Sissy Story With Task

Sissy Joan Story Of Her Task

So today’s essay is inspired by one of the worst days I have had at work in a very long time. Not that the day was stressful but more that is was one of the most mind-numbingly borings of all time.

Of course, there are worse things than being bored at your work but at the time that you are bored out of your mind, you can’t name any.

It was decided because the council had made a mess of the billing sent out last month that to comfort the shock of getting a letter saying you owed even more money I was to personally handwrite all the address labels instead of printing them out of the printer as I normally do.

I am sure this made a huge difference when they arrived on the doorstep.

 Sissy phone sex chat

Bdsm Phone sex chat


As I sent Mistress a text telling her of my day and how bored I was writing four hundred and fifty-six address labels she thought the best thing for me to do after such a rotten day was to write an essay on my experiences which was, as usual, the worst possible thing she could make me do.


The reason was I remarked that it reminded me of one of the very many tasks she has set me to do usually

involving writing lines and wearing panties but that is another story.

It was a truly rubbish day but of course, work is not the be-all and end-all of my life*

Live webcams

Find a Skype Dominatrix here

* Boring but true that ‘’ Be-all and the end-all” as the phrase comes from Shakespeare, from Macbeth specifically, when Macbeth used to the phrase basically to mean “All there is to it.” He was referring to killing King Duncan of Scotland, and he was essentially saying that if killing him the be-all and the end-all — if he could kill the king and have that be the end of it — it would be done. But because there could be consequences in the afterlife, there are more issues involved.

We tend to use end-all, be-all differently, as a phrase to describe the ultimate, the very best we can get, all we would need. I don’t why things like this come to mind but they do

sissy picture


As I was going through the tasks of writing these long tedious addresses on a too-small sticky address label my mind was as usual wandering.

I was thinking back to some of the tasks that Mistress had set for me over the last year and how they affected me both at the time and later.

The amount of time I have sat in my office and tried to juggle my time to get my work done properly and in on time and also to finish a punishment exercise set to a tough time deadline by Mistress would add up to quite some amount.

The one that instantly comes to mind was the time I had to do a whopping two thousand lines.

The lines were to read as follows. I am a naughty little tart please spank me, hard Mistress.

Writing this is bad enough and the embarrassment I felt having to print this out was really bad. I don’t think you know how humiliating it is till you have to write it. The words take on a stronger meaning as you have to print them out time and time again.

You think to yourself that you are a naughty little tart and this makes you feel so very much ashamed.

sissy assignment

What made it worse was I had to do this only during my work time and in my office.

I couldn’t just hide away in my own house away from everyone and at least be comfortable in my surroundings even though what I was forced to do was shameful.

Added to the abject humiliation was the fact that I had to wear my girlfriend’s wide leather belt which had to be on the show I could not cover it with a jersey or jacket and to make matters infinitely underneath my trousers I was squeezed into pink lacy frilly panties.

There were many conflicting emotions flying around my head at the time. If I am honest one of them was a pleasure as I knew that my actions would be pleasing Mistress and the fact that knowing I was being humiliated by her even though she was very far away would make her happy gave me some small crumbs of comfort.

There was very real fear. I was worried about being found out on several levels.

I had already had a few comments about the belt which make me cringe and want to hide under my desk but I was terrified that somehow it would be known that I was wearing panties.

The thought of someone either seeing a visible panty line or perhaps they would be peaking out over the top of my trousers.

I wouldn’t even want to begin to think of how bad that would be.

This, of course, was the entire intention of Mistress to both give me a humiliating and mundane task but to add spice to it by having a fear factor at the very same time.

Writing the lines themselves were bad enough. It takes a very long time to write even one line much longer than you would think*

sissy task


*One line takes approximately thirty seconds to write as they have to be printed and written neatly and tidily. There is no sloppy work accepted. So that means you can do two lines a minute which makes it non-stop you can do 120 in an hour. This, of course, is not easy to do and causes really bad writers to cramp.

As Mistress usually deals in the thousands when administering lines then before you know it you have spent 10 hours to do one thousand lines. This, of course, is bad enough but then when Mistress decides that you not only

have to rip them up but have to be filmed doing it for them it humiliates you.

The only incident that sticks out was on a beautiful summer’s day. I exchanged several very cordial texts with Mistress about what she was doing and what I intended to do on this glorious sunny afternoon. Of course, my plans were very abruptly cut short when again I was given five hundred lines for being cheeky.

Thinking I could be smart I wrote the lines as quickly as I could and had them finished by four o’clock giving me plenty of time to enjoy the rest of the afternoon in the warm weather.

Being a fool I sent a text message to Mistress to thank her for the punishment and tell her that I had finished it as ordered and I had emailed a picture to her as proof.

I remember the entire text I got back.

‘I am at Loch Lomond having a lovely day wish you were here but you are too busy ( Picture below)



This seemed a bit cryptic to me so I sent a text message back saying I wasn’t busy as I had finished the punishment that

she had given to me and was looking forward to spending a nice relaxing day sitting outside in the park.

Of course, I should have seen what was coming as the next text ordered me to write more lines one thousand saying’ I must not presume I won’t get punished just because it is the weekend’ this was bad enough but I was also ordered to print out in block capitals within the next thirty minutes the alphabet.

This may not sound too difficult you might think. The twist was that the alphabet had to be printed out backwards.*

Don’t ask me why but I could sense laughter in the wording of the text message even though there was none printed.

sissy assignments

This was everything that Mistress intended it to be. Annoying, time-consuming, mundane and very very boring. Exactly the last thing I wanted to do at the best of times never mind on such a beautiful day.


*This, of course, came back to haunt me and can be seen by my reaction in the video of me ripping up all the punishment lines I was ordered to write.

For some reason having to rip up the alphabet written backwards fifty times was much worse than ripping up any of the numerous one thousand lines.

I think it is for the reasons stated above that it was such a cruel punishment to give out and I felt so frustrated having to do it on such a nice day



Mistress, of course, knows all this and if it makes her happy then I am happy despite my deep shame.

I let her know how even through the tedium today I was thinking of her and how the work task was much like one she set me and how she seems to know how to mess with my mind.

That being said Mistress also seized on a throwaway text I sent about her not knowing every little thing that embarrasses me. So that being said we go onto


The things in a session that make me the most uncomfortable that Mistress may or may not know about but will now after reading this*


*This is almost Shakespearian in its context much like his play within a play. This is me writing an essay within an essay,

Probably the first and last time that anything I write will be compared to the Bard.

There is of course famously a short spanking scene in Shakespeare’s play ‘ The Taming of the shrew’ where a woman is taken over the knee and spanked. Spanking was called breeching in Shakespeare’s time.



These are the things I do not like during a session and things that would make it much more difficult for me to take.


Perhaps if Mistress wants I could print out some of these in bullet point form and bring it with me to the next session and put in the punishment book just in case Mistress wants to look at them for reference. However, I know Mistress that you are an expert and will already know a few of these but there is no harm in writing them down here.


Some have happened previously and some I am worried will now happen without warning not that I have let you into the secret of what upsets me the most.

Probably the first and last time that anything I write will be compared to the Bard.

There is of course famously a short spanking scene in Shakespeare’s play ‘ The Taming of the shrew’ where a woman is taken over the knee and spanked. Spanking was called breeching in Shakespeare’s time.


sissy tasks

These are the things I do not like during a session and things that would make it much more difficult for me to take.


Perhaps if Mistress wants I could print out some of these in bullet point form and bring it with me to the next session and put in the punishment book just in case Mistress wants to look at them for reference. However, I know Mistress that you are an expert and will already know a few of these but there is no harm in writing them down here.


Some have happened previously and some I am worried will now happen without warning not that I have let you into the secret of what upsets me the most.

The last time you did this was when I was over your knee in the middle of a hairbrush spanking I didn’t think it was a big deal but when I tried to say what I was wearing I found it so difficult to get the words out as I was so embarrassed.

I can’t describe how humiliated this makes me feel.

To have to tell you aloud in detail that I am dressed like a sissy or tarty woman is awful and I hate it.

To have to say words and phrases like strappy high heels and especially ‘my’ pink lacy panties make me squirm and to hear you laughing at my discomfort is even worse.

For me, the punishment is much worse when I am forced into women’s clothing.

I can truthfully say I have never had the urge to crossdress in my life and it does nothing for me and I would not contemplate doing it outside a session.

But during a session, it makes the pain of the punishment even worse as I am so humiliated being dressed up.

Sometimes I can block it out a little and that is why I purposely make myself wear things that I can feel on me and are unmistakably female like the big wide belt and tight skirt and small things like the watch and the straps on the high heels.

It makes me realise how I am dressed and stops me blocking it out and adds to my shame and your pleasure.

The last time you kept telling me to speak up and also to repeat some of the things I was wearing. You kept on saying to me that I was to describe in more detail the items of clothing that I had on. I even had to tell you what the watch I was wearing was like as well.

You know somehow exactly what words I find difficult to say.

I hate every single second of doing it which is strange as there is no physical punishment involved so you would think it would be easier for me to take.



Not knowing what is coming next


This usually only happens when I have been bent over the cage for punishment or I am lying on the bed.

I sometimes get a clue by listening out for the noise of the implement that is to be used being lifted

Usually, the sound of the cane is a giveaway but the straps and tawse make very little noise.

However not knowing what sort of a pain to expect and how wide across my bottom the pain will be felt is very much upsetting for me


The announcement of what is coming next


A contradiction slightly to the above but valid I feel.

To hear you announce both the implement and the number of strokes strikes fear and shame in equal measures.

This was done at its finest the time I had to write down all the punishments I was due and you spoke aloud the punishment that was to come then administered it.

Then you would walk over to the table and pick up a pen and score out the punishment then announce the next one and on and on.

This was hard to take physically and mentally for me and I did not enjoy it

slave task


Being made to fetch the implement that is used.


To be honest this again probably contradicts the previous one but it is true none the less.

Being ordered to bring a cane or strap to be used on me is at first exciting but then when I realise what is about to happen and my submission of being responsible for the item that is to be used on me kick in I feel really small.

Being made to totter in high heels into another room and then pick up a horrible implement that is going to be used to make me suffer is a most unpleasant experience.

I, of course, pick the harshest implement every time as I feel I must try and please you and push my boundaries every time I visit.

What has also made things worse is being ordered to kneel before you and present the implement to you with my head bowed.

This was made even worse during the last session when you sat down and put your feet on my back. Just when I thought it couldn’t be any more horrible I moved position as I said I was uncomfortable and you told me to get back in position as I didn’t have permission to move.

No, I do not like this one little bit and I am honestly very much humiliated by this indeed.



The noise of the implement before it is used.

You do this quite a lot and I don’t think you realise the effect it has on me. Maybe actually you do and that is why you do it.


To hear the swish of the cane as you do a few fresh air stroke genuinely frightens me a bit as well as humiliates me and sometimes I flinch even though it is nowhere near me.

To be made to watch you do this before I am bent over for the caning I think may make me weak at the knees and I would be most uncomfortable.

It is the same with the tapping of the strap against your leg and the hitting of the hairbrush into your palm it all adds to the suspense and the growing fear of what is about to happen which chases away any excitement of what is coming next and emphasises the actual reality which is the pain.

I will never get used to the pain as no matter how many times I have punished the first stroke of any implement always feels so very much more painful than I remembered it from the last occasion.

Having to ask for the punishment/beg for the last stroke

You may not remember this but it is burned in my memory. To start one of the first sessions I had with you I had to ask right at the beginning for you to punish me.

You made me ask for an over the knee hairbrush spanking and I had to ask you to do it without any fixed amount of strokes it was to be done till I was crying genuine tears and to your satisfaction that I was crying enough.

This was truly horrifying for me to have to do.

Also when I am being punished to have to ask for the last stroke and to beg for it is difficult for me to do.

I find it difficult through the pain and humiliation to have to beg for you to give me the last stroke as hard a possible


Being held down in position

Now, this if it is not the worse thing you do to do me for humiliation then I don’t know what is.

The worst thing about it is that it works in every single way that you punish me.

When I am over your knee for the hand spanking or hairbrush spanking at some point I start to struggle badly when the pain is getting too much. Much as I try hard to

obey you and take my punishment without complaint it is only natural for my instincts to try and move me away from the falling blows.

This is when you show that you are physically stronger than me by grasping me firmly around the waist and holding me tight as you spank even harder for my misbehaviour.

This so humiliates me knowing that despite all my protests I physically can’t stop you from holding me down. It makes the pain somehow seems worse.

This works just as well when I am over the cage being caned or especially being strapped.

I am left in no doubt about who is in charge as I can feel your arm on the small of my back holding me in position.

The worst one of the lot I think is a very painful strapping when you used your foot to press down on my back and then my head as I was laid down on the bed.

On the video, you looked magnificent and I looked so humiliated but not as much as I felt.


General scolding

It is no big secret about how I dislike this.

If the punishment was to be given out in silence I honestly think I could take it much easier.

But some of the things that you say to me as you are handing out the punishment make me feel so humiliated I just want to run out of the room and go and hide.

I can’t explain why I feel such shame as they are only words but I think it is a combination of things.

To be told why I am being punished and to be mocked for what I am wearing is awful.

This probably reaches its absolute zenith when you make a huge fuss of lowering the panties and baring the bottom but you, of course, know this already.

The tone of your voice is what does the damage. It can so very quickly chance from light and mocking to strict and severe.

I don’t like it when you sound cross with me it again does frighten me a little which I guess is the point especially when you come right close to my face to emphasise the point


The last overnight session one particular phrase got to me.

It was the next morning and I thought that I would just be getting dressed and going home as the previous night I had

been thrashed severely and I didn’t think that there was any more punishment left for me to take.

As usual, I never learned my lesson and you had other plans.

On inspecting my bottom you were most displeased. Despite my complaint that it was so very sore and tender and I was still unable to sit comfortably you were not happy that there were sufficient marks on my bottom.

It was the way you told me to follow you into the living room and you said very casually and without any fuss.

‘You don’t realise what is to come once I get you over my knee I am going to give you such a thrashing’

I didn’t, of course, realise what was to come and that thrashing which included an extra 40 of the black cane was the worst I have taken to date.


Corner time

This surprises me.

At first, I thought this was easy to handle. Being honest I thought it was both a bit of a waste of time and also it didn’t add anything to the session.

I could not be more wrong.

Once you put me in the corner in tears after a severe hairbrush spanking and with my panties at my ankles and my blazing red and exposed bottom on the show I realized how very difficult it was for me to endure this.

I find I am so ashamed that when the tears are stopping from the pain of the punishment I am starting to tear up and cry from the humiliation alone of being made to stand in the corner.

This is, of course, made so much worse by the continual commentary you give and the laughter I can hear coming from you.

Even writing this down I start to feel very uncomfortable and ashamed.

I can’t express in words how horrible and degrading I find corner time.

Funnily when I am ordered back to receive more punishment even though I know the pain is going to return in a way it is a bit of a relief.


I hope some of these things are of interest and can be of use to you Mistress making the next session more uncomfortable for me and add to the fun for you now you know some of my secrets and there are more I will disclose to you if you wish

Back to –UK Mistress

Check out our Uk Phone sex Page

If you want to check out our fetish cams page then click the link