A Visit to Ms. Cassidy's

Chapter 3: What Are Friends For?

I had everything in place for my trip to Ms. Cassidy. The correct amount for tribute, the time, and directions on how to get there. While setting up my master plan to get my backside paddled I was continuously reminded of the ever present dangers of the internet. Ms. Cassidy was seemingly a reputable dominatrix. However there were so many unknowns for me that I was still very anxious. There was no way I would be able to do this by myself. I had to bring in some friends to help me with this one.

I had a nice friend group at the time, but I wanted to make sure the people that I brought in to this would be the right fit. After all, I had never shared with anyone that I had a spanking kink.

I decided on two different friends at the time, the first was Carter, one of my lifelong best friends. Carter and I had been through a lot together and had really become close in these past few years. We shared a lot of deep stuff together, I knew I could trust him with practically anything.

The second person was a somewhat new addition to my friend group. Her name was Jessica. I met her after she started dating one of my high school friends. My friend group was mostly a boys club. That being said, Jessica fit in pretty well. She had a very unique way she went about things. She was a psych major and that fit her personality. She was always inquisitive, trying to pick apart how your brain worked inside and out. Her style was very much like an interrogation, with the end goal of getting to know you more, for better or worse.

I always enjoyed my conversations with Jessica for the most part. Her curiosity and different viewpoints were fascinating to me. She challenged my worldview enough to help me see things from a different perspective. One of her favorite things to do with her boyfriend and subsequently us was to have deep philosophical conversations. These could be about anything from what happens after we die, to what flavor of ice cream our personalities most represent. Spending time with her was something I always looked forward to. Her stance on things would sometimes be different from mine and could cause some tension. That being said, I felt like she helped challenge me in a way that let me grow and come out of my shell a bit.

As I hung out with her more and more I began to realize that I was developing a crush on her. Looking back on it, I feel like me wanting to share this with her had something to do with that.

One night in August a good friend of mine was having a bonfire and we were all invited. I decided this would be my best chance at roping them into my master plan. Everyone that night had been drinking or decided to get cross faded. It would be the perfect amount of social lubricant to bring the subject up without being too weird. I didn't really drink much at the time, mainly because I had to drive home. Really it just wasn't my thing. Carter wasn't drinking much either for similar reasons. Everyone else was trashed enough where if bringing this up was a mistake, I could laugh it off like a joke.

My time came when most of the group decided to run off and hotbox for a bit. This left Carter, myself, Jessica, her boyfriend, and one other friend at the fire. Jessica told her boyfriend to go hang out with the boys to help bond. He put up a bit of a fight, but she quickly won him over and sent him on his way. It wasn't too hard to get the other friend to leave either, especially when some of the other attendees started to play ping pong over in the garage. This finally left the three of us alone. I had keyed them in on something I wanted to talk about that was serious ahead of time so they knew something was up.

It took me a while to finally get everything laid out for them. I wanted to bring them with me because I didn't know entirely what I was walking into and having someone nearby in case things went south would be helpful. Especially when those people were close to me already.

Carter is a big guy too which is just a nice security measure to have. I figured Jessica would love the chance to learn this side of me and even talk to Ms. Cassidy if given the opportunity. After stumbling through my words and failing to make eye contact with either of them for what felt like 20 minutes I waited for their response.

Carter's tone was incredibly supportive and even helped me feel more normal about the whole thing.

"It is pretty normal for a lot of people to want that sort of thing. There is nothing wrong with that." Hearing that from him felt great and his support really made me feel more normal. He even offered to drive me to the event in case I got too nervous, his generosity knew no bounds.

Jessica's response was a bit all over the place. At first she thought I was seeing someone to help give me an out of body experience, like astral projection or something similar. Then she kind of laughed about the whole thing, wondering if I was actually serious about it.

Once she finally understood what I was talking about she jokingly said, "If you really want one so bad I could spank you."

Hearing that from her made my heart skip a beat, it was like a fantasy come true. I passed on the offer only because I knew her boyfriend would never allow it. Eventually she calmed down and was pretty supportive of it. I felt lucky to have such good friends.

Everyone else eventually came back to the fire and I made sure Carter and Jessica would keep quiet about things from the others. They respected my wishes, and even Jessica said she would keep it from her boyfriend.

Fast forward to the day before the big event and Jessica sends me a text telling me that she won't be able to make it. Her and her boyfriend had plans that day and she didn't want to tell him what she would be doing with Carter and I for the day. It sucked hearing that from her as I wanted her to be there as well but I understood. Carter had cleared his schedule for it and showed no signs of backing down. Everything was ready, and most of all, I felt ready too.