Riley Takes a Year Out Pt. 02

Story Info
Tomboy decided to take a year out from her education.
9.9k words
4.61
10.1k
18

Part 2 of the 3 part series

Updated 06/11/2023
Created 12/21/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When I woke up the sun was bright and it was already getting quite warm. As I reached for the bottle of water I started thinking about the previous evening. I remembered walking around wearing my boob tube as a skirt and that it was so short that my slit and clit were on display most of the evening. Then there was the two men called Dave who had offered me a job at their strip club. I thought about becoming a stripper and again decided that I wasn't ready for that, maybe one day.

I went out onto the balcony to retrieve my towel and just stood there watching the people on the street below, some wearing what looked like travelling clothes pulling suitcases, some looking like they were going to the beach for the day and some looking like locals.

I again saw a couple of people looking up at me but I just didn't care that they were seeing all of my naked body but after a couple of minutes I went back in to get ready for another job hunting day.

I wore a proper skirt and a T-shirt, I'd considered a G-string but decided against it hoping that the air circulating around my pussy would keep it dry. I still couldn't understand why it was wet ninety nine percent of the time. Fifty percent I could understand because I was feeling horny more than I ever had done in the past.

Anyway, as I went downstairs I saw that Catalina had been replaced by a man who looked to be in his thirties.

"Ola." I said as I walked to the front door.

My first stop was the locker shop to retrieve my burner phone that dad had insisted that I take with me. It was the same young man and this time instead of bending at the waist to get in my locker I squat down facing him knowing that my short skirt would not be hiding my pussy. I smiled as I thought about him staring at my clit that definitely would be sticking down and very visible.

I'd seen a Telefonica sign in a couple of shop windows the day before so I went to the nearest one, bought a SIM card and topped it up. Now I could leave a phone number with prospective employers. I went to a cheap looking cafe and got a coffee and pastry for my breakfast. As I was waiting I sent a text message to mum and dad telling them that I'd arrived okay and was out job hunting. I didn't tell them that I'd already been offered a job as a stripper.

Suitably topped up I started job hunting again. When I passed a shop that sold stationery I went in and bought some little cards. Outside sat on a wall I wrote my name and new phone number on half a dozen of them ready to hand out if the opportunity arose.

As I sat on that wall I realised that anyone who looked would be able to see up my short skirt and see my pussy. That fact got me tingling and feeling slightly horny again. For the next five minutes I kept telling myself to stop it, that I was looking for a job. It worked a bit.

By late afternoon I'd asked in six bars and five eating places, and left four cards, but I hadn't got a job. I found myself close to the beach so I went and lay on the sand for a rest.

It was starting to get dark when I woke up and discovered that my right hand was on my pussy. I wondered if I'd been frigging myself in my sleep.

When I got back to my hotel I discovered that Catalina was back on duty. Whilst I'd been walking around I'd had an idea but lacked the tool to implement it.

"Catalina, would you have a large pair of scissors that I could borrow?" I asked after the initial greetings.

As she looked for some we made small talk and I noticed that her eyes were looking at mine this time. As I went up the stairs I wondered if Catalina was a lesbian or bi, she had been staring at my slit and clit quite a bit, and in a couple of hours she would have another opportunity to do that.

I stripped and had a refreshing shower then took the scissors and my denim miniskirt (mini by English standards, long by Ibiza standards), sat on one of the chairs on the balcony and, still naked I got to work shortening the skirt. On an impulse I also cut off the waist band so that the only thing holding it up would be the two studs. Then I started fraying the top and bottom hem to get rid of that just cut look.

When I was finished I held it up to look at it and immediately thought that it was now very short, it looked to be well less than twenty centimetres. I giggled and felt my pussy get wet knowing that I would probably be showing as much as I had in the tube top, perhaps more.

Satisfied with my work I tried the skirt on while still out on the balcony. Well, when I pulled it up and fastened the two studs the skirt was only lightly resting on my hips, one tug and it would be down. When I unfastened just the top stud the skirt hit the ground. Then I pulled it back up and fastened the stud. It felt loose on me but I could live with that.

I went inside, looked in the mirror and gave a little gasp,

"Oh my gawd, I think that I cut a bit too much off."

I could see the top of my slit and at least two centimetres of my pubis above it. I got that tingling feeling again and I felt my heart speed up. I turned around and could see the parallel to the ground cracks at the bottom of my butt.

"Liveable," I thought, "so how did I get the front shorter than the back?"

I took it off and compared the front to the back and the front was definitely shorter.

"Oh well, I guess that some people are in for a surprise, I hope they like what they see as much as I do."

I left the skirt on the bed and went outside to get the last of the sun for the day. As I sat there laying back on the chair trying to expose as much skin as I could I again tried to work out how I had gone from an almost shy girl to one who got great pleasure out of letting people see her naked. Was it because I was a late developer, was it because I had started having sex, was it because my Leaver's Ball dress was so thin that I couldn't wear a bra or proper knickers, was it because my mum told me to leave off my bra and wear a G-string instead of proper knickers, or what?

After ten minutes of trying to figure it out I gave up, I didn't really need to know, all I did need to know was that showing my body made me feel really good. What's more fucking my mates was really good as well.

When the sun cast a shadow over my side of the hotel I went inside and looked at the tops that I'd brought with me. I was really glad that I had only brought thin ones, even the tube top that was now a skirt was thin.

Then I looked at the two bikinis that I'd brought. The fabric was thin but they were both lined so I set to and cut the linings out of the tops and the bottoms, I wanted then to cling to me like paint.

Next I looked at the three sun dresses hanging in the wardrobe. I tried each of them on again and was reasonably satisfied with them so back into the wardrobe they went although I wasn't sure if there would be a time when I wanted to wear a dress.

Finally it was the other skirts, I remembered that I'd left one in my locker so the two more that I had in the hotel became targets for the scissors. One was 'A' line and very light but when I tried it on again I decided that it was too long for the new me so the scissors got busy. A few minutes later I tried it on again and was satisfied. I felt like I was only wearing a belt and when I looked in the mirror I just knew that the slightest breeze would blow it up revealing my lack of knickers.

The other skirt was a bit more conservative. It had an elasticated waist with nothing to indicate a front or a back. Again the scissors got busy by this time instead of cutting the hem parallel to the waist I cut diagonally and when I tried it on the shorter part went nearly to my hip. I giggled and spun it round ninety degrees and saw that my butt was fully covered but the whole of my pubis and a fair bit of my stomach was visible in the mirror. I could definitely have some fun wearing that around town.

Clearing up the mess that I'd made I felt proud of myself for being so brave but at the same time I thought that I was crazy. If I had worn any of those skirts in England without any knickers I would have been arrested as soon as I left my house but here I was intending to wear skirts that showed my slit and clit all the time.

I sat back on my bed and thought that I really was crazy but I giggled as my right hand got busy between my legs.

When I was returning to normal, if anything that I had done in the last couple of hours could be called normal, my stomach started to tell me to put some food in it so I put on the denim 'belt', a halter top that was small when I last wore it some six or seven years ago, my sandals, picked up my bag and the scissors and left my room.

Catalina must have heard my sandals on the marble floor because she was looking at me as I went down the stairs, and when I turned to go to her I saw a broad grin on her face.

"Wow Riley, you look amazing."

"Hey," I replied looking to see where her eyes were looking. And I felt a tingle in my pussy when I saw that she was looking at my slit and clit.

"Why had my clit grown in the last few days?" I thought then rationalised that it couldn't have, but it certainly felt like it had. Maybe the daylight and the sun had something to do with it.

"Muchas gracias Catalina, hicieron el trabajo simplemente genial."

"Wow Riley, your Spanish is good."

"Nowhere near as good as your English Catalina, I now have skirts that are better suited for this climate, thank you."

"You are welcome Riley, have a nice night."

"It will be a cheap one as I have to hold on to my money for when I leave here."

"Something will turn up Riley."

"Yes, I could always become a stripper."

"Stripping is a well paid job Riley, and it's not exactly hard work."

"That may be true but I want to see if I can find something else first."

"Okay, you have a pleasant evening Riley."

"Thank you Catalina."

I went outside and immediately got surprised by two happy girls walking right passed me and making quite a bit of noise. The thing was they were topless and wearing just a thong and a few stickers on their bodies.

As I watched them walking into the distance I wondered where they got the stickers, something else to look for as I go around the bars and shops.

As I walked in the same direction of the two girls I realised that I was actually thinking about wearing some stickers instead of a top.

"My slutty side strikes again." I thought.

As I walked towards the area that has the most cafes I was reminded that my slit and clit were on display by a couple of 'happy' young men who told me that they could see my clit. That surprised me a bit because the street lighting wasn't that bright were I was at that time and, although I knew that my clit was bigger than it had been a week ago, I didn't think that it stuck out that much. I smiled to myself as I tried to work out how I could measure it and keep a record so that I could tell if it actually was still growing or it was just bigger because I was feeling horny all the time these days.

I found a little place that sold slices of pizza so I got some and a cola and sat out the front eating and watching all the people. After a while two young men came and sat at the other side of the table,

"What can we do to cheer you up love, you look depressed." One of them said.

I just looked up and stared at them.

"Come on gorgeous, give us a smile." The other guy said..

By then I'd weighed them up and decided that they were harmless, and not bad looking so I replied,

"I'm okay thanks, just having trouble finding a job."

Well that was it, both of them were soon telling me about them and cracking jokes and the small talk just kept going. Eventually Blake stood up and said,

"Leo and I are going for a drink, would you like to come with us Riley, we're buying."

I sat and pondered for a few seconds then replied,

"I haven't any money."

"I said that we're buying."

"Are you sure?"

"Stop pissing about Riley I'm thirsty, come on." Leo said.

I stood up and both Leo and Blake saw my skirt, or should I say my slit and clit.

"Bloody hell Riley," Blake said, "that's one hell of a skirt that you're nearly wearing."

"Like it do you?" I asked.

"Hell yeah." Leo replied.

As we walked towards the noisy bars Blake asked me if I knew what I was showing.

"I do, not complaining are you?"

"Hell no." Leo replied.

"Is it the fashion where you come from, to have your pussy on display all the time then Riley?" Blake asked.

"Not that I know of, but England isn't as warm as Ibiza."

"You're the first girl that I've seen in a skirt like that Riley." Leo said.

"Have you seen the topless or bottomless girls running around here?"

"A couple." Blake replied.

"Well a girl wearing a skirt like this shouldn't be a big deal then."

"It's not," Blake replied, "it was just a surprise."

"A nice surprise." Leo added.

We found a bar with a table outside and sat down, both guys opposite me and their eyes went straight to my pussy.

"You have both seen a pussy before haven't you?" I asked.

"Yeah, we're not virgins," Blake said, "but we're men and men are fixated with pussies."

"So I noticed, and for the record I'm not a virgin either and I recently discovered that I like men looking at my body."

As I was saying that two thing happened, firstly I seriously considered taking my top off and let them look at my tits and secondly a barman came and asked what we wanted to drink.

As the barman went to get us our drinks Leo said,

"So are you some sort of exhibitionist then Riley, because if you are you can strip naked for us you want."

"Actually, I'm starting to think that I am, I've decided to enter a wet T-shirt competition next week and I'm planning on going to the nude beaches as soon as I get myself organised."

"Let us know when and we'll come with you." Leo said.

I smiled then reached behind my neck and unfastened the halter top. Moving my hands back to the table my halter dropped off my tits and I could feel my hard nipples tingling and four eyes staring at them.

"Nice." Leo said..

"Very nice." Blake added.

I just sat there wondering both why the hell I had just done that, and that both my nipples and my clit were tingling something rotten.

The barman came back and put three beers on the table, not even looking at my exposed tits. This was something that Blake noticed and said,

"That guy didn't even look at you Riley."

"He's either seen thousands of naked girls or he's gay." Leo replied.

"I don't care." I replied as I took a deep breath and pushing my tits out, "I'm proud of these."

We spent the next hour or so with small talk and taking about the people passing who looked over to me. A few of them making comments that we just ignored except for Blake asking me if I minded them saying things like that.

"Not at all," I replied, "for them to even comment means that they liked what they saw and to me that's a compliment."

"Good attitude Riley." Blake said, "I think that you are right.

After another hour of so, and another couple of beers I stood up and said,

"How far away is your hotel guys?"

Leo nearly spluttered the last mouthful of beer that was was just going into his mouth, all over me and the empty chair next to me, then said,

"You want to come back to our hotel with us Riley?"

"Thanks for the invite Leo, yes please, and don't look so shocked or you'll lose those boners that's been looking uncomfortable for hours."

As soon as I stopped talking I thought,

"Wow Riley, that was unexpected."

However Blake was already getting to his feet so Leo and I did the same and we started walking, me with my bag and top in one hand and thinking how good it was to be walking along the street with my tits on display as well and my slit and clit.

Yes we got mainly guys looking at me, some girls as well. But I was feeling good and not at all embarrassed.

Leo and Blake managed to sneak me into their hotel and it was much better than mine was. By that time I was convinced that It was the beers that had got me there but I wasn't going to back out, I wanted to be fucked just as much as they wanted to fuck me. We were the only ones in the lift and when it set off up the first thing that I did was unfasten the studs on my skirt then pick it up off the floor.

Blake and Leo looked at the naked me in amazement then the lift pinged and stopped at the next floor.

"This isn't us." Leo said as the doors opened and a young couple got in, hesitating for a second when the saw the naked me looking at them with my hands by my sides.

The doors closed and we started going up again and I now had six male eyes and two female eyes staring at me. My clit and nipples hadn't throbbed that much since I got naked behind the gym at school.

Blake and Leo got out at their floor and I followed them for a few steps until I ran passed them to let them look at my bare butt as we walked.

Room door open and me inside I dropped my clothes and bag on the side, kicked my sandals off and went straight to the balcony where I put my hands on the railing and stepped back so that my butt was sticking out at the two, slightly shocked young men.

"Will one of you stick something inside me please?" I asked without looking back.

One minute later I felt a cock touch my dripping pussy.

"Ooooooohhhhhhhh that's nice." I said as the cock went right in then slowly started fucking me.

It was then that I heard a noise from the next room's balcony. I turned my head and saw a young man and a girl both looking at me. I gave them a little wave then continued to enjoy the fucking.

It probably took around a minute before I felt the cock tense and stop then it pulsed as warm sperm started to fill me. My orgasm had started to build but I wasn't there and when the cock pulled out of me I needed the other cock to hopefully finish me off.

"Next." I loudly said as I glanced over to the next balcony and saw our two voyeurs still watching.

The second cock entered me and I let out another long sigh. Fortunately that cock's thrusting in and out lasted long enough to finish me off and we both orgasmed within seconds. As the cock withered and slipped out I stood up straight and saw that it was Blake stood behind me.

"Round two coming up," I said and took Blake's hand and led him inside then pushed him down onto the bed not far from Leo who looked like he was still recovering. I knelt on the bed between them and my hands went to each of their cocks then I stopped.

"Wait, I've got a better idea."

I got up and turned round then knelt with my knees either side of Blake's shoulders.

"I've always wanted to try this." I said as I bend over, lowered my face to his cock and lowered my pussy to Blake's mouth.

"Don't worry Leo," I said, "we'll do this in a minute."

I practised my recently acquired blowjob skills and Blake took the hint and started to lick my pussy. It was nice but I was sure that he hadn't had much, if not any experience of eating pussy before, but I couldn't complain, I was relatively new to blowjobs as well.

Leo was within arms reach and while I was blowing Blake my hand was wanking Leo's cock but that didn't last long because I somehow sensed that Blake was going to cum again so I sat up, shuffled down and impaled myself on his cock.

Blake lasted a bit longer than the first time and I managed to cum as well before I got off him and turned to Leo and said,

"As promised."

And I climbed on top of him and repeated what I had done with Blake, including Leo and me cumming again before collapsing on the bed between them.

After a few minutes of recovery I sat up and asked if I could use their bathroom where I cleaned up as much as I could then went back out to find both of them still flat on their backs with withered cocks hanging between their legs.