Spanked The Girls And Made Them Cry

Before I was able to post this I wanted to make sure that I had the approval of all of the girls concerned. Through some very long email replies I am glad to be able to post this with the permission of them all.

So far in this little world of ours I have always considered myself to be a blessed individual. Where else can you go to have such an emotional connection with people, many of whom you would have probably never met had it not been for what we do.

Throughout my first 50 years I have had one method of play, though within that play there are many different variations. Of course the play itself has only happened in the last ten years pretty much and I really think that this works to my benefit. I’m not somebody who knows it all, there is no one area that I excel in and dare I say it, there are more people who are far more experienced than I am in many different aspects of our chosen lifestyle. Despite the running joke about Richard Windsor’s ego, I honestly don’t have one, I’m a really humble man. There is still a large scope that I have yet to learn and I never want to be complacent enough that I think that I have all the answers to everything.

What I am going to talk about today is going to be very long so get your popcorn ready. I’m going to be talking about discipline, submission and the biggest one of all, the conflict that I am going through in my own mind.

There is no secret to Richard Windsor, I have been very open about this lifestyle of ours, how I fit into it and going through a long process of realizing what it is that motivates me and what makes me tick. Sometimes I have encountered negativity through this, because of my feelings regarding dress code I am susceptible to a certain portion of the female audience feeling that I am a chauvinist. By becoming more aware of what it is that I want though it has helped me progress with the battle that I have in my mind.

Many people have an idea of what it is to them that makes discipline work and I have found mine, It is very unconventional I will be the first to admit, but asking someone to dress the way that I like is more than something that I find physically appealing, though of course that has a lot of importance to me, it is all to do with the origins of discipline and submission. Every situation has to start somewhere and mine generally begins in that area.

You might be surprised as to the relatively small number of people who take a step for me in that direction. A lot of times you will hear tales of women asking men what it is that they want, and the man responding with a variation of  “Whatever you want is fine with me”. That drives me nuts because I can lay out a hundred different scenarios that would work for me, yet I consider myself lucky when I get just a small portion of that. I have told you all dozens of times though, the girls who do something with me in mind increases my fondness towards them tenfold. Those are the origins of submission to me, because those are the girls that I invest in emotionally.

One thing that has often been said to me is that at a party it just isn’t possible to cater to everyone, and to some degree that is true, but not always. I can guarantee that at pretty much every party I am able to connect to the special people in my life. I bring to the table what they want and in return they bring to me what I want. Clearly I understand the comments about parties, but if you want it bad enough you will make sure that it happens, and it is so important to me that I make sure it happens.

I’m at that stage in my life where I am not sure whether or not I am selfish, or whether I have accepted what is in my mind that I know what I want to strive for. You may have possibly read my writing regarding having an interest shown in me by the other person and how important that is to me. Seriously, I would rather play 5 times with people who want to play with me than play a hundred times just for the sake of playing. To say that I am as stubborn as a mule is an understatement, but it isn’t through choice, it is through my mindset.

There are triggers that work in a big way for me, both positive and negative. I don’t mind doing the dance in regards to spanking, but there has to be a point where your potential partner wishes to dance with you as well. I can lose interest in a heartbeat when I feel like I am getting the cold shoulder. Despite the UPT moniker it really isn’t that easy. For me to function in any type of play my potential partner has to have some interest. I’m very basic in that manner, if a girl is super gung ho about playing then guess what, so am I. If she is blasé then my approach generally follows in line. We might actually play but there isn’t much investment in the scene. At the very far end of the scale are the potential partners who want to make you work for it. Now I have no problem putting in a little extra effort, but little is the key word here, I’m not chasing anyone. If I have asked at various places 3 or 4 times and we still haven’t come close to playing, why would I waste my time? I’ve never gone short of play time. Seriously, think about it, why spend countless amounts of time chasing something that you might or might not enjoy, when you already have what you want waiting for you? It is a no brainer for me. Yeah, I come across like an asshole for saying that I know, but life is way too short not to enjoy yourself.

One thing that I have never really written about is submission and how it applies to me. Do I like girls of a submissive nature? More than you could ever imagine, it turns me on emotionally in the worst way. You only have to take a look at my history to get an idea of play partners. Honestly, some of my thoughts will never be shared on this topic, but they can run pretty deep. Submission at its core began in the paragraphs above, the connection made through the desire to interact. I’m quite a simple creature really, if you please me then I will want to please you.

Now we get in to the subject of punishment,an area that is a new one to Windsor. Over the last few years there has been a transformation for me. While I still love to play, there is a darker side. In fact some of my darkest fantasies involve some very deep events, so much so that I doubt if I will ever get to act them out. This past weekend I delivered three punishment spankings which all had the same effect, the end result of all three is that each girl cried.

You would have seen me write on the topic a great many times but in this post I am going to take it up a notch, which might perhaps alienate more girls from me but I am cool with that, I can live with it in order to be honest with myself. What I hope is that the people that it doesn’t turn off will have a better understanding of who I am.

When I ask someone to dress the way that I would like it isn’t just for me to get my visual jollies off, when these requests are met there is an empowering gift given to me that somebody wants to please me. This is the origins of submission that I already spoke of. When somebody invests in me then I become invested in them. Sometimes I think that I sound like a broken record because I have spoken about this topic many times, but a part of me really believes that a lot of people just don’t get what I am saying.

There is a slight conflict there though when it comes to punishment. Where punishment is concerned it really shouldn’t matter what a person wears because that equation shouldn’t come into it, but it really does for me. It is all part of the package that increases my dominance and it is a level of submissiveness that is important to me. All three of the girls mentioned above who shed some tears during their time with me, each one of them dressed with me in mind on some level. We speak often of the head space involved for a submissive but it is rarely spoken of for a top. Now I am fully aware that for a lot of tops they really couldn’t give a shit about what a girl wears, however, I’m pretty sure that there is “something”that makes it work for them.

There are a couple of things that I would like to put to rest before continuing. Whenever I write about things that make everything work for me there always seems to be a universal acceptance that some people will tell you that it doesn’t work for them so deal with it. What they are forgetting though is this is what does it for me, my writing is done through my eyes and not through the eyes of another. Dress is just one aspect in a vast cove that embraces me. It goes along with demeanor, respect, friendship, how one interacts with others etc. Right now I am about to really open up and give my feelings on some of these areas.

The first girl in my story made a comment to me a long time ago that really helped me see things for the way that they were. Now I have a huge conflict here with my own demeanor and approach to life and how it can affect the dominant personality that I also want to portray. There is no denying that I am a bit of a clown, I like to perform, there is no fear inside of me that I am going to make a fool of myself. Many of you would have seen the fun videos that we have done for BBW. Whether it is the creepy guy, the asshole, spankback mountain or any other role that I set myself up for, it is pretty clear that I have a very good sense of self-deprecating humor. There are times though that I think that I can set myself up where girls might not take me seriously.

I’m one of those people who really isn’t into bratting in any way, shape or form, but the line of what consists of bratting can be so vast that we might not even be able to measure it. There is nothing that I love more than cute and playful (think ellee acting like a prairie dog), being naughty for a reaction and a real sassy persona. My friend once described to me what is was, based on her interpretation, that the line was for me. It is to do with being emasculated. This isn’t just in person but in the written word as well, when the behavior never ceases. Every interaction is designed to make you feel like less of a man, and in this instance we are solely talking about spanking here. When there is a never ending license to do what one wants with no chance of repercussion. It may not even be deliberate, though there are many times that it can be. You only have to follow my posts on the spanking world to see the amount of times that the same people will try to undermine me. It is the biggest turn off.

We all have our own chemical makeup and that is one area that I learned really was an area that bothered me. Girls 2 and 3 in this story fell into that category in my eyes for a short period. The first of which is a longtime friend who I allowed to continue doing what she did and said nothing, mainly because she is a friend and what was happening was harmless, even though it really bothered me. For the most part that was my fault for not expressing my feelings, however, when I did express those feelings and asked for it not to happen again, it took very little time and with the aid of peer pressure it did indeed happen again. It is one of the few times that I was genuinely mad. You allow your friends some extra leeway when it comes to accepting things that you don’t necessarily like, you even allow them to undermine you publicly, but there has to be a point where your friendship is more important. While it hasn’t happened yet, the girl who applied the peer pressure and is also a longtime friend will also have that talk with me. More tears will be on the horizon. She should pay special attention to this post.

The final girl that I will write about I had a 100 questions going through my mind, the first of which, and perhaps the most important, was did I have any right to punish her at all. What she did, in the grand scheme of things, was pretty insignificant. In fact a good number of people are going to ask  ”You spanked her for THAT”?  When you read why you will know how I feel. In this situation I very much like what I have, and the last thing that I want is for that to change by a behavior that gets to me. Trust me, I have gone over the incident many times, even questioning myself, but I came to the realization that this really was important to me. I wanted to set a bar as to what I feel will make our friendship a very good one for many years to come. It will appear trivial to you I’m sure, but I don’t regret doing what I did at all. It is perhaps the biggest change in my life since turning 50, I’m drawing lines in the sand. For the first 49 years of my life I had never made a girl cry from a spanking, in a span of 24 hours three girls shed some tears this past weekend.

Have you ever sat back and evaluated yourself? What it is that you like, what is it what you want, and what it is that you are willing to sacrifice in order to get it? I think that as one gets older it becomes a lot easier to know what it is that you want. At one point in my life I’m pretty sure that I did everything in my power to be liked, even compromising a lot of self-worth in order to get it. That is something that has slowly dissipated over the years. Like anyone, I think that we all want to be liked, but as the years have gone on it isn’t something that really bothers me anymore. Life is way too short to make friendships hard work. I’m open to letting anyone into my life, but just as quickly I am open to shutting the door as well. I’m as blessed as any man can be, I have such wonderful people in my life that I don’t need to work to get friends.

In a way I feel like I should have my biography written already so that people can understand the reasons that make me act the way that I do. When I grew up I had a horrible life, but I made a vow when I became an adult to never let anyone treat me that way ever again. There really is no middle ground in my life, if you like me then I like you, that’s all I ever ask for is for people to be nice. If you are unfriendly towards me, whether you are male or female, then move on, I want nothing to do with you. I’m 50 years old now, I know how people are supposed to treat each other. Like I said, I know where I come from and I will never allow myself to be treated as less than equal to anyone.

The first girl in my story will not be named. This is someone who has helped me improve my respect for myself. I have always been pretty confident but she added a female perspective to it. It would be fair to say that over time this has been the first friendship where I stepped up my game a bit and started to institute rules. They were very simple, it wasn’t much of a request, but many spankings later we got to a point where what I was installing at spanking parties started to have an effect on her real life. The rule that I had in place became common practice for her in her everyday life and she freely admitted that it helped her.

At a party this year the improvement was remarkable, we went the whole weekend without incident, until the final day. In fact it was KlutzofNY who first heard that there had been a lapse in the rule and she feared for my partner. She was right to feel that way because I addressed it immediately, in front of everyone. Let’s be real though, once in an entire weekend wasn’t so bad so a hand spanking would suffice. Unfortunately, not 30 minutes later the same mistake happened again, only worse this time.

Due to the party finishing it was an owed spanking and this weekend is when it was cashed in. I took the girl down to my room and let my feelings be known, telling her what the potential consequences could have been had it not been for me. In fact I told her it was the maid and it is only as I am writing this did I realize that I was the one who saved the day. I’m not going to say what it was, but the girl could have left the party and caused herself some major grief had I not made a discovery.

So now the punishment, it was intended to be swift and hard, make no mistake. It wasn’t long by any means but I talked throughout and laid the leather paddle down without mercy. She held in well, right up until I told her that she had ten to go. On number 7 the whimpering stopped, it was replaced by tears. For the first time in my life I had spanked someone to the point that they cried. It wasn’t really from the severity of the spanking, it was with the combination of my words. Years ago that would have bothered me tremendously, but in this instance I didn’t blink, there were still three swats to go. The punishment was well deserved, a benchmark had to be placed and I laid it down. If it happens again I have a feeling that the tears will come long before the spanking is over.

The second event that happened just so happened to be the very next spanking that I gave. It wasn’t planned, it was just supposed to be a play session, but as the spanking began Kat made a sassy comment that put me in a toppy mood. I reminded her of what she had done and that she was still owed what I had promised her, and I quickly turned the play into something serious. Okay, perhaps I didn’t follow the punishment mantra here, but the timing was right.

A long time ago at a spanking party,an event happened which was very humorous for the girls. It was actually funny and I played into the joke, gave a fun spanking and all was done with. The picture of me that was drawn was then posted online and again, I’m game for a laugh and I played into it. Then another pic was posted, and another, and another, in fact it never ended. Practically weekly the joke continued without my involvement. Now as I mentioned earlier, these are my friends so I sacrificed my feelings in order for them to have their fun. Yeah, it did bother me but it wasn’t worth getting in a tizz over.

Here is the thing though, it is that one line that I not only have a problem for myself, but for other tops as well. This never ending process of undermining a top for a cheap laugh. Now I know that there are going to be many girls who disagree with me here, and one person’s play is another person’s nightmare, but I really draw the line at the point that I think it becomes disrespectful to the top, especially when everyone else can see and people start to feel sorry for the top. If there is one piece of advice that I can give to girls it is this. Have your fun, but know when to stop!! Never get to the point where other people are thinking that this is now becoming disrespectful, because I can assure you that the top thought that long ago, no man ever wants to feel emasculated, most especially in this world of ours. Even in online conversation and banter, know when to draw the line and offer some acceptance of the tops role. This might make for a good discussion, but I feel pretty sure that we all know where the line is.

So it had happened again, this picture once more surfaced with a threat and I clearly stated that I didn’t want it posted. Amber Grey decided to join in and egged Kat on and the picture was posted, that really made me mad. This time I wasn’t playing around and I very quickly requested that the picture be removed immediately, and did so quite sternly as well. The seal was broken, all of a sudden two girls realized that they had stepped over the line, and in my mind it was way over the line. A long discussion followed and while I understand that Kat was upset over it, so was I. She removed all previous pics which really wasn’t necessary, as I have stated both to her and on here, I can’t hold her accountable if I never said anything.

So the mood has changed and I am now spanking Kat and reminding her of her transgression. My understanding of Kat is quite high and I know that her mindset here will affect her if I am spanking her for real. The feisty Kat has long left us and now I have a contrite girl on my hands. At what point she started crying I have no idea, it could have been during the hand spanking but if it was then I didn’t hear it. During the caning though it was quite apparent that there were some sobs.

Kat was due to get 12 with the cane, but on the 5th stroke the cane broke. Now my room was mere feet from where I was standing and I could have retrieved another cane, but here’s the thing, Kat was already crying so my point had been made. I don’t need to be that rigid to make my point, the point had already been made long before the spanking ever occurred and I know that Kat felt dreadful over it. The caning was almost irrelevant really, just a tokenistic enforcement of how I was made to feel.

It is a very difficult balance and I never want to take away anyone’s fun, but when that fun is at the expense of someone else there has to be a line drawn, whether it is self-drawn or enforced. So my advice to anyone if something is bothering you, speak up about it and nip it in the bud. It was never Kat’s intention to upset me over this, and by not speaking up I allowed it to blossom. On the other side of things, don’t give yourself free license to constantly go after someone, at the very least check in with them, especially if they stopped participating six months before. Even the BBW owners check with me first before casting me in the role of an asshole to be seen by the entire spanking world.

Now we come to the finale, and out of all of the tears from the weekend, this was perhaps the most unexpected.

If you have followed me for the last 8 months you would have seen many a picture and read many a story involving the wonderful girl who is known as ellee. So many wonderful memories already, and keepsakes that will provide us both with enjoyment for decades to come. This is ellee we are talking about, a girl so good you could almost feel guilty for spanking her, if she didn’t enjoy it so much.

Now I’m going to lay a true confession down as I mentioned at the beginning of the post, when I spanked ellee for real it was for the most trivial of reasons on the surface, and I’m even going to tell you what it was that she did.

It was somewhere around 6am and we were all playing a game where the girls always seemed to end up getting spanked. During one round ellee and KlutzofNY were hugging right in front of me so I waited for them to finish to be seated, before I could do that though, ellee looked at me, pointed at my seat and said  “Sit down”. The top gene rose right to the tip of my forehead which was very quickly noticed as she scampered back to her seat. Unfortunately for her she was sat right next to me. That simple gesture bothered me, in fact I won’t tell you what it made me feel like but it wasn’t pleasant. There was a small piece of humiliation wondering just how many people saw it and what they might have thought, how many pairs of eyes rolled.

It doesn’t sound like much at all, does it? To me though it was something that I didn’t want to see, nor do I want to see in the future, to be directed by hand gestures. Ellee is a very special girl and she means a lot to me, in fact I have even gone as far as to say that she is the one person who dragged me out of the shell that I had fallen in to. Every thought that I have of ellee is a positive one, she makes me a really happy person, I can’t allow our friendship to take a different direction by not addressing an issue that came up. There are certain creatures that you direct with hand gestures, I’m just not one of them. I did what I did simply because I like ellee too much and I value our friendship tremendously.

Despite my feelings,and even after admonishing her immediately, when the next day came around I really figured that I was making this a mountain out of a molehill, but I was bothered by it. During the day on Sunday I took a long walk around the lake, playing things over in my mind and wondering whether I should let it pass. A hundred questions I asked myself, the most important of which was this, do I even have any right to spank her for real? We were at a spanking party after all and this is supposed to be fun. The thing is though, she really does mean a lot to me and if I let it happen once then I just as well accept it as standard. I think too much of her to allow that to happen. I think of ellee as that mock prairie dog who was looking over the couch every 5 seconds to see where I was, who ran and hid behind and under things when a spanking was coming, the girl whose energy rubs off on everyone she meets. I never want to think of her as the girl who issues directives by pointing a finger as to where she wants you to go. Yes, I admit that on the surface that it appears trivial, but she was important enough to me to want to draw a line quickly.

For once it wasn’t a game for me, and I don’t think it was for her either. In fact ellee herself may have felt it was trivial, I’m really not too sure about that, but I do think that she feels that if I felt it was important then she would too. You can put your own thoughts on a postcard, but do bear in mind that I don’t need a reason to play with ellee, I simply have to ask her. At no point do I go looking for reasons to play. ellee is an incredible person, one of the nicest people I have ever met.

When the event occurred I took her by the wrist and led her to the library room, for some reason I felt that the ambiance would add to the mood. As soon as we got to the room I put ellee in the corner and told her to wait for me, and then I went back to the living area. Now ellee doesn’t know this, but while I was there I talked to Jules and at one point I shrugged and stated  “I think she might cry”.

It wasn’t something that I was banking on, it was just a feeling that I had from looking at her face. When I returned to the room I called her to me, took her hands and placed them on her head and then pulled her skirt up. I had run this over in my mind beforehand during my period of reflection, I stated to her the following sentence “Now I’m going to ask you a question, but before I do so I am going to help you with your answer”  and I proceeded to spank her thighs 6 times.

Next, I asked her the question  “At what point in our friendship did you become comfortable enough to direct me around with hand signals”?

Ellee couldn’t answer right away other than to say she was sorry, she just covered her face and despite being warned to put her hands back on her head she just couldn’t do it. Six more spanks to the thighs later and we were back to where we started. The mood was pretty dark and her answers were very quiet, all of which were interspersed with the words  “I’m sorry”

I have played with ellee many times and I have spanked her pretty hard on occasion, but this spanking was a simple hand spanking. As I lectured her during the spanking I could see that she was uncomfortable, covering her face or playing with her pigtails when I asked her a question. Now I had planned to spank her for far longer than I did, but the heat in the room was gross, but I made sure to announce that I was pulling her panties down to her knees during the spanking and that is exactly where they ended up.

Perhaps this one gesture had a small part in how she felt. Ordinarily when we have finished playing I pull her panties back up, but this time I didn’t, I simply told her after her hand spanking to pull her own panties up and to go back to the corner as she had a caning coming.

Now I am not totally sure of this, but I think that ellee became teary eyed and started to cry as I was spanking her, once she got to the corner however, that is when the tears really came. For three minutes the only sounds in the room were the sounds of ellee sniffling and sobbing. Ellee was in the room by herself but I had an audio running of our interaction, and I only found out just how much she cried long after the event.

Why this happened I have no real idea other than ellee knew that she had really done something that actually got to me. When I moved ellee into position for the cane I will have to be honest, I actually thought that she was going to cry throughout it, but she didn’t, between the corner and taking up position she managed to pull herself together. Okay, during the first two strokes there was still a lot of sniffling, and towards the end as I looked at her, I noticed that she started to shake her head in a no motion and I thought that she was going to start crying again before the final strokes landed, but she didn’t, ellee managed to hold it together. When it was over we talked for the longest time with her curled up on my lap. Even then I asked her whether or not she thought the reasoning was trivial, and she started to answer but decide against it and just laid her head back on my shoulder.

Upon reflection it doesn’t seem like much, but I adore ellee and I want nothing but positive thoughts of her. In my heart I really don’t believe that she understands what that gesture meant to me, and at the same time I won’t over emphasize it. What is important to me is that ellee understood that I felt she had crossed the line and she accepted it, that means an awful lot to me, it really does. Throughout everything that happened over the weekend, this is the one moment that was the most powerful for me, it was very moving. If I have listened to ellee alone in the corner once, I have listened to it a hundred times.

Why it happened that way I have no idea, that is something that only she can answer, but to tell you the truth she doesn’t need to, I am fine with her keeping that to herself. There were two lines that she said to close the event that had a big impact on me, firstly it was the line  “I haven’t cried from a spanking in a really long time”, and the other made me feel really proud, and that was  “Thank you for spanking me”

The first two spankings I had expected tears, and while I thought the third spanking might produce tears, I was still surprised that ellee cried.

Now for the important part, did any of this bother me?

Not in the least!! At one point in my life I never wanted anyone to cry during a spanking, in fact it would have bothered me, but now I am far removed from that. In situation one the tears could have started immediately and I would have carried on. Kat held herself together for the most part and only really cried at the end, and if I’m really honest, I wanted ellee to cry throughout the caning just to let it all out.

A big part of me changed this weekend, even KlutzofNY had moist eyes when I finished spanking her right at the very end of the party. I was pleased with how I handled things, my demeanor was calm during the lectures, perhaps it worked well because I am normally a super happy guy that it was strange to see me act in this manner. These events contributed heavily I think to the post party drop that I am feeling right now, it was a good place to be. My views on submission increased dramatically and my role I also think increased significantly.

Where do I go from here though?

My dominance is at an all-time high and the first thought was to offer my services to the girls in question, that if there was anything troubling them that I could help with then I would gladly do so. That isn’t my position or role to do though, these were one off events and we all have our own lives to get back to. Perhaps there is an outlet for them though, if they ever find themselves in a position where they do have no place to turn, they know that I can help them free themselves from what is on their mind by reaching out to me.

Do I have any regrets from the events that took place? Not at all. I think that my bond with each girl became stronger and even if they don’t feel the same way, they each mean a little more to me because of what took place. I enjoyed steering them right, providing guidance and some catharsis, the tears didn’t bother me in the least and I was more than content to spank a sobbing girl, as I will be in the future.

Things have changed, Amber Grey and Prux will find that out firsthand the next time that I see them both. I’m still the same person that I always was, but now I draw lines in the sand. Many girls like to tread that fine line between good and bad, it’s just that now I plan to call them on it.

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