A sissy ass training he won’t soon forget.

Sissy ass training was all that he needed and everything he craved. My little submissive pet always loves to mouth off and show his attitude. Being a little brat is what gets him exactly what he wants: discipline. He’s no stranger to sissy ass play, but the punishments are his favorite part. And honestly? They’re my favorite part too! Pampering him is easy, but we both know that my little subbie, Rachel, loves to get filled up with big, thick toys and strap-on cocks. So, I’m more than willing to step up and give her the rough fuck that her sissy ass craves. But sometimes, I have to up the ante.

And of course, she fucking craves that too. Sometimes, little slutty Rachel likes giving me attitude. She’ll be dressed up in her normal man-clothes, looking rather pathetic in polo shirts, if I do say so myself. The khaki pants don’t suit her well either. So she’ll be walking around in her daily clothes, acting like a brat. And finally, it will get under my skin enough to do something about it. That’s when Mistress Kali comes out to play, and Rachel gets the sissy ass training she practically begs for. With such a smart, sassy mouth, I have to put it to work before anything else. Her mouth is the first thing to get to suck on my toys.

And she’s a good cocksucker, too.

I made her put in the work to get good at it. She was pathetic at first! She would even gag on a toothbrush.  But after enough fetish phone sex and training sessions, she learned how to suck cock like the best of them. And once she could finally fit it all the way down her throat, it was time to train her some more. We had to upgrade to sissy ass training next. Her mouth and throat were ready to please, tease, and do as she was told. And now, it was time to stretch and fuck her ass until it didn’t have brakes anymore. And the first training session was brutal. I had such a nice, thick strap-on to really break her in with. But of course, we started with smaller toys, like butt plugs.

I bought the perfect one for her ass, too. The first training butt plug I got her was dark gunmetal, smooth and reasonably sized, with a red crystal heart at the flared base. It was gorgeous! And you should have seen Rachel’s eyes light up when she saw it. She was ready to start her sissy ass training with it. But of course, we moved up in sizes rather quickly. With the right amount of lube and warming her up, she flew up through the sizes easily. By the end, she was ready to take on a full-sized dildo, and that’s exactly what I gave her. Her ass looked at my toys so greedily!

So I fucked her hard with it for her sissy ass training.

A nice squirt of lube here and there, and she could fit it all. Her ass swallowed every inch of that strap-on cock. She was greedy for it; you should have heard the moans, the whispers, the sighs, and groans. Her body quivered and squirmed and ached for them. I took the sissy ass training further with every thrust of my strap-on dildos. First, I broke her in with a modest six incher. But up next came the thick eight-inch cock. The width and girth of it certainly broke her in. She was lost in the feeling of it. Her whimpers filled the room as I shoved my cock deeper into her sissy ass, and that was just the beginning!

The thickest cock of all was kept for the very end. Sissy ass training was not complete without it. I saved my big, twelve-inch, thick, vibrating strap-on for the show’s finale. When she saw it, I swear she went a little pale. But what could she really do about it? I’d warmed her up with plenty of toys, and now was time for the final challenge. Her training would be complete with this one thick toy… if she could handle it. And trust me, it was a lot, but she loved every painstakingly thick inch of it. Could you have taken such a big toy?

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