Jessie’s Diary - Chapter 16 - Anniversary Week to remember

Jessie’s Diary Part 16: Anniversary Week to remember

Several weeks ago I reminded Mistress that it was almost a year since we had met to discuss Her invitation for me to become Her personal slave and I had of course accepted the incredible privilege. Neither of us could really believe a year had passed since that night – despite so much occurring in that time and some major life changing events happening it seemed like only yesterday that we sat in a bar discussing the terms of my slavery and Mistress’ requirements and expectations of a personal slave.

We decided we should mark the occasion with some celebrations that would reflect our year – so we decided to have a nice night way with food and nice hotel to reflect the nice evenings out together and also an epic dungeon session to recognise the love of sadism Mistress has.

Ghosts and Ghouls

Mistress has a love of the dark and macabre, She is slightly fascinated by death and such things.  I suggested that we spend a day and a night over in York – one of UK’s most lovely but also haunted cities.  I booked us a private Ghost tour and a nice boutique hotel for the night.  The ghost tour was excellent, covering some of York’s’ most ghoulish history dating back to the roman and the Vikings. Our guide was excellent and recounted stories of ghost sightings and tales of York’s most haunted buildings.  

We returned to our hotel where I was permitted to enjoy Mistress’ bath water after She had finished enjoying the bath I had drawn for Her.  After a usual massage for Mistress we retired for the night with no D/s play for the night – as there was to plenty of time for that to come ……

Epic Dungeon Session

One of the things that Mistress & I had discussed for a while was an extended session in the dungeon.  Mistress had reminded Herself how much She enjoyed having a full dungeon of equipment available to torture me with when we recently visited to apply my punishment for breaking one of Mistress’ rules.

We managed to book the Leeds Dungeon (which has very comfortable overnight accommodation for Mistress) for an overnight session between 6pm and 11am

Mistress had made it very clear that the session would be incredibly intense plus there were some new toys She was desperate to try out on me including new electrics toy and the infamous new whip.  I had purchased a new outfit for Mistress to wear for the evening and oh my She looked utterly fabulous when She walked into the room as I knelt awaiting Her

 

The session began with Mistress thoroughly enjoying doing my make-up – Mistress really enjoys making me over, She loves making me look fabulously slutty  - She enjoys it so much She even uses Her best make up on me – by the time She is finished I look almost unrecognisable lol.  Mistress then selected the most horrid silly maid outfit for me to wear with my stocking and suspenders (no knickers as She wanted full access to Her cock to abuse it fully. I was then instructed to wait kneeling with my head down in one of the dungeon rooms for Mistress

The session started with me fastened down on my back my arms restrained by my legs were not.  Mistress was very much all business.  As soon as I was secured down and helpless Mistress explained that tonight was going to be serious sadism and She was really looking forward to really hurting me – a lot.  I was reminded that the dungeon was well away from anywhere and no one would hear me screams – if and when I was allowed to scream.  I was instructed that I was not to speak at anytime without permission – indeed I was quickly advised talking wasn’t initially going to even be an option as layers of tape were fastened over my mouth and then I was blindfolded.

The first part of the session involved brutal torture of my nipples cock and balls and upper thighs.  Mistress tied rope around Her balls and strung it tightly to a hook in the ceiling. I was told to keep my legs apart at all times.  I am not entirely sure what implements were used on me during this session but am sure there were paddles, canes, crops to batter my exposed balls, brutally sharp pegs or clips of some type were fastened to my balls.  If I had been able Id have screamed like a bitch, but the tape kept it to a futile muffle.  I was repeatedly reminded to keep my legs apart and a whip or tawse was slammed within inches of my exposed strung up cock  - so close I could feel the air move.  “Next time it won’t miss bitch – keep them open!!!!!!!!”

Normally when Mistress is playing with me She is having a bit of a laugh – even when carrying out intense levels of sadism (ball nailing and stapling me into a mangina) She was giggling and laughing at my discomfort and being playful. However tonight it was pure full on scary sadistic bitch mode and I’ll be honest with you reader – I was crapping myself as to what the rest of the night held – we were about an hour in to a possible 17 hour and I was pretty sure I was never going to last anywhere near that long ……  Eventually I was left to lie alone, blindfolded with cock still strung up and brutal clamps in place and some vile adjustable clamps on my nipples. I made the mistake of wriggling to try and alleviate some cramp in my shoulder, rattling one of the chains restraining me – I was reminded by Mistress I was not permitted to move and any further annoying chain rattling would be severely punished

Sometime later I was released to serve Mistress some food and drinks and while Mistress relaxed I was knelt head down nose to the floor.

The next session had me fastened into a chair – totally restrained which my legs fastened apart.  I was soon completely hard despite knowing that significant pain was shortly to arrive – the combination of the restrictive bondage and Mistress kneeling close within inches in front of me looking totally amazing with a sadistic little smile on her amazing lips.  Mistress delicately adjusted the hem of my dress to totally expose my dripping erection and I was treated to very brief gentle stroke of Her cock – which just got it even harder.  Mistress walked over to the bench and brought back the brank new electrical wand kit we had recently purchased.  Mistress was smiling as I wriggled in the chair, the straps were unbelievable tight and Mistress met my eyes, smiled and said – “shall we see how long that can keep hard shall we?”  Now I have seen these wands used before and how they have been gently worked up people legs / chests etc. to build up the anticipation of the wand on the more delicate areas.  Tonight I was awarded no such luxury – the only build up was between the slightly less sensitive balls and the dripping head of Mistress cock.  I was left ungagged during this and I begged, screamed, tried desperately to breathe through the pain as the wand danced around the already battered cock now hanging limply between my legs.  “Do You really think begging me to stop is really likely to have any effect bitch?” Eventually after trying out all the different attachments the wand was disconnected and I momentarily relaxed thinking the ordeal was temporarily over.  I was wrong, very wrong.

Mistress selected a short thin cane from the stand next to me and went to work on my thighs close as possible to Her limp dangling cock.  The cane stinging insanely against my thigh …. “Please Mistress …” I begged “What – you want me to stop whipping your thigh – OK”  

A momentary moment of relief until Mistress roughly grabbed the head of Her limp cock, pulled it out and stretched it to the full and rested the tip of the cane against it – “Oh god now please!!!!!!!!!!!!” as the cane hit for the first time I saw stars – I have no idea how many strokes I received as I lost myself somewhere after the first.

I was left to recover and a few minutes later Mistress came in to release me and instruct me to have a shower as I was now covered in sweat from struggling against the restraints and Mistress’ saliva.  “Actually no – you are going to wall in your own mess tonight bitch – you don’t deserve a shower”

Instructed to go down stairs I was then locked into the cage beneath the bondage bench and left as Mistress relaxed upstairs in comfort.  I was covered in sweat and spit and lay on the cold hard floor and left to contemplate what I had got myself into.  I had no idea how long I had been in session, how long I would be in the cage.  The only thing that I knew for sure was that as some point I was going to be meeting Mistress’ new whip …….

I had researched this evil looking thing and new it was capable of significant damage.  I didn’t have long to wait to find out how much it was capable of as when Mistress returned to release me from the cage She had the whip with Her.

It was the first time Mistress had used it and I was the guinea pig as Mistress alternated between different techniques and firmness - talented Domme that She is, She soon had it nailed as I described the pain level of each stroke and how it felt.  Mistress was soon able to control the whip and apply it exactly it She wished.  I was proud of the flogging I withstood for Mistress and She was delighted with the outcome.  She was now in a more relaxed, but no less sadistic mood then earlier.  The whip does indeed do a fair amount of damage as seen below

I was allowed back upstairs and allowed to serve Mistress some refreshments and relax on the floor for a while and take in some much needed fluids and some nibbles to keep my strength up for the remainder of the night.  I ran Mistress a bath and gave her a massage afterwards

After a while though I was instructed to wait in the dungeon again.  The next treatment was a good old fashioned CP session with Mistress basically working through pretty much every flogger, cane, tawse and paddle in the dungeon.  She was pleased to work out which ones She liked best and which ones She wasn’t keen on.  “You’ve actually come in handy bitch – I never usually get the chance to do all this practicing”

After the CP session I again made Mistress some more refreshments and relaxed for a short time.  After a while though I was instructed to kneel on the floor nose the ground.  Mistress returned with some rope – and something I couldn’t see – “Hope You are clean bitch – You know the punishment if You aren’t”  The rope was then fastened to my collar and I guessed the next – an anal hook was inserted (this one had a double ball on it for extra “pleasure”  The rope was pulled tight ensuring the hook was pulled very deep inside me.

I was then lead down stairs and firmly fastened into the bondage wheel

“Night Night bitch – don’t think about making any noise and waking me up – you really don’t want to find out what happens if you do …….”

I had no idea what time it was, what time it was when Mistress planned to release me – all I knew was I couldn’t barely move other than fingers and toes – was going to be an interesting night – especially with my little metal friend making itself a royal pain in the arse already.

And with that I was left

Now one thing about Mistress you might not be aware is that She suffers from a sleep disorder than means She can sleep for a very long time – there was a worry that Mistress would leave me lie this for longer than She planned

Now I don’t know what time Mistress locked me into the wheel and I don’t know what time Mistress planned to release me, but I do know that by the ever so slightly sheepish grin on Mistress’ face when She came to release me it was somewhat later than She had planned and we (me) only had a bit of time to tidy up the carnage of the night before.  I had at times considered calling out to Mistress as it was clear I had been there for some time but thought better of it.

It was an incredible night and one that will be remembered for a long time to come …..

Yours  

Nigel / Jessie