Timmy's Torment Pt. 04

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Timmy's chastity fun continues.
2.8k words
4.56
6.9k
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Part 4 of the 11 part series

Updated 06/14/2023
Created 05/21/2020
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We ended up spending the evening outside. My dad joined us midway through dinner and he and Beth spoke the most. Although the meal was uneventful, I would occasionally catch Mindy looking down at my crotch, and then looking at Beth like she was the cat that got the cream. This gave me joy. I imagined it drove her crazy, like having an itch she couldn't scratch. I was in heaven.

My joy soon faded when it came to turning in for the night. Beth was too "fucked out" to play anymore. So my plan on torturing Mindy some more had been scuppered. Instead Beth and I are both naked in bed spooning. My plastic cage pressed against her ass cheeks and my hand resting on her waist.

She's already asleep and I'm wide awake. My cock refuses to settle, every time I close my eyes I see Beth being satisfied by the sleeves. Every time my cock tries to break free, the cage yanks on balls. The torture of spooning Beth is too much and roll onto my back and begin to massage the base of my poor balls. That's when I start to hear the moaning. I walk over to my bedroom door and crack it open slightly. Mindy's moans fill the hallway.

"She's doing that deliberately!" I whisper to myself angrily.

Refusing to listen to Mindy's theatrics, I grab a pair of boxers and a tee shirt and my robe. Carefully sneaking out of my room, across the hallway and heading downstairs for some peace.

I brew myself a herbal tea and search the web for tips on how to cope with chafing in a chastity cage. Some say "lube" some say "coconut oil" but they all say "no ice!" Since I have neither, I guess I'll settle for the night's cool breeze on my testicles while I drink my tea.

"Well hello, Cinders." Chirps Mindy as she joins me out on the deck.

"For fucks sake!" I groan.

"Well now that isn't nice is it, Cinders?" She exclaims, while lighting a cigarette.

"What the fuck do you want, Lady Tremaine?

Mindy pulls a confused face as she breathes out her cigarette smoke.

"It's Cinderella's wicked step-mother's name." I scoff.

"Well aren't you a clever little boy." Mindy scolds. "Anyway, I'm glad you're still up. I wanted a word with you about your totally inappropriate behaviour with me earlier."

"You have got to be kidding?"

"Not at all."

"You call me fucking Cinders. You bully and belittle me. You ridicule and humiliate me and the one time, the one time I truly stand up for myself, and that's inappropriate?"

"Exactly. Not only am I your elder. I'm also your stepmother and the level of respect I'm owed has been found wanting recently."

"I think that's CRACK you're smoking. Mindy!"

"See, now that type of behaviour is exactly why I think you need a good old fashioned spanking!"

"Spanking?" I scoff.

Mindy merely nods as she puffs away on her cigarette.

"Mindy. With the utmost disrespect, go suck on a bag of dicks!"

"You see, I was thinking about pretty little Bethany. You made her sound like such a little size queen..." Mindy pauses as she takes another pull on her cigarette.

"So? I can give her anything and everything she wants!"

"Soooo. Yes...technically, for now you can give her what she needs. But all it takes is a *real* big dick to come along, and who knows!"

"Beth would never cheat on me!" I snarl back.

Mindy pulls a mischievous grin and puffs once more on her cigarette.

"So the thing is, Cinders. I'm a lady of leisure. That means I have a lot of free time. Now I could use this free time to join multiple dating sites and gather up a nice selection pool of guys. Now these will be super hot guys with massive dicks of course. Then I could make a couple of Snapchat or Instagram accounts and forward all that information on to dear little Beth."

"You're psycho, you know that? Besides that shit won't work. Everyone knows women hate dick pics!"

"Hmmm...But do we though? Now don't get me wrong, your average Joe's dick pic, will lead to disgust. You know, ordinary...mundane...basic! But you send over a massive schlong...Well now you're cooking with gas!"

"Beth would never be into..."

"Now as I said, a basic dick, yuck! But a big, thick, veiny monster...yummy. We may pretend we're disgusted, at first. We'll even show a friend like, URGH! But we're actually just gauging their reaction. Is it the same as ours? Because secretly, when we see a big ol dick. We're really thinking...is it real...Could I wrap my hand around it...Could it fit in my mouth...could I really take such a beast..."

"I can match any dick you send Beth's way!"

"Hmmm...yes. But it's not the same, is it? Your little toys...sorry, your big boy toys! Don't cum! You don't get the warmth of his cum inside you. You don't get the warmth of his flesh inside you. You don't get that...real feeling...and trust me, Beth will want that real feeling!"

"So what, if I let you spank me you'll leave my girlfriend alone? This is such bull! What's your problem? Why can't you just leave me be?"

"Honestly, I may still mess with your girlfriend regardless!"

"Why?"

"Because why the fuck should you get everything and I'm left wanting?"

"WHAT?"

"Oh come on! You just happen to find a random girl who's into your little beta male chastity cuck fetish and lives happily ever after? Fuck that! You're a little fucking sissy and why the fuck shouldn't I toy with you?"

My anger bubbled at the surface. Mindy is a bitch. She wants to ruin my life just because I'm happy? Then it hit me. I'm happy!

"Listen, Mindy. I know, we both know, there isn't a damn thing I could say or do to stop you trying to fuck me and Beth up. So do what you gotta do."

"Really? No fight left in you?"

"Nah. Especially not with you. I mean, this legendary dick you're going to find. Maybe a couple of weeks? Then the accounts and shit you gotta set up to catfish Beth. Possibly what a month? Then what? She get super horny all the time? I'll fuck the shit out of her, and if that ain't enough? Then fuck it, she can cuck me! It'll be a dream come true!"

"You don't mean that."

"You know what, Mindz. I do! Because I'm happy, unlike you! Goodnight evil stepmother, hope you have a torrid night!"

And with that I smugedly walked away and back to Beth, hopefully leaving Mindy in a defeated state.

"Morning, sleepy head." Beth greets me as I sit up in bed.

My mouth drops as I'm blurry vision becomes clear. Not only is Beth completely naked, wearing only a strap-on with a massive dildo attached. She's shaking her hips causing the dildo to spin around in a circular motion.

"What are you doing?" I asked, puzzled.

Beth stops shaking her hips and grabs the dildo with both hands. Her fingers are unable to completely wrap around the toy. The toy is so big in comparison to her petite frame, she looks like she's struggling to hold it up. As she lets it go, it dangles between her legs.

"I wanted to try it on. It's very...impressive tool to have no?" She asks lifting the massive dildo back up and attempting to jerk it single handedly.

"Yeah, yeah it is."

After realising one hand wasn't enough. Beth begins to perform a double handed hand job.

"Look!" She says nodding at how much dildo. "Two hands ain't enough! You could get a mouth on the end of that too. If this was a real cock you need at least 2 people to please it!"

"I don't know if I could handle it all by myself."

"Well you've taken it balls deep. I think you'd be okay."

"Yeah, but I didn't really do anything did I?"

"Beth. YOU TOOK THAT WHOLE THING!"

"I know that! I just mean, I didn't need to suck it or jerk it off did I? You ate me and fingered me and got me ready. Then you strapped up and gave me a good dicking!"

Beth then pulls the dildo up and pushes tight against her belly.

"But it is impressive that I could take it all!"

"Yeah, Beth. You're a true size queen!"

"Size queen?"

"It's a compliment really!"

"Okay...Well this size queen wants to play."

"Sure. Take the strap-on off and I'll strap up."

"Hmmm, no thanks! I want to play with this beast while you eat my ass!"

"Oh." I said disappointed.

Beth walks over to our toy bag, with the strap-on ridiculously swinging between her thighs and pulls out her wand vibrator. She turns on the wand to her favourite setting and marches back towards me.

"Kneel."

I drop down to my knees. My face level with her monster cock. Beth turns around and backs her ass in to my face.

"Give me your hand." She orders.

I raise my right hand and she places the handle of the wand into my palm.

"Hold it tight."

I squeeze the handle and grip it tightly as it vibrates in my hand, while she adjusts my arm for perfect placement.

"Ahhh, that's the spot." Beth moans. She gives her ass a little wiggle and I begin to worship her asshole.

I slowly lick her anus in a circular motion, while she grinds her ass over my face.

"Mmm. That's it baby." She moans.

My cock starts to swell in its cage. I feel the ring tighten on my sack. Beth pushes her ass harder against me, forcing my head back.

"Fuck...I'm close." She purrs. Pushing her ass even harder.

My neck is as far back as it can go, Beth is basically sitting on my face. My body is in agony trying to hold her weight.

"I'm cumming." She screams.

She must've lifting a leg or something because the weight becomes too much and we crash to the floor. I fall onto my back as Beth crashes to the ground. The dildo pops out of the O-ring that was securing it too the harness.

"Wand. Wand. Wand!" Beth cries out. Trying to salvage her orgasm.

I hand Beth the wand and grab the gigantic dildo off of the floor.

"I need it." Beth begs. Looking desperately at the dildo.

"Okay. Where's the lube?"

"Fuck knows. Just use saliva. I need it now!" Beth demands.

Lifting The dildo to my mouth. I lick around the tip, then I sticking out my tongue and opening my mouth as wide as I can. I shove in the dildo, hitting the back of my throat, gagging instantly. I repeat several more times to generate enough to lube at least the first 5 inches of the dildo.

"Hurry!" Beth begs.

I place myself between Beth's legs and line the plastic cock at the entrance of Beth's soaking pussy. The helmet slides in with little resistance, so I push even further.

"Oh fuck! More!" Squeals Beth.

Pushing the cock half way in ans Beth lets out an animalistic grunt. I pull the dildo out and reinsert once more. Beth makes the same sound again. Pulling out the dildo but this time stopping so the head stays in, as I slide it back in, Beth's pussy basically sucks in the dildo. As the dildo becomes fully immersed, Beth legs fly up and wrap around my head, locking my arm and head in place like an old 90s wrestling move as she convulses.

Beth finally releases me from her legs as she rolls onto her side causing the dildo to shoot out of her with a plop.

"You okay?"

"Mmhmm." She mumbles.

She rolls back onto her back exposing her pussy. I wasn't expecting to see her, stretched or gaping. But it was the exact opposite. Her lips were tight together. Like they had swollen shut. I leaned in to kiss her pussy lips and she shuddered at my touch.

"Sorry." She said. "Its super sensitive right now."

"I understand." I tell her. Rubbing my balls as proof.

"Soooo, when I said saliva...I meant spit on it, not actually suck it."

"Haha, yeah that makes sense. Sorry I just went on instinct."

"It's cool. It was kinda hot to see you suck a cock for me!"

"Well it's not a real cock. So it's not big deal!" I laughed nervously.

"Well it was hot regardless. So do you want me to unlock you?" She asked genuinely.

"Really?"

"Yeah. I got gymnastic practice and then I'm going to have to check in with my folks. So I probably won't see you for a day or two." She shrugged.

"Ah shit. It's spring break, Beth. I thought it we had this whole time together."

"No chance, Tim. I have obligations. Don't you have assignments to complete? We can't just be sex crazed the whole time. Nothing would get done. So am I leaving you the key or what?"

"Don't you want me locked?"

"I mean, with me? Yeah for sure. You're 100% focused on me and I love that."

"Oh I thought you wanted me locked 24/7 and never to cum!"

"WHAT? No way. I said pussy free! You can cum in the cage with me, and I think that's hot. Especially as you cum while pleasing me. But when I'm not here you should masturbate, it's healthy. It would be weird if you didn't to be honest."

"Leave me locked."

"Really?"

"Yeah!"

"You're sure?"

"I am, Beth. I wanna stay caged for you."

"Okay, Tim. It's your penis after all."

Beth got an Uber shortly after and left for practice. I know it was silly for me to stay caged but I was banking on Beth feeling sorry for me still being locked and might make her want to meet up sooner rather than later. But Beth was right, I did have assignments to do, but first some lunch.

In the kitchen to make a sandwich and there's a note on the fridge.

*Gone hunting. Be back tomorrow

-Dad*

"Great. Just me and Mindy. That'll be fun." I chuckle to myself.

Being caged isn't ideal, but it is effective. Beth had only been gone a few hours and I had already sketched my art assignments and wrote my economics paper. What did I use to waste my time on before? Oh yes porn. There is no way it can have the same affect on me caged. Only one way to find out. I tell myself as I turn on my PC.

I must have watched a dozen pornos in the space of a couple of hours. Usually I'd spent 20-30 minutes trying to find a film that hit the spot and then I'd com like 15 seconds later. But this was intense constant arousal. Fuck I wish Beth were still here. Then it hit me. The strap-on! I can strap up and give myself a phantom hand job. It worked with that first time, surely it'll work with just me.

Sitting in my chair wearing only my cage and a strap-on. With the 7 inch dildo Beth had bought. I play my favourite cuckold video with Riley Ried and Shane Diesel, I squirt some lotion onto my hand and proceed to jerk my fake cock off.

Ten minutes of stroking and although I feel close I'm nowhere near ready to cum. I hit pause and Jump out of my over to the toy back hoping for something to help. A quick rifle through the bag and eureka! A vibrating butt plug. Originally purchased for Beth, I'm sure she won't mind me using it. She did say, I should cum when she's not there! With the plug lubed and pleasantly buzzing in my ass, I sit back down and resume my video.

Rocking in my chair, furiously stroking the strap-on, now I finally feel like I could seriously cum. The pressure is there. I can almost feel the explosion. My cage is leaking like mad, the climax is close.

"Almost there, just a little bit more." I tell myself.

As I lean back, the butt plug hits my prostate just right, and my whole body starts to seize up. As my legs stiffen my chair wheels back and swirls around. My eyes are rolled to the back of my head. My fist is furiously beating my fake cock. The plug is buzzing just right...then it happens. My cage bouncing from the pressure, shoots hot streams of cum all over my thigh as my body collapses in the chair. Completely fulfilled, that must've been the most intense, potent, earth shattering orgasm of my life.

So light headed and giddy. I couldn't tell you how long I had sat slumped in the chair. But when I opened my eyes. Mindy stood before me. Smiling ear to ear.

To be continued...

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3 Comments
AnonymousAnonymousover 2 years ago

Awesome I've been watching for updates for this series for the last year.

northirishdivernorthirishdiverover 2 years ago

spot on..although need more and longer

AnonymousAnonymousover 2 years ago

Lovely! Can't wait for the next part!

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