Riding Crop Spanking Session: Sydney’s Punishment

Sydney confessed to me that the thought of being spanked aroused him and asked me for a riding crop spanking session.

Sydney and I were sitting on his living room sofa when he leaned over with a blush on his face. Meekly, he told me how much he loved the thought of being spanked. He knew I was a domme. He pointed out that I’d done riding crop spanking sessions and asked if I could spank him, too.

Sydney explained that he learned I had done a dominating maid roleplay, and he wanted to try something with me, too. Spanking was what came to mind.

I smiled and told Sydney that I’d love to spank him. Honestly, I loved the thought of turning his ass bright red and watching his eyes well up with tears. It’s the sadist within me. The idea of his pain making him excited and squirm sent shivers of arousal down my spine. How could a girl say no to that?

After asking a few questions, he told me he wanted the spanking now, while he was still feeling brave. Additionally, he wanted a crop rather than my hands, explaining that my hands would feel too personal. He had a riding crop in the house, and he got up to grab it.

When he brought it back, I inspected it closely. It was a cheap crop, and I pointed that out to him. The crop was stitched poorly, and the leather was already cracking. It wasn’t very good at all. However, Sydney assured me that he wanted the cheap crop and didn’t deserve anything else.

So with that in mind, I went ahead and helped Sydney into position. I put him over the arm of the sofa, his face down on the soft sofa pillows. Before I started swinging that riding crop, I checked in with Sydney. No tingles or weird angles, so we were go.

After all, I wanted to hurt Sydney during our riding crop spanking session, but not harm him.

I leaned behind Sydney and placed my hand on the small of his back. He whimpered, spreading his legs a little more for me, making sure I had easy access to his butt. I squeezed it for a moment and then slipped my hands into the hem of his pants. As per his request, I slid his boxers down along with his pants, letting the clothing pile around his ankles.

Since he was a new body for me to spank, I ran my hands up and down the back of his thighs. Nothing unusually hot nor cold. I took a few practice swings, making sure I knew where his ass was versus his thighs. Today, I only wanted safe play during our riding crop spanking session.

I tapped his right cheek with the crop first, and then thwacked it down with all my strength. He gasped and let out a groan, his hands twisting in the sofa pillows. Smiling, I thwacked his left cheek next. Again, Sydney gave me the same response: a beautiful gasp that caused his voice to crack.

But really, watching his hands and face twist as I repeatedly brought the crop down on each cheek was addicting. I went over by four strokes, two for each cheek, as Sydney burst into tears. When I finished, his ass was bright red. His legs trembled,  barely able to hold his weight up.

What will you look like when I’m done spanking you?

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