Emily’s First Solo Holiday

Hi, my name is Emily and this is what I did when I went on holiday on my own.

I’m 22 years old, slim 32A 23 30, with shoulder length strawberry blonde hair, 5 feet nothing tall. I’ve been told that I have a cute little bubbly butt. I’m an engineer who shares an apartment with 2 others, both men.

I was engaged to a really nice guy (not 1 of my room mates). The problem was that he started to get all possessive and prudish when I started buying clothes for the holiday. I was determined that I was going to get a great suntan but he wanted me to wear bikinis that would have been fashionable in the 1950s. Not only that he refused to let me buy sundresses that were shorter than just above my knees; and when I said that I wasn’t going to take any bras with me I thought that his rage would blow the top of his head off.

Up until that bust-up John had been quite happy for me to wear short skirts and dresses and he loved looking down my tops and seeing my small titties. He’d also loved it when he took me out wearing a mini-dress, with nothing underneath, but for some weird reason the thought of me doing the same and wearing really skimpy bikinis on Ibiza where hundreds of thousands of girls would be wearing similar outfits just made him flip.

The end result was that I gave him his ring back and told him that the engagement was off, that I could never marry a man who was so prudish and controlling. Up until that night I’d really loved him and I could never imaging falling out of love so quick, but I did. To say that I was annoyed with him would be a gross understatement.

It was me who had booked the holiday so I had all the paperwork and I sure as hell wasn’t going to let him come with me.

It was 3 weeks before the holiday and I spent a fair bit of of those 3 weeks shopping for the skimpiest clothes that I could find. I planned to take lots of selfies with me wearing next to nothing, or even nothing, in public places and send them to him to show him what he had let slip through his hands.

As the day of departure got close I got more and more excited about the amount of flesh that I was going to show and the number of guys that I was going to have sex with. I also got more and more determined that I was going to have a really good and sexy time. I even took a little note book with me to write the names of my conquests.



My outfit to the airport consisted of a skater skirt that was so short that it just covers my butt and pussy when I’m stood straight, a see-through, sleeveless blouse that left a lot of my belly bare and tie fastened, and 6 inch heels. I carried a scarf that I could put round my neck and let it hang over my titties if I thought that it would be advisable to have my nipples covered.

The only underwear that I took with me were some thong knickers that I would wear as bikini bottoms. Half of the thongs have no material in them, just the strings so my bald, little girl’s pussy would be on display all the time. The other half of my thongs were see-through.

When I said my ‘little girl’s pussy’, I mean that that’s what it looks like because I have no inner labia and when my legs are not spread wide, all you can see is a slit. If I’m aroused my clit pokes out between my outer labia. All the boys that have seen it have told me that I look like a little girl, especially as I shave the whole area every morning. The other thing about my pussy is that when I do spread my legs wide my hole gapes open. John told my that a gynaecologist would need a speculum, although he had used one when I went for a check-up to get put on the pill.

Things got off to a great start when I got to the underground station to circumnavigate London to get to Gatwick airport. It was rush hour and I struggled a bit with my case. Going down the escalators wasn’t much fun but standing on the trains had their moments. I hadn’t really thought about having to travel on the underground, all my thoughts had been about the fun that I was going to have in Ibiza, but that all changed when the first hand slid up my bare thigh to my bare butt. The dense crowd on the train meant that men could grope me without me being able to see who the hands belonged to, I guess that they took my ultra short skirt as an invite and I wasn’t complaining, I just hadn’t expected the fun to start so soon.

Two separate hands found my pussy and both invaded my body. Unfortunately, neither of them managed to make me cum.

I had to change trains and go up an escalator to get to my next platform and the middle-aged man who followed me up must have thought that he’d died and gone to heaven.

I had a bit more fun on the escalators at Victoria station where I had to catch the Gatwick Express. On one escalator I looked back and down and saw a man looking up at me so I bent forward, pretending to check the luggage ticket on my case.

I managed to get a seat for the last leg of my journey but my skirt fell between my legs and I couldn’t be bothered to try to flash my pussy to any of the other travellers.

At the check-in I wore the scarf so as not to risk offending the middle-aged women who worked there. The scarf came off as I went through security and I caught one of the guards staring at my chest. I’d read about a woman getting thrown off a plane because of her see-through top so the scarf went back on as I boarded the plane.

Getting into my seat was ‘interesting’, I had a window seat and the other 2 of the set of 3 were occupied by 2 young men about my age. I had to climb over them and each of them had my tits right in front of their faces. If they’d looked lower, they would probably have seen my pussy as well, but something was distracting them.

As I fastened my seat belt I made sure that my skirt wasn’t covering much of my bare legs and I knew that my bald pubes were on display.

Both guys wanted to talk to me and I discovered that they too were going to San Antonio, but a different hotel. They talked constantly, probably using that as an excuse to look at my chest because their eyes sure as hell weren’t looking at my face.

In amongst their talking they asked me why I was on my own, so I told them a brief summary, I figured that I would never see them again so why not admit that I wanted to flash my goodies to everyone and fuck as many boys as I could? After I’d told them that they asked me what the name of my hotel was again. I smiled and told them.

Their staring as we talked made my dark brown nipples as hard as rocks and after a while they started throbbing. I think that the vibrations from the plane were causing my nipples to rub against my top a little and that was stimulating them as well.

My top certainly wasn’t rubbing my pussy so that wasn’t the reason why it was getting wet.

Once the seat belt lights went off I unfastened the belt and turned sideways a little so that I could talk to the guys without having to turn my head so much. That and the fact that it would give them a better view of my chest. As I’d decided to sit with one leg under me, they had a great view up my skirt, not that they could see much, but enough for one of them to ask me if I often didn’t wear knickers.

I lied and told them that I never wore knickers but that I’d brought a couple of thongs with me to wear when I couldn’t sunbathe in the nude. Having said that I lied, I was seriously thinking of stopping wearing knickers after the holiday. By then I would be extremely comfortable going without.

Just over half way through the 2.5 hour flight I decided to tease them some more and said that I needed to go to the toilet. They both offered to get up but I told them that I’d managed to climb over them before and that I could do it again.

I did it facing them again, and as I straddled each of their legs I ‘accidentally’ pulled my skirt up so that my pussy was exposed to them. This time they didn’t miss seeing me.

On the way back to my seat I had to climb over them again, but this time I did it with my back to them and as I straddled each of them I sat on their laps and ground my pussy onto the covered hard-ons for a couple of seconds. When I was back in my seat I looked at their trousers and saw the stains from my pussy juices. I smiled to myself.

Getting off the plane was ‘interesting’ as well. I put my scarf round my neck and covered my tits until I was going down the steps, then a gust of wind from another aircraft’s engines caught my skirt and inverted it. My natural instincts made my hand go to pull it down but I only had one hand free and as I was straightening my skirt my scarf blew up and away. Even if I’d wanted to cover my tits again I had nothing to cover them with.

As I stepped off the steps the wind blew again, but this time I resisted my natural instincts and just kept walking to the waiting bus with my skirt up around my waist. A few people on the bus were looking and when I got on, 2 men had big grins on their faces. I smiled at them as gravity took over from the wind.

The guard checking passports either didn’t realise that my top was see-through or just didn’t care. But that couldn’t be said about the young men waiting for their luggage at the carousel and I git hit upon quite a few times, although not many of them saw my face.

The coach driver never even looked at me as he loaded my case and a group of 3 girls came and sat near me. None of them commented on my top as they talked about the clubs that they were going to go to. I hadn’t got as far as thinking about clubs, possibly because it’s always been dark in the clubs that I’ve been to and I was there to be seen.

It was late afternoon when I checked into the hotel and was given a room on the second floor overlooking the pool and then the harbour. I stripped naked then went out onto the balcony to see what I could see. As I looked down and around a couple of young men by the pool shouted up to me and waved, so I waved back, wondering how much detail they could see.

I got out my phone and took another selfie of the whole on my naked body with the harbour in the background, then I sent it to John with the text,

‘amazing scenery.’

It may have been late afternoon but it was still quite hot and the sun had a while before it would go down so I decided to catch the last of the sun. When I’d checked into the hotel I’d seen a woman walking through reception carrying a towel and wearing only a bikini bottoms so I tipped my case out onto the bed and grabbed a thong, one with fine mesh material and quickly slipped it on. I put my sunglasses on, grabbed a towel, a bottle of sun-block and my room key, and headed for the stairs.

It felt so nice walking along that corridor and down the stairs wearing only the thong and I wondered how much nicer, daring, sexier, arousing it would be to be totally naked. I swore to myself that I was going to find out before too long.

I followed the signs to the pool and quickly found a lounger where I spread my towel and started rubbing sun-block on my arms. Before I’d even finished my arms 2 young men came over and offered to help me. I looked them up and down and decided that things could have been a lot worse then took them up on their offer.

“Lay on your stomach and we’ll do your back first.” One of them said.

I did, and it was more like having a massage as their hands went all over me. The hands went down my body and to my butt where they massaged me for a lot longer than was necessary.

Then they started on my feet and moved up my legs. As hands went up my thighs I automatically spread my legs and tried to feel if the thong was square on my pussy or if it had moved to one side revealing one of my labia. Unfortunately it felt like I was covered but that didn’t stop at least one of the hands touching my thin mesh covered pussy. I wondered how much the hands owner(s) could see.

“If you turn over we can do your front for you, what’s your name?”

“Emily, or just Em, and you are?” I said as I got to my feet to lay on my back.

“I’m Liam and the ugly one is Ben, nice to meet you Emily.”

When I was on my feet and with my back to them, I adjusted my thong and pulled it up at the front, I felt the material disappear between my lips. When I lay down I had a quick look and the thong had disappeared right up to the front of my slit. I smiled and said,

“Thank you guys, and please don’t miss anywhere.”

I hoped that they would take that as being the intended invitation to lotion my tits and pussy.

They did, with one of then knelt either side of me they rubbed the lotion into my tits, pulling, rolling and generally playing with my nipples. I could feel my thong string getting wetter and wetter.

When they moved down my body and started on my bald pussy I was in heaven. There were other people not that far away so I did my best to stifle my moans of pleasure as fingers from 2 hands pushed my thong to one side and finger fucked me and rubbed my clit.

It didn’t take long for them to be rewarded with my orgasm.

As I got my senses back I looked around and saw that we were being ignored. Either people hadn’t noticed what was going on, or they didn’t care. I was glad that it was an adults only hotel.

I straightened my thong then thanked the guys for their help. They, unsurprisingly, offered to help me out anytime that I wanted. I told them that I may well take them up on their offer.

The sun may not have been at its strongest at that time of the day but it was really nice lying there letting it start my all over tan. I didn’t know if it would be tanning my pussy through the mesh of the thong but it sure did feel nice. I couldn’t wait to find a beach where I could lay totally naked with my legs spread wide.

When the sun disappeared I returned to my room, walking through reception where no one batted an eyelid at me just wearing a thong. I decided that when I next went to the pool I would wear a ‘strings only’ thong.

Back in my room I put my belongings into the drawers and wardrobe then decided that what I was going to wear to go to get something to eat (I’d booked only bed and breakfast at the hotel) and then find a pub to tease a few guys and get them to buy me a few drinks.

I chose a skirt that I thought was really daring when I tried it on in the shop, it’s longer at the back than the front, the front being so short that I could see my slit in the mirror in front of me in the fitting room. One reason why I bought it was that I knew that it would piss-off John if we’d gone out with me wearing it. I also wanted to have my slit on display all the time as well.

To go with it I chose a crochet top that has holes in it, so big that huge areas of my skin was visible; and that included my nipples sticking through 2 of the holes.

I went and had a shower then brushed my hair, I’d already decided that make-up was something that I wouldn’t be using on my holiday. If people didn’t like the natural me then it was tough.

I went out onto my balcony to brush my hair and I met my neighbours on one side; 2 girls who were getting ready to go and hit the town. We got talking and none of us cared that they were just wearing thongs and me nothing.

They told me that they’d only been there a couple of days but they’d already found a few good bars and got laid.

When I told them that I was there on my own they asked me if I wanted to join them getting something to eat then going on a pub crawl.

I told them that that sounded great and we all finished getting ready.

“Come on round when you’re ready Emily, the door’s not locked.” Dani told me as I went back into my room to get dressed.

Once dressed, I got my little clutch bag and put 2 condoms from the box of 50 that I’d brought and checked that I had enough money and my room key in the bag.

“I like the skirt,” Dani said as I walked into their room, “you’ll have to tell me where you got it.”

“Nice top too,” Wren added.

“Both of you look great as well, your skirts barely cover your pussies. I bet that you’ll be flashing your goodies half the night as well.”

Both girls giggled.

We continued talking as both Dani and Wren took their thongs off then put a skirt and top on. Neither wore any underwear to go out.

“I bet that you get a lot of attention wearing that skirt.” Wren said as we went down the stairs to reception then out to the street.

It was still quite hot and there were lots of people walking around. The warm, gentle breeze tickled my pussy and nipples as we walked. I felt good.

No one took any notice of my exposed pussy and nipples, probably because it was dark and there were hundreds of scantily clad girls walking around.

We stopped at a cafe and, after looking at the menu, sat at a table outside then had a great meal. We talked all the time with me trying to find out where the good beaches were and how I could get to them. Unfortunately, Dani and Wren had only been to 1 beach, Cala Conta and they’d got there on a little boat from the harbour. Dani seemed to remember hearing someone say that there was a nudist part but they hadn’t seen it.

I decided that in the morning I’d go and ask about nudist beaches at reception.

After the cafe we headed for where Dani and Wren told me all the good bars were, and they were right. Great bars, great music, dancing in some of them and lots of men. It wasn’t long before we’d started dancing and been bought a drink by some guys who tried to hit on us.

It was way too early to decide if we wanted to go back to some blokes room for a fucking session so after a while we dumped the guys and moved to another bar.

My slit showing skirt attracted a couple of comments and when 1 young man said that I had a nice pussy, Dani lifted the front of her skirt and asked if he liked hers.

All 3 of us burst out laughing as the young man collided with someone sitting at a table in front of him because he was looking at us and not where he was going.

We had / did much the same in 3 more bars before Dani said,

“Time to decide who we want to fuck girls.”

I felt my pussy get wet as I looked around to see it there was anyone that I fancied.

We compared notes and ***********ed 3 guys who were trying to hit on some other girls. We went and stood next to them and when 1 of the other girls told them to piss off, they turned and saw us.

They were looking for a fuck and so were we so it didn’t take long before we were leaving the bar and heading to their hotel.

All 3 of them looked quite similar and all 3 had drunk about the same amount so I had no preference as to which one I wanted to fuck. As we walked one of them put his arm round my shoulder and found one of my nipples.

“Wow, that’s hard.” He said as he rolled it between 2 fingers.

I put my hand on his crotch and replied,

“Wow, that’s hard.”

Dani, Wren and me had all got naked just as soon as we entered the room and all 6 of us were fucking within minutes. My box of 50 condoms got the seal broken and 3 of them got used.

DAY 02


I was woken by the noise of a door banging and saw that dawn was approaching, I got up and woke Dani and Wren and we grabbed our things and crept out of the room. We got dressed in silence in the corridor then walked back to our hotel, comparing notes as we walked.

Back in my room I had a shower then went and sat on the balcony to feel the warm, fresh air and watch the early birds have their swim in the pool before going down for breakfast. I decided to start as I intended to go on, and put on just one of my beach cover-up dresses. I’d bought 5 of them, all different except for one thing, they are all see-through.

Then I went downstairs to the restaurant and was disappointed to find that there weren’t many people there. Then I remembered the time.

“Must come for breakfast later.” I thought as I went to the buffet to help myself.

There was man who nearly spilt the milk that he was trying to put on his cornflakes when he saw me and did a double take to see if my dress really was see-through and that I had nothing on under it.

Whilst I was sat eating I suddenly remembered that I hadn’t taken a selfie of me getting fucked the night before. I cursed myself and vowed to remember the next time.

On my way back to my room I stopped at reception and asked them where the best beaches were, specifically the nude beaches. The young woman told me that nudity is legally permitted on all of Ibiza’s beaches but all the naturists tended to congregate on certain ones. She gave me a map of the island and wrote the names of the beaches that the nudists go to, at the point where they are. She also added the bus numbers if I wanted to go by bus, telling me that the bus station was only about 300 metres away.

One of the beaches was at Cala Conta which Dani and Wren had been to and told me about, and as I left reception I decided to go there, Dani had told me that the boat journey was slow so I decided to try the bus. I also had to find out about the buses because the receptionist told me that the best of the beaches were down near the airport.

Deciding that I was going to go in the same, see-through dress and take a thong in my bag – just in case, I went and got the things that I’d need then set off. Before I left my room I listened to see if I could hear any evidence of life next door, but everything was silent, I guessed that they’d gone to bed.

When I went out onto the street I remembered seeing a shop that sold water and sandwiches so I went and got some before heading to where I was told the bus station was.

It was easy to find and I went to the kiosk to get a ticket and had to queue for a good 5 minutes. I guessed that that time of the day was busy with people wanting to go to wherever. Whist I was waiting I got a timetable and route map of the island so that I could plan my future expeditions.

I had to queue again to actually get on the bus, the driver ripping the tickets as we got on. I wondered if he’s say anything about my dress being see-through but he didn’t even look up.

On the bus it was different, all the seats were gone and, apart from wondering how long I’d have to stand, there were the people sitting either side of the aisle. One was a girl about 11 or 12 who just stared at my body through the dress. Another was a thirty something man with his female partner in the window seat. He’d seen what he could see and I was determined that before we got to Cala Conta he’d have had a great look at my slit.

In the seats behind then were 2 young men and a young man and his girlfriend. The 2 young men, well 1 of them, had seen my bare butt and I was going to show him my front before we got off. The young man was totally engrossed in his girl and I never found out if he saw me.

As the bus rumbled along my little tits were wobbling about and my nipples were rubbing on the material of the dress giving me a nice sensation. At one point the road must have been flatter because I got the chance to let go of the rail above me and swap my bag to the other shoulder. As I put it on I made sure to pull up my dress at the side and trap it under my bag. That gave my voyeurs a slightly better look at my butt and pussy.

A long straight stretch of road ended outside a cafe that was already quite busy. Everyone went off in different directions and I was left having to decide which way to go. I decided to follow a family going to the right, then work my way along the water’s edge to find some naked people.

The beaches were nice, but small and at first I thought that reception and Dani had got it wrong because I couldn’t see any more beaches, but I saw some people walking along the edge of the open area and decided to follow them.

Then I saw it, a smallish beach with quite a few naked people. It has a very steep set of steps down to it but that didn’t put me off and I started down then found a patch of sand to spend the day at. I kicked my sandals off then took my dress off leaving me totally naked. I felt really excited, it was my first time fully naked on a beach and my pussy was telling me that it loved it.

There was a Spanish looking man sat on a towel next to me and he had smiled at me when I stopped and put my bag down. He was about twice my age but looked quite friendly.

I spread my towel then got out my sunblock. I managed to cover nearly all of my body but I was struggling to get some on my back when I heard the man say, in perfect English,

“Would you like some help with that my dear?”

I looked round and decided that he looked harmless enough so I replied,

“Yes please, I can bend myself double but I never seem to be able to get to the middle of my back.”

The bending double part was true, I’d done aerobics and gymnastics at school and could easily bring my legs right over and put them behind my shoulders. I’d never thought about it before but I wondered if I could still do it, and if I could actually get to lick my own pussy. I got a little excited at that thought as the man told me to lay on my stomach.