Family Chastity Story Ch. 02

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Big Boobs

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+.


Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distributing video clips of our adventures together. Milking sessions, peggings, spankings, foot worship…over two dozen clips so far. All of them uploaded online for viewing. Did I mention how lucrative this new project is? I am amazed at what people are willing to pay for the clips and especially for custom videos. Nothing is off limits, and I mean nothing. I am having so much fun that I have postponed his little operation –he is still intact and as horny as ever, safe and sound in his tiny chastity cage.

I have set up an entire room in my house for this project. A small, windowless room has been converted to my own personal filming studio. The walls have been covered in black rubber and adorned with a variety of whips, paddles, strap-ons, and other S&M toys. It looks like a typical sex dungeon –except for the half-dozen (or so) digital cameras and lighting tripods. I have strategically placed filming equipment around the room to capture all the angles. When I edit the videos together, this allows me to pick and choose which camera angles to use. There are also a few room microphones for audio, but this is never really a problem owing to the room’s small size.

Today we are filming a custom video for a client.

I am dressed in a sexy leather bikini. The top has tiny metal spikes over the bra cups. I am also wearing thigh-high black boots and long leather gloves. A spikey metal collar completes my outfit. I look like a mean dominatrix –just what this client requested. I am busy arranging the room, setting up the recording gear, and waiting for my gimp son to come in. He is also getting in a special outfit. Apart from this, he has no idea what awaits him today. I like to leave it as a surprise for him. Today especially.

I just finish setting up the last camera when my sissy walks in. And what a sight! Today he is dressed up like a cute school girl. Uniform and all! From the top down, he is wearing a blond wig with pigtails, and a white blouse tied in a knot between his breasts. This is the only thing holding them in –he has no bra on. Around his waist is a super short plaid skirt. Underneath the skirt, my sissy son is wearing a pair of white, frilly panties. His skirt barely covers them –you can see a hint of them every time he walks. His legs are covered in white stockings. And he expertly walks around the room in a pair of black high-heeled shoes.

Me: You look adorable! Love how your skirt looks! Do a twirl for mommy.

My sissy son twirls in his outfit. I got it from a stripper store online. It is all held together with Velcro straps. I can’t tell if he is embarrassed because today he has on a skin-tight latex mask. Specifically, a Barbie doll-like face mask, as requested, complete with large, blue eyes with smoky eyeshadow and big, red lips. It makes him look more like an inanimate object –just what this client likes. I can see his eyes through small slits in the face mask.

Me: Are you excited dear?

Him: I don’t know mommy. What exactly are we doing today?

Me: You’re gonna love it. I promise. And I don’t know about you, but I’m excited.

Him: But last time, it really hurt. I felt like I was going to-

Me: Last time, we got a bit carried away. But that video is now our most popular one! You are becoming a star! And I think this one will top it! Now stop delaying and come here.

Him: Yes mommy.

Me: That’s a good boy. Now, I first have to tie you up, so come stand right here and spread them nice and wide.

He walks to the middle of the room where I am standing and spreads his legs. I kneel down and shackle each ankle to chains connected to eye-bolts in the concrete floor. With them secured, I stand back up, and with the help of a foot stool, begin fastening his wrists xslot to similar bolts secured to the ceiling. When I am done, I get off the foot stool and put it away. My sissy son is now stretched out, standing like an “X” right in the middle of the room.

I make my way over to the cameras and switch everything on. I move out of camera frame and briefly compose myself. Showtime!

I walk back into the center of the room, sexily swaying my hips, and approach my tied-up gimp.

Me: Now what do we have here? Looks like a naughty little school girl. Have you been naughty little girl? (I stand in front of him with my hands on my hips.)

Him: No mommy! I have been a good girl! I…I…haven’t been bad.

Me: Then what is with this skirt? Looks a little short to me. Something a slut would wear. Are you a little slut? (I gently lift up the hem.)

Him: No. I’m not a slut. I am a-

Me: Yes you are. You are mommy’s little slut! And today you must be punished.

Him: No mommy…please don’t-

Me: Enough! (I spank his panty-covered ass.)

Me: I have had enough of your disobedience, little school girl. Today you are going to learn a lesson.

With that, I rip off his skirt with one pull. His blouse comes off next. His hormone-enhanced breasts spill out and hang freely. His little panties also come off with one tug –I love these stripper clothes! My sissy son now remains standing, totally naked apart from his white stockings. He almost looks like a naked Barbie-doll –if you ignore his tiny metal chastity cage between his legs. All restrained with nowhere to go.

Me: Now that’s better! A true slut.

A kneel down in front of him and take his tiny chastity cage in my hands.

Me: Do you want to show everyone what a big boy you are? Want mommy to unlock you?

Him: Yes mommy! Please!

I take the keychain off my neck and quickly unlock him. The chastity cage comes apart in my hands, and I throw it aside.

Me: Wow! You are a big boy! Almost two whole inches! You must be proud!

I stand back up and face the cameras with my ass pressed against his tiny cock. Arching my back, I ever so slightly begin to grind against him. He hasn’t had stimulation like this in forever.

Me: Do you like rubbing against mommy? Do you like the feel of mommy’s bikini?

Him: Yes mommy! Please don’t stop!

Me: This is as close as you’ll ever get to pleasing a woman. You know that right?

Him: Yes! Please…please don’t stop!

I can feel him trying to hump against me –his tiny cock desperate to get any relief. I pick up the pace and start to grind faster against him. I glance back and look at his eyes through his ridiculous mask –he is totally focused on my ass.

Me: Make sure you tell mommy when you are about to cum.

Him: Yes. This feels so good…oh mommy…

Me: On second thought…I have a better idea.

I abruptly stop grinding on him and walk over to a side table. I come back into the center of the room and stuff a pair of my panties into his mouth. That should shut him up. I stand next to him and look into the cameras.

Me: You see this? (I hold his tiny erect cock between my thumb and index fingers.)

Me: It used to be much bigger. But I couldn’t allow that, so I placed him in chastity shortly after his eighteenth birthday. He has now been in chastity for a couple of years now. His cages have gotten smaller and smaller over time. The cage you saw today is his smallest. I plan to go much smaller too! Unfortunately for him…his little cock is continuing to shrink…thanks to his tiny cage and hormone therapy.

I look up at my sissy son and see him pleading with his eyes for me to stop. I am revealing to the world his big -or rather, little secret. I then show off and explain his ownership tattoos to the camera. I imagine his face must be bright red under his mask.

Me: And for the grand finale…I want to try out a new tool. I’ve mentioned before about how much I hate milking my sissy by rubbing my vibrator up and down his cage until he spurts. I’ve always xslot Giriş felt that he gets too much pleasure from that whole process –even with his chastity cage still on. No more! I have just received in the mail a new tool which will change all that!

I walk over to the side table and reach into an open drawer and pull out an object. I approach the camera to show it off, holding it in one hand. It is a curved butt plug. It is made of clear acrylic plastic with several stainless steel rings around its bulbous head. This head is set at a curved angle from the narrow neck of the plug. And at its narrowest section is another stainless steel ring. Wires and circuits can be seen within the butt plug, embedded within the clear plastic. At the butt plug’s base is a control unit with an ON/OFF switch.

Me: A loyal customer has kindly sent me this new tool to try out. Today, I will demonstrate how it works on my sissy son. This is a new type of plug, specifically designed to milk a male’s prostate –with electrical stimulation! Apparently this is based on the same tech that is used on farmyard animals!

I glance over at my tied-up gimp. Through the slits on his facemask, I can see that his eyes are wide. He is staring nervously at this new tool. This is all new to him too. I wink at the camera before walking behind him and kneeling beside his exposed ass.

Me: Now there should be no need to lubricate this toy. My sissy’s boy pussy is well trained.

With one hand spreading his cheeks, I position the bulbous end against him and begin applying pressure. His little hole immediately starts widening around the tool’s large head. Before long, the 2-inch wide head is totally consumed by his hungry ass –the long, curved neck then slides in quickly. His asshole finally clenches around the narrowest part of the plug, directly on a stainless steel ring. The base of the plug, with its control unit, are all that remains visible.

Me: He took that like a champ! But it should come as no surprise really…I have been training him with butt plugs over 5 inches in diameter, but I will save that for another video. The beauty of this new tool is that it is all wireless. I can control it remotely from my phone.

Before standing back up, I quickly flick the switch on the plug’s base to the ON position. I then snatch my phone off the side table and stand back in front of my son. With one hand on my hip, I browse through the phone with my other, trying to find the correct app.

Me: Ah here it is! This prostate milking tool comes with its own app, so it, in theory, can be controlled from anywhere. Let’s begin!

With my free hand, I pull my panties out of his mouth and throw them aside. At this point, I can’t tell whether my sissy looks scared or relieved.

Me: Are you ready?

Him: Do we have to do this mommy? I cum so rarely anyways…less than once a month. Can’t we keep doing it the same way? (He swings gently against his bondage as he speaks.)

Me: But those milkings give you pleasure. I know they do. I can see your face every time you spurt your cum through your chastity cage. I can’t have that anymore.

Before he has a chance to respond, I tap the green button on the app that says “START”. A little timer starts counting away on my phone. But other than that, surprisingly, nothing immediately happens.

Me: Feel anything?

Him: No mommy. Nothing.

Me: Hmmm. I guess we will have to wait and see…

After about 30 seconds pass, I notice him begin to strain against his arm and leg restraints.

Me: What about now? Feel anything?

Him: I feel…I feel pressure or something…it is getting stronger…

Me: Where? Be specific dear…tell the audience…

Him: In my ass –sorry, in my boy pussy. I can feel the plug throbbing. It feels like it is moving in and out.

Me: Does it hurt?

Him: No…but…but it feels weird. I can’t explain it.

Another minute or so passes. I notice my sissy son begin to almost hump the air. Rhythmically. Nearly every four seconds. The plug is slowly stimulating xslot Güncel Giriş his prostate with brief electrical pulses. He is being involuntarily stimulated –just like a farm animal.

Him: Mommy, the pressure…it’s…it’s growing!

Me: It’s ok honey. This is all normal. Your prostate is being milked. It should be over soon. Is it painful?

Him: No. But I’ve never felt anything like…wait…wait…something’s happening!

I notice him begin to press hard against his restraints. He starts to hump the air quicker and quicker…all the while his little cock remains flaccid –it just dangles as he thrusts.

Me: What dear? What’s happening?

Him: I…I…I feel like I need to pee! Oh mommy! I can feel…something’s coming out!

He thrusts forward one more time and pulls hard against his arm and leg shackles. I glance down at his flaccid penis just as thick white fluid begins to slowly stream out. He is being milked! Months’ worth of cum slowly pours out him in a slow, steady stream. This is no normal orgasm. I can hardly contain my excitement! This is so hot!

Me: That’s it. Let it all out.

His cum continues to stream out of him. An impossibly long stream of cum hangs from the end of his cock before falling to the floor. But right away, a new stream begins to ooze out. I glance down at my phone. The app is indicating that this is not over yet.

Me: How does that feel sissy? (I can’t help but have the biggest smirk on my face.)

Him: It’s hard to explain mommy…it doesn’t feel painful but not good either…just that the pressure is gone…or almost gone…

Me: You haven’t cum in months. Do you still feel horny?

Him: Yes! Mommy, I still need relief. Please. If you would just-

Me: Quiet. Your mommy is very satisfied. This is all working perfectly.

Another long stream of cum falls to the floor. I bend down and scoop as much of it as I can into my hand. I stand back up and present it to my sissy son’s face.

Me: Look at all of this. You should be proud. Months and months of cum. All forcibly milked out of you. This is just a taste of things to come. Now show mommy what a good sissy you are.

Him: Yes mommy. (He knows what to do.)

I press my open palm against his outstretched tongue. My sissy son hungrily laps up his cum from my hand. He hasn’t tasted his own cum in so long –this must be a treat for him.

Me: Well I hope you enjoyed that because that is how all milkings will take place from now on. No more vibrator on your chastity cage. No more pleasure. No more ejaculations. Just clean, clinical prostate milkings with this new toy.

Him: But that’s hardly any relief at all! I’m going to be so horny mommy! Please no!

Me: It’s for the best Honey. You will grow to love it! I promise! Once a month I will tie you up like this and insert this little device into your boy pussy and have it zap your little prostate. Or maybe I’ll tie you to my bed…or maybe have you sit on the toilet…Yes! Maybe you can just sit on the toilet with this device in place. That way you can be milked for quick and easy disposal. No mess…no fuss…no ceremony. We can make a routine out of it. We’ll see… oh look! According to the app on my phone, you still have more left in you. Ready for Round 2?

Him: I don’t think that is such a good idea mommy. I can barely-

Me: Oops…I already pressed the start button. Hope you don’t mind…

Before he can speak again, I grab a ball-gag hanging from the wall and strap it in place around his face. I notice he is already reacting to the resumed electrical stimulations. His eyes start to roll back into his head from the sensations.

Me: Now dear, mommy has is late for yoga class. I hope you don’t mind hanging around here until I get back. Enjoy these few remaining hours out of your chastity cage. Because when I come back, it goes back on. And this time, it’s not coming off –not until my birthday. Ciao!

I give him a kiss on his cheek before going around and turning off the cameras. I leave the room with them in tow. As I close the door, I glance back at my gimp son pathetically hanging there. I’ll come back for him in a few hours –maybe after I finish editing this new video. This clip is going to be hot! And I can’t wait to see what new custom video requests I have waiting in my mailbox!


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