A Day by the Pool

It was mid-March and the weather in Milan was colder and greyer than I was expecting. I mentioned this to my sexy, mature next door neighbour Daniella—the lady that I had been having a complicated affair with for the last three months—and she suggested that we get out of the city for a long weekend to find some sun.

A couple days later we found ourselves in a pair of sun loungers near a pool overlooking the ocean at a fancy resort on a small isolated Greek island. The place was amazing and, since it was still early in the season, there weren't many other tourists around.

Given my pasty white American skin, I was doing my best not to get skin cancer by hiding under a sun umbrella, whereas Daniella lay fully exposed to the sun next to me. Since we arrive yesterday, her skin had turned from a soft mature brown to a full golden Mediterranean bronze, and given that this was Greece, she insisted on tanning without her top on. I could almost see her nipples and areolas growing darker by the second.

As I was there trying not to stare at her breasts, a cool spring breeze blew in off the ocean and over the top of us. Instantly her nipples grew erect, standing a good centimetre or two in the air. In my red swim shorts, my cock gave an involuntary twinge and began to get hard. The sexually repressed American in me quickly looked around in fear half expecting some old woman with a goat to scream in horror at the growing bulge in my shorts. It must have be too early in the season for morality police to be out on patrol, for no one screamed. In fact, the only other people out at the pool were two much older German women, who were also topless, who clearly couldn't care less about the state of my erection. I turned my attention back to Daniella's breast.

The last three months with Daniella had been strange. First, I had to think of what I meant by the word 'with.' From the very beginning we both made it very clear that we weren't dating, seeing each other, or any other of those happy, couple euphemisms. I just got out of a bad divorce and still wasn't ready to start seeing other people, and Daniella was cool with that. And Daniella made it clear that she had other commitments and 'hobbies' that made seeing another person hard.

And then there was the sex. We had sex. Lots of sex. Good wholesome, knees trembling sex, but it was pretty clear from the first moment I found her tied to her bed with the naked guy knocked out cold on the floor next to her, that sexually she was in a different league than me. She had certain appetites that either I couldn't fill, or, at the very best, would kill me if I attempted to fill them. But to her credit, she never demanded that I fill them, so in a way it never became a problem.

Then there was the age difference. She was somewhere between 10 to 20 years older than me, depending on who she was talking to or what story she was telling. I suspect that it was closer to 20. However maybe because she was older, I never had that ego driven, hormonally induced, cave man response to dominate her. She was in charge and we both knew it, but she was a benevolent dictator. She never humiliated me. She always kept me involved in what ever see was doing. And I always got to cum as much as I want.

In short, yes, this is a fucked-up situation, but there was a part of my brain—or maybe my penis—that kept whispering, 'let's see where this goes.'

"Let's see where this goes," I mumbled to myself.

"Cosa?" Daniella asked in Italian before remember that I was crap at Italian and switched to English, "sorry, I was asleep. Did you say something?"

"I was just thinking of getting drink. Do you want one?"

Daniella sat up in her sun lounger and turned towards me. With one hand she readjusted her sunglasses and then soothed down her curly auburn hair. With her other hand she absentmindedly pulled at her still erect left nipple. "Yes please, you know what I like."

I stood up and started to turn towards the bar.

"Theo!" Daniella shouted to get my attention.

I spun around to see her smiling, "be careful at the bar. They may see your erection," as she pointed at the bulge in my shorts.

Like a horny teenage boy in swim class, I did my best to physically shove it back down which only made it worse. Eventually I snatched the beach towel from my sun lounger and was off. Ten minutes later I returned with our drinks. While I gone, she had moved both of our sunlounges under the big umbrella and was now sitting up, gazing out on the nearly empty pool.

"Here is your drink."

"Grazie," she smiled before grabbing the ice cold and sweating glass and took a drink. "Did they see your erection at the bar?" she asked casually.

"No, I don't think so. I played it cool."

"Too bad," she laughed, "later we should show them and maybe they will give us free drinks."

Sometime later, I was contemplating ordering a second drink when Daniella's phone pinged. With great reluctance, she flopped out a hand in my general direction and pointed towards her purse, "Can you hand me my phone?" I put down my drink, reached down and fished through her bag. Eventually found her phone and handed it to her, "here you go?"

A few swipes and clicks later, "Oh!" She said with surprise.

"What is it?" I asked.

Without saying a word, she handed me her phone. On the screen was a photo of a naked man from the waist down holding his exceptionally large cock in both hands. "Damn!" I said a little shocked before handing the phone back to her. "Is he a friend of yours?"

"He could be?" She squinted at her phone for a second before swapping out her fashionable dark Italian sunglasses out for her pair of reading glasses that made her look like a sexy, topless librarian. "It says that he is in the vicinity and looking to 'hook up'," she emphasised with a dismissive hand jester before putting her phone down.

The two of us sat in silence and watched as one of the older topless German ladies slowly swam on her back across the pool.

"Well," I began, "there doesn't seem to be much going on here today, it wouldn't hurt to message him back."

30 minutes later we were back in our hotel room, kissing on our bed when there came a knock at the door.

"That must be him," I said eagerly. Daniella stood up and did a little dance in place. She still wore her red bikini from the pool earlier and her horned rimed librarian glasses. "Give me your glasses."

"I wouldn't want him thinking I'm old," she whispered.

I took her glasses and put them on the dressing stand and took a seat in the corner of the room. I quickly crossed and uncrossed my legs and arms several times in various combinations trying to find the right posture of a guys about to watch his friend have sex with a stranger.

Daniella peeked through the peephole in the door, smiled and gave me a thumbs up. As seductively as she could, she swung the door open.

In the hallway stood a skinny Greek Boy in his early twenties with dark wavey hair and a short dark beard. He wore a blue hoodie with a football team logo on it and dark work slacks. He was only slightly taller than Daniella which put him quite a bit shorter than me. We both instantly recognised him from the night before. "Ah, the waiter from the hotel restaurant," we said in unison.

The Greek Boy instantly recognized us too, and for a nervous second he looked like he was about to run.

Daniella saw this too, so she reached out, grabbed his hand, quickly pulled him into our room and shut the door.

We knew that he spoke Italian from the night before, so Daniella waisted no time in introducing herself. She then turned to me and quickly introduced me as her 'friend' who likes to watch. He didn't like this, but she promised him that I wouldn't touch, which seemed to make it sort of okay.

They talked quickly for a minute more, much of which I couldn't make out. The Greek Boy still looked nervous as hell. I sat in the corner of the room, smiling and randomly nodding my head, in an attempt to put him at easy, however, I wasn't sure that this was working. As they spoke, I caught something more about this being his first time, and he wasn't sure. Daniella kept smiling and nodding, then in the middle of him shaking his head no, she upped the ante and just casually removed her bikini top. Her big nipples, already a dark brown from the few days of sunshine we had, were already erect and pointing directly add him.

The Greek Boy's eyes instantly track down to her perk breast and he stopped shaking his head no.

'She got him,' I chuckled to myself. Like a well trained hunter, Daniella went into for the kill. She reached up and looped her left arm around his neck and pulled him in close and kissed him full on his lips. He attempted to pull back, but she wouldn't let go. She held tight and pushed her red tongue into his young mouth. With her free hand she began to fumble with his black slacks. In a few quickly swift movements, his belt was undone, and his slacks were falling to the floor.

She stuffed her right hand down the front of his boxer shorts and grabbed his cock. "Oh mio Dio!" she exclaimed as she pulled her tongue from his young mouth. From his boxers she flopped out his huge cock. Even though it was only semi erect, Daniella's hand looked tiny as she attempted to grasp it. She pointed it at me and began to pump it up and down. "Have you seen this? I'm not sure I can take all this," she asked me with a big smile on her face.

"Don't worry darling, I have faith in you," I said encouragingly.

Daniella smiled before turning back to the Greek Boy and told him to fully undress. He began to quickly kick off his shoes and claw at his hoodie. A few seconds later he stood there completely naked in the middle of our hotel room. He was very skinny which just made his impressive cock and huge balls look even better.

Daniella, already half naked, laid down on the bed, spread her legs and pulled her bikini bottoms to the side, giving him a great look at her dark, hairy pussy and big clitoris. She ran her hand down the length of her pussy several times until we both could hear that she was good and wet.

The skinny Greek Boy looked less nervous now as he stood naked in the middle of our hotel room stroking his big cock as Daniella played with her beautiful mature pussy. Soon his cock was rock hard and standing up on its own.

Daniella gave him a wicked grin before she sat up and moved to the edge of the bed. With her left hand she continued to stroke her hard clitoris between her thumb and forefinger. With her right hand she reached out and grabbed the young man by his large cock and pulled him towards her open mouth.

In a single swift motion, she swallowed his cock whole, burying it deep into her throat. In response, the Greek Boy's huge hairy balls pulled up tight to his groin and his legs began to shake. For a second I thought for sure he was about to come.

Danielle must have senses this too for she pulled his big cock all the way out her gaped mouth. Her red lips were wet with slobber and spit, but she smiled, and her eyes twinkled. She opened her mouth again, and this time, more slowly, began to work the head of his cock with her expert tongue. She slowly licked from his balls, up his huge shaft to it's big bulbous head. While there she slowly licked his pee hole and managed to get her tongue a centimetre or two in there before he put both of his hands on her head and started slowly thrusting his cock into her eager mouth.

Danielle obligated and opened her mouth wide. Like a pro, she grabbed the base of his cock with her right hand which stopped him from pushing too deep down her throat. It took a good dozen thrusts and some gagging, before Daniella and the Greek Boy found a good rhythm to fuck her mouth.

As he pounded away, Danielle ran her free hand down to her open pussy and began frantically rubbing her clit. I few seconds later her body tensed with her first orgasm as her brown nipples bounced up and down in the air with every thrust of his cock.

Quickly the Greek Boy's breathing became more and more ragged. It wouldn't be much longer until he came too. To help maters along, she Daniella pulled her wet fingers from her pussy and reached up for his hard balls. They were the size of baseballs, pulled up tight against and ready to cum. She groped them hard for a few seconds before she pushed passed them and slip her middle finger up to his anus.

His stride faltered for a second, but it didn't stop her. She let go of his cock with her left hand and then used it to pull him in tight. She pushed his cock so deep into her throat that her nose almost touched his stomach. Then with a sharp jabbed, she pushed her middle finger as deep into his ass hole.

The Greek Boy didn't have time to say no before he started to orgasm. With great tremendous grunts he began to shoot his cum down her throat. Like a champ, Daniella held her place and let him finish in her throat. After a good 30 seconds she slowly pulled his huge cock out of her mouth until it hung in front of her like a defeated snake.

Danielle and the Greek Boy sat there for a moment as they both tried catching their breath.

Finally, Daniella croaked, "Bravo, Bravo."

To Be Continued...