The End-of-Year Trip Pt. 18

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Jake and Yaiza end their vacation in Mykonos.
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Part 18 of the 24 part series

Updated 03/02/2024
Created 07/23/2023
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(Thanks for reading my stories and for your ratings and comments.

All characters are over 18 years old and this story is solely a figment of my imagination.

My language is Spanish, I apologize for any grammatical errors I may make when translating the stories into English).

The End of the Year Trip 18 - The Roman Festival

It wasn't hard for my beautiful redhead to seduce Emily, after that first kiss in the pool, it was easy for her to keep taking steps, until she had her naked in the pool eating her pussy to orgasm.

When Emily asked Selene to bring her to orgasm, Selene kept her on the edge for hours, and only let her cum when she agreed to let me fuck her.

That was almost two days ago now, during which time we haven't left the playroom, in that time, Selene and I haven't stopped fucking her, turning the repressed, lesbian schoolgirl into a cock-craving slut.

Now I have her sitting on a sybian, keeping her on the verge of orgasm, begging me to cum, while I fuck Selene bringing her to the orgasms, I'm denying Emily. Just as Selene reaches another orgasm, the door to the living room opens and someone comes in and leans against the wall watching us fuck.

I don't stop fucking Selene though I avert my gaze to the intruder, smiling as I discover it is Martha, Paul's niece and Emily's friend and lover.

"You shouldn't be here, leave before you regret it;" I say redoubling my thrusts at Selene.

"You are a pig;" she yells at me, "You didn't have enough with your slave girls that you had to fuck Emily and turn her into one of them."

"I haven't done anything to Emily that she didn't want;" I reply, "On the contrary, I've done everything she's asked me to, including fucking her virgin ass."

"I'm sick of listening to the sounds of your orgies as I remain in my rooms;" she replies, moving closer to me, "Sick of hearing your slave girls beg you to fuck them harder. I've been horny since I arrived at the villa and saw your slave girls in the pool, with that 'Fuck how we've been fucked' expression. I haven't stopped masturbating imagining how they must have felt;" she comments watching my cock go in and out of Selene's pussy.

"You know what you're exposing yourself to if you don't walk out that door right now;" I tell Martha again, pulling out of Selene's pussy to stand in front of her and cum on her face.

"I'm not one of your slave girls that you can do whatever you want to, but I assure you I'm not walking out that door without you fucking me, without feeling your cock in my pussy;" she instructs me in a firm voice.

I watch Martha, again dressing provocatively as she has done since the first day she arrived at the villa, the blue silk nightgown barely concealing her tits, letting me perfectly see her hard nipples and matching lace panties.

I walk over to her and grabbing her long blonde hair I pull her head back as I bring my free hand to her pussy, finding it completely soaked.

"Fuck Jake, you're hurting me;" she screams at me trying to free herself from my grip.

With a quick movement I release her hair and grab both her hands pulling them towards one of the racks, "Hush slave girl, don't speak without permission, you are a slut who wants this, your pussy gives you away;" I order her forcing her to lie face down on the racks, pinning her wrists and ankles to the metal rings.

"Let go Jake, I told you I'm not a slave girl, I just want you to fuck me and that's it;" she comments to me frightened.

"I warned you what would happen if you didn't leave, now it's too late, I'm going to fuck you, but not the way you imagine;" I indicate hitting her exposed ass several times with my hand.

I move a few moments away from Martha and approach Selene, "Untie Emily and go find Lady Yaiza and tell her I have the toy I promised her ready to amuse us for the rest of the vacation;" I order her.

I wait for Selene and Emily to leave the room and close the door behind them before I go back to taking care of Martha, I position myself behind her and after ripping off her panties I begin to masturbate her.

Martha tries to resist the pleasure, but soon begins to moan, at which point I stop and move away from her again for a few seconds. As I approach Martha again, I begin to play with my fingers in her ass finding it very tight.

"Please Jake, I'm a virgin there, fuck my pussy if you want;" she pleads with me in tears.

Ignoring Martha's pleas, I reach over to the wall and grab a metal hook ending in a ball, I pour lube over the ball and Martha's ass and begin to slowly insert it while stimulating her clit.

Martha's screams from the anal intrusion are quickly eclipsed by the moans of pleasure provoked by my fingers in her pussy, when the ball of the metal hook is completely inside her ass, I stop leaving her again on the verge of orgasm.

Without releasing the hook, I position myself in front of Martha, running my cock through her mouth, "Let's see how well you suck a cock;" I tell her, "If you do it right, I'll let you cum."

Martha opens her mouth and starts sucking my cock demonstrating great skill, "Fuck Martha;" I say holding back my moans, "No one would say knowing you go to Catholic school that you have sucked a lot of cock;" I add with my voice cracking.

Noticing that I am about to cum I pull out of Martha's mouth and position myself behind her, "Fuck me Jake, I need to cum;" she asks.

I play with my cock at the entrance of her pussy as I slowly pull the metal hook out of her ass, before the hole closes, I push my cock in almost all the way pulling a loud scream from Martha.

I continue to fuck Martha's ass when the door opens and Yaiza walks in and stares at us, "You're a fucking bastard Jake, we talked about me being the first to fuck her pussy;" she yells at me.

"Easy Yaiza, I am enjoying her virgin ass, I have reserved her pussy for you;" I tell her before I let out a snort and cum filling Martha's ass with my cum.

I pull out of her ass giving her a couple of spanks, "Relax Martha, I assure you that you are going to get tired of cumming, Yaiza is going to take care of it;" I tell her letting Yaiza get behind her with the strap-on and the fake cock she uses on all her slave girls. "And when Yaiza finishes you, it will be the turn of the rest of the slave girls, including your friend Emily."

------

This afternoon, the last of the vacation, is the first afternoon Martha spends with the rest of the group, though surely not as she expected, but tied to a wooden frame, being fucked and brought to orgasm by all the slave girls and her friend Emily.

While the girls are having fun, Yaiza and I are inside the villa, talking about the next steps to take when we return to Kanaan.

"That will be tomorrow, tonight I want us all to go to a beach party."

I look at Yaiza surprised at what she just said, not sure if I understood correctly.

"I want us all to go to the party being held on the beach tonight;" Yaiza repeats to me, "It's a Roman themed party, with music, food and drink, there will be lots of people and the slave girls will go unnoticed."

I hesitate for a few moments, I trust my slave girls, of course Selene and also Janet, but I don't know if I can trust Patricia not to do anything foolish, as for Yaiza's slave girls, Bashira and Yulien won't be a problem, although I don't think the same about Mary Jane and especially Claire, and so I tell Yaiza.

"Are you sure we can trust all the slave girls?" I ask her.

"Yes!" she answers me very confidently. "I know they are going to behave well; they are legally slave girls and I am sure they don't want to become runaway slave girls, plus I have a game prepared that they will all like, including Emily and Martha."

"Where will we get the costumes for the party?" I ask her again, knowing she probably already has the solution figured out.

"Your friend Paul has a room full of costumes and masquerade costume of all kinds, and Roman slave girl togas abound among them;" she replies to me.

Half an hour later we all meet at the pool, and I let Yaiza do the talking.

"Today is our last night on the island, tomorrow we will return to Kanaan, and we all know what will happen then; "That's why tonight we will go to a party on the beach, without any master/slave girl role, you can have as much fun as you want, I want you to have fun, drink, dance and fuck, especially fuck with a stranger, and when we return to the mansion, everyone, and I mean everyone including Jake and I will tell what we have done, and the adventure that we like the most will get a small prize.

To my surprise, all the slave girls gladly accept Yaiza's proposal, and less than half an hour later, we all left the mansion heading to the beach, dressed in Roman togas, so that the girls looked incredibly sexy and desirable.

Just before reaching the beach, we separate so as not to attract attention, although I, ignoring the rules Yaiza has set, stay next to Selene, firstly because I don't want anyone but me to fuck her, and secondly, because after almost three weeks since the beginning of the vacation, I want to spend some time with her like two lovers, oblivious to everything that has happened this time.

To try to make that night perfect, Selene instead of dressing in a slave girl toga, as the rest of the girls have done, including Yaiza, Emily and Martha, has dressed as a Roman patrician, with a long blue tunic to match the color that stands out in her necklace, bracelets and earrings that we have found with the dresses, and that I have the impression that they are authentic complement a look that causes everyone who is enjoying the party in the beach to look at her carefully.

I walk beside him dressed as a Roman consul, wearing metal armor with a lion engraved on it, with my arms and legs exposed, causing my tanned and muscular body, to also draw quite a bit of attention.

"I like everyone to look at you and know that you are untouchable;" I say to Selene, grabbing her by the waist to pull her close to me and kiss her on the neck.

"Well, I don't like them looking at you;" Selene replies to me, "They all want you to fuck them, but today I'm the one who's going to decide who you fuck;" she adds turning to kiss me on the lips.

"I don't understand what you mean;" I comment to Selene without stopping kissing her neck.

"We have to win Yaiza's game, and you and me fucking doesn't count, although it can be a lot of fun;" she tells me with a mischievous smile on her face. "Order me something to drink while I take a look around," she adds.

I don't know who Selene intends to find to amuse us, but I find a possible target as soon as I approach the bar to order, a brunette beauty dressed in a fur suit and face painted with blue symbols, as if she were a Celtic warrior from the Scottish Highlands.

Taking advantage of the fact that I'm looking at what drink to order from all those at the bar, I take a closer look at the waitress, long legs, stylized by leather sandals knotted up to the knee, firm belly on which stands out a piercing in her navel in the shape of a triskelion, the same symbol she has tattooed on her right breast.

"Two Dark Macallan on the rocks;" I ask the waitress, who looks at me surprised that someone at a party like this would order a thousand-dollar-a-bottle whiskey.

"Won't this whiskey be a little strong for your date;" the waitress comments to me as she pours me both glasses, "That redhead doesn't strike me as the kind of girl capable of holding her own."

"You'd be surprised what my redhead is capable of putting up with;" I reply to the waitress, who is clearly flirting with me, "The question is whether you could put up with what she can."

"I am a Celtic warrior, I can endure the same as your redhead in any aspect, be it drinking or fucking;" she replies leaning over the bar, allowing me a perfect view of her tits through the ample cleavage of her dress.

"And I am a Roman consul, and therefore your place is kneeling at my feet as my slave girl;" I point to her, waiting for her reaction.

The young waitress takes a step back, flushed by my words, somewhat frightened but obviously aroused, as evidenced by her nipples marking themselves against the fabric.

"You'll have to tame me before you can fuck me;" she says stepping out from behind the bar to approach me.

"It will be my pleasure to tame you," I comment, "But first step into the bar and pour two more drinks."

The waitress returns behind the bar to pour two more drinks, I pay her for the four drinks and leave her a generous tip, before gesturing for her to come out and stand in front of me. As soon as she does, I pull a steel collar on a leash from my pocket and clasp it around her neck.

"Who is the fourth drink for?" the waitress asks me, looking all around.

"It's for the slave girl my redhead is bringing;" I reply pointing to where Selene returns accompanied by a blonde wearing a slave robe torn in several places that barely contains her big tits.

"Look what I just bought at a slave girl auction;" Selene comments pushing the blonde towards me.

As soon as I have the blonde in front of me, I bring my hands to her tits and start playing with them, causing her to let out a few light moans.

"At the auction they said she's a lesbian, but I think that's because she's never been fucked properly;" Selene comments to me.

"We'll check that in a while;" I tell Selene handing her a leash to attach to the blonde's collar, "First let's toast to a night of sex and passion and then let's go somewhere where there aren't so many people."

The four of us down our drinks in one gulp, the waitress drinks it with no problem, but Selene's and the blonde's faces show that it's too strong for them.

Selene and I guide our 'slave girls' along the beach until we reach a small rocky area where a cave opens up with its interior illuminated by the light of the full moon that seems to want to bathe in the waters of the Mediterranean.

"What is your name?" I ask the two 'slave girls', as we stop inside the cave.

"My name is Berta and I am from Rotterdam, I had been on vacation with my girlfriend for a week, this afternoon she brought me to the beach and we got together with some friends of hers, we started drinking and I started to feel sick, I think I fainted, the next thing I remember is being on a platform next to other girls being sold at an auction and bought by her;" she explains scared pointing to Selene.

"Don't worry Berta, your girlfriend must have wanted to play a joke on you;" I say looking at Selene, who looks back at me somewhat frightened, "We are in Europe in the 21st century, slavery doesn't exist except in sex games."

"My name is Dana, and I'm actually Scottish;" the waitress tells me, "And I have no problem being your slave girl tonight;" she adds running her tongue over her full lips.

"I am Jake and this is Selene, and I expect you to obey us in everything we command you;" I tell them grabbing Selene by the waist to pull her closer to me, "Understood slave girls?"

"Understood, Master Jake;" Dana replies getting more and more excited.

"Understood, Master Jake;" Berta replies as well, ducking her eyes to the floor.

"Perfect, then start kissing and undressing each other;" I order them.

"I'm not a lesbian;" Dana protests.

"Tonight, you are;" I point to her grabbing her hair to pull her head back, "If you want to have my cock fucking your pussy, you are going to eat Selene and Berta's pussy, and you are going to let them eat you, indeed you are going to beg them to do it, your other option is to get up and go back to the party."

Dana hesitates for a few seconds, but finally kneels down in front of Berta, waiting for the blonde to take the initiative.

Berta begins to undress Dana, caressing her body, playing with her tits, sensually kissing every inch of her skin, demonstrating that she knows how to treat a woman, arousing the beautiful brunette's arousal in no time.

Selene and I watch everything from a few meters away, I hold her by the waist, kissing her neck, with my free hand exploring her whole body until I end up in her pussy already wet with excitement.

Dana is slow to react and start undressing Berta, but as soon as she gets moving no one would say she has never been with a woman, she takes her hand directly to the blonde's pussy and starts fucking it with two fingers causing her to explode in the first orgasm. After that, without us having to tell them anything, the two completely naked girls lie down on the floor of the cave and start playing with their tongues in each other's pussy, the moans of the two girls echo throughout the cave, giving the impression that an orgy is taking place with dozens of people.

"Fuck me!" Selene orders me, slipping into her role as a Roman patrician, forgetting for a few moments that she is my slave girl.

I lead her towards a rounded shaped rock and bend her over it, lifting her dress so I can access her pussy, I don't need any more foreplay, her pussy is dripping and juices are seeping down her thighs, I move my hard cock over her labia, opening them slightly to observe her pink interior, Selene moves her hips back, trying to capture my cock with her body.

"Fuck me I said;" she screams again turning her head towards me.

"Beg me!" I reply continuing my games, holding her hips with my hands, pushing my cock lightly into her pussy, only to pull it out immediately.

"I'm not going to beg you in front of those two bitches;" she shouts angrily at me, "We said I wasn't going to be your slave girl tonight;" she adds with tears in her eyes due to frustration.

"And I am honoring it;" I reply, "Since you are not a slave girl and you are not going to beg me to fuck you, I am going to fuck those two sluts you said, Dana is eager to feel my cock filling her pussy, and Berta even though she doesn't want to admit it too."

I let go of Selene's hips and retreat a couple of steps back, as soon as she stops feeling my touch she starts to cry and it doesn't take her long to do what she has denied she was going to do, seconds ago.

"Please Jake, fuck me;" she begs me.

I move closer to her again, and grabbing her hips again I push my cock into her pussy penetrating her hard, causing her to let out a small scream. I have always loved fucking Selene this way, ever since the first time we fucked, I have loved pushing her to the edge, causing her to desire my cock, making her orgasms more intense each time, getting her to completely surrender to me, not because she is a slave girl like the last few days, but because she wants it and desires it, because we are made for each other.

Selene's moans are joined by those of Berta and Dana, who do not stop playing with each other even though we are not aware of them, they have surrendered to mutual pleasure and do not care about everything that happens around them.

After fifteen minutes and three orgasms I cum in Selene's pussy, who is completely devoted to me. I pull out of her body and look at Berta and Dana, who have been watching us fuck for a while.

"Come and clean my cock;" I tell them.

Dana gets up and starts to walk towards me, but I stop her with a wave of my hand.

"Not you Dana, Berta is the one who is going to clean my cock, you are going to clean my cum from Selene's pussy;" I tell her.

Berta looks at me, pleading with her eyes, but seeing that I don't back down, she gets up and comes to me, kneeling at my feet, looking at my cock, wanting to take it in her mouth but not knowing what to do.

Meanwhile Selene has laid down on the floor and holds Dana's head between her legs, forcing her to clean my cum from her pussy.

Berta takes my cock into her mouth, trying to do what she's probably seen in some porn video, but failing to take even a few inches inside, though the feel of her lips wrapping around my shaft is enough to make my cock hard again.