Strap-on Punishment: Ruining and Whipping My Sissy Bitch

A harsh strap-on punishment to make him obey.

A strap-on punishment always gets my sissy bitch to follow the rules! Sometimes I think he acts bratty just so I’ll put him in his place. How unlucky for him, I usually take it even further when it’s time to punish him! I really like to get the toys involved when he’s being a little disobedient slave. I turned my entire weekend into a punishment-fest for him. We’ll even stick to his sissy name, Britney, as I describe all the mean things I did. Yeah, he definitely tried to pull the “oops, I did it again” card with me, and got his ass turned red for it.

See, Britney has a strict Friday afternoon routine! Once he gets home from work and gets a nice hot shower, it’s playtime. He gets out of the shower and puts on a sexy little thong or panty of his choosing. Then, he waits for me to come sissy him up for the rest. He decided to purposely act out and wear his boxers instead of cute little panties. So, of course, you know a strap-on punishment had to follow. As I saw him laying on the bed in his boxers, I simply raised my brows. He grinned and continued watching TV. I stood there in silence, letting him simmer. The silence is always a red flag that something is brewing. As I set my purse down, I snapped my fingers and pointed to the bathroom.

He froze in fear but slowly obeyed.

Off to the bathroom, he went. I made him wait there a few minutes like it was a time-out. All the while, he stood there like a scolded kid, hearing as I opened the zipper on my purse and a few of his drawers. “Mistress?” he called out for me, wondering what I was up to. Within minutes, I came back into the bathroom and ordered him to strip naked. He did so, but reluctantly. “Up against the counter,” I ordered him to bend over the counter and look at himself in the mirror. First, we had to warm him up before the strap-on punishment. As he stared at me in the mirror, he saw as I raised a cat-o-nine-tails whip and brought it down firmly on his cheeks.

Oh, the sting! He squirmed and yelped! And the punishment was just beginning. Next, I secured his hands behind his back with a set of pink, fuzzy handcuffs. I used a sharpie to write ‘SPANK ME’ on his cheeks as I got him ready. I continued to use the whip mercilessly on him. Snap! Snap! His helps and whines got louder. And then came the butt-plug play. I had procured my favorite vibrating butt plug from one of his drawers. He was blissfully unaware that I’d coated it in a mix of ginger paste and lube. Have you boys heard of figging? Well, I use crushed-up ginger paste or sometimes blend ground ginger into lube. It has the same effect! As I popped it into his ass, he slowly spread wide open, getting ready for the eventual strap-on punishment.

And finally, the strap-on punishment he yearned for.

He didn’t know when it was coming. I made him keep that butt plug in his ass for a while. Within a few seconds, his eyes widened as he realized I used the spicy lube. “Mistress! It burns!” He whined and squirmed, but the plug was well-secured in his ass. I even tapped it a little so that he knew it was really stuck in there, and it wouldn’t budge until I removed it. Honestly, I loved to watch the look on his face as I pumped it in and out of him. To make matters worse, I even swapped to a bigger butt plug. The sizing up and relentless fucking was to stretch his ass out. I was preparing for the main strap-on punishment.

And when he was ready, it was time to go. I kept him bent over the bathroom counter, of course. It may have been easier to do on the bed, but I wanted him to look at himself. As I entered the room again, this time I had stripped down to my all-black lace lingerie. His legs were shaking from the butt plug’s vibrations already. So he was momentarily relieved when I turned it off and took it out… But his eyes widened again when he saw I had brought the big toy with me now. It was time for his strap-on punishment. I was going to use a thick 10-inch vibrating dildo, which I then attached to my harness. Its big, thick head was a fearsome sight as I brought it down between his cheeks.

I could see him clench his jaw, grimacing as all ten inches slowly but surely stretched him out…Oh, the fun had just begun! I was going to fuck him round after round… How many could you take?

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