The Diss

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College kids on vacation explore an old town, and each other.
5.8k words
4.74
20k
19

Part 1 of the 3 part series

Updated 06/08/2023
Created 09/02/2017
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This is a slow start to a series, but it will start heating quickly in the next chapters. i would love to hear from female readers if the fact that the story is written in the first person, from the point of view of a man, is preventing them from connecting with the story or the characters.

*

"I can't believe it's almost the end of the semester! I thought I would've had more of an adventure by now," She said, approaching us.

She was smiling, half teasing, half coy, her eyes locked on Jonathan, waiting for a reply to her obvious come on. I was standing right there, talking to Jonathan, having already been in a conversation with Jonathan, before she had walked up to us. To this day I'm not even sure she had noticed that I had been standing there, talking to fucking Jonathan.

Jonathan turned his head slightly to look at her, his perfectly cut hair falling stylishly across his perfect tanned face. He looked like the poster boy for rich preppy New Englander in his polo shirt and white shorts, which is exactly what he was.

Without missing a beat, utterly polite, he said:

"Well you should go into town with Richard here, I'm sure he could show you the sights."

He turned to me before continuing,"you'll show her around, right, you're not doing anything today?"

And then he turned and left, leaving the crestfallen girl standing there, mortified and embarrassed.

I too stood there, uncomfortable in the sudden silence.

To break the silence, I mentioned to the bus stop nearby.

"I was going to go into town. With the bus. If you want to come." I managed to say.

"I...I think I have..." she mumbled.

"I promise it'll be more fun than staying here and dealing with them," I said, motioning towards a gaggle of girls who were looking at us.

The girl shuddered and grabbed me by the elbow, pushing me towards the old gate and the nearby bus stop.

"Let's get out of here. But the bus? What' s wrong with you, don't you have a car?"

No, I didn't have a car. I had a bus pass though, and when the bright yellow bus trundled up to the stop I guided her up the stairs and into a pair of empty seat.

She sat and stared out the window, trying not to touch anything. The thing is, she was quite pretty, and I became very aware that I was sitting next to this perky blonde barely covered by a summer dress. And she was going to spend the afternoon with me. I suddenly became nervous.

We were both on a semester abroad in a small coastal town in Spain. Our university had arranged for classes to be held in an old monastery on the edge of a small tourist town. With room and board on the premises, most of the students had simply stayed put and rarely left the compound, more interested in the petty intrigues of who had done what to whom. Apart for drives to the local beach in rented SUVs that daddy had paid for, the student body was shockingly inert.

Kelly. That was her name. We were both in English Lit class.

I briefly glanced out the window. The sky was a perfect blue, the Mediterranean a slightly darker blue in the distance, the view cut by golden hills capped in green olive trees. As the little bus rumbled down the narrow roads that snaked through the picturesque hills that overlooked the small town, I gathered up my courage.

"So Kelly," I said, "do you know what you want to do in town?"

"No. I don't care," she replied, sullen.

I will be the first to say that I was an introvert. I was the skinny geek that no one talks to because I was not rich enough, or buff enough, and deep down I despised these rich spoiled brats who inherited a chance at an education my parents had sweated for, that I had sweated for with part-time gigs while studying.

She was sitting there with her hair perfectly done, in a dress that probably cost a ridiculous amount, a little purse clutched in her soft and manicured hands. I was in my board shorts and a T-shirt with Darth Vader walking an AT-AT printed on it.

And yet, from the height of my nerd-dom, I had the rare moment of clarity. This girl I was so ready to both despise and masturbate furiously to once this day was over, this poor girl was heart-broken and humiliated.

Jonathan was dick. Jonathan had dumped her in my lap. Blessed be Jonathan.

I resolved to cheer her up in the only way I knew. I took her to the library.

Our little bus had made its way through the streets of the touristy part of the town, past bars and shops and internet cafes that catered to the Anglo crowd which flooded the beaches every summer. We stayed on as the bus revved up and made the slow crawl up to the Old Town, the part of the city which jutted out into the sea on a small peninsula. The bus stopped under the towering walls that surrounded the Old Town. There was no going further. The streets behind the walls had not been made for modern vehicles.

"Come on," I said, and got off the bus.

She followed, blinking in the harsh afternoon sun.

We walked through the tall gate of the Old Town and onto the cobblestone streets within. I guided her past the tacky tourist shops selling tin swords and painted jugs made in China. The air was slightly cooler here, in the shade of the stone houses that towered over us. Brightly painted shutters contrasted with the smooth whiteness of the old homes, the blue sky a distant strip of light.

I was worried that she would tire soon, but she followed easily as we climbed up through the city. The whole place was on a hill, so we were always going up or down. The only things level in this place were the steps. I remembered that athletics were quite important at our University. Chances were that she was in better shape than I was.

A small plaza opened up in front of us, a tiny church taking a whole side. Opposite the church was a palace, a private home of some long dead noble. A cafe and a bar shared the rest of the plaza. I guided her towards the broad doors of the palace, for it had been turned into my favorite place in the whole town: the library.

Not just any library. Kelly couldn't help but gasp a bit as we pushed through the door. The tall ceilings were painted with cherubs and gods, the trims gilded. Chandeliers hung from the ceiling. The afternoon sun shone though stained glass windows the size of a man. Room after room was filled with bookshelves and thick oak tables on which books were artfully stacked. I lead her up a flight of stairs, past small chambers where chairs and sofas had been placed, where the silent locals were happily reading. Up another flight of stairs, smaller this one, to more rooms that had been converted in to reading rooms. The higher we went the smaller the rooms, old servants quarters now housing a collection of faded sci-fi novels (my favorite). There was a small section of books in various languages, but I liked to browse the strange old books.

I waved hello to a smiling old lady, who returned my wave and cheerfully said hello. We politely asked about each other's health, in Spanish. She smiled at Kelly and looked at me warmly, an amused glint in her eye. She was my favorite librarian here. I came here a lot.

"You speak spanish?" asked Kelly.

"A little," I replied.

Truth was, I liked to learn, and I wasn't going to spend a month in a foreign country without cracking open a language book. Kelly seemed a little impressed.

As soon as the librarian left us alone, I grabbed Kelly's hand and pulled her down a short hallway which ended with a stout wooden door with a clear "no entry" sign tacked to it. I pushed it open and pulled Kelly through, quickly shutting the door behind her.

"What are you doing?" she exclaimed, looking slightly horrified.

"This way," I whispered, her hand still in mine.

We were now in a tiny spiral staircase, so old that the stone steps had been worn down by hundreds of years of use. Thin windows let air and light in. I led her up the stairs, trying to be quiet. Kelly followed without resistance, silent as well.

The staircase punched through the floor of a tiny room, barely bigger than the stairs, capped by an old roof framed in wood. If you reached up you could touch the old tiles that protected us from the sun. The room was really an extension of the stairs, a ring of wooden boards a few feet wide that extended the stone rim of the top of the stairs. All along the walls were windows, or square holes in the walls really, since they were open to the elements. And before us, through those windows, was the city, and beyond it the sea. We were at one of the highest point in the Old Town.

Kelly had a big grin on her face.

"This is incredible!" she whispered.

"Right?" I said, proud.

Kelly let go of my hand, which I only now realized I was holding. She walked around the room, staring out the windows to better see the view.

I sat on the steps and watched her.

Her legs were long and tanned, barely hid by her thin dress which fell at mid-thigh.She was wearing a soft and layered sun dress, green and blues and golden patterns interwoven together. From my seated position I could see frightfully far up that dress, especially when she leaned out the windows. Thighs, golden thighs...

From what I could see she was willowy, with small breasts that barely filled the top of her dress. Her blonde hair fell to her shoulders, straight and light, framing her long slender neck and oval face. She lacked the sharpness that I had seen in the other girls in her clique, her smile too broad and open to carry the permanent sneer that graced the others. Her eyes were green, I noticed. And she was looking at me.

"Now what?" she whispered.

"What do you mean?" I asked, stupidly.

"I was promised an adventure," she replied, a determined look on her face.

Later I realized that she was on a mission to prove stupid Jonathan wrong, that she didn't need him, that she would have the best time ever without his stupid face in the picture.

"Let's go back down," I said, since I was a moron.

We snuck back down, making our way out of the library. We spent the next few hours exploring the castle that topped the rocky outgrowth the Old Town was built on. From time to time Kelly's hand would find her way in mine as we climbed steep staircases and hopped over old fortifications. Just as naturally she would let go. And we spoke, we chatted about this and that, about the books we had read for the course and the ones we read for pleasure. It was a lovely afternoon, if I may say so myself.

We were on the far side of the castle wall, overlooking the open sea, when I had an idea.

"Do you want to go swimming?" I asked Kelly.

She looked over the city towards the town beach crowded with tourists.

"Meh," she replied.

I grinned.

"This way," I said, and grabbed her hand.

She followed, leaving her hand in mine.

I led her down a series of steep and narrow stairs that took us to a wide room under the battlements. Half the room was bare rock, with only the ceiling and a curving arc of wall made of masonry. A whole side of the room was open to the sea, a sheer cliff awaiting anyone getting too close. A row of rusted metal rings were attached to the back wall.

"This was the dungeon," I said, " Nice view."

Kelly held my hand a little tighter as we crossed the space and headed for an old metal gate that barred a small doorway. Beyond the gate was the open cliff side. The gate was locked, but I whipped out my ID card and easily pried the shaft back, opening the door.

"Oh my God! You are such a scofflaw!" she exclaimed, her eyes big but a smile growing on her lips.

"I prefer the term scalliwag" I replied.

"Are we going to get in trouble?" she asked.

"Only if we are caught. Let's go!" I exclaimed.

She scurried past me and onto the open air landing carved out of the cliff. I shut the gate behind us.

A steep staircase carved out of the cliffside led from our little perch all the way down to the sea. I lead the way, recommending that she kept one hand on the cliff wall. The other side was a steep drop to the sea below.

The staircase very quickly took a turn into the scrags of the cliff, taking us away from the sheer drop. The way was actually quite safe, apart from that initial dozen steps at the top. The staircase instead followed the natural contours of the rocky coast. Here and there I helped Kelly climb down over a boulder that interrupted the way. Her sandals were not really appropriate climbing gear, so I would turn and hold my arms up as she scrambled down.

Her dress, pulled up, revealed more of her long tanned legs. I caught a flash of pale pink, her underwear, more than once.

We finally made it to the bottom, where the stairs dissolved into the rock face as the cliff itself turned into a small covered beach. A cave had been cut into the cliff by the waves, creating a small sandy alcove. I jumped down onto the sand.

"Voila!" I exclaimed.

Kelly clambered down, eyes wide.

"This is so cool!" she said.

"Your private beach. Care for a swim?" I asked.

She put her hands on her hips.

"I'm not going skinny dipping in broad daylight," she stated firmly.

"Just go in your underwear, it's like a bathing suit," I replied, trying to sound casual.

I had noticed that she objected to going skinny dipping in daylight. Not with me. I clung to that little detail.

"Then it'll get wet," she pouted, frustrated.

I pulled my shirt off and kicked off my Keds.

"I'm going in!" I said, and ran for the water, diving in.

The water was cool and perfect. I surfaced a dozen feet away from the little beach and floated on my back, looking at Kelly.

She was taking her dress off and laying it carefully on a rock. At first I thought she was naked, but quickly saw that she was wearing a pale pink set of matching underwear. She looked stunning to me. She was an athlete, no doubt, probably soccer. Her thighs were strong, her ass tight and round, completely uncovered by her thong underwear. Her waist was not narrow, instead it was solid, with a hint of a six pack. Her breasts, small and firm in her pink bra, stood high on her chest.

She ran to the water and dove in.

We swam and splashed each other for a while, giggling and laughing. I was desperately trying to hide the semi boner that was tenting my shorts, swimming under water as much as possible. Though when under I could open my eyes and see her mostly naked shape, which didn't help.

Finally she climbed up on one of the boulders that were jutting out of the sea. I treaded water near her, looking. She laid on her back, as if to sun herself, her feet aimed at me. She propped her head up on her folded arm to look at me.

"Do we have to climb up those stairs to get out of here?" she asked.

I didn't answer at first. My eyes were locked on the gusset of her panties. The thin silky fabric was plastered against every fold of her sex, revealing her in intimate detail. I could tell she was shaved smooth, not a hair pushing against the fabric. Her pussy was a thin mound of flesh, split into soft folds, capped by the rising hood of her clit.

I ducked under the water to force myself to break my stare. My erection was hard, tight, almost painful against my shorts.

When I surfaced she was in the same position, still looking at me.

"We can walk on the rocks," I sputtered,"there's a small path that goes all the way around." Kelly rolled on to her side, resting her head on her arm. Her butt was now aimed at me, her thong underwear doing nothing to hide the firm globes of her ass.

"We should probably get going. Are you going to come out?" she said, looking right at me. A small smile creeped onto her lips.

"In a sec," I replied, and dove back under, putting as much distance and cool water between my erection and her charms.

By the time I had cooled off Kelly had swam back to the little beach. As I walked up to her she was shaking water off of her limbs and squeezing water out of her hair.

"In this heat we'll be dried pretty quick," I commented as I pulled on my T-shirt.

"Turn around," she told me.

"Why?" I asked.

"Just turn around! Face the sea," she insisted.

I did so, pulling on my sneakers in the meantime.

"Okay, your good now," she stated.

I turned around to see that she had put her dress on. I failed to see why I had to turn around for that. Then I spotted the wadded up pink satin bundle she was holding clutched in her hand. She saw my look.

"I'm not wearing wet stuff all day," she said, as if stating the obvious.

Dammit, my erection was returning.

I spent a split second trying to see through the fabric of her dress and catch a glimpse of her naked form, but could feel a blush coming onto my face. So I turned away, as casually as possible, and pointed towards a gap in the cavern wall.

"That's where we go," I said, and lead the way.

We walked along the edge of the small rocky peninsula that supported the Old Town and its castle. The path was narrow and uneven, often consisting only of boulders washed by the small Mediterranean waves, forcing us to hop from one to the next. We often held hand as we did so, me pretending to be a gentleman, and her pretending that she needed the help. There was a lot of giggling and laughter. Kelly was having fun, which made me happy.

The final stretch of the hike was easier as the land flattened. We were approaching the town from the other side of the touristy part. Locals lived around here, and locals swam around here. We started passing small groups of people sunbathing on the rocks and children diving into the water. Most of the women we passed were topless, which caught my attention. Kelly smirked at my attempts to discreetly memorize every square inch of boob we passed.

We passed a woman who was naked, up on a rock a dozen feet or so above us. She was in her mid-thirties or so, pretty, dark haired, voluptuous, with wide hips and heavy breasts. She was reading a book, one leg raised, revealing a thick triangle of black pubic hair, the tangles split by thick and red inner lips that poked through. She looked incredibly feminine, womanly. Kelly, pale and small compared to her, suddenly looked girlish. I was hit with the power of that woman. I wanted to dive into the Y of her legs, dive into that bush, devour her, paw at her full breasts, suckle the wine-dark nipples. And yet knew with utter certainty that my efforts would be inadequate, that there was nothing I could do that this woman couldn't take and ask for more.

I silently devoted myself to a life long study of the Tantric arts (I'm pretty sure I saw a book about it in the library) so that one day I could face such a woman with confidence.

We made it onto the pier where small fishing boats were tied. Kelly slipped her hand into mine as we crossed the small town. The sun was about to set, lights were being lit, tables set for the dinner service in the small restaurants that lined the sea-side road.

"Are you hungry?" I asked Kelly.

"Starving," she replied.

By then we had rounded the small peninsula. To our right was the Old Town, to the left was the touristy part of town.

"Where to?" asked Kelly, "my treat for showing me around."

"In that case, there's a little place right near the library that's perfect," I said.

"Oh my Gawd!" exclaimed Kelly, "we have to go all the way back up there? Whyyyyyy..." she exclaimed with an exaggerated cry.

"Because it's better! Come on" I said, pulling on her hand.

We made it up the hill fairly quickly, driven by hunger. We arrived at the small plaza the flanked the library as the sun was about to set. The small restaurant I was aiming for was all lit up with small candles, looking very romantic. If there was a place to make my move, this was it.

But Kelly had other ideas.

"The library is still open! Come on," she said, pulling me towards it.

I followed, confused.

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