Mommy s Chastity Boy Part III
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Mommy's Chastity Boy Part VIII free porn video
(All characters are age 19+; not sweet or sentimental)
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. They are not
painful -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: Ok spread your legs and put your hands behind your back. Don't you
dare move.
Him: Ok 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 are
permanent. You will then become mommy's little eunuch.
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: And you might not be. It is all up to you. I don't want to castrate
you. But if you fail at this game, it will be out of my hands.
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 dear. 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 turn purple 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 ok. 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 a 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-femme face mask that I fasten tightly around his head. Little
eyeholes 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 repurposed 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 castrating 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 caf? 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.
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 castration 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 don't have long. 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.
Him: It's too big! I can't take that!
Me: Tick tock, honey. Tick, tock.
I gleefully watch as he attempts to get the huge dong inside him. His
hands and elbows are braced against the ground as he begins to push
himself into it. He arches his back and leans backward, trying to press
himself against it. I glance over just in time to see his little
boypussy open up and begin to take the dildo. The large girth makes it
difficult, but steadily, my sissy son's boypussy begins to swallow it.
This is by far the largest thing he has ever taken up his ass! And I
once fisted him with my whole arm!
Him: Aaaaaah! Aaaaaah!
I watch as almost six inches of it disappear into his ass. His boy pussy
is stretched around its ever widening girth. He has now taken just over
a quarter of its length! I am so proud!
Me: Just a recommendation sweetie...you don't have to take the whole
thing if you don't want to. You can just find a way to cum instead.
Without even responding to me, my gimp begins to slowly move steadily
back and forth on the black dildo. Several inches go in and out. Over
and over he does this, in an attempt to massage his prostate. He is
totally focused. He has had orgasms like this many times before -I call
them "sissygasms" or "analgasms." Those are basically what he endures
once a month anyway. But I doubt he will be successful -the dildo is
simply too large. I move over to his face and sit on the floor directly
in front of him. I notice that he is starting to sweat.
Me: Trying to have a sissygasm? (I stare at his eyes peering through his
latex mask.)
Him: Yes mommy.
Me: Good luck. I do love that sound your boypussy makes as it slides
down that shaft.
Sitting on the ground in front of him, I take some photos with my phone
and text some friends. I want them to see this in case they aren't
watching the webcams. My sissy continues at it for over twenty minutes.
He thrusts his ass backwards, varying the angle each time, desperate to
massage his prostate. As time passes, he begins to sweat more and more.
He begins to panic. I watch with delight as he becomes increasingly
aggressive with his futile humping. He is now taking over a foot of the
dildo in his ass with each thrust!
While he humps away, I occasionally glance at his dangling balls and
check on their ever-changing color. I notice him sneaking glances at his
bound testicles too.
Me: It's been over half an hour son. Have you cum yet?
Him: No mommy. It's...it's too hard. I can't...
Me: What if mommy helps?
I stop sitting and get onto my knees and elbows -just like him. I back
up slightly so my ass is right in front of his face.
Me: Would it help if you worshiped my ass?
Him: It--
Without giving him a chance to respond, I back my ass into him,
smothering his face between my cheeks. I can feel his nose and mouth
through my leggings. I shake my ass slightly to bury his face even
deeper.
Me: You are clearly not making any progress with whatever you call this.
So I think you need a little push. Literally. Remember the other way to
win this game?
Him: Hghhrrbbh!! Hmmmph!! (My ass muffles his voice.)
Me: What's that? Don't remember? The other way to win... or rather
end... this game is to take the whole dildo. To its base. I think it's
time. Don't you?
Him: Agggggh! (I can feel him struggling to shake his head.)
Me: I'm glad you agree! (His rapid head movements against my pussy are
making me sooo wet.)
Ignoring his protests, I begin to back up and press against him, forcing
him back onto the dildo. I feel his moans and grunts as I push back onto
his face. His protests quickly fade as he accepts his fate. As I am
pushing on him, I glance back and watch the black dildo slowly be
devoured by his ass. He is past the halfway mark!
Me: Almost there! Take it for mommy!
I press my ass harder and harder against him, rubbing my pussy against
his nose each time. I can feel an orgasm building...
Me: That's it! Make me cum!
It's all too much for me. I cum just as I push against his face for the
last time. Waves of euphoria rush over me as I press my sex against his
face. Everything is soaking wet. After recovering from my orgasm, I
stand back up and look at him with my arms crossed. He is almost there.
Only a few inches to go. Time to end this.
Me: Thanks sweetie for that. I've been enjoying this almost as much as
you, but I'm afraid it's time.
I glance down at my pathetic sissy as I place the sole of my leather
boot against his face.
Him: Please no... I...can't take another inch...too big...
Me: Give my boot a kiss, bitch.
While he's kissing my boot sole, I begin to push my foot against him
with all my strength. His boypussy widens quickly around the dildo,
making a wet, stretching sound. And with that...the last few inches ram
home! He lets out a high pitch shriek. And right after swallowing the
widest section, his ass clenches around the base of the dildo with a
satisfying sucking sound. With all twenty inches inside him, my sissy
collapses -ripping the suction cup from the wall. The suction cup sticks
out of his ass -the only part of the dildo still visible. I stand there,
giving him a second or two to recover. Following my instructions, he
slowly stands up. He is covered in sweat, and hardly able to move with
the huge dildo inside him.
Me: I am so proud of you honey! You took all of it! And it's still
inside you! (I give his ass a little spank.)
Him: My ass is so full mommy...it's so big...how are we going to get it
out?
Me: I'm sure we'll find a way. But the good news is the game is over!
You won!
Him: Will...will you take the elastrator band off now? (I can almost
taste his desperation.)
Me: I promised... but...
On cue, we both glance down at his balls. I begin to have second
thoughts...
Comments/suggestions:
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Louise
- 13.12.2022
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