Breaking the Rules: A holiday massage finishes with oiled-up group sex (Part 2)

Christian JA
10 min readJul 11, 2024

--

Continuing from Part 1

“You want more? That is very, very bad. I saw you look at him then too…” Lily whispered to you.

“No, I…” As you tried to respond, you felt her fingers on your bikini bottoms, over the top of your pussy. She held it there as the waiter walked over. The bubbles in the pool allowed everything to be completely covered and secretive as you tried to hide your facial expressions.

“Make sure you don’t make it obvious. The waiter is coming.” Lily’s switch from being slightly embarrassed to controlling had you gripped. You were both remarkably similar, but you couldn’t help but think that you might be breaking the rules of our arrangement if she continued. “Thank you so much!” Lily said as the waiter placed two more margaritas behind you and asked for a room number. “Put them on ours. Room 32,” Lily said as her fingers continued to rub your pussy slowly in a circular motion. The waiter nodded with a smile, almost as if he knew something was going on without being able to see it. “Room 32. You might want to remember that. Oh, and say thank you like a good girl.” You realised how quickly you could orgasm from this and didn’t want to break the rules, so you grabbed her hand and pushed it away from you.

“You really think you’re in control here, don’t you?” you questioned me with a smile.

“No no. I was just telling you as you asked me.”.

“Hmmmmm. You are trouble, Lily. Besides, I have some rules that I need to stick to; otherwise, I will be in a lot of trouble.”

“Oh my god, I am so sorry. It was way too forward of me, and I didn’t want to cause any issues,” Lily pleaded, almost panicking that she had crossed the line.

“Ha, not in the way you think. Besides, you really think those two wouldn’t want to watch us? Look at them pretending not to notice us,” you laughed as you both glanced over at us. “No, he would be very happy to know you had been playing with me. I am just not allowed to cum… for two days.”.

“Fuck. That is so hot. So, you like being edged?” Lily asked.

“Yes. A lot. Maybe not this much, though.”

“How mean of me!” Lily giggled as you clinked your glasses.

“Cheers. It is very good to meet you. Although, stay away. I have strict instructions,” you whispered.

“What happens if you break them?” Lily asked, intrigued by me.

“A whole other story, Lily. And these jets are really starting to make me want a massage too,” you said as you leaned your head back and felt the pressure increase in your lower back.

“Oh my god! I know just the place. Why don’t we go?” Lily answered.

“Really? Somewhere around here?” you asked. “And you’ve been?”

“Yes! I went a few days ago. It’s amazing. The best massage I’ve ever had, seriously. Although I don’t know if it’s a good thing with your new game…”

“Good point. I’m not sure I can take much more touch, and the challenge has barely started,” you replied. “Especially after you!”

“Well, an offer is there if you want to take your mind off of sex. Besides, I think if you go back and tell him what happened between us, he will struggle to keep his hands off you,” I watched as Lily smiled at me whilst talking. I wondered what was happening and what you were talking about. I couldn’t concentrate and had all thoughts of you going back to their room, being used by them both, thoughts of just you and Lily. I could feel my cock swelling again, and I had to fold my legs to hide what was going on.

“I’m telling him. I want to torture him as it was his idea,” you said with a little wickedness.

“I think you should. And then, once you’ve told him, let’s go get that massage. Leave the boys here while we have a pamper afternoon.”

“You know what? Let’s do it. I could really use one.”

As you both left the hot tub, you split as she walked along the other side of the pool, almost mirroring your pace as you returned to us.

“Have fun?” I asked as you sat on the end of my sun lounger. You turned and looked towards Lily, grabbing my hand and putting it inside your bikini bottoms under a towel.

“What do you think?” you responded, still looking across to Lily before turning to face me. My fingers explored you, instinctively rubbing your swollen clit. You were soaking. Your whole pussy was covered in your juices, and I was shocked at how wet you were.

“Fuck me? What went on?” I continued to play with you in public, with others around us having no idea what I was doing to you. “This is breaking the rules too. Two days, we said”, I immediately took my fingers out before you lent forward and grabbed my hand. You looked me in the eyes and started to suck them, licking your cum from them slowly before responding.

“Let’s just say you aren’t the first person to have your fingers there today.” Your tongue took the last drops of your cum from my middle finger before your hand moved up my thigh. “Poor you. You having to hide yourself because you’re getting so turned on about what we were talking about?” you teased. Your hand ran up the inside of my shorts. “Do you want me to tell you?” you giggled now.

“Fuck. No. I mean, yeah, I want to know. But I’m already struggling.”

“This was your idea.” Your hand gripped my throbbing cock as Lily watched us. She was the only person around the pool, along with her partner, who knew what was going on. You leaned in and whispered, “Shall I tell you while I have your cock in my hand?” Before I had the chance to respond, you released your grip and smiled. “I don’t think so, actually. I will tell you, though.”

“You’re really turning me on. This is going to be so hard.”

“It’s going to be even harder when you hear what she said to me…”

“You always find yourself in these positions, don’t you?” I asked, admiring how confident you were when it came to these interactions.

“Well, that’s because I’m such. A bad. Girl. Aren’t I?” she said as she got closer to me. “Where was I? Oh, that girl across the pool? Lily. And thats Ali,” you said, pointing at them somewhat covertly. “Well, she did tell me that they had a waitress back at their room the other night. In quite graphic details, actually.”

“Fuck. Really?” I asked, my cock twitching.

“Yep. All I could do was picture myself in the waitress’ position. She teased me, actually. I let her, too. Does that mean I broke the rules?” You asked in a bratty tone.

“Yes. You realise that it ends up with more time added on before I touch you. And I’ll make sure I leave some red marks on your arse too. You know that, right?” I asked, grabbing the back of your head as I leant into kissing you. The kiss was deliberate and slow. It was probably too much for being in public, but I knew we were being watched, and you were always so hot when you were a little bratty.

“I do know. And at this point, I don’t really care,” you responded as our tongues continued to explore each other. “Her fingers felt so good over my pussy. I wanted more. We’re going to get a massage in an hour. I’m sure she will reveal more to me on our little girls day.”

“A massage? And you think you’re going to last two days? I know how turned on you get when you’re covered in oil and you have someone’s hands rubbing your thighs.” I challenged you.

“I guess we will have to see, won’t we? If I don’t come back for a while, who knows where I might be?” You smiled, and I noticed how erect your nipples were, clearly visible through your bikini top.

“You’re really enjoying this, aren’t you?” I asked before noticing that Lily was walking around the pool. “Looks like your friend is coming over,” I said before you sat on the sun longer next to me, applying sun tan lotion as she approached us.

“Hey guys!” she said as I admired her body, attempting to avert my gaze and look her in the eyes.

“You must be Lily,” I said, awkwardly putting a hand out to shake hers.

“A handshake? How formal of you! And not even standing up to greet me,” she said, looking at you as you both giggled.

“No, sorry… I.. it’s just,” I fumbled my words, knowing I couldn’t stand up given how swollen my cock was.

“Don’t worry, I think I might know the reason why,” she said, laughing as she sensed my embarrassment. She sat on the end of your sun lounger, staring at the towel that covered me and placing her hand on your thigh. “It seems like you’ve been filled in on our little chat,” she said, squeezing your leg. You wanted to spread your legs further and just let her play with you so badly. Your pussy was aching for touch. But the focus was on teasing me. “It’s why Ali isn’t over here. I filled him in too.” She turned around and looked at him as you and I looked over too. He had a grin on his face with his legs slightly raised, hiding anything that was going on in his shorts. He picked up his book as he gave Lily a look of ‘you fucking tease’.

“Oh, he’s struggling too? You poor boys. At least Lily can do something about it,” you said to me, indicating your slight irritation at the game I decided to play with you.

“Hmmmm. I might leave him too. I think it’s quite a fun game, actually,” Lily said, smiling at me. You felt a pang of jealousy as she had a seductive look across her face. A feeling that crossed wires for you — all of a sudden, you couldn’t get the vision out of your head of me and her.

“Well. Given your new friendship, this is going to be much tougher than I thought,” I said, adjusting again and feeling the blood pump to my throbbing cock.

Lily moved her hand further up your thigh. “Is it because you’re thinking that I might do something with your pretty girlfriend?” Her fingers were just inches from your cunt. You felt a rush. You were almost gushing. You looked at me, mouth open, wanting more touch but knowing you couldn’t in public.

“You are forward, aren’t you?” I said to her as I watched her hand.

“Is that not allowed?” Lily asked.

“It is,” you said, looking at me for agreement.

“You can be as forward as you like, Lily. But the rules of the game prohibit touching for two days. But you know that, don’t you?” I responded.

“This isn’t touching, though,” Lily said, her hands moving up and down your thigh as one of the waiters walked past. “What happens if she breaks the rules?”

“Punishment. I’ll make it worse for her,” I said as you watched the back and forth between us, thoughts of Lily’s mouth wrapped around my cock swirling in your brain.

“Ooooh fun! Can I watch?” she said with a grin. I took a moment to appreciate how attractive you both were, the sun beaming down on you as beads of sweat ran between your tits, imagining you tied to my bed as Lily watched me edge you, deciding which toy I’d use to punish you. I looked at you to gauge your response.

You replied, “Why would you just watch? I’d want you to join in,” you said, putting your hand on hers — a soft moment of trust. I thought to myself, It’s amazing how you attract these beautiful, interesting people into your life. But you had that about you — an aura that made people want to know you.

“Join in? But you might have to watch me take your partner’s cock while you’re tied up. Are you sure you’d be ready for that?” Lily said as my cock twitched again. I let out a sighed smile. ‘Fuck me, this is not how I expected the day to go,’ I thought to myself as I could see how turned on you were getting in. You have a look that shows me when you really want something: subtle mouth movements, your eyes moving between hers and her mouth, shuffling slightly, adjusting, and your nipples poking through pretty much any top you have on. Your hand was still sitting on hers, desperately wanting to pull it closer to your pussy. In times like this, you almost want to forget that you’re in public and just let someone have their way with you.

“Well, I guess if I’m breaking the rules, I’d have no choice,” you said as Lily moved over to my sun lounger, preparing to tease you more.

“I guess you wouldn’t,” Lily said as she put her hand under my towel. “And fuck, he is big, isn’t he?” she said as her fingers moved over the outline of my cock. You spread your legs more, desperate to touch yourself. I moved my hand onto her thigh, leaning in closer as her hand released my cock under the towel. You didn’t know what was going on under there, and it was driving you crazy. “Oh fuck. He’s so hard. Are you sure you’d be okay watching me get fucked by it? After all, it is yours,” she said as she started to stroke me expertly. It was so well done that no one around even noticed what she was doing.

“If she decides to break the rules today, she has to face the consequences. Do you want to know what I would do to you?” I said, looking at Lily. I leaned in and whispered to her as you watched. She opened her mouth, shocked and almost smiling. You wanted desperately to know what I was saying as my hand moved up her inner thigh. You noticed she had goosebumps, and she was clearly getting so turned on by what I was saying to her. ‘Is this what it would feel like? Watching the two of them flirt and give each other attention’; your boundaries were being pushed, which only made your clit swell. Lily looked at you before standing up.

“I think it’s time for our massage. I need one now. Come on,” she said, as she couldn’t take the grin off her face. “I’ll see you in reception.”

Continue to Part 3…

--

--

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+