Breaking the Rules: A holiday massage finishes with oiled-up group sex (Part 1)

Christian JA
9 min readJul 11, 2024

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As I sat on my sun lounger sipping my cocktail, I watched as you walked along the edge of the pool, admiring your body as the heat hit me. I noticed others were admiring you too, mainly older guys who were with their partners, most likely in sexless or boring sexual relationships. Perhaps an unfair assumption; even if they weren’t in sexless relationships, how could they not admire you? I imagined their sex lives were the polar opposite of ours.

Sardinia had been perfect so far; we had relaxed, eaten at some of the best places around, but mostly enjoyed each other in countless ways in the bedroom. We explored various fantasies, fucking for hours, multiple times a day, dirty talking and teasing each other, so much so that I wanted to explore one of mine — edging for two days. The idea that we wouldn’t be able to do anything to each other despite how turned on we’d be was a huge turn-on, despite your initial protests. “That’s such a waste of time!” you moaned before I explained to you how fucking intense the orgasms would be after that long. Besides, we were away for three weeks, so we had plenty of time to continue where we had left off. Your bratty remarks stopped when you realised how fun they could be.

As I smiled and watched these people stare at you as you walked around the pool, my thoughts drifted, and I noticed my cock start to swell. I sometimes blamed this on the heat, but this was purely from being turned on by the fact that you were mine, and it was me that got to use your little holes every evening. It had only been a few hours since the agreement, and I already realised how tough this would be, particularly given how we had been so far.

You turned to look at me, smiling as you sat on the edge of the pool. I winked at you as you let your legs dangle on the side, and you caught the eye of a couple opposite (who were flirtier with each other than other couples around the pool). He was Greek-looking, with a dark tan and facial hair, while she was a petite redhead with a fair complexion and blue eyes. I mouthed to you, ‘you have some admirers’, and motioned to them as you sarcastically responded, ‘Oh, shut up’. But as you looked at them, your gaze hidden behind your sunglasses, you could see them staring, which turned you on too. You loved the thought of being used by another couple, but you equally loved being the object of their thoughts. ‘Maybe they will talk dirty about me in bed later? Maybe they’re talking about me now?’, you thought to yourself as you decided to show them a bit more. You stood up and walked towards the handrail of the pool ladders, grabbing it with both hands and bending over slightly as you lowered yourself into the pool. I could see they couldn’t take their eyes off you, and the petite, red-headed lady repositioned herself, spreading her legs slightly as she dipped her sunglasses and quite openly stared at you. You pretended not to notice them, but you could tell you were being watched. As you swam over to the edge of the pool, closer to me, you noticed that I was shifting uncomfortably on my sun lounger.

“Someone getting a bit excited?” you said quietly with a smirk.

“Har har,” I responded with sarcasm. “This is going to be much tougher than I thought.”.

“Oh no!” you quipped sarcastically. “Well, listen, this was your call. And now you’ve just got to watch me get admired and have your bad thoughts without being able to take me up to our room,” you said in a more hushed tone, with your bottom lip puffed.

“Don’t worry. This is part of the fun. It’s just going to be tough; that’s all I’m saying.”.

“Sure.” You gestured to my trunks, the outline of my throbbing cock clearly visible. “Maybe I’ll introduce myself. Make it even harder.” As you spoke, I noticed the redhead stand up to get in the pool. She had quite big tits for her small frame and walked with an air of confidence, not too dissimilar to you. As she lowered herself into the pool from the other side, you smiled at me and swam off. You didn’t make it obvious that you were swimming towards her; you simply floated closer to her, but I knew full well you were doing it with the intention of introducing yourself. As I leant back, the music turned up, and a waiter asked if I wanted another drink.

“Water is fine, thanks,” I answered as I turned.

When I turned back, I could see you both speaking to each other, and the redhead was giggling already.

“So, where are you from?” you asked her after learning her name, Lily. You had exchanged the usual stuff: how long they had been at the hotel, when they were leaving, etc.

“Copenhagen,” she responded before you told her where you were from. You’d never have guessed from looking at her that she was Danish, but her English was perfect, and you couldn’t stop staring at her tits as she swam closer to you. You spoke more about the holidays so far and places to check out before I watched you turn to me and point. I waved to you both, unable to hear the conversation but assuming that you were introducing me. You did the same to her partner, waving as she told you his name, Ali. I wanted to leave you to continue talking to her without me interrupting, partly to see what you’d come back and say and what had been discussed.

As the conversation continued, Lily became slightly more complimentary and suggestive, referencing how pretty she thought you were and making a subtle suggestion to sex, telling you how she and Ali had been pretty “active,” and it was nice to take a break from the bedroom. When you looked back at Ali and back at Lily, you started to daydream slightly about what they would be like in bed, struggling to concentrate on the conversation.

“I guess you could say the same for us!” you replied as you tried to gather your thoughts.

“Oh really?! Interesting! Well, I feel sorry for our neighbours if that’s the case!” Lily giggled.

“I would be very surprised if they hadn’t heard us,” you responded with an amorous smile.

“Is someone a noisy girl?” her response immediately turned you on, like a switch. Being called anything, followed by girl always hit you: dirty girl, messy girl, good/bad girl. You knew she knew what she was doing, but you put it down to her flirtatious nature more than anything.

“Well, when he hasn’t got his hand over my mouth or anything else in it,” you said, almost testing her. Lily turned to look at me instantly, likely doing exactly what you did moments earlier — working out what our sex life looks like.

“Anything else? Now that is a conversation for another cocktail,” Lily said as she called a waiter over. In the meantime, I gave Ali a thumbs up as he picked up a book, and we both pretended like we weren’t watching you both (along with everyone else around the pool). Lily ordered you both a margarita as you moved towards the jet pool. I watched as you turned to look at me and gave me that smile — the one that tells me you’re up to no good and makes my cock twitch. You both sat on small ledges as Lily turned the jets on, hiding any conversation that you were having from others around you due to the noise. “So, tell me. What else might be in your mouth as you’re hiding all that noise from your hotel neighbours?” Lily asked as she sipped her cocktail.

“Very forward!” you responded, taking a sip of yours.

“I will blame the cocktails,” Lily replied.

“Yeah, yeah, sure.” You took a bigger sip this time. You didn’t know whether you should be telling a complete stranger such intimate details so early on, but you found her intriguing and wanted to hear more from her too — a trade-off that would mean you going first. “Well, that depends, Lily. If I wanted to tease him, it would usually be one of his fingers. If I have been very bad, it might be my dirty panties.” As you sipped your Margarita this time, you held eye contact and didn’t giggle, taking a more alluring stance.

“Oh wow. Fuck. I wasn’t expecting that!” Lily said as she went a little red.

“You weren’t? You expected me to be vanilla?” You started to take control of the conversation.

“Not at all. I just, ermmm. I am slightly turned on hearing that, that’s all!” Lily said as she leaned closer to you. I noticed her response, although I couldn’t hear what you were saying. All I knew was that you were definitely having a charged conversation based on your body language.

“Already? Lily, I very much doubt that you two are vanilla,” you challenged her.

“Well, no. But I guess it is always exciting hearing about another couple and imagining them.” Lily seemed almost embarrassed about how quickly she said that. “Sorry, I..”

“You what? You imagined me getting fucked with dirty panties in my mouth?” you said in a hushed tone as Lily opened her mouth and smiled slightly. You both sat closer together as you felt the pressure of the jet pool against the bottom of your backs. “Speechless?” you asked.

“Fuck me. I am going to change positions on these jets if you keep going,” Lily blushed.

“Oh, come on, Lily. I have barely said anything. Besides, are you telling me you haven’t had anything covering or in your mouth this holiday whilst Ali, is it?” you asked, confirming his name.

“Yes”

“…whilst Ali fucks you?”

“Well, no. I am not telling you that. Because I have,” Lily said as the pressure of the jets increased for you both.

“Spill then,” you demanded.

“Okay. Well, the other night, we invited a waitress back to ours for some drinks, and I am sure you can work out why my mouth was busy.” The bubbles around you increased as you felt your pussy ache. ‘Fuck, he is right. This is going to be so hard’ you thought to yourself.

“No, I am very vanilla, Lily. You might have to tell me”, you responded sarcastically as the waiter passed and leant down, noticing your drinks were finished.

“Can I get you another two?” he asked you both as you asked for the same again.

“Tell you? I guess if I tell you, you will have to return the favour”, Lily said with a smile as she moved even closer to you.

“I quite like this game,” you whispered to her, noticing a couple of older guys behind you both watching.

“Where do I start? Well, the reason I was so quiet was because after I watched Ali fuck this petite brunette waitress so slowly while I played with myself, I was ordered to clean her cum off of him. So, I did as I was told and licked every last drop off of his huge cock before I told her how badly I wanted to taste her pussy…”, you shuffled uncomfortably as you asked her to continue. ‘Huge?’ you thought to yourself as you looked over at him again and imagined what his cock was like under his shorts.

“…So Ali put me on my back and started to fuck me. I was so wet from watching them too, and as I lay back on the bed, before I knew it, she had positioned herself over my face and lowered herself closer to my mouth. Despite my moans, they were muffled by the fact that my tongue was exploring the waitress’ pussy. I didn’t even know her name, but it was so hot. At one point, Ali leaned down slightly as he was inside me and teased her arsehole with his tongue at the same time.”

“Okay, fuck me. That is really hot.” You could feel your nipples harden as you imagined the pressure of the jets in a different position. “Tell me more…” you requested as she continued.

Continue to Part 2…

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Christian JA

I write addictive erotic stories, encompassing all sorts of kinks, usually from a first person POV.. but playing around with new ideas. More to come. 18+