It has been a while since I last told a tale of a real life spanking that I have given. There was one that happened recently though that has brought me out of a bit of a spanking funk and has renewed my excitement about the future. One area of spanking that I have put on the back burner for many years now is the art of roleplaying,  and this special person has helped me to realize just how much that I love to do it. Often I have talked about quality over quantity and this solidifies my view on that because this has the potential to be a very special event for me. Actually I should say that it has already been special and my hope is that it continues.

Just to give you an idea,  there are many different scenes on spanking sites on the Internet that you would have seen that I have devised and created. Creativity is something that stimulates my mind and nothing makes me happier than to be asked for my input in creating a spanking scene for a company.

At a previous party a girl by the name of Ellee had approached me to tell me that she had been reading my writings for many years now. We chatted for quite a while and my immediate thought of course was to ask her to play,  but that is one area that I’m not so good at. When I meet someone for the first time at a spanking party I hate being one of the folks who immediately says  “Would you like to play”,  it just seems so impersonal to me. From my past experience I have to chat to people first,  and if a play session is meant to happen then it will probably do so the next go around. It might be an approach that I need to change,  but I have always been the type of guy to actually want to know someone first. From the first interaction I certainly wanted to,  but at the same time I didn’t want this to be the only interaction ever between us. I wanted a mutual connection on some minor level. Being that I am always super careful with someone who I don’t know during the first spanking,  it might have been a disappointment for Ellee had we played that night anyway.

The following week we got to meet up again at a different party,  and as usual the nerves were there for me as they always are at a party. This time there was spanking going on and my desire to play with Ellee was high. After some milling around,  Ellee came my way to chat,  though if my inkling is right I think she was also saying  “Here is my dance card,  would you like to play”?

This is one area that has always been a struggle for me. Now I know that the onus is on the guy to do the asking and I have no problem with that of course,  but just walking up to someone and saying  “Would you like to play”  without any interaction at all is something that I struggle with. This is where the girls can play a key role by showing some interest in playing with a guy,  to allow the guy the opportunity to pop the question,  by letting him know that she is okay with it.

I think that I am fairly blessed in knowing who wants to play with me and who doesn’t and generally I can get a good read on people. You don’t really need to be a genius to be able to work this out,  you just have to be honest. Obviously I never go short when it comes to playing so perhaps I am more in tune with myself. There are a lot of girls who show eagerness to play with me so that tends to be my focus. That is a different topic for a different day though. Ellee had made it well known to me that she wanted to play with me so it allowed me the opportunity to play the game,  to propose a play date. I guess I am a little old fashioned that way.

This time the pleasantries with Ellee would also include some spanking talk as we chatted,  and when the time was right I asked her if she would like to play. Now my memory isn’t something to be proud of,  in fact I can forget what I did yesterday pretty much,  but the words that came out of her mouth I remember very clearly  “I would like that very much”  were the words that she said. While I may be known as the ultra popular top,  those words were like music to my ears,  it sounded beautiful. Despite popular belief,  I am ALWAYS really honored when someone truly wants to play with me.

So I wanted to avoid jumping straight in and I told her that I would be looking for her,  which wasn’t going to be that long I can assure you,  a little anticipation can go a long way in my eyes. When I returned to set up the play date she was gone!! It’s a spanking party after all,  so this time I stayed where I was and I waited for her return. That isn’t something that I normally do,  wait around for someone,  but I wanted this to happen as much as she did. Once she did return I allowed for the recovery time and after Ellee and I made eye contact,  with a nod we knew that we were both ready and I gave her a playful  “Go up to your room young lady”. I’m not even sure if she heard me say that,  I sure hope that she did.

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 moments like this that define spanking for me. Seriously,  girly girls drive me insane and Ellee couldn’t have looked any more girly than she was at that point,  so vulnerable and dare I say it,  cute. If you have read about me for a long time you will pick up on the things that enhance a scene for me,  Ellee had just done one of those things.

The alpha male adrenalin surged through my body. Now I knew that mistakes were going to happen during this play session,  it was the first time after all and it was to be a foundation for the both of us. Ellee went over my knee on the bed and for as long as I could manage from that position,  I warmed her up through her dress,  then the slip that was attached to the dress and then finally the treat,  the cutest unicorn panties you ever did see. By the way,  the whole time that this was happening,  Ellee had the smaller of my ivory hairbrushes on the bed in front of her.

Of course I really wanted to have Ellee otk,  but there was no chair for us to use,  and with the bed not providing my body with any support we had to change positions for her to go over one knee. Once the hand spanking was over I asked Ellee to pass me the brush. It was something that I happened to notice,  but she didn’t give it to me straight away,  instead she studied it first. One of the scene breaks happened during this time as well. I’m a party veteran after all and Ellee is fairly new to the scene,  but that doesn’t mean that I have to forget my manners. Stopping the scene as I delivered the hairbrush to the seat of her panties I had to pause and ask her  “Are you okay with your panties coming down”?  It presented no problem for Ellee,  other I think than her thinking that it was an unusual question for me to ask,  so I resumed the spanking,  and when the time was right I told her that she was now going to be spanked on her bare bottom.

Now this wasn’t a hard spanking by any means,  nor was it meant to be,  I wanted to learn about Ellee here. The little nuances that I could play off for future events,  her demeanor,  her fighting spirit,  her resignation. It may surprise some people but that is something that is very important to me,  I want to know what works for the person that I am playing with and I hope that they afford me the same courtesy. It all added up to one wonderful scene. When all was said and done I pulled up her panties while she was still over my knee (always do that to be respectful guys) and yet another error occurred when I pulled the panties up so well that the left side gave her a huge wedgie,  lol. Afterwards Ellee sat on my lap and I noticed straight away,  mild spanking or not,  her butt was on fire. This was a getting to know you spanking and I couldn’t be happier,  I knew right there and then we could produce some good chemistry going forward.

Later on Ellee had stated that she wanted to try my Malaysian cane,  and of course I would be delighted to give it to her. As the night drew near I waited for an opportunity for our paths to cross for what seemed like hours,  before coming to the conclusion that it wasn’t going to happen. Everyone had gathered from upstairs to say goodbye and I rued a missed opportunity,  it was something that I had built up in my mind and I was a little disappointed that it wasn’t going to happen. Before Ellee put her coat on though,  she looked at me and said as she smiled  “I would like to try your cane one day”. Well this isn’t my normal style at all,  but I had been waiting for a good part of the evening to do this,  and as everyone was putting their coats on I got very toppy and said  “Good, let’s do it right now”

Now I know what Ellee is capable of taking from having looked at her pictures,  but that is never my goal in life. There is an old adage that I always apply,  just because a girl has been known to take it,  it doesn’t mean that you have to give it. When I play with someone I do so as I would with anyone,  the first spanking will never be a serious one,  nor perhaps will the second one be. The level of the spankings increase as time goes on. This could be one of the reasons that I am successful in finding play partners,  by building up a trust between the two parties from the get go. Ellee will find out what most girls find out as time goes on,  when it is time to be serious then it will be time to be serious. The friendship is more important to me first.

As Ellee’s husband took the pics I had decided on giving her six medium strokes with the cane. Once again,  I’m careful with a cane,  but I could tell right away that Ellee could take what I was giving quite easily. So as her husband complained that he couldn’t get the right shot I increased it to twelve strokes. Unfortunately it was super late and people wanted to leave,  so after stroke 9 we had to cut it short and I said that I would give her one more. Knowing it was the last one I picked my favorite spot,  right on the underside of the cheeks,  something that I had hoped would make Ellee shift uncomfortably in her car seat. Once again there is one of those little things that I adore that happened. After the hug,  without a care in the world Ellee held her dress up and started to rub her bottom through her panties. That type of thing makes me smile a lot and I quickly snapped the camera up from her husband and grabbed a pic of it happening.

After this evening our friendship picked up via email. We shared ideas and thoughts,  put together a roleplay where we would both be in character throughout,  and I even bought her a pair of white nylon panties to wear with her uniform. It was going to be months before this happened,  but it was something to look forward to. Whenever I do a roleplay with someone I try to put in as much effort as I can because it is the intricacies of a scene that could make or break it for someone. It is certainly the case for me so I assume that it is the same for others. In fact the more that I think about it,  even if I am giving someone a serious spanking I put as much effort in. Ellee’s friend Alex will find that out soon.

Just after Christmas something happened,  Ellee had emailed me to ask me if I was going to be somewhere on New Year’s eve,  just imagine my delight when I found out that she was going to be there as well.

The roleplay that we have set for later on is safe and I didn’t want to ruin that special occasion, but the moment that I knew Ellee was going to be at the party I devised a new plan. We have a school scene planned for the future and my creative juices started to flow,  perhaps we could do an Uncle/niece scene as a prelude to the schoolgirl scene. All I did was give Ellee the basics of her being sat in her bedroom in her pajamas waiting for her Uncle to arrive,  she had no idea of how much work I was going to put into this scene.

The first thing that I did during our email exchanges was to create a template of a school letterhead and type a letter from her headmaster to her Uncle. This was something that I did that was based on our conversations and by reading her profile,  to try and find the little things that I thought might work for her. The scene that I played over in my head was of a girl who still gets spanked sitting in her room reading a letter from her school detailing her misbehavior. Try and imagine yourself in that position as you are waiting for the inevitable,  there was no way in my mind that I thought that this trick would fail.

Ellee had no idea about any of this until the day of the party itself. To tease her I had let her know about the letter during the party and at one point she flat out asked me with an anxious look  “Do you really have a letter”?

My response was wicked,  with a grin I replied  “Oh yes,  and you will have some explaining to do”

That was the time when I produced the letter from my bag to show her that it existed,  only to show her there was a letter mind you,  she was still going to have to wait for it. That is part of the preparation that I had planned,  I wanted her to think about this letter,  to be able to get her mind in the game,  and I think that it worked. Once she saw the letter she acted a bit frantic and you could almost hear her tummy rumbling.

Now all week leading up to this event I had played things over and over in my mind,  what I was going to do,  what I was going to wear,  what I was going to say,  all the little things designed to make her squirm. When I got to the party there was no Ellee,  and hours went by where I felt a little deflated having spent so much time putting in the thoughts that I had done. It was at a time where I had assumed that she wasn’t coming when I overheard someone say that she would be there at a certain time. Oh man,  now I was pacing,  running the thoughts back over in my head,  my excitement level was at a fever pitch. When Ellee arrived she was already in her pajamas which just increased my desire to act this scene out with her.

It is a party and I didn’t want to rush anything,  I never do. I bide my time and decided that after midnight,  once the New Year was upon us,  that was the time when we were going to do this. I could sense the excitement in the girl,  she wanted that letter more than you could imagine and made mention of it several times,  that is why I kept delaying the scene itself,  to keep her on her toes. Like I said,  we are now in character,  and the moment that I start we are going to remain that way. It is difficult being at a party but I scoped out a room,  grabbed the letter and then it began. When I approached Ellee she was smiling,  it told me that she wanted to be a part of this event.

In the sternest voice I could muster I said  “Ellee, I received this letter from your school today and you have some explaining to do. Now you take it upstairs to your room,  read it,  and you think about what you have to say to me”

Ellee was gone,  I have never seen a girl run upstairs that fast in my life. I will be damned though if someone hadn’t grabbed the open room while I was preparing the scene. The empty room was the one I wanted,  the one with a vanity at the end of the bed that I could sit on and put Ellee over my knee,  but that was the one that had just been taken. We had to step out of character a little bit as we waited for a room,  but shortly afterwards we had one and I just turned around so that Ellee could go about her business.

The letter was long,  but besides that I was going to make her wait anyway. I wanted her to read the letter,  digest it,  and think of what she was going to say to get out of it. As eager as I was I had already played this out in my mind over and over,  to get inside of her mind I needed to give her the time to spend on her own. I was to find out that later on that it had indeed worked. Ellee had read the letter twice,  even concentrating on certain sentences more than that.

Now before I go on,  earlier in the evening I had given her the white nylon panties and a part of me wanted her to put them on for the scene. This should give you some idea as to how important the schoolgirl scene is to me though,  I want that one to be really special,  and the panties are a part of her uniform,  so that thought left my mind quickly. I had already seen earlier in the evening that Ellee had on a very small pair of red panties,  and though she didn’t know it at the time,  her pajamas were coming down from the get go so they seemed perfect for this purpose.

The details are so important to make this work. I picked up my brush and walked up the stairs,  just like that famous picture of the girl with the covers pulled up to her chin as her dad stands in the doorway holding the hairbrush. I don’t know if Ellee had heard me or not as I was coming up the stairs,  but soon I knocked on the door. I heard no answer so I walked straight in to see Ellee sat sideways on the bed toying with the letter next to her,  almost like she was wishing it away. She didn’t look at me at all,  Ellee looked squarely at the brush that I was holding and with a pout and a deflated sigh she looked away. Placing the brush down on the dresser I asked her while standing with both of my hands on my hips.  “So,  what do you have to say for yourself”?

There was a shrug and then she began,  every excuse that she could think of was coming out of her mouth and at one point she almost had me. I’m telling you,  this is one smart girl here. Nothing was going to let her talk herself out of this one,  as much as she tried. Allowing her ample time to give an explanation I decided that the time was now right. Walking over to Ellee I grabbed her by the upper arm (I pay attention to detail also) and told her to stand up and it was now that she realized that it was going to happen  “I’m sorry I lied”  she said as she twiddled with her fingers,  hoping that this admission would somehow suffice but quickly asking as well  “Do I have to get a spanking”?

“Yes,  you most certainly do young lady,  and what’s more,  it is going to be a good sound spanking at that”

Ellee hadn’t given up totally though,  there was some fight left in her as she contradicted herself when she mumbled  “I didn’t really lie,  technically”

Man do I wish that I had a chair at that point,  in retrospect I should have made her wait for a while as I got one. I’m 5’7” and sitting on a bed to give a spanking just doesn’t work for me. There is so little space for proper arm movement and the back is unsupported. So it was over one knee again and the pajama bottoms came straight down. My goal had been to spank her soundly with my hand from the start,  but the position I was in wasn’t conducive for me,  it certainly wasn’t as thorough as I had wanted it to be. So I did the best that I could for a couple of minutes before telling the naughty girl  “Now I want you to stand up and go and bring me that hairbrush”

Like any good top I watched her red bottom glide over to the dresser as her feet tangled up in the pajamas at her ankles,  and then I got the treat of the last act of defiance when Ellee picked up the brush. A foot stomping girl making a declaration  “This is so not fair,  I don’t want the hairbrush”. Yes,  right before she was about to get spanked with a hairbrush she had a little tantrum.

With a pout to sink a battleship she reluctantly brought the hairbrush over to me,  carefully studying the back of it as she did. Taking the brush from her I then gave Ellee a lecture about her behavior,  and then a decision that I had made for the future  “Now I spoke to Mr. Windsor at your school and I have given him my permission to punish you as he sees fit from this day forward. Not only that,  but if you get punished at school you are also going to get punished when you get home”

There was more pleading,  Ellee was frantic for me to reconsider my decision,  these were words that Ellee didn’t want to hear,  but my decision was final and I took her back over my knee. She was playing the game to a tee.

“I promised you a good sound spanking young lady and that is exactly what you are going to get,  and that spanking is going to be on your bare bottom”

The panties quickly descended to her knees and I took up the brush. Now again,  while Ellee may disagree,  my use of the brush was methodical and firm,  it wasn’t hard by any means. My goal was to make it sting but to keep the element of surprise for later. My words were what I had hoped to use to drive the message home. Now I have no doubt that it stung a lot and at one point her hand came back as well. Perhaps I could be wrong here,  but I believe that Ellee was offering me a little piece of submission by doing this,  a silent  “Hold my wrist please”

The hairbrush spanking went on for a while and it wasn’t long before her legs began to kick. As I had a hold of her wrist I thought why not,  and I locked her legs between mine as well. The girl was now pinned. I will tell you this though,  the feeling of her little legs trying to kick in between mine was the most awesome feeling in the world.

Her bottom was peppered for several minutes with the brush but as I mentioned already,  it wasn’t the worst spanking she will ever get. There is a method to my madness,  one day soon Ellee will know the difference between a proper hairbrush spanking from her Uncle and the reminder one that I gave her on New Year’s Eve. If the playing status continues as it currently is then it is a feeling that I believe will not only be noticeable for her,  but it will be something that she will appreciate as well. It is my firm belief that when you leave something in the tank it increases the stimuli for the next go around and just makes that scene even better.

When it was almost over I gave Ellee some positive encouragement with my words and by rubbing her back,  but we had to finish with a round of harder spanks to drive the message home. Once her panties were up she sat on my lap and I told her what I expected from her for the future. My words perhaps didn’t carry the exact message that she wanted to hear so she flat out asked me  “Am I forgiven”.

Of course I reassured her that she was forgiven and that produced a smile on her face,  and dare I say a little sass as it was at that point that she decided to ask me a question  “If Mr. Windsor spanks me for this same reason,  will I still get a spanking at home”?

The little brat,  of course I can’t spank her for something that I have already spanked her for.

She thinks that she is a wily little girl though? I have tricks up my sleeve for her let me assure you. Her uncle can’t spank her for what she has been spanked for already,  and that is what her headmaster will be spanking her for as well. What Ellee doesn’t know yet is that she is being caned by the headmaster for a different reason,  and that is a reason her uncle hasn’t spanked her for. It is a pretty bad reason as well and I have a feeling that Ellee has just talked herself into another spanking,  and her Uncle’s belt will come off for that one. This is the first that she will be hearing of this. For the later scene Ellee is going to be given a punishment slip by her headmaster,  and on that slip will be the reason that she has earned the cane. If she is getting the cane then it must be for something serious,  and trust me,  it is all planned out already. Ellee had once confided in me that she has never been spanked for this reason before,  so there will be a definite air of realism involved. Ellee will be able to work out what the reason is from this story,  and from this day forward she will now have to think about how bad the consequences are going to be for her actions!!

Once it was all over we walked out of the room,  still in character,  but crossing the threshold she couldn’t contain herself anymore and Ellee’s character left her. Bouncing up and down on the floor and throwing her arms around me she declared  “That was so awesome”. We talked about it for a while,  all the things that worked and how important the letter had been for her. I felt very proud I must say,  all of the effort that I had put in had proved successful,  there was a content girl and if she was content,  you can bet your bottom dollar that I was as well.

So to me the story builds. I wanted a couple of play dates with Ellee first to learn about who she was,  to pick up on the little things that I think work with her and what doesn’t,  and I think that I have that now. It was also very important for me NOT to spank Ellee the good old fashioned way just yet. This is all about getting into someone’s mind and building a character and building trust,  because the next spanking that she has coming will be the worst from me yet. It won’t be the hardest spanking she has ever had,  but if I play the game the way I intend to,  then it will seem as hard if her mind is in the right place. The preparation and the anticipation are going to be meaningful,  I plan to make sure of that,  right down to the smallest detail.

The caning that Ellee got at 5am on New Year’s Day is further evidence of that. She told me that the cane I was using on her was much worse that the last cane,  but do you think that was on purpose? That particular cane that I used on Ellee on New Year’s Eve at medium force is the same cane that her friend Alex is going to feel very soon. Perhaps it is something that Ellee should think of in preparation of the next event where she will get twelve of the best from her headmaster. The cane that will be used for that scene has only been used once before that I remember,  and I remember it clearly because of the sobbing that it induced from the recipient.

There are methods that I have used before with other people that I will use again in the next scene that we do. Ellee will find herself in the corner holding her skirt up showing her red bottom to the world,  but before the cane,  some things are going to happen. All Ellee will be able to do is stare at the wall with an open mouth and listen to me as her bottom burns. Ellee is a big part of what we are setting up for the third part of the scene,  but the magic wand is in my hand. My intent is to make this a memorable event for her.

We have discussed everything,  even the minutest details about what we are both wearing. Ellee is going to be a schoolgirl and she is going to wear the nylon panties that I bought for her as per my request,  she even told me they are the right size and fit perfectly so that makes me even more excited. I am going to be dressed as you see me in the pic below. The panties are important for this scene and there is a reason that I chose not to ask her to wear them for the Uncle scene. They have been purchased specifically for the schoolgirl scene and Ellee knows that. There is a thought that I have in my mind,  any time that Ellee selects those panties to wear from this day forward,  it will be with the hope that as she puts them on,  it will remind her of the scene that we did,  I have a feeling that it will.

I’m going to be seeing Ellee next month so this will be happening soon. Unfortunately I can’t give many details ahead of time because certain things are designed to catch her off guard. The only thing that I will say is that when Ellee goes over my knee her skirt will be coming straight up,  but the real spanking won’t begin until she hands me the item that will be lying on the floor on a cushion just inches from her nose. Now she only has to wonder how long I will spank her for before I ask her to hand me that item and how long she is going to have to look at it while she is getting spanked. Word has it that it is the stingiest item that I own. This spanking is going to smart,  that’s a guarantee!!

I’m not going to underplay the Uncle scene that we did,  that was a very special gift that Ellee gave to me and it is something that I will remember fondly. The next scene is something that I hope the pair of us will remember for a long time,  in fact I am very confident that it will be. In just six weeks there is going to be a naughty schoolgirl over her teacher’s knee for a really good spanking. The magic wand will come out as she is stood in the corner with a well spanked bottom on display awaiting the cane. I still have some planning to do!!

Because of the events of the last few weeks my enthusiasm has returned and my excitement level for the coming year is sky high. I turn 50 years old this year and I plan to make it the best year ever. Dare I say it,  but roleplay or not,  when I spank someone for a real reason it gets my adrenalin going. This year I will be focusing on this area with the girls who are serious about doing this with me,  and including Ellee I already have three of these set up for the year with different girls,  with many more to come I am sure.

So a big thank you to Ellee for providing me with such a wonderful memory,  and I sincerely hope that we make a few more this upcoming year. As much as I wanted to play with Ellee on that first night,  I’m even happier now that we didn’t. Ellee is a very special person and I am glad that I got to know who she was first, before we played.