A hot, creative session of sissy ass training.

Sissy ass training is always so much fun when it comes to breaking in a new pet. Nothing quite compares to it. I love amping up the sissy ass play until my new pets can take big, thick toys. Though, it doesn’t always come easily! Sometimes they have quite the tight little ass, and it takes some extra work to really break them in. But honestly, it’s so much fuckin fun to see the look on their faces through all of it. My favorite little pet to break in is called Daisy. Dirty little Daisy loves to have her ass swallow up all of my toys, but she wasn’t always so receptive! Her ass was really fucking tight in the beginning!

And now, well it loves to swallow up whatever I fucking give it. All that sissy ass training has her acting like a perfect, proper little lady. Now, she kneels and begs for the kind of rough, deep fuck that she would shy away from at first! And how did we do that? Lots and lots of training with toys. At first, she couldn’t even handle her own fingers. She would squirm at the thought of something going into her ass, especially the mess that it would make. But soon enough, her ass craved it, needed it, and practically begged for something bigger than fingers. One finger, two. We worked our way up until she could finally fit three fingers in.

I stretched her ass out slowly.

Soon it all came together beautifully. We worked our way up from her fingers and started using butt plugs for her sissy ass training. I ramped up the sizing slowly until one day, when I found the perfect toy. I was out doing a little bit of grocery shopping when I saw it: a perfectly sized cucumber. I picked it up, along with some ginger, and decided we were going to have quite a day. All of you masochists know where I’m going with this. When I made my little pet finally take the cucumber in his ass, it all fell together. She whined, and complained, and begged for me to take it out.

So we made a deal! If I took it out, she’d have to keep a butt plug I carved out of the ginger. And of course, my sissy agreed, thinking that it would be better. That is until I actually slid it in. Sissy ass training had never been so rough for her. As I slipped the ginger in, she realized why it was such a punishment. The burning, the warmth, the ache of her ass stretching around the girth of the plug! She whined, moaned, and squirmed incessantly as she tried to get used to it. And just when my sissy had gotten used to it, I would pull it in and out a bit, just to mix in all those fresh ginger juices. And the warmth and burning punishment would start again.

She grew into such a little whore for sissy ass training.

She couldn’t even babble or beg for it anymore—it was all moans and whimpers. Even then, the sissy ass training continued with a vengeance! I slipped the big, thick ginger plug out and replaced it with the buzzing head of my vibrating strap-on. Inch by inch, I sank the entire length into my pet’s ass. With the creaminess of the lube and the warmth of the ginger juices, she was ready for a rough fuck. So I went at it, slamming her harder and harder. Her submissive ass craved it and gaped for it. My hands spanked that ass sadistically, harsh, and quick. Handprints littered her ass, and my nails scratched her cheeks up too.

She was so thoroughly lost in the feeling. That sissy ass training was just the beginning of it all. I mirrored all her fetish phone sex fantasies and fucked her ass the way she always begged for it. Little by little, she grew used to the size of my toys and strap-ons. And then, I got to finally invite in something bigger…

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