Missy, Mr. Windsor’s Naughty Little Girl

Missy, Mr. Windsor’s Naughty Little Girl

It all started at Shadowlane last year, I was sat in the lobby chatting to Jersey John and Tony Hamilton when along came this young lady to chat to the guys. Now I didn’t know her from Adam, I had seen her spank Sarah Rocks in one of the upstairs rooms but that was all. Other than a polite hi I actually sat back and chilled as they all talked. A few hours later I started my journey back to the airport and lo and behold, who was on the airport bus that I had boarded, none other than the same young lady who I saw chatting to the guys.

The usual immediate anxiety struck in when you see a pretty girl, her defensive mechanisms are going to be up so other than a polite brief conversation she will resort to her cell phone or IPod or something. Well didn’t I get a lovely surprise when this bubbly strawberry blonde started to talk like we had been friends for years. It was great to have such fun company and even better we had a couple of hours after check in so that we could hang out. Unfortunately that didn’t pan out quite so well because we were in different terminals and hers was backed up for miles, so after I checked in I went to search for this lady but it was too late, she had already left. Thankfully though, I had managed to secure a screen name, Missy Doright.

Very quickly I added her to Fetlife and as you do, I left her be for quite a while. Not for too long though!

You see, at the airport young Missy had said something to me that made me very happy, all based on a twenty minute conversation on the airport ride. She had asked if that at a future party that we may be at together, she wondered if we could play. Well, the pup ain’t no dummy.

I waited for a couple of months I believe before I sent an email, entitled “You are in big trouble, young lady”. If I knew then what I know now, I would have gone into character because Missy told me that the moment she saw the email her heart began to pace. You know that pace a girl goes through when she thinks she might be in trouble. That said mind you, I wasn’t holding out much hope because Missy was barely active on the site, so if I got a little response at some point I would have been happy, it was a tester just to keep a toe in the water.

Well it turned out to be a very good thing because Missy became a little bit more active and with some persuasion, she joined our little SSC group even though she felt she was intruding. She was welcomed with open arms and quickly became friends with everyone in the group. Everything was going just great until one day my Missy decided that she was going to be a little bold. During one of my happier moments I had posted a thread about the weight loss having reached 66lbs, and of course everyone was complimentary, everyone that is except one small person. Oh, her comment certainly could have been taken as a compliment, however, it could have also been taken another way. Would you like to see her comment?

“Congratulations on becoming Fetlife’s biggest loser”

Something told me that this might be a little tongue in cheek, a double entendre of sorts, in fact the young lady indeed admitted that she was having a little fun at my expense. That’s okay though, there would be plenty of time at the Weekend to discuss her behavior.

The introductions had been done, everyone spent the time renewing old acquaintances and meeting new friends and everyone went to prepare for the vendors fair. Once of course the party started in earnest it was a madhouse, so much fun and frolics going on and everyone having a whale of a time. It was during one of the fun instructional videos that I caught something out of the corner of my eye, a vision of white in the main ballroom. Being that I am drawn to white I had to turn around to see who it was that was wearing the white dress, and imagine my surprise when I discovered it was Missy, and that she was wearing the dress that she had bought specifically for our scene.

Well that was it, I had also come prepared so I scurried upstairs to put on my jacket and tie so that we could get our first scene done. That took longer than I had hoped of course because NOBODY at the party had ever seen me wear a jacket and tie before, save perhaps for Sarah Gregory at Pixie’s wedding.

It was finally time for the spanking and we headed back towards the booths at the back of the room. Other than spending a little bit of time with Missy we had never scened before, so this was going to be on the fly and I must admit, it was also a bit of a learning curve where we could pick up on each other. Surprisingly though, it went very smoothly.

I sat down on the chair and started to ask Missy about her comment on fetlife, was she being a sassy little girl? Well one thing that I have to give Missy is that she is truthful, so when the answer came I asked her what I said I was going to do to her, and her response was the correct one “You are going to give me one spank for every pound you lost”

“And how many spanks is that, Missy” I replied.

“66, Sir”

So I took the young lady over my knee for 66 spanks, yes, it was only to be 66 spanks. I’m not sure what she was expecting, but as it was only 66 spanks I wasn’t going to start on her beautiful dress, so the first thing I did was pull her dress up and bingo, it was 1979 all over again as she had purchased the PERFECT pair of white nylon panties. A vision that I had always dreamed of recreating and here it was, exactly what I had always hoped I would one day see again. The scene could have ended there and it would have remained an endearing image, but of course I wasn’t going to end it there, was I?

So I told Missy that she would need to keep count because if she didn’t she knew what that meant, which clearly she did as she replied to my rhetorical question “You will start all over again, sir”

So we are going to do these in sets of ten, I mean, she has nothing to fear, old Houndog has nothing more than a noodle arm, right? So ten spanks go by, and then another ten, and a third set of ten, man, this girl sure is squirming a lot for a little old noodle arm, plus I was gracious enough to allow her the protection of her underwear. I think it was at this point that the young lady was having trouble keeping count. Up towards 40 and the legs have started to gyrate, even looks like she is squirming forwards to escape. Unfortunately all this squirming around is causing her panties to become disheveled and now a lot of the contact is being applied to her bare bottom. Another set of ten firm spanks, the ‘Sirs’ are flying aplenty now as Missy answers my questions. Ten more firm spanks and ut oh, Missy has lost count.

Now then, in any other situation the pup ‘may’ have deliberately tried to alter the rhythm to throw off the bottom, but this was as close to a punishment as Richard Windsor has got, so I stuck to a game plan. So when I asked her how many that was she responded with “59”. There was silence which was followed by “It could have been 60”. So I was nice, I allowed her to reflect and think of her answer a little while longer to be sure that she knew what the number was. Finally, Missy made a decision, “60” she said. It was a guess, but it was the correct guess.

So all we had left was the final six and I remarked that she knew what this meant so she should brace herself. Down they came, one after the other very soundly to what was left of the scant protection covering her bottom.

It was fantastic, I was blown away by a scene that I knew was one of the best I ever had, and it was only 66 spanks. We hugged but I wasn’t done, there was still some dialogue to go. I told that if she misbehaved again during the weekend then clearly this lesson would not have be enough, so the next time it would be 100 spanks delivered in rounds of twenty, finally asking her “And where will they be applied?”

“On my panties, Sir”

“Correct, but they are no longer your panties, they are your naughty girl panties, and whenever you misbehave you will put your naughty girl panties on so that you know that you have a spanking coming. In fact any time that you decide to wear those panties you will know that they are your naughty girl panties as you pull them up”

And that was that, it was as close to perfection as you could come and it was pretty unlikely to be topped. At least that is what I thought, what I didn’t know at the time was that the session the next day would be as good, and the final session on the final day was perhaps the best spanking scene that I have ever been a part of, it was smoking hot and it is something that I don’t think I will ever forget. Even from the simple details of our eyes meeting for the briefest of seconds as she watched my movements from the mirror that she was facing as she stood in the corner. I would like to say that the final spanking couldn’t be topped, but I know based on our discussion afterwards that it can be, and it will be. Regardless of that though, I’m pretty convinced that time will tell me when I think back that it was the best roleplay scene I have ever done.

Back when I first met Missy at Shadowlane I knew immediately that I wanted to play with her, but I had no idea how good it was going to be. I was gushing about my Friday scene with her to everyone, probably to a point that I was annoying the snot out of them. Thank god there were so few people left after our final scene on Sunday. Mind you, I was so high after the scene that I spent most of the time after it on my own anyway.

There are two more parts to this story, and they are the following

Missy gets a public spanking.

Missy takes Richard Windsor to court.

Part four will happen in less than 5 weeks time when we meet up at the Florida Moonshine Party, though the scene set up has begun already with the email that Uncle Richard sent to his Niece, Missy, as she goes off to college.

I discovered this weekend after taking part in a weekend long roleplay that I love it. It wasn’t 24/7, but we switched it on at any given point, quite remarkable that we could achieve that. I have a feeling that 2011 is going to be my best year yet in the spanking world, if it isn’t already. Thank you for being such a big part of that, Missy.

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