Inflatable Butt Plug Pegging: Hardcore Anal Stretching

A wicked session of inflatable butt plug pegging.

Inflatable butt plug pegging turns my sissy into such a little cock hungry bitch! Oh, he absolutely loves it. It’s such a wild mix of pleasure and pain that it’s both a punishment and a reward for him. See, I know he loves it when I use one of my vibrating toys on him. How could he not? When I use my strap-on to rub the big, vibrating cock head against his prostate, it’s like he has a clit. The pleasure drives him insane, it makes him squirm and whine like a little whore. But when I use the bigger toys that stretch him out, it’s a wave of pleasure that leaves him breathless. It truly transforms him into my little submissive bitch.

The other day, I decided to take it a step further. I’ve always been curious about playing with inflatable dildos myself. The feeling of being stretched out is so delightfully filling, that it sounds fun to use a toy that you can expand! So I decided to test it out with my sissy bitch first. I went shopping and found him a high-quality toy that looked like it could last to give him a good pounding. After all, I didn’t just want a toy that would fit in his ass and stay there, no! I wanted one I could totally rail him with for an inflatable butt plug pegging session.

And that inflatable butt plug pegging was intense.

I brought the toy home and cleaned it all for the first use. Then, I even sent him a little ‘teaser’ picture of it in the original packaging. I captioned it: be ready when you get home. He immediately started spamming my phone, half in excitement, half in fear of how I was going to stretch his little ass out. I didn’t offer him any comfort whatsoever. After all, I knew I was going to leave him sore and whimpering, begging for a beak. I even giggled and sent a follow-up picture with a set of handcuffs beside it. Oh, he knew he was in for a rough inflatable butt plug pegging! And just like that, my little sissy came running over.

As he walked in through the door, he fell right into his usual routine. I ordered him to strip naked for me and wait in the bedroom. He marched his little ass upstairs, where I found him kneeling over the edge of the bed. He held his ass in the air and even held his cheeks spread apart for me. “Good boy.” I rewarded him with a light slap on the cheek. And for his obedience, I even used a little extra lube. He squirmed in excitement as I applied the lube to his tight little ass. I even gave him a little extra pleasure by sliding a finger in to tease his prostate. But that was all that he was getting before his inflatable butt plug session. In seconds, I took his hands off of his cheeks and handcuffed them to the sides of the bed.

Now, he was completely at my mercy.

And with a little extra lube, the head of that toy finally slid in. At first, it was just like any other plug. He hardly batted an eye. But then, I wrapped my hand around the little pump and I gave it a few tests. “Aw, doesn’t feel that big, does it?” I taunted him, and he took the bait. “No Mistress, not very big.” Ha! He fell right into my little trap! With a few more pumps, he suddenly regretted that statement. The toy had expanded from about an inch wide, to a thick two inches. It was now thicker than most of the strap-ons that I used to rail him with. The inflatable butt plug pegging was now sounding like a punishment session to him.

“Hmm, how big can it go… how big can you take?” I continued to taunt him. My voice was sweet and mischievous, and he hated knowing I was totally in control! His hands were handcuffed so securely that there was no way out. He lay there, completely at his Mistress’s mercy. Pump, pump, pump… The inflatable butt plug pegging grew more intense by the second. Now, the toy had expanded to a thick two and a half inches, and soon three. Thankfully, it was a thick rubber material so I was safe to start tugging at it. Little by little, I tried pulling the toy out, which stretched his little sphincter out as the enlarged head pushed its way out. Ohhh, I left him so sore.

With every single push and pull of that toy, I stretched his ass out like he got railed for hours! Maybe  I should use that toy on you next. Could you handle it?

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