Jessica by the Pool
by alan14
Copyright© 2026 by alan14
Fiction Story: Jessica is by the pool, in the sun, with a cocktail, but she's not happy. She has a job to do, but can't do the job until the subject arrives. Still, she's getting a tan, and there's plenty of people to keep her company at night...
Caution: This Fiction Story contains strong sexual content, including Fa/ft Vignettes .
I was lying by the pool, bored out of my mind. I’d been here for five days with no sight of my contact. Still, I was getting a cracking tan, and the view was great ... like the view approaching me now...
“Would madam like another?”
“You know Paolo, that last one went straight to my head ... I think I’ll switch to coke.”
Paolo was new this morning. Leon and Sacha had been serving in this bar for the last few days, a fine-looking pair who served me well last night.
I don’t normally go for threesomes, but Leon and Sacha appeared to be some kind of buy-one-get-one-free deal, and I wasn’t complaining.
Leon was tall and lean, typically olive skinned mediterranean complexion with a very long, slim cock that seemed to reach all the way into my womb with each stroke. It felt nice when he was gentle but soon got uncomfortable when he was rough.
Sasha, however, was short and stocky, from one of the Balkan countries. He had terrible breath, so no kissing. His cock was quite unique, only average length, and the shaft was as slim as Leon’s. It was the head that made it remarkable, as big and round as a pool ball. He used it in my arse, and my arse knew it had been used, which is how I like it.
A shame I’ll never see them again, but sex is only ever a one-time deal for me.
My contact still hadn’t shown by evening, so I collected my things and wandered into the restaurant ... sea bass tonight I think, they have a nice pinot grigio that will pair with it wonderfully. After dinner, I’ll take a walk along the beach to watch the sunset ... I mentioned as much to Paolo, and he took the hint.
We didn’t make it back to my room; Paolo took me to a secluded cover, where he took me.
The promising bulge in his shorts turned out to be everything it promised and more, 8 inches of thick, dark meat that grew hard as iron between my lips, then he pounded me like a bull with anger issues.
We fucked until it was full dark, then we fucked some more as the waves lapped against us.
Afterwards Paolo walked me back to my room, where we showered off the seawater, then we replaced it with sweat as he fucked me senseless on the emperor sized bed.
Paolo will be a tough act to follow, but there are plenty more fish in the sea ... I know this from fucking in the sea earlier.
Another day, another book, another towel on another sun lounger.
I think I’ll stick to white wine spritzers today; those cocktails did terrible things to my head.
Another new barman, today’s is Mark, a British guy with some quite tasteless tattoos and a horrible demeanor. I shall look elsewhere for tonight’s entertainment ... I think I found the perfect person...
Five loungers down, a girl on her own. I raised my sunglasses to get a better look ... about 18 I’d say, the perfect age ... I remember when I was that age, just becoming aware of my power over men ... lovely.
I waved and patted the lounger beside mine.
She smiled and stood, collecting her phone, vape, book, and glass.
Oh my ... she’s tall ... maybe 6 feet. Slim with apple sized breasts and no bikini top to hide them from my hungry eyes.
I watched her closely as she moved towards me, my pussy grew moist as she walked, her long legs closing the gap quickly.
I held out my hand, “hey, I’m Jessica.”
“I’m Emma, pleased to meet another Brit.”
“We get everywhere honey,” I replied, “I’ve not seen you before, have you just arrived?”
“Yes, my parents are checking in, so I thought I’d make myself scarce while they complain about the room ... mum always complains about the room.”
“Your parents are OK with you sunbathing topless?”
“No, but they won’t see me, because they both fear sunlight, so they’ll stay inside.”
“Ibiza in June isn’t really the best place for vampires,” I laughed.
“That’s what I told them, but would they listen ... no they wouldn’t.”
As we chatted, I reassessed my earlier guess, I think she’s 16, 17 tops ... still utterly perfect.
Mark approached, I was pleased to see Emma keep her eyes on me as she ordered our drinks, on her room bill, I like her.
After about an hour I made an excuse to go back to my room, casually suggesting she join me ... she agreed ... I was glad I chose a white bikini, because I was very wet down there.
We put our stuff down on the table by my window, I was about to pull her close for a kiss, but she beat me to it ... wow, she knew how to kiss.
While we kissed, out on the balcony, in view of everybody, if anyone down there cared to look up, Emma pulled the string on my bikini, letting it fall to the floor. Now the people below really had something to look at, but they were too intent on looking at the pool or reading their books.
“Are they real? They feel real?”
“Yes, they’re real,” I replied.
“I love big tits ... mine are so small...”
“Small, but perfect ... try carrying these funbags around for a few days then you’ll be praying for a b-cup.”
She bent at the waist as I spoke, taking a nipple between her lips, she sucked and teased it with her tongue ... I don’t think this is Emma’s first rodeo...
Clearly used to multi-tasking, Emma wasn’t content simply playing with my breasts, she placed both hands on my buttocks, massaging them gently for a moment, before slipped them inside my bikini bottoms. She continued her massage, moving her hands in ever decreasing circles until her fingers reached my bum crack. She parted my cheeks and her fingers worked their way inwards...
“Cheeky girl,” I gasped.
“Is this OK?” she asked.
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