Jessie’s Diary, Chapter 19 - Resetting the D/s – Punishment Time

Jessie’s Diary, Chapter 19 - Resetting the D/s – Punishment Time

Returning Home

So it had to come – getting back to normal life after the incredible high of the holiday with Mistress Sarah.  Before the holiday we both thought I would struggle the most – I joked about setting the world record for “sub-drop” after spending so long in the company of my Mistress.  Fellow devoted slaves will be all too aware of the down you can get after just spending 1 or 2 intense hours with your Mistress in session, never mind the best part of 2 weeks.

I had even requested if Mistress could visit in the week we got back as I thought I would be really struggling getting back into normal life and considerate as She always is with Her slaves She readily agreed to my request which reassured me the first week back might not be too painful (emotionally anyway lol).

Mistress was struggling too, adapting to life back home especially amid the terrible events occurring at the time (Mcr & London attacks) To help cheer Mistress up I suggested a trip to the shops for a bit of retail therapy and a nice lunch out.  It seemed to do the trick – Mistress really enjoyed the day out and a particularly enjoyable part of the day was purchasing new underwear and outfit for Jessie – Mistress had great fun selecting jewellery and clothing to make me look beautifully slutty – talking just loud enough for bystanders to hear Her say how lovely something would look on me – without overdoing the public humiliation element.

The first mistake

Returning home we were both excited to try on the outfit and this combined with me not having come for about 10 nights had me absolutely bursting out of the delicious thong and dripping with precum (no surprise there)

Thankfully Mistress took pity and told me She thought She could have me spunk within a minute – I was glancing at the time on the mobile I could see in the corner of my eye and lo and behold soon shot a huge load all over the floor before the phone ticked over to the next minute – I thought Mistress would be pleased with this – I was SO wrong ……..

“So which part of telling me you are about to come and never coming without permission is difficult for you to understand?”

Oh god I had got so caught up in pleasing Mistress by coming so quickly I had forgotten one of the absolute golden rules

“You’ll be punished for that and you are definitely not coming again for a long time. Now clean up your mess and don’t even think about asking me how you are meant to do it – I think it should be very clear!!”

Promptly dropping to my knees I carefully lapped up the large dollops of hot salty mess beside Mistress’ feet.

Mistress is not one to spoil a mood so nothing further was said that afternoon and we enjoyed chatting and taking some photos of me in my new clothing before She returned home for the evening.

The second Mistake

Several hours later while messaging Mistress about how much we had enjoyed the day and She thanked me again for treating Her (yes Mistresses are allowed to have manners and say please and thank you to slaves) a message that stopped me in my tracks appeared

“PS you’re due 2 punishments”

“Been checking your diary – no entries since April”

I was reminded of The Rules – I apologised profusely but apologies don’t count for anything as a slave – only actions and adherence to The Rules

Reflection

I spent hours that night trying to work out why I as a devoted slave who I think tries my hardest to please Mistress Sarah and enhance Her life in any way that I can could suddenly be breaking the very basic rules of our D/s contract.  The realisation hit me I had allowed myself to get drawn into becoming Mistress’ friend who is Her slave rather Mistress slave first and foremost who is also a friend.  I had got slightly too relaxed in our relationship and spending so much time together including the holiday had made this situation worse.  I wrote my thoughts down and Mistress wholeheartedly agreed and re-assuringly She admitted that She was also to blame for allowing this to happen from Her perspective.  She assured me things were going to change and change immediately back to slave first

Punishment 1

Shortly after I was at Mistress’ house for a few hours one evening helping Her out with some jobs as the night got slightly late Mistress asked if I wanted to stay the night rather than drive home late – it was a kind gesture and I gratefully accepted.  As I was making us some tea Mistress edged behind me in the kitchen and casually asked if I was feeling tired, walking head long into the trap, thinking Mistress was planning a late night of box set watching together I cheerfully replied I wasn’t

“Oh that’s good – go out to Asda and get me a couple of large pieces of raw ginger and get back here fast and when you do get Your clothes off, get Your collar out and kneel on the floor in the lounge – it’s a shame to make you wait til next week for your first punishment”

Oh crap – mentally I was totally unprepared for this turn of events and I could see that Mistress sensed it to – adding to Her excitement that I was knocked totally off my guard.

“Your punishment just got worse slave – what do you so when I give you an order?”

“Yes Mistress I belatedly responded”

After returning I knelt there for a long while hearing Mistress rummaged upstairs – “Hope you are keeping nice and still bitch!” – then two seconds later “I think we are struggling with the Yes Mistress tonight aren’t we – trust me I will be helping you with that shortly”

Soon Mistress was in the kitchen preparing and in very cheerful mood I could tell – this was always worrying – Mistress in a bad mood before administering a punishment is bad, but Mistress in a good mood is so much worse as the sadist in Her is about to be unleashed.

Soon enough we started and inevitably the ginger was inserted inside my arse and I waited for the heat to build – whilst it was stingy it wasn’t too bad and for me this was bad news and it just meant the rest of my punishment just got a little bit worse.

Mistress started to cane me reasonably hard for a while – “no need to count yet, I’m just warming you up this isn’t the start of your punishment by the way – oh god what am I thinking – see I’m being nice getting your arse warm for the punishment – I need to stop being nice to you don’t I?”

“So how many days did you miss with your journal?”

I calculated the days as Mistress toyed with the cane in Her hands

“46 Days Mistress”

“That’s a lot of days isn’t it”

“Yes Mistress”

“I think you know what’s coming don’t you?

WHACK – the cane struck hard on my slightly warm arse.

“That’s not number one by the way – that’s just me showing you what each one will feel like at least”

“Oh and don’t forget you can of course stop and leave at any time you wish……” An option I was desperate not to have to consider.

“We shall do 23, have little break then the last 23 – got that?”

“Yes Mistress”

“Good”

Somehow I got to 23 – how I am not sure as the cane bit deep into my burning ass cheeks again and again.  The break I thought I was getting was not what I thought – Mistress made me turn over and liberally caned my upper thighs “This isn’t punishment – this is just me having fun – so you know the difference”

The second 23 were then administered and I thought I was done for the night – I was wrong as over the next hour or so Mistress generally caned me – not as hard as the 46 strokes but hard enough all the same.

Punishment 1 was out the way but I was reminded I was only half way there

Waiting Game

For various unfortunate unforeseen reasons the night I was meant to receive punishment 2 was cancelled so the punishment was delayed by a week – the threat of it hanging over me plus by now I was well into week 3 of Mistress cum ban meant I was totally on edge in the days up to Mistress coming to visit. This wasn’t helped by Mistress sending me the occasional pic of Her looking amazing just to wind me up and drive me further into desperate chastity.  I also received a message telling me to forget the idea of getting any sleep that night.  Mistress making my mind spin endlessly wondering what was in store. True Domination is much more a mental process than a physical one, Mistress Sarah is very much aware of this and was exploiting my unease about what was to follow to the full – basically extending the punishment from hours to weeks in my mind.  It worked a treat by the time Mistress arrived at my apartment I was already mentally on my knees begging.

Punishment 2

Mistress arrived looking stunning in a short summer mini dress, hair newly done earlier in the day and towering in knee length high heeled boots – She looked about 6ft tall and I felt immediately about 1 foot tall in Her presence. “Get undressed and get your collar!!” Business mode right from walking in the door “Yes Mistress”

I was made to sit on the hardwood floor facing the wall as Mistress prepared something behind me on the sofa.  I was then handed a notebook with “I must obey Mistress’ rules in future” at the top.  “you’ll see where to stop – make sure its all neat and no mistakes or you’ll be doing it all again”  “Yes Mistress”

Soon enough my hand and fingers were cramping from the repetitive writing and it was making keeping the handwriting neat very challenging indeed – but after about half an hour it was done and I waited with total trepidation as Mistress inspected each and every page for mistakes or poor handwriting – thankfully it passed Her inspection.  I was then told to stand and Mistress approached with a large roll of duct tape which was repeatedly wrapped around my mouth and head until no more than the most muffled “hmmmppfff” could be heard.

I was tied to a column in the apartment and then brutally whipped with Mistress new leather whip – it doesn’t cut the flesh in the same way as Mistress’ evil plastic whip but it stings all the same – but no more than a tiny murmur escaped my sealed lips – Mistress only able to tell when She hit jackpot when my knees would try and give way beneath me.

A paddling followed to warm my arse up before being instructed to lie on the floor – moments of comedy followed as I desperately tried to ask if I was to lie face up or down – hmmpffing through the gag failed so did sign language, Mistress was totally non-plussed by my impromptu game of charades so in the end I lay first face up then face down and then raised my hands in a questioning gesture – Mistress cracked up at this – as ever giggles are never far away when we are together and Mistress laughed as She told me face up.

Mistress stroked Her cock and got it completely hard – it was already dripping in pre-cum and it only needed the slightest touch to have me totally on edge.

Next up for a lesson were my nipples as Mistress fixed on a wooden clothes hanger with the metal clamps and enjoyed pulling this repeatedly but not quite hard enough to pull it off entirely ……yet.  Mistress then made me lie immediately in front of Her as She relaxed on the sofa – then Her awesome heel was brutally rammed into Her dripping cock while She carried on tormenting my nipples before eventually pulling hard enough to make the clamps finally give up their evil grip on my shredded nipples.

A new game followed as I was made to stand on tip toes, hands tied behind my back against the wall as I had to hold a penny against the wall with my nose.  This was really hard after a while and I was soon shaking with the efforts in my calves – no one bothered to tell Mistress’ cock this was an issue though as Mistress pointed out the ridiculous amount of pre-cum that was now snaking down my apartment wall – try and explain that stain if you can lol !!!!!

Mistress was by now really enjoying tormenting Her cock – which hadn’t been touched for almost 4 weeks and I was mercilessly edged time and time again – I was really worried out going beyond the point of no return because it was not easy to communicate to Mistress as I couldn’t speak and it was difficult to tell the difference between “mmmpppfff mmmuuummppff mmmppff” (oh god Mistress that feels amazing) and “mmmpppfff mmmuuummppff mmmppff” (oh god Mistress please I’m getting close Mistress”.  An accidental orgasm at this point would have been unimaginably bad – possibly the worse thing I could have ever done – but with Mistress absolutely loving my torment it carried on and on.  After a while enjoying Herself immensely Mistress instructed me onto my Knees with my arse in the air towards Her – (it’s a very lovely sight honest lol) “mpf mmmttfss” (Yes Mistress).

One of my favourite toys was inserted – the electrastim maxi butt plug – its quite wide so takes a bit of a shove but once it produces the most amazing sensations – it basically fucks you senseless on certain settings and has led to some of the most unforgettable orgasms I’ve been allowed by Mistress Sarah.  I thought I was really going to be in trouble now as the risk of me cumming with this in went up about 1000%.

Soon enough after enjoying the sight of me writhing and bucking with pleasure as the plug fucked me mercilessly Mistress began to stroke Her cock – within seconds I was screaming into the gag to tell Her I was close to cumming and I was truly worried about the reaction when I would shortly cum as I passed the point of no return – for some unknown reason Mistress kept up the incredibly pleasurable stroking and I launching into the strongest orgasm I can remember for some time – almost 4 weeks of no touching came to an end and I almost collapsed from the effort as the last bit of cum came out.

And so to “bed”

After running Mistress a bath and making a late night snack – a deliciously naughty bowl of cheesy chips for Mistress I was instructed to get the usual bag of restraints and I was about to find out what Mistress had in store for my bondage for the night.  It also felt slightly earlier than normal so I knew a long night was ahead of me

The enhancement tonight was Mistress’ large anal hook – I’ve had this inserted at night before but not for a while and thus time it was fastened incredibly tight to my neck but also to my ankle restraints – my legs were pulled up quite tight so I couldn’t stretch them out and my wrists fastened in their usual restraints which were then tied to a handy column in the apartment.  Now this position is not too bad for say maybe up to an hour – but trust me after 5 or 6 it really begins to work its magic – your legs begin to cramp from not being able to stretch them, you can’t put your lead on the floor (I am never allowed a pillow) without it pulling the hook even deeper inside you.  It was a long uncomfortable night.  Worryingly though Mistress advised me the morning after being released after 12 hours that the hook was not going to remain forgotten this time

Mistress advised me that I am now no longer on punishment status and I can again concentrate fully on adhering to the rules and serving my Mistress as slave first and friend second.  A Lesson has been learnt.

Your Nigel / Jessie

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