A Visit to Ms. Cassidy's

Chapter 7: Heating Up

"Alright young man, it's time you come back over my knee for a hairbrushing, come on out of the corner now. Make sure to keep your underwear around your penis though."

I brought myself out of the corner of embarrassment she had just backed me into for the past few minutes and moved to go across her lap. While doing so I asked why we stopped with the hand spanking as I was really enjoying it.

"Oh come on, man up a little. My hand was starting to hurt and I wanted to bring out a more sturdy implement."

I really wasn't in a place to argue with her so I reluctantly agreed and lowered myself across her thighs once more. I shifted myself into place with Ms. Cassidy adjusting herself slightly. My penis was firmly pressed between her thighs and my midsection. I wasn't as horny as I had expected, but I did start to notice that my dick seemed to enjoy the placement against her legs.

"Alright naughty boy, time for the hairbrush." She brought the black plastic brush down on my backside and it made a distinct clapping noise against my cheeks.

While a hand spanking had more of a slapping sound to it that echoed, the hairbrush had a sharper more focused sound to it with a distinctly higher pitch. The feel of it was different too, the hits were harder and stung much more than her hand did.

CLAP CLAP CLAP CLAP

"Your cheeks are getting nice and red. How are you feeling, still good?"

Going into this session I fully expected to be spanked by a stern no nonsense dominatrix. While she did seem to play the part for a little bit, it was nice to experience this side of her. She genuinely seemed to care about how I was doing and it felt more like a friend looking out for me than someone trying to hurt me. I told her that things were still going good and that I was really starting to feel the effect now.

"Good you are being punished after all. It's supposed to hurt."

CLAP CLAP CLAP CLAP

She continued to spank me with the hairbrush for the next few minutes, occasionally asking me questions and checking in. Otherwise she just let the sound of her spanking me fill the room while she kept increasing the pressure.

The hairbrush spanking didn't last as long as the hand spanking, but it felt just as good. I stayed in sub-space for quite a while during that, blissfully enjoying my punishment. Once she was winding down with her hairbrush I could tell the session was coming to an end. I started to wish it could last forever when she said something that got my attention.

"Wanna try a new implement?"

We had only agreed on a hand and hairbrush spanking prior to this but knowing I probably wouldn't be spanked again for a while I decided now was the time to experiment.

She seemed quite excited to hear this. "That's the spirit! Try something new!"

After some consideration Ms. Cassidy went with a large wooden paddle hanging on the wall next to her. This monster piece of plywood looked like the type of paddle people played pickleball with. It was large enough to cover my entire ass and then some. We had just graduated from little league to the MLB. I made my bed though and it was time for me to lie in it.

"Alright get up off my lap and bend over that table there". I got up and moved over to the table, it had a black leather surface and was standing on four metal legs. The leather cushion on the table was surprisingly comfy with plenty of padding to it, probably to help with prolonged play sessions.

As I made my way over to the leather table Ms. Cassidy said something that surprised me.

"Since you aren't on my lap anymore you can slide your underwear all the way down. I don't want the underwear to get in the way either."

Hearing this made my heart start to beat faster, I was going to be fully naked from the waist down in front of a woman who was helping fulfill one of my longest running fantasies. This was starting to stir something in me as I slowly slid my boxer briefs down around my ankles.

I bent over the leather surface until my chest was flush against it and my ass was facing outwards.

"I like to use this position so I can really get a good windup on the swing. Are you ready?" From what it sounded like, this was probably going to hurt, so I braced for impact.

THWACK

The first swat surprised me to say the least. The size of the paddle made it act like a fan and I could feel a strong breeze seconds before the wood connected with my butt. The size of the implement made it connect with both of my ass cheeks at once making me jolt a bit. Her back swing was fierce and she must play tennis because she was playing a game of doubles with my ass cheeks.

By this point my ass was a nice shade of red and any additional smacks were going to hurt. And boy did they hurt.

THWACK THWACK THWACK

She started slow but kept increasing the tempo to a constant volley. Each swing brought with it a cool reprieve of air before sending a sharp fiery pain to my posterior. As the whacks continued I started to develop a strange feeling. My brain decided that the only thing left to complete this encounter was for me to orgasm while being spanked. My dick started to swell while pressed between my body and the leather padding.

A caveman-like instinct took over me and I started to slowly hump the table. Rubbing my half erect penis against it hoping to eventually get off from the stimulation and the pain from being spanked. I did my best to make sure Ms. Cassidy didn't notice but part of me almost wanted her to. In my head she would notice my naughty habit and punish me further, maybe even possibly putting me back over her knee for more hand spanking.

The feeling quickly left my head as I realized that this was nothing like the porn videos I was being punished for watching. I instantly started to feel shame for what came over me and really hoped she hadn't noticed it.

At this point the score was about 25 love and I was the sore loser. The kid gloves came off when she used a large windup with the paddle. I was really starting to wince from the pain. Each hit sent a searing sharp jab through my ass and was starting to bring me to tears.

"Alright, I am gonna give you ten more hard ones and I want you to count them out loud and say 'thank you mistress'. Think you can do that?" I agreed and braced for the worst.

THWACK THWACK THWACK THWACK THWACK

She started the dishing out those ten final strokes and I made sure to count along to each one while thanking her for them.

By the time we got to five I was already close to tears and making audible groans from the pain.

THWACK THWACK THWACK THWACK THWACK

It wasn't until we finally reached 10 that I was able to sigh in relief. My first spanking was over and surprisingly I was quite thankful that it was. Any more punishment and I would have been a sobbing red mess.

"Ok you naughty boy you can get up now. I think you learned your lesson."

I rose from the leather table and looked at my bare ass.

"Oh I just love the color of that, go ahead and give it a feel."

My cheeks were a nice maroon color, the kind you might see on an autumn jacket. When I touched them they didn't hurt like I thought they would, but were very warm and radiated heat. I collected myself and started to put my clothes back on. Pulling my pants up over my butt I could still feel the warm glow underneath all the layers.

"Why don't you come over here and sit while we go over the session together."

I made sure my pants were on tight with my belt then made my way back to the other side of the room towards her office. It felt like we were actors stepping off the stage after an exhausting performance.