't that what siblings are for? :-)

Good story, thank you for posting.
Thanks for reading. Feel free to comment.
Slackywacky aka FH.

My active stories: Story catalog: All my stories

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Post by sockgaggedsissy »

This is very good!

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