Emily's Second Solo Holiday Pt. 01

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Will Emily's Second Solo Holiday be as good as her first.
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Part 1 of the 7 part series

Updated 06/10/2023
Created 08/12/2020
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If you haven't read 'Emily's First Solo Holiday' and 'Emily's Home Life Changes' I suggest that you read them before reading this.

Part 01

Before I tell you about my second solo holiday I think that it's best that I tell you about some of the things that Jack has been making me do since I wrote about how my home life has changed.

I think that it's right to say that I am VERY happy living with Jack and being his submissive exhibitionist. We've even talked about us being a permanent couple and maybe even having kids but we've both decided that life as it is at the moment is way too much fun to seriously think about major changes. We've decided to re-visit serious changes in about 10 years. Until then we're going to just keep doing crazy things.

Just a quick reminder about me, I'm 23 years old, slim 30A 23 29, with shoulder length strawberry blonde hair, 5 feet nothing tall. I've been told that I have a cute little bubbly butt. I studied engineering at university and now have a good job working in central London that I commute to each day on the London Underground.

Right, since 'Emily's Home Life Changes', Jack has continued to make me do things that before 'Emily's First Solo Holiday' when I was engaged to that looser, John, I would never even have thought of, never mind actually do.

After the walk in the Epping Forest Jack has taken me on many countryside and coastal walks and I am usually naked apart from some hiking boots. Jack carries my dress and a few essentials for us both, just in case.

We've come across quite a few people whist out walking and just about everyone is very friendly towards us, often stopping and talking to us. I'm amazed by the number of people who have told us that they'd love to do the same if only they had the courage.

Each week Jack takes me to his gym for a workout and all that he lets me wear, which is good with me, is a thin, cotton tank top and a very short, white skater skirt. It's not revealing when I'm just stood there, but as soon as I bend over even the slightest bit my butt becomes visible, and you can imagine what is on display when he gets me to do some floor exercises.

Jack has discussed my attire with the gym manager and he told Jack that membership has gone up since Jack started taking me there.

Jack also takes me jogging once a week as well. We sometimes go around the local park but sometimes run along the main street and I often get a few comments, usually from groups of young men about my pokey nipples or the fact that my skirt bounces up and they can see my slit or my butt; so they say, I can see my nipples but not my slit or my butt so I have to take their word for it. Jack just smiles when I ask him.

Jack has also taken me to a couple of CMNF dinner / dances which I loved. We travelled there on the underground with me just wearing a short coat and heels. The coat fastens with just a tie belt and it kept 'accidentally' coming undone leaving the coat open and giving the people opposite me quite a surprise. He's also had us sitting on the trains opposite men and he didn't need to tell me to keep my knees far enough apart to let the man / men opposite me see my slit.

The dinner / dances are great and we met lots of girls like me and their partners who like showing them off. I really loved being able to talk to strangers and dance totally naked with clothed men close by. I also really love the table next to the dance floor where girls can go and lay on it, and any man can go up to them and explore the bodies with their fingers and mouths.

At both events Jack sent me to the table twice and each time I got finger fucked and eaten out, having glorious, intense orgasms each time. It was really nice having a man from the same table as us come and make me cum then go back to our table and act like nothing had happened.

Jack also visited the table and pleasured some of the girls although I did notice that he only went there if the girl had a similar build to me. It confirmed to me that Jack much prefers small girls with small tits.

I'm also still going to and from work on the underground wearing just a short dress or skirt and top, then getting changed into my work clothes in the toilet of a fast food outlet near where I work. The groping and finger fucking is still taking place on the crowded trains and I'm really happy that I work 'normal' office hours, I've lost count of the number of orgasms that I've had on the way to work. I must be 1 of the few people who actually enjoys their commute to and from work.

Jack is still throwing parties, and some of the other residents are as well. At every one I am naked, the only one naked, and I love every minute of it. At some of them I have to get on the table after most of the food has gone and the deserts are put on and in me and people eat them off me anyway that they can.

I love having orgasms on those tables with all our neighbours standing watching me.

I think that by now, everyone in the apartment block has seen me getting dressed or undressed down in the entrance area. What they have never seen is me wearing a bra or knickers. I don't even wear those for work now, my thick blouses and knee length skirts keeping me looking professional.

I've invested in a home laser depilator and it's amazing. After about 3 sessions, with Jack's help, I have no hair below my neck and every few weeks Jack closely inspects every square millimetre of my body and lasers any hairs that have appeared. Why hadn't those machines been invented 10 years ago when I first started shaving?

******

One night, in bed, after an exhaustive sex session where Jack had tormented my pussy using my magic wand and remote controlled vibrator that shakes my insides so much that I sometimes fear that they will turn to jelly, then fucking me to 3 more glorious orgasms, we were laying there talking and Jack told me that he was thinking of going on a holiday with his mates and that I should think about going on a holiday with my mates.

At first I was a bit confused and disappointed, but he went on to explain that us being apart would bring us closer together in the long term.

My mind went back to my first solo holiday in Ibiza and the totally awesome time that I'd had. That holiday really changed my life into the amazing one that I have now. Those guys that were in the next hotel room to me really brought out the real me and changed my outlook on life for ever.

I knew that it would be impossible to repeat that holiday, and that if I tried it would be disappointing.

Jack went on to say that some of his mates were thinking of going on a lads holiday to Ibiza after Jack had told them about some of the things that I'd done, and that he was considering joining them. He also again told me that he thought that I should do something similar with some of my girl friends.

I reminded him that I didn't have any girl friends that weren't married or that I would want to go on holiday with so he suggested that I try some of these website that arrange singles or 'alternative' types of holidays. I told him that I wasn't sure what he meant so he offered to help me find something.

We both agreed that finding a holiday for a submissive exhibitionist with a body like mine would be a challenge but we also agreed that there must be holidays out there where people can be their true selves, it was just a case of finding them.

Getting Jack's holiday sorted was easy, just 1 phone call to one of his mates, but both of us spent hours trawling the internet looking for something that would let me be my true self. It was Jack that found the post that would eventually become my second solo holiday, and one that would equal my first solo holiday, but in a different way.

It was an American couple who were spending a year in Europe and were hiring a small yacht for 3 weeks to cruise around the Greek islands and they were looking for a submissive young girl to be their 'deck hand' for the 3 weeks.

Well, when I read the post my mind went into overdrive and so did my pussy. It was obvious that for 'deck hand' you should read 'sex slave'. After reading it for a second time I begged Jack to fuck me right then. He reminded me that it was him that decided when we had sex and he told me to bend over the table whilst he spanked my bottom for being so bold.

After about 50 swats he did fuck me, so hard that I got slight bruises where my upper thighs were rammed against the table.

Anyway, the next day Jack told me to reply to the post asking for more information.

Almost immediately I got a reply asking for details of my body and what I was looking to get out of the trip. Well my body details were easy but describing what I wanted out of the holiday was a bit more difficult. In the end Jack and I agreed on,

'I am currently living with a man that dominates me and makes me do many things that your average girl would be horrified at, like going to the gym for a workout wearing nothing but an ultra short dress, or hosting a party where I am the only person naked.'

Within a day I got a reply saying,

'My wife and I (Wren and Aryn) will be cruising the Greek islands for 3 weeks at the end of July and we are looking for a submissive young girl to do a lot of the work involved and to be our sex slave for the duration. If this sort of holiday appeals to you please send 5 nude photographs of yourself to the email address below.'

That was it, short and sweet, but, as Jack said, they didn't want to give too much away to someone who may not be suitable for their needs.

That evening Jack scrolled through the thousands of nude images of me and selected 5 that he thought would meet the couple's requirements. One of the photos was of me having a spreadie, held up by 2 young men, on my holiday in Ibiza. It is a high resolution photo and you can zoom in and see a lot of detail, including my juices seeping out of me.

I sent them to the email address that evening.

The following day I got another email from Aryn,

'Your body meets our requirements so I have attached a couple of photos on my wife and myself. If after seeing those photos you feel that you could submit to our sexual demands please reply sending us a doctor's letter proving that you are free of any sexually transmitted diseases. At the start of July we will send you a similar letter and will expect another, similar letter from you. After we receive these I will send you our skype handle and a date and time when we can meet on skype and get to know a little about each other before the trip.

Also, please send me a list of red-lines that you are not prepared to cross.'

Jack and I studied the photos of Aryn and Wren just after he fucked me in bed that night and we both agreed that they looked okay, not ugly or fat, just a regular couple. Aryn looked to be a big man, but not a fat guy and Wren looked quite small next to Aryn.

"So could you let this guy fuck you Emily?" Jack asked.

"I could, but not without your permission Master." I replied.

"Well slut, you have my permission, in fact I hope that he fucks you 5 times every one of those 21 days."

The next day I visited a clinic and a few days later I received the test results and emailed a copy to Aryn and also attached a photo of Jack spanking my bare butt.

In the email I listed my red lines list of just 4 items: -

Drinking Piss.

Eating Shit.

Getting any type of physical damage that would not heal within a couple of days.

Getting Arrested.

The reply also gave me Aryn's skype handle and a time to call him.

"Should I wear some clothes for the call?" I asked Jack.

"Certainly not. You cannot wear clothes in this apartment so you would suffer the consequences if you do."

******

The appointed time arrived and I made the call. As soon as the video connection was made I saw that they were sat at a table and Wren was topless.

"Well hi there Emily, it's good to see you at last. I'm assuming that you are naked and not just topless?"

"Yes Aryn, I am."

"Emily, when we are alone or with Wren you will address us as Master and Mistress. You will only use Aryn and Wren when other people are around."

"Yes Master."

"Good, you will quickly realise that we are friendly people who wish you no harm providing that you do as we say."

We talked for ages with me telling then a lot about me and my life with Jack. I learnt that Aryn is an ex Navy Seal who had inherited a lot of money and was out to enjoy life. Wren was his childhood sweetheart that he had married just before he qualified for the Seals.

I didn't find out if Wren was bottomless as well as topless, but Aryn told me to climb onto the table, put my laptop between my legs and bring myself off for them. Obviously I did and they both appeared to like what they saw.

I was still sat on the table with them getting a great view of my dripping pussy when Aryn said that he wanted to talk to Jack. I called out his name and he came and stood beside me.

"Hi Jack," Aryn said, "nice to meet you buddy. Thank you so much for lending Emily to us, I'm sure that she'll provide a great service to us and really enjoy herself."

They chatted for a while with me still sat there with my legs wide open.

The call ended with them reminding me to send them another certificate proving to them that I was disease free at the start of July, and Aryn telling me to email me my address

******

The day for my departure finally arrived and Jack woke me with his cock sliding in and out of me, he gave my body a full inspection and removed the odd hair that had decided to grow. Then, after breakfast I picked up my small clutch bag that contained everything that I would be taking, slipped on my heels, a very short summer dress and sandals; and Jack drove me to the airport to catch the scheduled flight to Athens. All I had with me was my passport, flight tickets, boarding card, phone and a small amount of money, GB pounds and Euros, one of my credit cards and a couple of personal items. Those were the only things that Aryn had told me that I would need.

I didn't look out of place at Gatwick as there were hundreds of people going on their summer holidays and most of the girls were as scantily dressed as I was although I doubt that most of them were knickerless and braless like I was.

I had a window seat and by the time I got to it two men were sat in the seat between my seat and the aisle. Neither of them got up to let me in so I had to squeeze passed them. I did it facing them and my short dress rode up as it brushed against the backs of the seats in front. I'm not sure if they saw my slit or not.

Finally in my seat I looked down and saw that my bald pubes were visible. I fastened the seat belt and put my hands on my lap covering my pubes. It wasn't that I wanted to cover my pubes, it was 2 other things, firstly I didn't want the cabin crew to see my bald pubes when they came round checking that all the belts were fastened, and secondly, the fingers on my right hand could play with my clit whilst the action was covered by my left hand.

The nearly 4 hour flight would have been boring if it hadn't been for a few things, the fingers on my right hand were busy most of the time. Whenever I saw the man next to me looking at my bare legs I moved my hands away so that he could see my bald pubes, slit and clit.

The anticipation of what was ahead of me, and my fingers were causing my pussy to stain the seat that I was sat on to such an extent that after a couple of hours I had to go to the toilet to relieve the sexual tension that was in me and to clean and dry around my pussy and inner thighs.

The men still wouldn't get up when I excused myself to get out to the aisle so this time I squeezed passed them with my butt to them and I made sure that my dress did ride up. They could not have missed seeing my bare butt that was virtually in their faces. I went to the toilets in the back of the plane so they did not see me approaching after I had taken care of my personal business and as I got back to the seat behind them I just caught the end of a conversation about my butt and my lack of knickers.

I smiled, stepped forward and asked them to excuse me again. Again they didn't get up so I again squeezed passed them, this time with my front to them and I made damned sure that my dress rode up and there was no way that they could not have missed seeing my bare stomach, slit and protruding clit.

I sat down on the front edge of my seat and lay back knowing that my slit was still very visible to them.

After a few seconds I looked at them and saw that both of them were looking at my slit. I would have smiled at them but they wouldn't have seen my face so I sat properly and put my hands on my lap again. Again letting the fingers of my right hand idly play with my clit.

As soon as the plane door opened in Athens I knew that I was going to have a great time, the heat rushed into the plane and when I got to the door and looked out and up it was a glorious day, blue sky and a temperature that England only saw about once a year - if we are lucky. The skirt part of my dress fluttered about in the slight breeze and I made no attempt to hold it down, not caring, but hoping, that a few people would see that I had nothing on under the dress.

No waiting at the luggage carousel for me and I walked straight through to the arrival hall where Aryn had told me they would be. It was easy to see him as his head was well above everyone else's in there.

I smiled as I walked up to them, and as soon as I said hello Aryn bent over and his hands went down to the back of my thighs, slid up to my butt under my dress, and he lifted me up so that my face was in front of his. His fingers found my pussy as I instinctively wrapped my legs around his waist and it was only after a few seconds that I realised that my dress had ridden up and my whole bare butt was on display to everyone around us.

When Aryn finally put me down Wren hugged me as well, and again my dress rode up but only the bottom part of my butt was exposed.

As we walked out to the waiting taxi Aryn talked and I almost instantly felt comfortable and safe with him. Even though I am a karate black belt, no one in their right mind would argue with this gentle giant.

We got to the taxi and just as I was about to get into the back alongside Wren, Aryn said,

"Take your dress off Emily and give it to Wren, you won't be needing that for 3 weeks."

I did as I was told, much to the surprise of the few tourists that were walking by, and the driver who I saw smiling through one of the mirrors. I took my time getting in, watching Wren fold my dress and put in in her bag.

The drive took us almost an hour and all the time Aryn was talking to all 3 of us, asking all sorts of questions about all sorts of things, and he wasn't shy about asking things like was I due to have my period in the next 3 weeks, or reminding me that anal wasn't on my list of red lines so was I happy to take his cock up my ass.

Aryn asked me if I wanted a 'safe' word then told me that he would stop doing whatever it was that he was doing to me but only that. We could well be in the middle of the Mediterranean so we'd discuss the problem and get over it.

I replied saying that it was a good idea and he suggested 'Priapus'.

"Isn't that the Greek god with the humongous penis?" I replied.

"It's not that big, wait until you see mine." Aryn replied.

I looked to Wren, she was smiling and nodding her head. I turned to look at Aryn and he too was smiling.

"I'm glad that I do my kegel exercises." I replied.

Aryn then cursed another motorist who had just cut us up then the conversation changed to crazy Greek drivers.

All the time the driver was listening to Aryn and the replies from both Wren and myself and I wondered if he understood English, and if he did, what must he be thinking.

12