Pegging Ass Training: Stretching Him with Toys

A day of pegging ass training.

Pegging ass training is always such chaotic fun for me. See, sometimes I can’t quite make up my mind. I’m frequently torn between being a gentle and sensual Mistress and a vs. a sadistic Domme. And, of course, my little sub loves both of those sides of me. So really, I get to flip it around however I see fit. It can be even more fun when he guesses wrong, too. My sub spends all his work day daydreaming of how I might tease and spoil him later. He’ll come home expecting his sensual Mistress to give him a treat. And to his dismay (and naughty surprise), he gets a showdown with the mean bitch in charge and her thick strap-on!

It’s exciting when he doesn’t know what to expect. And honestly, it’s exhilarating for me to flip the switch and give him something unexpected every time. No matter what side of me he gets, I’m sure to give him a hell of a pegging ass training session. When I’m feeling gentle, I may go easy on him and let him adjust to the size of the toys I fuck him with. But when he’s been a bad boy and keeps testing my patience, all bets are off. After all, lube is a miracle worker. And nothing is quite as satisfying as that SQUEAL he lets out when I shove a huge dildo into him by surprise!

I love training his ass.

So I have practiced several different ways of doing that. See, sometimes, I even let him get a little ‘gym training’ in while simultaneously training his ass for me. Squats! Specifically, I order him to set up a mounted or suction cup dildo. He’ll do as I say and set it up somewhere like the floor or on a small footstool. And finally, with his ass lubed up and ready to go, he’ll squat down and settle himself on that. I love the pegging ass training sessions with my sub, so I make him sit there for a while so his ass gets stretched out! And finally, he can start bouncing and squatting on it, getting a hell of a leg workout while fucking himself.

That sounds hot as hell, right? Maybe I should make you do the same for me. We’ll pick out a big toy and a nice surface for you to settle down on, and you can fuck yourself for me. A pegging ass training session isn’t complete without leaving you sore, of course. Some days the ‘training’ part can be really easy. For example, the last time, I had him ready himself with butt plugs! I even bought him a pretty crystal-ended butt plug. It had a little pink heart crystal on the outside of the flared base. Honestly, it was pretty cute when he bent over to show it off for me.

The pegging ass training sessions have to get rougher, though.

So I’m not all sparkles and sunshine. I’m not always the gentle Mistress that lets him work up to speed all by himself. No, I like to get fully in control sometimes. So, while he started off with that little butt plug, I was in charge of what came next. I ordered him to lay over the edge of the bed with his ass up in the air for me. He was perfectly positioned for me! And I could hear him squirm and whimper when he saw me walk into the room. I spared him no surprise. I walked in with my strap-on already fastened in the harness – a big twelve-inch cock! He saw it and KNEW that this pegging ass training session would hurt!

And that’s exactly what I did, too. I dripped a good amount of lube onto the big mushroom head of my strap-on cock, and along the shaft of it too. He waited patiently, though uneasily. Finally, I let him feel the big head as I rubbed it between his cheeks. A wave of anxious anticipation washed over him. With all that lube, he knew he would get a smooth, easy fuck… But with how big he could tell the strap-on was, he was in for a rough night. I always love those pegging ass training sessions, especially when I get to see him slowly lose confidence. The bigger the toy, the more mischievous I get! Tell me, how long could you have lasted with that strap-on?

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