Family Chastity Story Ch. 03

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!

While he is moaning away in ecstasy, 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 and moan. He must be enjoying this.

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.)

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 boy-pussy 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. I can tell he is in ecstasy.

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: That's what I promised...

-End of Chapter 3-

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