Jessie’s Diary - Chapter 18 - The Holiday

Jessie’s Diary Part 18: The Holiday

Firstly an apology right from the start – this blog may contain slight overuse of the following words – Incredible, amazing, stunning and unforgettable – sorry but that’s just unavoidable.

So many of you twitter folks may remember a very long time ago (August last year) Mistress Sarah kindly accepted my offer to share some time with her away on holiday together as friend and Mistress / slave.  As it turned out we both really loved the idea of Mexico (a place Mistress has longed to visit).  We also noticed that weather-wise and timing it also coincided with Mistress’ May Birthday.  After a quick search I found something I thought looked the suitable place for a Mistress to relax and excitedly we sat in Mistress’ bedroom during one of my visits and eagerly paid the deposit.

August to May is a very long time but it gave time for the excitement to build and gave us both something really positive to focus on during some challenging times for us both.

Finally though the day arrived and I set off the day before to drive to Manchester to have my full body waxing (I do mean FULL – an interesting experience in itself to be honest holding Mistress’ cock out tight so a girl in her early 20’s could pour soothing warm wax all over it before going to work with the wax strips) for a person of my personal disposition and sexual kinks it took a tremendous amount of self-control not to get “excited” during this particular experience. As Mistress has said more than once – “My slut is always hard”.  For once somehow I managed to keep the fires from burning too brightly down there.

I arrived at Mistress’ house and after some last minute shopping I was instructed to assist with packing Mistress’ suitcase.  An enormous pile of clothing was deposited on the sofa with me scratching my head wear to start.  Eventually after carefully arranging Mistress’ clothing into piles and neatly folding everything (OCD me?) Mistress looked on in puzzled bemusement at my somewhat regimented approach to packing but eventually the case was full but everything was ready to go.  

The Flight

Some of you may know that Mistress isn’t overly keen on flying – understatement of the year award I think.  This was also Mistress’ first long haul flight as She had avoided them previously due to this fear.

So unsurprisingly we found ourselves in one of the bars at the airport for a quick drink that turned into 5 and a quick shot downed as the plane was closing boarding.  We hopped on one the last to avoid being on the plane any longer than necessary.  The flight was somewhat eventful due to a combination of 1. Mistress & I being somewhat tipsy; 2. Mistress being found with Her ecig in Her hands 3. Someone complaining about Mistress smoking the ecig 4. A very patronising flight attendant; 5. A rather confusing conversation about whether Mistress was diabetic or not (She isn’t thankfully)

Thankfully after a few interesting conversations with flight crew all was settled and the second half of the flight passed off without incident and we landing in Mexico tired but excited.

The Hotel

The hotel was amazing, lovely rooms, excellent food but the most incredible thing was the genuine service from the hotel staff – I have never felt such genuine effort make everything perfect for the guests.  When you are a slave who spends a considerable amount of time working out how best to please and delight your Mistress having an army of staff in the hotel who will do anything to help is a real bonus.

Our room was lovely with a four poster king size (and then some) bed.  The four poster was to prove very useful for Mistress as the holiday progressed – more later

Mistress / slave on tour

We had a brief discussion early on regarding ground rules about how the D/s element would work on holiday (what should I call Mistress in public etc.) We quickly settled into a routine which worked – clearly Mistress was on holiday and was not there to be a Domme 24/7 but equally She was not going to be getting drinks from the bar when She had a slave on hand either.

Settling In

Our first couple of days were spent chilling round the pool working through the cocktail menu, exploring the beach and relaxing.  We had an amazing massage together on a pagoda on the beach which was just stunning with the waves gently crashing a few feet away and the massage itself was one of the best I have ever had – I had to accept that it was even better than the massages I pride on giving Mistress during our evenings together.

Mummy why is that man wearing a fleece?

After a few days settling in we began to develop some daily routines as most folks do on holiday.  One of our routines was the morning sunbed selection and coffee / fruit run.  Sadly despite many notices and comments around the hotel requesting patrons to avoid bagging sunbeds for later in the day it was evident that to get a desirable sun worshipping berth near the swim up bar that we frequented on a very regular basis it was necessary to follow the crowd and get up early-ish and reserve a couple of beds for later in the day.  I also combined this with a trip to the main hotel restaurant to collect a selection of melon for Mistress to enjoy in Her bed when she awoke.  

This might sound somewhat trivial but it becomes slightly more challenge proposition when you have a slave collar padlocked around your neck which was generally only removed once Mistress awoke and got out of bed later in the morning.  Mistress was not about to change Her routine and certainly not be disturbed to remove the collar early so I had to come up with a solution to the problem – hence the sight of me regularly wandering around the complex wearing my lovely fetching red fleece fully zipped right up to top to cover the collar.  Unsurprisingly there were very few other folks strolling round the complex or going to breakfast in a fleece and I looked very special meandering the resort in my winter gear in 28 degrees heat. A very strong look for sure.

Careful You’ll have someone’s eye out with that

Mistress got very excited at discovering that a little way along the beach from our hotel was a nudist hotel and almost immediately we were off along the beach in search of it. When we arrived we strolled along the public beach in front of the hotel and then made our way into the hotel to see if we could arrange a day pass or similar as we were aware some places do allow this sort of access – sadly before too long we were greeted by the hotel security team who advised such an option was not available to buy and asked us to exit the world of openly dangly willies not so dangly boobs – ah well

Endless Edging

It had been sometime since Mistress had allowed me to cum before the holiday and I arrived in Mexico in a state of almost total horniness.  The combination of the prospect of spending lots of time with Mistress in a series of tiny bikinis and the little hints of things that Mistress had planned for the holiday had me feeling incredibly desperate for some form of release.  This made Mistress very happy and added to Her plans for putting off the moment I might be permitted to cum

One of our routines on our regular overnight sessions is for me to be placed in tight bondage during the night for me to sleep.  Bondage seriously excites me and always has me in a highly excitable state.  One of the bonus’ of the room was the simply enormous four poster bed in the suite.  Rather than the usual floor I was permitted on most evening to sleep in Mistress’ bed – however it wasn’t so simple.  One of the benefits of the bed was that Mistress could tie me completely helplessly to the two side posts hand and foot.  Placed in this predicament I was inevitably incredibly aroused and Mistress took full advantage of my horniness and helplessness by endlessly tormenting Her totally erect cock.  The height of this teasing was captured on video as She gave me a foot job lasting what felt like hours as we watched a film one evening, Mistress edging me mercilessly time and time again with her amazing, perfect feet and occasionally Her immaculate fingers.  Eventually She decided enough was enough and I was left desperate and horny for hours as I tried to sleep bound hand and foot with a hardon that would not subside. Total heaven and hell all rolled up into one.   

A Swell time at sea

After a few days chilling we went on our first excursion – snorkelling on the nearby reef.  I had snorkelled several times and done some diving in the area previously but it was Mistress’ first time and She was very excited to give it a try.

The conditions were not perfect however as there was a quite large swell in the sea and we were in quite a smell but very fast boat to get to the reef.  The snorkelling itself was excellent – seeing a turtle, baby stingrays, lobsters as well as the usual array of beautiful tropical fish.  However after a while in the water with the large swell (about 7-8m) both Mistress and I started to feel a tad queasy in the water.  Mistress is somewhat travel sick and was beginning to go a bit green but thankfully we arrived back at the dive boat and we would soon be heading back to shore……… or so we thought.  Unfortunately the boat we both thought was ours wasn’t and we were both shocked when we saw our boat was still some distance away – oh dear.  At this point Mistress’ resolve finally cracked and so did Her stomach and soon the Caribbean Sea was graced with the presence of Mistress’ stomach contents from the morning which due to the particular cocktail that we had enjoyed earlier was a delicious vibrant pink colour.

I watched in horror as the “vomit slick” trailed off behind us and in the direction of the two other guests who were snorkelling with us and as they had their faces down in the water were sadly totally unaware as they both plunged directly through Mistress’ recently semi digested breakfast – oooops

Thankfully we got back land where I found Mistress a vacant “bali-bed” on the beach where She rested and slept for a couple of hours while She recovered.  “I’m definitely not going on another boat ever again” was all She could muster as She slipped off to sleep

Who exactly is this Charlie?

We decided to ward off feeling of being cooped up in the hotel by arranging a day out to one of the public beaches in the heart of Cancun.  Now Cancun is definitely a party place and it is a resort on an epic scale – a bit like Vegas-on-Sea really.

Mistress had also decided to get a new small tattoo while there and as we searched for a tattoo parlour in the main tourist area of the resort we begin to wonder “Just who exactly is Charlie?  And how does he have so much fun?”  Given that the bars had yet to open and we had only walked about 200 yards we were surprised just how many times we had been offered to meet this Charlie guy – seemingly a very popular chap in Cancun.  Four times in 10 minutes in all we were offered it – totally openly and brazenly – quite an eye opener for both of us definitely.

Surfing Legend & Baywatch babe

While chilling at the beach in Cancun we hired a couple of body boards and arranged some instruction for them.  The surf was pretty epic – plenty of surfers out and the life guards constantly making sure no one was going too far in the water due to the conditions and the various riptides present.

The body boarding was awesome – riding some major waves and it turns out that not only is Mistress Sarah a stunning Goddess but also a body boarding legend – catching a number of big waves and riding them all the way back to the beach time and time again – a real natural.

It was exhausting making your way out to the ideal point to ride the wave, working your way through the crashing waves time and time again – after a rest we set out again without the instructor.  Unfortunately I got slightly too close behind Mistress as we dived though a wave and Mistress’ board launched itself with the wave and smashed me clean in the face just above the eye and I went down like a sack of potatoes – as I got myself to my feet only to be hit by the next big wave, I desperately tried to get myself back to my feet but kept getting battered by wave after wave as I tried to recover my balance – thankfully Mistress saw my struggle and appeared like Pamela Anderson through the waves to help me back to my feet and back to the shore so I could get my breath back.  Not just a surfing Goddess but a Baywatch Babe as well.

Dolphin Time

On the day of Mistress’ actual Birthday I had arranged for us to swim with Dolphins which Mistress had not previously done.  Mistress was quite wary as we waited to enter the dolphin enclosure.  We waiting in the water and straight away the dolphin trainer asked Mistress to line up for the signature “dolphin push” were two dolphins push you by your feet through the water and lift you up and out of the water.  Mistress’ face was a picture as She quickly instructed me to go first.  The experience was fantastic, really close interaction with these amazing animals getting to touch them, getting “kisses” from them and lots of other activities with them.  They really are beautiful intelligent gentle creatures and we both really enjoyed the experience.

Afternoon Playtime

As we waited for the shuttle to get back to the hotel Mistress advised me that She had plans for me when we got back the hotel.  I was still incredibly horny from all the teasing, edging and talking about what might be in store for me so the 30 min ride back to the hotel felt like the longest journey ever.

On returning to the room I was instructed to shower and ensure I was fully “clean” for when Mistress returned from Her lunch.  Being clean meant I knew one thing for sure – my slutty arse was in for a treat at some point in the day, other than that I was unaware what was in store ……..

On returning Mistress instructed me to lie in the middle of the bed and I was promptly tied with my leg spread as wide as possible with my arms stretched far above my head – unsurprisingly I was in a state of considerably excitement at this point.

Mistress then teased me briefly wondering out loud whether She was going to hurt me or tease me – why settle She decided and opted for both.  Donning latex gloves She proceeded to edge Her dripping had cock liberally with deep heat – this wasn’t the first time and Mistress knew that despite the building pain Her cock would continue to remain desperately hard.  After a few edges Mistress collected Her pool stuff and promptly left the room “toodles!!!!” she cheerfully called out as She left the suite with me hard as hell despite the burning sensation.

Letting you into a secret – being left tied on holiday by a hot bikini clad woman is one of my longest standing and hottest fantasies and Mistress was only too happy to indulge it as She was very much looking forward to putting her particular spin on it.  

I was left for goodness knows how long – straining and struggling against the ropes, pulling hard on them to see just how helpless I was – the struggling only confirmed the obvious – I was going absolutely nowhere.

Suddenly there was a knock at the door – then it opened – “Ola Senor ……”

Oh god – Mistress hadn’t put the do not disturb sign on and I was spread eagle on the bed naked as the day I was born surrounded by a number of kinky sex toys Mistress had laid out for later ……

“Not today please!!!!!!!”

“Senor?”

“Am sleeping ….. no clean today please!!!!!!!”

“Ola Senor?????”

“No clean, please, no clean Senorita!!!!!!”

Then a loud familiar laugh as Mistress popped her head round the corner in tears of laughter – I nearly said something I shouldn’t as Mistress knelt down on the bed all wet in her tiny bikini still laughing at me.

“How’s the cock – still burning?”

She was already slipping on the latex glove and liberally squirting the deep heat on it again.  Once I was fully coated She then got a cotton bud and covered that with the deep heat and slowly inserted down my urethra – ouch!!!!!!!!

Mistress then picked up Her favourite toy – Her plastic whip and advised She was unhappy I was completely unmarked and promptly proceeded to rectify it as my hopelessly exposed upper thighs were thoroughly addressed with a number of marks.  After a few more deep heat coated edges Mistress then departed again to leave me hard and desperate once more.

Again after I don’t know how long relaxing with a few cocktails by the pool Mistress returned.  She had a long relaxing shower as I lay wondering what was coming next.  Soon I found out.  Mistress decided to heat my thighs up a bit with Her leather paddle before re-applying more deeper marks with Her whip.  Then She pulled out the enormous long dildo from the draw.  I was pretty sure I hadn’t had anything that big inside me before, sensing my concern She simply said – “don’t worry its going all the way on one way or the other bitch – just accept it”

I was then fucked senseless with the dildo and simultaneously edged time and time again – I was practically screaming to be allowed to cum I was worried Mistress might “treat” me to a ruined orgasm and several times it took me an almost superhuman level of self-control to avoid it.  Eventually though I passed the point of no return and thankfully Mistress kept Her hand stroking Her cock while She fucked me arse and I exploded after days of edging and teasing – the cum shooting several feet in the air – pretty much above the height of Mistress’ head (video of this available on Mistress’ twitter TL)  I thanked Mistress and shortly after was released to clean myself up.  I gave Mistress a massive cuddle and thanked Her for making one of my fantasies come true – it was a really special afternoon and I took me a while to come down from the high.

Monkey Business

One of Mistress’ favourite animals are Monkeys.  I had researched long and hard after booking the trip and found a Monkey Sanctuary about 90 mins away from the hotel which is a no profit charity run by a husband and wife totally devoted to rescuing Spider Monkeys from beach photographers / tourist attractions etc.

This is a magical and inspiring place, they have 90 monkeys, they are totally passionate about what they do and it really comes through. It is not a tourist attraction, they only allow two visits per week and only small groups are allowed each time, they only do this to raise funds to keep the sanctuary going and raise awareness of the Monkeys’ plight – they are practically extinct in South America.

The experience was incredible, magical, inspiring, and humbling.  You enter the enclosure and sit down with a small amount of food and the monkeys then basically come and spend time with you on their terms.  They sit on you, climbing on you.  I couldn’t believe it when straight away one of the monkeys came over to me put her arms around my shoulder and hugged me while looked straight into my eyes.  I gently rocked her as she cuddles up to me.  It was almost difficult to describe how it felt.  All around Monkeys were climbing on the group, cuddling people, sitting on them, playing with people’s hair, exploring us.

One of the golden rules we were advised was that you had to keep your palms open when you had food in them so the monkeys could take the food easily – one of the dominant monkeys who is known to be a bit of a head case is known to bite if you have a closed fist with food in it.  We followed the instructions to the letter with Mistress Sarah allowing one of the smaller monkeys to eat out of Her hand. However the monkey was a bit slow eating the cheerio after taking it out of Sarah’s palm and looked away briefly – typically mischievous as She is Mistress Sarah promptly snaffled the cheerio back while the monkey wasn’t looking and the monkeys’ face when it went to eat the Cheerio was a true picture  - Sarah & I both in fits of laughter as the monkey was double checking its palm and under its legs for the missing food – Sarah quickly gave the food back to the Monkey with it quizzical expression still on its face where the food had gone.

 It was a truly special emotional hour & half and no-one left the enclosure untouched by the experience.  Afterwards the owners sat and shared their life experiences, told us about monkey births and animals they had saved – we could have stayed all day.

Magical

Paddling about

Several days later after a day by the pool enjoying a “couple” of cocktails – as in quite a few and then some Mistress instructed me to collect our belongings and return to the suite with Her.  I was then told to shower to get clean then to present myself with my collar at Mistress’ feet.  I was collared then Mistress pulled my roughly to her feet by my collar and told – “I’m feeling very very very bitchy slave – go to the bar and get me some more drinks now”.  I quickly dressed and donned my usual fleece top, entered the busy bar full of celebrating wedding party and returned to the suite.

“Get on the bed bitch –now – head down”

Mistress then proceeded to comment on the obnoxious whiteness of my arse which needed attention – which She assured me it was going to receive in spades.

Over the next two and half hour I was subjected to the most brutal beating since I have served Mistress Sarah, I was beaten hard repeatedly with the wooden paddle time and time again, I was made to crawl out naked to the balcony where I was kicked repeatedly in the balls as I lay on my back with my legs spread eagle – desperately trying to keep quiet to avoid drawing attention from adjacent guests, time and time again I had to crawl back inside back onto the bed to be paddled again and again before crawling out to the balcony.  I had to make another visit to the bar to fetch more drinks for Mistress

I was desperate for the toilet, Mistress enquiring which type of visit I needed, answering that I needed a pee I was instructed to fetch an empty cocktail glass and fill that rather than use the WC.  I think everyone knows what was coming next as I was made to drink a full cocktail glass of my own piss as Mistress enjoyed Her cocktail.

Again I was instructed out onto the balcony where Mistress made me kneel as she teased my cock with Her feet and hands subtly behind the balcony table – I was close to cumming when yet again I was told to crawl back to the bed.  Mistress asking me how old She was  - “29 Mistress”

“Count bitch – you can back out any time you like by the way”

Whack “One Mistress”; Whack “Two Mistress” …

Mistress was at this point standing by the bed and hitting with a full swing harder than ever before

Whack – harder still  “THREE MISTRESS!!!!!!!!!!!!!!”

I cowered to the side away from Her

“Get down BITCH!!!!!!!!”

I was shaking, trembling ……. I had absolutely no idea how I was going to get to five or six never mind 29

“GET DOWN BITCH!!!!!!!!”

I laid back down

Somehow I got to ten

Somehow I got to fifteen

“How many left bitch?”

“Fourteen Mistress”

“Good”

“By the way – I haven’t even started with the whip yet – Ill spare you the back as you are so sun burnt plus it’ll be a new experience whipping your arse

Twenty came and went, harder and harder, tears were close to my eyes but I somehow kept them at bay

Somehow 29 came and then a special treat – nr 30 for next year as Mistress put it – it was the hardest She had ever hit me with anything and I thought I would hit the ceiling – I curled into a ball on the bed away from Her – looking pleadingly into Her eyes hoping for some mercy – She looked back at me coldly “You might be my friend but firstly you are my slave and bitch and tonight you are only my slave. Get down now!” Then She picked up the whip

I’d love to provide a stroke by stroke description of the whipping but I can’t – I was lost in a world of pain and despair, All I remember is Mistress moving around the bed whipping me from different directions and angles – Her only words to instruct me to get down whenever I curled into a ball with pain.

Eventually I was told 6 more – I could see a light at the end of the tunnel at last

The light was actually a train coming the other way to be honest as each of the 6 were delivered with a force I had never had before, I screamed into the duvet, I trembled, I begged – all to absolutely no response other than the next blow, harder than the one before.  Finally the 6th came – and I cannot describe the pain – I curled into a shaking trembling ball at the head of the bed

“Do you hate me now bitch?”

“Feeling angry?”

I could only shake my head – I had been taken to my previous pain limit and then given a plane ticket to a new level of pain I had never experienced.

Mistress then told me to lie on my back as She knelt astride me – looking down on me with danger in Her eyes – “You are lucky I haven’t whipped You till You bled all over the floor tonight bitch” (Despite the fact the bed sheet was already covered in blood from my destroyed arse)

“If I had you in the dungeon in this mood you would be in serious trouble”

I couldn’t and still can’t imagine what on earth what serious trouble would be like – I had been utterly battered for 2.5 hours, I was exhausted and was hoping beyond hope that Mistress had got Her bitchy evil desires fully satisfied for the night.

I was wrong

“Right put the TV on bitch”

I found the remote and tried to connect the TV to the Kodi stick we had brought with us – (The TV was somewhat frustrating all holiday in that there was no obvious button to switch to the required AV slot and I stood there desperately trying to connect it – then Mistress began whipping my arse again from the bed telling me to hurry up – sadly the TV was also in bitchy mood and I received at least another 10 or 15 strokes as I desperately fumbled with the remote before it finally did what I needed.

Once we loaded the film I was again fastened tightly hand and foot to the bed for another nights “sleep”

The morning after the beating Mistress and I had a full debrief – Mistress was very careful to make sure I was OK after the night before – knowing it was definitely the most intense and brutal experience I had had with Her. She explained that She hadn’t really planned it but had basically just started to feel really sadistic and bitchy about an hour before coming back to the room and needed to take out those feelings on me. She wanted to make sure I was feeling OK about everything and check that I was comfortable and happy with everything.  It was great to talk about it and we had a good giggle at times and I felt really good after the chat – I felt really proud when Mistress described the intensity of the session as a 9 or 10 out of 10 and I had taken it for Her.  People might not really appreciate it but I am actually a bit of a wuss to be honest, pain itself is not my thing in itself, but being the slave of a Mistress who genuinely enjoys causing pain it is part of my devotion to Mistress Sarah and I was incredibly proud when She explained just how much She enjoyed it and how severe a beating I had withstood for Her.

How many is too many?

We went to the pool and I was instructed to get to the bar as it opened.  As I returned with the cocktails Mistress told me “by the way – you are getting pissed today – I’ve never seen you drunk yet and today you are getting hammered”  #forcedintox anyone?

We spent the day sunbathing, chatting with other round the pool, playing water polo and drinking, drinking and more drinking –oh and some more drinking.  Now given that we had spent about 10 days indulging in lots and lots of cocktail drinking I figured it was going to take something serious to get to the level that Mistress would consider “drunk”.

To say I lost count of how many cocktails disappeared during the day is an understatement – I genuinely haven’t a Scooby how many we got through but I’m pretty sure it might fall under the “binge drinking” guidelines lol

Eventually as the swim up bar was closing about 5pm suddenly myself and “the wall” met each other, shook hands and exchanged pleasantries.  I was shitfaced, hammered, blotto, three-sheets-to-the-wind, spannered etc.  I turned to Mistress and told her “I’m done, I’ve gone, I’m proper hammered”  

She was very happy

Thankfully on return to our room I was able to order room service to help soak up the huge volume of alcohol we had both got through – can’t beat chicken nuggets and a large cheeseburger and fries x 2 to soak up a massive drinking session and thankfully by the next day I was back in the land of the living to serve Mistress again properly

Homeward Bound  

On the final night I spent tied tighter than ever before and Mistress spent several hours teasing Her inevitably hard cock with Her immaculate feet and hands while we watched a film back in the suite after out last meal out together. Thankfully eventually She relented and took pity on Her devoted slave, and treated me to a last cum of the holiday.  So finally after 11 amazing incredible night we woke of for the final morning.  After Mistress released me from 12 hours of tight bondage I donned the famous red fleece, fetched Mistress Her last breakfast and then whilst Mistress spent the last morning chilling by the pool I packed our cases and checked us out of the hotel ready for the flight home.

Thankfully the flight home was much less fraught then the outbound flight and we touched down in Manchester after flying through the night.

I just want to say Thank You to my friend and Mistress for an amazing holiday, I had a fantastic unforgettable time everyday and it was truly truly special, magical experience and hope it gave You a birthday to remember for a long time to come.

Your Nigel / Jessie

XX