Family Chastity Story Ch 03

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+.

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My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I first unlock him from his restraints -he is kept tied spread-eagle to his bed every night. Sometimes naked, sometimes in his rubber gimp suit. Once he's unrestrained and stripped naked, I then have him bend over his bed so I can insert the electric prostate-stimulating butt plug. With it firmly in place, he dutifully heads to the bathroom and sits on the toilet like a woman.

Within a few minutes, the electric butt plug works its magic on his prostate, and thick, white cum begins to drip through his chastity device. I love the sound it makes as it slowly drips into the water! And the frustration in his face as he's slowly milked is so satisfying! He gets absolutely no sexual relief from these releases, but they are not painful in any way -just totally involuntary and unfulfilling. After leaking a month's worth of cum into the bowl, I make him stand up and flush away his filth. I enjoy making him watch as his cum is slowly flushed away.

Besides giving me enormous pleasure, these releases keep him healthy and allow his tiny chastity device to remain on permanently with only the occasional cleaning. He, of course, is restrained for these cleanings. During these cleanings, I have also been rubbing Estradiol cream on his tiny cock and balls -all without his knowledge. While he is blindfolded, I rub the estrogen hormone cream all over him. The side-effects have been amazing! I swear his little member has been reduced to a two inch nub.

Today just so happens to be the first day of the month and I have decided to mix up the routine.

I enter my sissy son's bedroom and walk past the girly decor towards his bed. He is as I left him. Tied spread-eagle to his bed, wearing only a pair of pink latex panties and matching bra. The metal cage of his chastity device can be seen bulging against its latex confines. My sissy son is blindfolded but can hear me walking to his bed. I quickly dispense with the restraints and blindfold. My dutiful son then kneels in front of me.

Me: You know what today is. Ready for your release?

Him: Yes mommy. It has been so long. I...I...need this so badly mommy. Do you want me to bend over the bed?

Me: No, not yet dear. Change of plans. Mommy has some good news.

Him: What? But today's the first. I'm always milked on the first day of...

Me: Not today. Today we are going to play a little game.

Him: Game? What game?

Me: A little game I devised. You're gonna love it. Something to entertain us both.

Him: Okay... (I sense some hesitancy in his voice.)

Me: First things first. Stand up and pull your panties down.

My gimp son stands up and slowly pulls the latex panties down to his ankles. The tight latex squeaks as he peels them from his skin. Out pops his little caged cock.

Me: Okay, spread your legs and put your hands behind your back. Don't you dare move.

Him: Yes, mommy.

He complies with my instructions. I approach him and kneel in front of him. Using the key off my necklace, I unlock his cage and remove it. I glance up at him and see him hungrily staring back at me. Immediately, his little cock stands at attention, desperate for even the slightest touch.

Me: My my my. Aren't you excited?

Him: Sorry mommy! I can't help it.

Me: That's right. Apologize.

Him: It's just been so long...

Me: Well, you're going to have some fun today. Your cage is going to stay off all day!

Him: Really?! Oh my god, mommy please...

Me: I thought you might like that. All day. No cage. There is just one small catch...

Him: What's that mommy?

Me: You'll see. It's all part of the game.

I go over to the side table and grab my bag. Kneeling back in front of my sissy son, I pull out a large tube of ointment and latex gloves. With the latex gloves now on, I squirt a large glob of the ointment onto my hands. I quickly begin rubbing my son's cock and balls with the white cream.

Him: What's that mommy?

Me: This cream is a numbing agent. Works for over six hours. Makes everything totally numb.

After about a minute or so of applying multiple coats, I stop and glance back up at my sissy son.

Me: Do you feel anything down there dear?

Him: I'm not sure mommy. I don't think so but...

Me: Feel this? (I whack his balls with the palm of my hand.)

Him: Ahhh...no...nothing. Not a thing. (He seems a bit shocked.)

Me: Perfect. Hopefully this will last all day. For your sake. Now for the fun part...

I reach down into my bag and pull out a large metal tool. It looks like a pair of specialty pliers holding a tiny green rubber band at one end. My hand wraps around two red, rubberized grips at the other end of the tool. As I squeeze the grips, stainless steel levers on the other end force the green rubber band to slowly open -forming it into a large circle.

Me: This, my sweet son, is an elastrator. They are used to castrate farm animals. Today I am going to use it on you. This little rubber band is going to go around your scrotum. Once in place, it will slowly cut off the blood flow to your testicles. If on too long, the effects may be...well... But regardless, many men find that it brings them pleasure. After all, I did find this tool in a sex store.

Him: I am not so sure this is a good idea mommy...I thought we were going to play a game but this-

Me: This is the game sweetheart! Well part of it, anyhow...

Him: But I don't want to be castrated!

Me: Oh don't be silly! That won't happen! It is just a fun little game...

Him: Fine. What's the game?

Me: A simple series of tasks. That's all. I will explain it later in greater detail. But first, we need to get this on you. (I tease him and jiggle the elastrator in front of his face.)

Him: Mommy, I don't want to play this game. Please, do I have to?

Me: No you don't have to play, dear. It's entirely your choice. I should have made that clear. There is another option.

Him: What's that?

Me: You go back into your chastity cage, I put the prostate massager in you, and you get milked into the toilet. Just like normal.

Him: I would prefer that mommy please.

Me: Are you sure? But you don't know what happens if you WIN the game today.

Him: What?

Me: All games have rewards if you win them. If you win today's game, you will be rewarded.

Him: With what mommy?

Me: Simple. If you win, the elastrator band will be quickly removed. There is no risk with wearing it for a few hours. And then...no more chastity cage for the ENTIRE month! It stays off! You can even jerk your little sissy clit as much as you want. Real orgasms for the entire month. No strings attached.

Him: Really?! (A smile begins to form on his face.)

Me: Yes. How long has it been since you had a real orgasm? Six months? A year? You've been having these sad prostate orgasms for months now. Don't you want to cum like a real man?

Him: Yes mommy! More than anything!

Me: Then you still don't want to play my little game?

Him: I...I...

Me: The chastity cage is right here. I can put it on right now and we continue with our routine...

Him: I want to play.

Me: Are you sure? There is no turning back once the elastrator band is on.

Him: Yes. I want to play mommy!

Me: Excellent! I knew you would. Such a brave little sissy! Let's get started! Now hold still.

I kneel in front of him with the elastrator tool in my right hand. With my left hand, I grip his balls and tug at them, pulling them straight down. I carefully tighten my grip on the elastrator tool and force the tiny, thick rubber band to open. Once sufficiently wide, I guide my son's balls through the narrow opening. I pull them all the way through, and when satisfied with the green band's new position, I begin to ease my grip on the tool. The green band slowly tightens around the scrotum. Eventually, all the tension in tool is released and the little green band pops off the stainless steel tool. With the green band now free, I toss aside the elastrator tool and look at my handy-work. A tiny, green band is now firmly in place around my son's scrotum just above the testicles. I can already see the testicles begin to change color from the decrease in blood flow.

Me: Wow! You are taking that like a champ. How does it feel?

Him: I don't feel anything mommy. The numbing cream...are you sure my balls are safe?

Me: As long as the band is removed soon.

Him: You said I had a few hours...

Me: Did I? Well, I guess a few hours is okay. We'll have to wait and see. Now put your panties back on.

Him: Yes mommy.

He reaches down pulls the latex panties back up. They squeak as they move up his legs. Once in place, he releases them, and they snap right in place. The super-tight latex gives him an almost smooth front. You can hardly see his bulge. His little cock is now out of sight and out of mind. Perfect.

Me: Now for the rest of your outfit...I want you to wear these.

I hold up in front of him a pair of patent leather pumps. He quickly puts the high heels on and fastens them in place with ankle straps. I then hand him a pair of leather bondage mitts for his hands. I help put each one and lock them in place. His hands are now tightly confined and basically reduced to useless nubs. The outfit is completed with an ultra-feminine rubber face mask that I fasten tightly around his head. Little eye-holes allow him to see through the hood.

Me: Follow me upstairs dear. Then we can get started. I am so excited!

We both go upstairs and I lead him to the bondage room I have set up. This room is normally used for filming bondage clips for our website. But today I have re-purposed it for our little game. The walls and floor of the room remain covered in black rubber sheets. The room is lit with harsh overhead lights. Mounted to one wall of the room is a large flat screen television. I close the door once we are both inside.

Me: The objective of today's game is for you to cum. Once you cum, the game is over and the little band around your balls comes off. It's that simple.

Him: That's it? I just need to cum?

Me: Yep! That's it. Just cum. Should be easy really. You haven't cum for real in months.

Him: Yes! Can we start? I want this band to come off ASAP!

Me: Absolutely! First, let's get you tied up.

Him: Tied up?

Me: Yes. Don't worry...it's all part of the game. Here, come stand in the middle of the room.

My sissy son walks in his heels to the center of the room. We have filmed many scenes in this room, so he knows what is coming. I quickly fasten each ankle to large, upside-down U-bolts in the floor. The two restraints are spaced far apart -spreading his legs wide. I then stand up, and with the help of a foot stool, secure his wrists to similar bolts in the low-hanging ceiling. Confident that all the chains are secured, I stand back and admire my handiwork. My sissy son in his latex bikini and mask now stands before me, spread out like an "X". He totters in his high-heeled shoes as he adjusts to his new position. On the wall opposite him, about 5 feet away, is the flat screen television.

Me: Ready?

Him: Ready for what? I mean...how am I supposed to cum?

Me: I am sure you will find a way. Now dear, mommy is going to leave you tied up here for 2 hours. You have those two hours to cum in any way you can. When I come back, I will release you and free your balls. If you haven't cum in those two hours...well...we are just going to have to find another way.

Him: Ummm...I'm confused mommy. (He starts to slowly test his restraints. He can hardly budge against them.)

Me: How so?

Him: How am I supposed to cum? My cock is stuck in my panties. I need something...

Me: You better find a way my little gimp. But don't worry, there will be a stimulant...of sorts.

Him: Ok mommy. I'm just a bit worried...

Me: Oh enough!

I reach over to the wall and pull off a ball gag hanging there. In no time, I have the red ball stuffed in his mouth, and the leather straps fastened around his hooded head.

Me: That's better. No more talking. You are running out of time. Two hours to cum starting now. For your sake, I hope you cum.

Speech over, I turn on the television and walk out of the room. On the television plays a recording of the Victoria's Secret Fashion Show on an endless loop. On the TV screen, scantily clad models in lingerie walk up and down the catwalk. My sissy son hasn't seen anything so stimulating in a long time. He is normally prohibiting from watching anything like this.

I also neglected to tell him that the webcams in the room are all active. I have installed four webcams in the four upper corners of the room, right below the ceiling. Normally we use them for webcam shows for various clients. Today, I turned them all on and am broadcasting them live on the internet. I am watching them right now on my phone. And what a sight!

My little gimp son is trying desperately to get off! Although his hands and ankles are completely restrained, he is trying in vain to free himself! I watch for a few minutes. In addition to the sound of the VS Fashion show, I can hear him struggling away. His moans and grunts are delightful. After a while, I grow bored, and decide to head out and grab a quick lunch with my friends.

At the café with my girlfriends, I decide to check my phone again. He's still going at it! What a trooper. I watch him continuously hump the air over and over. He's trying to get some friction against his little cock, anyway he can. He's fixated on the television screen, his eyes hungrily watching the beautiful models strut in their thongs and G-strings. I pass my phone around to my friends so they can have a look. While the phone is passed around, my sissy son starts to arch his back and rhythmically thrust. We all burst out laughing. He is clearly trying to get his little cock to rub against his panties. He does this for over ten minutes straight with apparently no success.

Back at the house, I change into shiny, black leggings and a pair of leather boots. I put on a simple t-shirt with its waist tied in knot. I look at my watch. Oops! Over two hours has passed! I forgo checking the webcams on my phone, and walk straight to the bondage room and open the door. The television is still playing the VS fashion show -I imagine for the fifth time. My sissy son is still standing in the center of the room, fully restrained. When I walk in, he is slowly gyrating his hips in a circular fashion with his eyes gazing at the television screen. His body is covered in sweat. He is clearly enjoying this. Somehow.

Me: Any luck?

Him: Hmmmph! (He drools around his ball gag.)

Me: Is that a no sweetie? Well, let mommy check.

After turning off the television, I walk over to him, and with one finger, pull back his panties and look inside. The pink latex panties are filled to bursting with precum. As I pull them back, precum oozes out and down his thigh. But no cum. Just tons of precum, a tiny cock, and light purple testicles.

Me: Oh no! I see no cum for mommy. What a waste! Two hours down the drain. You are running out time dear.

Him: Hghhrrbbh!!

Me: Oh sorry. My mistake. (I reach around his head and undo the ball gag strap. It falls to the ground.)

Him: MOMMY PLEASE!! Take it off! Take it off!

Me: But you didn't cum, honey. You had two hours. That was the deal. Now look where we are.

Him: I couldn't! I couldn't!

Me: Does it hurt? Are you in pain?

Him: No but...

Me: Good, the numbing cream is still working. I was afraid it had worn off.

Him: But...but if the elastrator band doesn't come off soon...

Me: Well whose fault is that?! This is a game, dear, and you are losing. Keep losing, and you may lose something permanently.

Him: It's not over?

Me: Not even close. You haven't cum yet. There is still something else I want you to try. You get another chance!

Him: Ok. I'm ready. What is it? (I can sense the eagerness in his voice. He knows he is running out of time.)

Me: First, let's get you out of these restraints and out of these panties. You've soiled them with all your precum.

I retrieve the footstool and unbuckle his wrist restraints from the ceiling. I then kneel down and do the same to his ankle restraints. My sissy son hobbles free, barely able to walk in his high heels. I quickly put everything away and approach my son, now anxiously pacing around the room.

Me: I would ask you to take your panties off, but your hands are still in those bondage mitts. So...come here, and let me.

Him: Yes mommy.

He comes to me and presents himself, placing his hands behind his lower back. I grab the sides of his panties and pull down hard. The underwear slowly peels off him, squeaking as they are pulled down his hairless thighs. They are covered in precum. Once on the ground, I direct him to step out of them. Now he is completely naked apart from his pink bra. I notice him glancing down, inspecting his balls. They are turning an unnatural shade of purple. I can see his eyes widen through his doll mask.

Him: Ok what's next?

Me: One final game. The objective of this game is the same as the last one. Cum. That's it. Cum and the game ends. I take your elastrator band off, and you have a month out of chastity.

Him: No catch?

Me: No catch. But I didn't say it would be easy. Now get on all fours.

Him: Yes mommy.

He lowers himself obediently and gets on his hands and knees. He eagerly looks up at me, waiting for the next instruction -like a loyal puppy.

Me: Now stay right there. Mommy has to set some things up. But first, I don't want you peeking.

Off the wall, I grab a fuzzy, purple blindfold and put it over his eyes. Next, I go to the toy crate and pull out a large, heavy cardboard box. Inside is a special toy. I open the cardboard box and remove the packing material to reveal a gigantic dildo. This monstrosity had to be special ordered and is called the "Anaconda." Made of heavy silicone, this toy is about 20 inches long. It widens rapidly, just past the tip, to about 6 inches in circumference. It continues to grow all the way to its base -which itself is a massive 10 inches around!

I carefully remove this massive dildo from its box and carry it with two hands to the wall right behind my gimp son. The base of the toy has a large suction cup which I use to attach it to the wall. I place it just over a foot off the floor. It protrudes menacingly from the wall into the room. I lastly rub some lubricant over it -making it all shiny. All finished, I glance over at my little sissy kneeling on all fours.

Me: Now my little sissy, I bet you are wondering what I was up to.

Him: Yes mommy.

Me: Before I take the blindfold off, I want you to know the rules of this game. First, you must remain on all fours. Under no circumstances can you get off the ground. Second, under no circumstances can you touch your little cock. If you dare touch it, the game ends, the elastrator band remains on forever. Third, you win the game if you accomplish one of two things... you cum or take the whole thing in your ass.

Him: What... thing? (I can sense the fear in his voice.)

Me: You'll see. No more interrupting. Now, there is no time limit. Feel free to take as long as you like. But as warning, based on the color of your balls, you may want to hurry. Any questions?

Him: No mommy. I'm ready.

Me: Wonderful! Now back your ass onto this dildo and have fun!

I walk over to him and rip the blindfold off his head. He nervously cranes his neck to the side and glances back at the beastly dildo behind him. His jaw drops at the sight of it. I don't blame him. He cautiously backs up on his hands and knees until the large, blunt end of the dildo is just touching his ass.