Sissy Joan Spanking Essay

Sissy Joan Spanking Essay


Five thousand word essay on Hairbrush Spankings broken into three parts as the word count is so very much longer than usual this is done as to give Mistress Vonn and anyone else unfortunate enough to have to read my ramblings a bit of a break and for them to know how much longer they have to suffer.

Great opening lines from novels*


In my younger and more vulnerable years, my father gave me some advice that I’ve been turning over in my mind ever since. – F. Scott Fitzgerald, The Great Gatsby


It is a truth universally acknowledged that a single man in possession of a good fortune must be in want of a wife. – Jane Austen, Pride and Prejudice


Someone must have slandered Josef K., for one morning, without having done anything truly wrong, he was arrested. —Franz Kafka, The Trial


As Gregor Samsa awoke one morning from uneasy dreams he found himself transformed in his bed into a gigantic insect. Franz Kafka**, Metapmorphosis


It was the best of times, it was the worst of times, it was the age of wisdom, it was the age of foolishness, it was the epoch of belief, it was the epoch of incredulity, it was the season of Light, it was the season of Darkness, it was the spring of hope, it was the winter of despair. – Charles Dickens, A Tale of Two Cities


I am sure you will agree on memorable first lines that make you want to read more.

However, as I only have a miserable English O’Grade  I am afraid my opening line does not compare well to the others though however, it is quite unusual.


‘I was fully aware of the little pink panties and wide belt I was wearing as I nervously searched for a hairbrush that would be used to spank me’’


*Well seeing as I have to do five thousand words in this essay this is as near to a novel as I will ever write.

** Franz Kafka clearly a man with a strange and disturbing imagination but after reading some of my daydreams in this essay who am I to talk?




To start this essay off I would like to give a piece of free advice that should come in useful to any of Mistress Vonn’s subs who happen to be reading. Do not ever text Mistress and tell her that you are bored. I was stupid enough to do this and this afternoon I got the reply back to do this essay to keep me occupied. Not the usual one or two thousand words essay but a keyboard-busting five-thousand-word essay. Oh and as if this wasn’t enough I have to wear pink panties while doing it. It honestly doubles the humiliation for me which of course doubles the pleasure for Mistress which of course means everyone is happy* which is good.


*Eh except of course me





The text message caused all the trouble and one mans worried as he searches for a hairbrush.


The subject of this monster* essay is to be I will remind you again a whopping five (that is not a misprint) five thousand words on the subject of hairbrush spanking, not the usual thousand

For my first session part of the punishment was that before I visited Mistress I was to go into a shop and buy a large flat-backed paddle-style hairbrush for her.

Again this is where the mind games came into place as I wandered nervously around Boots looking for a hairbrush.

Normally I am a rational person and relaxed and laid back.

I am very interested in science, astronomy, philosophy, the arts, and ancient history. Whilst my education was not good I think I can humbly say I can hold a decent conversation on a number of subjects with much more highly educated people than myself and not sound out of place. However, when I am under Mistress’s control this all goes out the window and I turn into a bumbling fool and I start to become a neurotic mess and walking disaster area.

I start to think that all the shop workers in the shop know I am in for a hairbrush to be used in a spanking session and even daydream of worse scenarios**

The worst part was taking the hairbrush off the footery little hook and checking out if the back of it was wide and flat enough for its intended use.

The whole procedure put me firmly in my place and showed yet again how Mistress with one tiny little text message had me totally in her control and doing things that caused me great humiliation and her great pleasure.


Carrying the hairbrush in my bag even causes me to panic. Firstly I have to check it is still there and has not somehow fallen out. I can imagine the reaction Mistress would have if I somehow came back no bringing the hairbrush she gave me a direct order to bring. Does not bear thinking about though a different spelling of the word bear would come into the equation*

A packed Glasgow tour bus goes past me as I am checking out the hairbrush and I start to daydream about what the tour guide is saying over the microphone to the tourists on board as he passes by**

All this is getting into a high state of anxiety and yet Mistress has again I will remind you not actually said a single word to me. It is all the power of suggestion and all-cause by one little phone text message and the overwhelming power of Mistress’s personality over me.

A walking shambles I head for the subway station knowing that in fifteen minutes I will be outside Mistress premises and my wait for punishment will be over.



* A little cryptic puzzle to break up the essay. Rearrange the following words to make up the popular phrase Mistress would use after I disobeyed one of her orders.

‘’Bare the on extra cane bottom black 40 the of ’’

** I can hear the voice over the loudspeakers on the bus as it passes

 Tour Guide ‘If you look to your left you will see the City Chambers building this fine piece of architecture was finished in eighteen eighty-eight and serves as the headquarters of the local council. On your right is a man that has just purchased a hairbrush and is heading to his Mistress where he will be dressed in a skirt high heels and panties and will be spanked and caned. For those of you visiting from France, I will repeat

Sur votre droite est un homme qui a juste acheté un hairbrush et se dirige à sa maîtresse où il sera habillé dans de hauts talons et des culottes d’une jupe et donné une fessée et caned.’

At this point, the passengers all point and laugh and flashbulbs go off some even take some video footage to upload to youtube.

 I am sitting on the subway and I can’t take my mind off what is to happen.

All the scenarios running through my head drown out the loud noise of the carriages thundering through the tunnels.

I take the hairbrush out of the bag again hiding it as much from view as I can. I turn it over in my hand and feel how wide the back of it is again.

I take the price label off it* and make sure it is perfect for Mistress Vonn to use on me as only the best will do for her**.

I start to imagine how she will look holding it.

I hope that somehow she will not hit me as hard as she usually does with it and I will be able to talk my way out of the spanking or at least lessen the impact**

So engrossed in these though that I almost miss my stop and have to jump through the rapidly closing subway doors. This of course starts the other real fear I have visiting Mistress that I will get in some sort of accident that involves a medical person treating me and finding out I have frilly panties on underneath my trousers.

Yes Mistress Vonn truly has me a neurotic walking wreck of a man before the session has even begun


*£8.99 adding considerable financial insult to my wallet as the later bottom injury it will cause

** I honestly believe this and not an attempt to butter Mistress Vonn up as last time I tried to do that I ended up getting caned and electric shocked at the same time.

**Yes I honestly still after all these visits think I can talk Mistress Vonn out of giving me severe punishment. I never learn from my mistakes and Mistress Vonn makes sure I am punished for them.




The actual hairbrush spanking and what thoughts are happing during it


The words hairbrush spanking both excites and scares me at the same time.

Excited as I know I will be, after several long weeks of email and text control with lots of punishment essays like this one and lines*, under the physical control of Mistress Vonn and will receive the severe punishment that she thinks is necessary for me.

Mistress in my opinion never looks more dominant when she is sitting comfortably and smiling beckoning me to come towards her with one hand and ominously tapping the hairbrush across the top of her lap.

The hairbrush in Mistress’s hands is a fearsome weapon and has caused me serious pain on numerous occasions and I hope for my sake on many many more occasions as I am in need of punishment from Mistress to keep me in my place and to remind me who is in charge and to stop me from being disrespectful.

Every session is very different but usually, I find as a warm-up an over-the-knee hairbrush spanking is how the session starts.

Now as I find Mistress is upping my training the severity of the hairbrush spanking is extreme and for the last three visits, I have been spanked to tears by Mistress which lets me know that the rest of the session is going to be very painful indeed if this is what the so-called warm-up does to me.


* No doubt to be ripped up on the front of and to the great delight of Mistress Vonn



I am ordered to come over to Mistress to start my punishment. Her voice is so severe and I forget how it adds a whole new dimension to my domination. She can control me by just a few spoken words and I am powerless to resist.

I am frightened but as usual, stunned by Mistress Vonn’s appearance as she sits down on the couch. I don’t forget of course but she her again reminds me of how beautiful and stunning she is. Honestly, I am blown away with how fantastic Mistress looks and I keep on having to remind myself how lucky I am to be not only in her presence but to be allowed to serve her.

To know I am going to have to bend over her beautiful and amazing legs both frightens and excites me in equal measure. The only thing I don’t like is I am tottering over in strappy high heels and dressed like a sissy. Of course, Mistress now knows exactly how much this humiliates me and before she starts the spanking I have to tell her in exact detail every girly item of clothing I am wearing including material and color and if I miss anything out it is extra punishment.

You have no idea how ashamed I am having to say out loud to Mistress Vonn the following. I am dressed in a lycra Secretary skirt which reaches just above the knee with 4-inch wide leather belt around my waist and a white blouse. I have high heels shoes with ankle straps I am wearing a bra and pink lace French Knickers on underneath with black hold-up stockings. I also have a little gold watch on my wrist.

Please Mistress put me over your knee like the naughty little girl I am and spank my bare bottom till I am crying as I am such a little tart and deserve to be punished.

They are no words to begin to tell you how humiliated this makes me feel I want the ground to open up and swallow me.

The hairbrush that innocently was designed to comb and brush hair now has been transformed in Mistress Vonn’s hands into the device for administering punishment that will literally make a grown man cry*

I would say the hairbrush is approx 4 inches wide by 7 inches long and this is more than enough to cause serious pain and discomfort.


*And humiliatingly enough there are videos of this as proof that Mistress Vonn keeps threatening** to put up on the website and I hope she never ever does.

** Mistress Vonn does not make threats in regard to punishments instead she makes promises which she always keeps.


My bottom is already sore from the hand spanking that precedes the use of the hairbrush. My skirt and panties have long been pulled up/lowered respectively and my bare bottom is awaiting the onslaught to come.

The first stroke of the hairbrush always takes me totally by surprise.

I think the reasons are twofold for this. Unlike the cane, strap and tawse there is no noise as it makes it way down to the target area and secondly I always (and I don’t know why as I get punished with it often enough) underestimate how much the hairbrush hurts.

I think you really have to experience this for yourself* to understand how an innocent piece of plastic can cause so much pain.

Also, I feel that the width of the brush is much wider than anything that Mistress Vonn uses on me** and this causes the pain to be over a larger area of an already sore bottom.

In one memorable session, I was given tasks to complete which I basically had no chance with***. Every time I failed one of these impossible tasks I was made to write down my extra punishment. It ends up with me handing over a list to Mistress which she then read out to my great shame.

Over ninety of the hairbrush to the bare bottom is fearsome enough but then twenty to the thighs was added. By the time the punishment was over both my bottom and thighs were redrawn as I was also given extra strokes for cheek and throwing a tantrum when I lost count.

I notice thanks to Mistress Vonn’s skill and expertise and wicked sense of humor every aspect of the sessions is different and is constantly evolving.

From watching the various video clips of my hairbrush spankings I can help realize that the over-the-knee section of the punishment is much harsher than I used to receive.

Don’t get me wrong all the previous hairbrush spanking really hurt and I always at the end did a version of Riverdance****. But the current hairbrush spankings are just so ferocious and I am always in tears at the end of them.



*If you are reading this in the protected area of the website you must have already seassioned with Mistress Vonn to get the password so you know exactly what I am talking about which I guess makes this footnote irrelevant except for padding out the essay!

** Except of course from recent sessions as now what is used is my girlfriend’s wide belt which Mistress Vonn not only insists I wear with my trousers on the way to the session but also uses on my bottom. At two and a half inches wide and a quarter-inch thick it is heavy and very painful when Mistress Vonn uses it to spank me with. Not to mention the severe mind games it causes when not only when Mistress next orders me to wear it at home but especially anytime my girlfriend wears it with her clothes. Yet another implement to add to the long list of things that I have been spanked to tears with.

*** For instance write eighty words about horses in one minute and as if that wasn’t impossible enough Mistress Vonn would point to words I had just written and ask me what they were.

**** After having a severe over-the-knee spanking I will jump up and then dancing about the room with my back held straight except of course my hands are not at my sides like the Irish dancers they are furiously rubbing my blistered and sore bottom. Then again sometimes Mistress Vonn doesn’t even allow me to do that which is really strict and cruel of her.


Now however the last four hairbrush spankings I have been lucky enough to get have genuinely made me cry* and the last one, in particular, had me howling and pleading for Mistress Vonn to stop which of course made her spank longer and harder till I stopped complaining.

At one stage Mistress actually had me laughing through the tears of a ferocious spanking. It was the morning after the overnight session and Mistress Vonn inspected my bottom as she made me change from the nightdress I was made to sleep in into a little black dress.

Again I foolishly thought the session was going to draw to a mild conclusion as I thought Mistress Vonn would be tired after the exertions of the severe thrashing she had given me the night before.

Obviously, I have not learned anything and Mistress Vonn was very unhappy with the lack of marks on my bottom**

Again I was in a familiar place bent over Mistress Vonn’s knee with my bottom bared for one hundred of the hairbrush. I only lasted about six strokes before I was in a lot of discomfort the next six had tears in my eyes. I was struggling to count aloud the strokes and this made Mistress Vonn annoyed so she started to spank harder and very fast. In fact, so fast I could not shout out the number of the strokes fast enough so thought the pain I tried to remember how many I had.

Of course, I always got the number wrong so Mistress would start again.

The more I asked her what spanks counted and what didn’t the more she laughed and said it was my problem to find that out not hers

Time and time again this same thing would happen a sort of spanking version of the film Groundhog Day if you like with Mistress laughing and starting again every single time and my losing count again every single time.

It got to the stage that despite being in floods of tears I shouted out that we would be here all day and I had a train to catch so could we just agree to a number and stick to it.

This caused me to start laughing for some reason and Mistress Vonn started to laugh as well then absolutely thrash my poor bottom into the middle of next week for my cheek.***


*On one occasion Mistress Vonn asked me if I was crying like a baby in the middle of a blistering hairbrush spanking and I stupidly replied I wasn’t I just had something in my eye. This sarcasm went down as well as expected and I was howling not crying by the time Mistress Vonn had finished with me.

** I honestly don’t know why the marks and wheals on my sore bottom looked like a hundred empty noughts and crosses games written by a pink pen on red blistered paper.

*** The first bottom to travel in time hee hee.




Looking back at the spanking and the hairbrush part in particular.


The whole session is deep in my memory and will not fade through time any time soon* I try and playback every aspect of the session in my mind and try and find ways of making my part in it better for Mistress Vonn and try and remember what I did that pleased her as I want to be the best possible sub I can for her and give her as much enjoyment as I can.

I find however that I keep looking back to the hairbrush part of the session more than the others. Don’t get me wrong I enjoy every nanosecond I am in Mistress Vonn’s company but the knee part of the session seems to be the one I enjoy the most.

I think I finally know the reason for this.

During the caning and the strapping sections of the punishment, I am usually bent over the cage or chair or lying flat on the bed**

This I love but it does keep me at a distance from Mistress Vonn and makes the punishments a little anonymous at times not that I am complaining in any way shape or form about this. Of course, Mistress Vonn is always thinking about new ways to change the session and during the last one, she had a full placed mirror in front of me so I could see her administering the strappings and canings, and also she could check to see I was smiling as I get extra punishment if I do not smile during the sessions even when I am being whipped to tears.



*The physical marks are starting to last longer as well as Mistress Vonn ups my training to take more severe punishment. After three weeks I still had six cane marks on each cheek and three lovely ones on my right thigh. The bruises from the hairbrush spanking usually go within a week to ten days but they hurt just as much.

** This is where the infamous incident occurred where Mistress Vonn thrashed me so hard the came snapped. It was only a flimsy one Mistress Vonn warned me after she did it. It could have fooled me and my bleeding bottom.


I think what makes the hairbrush spanking so memorable for me is I feel totally dominated and under Mistress Vonn’s control and more so than any of the other physical punishments she administers to me. When I am over her knee there is no escape and I have no choice but to submit to my superior* and take the punishment that is to come.

Again I am grateful to Mistress Vonn for allowing me to serve her and will happily accept any punishment she feels fit to give and it is a great honor to do so but over the knee spanking with the hairbrush is the one that I feel is the best that she gives.

The more I complain and squirm across her lap the more Mistress Vonn seems to laugh. The movement is very restricted for a few reasons.

The wide belt I am made to wear keeps the top of the skirt and blouse tight across my waist so I can move much there. My hands have to be placed in front of me and my head must be kept down so there is no movement in the top half of my body either. My panties are pulled down just enough to restrict the movement in my thighs and the straps on my heels give me little movement in my feet.

If this is not bad enough I have noticed as the spanking starts to really hurt I try to move away from the blows and Mistress Vonn noticing this will then pull my waist in and hold me down tightly with her left arms and spanking even harder. This of course makes it almost impossible to move as Mistress Vonn is I am sure physically stronger than me and adds to my abject humiliation. There is no escape from Mistress Vonn on these occasions she is always one step ahead of me and will notice any of my little pathetic attempts to lessen the pain of the punishment.

What I have noticed especially both at the time and watching the videos is that Mistress Vonn is an expert at body language. Not matter how hard I try to disguise it if  I flinch more than usual when I am spanked on a particular tender spot of my bottom not only does Mistress Vonn pick up on this right away she also purposely plays on this and will administer rapid and harder spanks or strokes to the exact same spot knowing it is really hurting.

This is domination and strictness at its very best and how I adore Mistress Vonn for allowing me to be a part of this.

The bruises the hairbrush leave also show what a good aim Mistress has. With the cane marks they are evenly distributed all over my bottom and thighs. The hairbrush marks are also all over my bottom but the deepest and angriest bruises are at the sit spot where my bottom and thighs touch and I feel it every time I sit down**

I have strange feelings that I didn’t know existed when I am over Mistress Vonn’s knee being spanked. I want to be made to knee in front of her and kiss her feet and have Mistress use me as a footstool while she laughs***

The hairbrush spanking part of the session if you like also sets the table and sets the standard of the punishment to come. Of course, every session I have had with Mistress Vonn has been totally unique and a one-off and has been a day to remember but as my training is stepped up the opening spanking is getting harder and harder.

At the risk of asking for trouble, I honestly don’t know how Mistress Vonn can continue to make the hairbrush spanking any more painful. My strong suspicion is that on previous evidence she will.

One way is I suppose no warm-up spanking with her hand. This of course is no laughing matter as a hand spanking from Mistress Vonn in itself is very painful.

But the thought of an immediate hairbrush spanking over the knee especially on the bare and cold bottom is something that I would not like one little bit.

Also, I am always remembering one of Mistress Vonn’s mottos she said to me**** and waiting when I first arrive at the door to be dragged by the ear and put over her knee while still in my male clothes. The thought of that happening as soon as I arrive is always in my mind and I would be really humiliated if Mistress ever did this. I just hope this does not give her any ideas even though mine are nowhere near the standard of hers when it comes to new ways to punish me physically and mentally humiliate me at the same time.


*One of the things I had to write out 300 times for Mistress only to have to rip it up and have it filmed for her further amusement that was really unfair and I am still unhappy at having to do that a couple of months later which I suppose shows again Mistress Vonn is way ahead of me knowing what exactly works to make me uncomfortable

** What makes these sit spot bruises worse is the panties I am forced to wear occasionally as part of my long-distance control never even cover this lower part of my bottom.

At work, I sit in a quite uncomfortable chair so only have my light trousers as protection from the wood with the lace panties too high up to afford me any padding. I so hate being made to wear panties to work at any time I really hate it but after a session, there is considerable physical pain added to my mental anguish.

*** Which actually happened during the last session and when I said I was comfortable Mistress Vonn made sure I was kneeling in a way that made me uncomfortable and then put her feet back on top of me. Yet again I never learn my lesson and keep my mouth shut.

**** Expect the unexpected from your Mistress.


So this is my magnum opus for Mistress Vonn. Five thousand words on a subject that excites and yet really scares me at the same time. For someone that is now used to at least 50 minimum of the black cane on an already sore and marked bottom, I should not be so scared of a hairbrush spanking but I am.

It is the most humiliating of all the punishments that Mistress Vonn is kind enough to administer to me. Looking at the videos I seem to cry and struggle during an over-the-knee spanking more than I do while getting any other punishment.

It emphasizes Mistress Vonn’s superiority over me and makes me feel weak and small which I am sure pleases Mistress Vonn no end.

It is to quote the phrase from Charles Dickens at the start of this essay ‘The best of punishments it is the worst of punishments’