A Visit to Ms. Cassidy's

Prologue

For as long as I can remember, I have always been fascinated with spanking. The furthest back memory I have is watching a scene in a cartoon about humpty dumpty where a man made out of lightning takes him over his knee and spanks him. Ignoring the absurdity of the scene, I remember fixating on it. I don't know for sure if that was my first real exposure to the idea of spanking, but it certainly wouldn't be the last time I thought about it.

My interest in the subject only grew as I got older. Anytime the word was mentioned or it was shown in some form of media I would focus on it. I would look up the word or similar ones in dictionaries to learn more about it. Even the games I played with my neighborhood friends would involve spanking one way or another. We would never actually do it to each other, instead we wove it into our games and stories that we made up in our spare time.

I was never spanked growing up like I had so desperately wanted. The closest I came was during two separate times. The first was when my childhood babysitter threatened me with one, but she never followed through on it. The second time was when my Dad gave me one smack on my butt for being too loud with my younger brother. Needless to say neither of these times really satisfied my curiosity on the subject.

My interest in the subject only grew as I got older. It wasn't until I had access to the internet that my research of the matter would hit a renaissance. I quickly became very fascinated with spanking stories. From what I remember, I shied away from spanking videos at first. To me at the time they felt far too dirty and adult to be watching them. Instead I just stuck with any form of written spanking story I could get my hands on.

It wasn't until 10th grade that I finally learned the warm butterfly feeling I had about spanking was arousal. I had never really known what to do whenever I felt this way as no one really told me anything about it. I felt embarrassed even thinking about it, like it was some secret I had to hide from everyone.

One day I had heard the other boys during High School talk about something called masturbating, but didn't really put two and two together right away. Eventually after hearing about it so much and deducing what it meant, I decided to give it a try.

Spanking always gave me these hot and heavy feelings when I looked at it, but now I realized I could use videos of it to help explore my fantasies. I dreamt so much about being put over someone's knee and spanked that I would go to ridiculous measures just to try and imitate it. One of my earliest memories was bending over the toilet seat in my bathroom and humping it while pretending I was being spanked.

While that probably wasn't the best thing to do as a young pubescent boy, I kept going back to it as it felt the closest to actually receiving one. I would later graduate to bending over pillows when my family wasn't home and pretending to hump someone's thighs while being spanked.

As I explored myself and learned more about masturbation I stumbled across a practice that helped me inch ever closer to my desire. It was called self spanking. While I had always fantasized about someone spanking me I never realized I could just do it to myself.

While not nearly as fun as a real one, it was as close as I was gonna get at the time. I would look up dice games that decided how I should spank myself, try different positions and implements and do plenty of other horny acts while alone. Those sessions would always feel the best for me when I spanked myself to an orgasm, but they never really quite reached my end goal.

My biggest frustration growing up was that I couldn't find anyone to spank me. I always felt the most turned on at the thought of being spanked by a woman but didn't really have any in my life to do so.

Many people were spanked by their parents growing up but mine didn't really believe in it. The concept of me asking my parents to spank me always felt a little too weird. Coupled with the fact I didn't have the guts to ask any of my friends to spank me and I was stuck between a rock and a hard place.

With many of my options exhausted for achieving my dreams of being spanked, I did what any teenager would do, I turned to the internet. I would go to chat rooms and forums trying to look for a way to satisfy my itch. It was there I eventually found the profession that would one day help me achieve my goal, the dominatrix.

They were intimidating, but honestly that only made them hotter to me. They offered exactly the services I was looking for. They could spank me with no questions asked, exactly how I wanted. I thought I had hit a gold mine. But it turned out to be more fool's gold than anything else. I was underage, and they only saw those 18 and up, or sometimes even 21. None of the ones I could find lived even remotely close to me, and I didnt have a car. Most importantly I had no money. Many of them cost hundreds of dollars to visit.

So my hopes were dashed, I would continue my search in vain, bummed that it likely would not happen any time soon. Unbeknownst to me, that would all change right before my 20th birthday.