Sissy Strap-on Punishment: Pegging Him Harder

The joys & pains of his sissy strap-on punishment.

A sissy strap-on punishment can never be too easy. I love letting my wicked, creative streak out when it comes to punishing my little submissive toy. See, sometimes I wonder how he’d react if I gave him a very LIGHT punishment. I think he’d be even more paranoid, looking around every corner and wondering when the actual punishment is coming. Maybe I’ll try that next with him and barely give him a spanking. I’m sure the paranoia will riddle him. He’ll be looking over his shoulder and expecting a room full of toys I could use to fuck him with!

But usually, he gets exactly what he’s aching for. I’m always willing to supply the matching pain for his actions. In fact, he expects it and yearns for it. My little subbie is a bit of a masochist, a total pain slut that wants a hard, rough fuck every time he “breaks a rule.” And trust me, he’s had me set up plenty of easy rules for him to break. For example, when he comes over, he’s supposed to dress up like a sissy within five minutes of entering my house. Otherwise, he gets a sissy strap-on punishment.

And he breaks it on purpose!

My little sissy toy always wants whatever I can give him. So when he comes over, sometimes he talks and talks, knowing I’m keeping time on my phone. Sometimes he talks so much as he goes to my room to change that he purposely exceeds his time limit. And then, of course, he’s guaranteed to get what he wants. He craves a sissy strap-on pegging punishment, and I give it to him. Once he’s earned his punishment, it’s all up to me. I could be kind, or I could be cruel. I could make him stick a little butt plug covered in ginger paste in his ass. Or even better, I could fuck him for a certain amount of strokes and have him count out each one.

All our games are so wicked and fun. The last time I got to fuck his ass was an improvisation of that second punishment. I had him pick a random number from one to five hundred. The poor soul picked three-fifty-two! Now, he clearly didn’t know what he was choosing, or maybe he was hoping for a spanking instead. Because his eyes went wide the second I told him to bend over and spread his cheeks. And this time, I gagged him too. I slipped a little ball-gag over his mouth, so he was a mumbling and moaning mess during his sissy strap-on punishment.

His sissy strap-on punishment had him shaking.

He couldn’t really move, and he couldn’t yell or whine. I secured his hands to the headrest and had him put his tight little ass in the air. Then, he was entirely under my control. All his days of strap-on anal training didn’t prepare him for such a high number of strokes. He tried to count them out one by one, but I quieted him with the gag. He couldn’t look back at me either; all he could do was twitch and squirm. With every stroke, I made him take the toy from the base of the balls to the head. I could feel his struggle every time I got it in, almost down to the balls. Poor little subbie was getting SORE from this sissy strap-on punishment.

The pegging was too much for him, but it was delicious! He came twice for me through the whole ordeal. I wonder how you would feel, bent over the bed, tied up, and at my mercy. Could you handle my strap-on fucking?

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