A Visit to Ms. Cassidy's

Chapter 6: The Sound of One Hand Clapping

Never in my teenage life did I ever think I would hear those words. It was finally happening, after many hormonally fueled years I was finally achieving something I once deemed impossible.

Ms. Cassidy was sitting in her black leather chair, it had a large cushion for padding and no arms on either side of it. She was facing me with her legs pressed firmly together, waiting for me to assume the position. She had a relaxed look to her and certainly didn't portray the menacing bravado I saw on her website page.

I walked towards her and made the mistake I had seen too often in videos of the person bending over the wrong way on a lap. Akin to pushing on a pull door, I instantly got pretty embarrassed but she helped me quickly correct myself so she could use her dominant hand to spank me with better. So much was rushing through my mind as I began to position myself across her lap, I could barely keep my thoughts straight.

What I was going to wear for my spanking was on the forefront of my mind when I was planning this visit, especially below the belt. This wasn't me trying to look good for her, more so it was trying to see what would feel good to be spanked in while also offering some protection. I had a black pair of silky sweatpants I was curious to try but decided against due to how they fit me rather poorly at the time. I ended up going with normal boxer briefs, and a pair of jeans. It wasn't anything fancy for sure, and I wanted to look as normal as I could. I was afraid if I showed up in any thing that looked odd, or conveyed that I had other intentions, Ms. Cassidy might call the whole thing off.

Something I had always been self conscious of is my build. I was healthy by doctors standards but I was on the extremely skinny side. Weighing only ~110 pounds at the time and definitely showing it. I was the definition of a stick figure, a walking twig, someone who literally got pushed around when the wind picked up. Skinny proportions unfortunately extended to my butt as well. As I got older I learned that many women like a guy's ass, especially if it's got some heft to it. However, I always felt mine was far too bony to really be nice to look at much less spank. This self doubt was nestled firmly in my mind leading up to and during the session.

As I laid across her lap it was a very strange feeling for me. It was an odd sense of comfort. I felt safe and that while things were out of my control from here on out, everything would be alright.

Ms. Cassidy then brought my attention to the mirror in the corner of the room. "If you look in that mirror straight ahead you can see your butt over my knee while I spank it. Lots of clients like to see their butt being spanked while it's happening".

I thanked her for that and decided to keep it in mind during the session. "Alright, are you ready?" I said yes and she brought her hand down on my butt for the first time.

Her opening spanks were very light, almost like the kind a babysitter would give as a warning to the children she was babysitting. They were over a jeaned bottom so I barely felt a thing. That being said, there was something very nice about them, almost like a massage for my rear.

"How's this so far?" She enjoyed keeping the conversation flowing during my spanking which is something I appreciated as well.

I told her that it felt quite good. "Don't worry things will pick up soon. By the way I always spank my clients for something they have done wrong. So what have you done to deserve a spanking?"

I pondered this for a moment. By all accounts I was very well behaved. This was the most rebellious thing I had ever really done besides talking back to my English teacher in 12th grade. I told her that I wasn't really sure and she stopped spanking me for a minute.

"Well there has to be something you have done to deserve a spanking, hasn't there? Have you been out late partying?"

No.