He craved a rough sissy fucking punishment.
A rough sissy fucking was just what my little sub needed. Now, my little sub’s name is Daisy. Obviously, sometimes he goes by Daniel, but you know what? He likes Daisy more. It makes him feel pretty and feminine. It certainly helps when I make him wear a nice lace-front wig, and he gets to feel luscious long locks of flowing blonde hair. Of course, he also dresses up to fully complete the look. Now, my little sissy likes to act up sometimes. I think he’s a bit of a masochist. So Daisy is no stranger to slave cock torture and the wonderful world of toys that come with it. He has a weakness for all things kink-related, from risque lingerie to enticing toys. Sometimes it’s so wild that he’s a little scared of his own curiosity.
Little femboy Daisy loves fetish phone sex but freezes up in wonder whenever she sees one of my bigger toys. I’ve shown him my entire selection, though little by little. When I first started playing with him and his little ass, it was all about the spanking. I spanked him for hours and turned his cheeks bright pink and red. Sometimes we would escalate it on and on, and he’d have little welts on his ass the next day. Of course, he loved the little sting and reminder of the rough spanking he received. If he could feel it the next day, it was one of his favorites. He still acts up a little too much to this day, trying to get a rough sissy fucking and punishment out of me!
And of course, if he begs, I deliver.
I can tell when he mouths off on purpose. He leaves the room murmuring something silly about how I’m going to go easy on him, and he kind of chuckles at that. Of course, I know it’s just bait and a challenge, but I love rising to the occasion and using it as an excuse to be extra cruel. The last time he did that, he finally got to take on one of my biggest toys. I used little vibrators and 5″ dildos on him in the past to break his ass in. He loves a good prostate milking and a little fucking from time to time. However, he always looked at that big strap-on with wonder and fear. It was time to give him exactly what he wanted: a rough sissy fucking to turn his ass sore.
He walked back into the room after his little murmured challenge, thinking I had separated some whips and materials to spank him with. However, he walked right back in to see me standing at the edge of the bed, with a huge 12″ black strap-on attached. You should have seen the look on his face. It was a mix of excitement and horror, and yet, his little dick popped right up. What a little horndog, am I right? I had a bottle of lube in one hand, and he knew I was ready to break him in just like he’d challenged me to. “Come here,” I commanded him to join me and to bend over the bed.
He obeyed instantly.
I think he was a little scared of how much rougher I could be when wielding a big 12″ cock like that. It did make me feel strong. I could tell he was intimidated by it; he shied away from me a little when I let him feel the big mushroom head against his ass. But with enough lube, it slipped right in. His little sissy ass begged for it; it stretched around every inch of that strap-on like it was hungry for it. He moaned and moaned and didn’t really know how to take it when I fucked him with something so big and thick, but he loved it. At one point, he even got the nerve to start sassing me! The little prick – can you imagine what I did?
I got him to squish his little sissy cock into a metal chastity cage while I fucked him. He was left to his own devices, squirming and squished in a tiny little metal cage as I pounded his ass for hours. And you can bet that I started spanking him too. A rough sissy fucking is not complete without a hard spanking to finish off his cheeks.
