Emily's First Solo Holiday - Cover

Emily's First Solo Holiday

Copyright© 2019 by Vanessa Evans

Chapter 3

Fiction Sex Story: Chapter 3 - After breaking up with her boyfriend Emily goes on holiday on her own.

Caution: This Fiction Sex Story contains strong sexual content, including Consensual   Heterosexual   Fiction   Gang Bang   Exhibitionism   Masturbation   Oral Sex  

Before you read this part I strongly suggest that you read the previous part. It will give you the background that will make this part a lot more enjoyable.

Part 03

DAY 05


I was actually woken by an unknown cock going in and out of my vagina. I sighed and then moaned as his speed increased until I had my first orgasm of the day. When he’d cum and started to go soft he rolled over and I turned to see who it was.

“That was nice Harry, it set me up for the day.”

The night’s sleep had worked wonders with me, both energy and pussy which was no longer sore.

“You guys don’t have breakfast here do you?” I asked.

“No, we didn’t expect to be up in time.”

“I’ve always been a bit of a morning person myself. I’m going to have a shower then go and get something to eat. You can stay and watch me shower if you want.”

By that time I was on my feet and looking down at Harry, and he was looking up at my pussy.

We ended up in the shower having another fuck before I kicked him out and got ready to go and have breakfast; not that getting ready took me long there, the longest part is the shaving followed by the brushing of my hair.

I wrapped a half sarong round my waist, slid into my flip flops and went to the restaurant. It was later than my previous visits and the place was about half full. I was feeling quite happy so as I sat down I slid the sarong so that the knot was on my stomach. When I got up to go to for the food my pussy, as well as my uncovered tits were on display for anyone to see, but me acting like I was dressed like a nun meant that hardly anyone really looked at me and I only managed to get one smile from one man.

As I ate I decided that I was going to have a lazy day by the pool. I just knew that if I tried to make that day better than the previous day there was an almost zero chance of succeeding so why even try. Besides, one time that I’d looked down to the pool I was sure that I’d seen a naked woman so it was a good time to improve my all over tan.

As soon as I was out of the restaurant I took the sarong off and walked back to my room with it in my hand. I felt good and happy as I looked down to the pool. About half the sun loungers were still free so I didn’t have to rush. Having said that, I did want to work on my tan so I threw a few things into my bag, put the sarong back on and headed down.

I managed to get a lounger about half way along the side of the pool and as soon as my sarong came off and I got my bottle of sunblock out there were a couple of guys beside me offering to help me spread the sunblock all over me.

Well, there was no way that I was going to reject an offer like that so I lay on my stomach and introduced myself. Tom and Andy were good, but not in the same league as Manuel. What’s more, they didn’t have the nerve to touch my pussy and I didn’t invite them, not like my tits which they did put the block on, after asking that is, but neither of them played with my nipples.

I had my quiet day, although quite a few guys came and tried to hit on me. A waiter kept walking around and I ordered a drink a couple of times, him apparently not caring that I was naked, well it was an adults only hotel.

Neither of my sets of neighbours were in their rooms when I got back there and I got showered, put just a dress on and went for a quiet meal and then a stroll before having an early night. I still hadn’t caught up on my sleep.

DAY 06


None of the guys came to wake me up even though my door key was on the table on the balcony, I guessed that they’d got lucky else where so I showered then went for breakfast.

On my first day in Ibiza I’d noticed that a lot of the girls were wearing either one-piece swimsuits or bikinis that were of the thong variety and very high-cut at the sides so that they were walking around with their butt cheeks on display all the time. That wasn’t the interesting bit because I too had my butt cheeks on display all the time.

What was the interesting bit, was the cover-ups that they were wearing. A large percentage of the girls were wearing mini-dresses made of net or lace, and the holes in the net or lace were big enough to not really cover anything. Nothing was hidden.

I decided to have a day going round the shops to see what I could find. Now I like my see-through dresses and they’ll be great for England, but these net dresses were going to the next level, and I wanted in.

As I went around the shops I was a little disappointed to find that some of the dresses were made of stiff, plastic net and would not be comfortable at all. I’m happy to say that I did find some that were comfortable to wear and still have big holes in them.

I spent over 300 euros getting some and looked forward to going out in them.

When I got back to my hotel I was a little surprised to find Luke, Harry and Will sat on their balcony talking and drinking beers.

“Hi Emily,” Luke said, “get yourself naked and come and have a cold beer, we’ve got a proposition for you.”

As I did that Will lifted one of the chairs from my balcony over to theirs.

“So guys,” I said after I’d taken a swig of cold beer, “what’s up?”

“We’ve hired a Jeep for 4 days and it has 4 seats so we were wondering if you’d like to fill the fourth seat?” Luke said.

“What sort of Jeep?” I asked, “Not one of those dinky suzuki ones, or worse, one of those stupid, noisy citroen ones?”

“No, a proper Jeep.”

“A Wrangler?”

“Yes.”

“Does it have a roof and doors?”

“It didn’t when we looked at it this morning.”

“Good, I’m interested.” I replied. “Tell me more. How much do you want for my share?”

“Nothing,” Luke continued, “we were rather hoping that you might volunteer to, to be err...”

“What Luke’s trying to say Emily,” Will interrupted, “is that we’d like you to be our sex slave for the 4 days.”

“WHAT!” I exclaimed, “you’ve got to be joking.”

“Yes Emily,” Luke replied, “what Will means is that we’d like to be able to tell you what to wear all the time and that we’d like to fuck you quite a lot while we’re out and about.”

“Well that doesn’t sound too bad, a sort of continues gang-bang, that sounds like fun, but before I agree to it there are a few questions and conditions.”

“Okay, fire away, and why all the questions about the Jeep?”

“I happen to like Jeeps and want to get one some day. Right, I hope that you aren’t planning on me wearing much, you know that I like showing lots of skin.”

“Hell no,” Harry replied, “as little as we think that you can get away with.”

“Good answer, now drink and drugs, I want your word that you will be sober all the time, I’m not getting into a car if I think that the driver is under the influence of something.”

“Only the sight of your body Em.” Luke replied.

“Another good answer. I doubt that I’ve got enough condoms left for a 4 day continuous gang-bang and I’m guessing that you guys haven’t got many. When did you guys last get checked for any unpleasant diseases?”

“Relax Em, we all got checked just before we came here and we’ve been using condoms on the nights that we got lucky, and when we’ve woken you up.”

“And I’m good as well.” I replied, “so, what I was thinking was that we could go bare-back until one of us fucks an unknown person without a condom. Then we would have to go back to condoms and I don’t think that any of us want that. What do you think?”

Unsurprisingly, all 3 guys agreed but I did add that if any one of us caught anything then all 4 of us would catch it.

“Good, now if one of you is going to be fucking me every 5 minutes then someone is going to have to remember to take a towel for the Jeep seat each day, your cum will be leaking out of me all the time.”

All 3 guys volunteered to take a towel.

“And how are you going to decide which one of you is going to fuck me, when and where?”

“We haven’t sorted that out yet, we weren’t sure that you’d go along with it.” Harry said.

“Okay, I’’m sure that you’ll sort something out. One more condition guys, each time that we stop somewhere one of you is going to have to rub some sunblock on me. If any part of me is going to go red then it mustn’t be because of sunburn.”

“I’ll do it.” both Harry and Will said.

“We’ll sort out a rota.” Luke said.

“And I’m guessing that you won’t be able to keep me naked all of the time so I’m going to have to take some clothes with me.”

“A couple of those G-strings will do.” Harry said, “the ones with no material.”

“I think that I’ll probably need more than that, especially if you take me somewhere away from the beaches. Does the lock box in the Jeep work?”

“It did this morning.”

“Okay, I’ll put a few things in a bag and then you can choose what I’ll wear whenever clothes are needed. So which 4 days is it?”

“Starts 9 o’clock tomorrow morning.” Luke said.

“Good, plenty of time for me to get some breakfast and get ready. Where do we pick up this Jeep?”

“About half a mile down the road.”

“A bit of exercise as well.”

“Shall we all go out for a pre-adventure meal and drink?” Will asked.

“Sorry guy’s, I can’t make it tonight, there somewhere that I have to be. One of the reception guys told me about a place where girls get invited to be some business men’s desert.”

“That sounds interesting – if you’re a girl or a local business man.” Luke said.

“There’s times when I wish that I was a girl.” Harry said, “it’s easier for girls to have fun than it is for us guys.”

“Yeah, it is,” I replied, “but the next 4 days sounds like fun for all of us.”

“It will be.” Luke said.

We finished a couple of beers, talking about what the guys had been up to, then I left to get ready for the unknown.

I’d already seen the club as I’d been walking around and it looked like your average San Antonio night club from the outside, nothing spectacular, a bit seedy perhaps, but I was on holiday to have some fun and I couldn’t imagine that it was a front for kidnapping girls to sell as sex slaves so I’d decided to go.

I decided to wear a skater type skirt and top with nothing underneath, the skirt just being long enough to cover my butt and tingling pussy

I arrived at the club just before 8 o’clock to find that the door was open so I walked right in. It was quite dark compared to the bright lights outside but my eyes soon adjusted and I saw a bit of a dingy room. I started to have thoughts that I had made a mistake going there but a man came over to me and told me that they didn’t open until 10 o’clock.

I handed him Pedro’s card and told him that I was there for the ‘special’.

He smiled as his eyes went up and down my body.

“Right,” he said, “come with me.”

I followed him to what I assumed was a ‘private’ room in one corner of the main room. Inside was another girl about my age or maybe a bit younger. She too was wearing a skimpy top and micro skirt.

The man left and I turned to the girl and said,

“You here for the ‘special’?”

“Yeah, I’m Daisy. Do you know anything about this ‘special’?”

“Emily, only that it’s supposed to be all about pussy eating.”

“Yeah, that’s what I was told. I’ve come prepared for that.” Daisy said as she pulled the front of her skirt up to reveal her uncovered slit.

“Me too.” I said, lifting the front of my skirt.

Just then the door opened and a third girl was shown in.

After introductions and a flash of her (Donna) uncovered slit, the man came back and told us to follow him. He led us outside to a people carrier and told us to get in, which we did.

The journey took about 30 minutes during which us 3 girls joked about us getting taken to slave traders or to some sort of torture chamber. We were joking, but I suspect that the other 2 were a bit like me and wondering if it were true. The thought of lots of men eating my pussy was stronger than the fears.

We arrived at a nightclub (big signs) out in the hills but the vehicle didn’t stop in the big car park, instead it went round the back to where there were quite a few cars parked. The driver told us to get out then he led us into a large room, a sort of small barn, where we saw 2 huge, round, wooden, solid looking tables with about a dozen, middle-aged to elderly men sat around each table. They were all smartly dressed in expensive looking shirts and were eating, drinking and talking in Spanish.

I laughed to myself and wondered if this was Ibiza’s answer to the English Round Table of business men.

One of the men got up, came over to us and said,

“Good evening ladies, thank you for coming. Your job this evening is to dance on the tables until the meal is finished and everything is cleared away. Then you will go round each gentleman and offer your pussy for them to eat. Once they are satisfied you will go to the next gentleman and make the same offer. You will not stop the gentlemen from pleasuring you if you orgasm, those orgasms will be incidental to you letting them do what they wish to you. Any questions?”

“Yes,” I said, “there’s 3 of us and 2 tables.”

“Until the meal is finished 1 of you will be on each table, every 10 minutes 1 of you will be replaced by the third girl.”

“Okay,” I replied, “do we stay like this or do we get naked?”

“Loose the tops and knickers – if you are wearing any, but keep the skirts and heels we all like seeing bare pussy up a short skirt. The skirts come off at the end of the meal.”

“How much are we getting paid?” Donna asked.

“Two thousand euros.”

“Each?” Donna asked.

“Each.” the man replied.

I looked at Donna and Daisy and all our hands went to take out tops off.

“On the tables 2 of you,” the man said as he turned and went and turned some music on, just loud enough for us girls to work with.

Donna and I each went to a table where 1 of the men stood to let us climb up. I smiled at the man as I stepped up onto his chair, then the table. I saw his eyes go up my legs to my pussy and butt.

Donna started dancing in the middle of the table but I went nearer the man who had let me climb up and made sure that he got a great view of my goodies. After a minute or so I moved along to the next man then slowly went round the table making sure that they all saw what they were going to have for desert.

I’d just made it back to the first man when I saw Daisy motioning for me to climb down and let her up. The same man got up and let Daisy and I swap places.

I watched both Daisy and Donna to see if they were doing anything differently to me and I saw that neither of them had their legs as far apart as I had.

After a while I realised that Donna had gone round her table’s men nearly twice so I went over and waved to her to swap with me. Another man got up to let us swap and he was saying something but it was in Spanish and I hadn’t a clue what he was saying.

Thankfully, I managed to round the whole table before some waitresses came in and started clearing the tables. One of them looked up at me and smiled, she obviously knew what was going to happen next and I wondered if she was going to join us.

When the tables were clear, the original man who had spoken to us got up and announced that the feast was about to start. He said, in both Spanish and English,

“As usual, a bell will ring every 3 minutes then the girls would get up and move to the next man.”

Then to Daisy, Donna and me,

“Girls, take the skirts off then sit in front of the man nearest to you with your legs over his shoulders and let him feast on your pussy. You, (pointing to Donna who was stood on the floor), get up on a table. When the bell rings you are to get up and mover to the next man at the table in a clockwise direction. If, when you cum, the man will not stop eating you so do not pull back. I will tell you when to change table and when to stop, the intention being that all 25 men have enjoyed each of your pussies at least once.”

I’d wondered how it was going to work and the man had said the way that I thought was most productive, and most pleasurable for me, and Donna and Daisy.

Wow, what a variety of techniques and abilities, although in general, most were good and I managed to cum 4 times before the evening was over. I got to 2 men who had wet shirts and judging by the smell, either Donna or Daisy was a pee squirter. Nether man seemed at all worried or unhappy about being covered in pee and each one attacked my pussy with their mouth like I mine the last pussy that they’d ever see, one of them giving me my third orgasm.

I also squirted on one man, but it was vaginal excretions and I saw the white, creamy liquid on the man’s smiling face.

By the time I climbed down from the table for the last time my pussy was slightly sore but I didn’t care, I was happy, I’d cum 4 times and my pussy had been eaten by all of the 25 men.

All 3 of us girls stood there, naked, as the evening came to a close and the men left. The original man came of to us, thanked us and gave us an envelope containing our cash. He also told us that we could go to the, by then very loud, nightclub.

“What about keeping these safe?” Donna asked, waving her envelope.

“I’ll take you to the manager’s office and you can put them in his safe.”

“What about getting back to San Antonio?” Donna asked.

“Your driver is still here and he’ll wait for you.”

“And our clothes?”

“You’re not going to put them on?”

“I’m not, what about you Daisy and you Emily?” Donna continued.

“Well if you’re staying like that then I am as well.” I replied.

“Yeah, me too.” Daisy added.

“Bring your clothes and you can put them in your car. Anything else?”

Donna looked at both Daisy and me, we both shook our heads.

“Okay girls, lets go, bring your clothes.”

We picked up our clothes and followed the man out to the car park where we saw the car. The driver smiled when he saw us. We left our clothes then followed the man through the main car park and to the main entrance of the club where we walked straight through. On the way we got a few comments from some young men who were just arriving.

My pussy had been very wet ever since I first arrived there, but as we walked into the club I felt it start to tingle again.

The man led us through one large, dark room with lots of people, some looking at us, to a corner where a door had Private / Privado on it, and we went in.

A man in his thirties looked up from his desk and smiled when he saw the 3 naked girls. After a conversation in Spanish he gave us a pen and, in English, told us to write our names on our envelopes.

Donna started to take some euros out of her envelope but the manager stopped her and said,

“Don’t worry about drinks, naked girls always get free drinks here, just go to any of the bars like that.”

“Nice to know if Luke, Will and Harry bring me here.” I thought.

Now I’ve never been a great fan of nightclubs and this one was just a bigger version of the ones that I’d been to before; quite dark, very loud and of unknown cleanliness; but I’d never been to one naked before. If nothing else, hundreds of people were going to see me naked and that thought certainly aroused me.

Donna wanted to dance so the 3 of us did just that. Unsurprisingly, we got hit on quite a lot by young men of varying degrees of drunkenness.

It was Donna who first let a young man dance with her, and subsequently put his hands all over her. The idea of a man putting his hands all over me appealed to me but not a drunk man and just about all of the men around there were showing definite sign of alcohol usage, so instead I went to the nearest bar to get a drink.

What I hadn’t expected (probably should have) was for the men who were also queueing to get a drink, to want to get a feel of my interesting parts. At first I pushed the hands away, but when they came back to my butt I thought about me being on the London underground at the start of my holiday and getting groped, and relaxed and let the hands (more than 1 by then) wander all over my body.

I just stood there in a bit of a dream enjoying the hands. I vaguely remember both someone trying to hit on me, and the barman asking me what I wanted to drink, but I was enjoying the fingers that were sliding along my vulva and in and out of my vagina. I had never even considered someone groping me at a bar, and making me cum, because that’s what those fingers did.

I had a standing, shuddering orgasm and vaguely heard the words “she’s cumming”, but I didn’t care.

As the waves receded and my brain started to return to reality I heard myself asking the grinning barman for a ‘sex on the beach’. I’ve never had one of those before and haven’t a clue why I asked for it. Well maybe my subconscious brain was thinking about it and wondering if Luke, Harry and Will would fuck me on the beach.

Anyway, one of the hands came round to my stomach and then down to my clit. I had a second orgasm just as the barman brought me my drink.

When my brain returned to the reality of the situation, I picked up my drink and turned around and saw about half a dozen young men all looking at me. My pussy was tingling as I started to push my way through the men, their hands reaching for a final grope.

Part of me wanted to stay put but I knew that if I did I’d end up getting fucked by at least one of them and I didn’t have any condoms with me, so I kept slowly moving forwards, wanting the groping to keep going, and to stop.

When I got to the edge of where Donna and Daisy were dancing I took a deep breath and downed my drink in one go. I shook my head to clear it then looked at Donna and Daisy. Donna was dancing with a man, leaning back on him with his hands on her pubes. Judging by her face his fingers were working on her clit. Daisy was dancing(ha) with a much taller man, her arms were around his neck and her feet hanging in the air about 25 centimetres apart. She too had a look of pleasure on her face and I wondered if they were actually fucking.

A young man (not bad looking) came up to me and nodded his head to the dancers. I smiled at him and followed him into the middle of the dancers. It wasn’t long before his hands were all over me but I there was no way that I was going to let him fuck me.

Somehow I managed to survive not getting fucked by his cock but his fingers certainly gave me enough pleasure to make me cum and he held me up when my knees started to buckle.

I was both pleased and not pleased when Donna interrupted the man’s attempts to make me cum again. She told me that her and Daisy were leaving and I could stay or go with them. I chose to go and we went to the manager’s office to get our money.

He gave us 3 special passes that would get us in anytime but told us that we’d have to be naked to use them. We took them then went to find our way to where we hoped our driver and people carrier, and our clothes would still be. Thankfully, we found them, the driver being fast asleep. He quickly woke up when he realised that we were still naked.

We put our clothes on during the journey back to San Antonio where he was kind enough to drop us outside our hotels.

As I put my door key on the table on the balcony then got ready for bed, I looked at the clock and saw that I’d be lucky to get 4 hours sleep before, hopefully, one of my neighbours would creep in to wake me up in a pleasant way.

DAY 07 – The first day of my ‘enslavement’


It was Luke that I saw shortly after I felt his load of warm cum being deposited deep inside me when I woke up. I was pleased to realise that he’d started fucking me bare back.

“Morning Master.” I said, “How long is it before we need to leave to pickup the Jeep?”

“About an hour sex slave.”

“Good, I’ve got time to get ready and have some breakfast, I’m starving. When I’m getting breakfast would you 3 pick out the clothes that you want me to wear and take with me, and put that big bottle of sunblock with them please?”

“Sure, but don’t expect there to be many clothes.”

“Good, I want my naked body to be seen by thousands today.”

“We’ll do our best to make that happen slave.”

I squeezed Luke’s soft cock as I got off the bed and walked to the bathroom, feeling his cum start to seep out of me and creep down my inner thighs. It’s a feeling that John left me with a few times and I have to say that I think it’s a really sexy feeling. I wondered if I could get one of the boys to cover my face with their cum and if I’d get the same feeling walking around in public with it creeping down my face and going all hard and crusty.

I took extra special care to make sure that I was very smooth everywhere below my neck then I rinsed off, got dried and put lotion and perfume everywhere. I really wanted to smell nice for the guys.

There were a couple of G-strings and bralettes on my bed and I was pleased to see that none of them had any material between the strings. One of the G-strings was one that I had made, the string that goes from front to back splits into 2 as it goes over my clit causing the 2 bits of string to squeeze my clit and push it out. With the strings disappearing between my labia it makes my clit protrude like a little cock. I wondered if Luke realised that.

I quickly wrapped a half sarong around my waist and hurried off to get some breakfast.

“Have you got one of those that is more see-through” Will asked as I was greeted in my room by the 3 guys.

“In my case.” I said as I unfastened the half sarong and threw it on the bed then went to clean my teeth.

“Put these on Em.” Will said when I emerged from the bathroom.

There was a totally see-through half sarong and a bralette with no material. I smiled and replied,

“As much as that, I thought that you 3 wanted to show-off your sex slave.”

“Later Em,” Harry replied, “those are to get you to the Jeep, once we’re in it they will come off.”

“Good, have you remembered the towel for me to sit on, I’m assuming that all 3 of you will be filling my pussy and it will leak out.”

“Yes, and your sunblock is in the bag.”

“My phone? I need to send John some photos of what he’s missing.”

“Got it.” Luke said, then added, “I like the pigtails touch, it makes you look even younger.”

“Thank you Luke, now what are we waiting for?”

Within a minute or so, the 4 of us were going down the stairs and out onto the street, the security guard giving us a bit of a strange look. As we walked down the street I figured that maybe we did look a bit odd, 3 guys in shorts and T shirts, all towering above the 1 nearly naked tiny girl that to a lot of people was looking about 10 years younger than she actually was.

“Maybe she’s their little sister? Maybe she’s refusing to wear normal clothes? Maybe they won’t let her wear normal clothes?” Were some of the thoughts that ran through my mind as we walked.

“Walk in front of us Em.” Will said, “I want to see that cute little ass of yours.”

I ran to get in front of them then walked swaying my butt from side to side.

It didn’t take us long to get to the hire place and the Jeep was out front waiting for us. The 3 guys went inside while I climbed into the driver’s seat and looked around it. It felt good but I wasn’t envious of the guys, I was there to have fun and show off my body, not have fun driving.

The guys soon emerged along with the hire place guy, and started going round the Jeep looking for damage. I climbed into the back and sat behind the driver’s seat. I didn’t want to distract the driver.

When Harry was stood beside me he whispered,

“Take the clothes off.”

I did, much to the surprise of the hire place guy who kept looking over to me.

A couple of minutes later, Luke jumped into the driver’s seat and Will into the seat next to him. That left Harry to climb in next to me. I smiled as he looked over to me, then down to my tits and bare belly.

“Seat belts on guys.” Luke said loudly.

“Relax Harry,” I said, “I can still get my mouth to your cock.”

And I did, not 5 minutes later my head was bouncing up and down on his cock. When he’d shot his load into my mouth I sat up, turned to him and opened my mouth to show him his seed. He smiled then told me to swallow it.

After I settled back into my seat I asked Luke where we were going.

“Well Emily, we’ve decided to drive up the west coast and round the northern coast a little.” Harry replied, maybe because there was quite a bit of traffic and wind noise.

“And where are you intending to stop?”

“Anywhere that we fancy.”

Just as he was saying that Luke turned off the main road and we were soon in a car park near a little beach. There was an old man collecting the parking fee that Luke paid, the man not even looking at me.

“Everyone out.” Luke said as the Jeep came to a halt where he was going to leave it.

“So who’s going to put my sunblock on then?” I asked, the heat from the sun starting to really warm me up.

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