Spanking Stories – Real Life

Ellee Gets Spanked

Now I’m not sure if we had talked about it beforehand in the earlier conversation,  or whether it happened on the spot,  but we both discovered that we liked to roleplay. So I was very quick to come up with a reason why my niece needed a spanking,  it was a real reason,  and Ellee began to plead her case. The first thing that I discovered was that this is one very smart girl,  she could think quickly on her feet and had me tongue tied. By the end of it I think that I was holding on to the flimsiest of reasons to spank her,  but then the magic happened. When I asked Ellee what I said I was going to do to her based on a previous discussion,  she lowered her head,  thumbed the hem of her pretty dress and simply said quietly  “A spanking”.



It is now 32 years ago that I officially began an actual life of spanking, a very fortunate experience that helped shape the person I am. At that point in my life I was very confused with my thoughts of spanking, certainly the beatings I suffered as a child were no source whatsoever to fuel those desires, and still I was fascinated by the whole thing. When you suffer at the hands of someone else for so long you develop a certain sense of survival skills, skills that aren’t measurable, but skills that nonetheless protect you from the outside world and the capability to form functioning relationships. The first time I ever trusted a girl to let her become my girlfriend wasn’t until I was 16 years old, that’s right, I had never sought to form a relationship with a girl until I was 16. Most of that came from the fact that I never wanted to subject anyone to my life, the fact that I spent every day of my life in fear, wondering whether this was going to be a good day, or a bad day.


A Weekend With A Good Girl – Friday

I’m not really sure what to expect, we have shared IM’s up the ying yang for a few months now, have known of each other for a few years, but we have only spoken on the phone once, that one is on the brat as she hates talking on the phone even more than I do. So I make myself busy at work and keep an avid eye on the phone, I had asked her to call me on the way to give me an idea of how things are going.

Having been burned last year, I was a little cautious when come 4.30pm there still had been no call, not an over concern as I had faith in the girl, but there was also that toppy worry that goes through us wondering if everything is okay. The phone call did come though, sometime around 5pm. The brat had driven straight through and was now five miles away in New Jersey. We chatted for a short while and tried to work out exactly where she was and how she was getting into Manhattan.

I’m clock watching and clock watching and clock watching, an hour has passed and still nothing, we’re coming up to 6.30 and the phone rings. Aurora has somehow missed her turning and is now heading south in Jersey, I can’t find her location on the map so I try to guide her off an exit so that we can find out where she is. From what I am guessing she is no longer on the turnpike


Meeting Amber Pixie Wells

It was the first time I had ever done anything like this, and I really wasn’t sure what to expect on this particular Saturday. Even as a lifelong spanko I had never used the resource of the internet to search for play partners. All of my play had happened with romantic partners or through clubs, which is kind of ironic really because now all I ever seem to do is find spanking partners through the internet, or at spanking parties. So who was the lucky girl who was going to share this memorable experience with me? Why it was none other than the dynamic Pixie! If memory serves me right, this was also Pixie’s first time meeting with somebody through the online community; in fact she even talks about the experience on her video interview with spankedsweeties. That let’s old Richard Windsor stroke his ego a little bit.

Pixie and I were both members of the online discussion forum and had exchanged a few private messages here and there. The dialogue really started when she invited me to come to the brat board, a place I hadn’t really visited as I generally stuck to the stories and the general discussion boards. She made it pretty easy for me on the brat board by making sure I was kept on my toes with her sassy comments.


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!


Missy Gets Spanked In Public

The first day was awesome and I was so looking forward to another session with Missy. The first event on Saturday was the Reformatory and I played my role with delight. At some point during the proceedings I saw Missy get up on stage and get spanked, at the time it was fun and I didn’t think anything of it, not until I was outside talking to her much later that day.

At some point I had gone to my room to rest and I decided to test the waters further, so I powered up my computer and started to type a letter to Missy. Here is what I wrote.

“Missy, I thought after our little discussion yesterday that you had promised me that you were going to be a good girl.

Lo and behold, what do I see today, my Missy Doright up on stage misbehaving during her exercise program!! Now I noticed that you were so bad that someone had to spank you right there on stage.

Well young lady, after our discussion yesterday, don’t you think for one little minute that that will be the ONLY spanking you are going to get for misbehaving in class today!! Apparently 66 spanks was not a sufficient enough reminder to keep you on track, so this time young lady you will be getting 100 spanks, and we will see if that improves your behavior.

So at some point this evening I want you to put on your naughty girl panties, you know which ones they are, because from now on we are going to refer to them as your naughty girl panties, and I want you to seek me out during dinner!!


Flashing Her Panties To The Boys

This was something that I was relishing as I dragged the chair into the middle of the room. What could be better than a shaking girl feeling repentant,  not wanting a spanking and submissively following my every lead? I began my opening talk with the following question  “So,  why have I called you here today young lady”?

This was it,  I was expecting some serious squirming and I was going to milk it for all it was worth. Give me an inch and I will take a mile,  scolding is one of my fortes and if I think that I can make a girl squirm then I will turn her face as red as a beet. What I got in return though was the complete opposite of what I was expecting,  the complete opposite,  her reply to me was  “I don’t know what you are talking about”


Friday Night Lights

There were many people to say hi to and some old friends with whom I hadn’t seen for a few years to catch up with. Of course one of the biggest goals of this party was to play and to make sure that the few items on my list that I had arranged actually got to happen. Whilst I had engaged in a private scene the night before my first real play of the party occurred with Alex Reynolds. Alex and I had plans for a punishment spanking later in the party so this was a nice way to develop a relationship beforehand with a warm up spanking.

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The New Year’s Eve Party

To start the day I want to tell you all about a great New Year’s Eve party that I attended over the weekend. A few weeks back, Pixie and I decided to get together to do something for New Year’s Eve. This really was probably going to be just hanging out together to see 2010 in. Well, a couple of weeks after this, the two of us received an invite from Funnybratgirl inviting us to a party at the house she shares. I was over the moon to be invited to such a party and after talking it over with Pixie, she was just as excited as I was, if not more so. So we had a change of plan, instead of me schlepping it over to her place, we decided that she would pick me up at a train station on the way.

Now the morning didn’t start as good as we had planned, my poor little feline friend was snowed under. But you can never stop a determined brat, and with shovel in hand and a determination to match, our Pixie snubbed her nose at a few snowflakes. Of course I had the same snow problem, but I live in New York City so it is public transport for me regardless of the weather. So as Pixie set out early due to the weather, I began the usual trip of bus, subway and train to get to my destination. When I got to Penn station I was disappointed to see that the train I had hoped to catch was cancelled due to the weather, meaning that I would have to get on a slower, local stopping train, which of course also meant that Pixie was going to be waiting for me for a while. At least I was able to call her to let her know that I was going to be late.


One, Perrito

What a wonderful time we all had at the New York event this past weekend. Friends of mine from out of state were visiting, so after work on Friday we all went to hang out. For the first time in a while I treated myself to some beers as Aurora and Publikk joined me for some fun. Believe it or not I didn’t play that night, though I did get to crash at the hotel room with them and passed out to the sounds of Publikk giving the girls what they needed. While I can’t go into too many details, this happened to me as I rested on the couch!! Never be alone with two brats in the room!!


Party Crashing

Before I say anything I really want to take the time to thank Ian, Headmaster Tony and Alona for the fantastic party yet again this year. Last year I said it and I will repeat myself again this year, this is my favorite party to attend. I know that there are many more people beyond the three that I listed that make this party the success that it is, and while I may not be able to name you all, you all know who you are and you should be proud of the efforts that you put in. The Florida Moonshine party and the SSC party that I attend will be on my calendar every year. Every party has its own special niche and I wouldn’t want to disrespect any other party at all, but the FMS party is played at the speed that I personally like. There are lots of organized activities for you to attend should you wish, but there is also a wealth of opportunity just to take some time out and do something different to give you a little break from the party as well. By late Sunday night I had pretty much crashed and burned, but in my mind that is because everything had been so good for the 4 days that I had been there. A very big thank you to the board of FMS, you will be seeing me at your party every year for sure.

Now then, I touched on it very briefly in my last post, and in this one I want to elaborate further with my thoughts. Last night I uploaded the first part of the video that I shot with Caroline Grey and as that will probably be posted tomorrow, please take the time to read this one now.


Santa And The Gingerbread Elf

The build up to the weekend was one of mixed emotions for me, on the one hand I was unable to afford to visit with my friends, ZED and Ginger, for the weekend, while coincidently a party had been arranged in New York that I was invited to attend. Now originally on the New York group I had told them that I wouldn’t be able to make it due to a prior commitment, but as the time came closer it became more obvious that an airline ticket was out of reach for me, so I made the plan to attend the New York party after all.

As luck would have it, I had been conversing with Audrey Knight from Spank That Brat for a while, and we had agreed to meet when she came to New York to do some work. Now never one to not be bold, I also told her that should she require my services then I would gladly don my Santa outfit and spank her on film. Audrey hadn’t considered that option at first, her reason for informing me of her visit was simply to tell me that she was visiting and wanted to meet up, but once I suggested it she was all over it like a naughty little girl peeking at her presents on Christmas Eve.

Now parties in general are something that I have a very hard time with, even though I can be an outgoing individual I am more apt to blend in on the sidelines.


Saturday Night In Vegas

What happens in Vegas stays in Vegas……… Yeah, RIGHT!!! :-)

It was banquet night at the Shadowlane party and the feelings of awkwardness crept in. I would say that I don’t pack a suit for weekend parties, but the truth is, I don’t own a suit. So the first feeling I had was that I was under dressed. The second thought was the one that probably plagues a lot of people at parties, just where do I sit. My first thought of course was to sit with the group, but then I did a quick count up in my head of how many of them there were. Of course there was no way that they would have turned me away, but I decided that I would mingle this time around as I had spent my time with them at the party as it was.

So I took a spot near the door and waited for others who are close to me to arrive. Now if anyone gets finicky over the order people arrived I will bite your head off :-)  Okay, so it wasn’t long before Sarah Rocks and her Husband arrived, along with Iggy.


The Errant Schoolgirl — A Roleplay

For some reason I have been thinking of this lately, it was a roleplay that my play partner at the time and I had done a few years ago. We only played over the summer of 2004, but it is perhaps my favourite partnership that was founded upon spanking. Raven was an amazing person and a wonderful play partner and I remember her fondly.

During the weeks of conversation, this was something that we had both agreed upon that we would both like to try, and probably very much enjoy. Raven was going to be the bratty schoolgirl and I her Professor. We saved this for Saturday night and we also both agreed afterwards, this was the best play session that we have had to date.

After a fun filled day we had relaxed for a while and talked about our plan. Raven excused herself into her room while I changed in the living room. After traveling all I could really dress in was a black shirt and black pants that was the closest I could get to be a professor this time around. Raven on the other hand had a full wardrobe at her disposal.


Getting the cane

Getting The Cane!!

For anybody who has never tasted it, let me tell you, it bites real bad, imagine the fear asscociated with it when you are a 14 year old boy. Though I have several stories to relate from a caning ( you tend to remember them ) this one sticks out a bit.

Up to this point, I had received either 1 or 2 strokes with it, depending on what the punishment was for. Each time had been alone ( always been a loner ) with both the Headmaster and the deputy head present. On this occasion, there were 4 of us, each sentenced to 3 strokes each, the reason, being caught with alcohol on school property ( the fields out back ). The other kids I was with I can barely remember the names of.

So there we are, the 4 of us outside the Head’s office, trying for all our might to be the big brave boys we were, though I am certain the hands of the other boys were shaking as bad as mine were. So the first boy gets summoned in and the three of us sat there silently. The Head was talking, but we couldn’t hear a word that was said. Then came that awful period, the complete deafening silence.