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Deedee’s Holiday - 03
🕑 Added 2025-09-24 13:00:16 +0000 UTC
Disclaimer: This story contains adult themes. It is not suitable for minors or the easily offended.
https://linktr.ee/spartacuswrites
Contains: Weight Gain
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Deedee’s Holiday
III
Unfortunately, I couldn’t spend every moment of every day in Ibiza hanging out with Deedee. The morning of my last Friday on the island, I woke up to a flood of messages from my team. One of the services we used for our client sites had updated its interface syntax, and everything was broken. While I was reviewing the messages, I got a text.
DD (8:17 a.m.): Photoshoot again today. I’m obsessed with this dress. Meet downstairs at 9?
If I had been at home, I would have been excited to dive into the code and fix the issues myself. But there, in that beautiful place, with a beautiful girl waiting for me, I was just annoyed.
Nikki (8:18 a.m.): Can’t today, work emergency
DD (8:18 a.m.): 🙃
Nikki (8:19 a.m.): Sorry
DD (8:19 a.m.): Hey, you got to get paid. Drinks later?
Nikki (8:20 a.m.): Yes. I’m going to need several
DD (8:20 a.m.): 😂😂
Nikki (8:20 a.m.): I’ll ping you when I’m done
DD (8:21 a.m.): Have fun!
It wasn’t really fair of me to blame my team. They probably could have handled it without me. But I never wanted to be one of those bosses who slack off while their employees do all the actual work. Plus, they were all super supportive, apologizing for contacting me even though I’d insisted up and down that this would be a “working vacation.”
In the end, most of what I did was moral support. The hotel’s Wi-Fi couldn’t handle video without a lot of lag, so I stayed on voice calls in case something went wrong and offered the occasional suggestion. Still, the sun was getting low in the sky by the time I was finally able to close my laptop. Thinking about Delia down at a bar somewhere, getting a head start on me, I remembered her message about a dress that morning. I grabbed my phone and pulled up her accounts before messaging her.
One account had a new video of Deedee walking along a veranda, lip-syncing a line from a song. It was cute, but I recognized her outfit and the scene—I’d helped her film it the day before. Still, I took a moment to appreciate Deedee’s tanned legs in a pair of khaki shorts and her cleavage jiggling in a blue lace-up top that showed even more tan skin, except for a loose, flowy part that covered her midriff.
It was the second video that shook me to my core. Deedee was lip-syncing a voice clip by some British guy, talking about how great being “on holiday” was. With each line, the video changed. It started on a plane, where she said, “Remember, catch flights, not feelings.” Then she walked up an outdoor staircase in a low-cut blouse, asking, “How’s your Monday?” She hopped off a low stone wall in a brown dress and walked toward the camera, saying, “What I need, is a six-month holiday, twice a year.” And finally, lounging in a bikini, she said, “Drinks by the pool, today’s office.”
It was a clever bit, combining the audio celebrating vacation with clips of Deedee’s sexy form enjoying her own vacation. What really got me, however, was the middle clip. I’d hung out with Deedee every day for the past two weeks, watching her relish every drink and dish Ibiza had to offer. I’d wondered more than once how she stayed so fit on such a diet. But in that snug brown dress, I realized there was no trick, no secret. Somehow, that simple dress revealed what I’d missed in each of her more revealing outfits—Deedee was getting thick.
It wasn’t much, a slight prominence to her hips, a softer tummy, and the faint outline of her belly button, but every time I rewatched the video, there seemed to be more jiggling and shaking as Deedee hopped off that wall and walked toward me. What really made me stare, made my heart pound and my vision blur, were those tits. More than the low-cut tops, more than the lace-up thing in the first video, more than the bikini in her final clip, that dress hugged and highlighted Deedee’s breasts magnificently. I knew it couldn’t be true—I’d seen them in person the day before—but Deedee’s breasts looked several full cup sizes bigger in that dress.
It awakened something in me. I couldn’t go home in two days and never see her again. All I could think about was what she’d look like after another six months of vacation. I’d just proven I could do my job remotely, even in the midst of a crisis. I had to keep this thing with Deedee going. Even if we were just friends, even if I never got to touch her… Seeing her in person was already ten times better than videos on my phone. And while most models or influencers seem like they’d be insufferable in real life or were so performative in their content that they’d be completely different people, Delia was so positive and upbeat that I always looked forward to seeing her, and not just because I wanted to see her.
I watched the video a few more times, then mentally kicked myself. Why the fuck was I watching Deedee bounce off that stone wall on my phone when Delia was just a short elevator ride away?
***
I met Delia in the bar across from our hotel. She did indeed have a head start on me, so I did a shot of vodka and ordered a Cosmo. To my delight, she was still wearing the brown dress. The bar was noisy, but not so loud that we had to shout to be heard.
“How’d your work thing go?” She asked.
“It was fine. They’re all really good at their jobs, so they probably could have managed it without me.”
“That sucks.”
“Eh, it was fine,” I repeated. “I wouldn’t have been much fun to hang out with while all that shit was going on anyway. Answering questions and calls all day.”
“That makes sense. You take your job pretty serious.”
“I guess that’s true. It took a lot of work to get it to where it is now, so it’s hard to… unplug, you know?”
“For sure.”
While we talked, my eyes kept drifting over Delia’s body. I’d never seen her in anything that didn’t show off her spectacular tits, at least a little, but in that dress, they looked gigantic. The material clung to every swell and curve, and I had to force myself to look her in the eyes or pretend to be scanning the room. If Delia noticed my ogling, she said nothing.
“Hey,” she said. “We should go dancing.”
“What? I’m too old for dance clubs.”
Her brows furrowed. “Come on, you can’t be that much older than me. I bet you’re not even thirty.”
“I’ll be thirty in like two months.”
“See? This might be your last chance to have some fun before we have to put you in a home.”
“Wow.”
Delia threw her head back as she laughed, and I couldn’t help but smile. She downed the last of her drink in one long gulp, and as her throat bobbed, I almost thought I could see the sugar and calories slide down into her body and fill out that dress a tiny bit more.
“Come on, granny. Pound that drink, and let’s go have some fun. You deserve it after working so hard all day.”
The club’s music hit me like a wall, but didn’t bother me as much as I’d expected. It was nice not to have the pressure of keeping a conversation going because it was so loud. The thought was absurd; talking to Delia had been effortless since that first encounter. But with the colored lights and the bass thrumming through my chest, I felt free to just… be.
The atmosphere was electric. Beautiful bodies twirled and swayed and gyrated on the floor. Every time I saw her, Delia was full of life, but on the dancefloor, with the music pounding its insistent beat, her whole aura was kicked up to eleven. Her arms flailed, her hips swayed, and her tits never stopped moving. Jiggling, bouncing, wobbling, every motion weaving into the next like a playlist on shuffle. I started out with an awkward white girl sway, holding my drink and making the bare minimum amount of movement to qualify as “dancing.” As the alcohol spread through my system, though, I loosened up.
It didn’t hurt that Delia kept moving very close to me. She wrapped her arms behind my head, grinding her chest against me as she dipped into a low squat. She spun away and thrust her ass into my space, wiggling side-to-side and up and down until I thought I might lose my mind. Her dance gave me confidence, and I touched her lightly as we moved. Tracing my hands along her sides, her arms, mirroring her perpetual motion. As the night rolled on, our bodies spent more time touching or nearly touching than not. Several times, my traveling hands brushed against a bit of Delia’s chest, which spilled wider than her ribs.
She started touching my ass, pulling our bodies together before dancing away. Those grabs were almost enough to take me out of the moment. No amount of compliments from friends and exes was ever enough to make me comfortable with my pear-shaped body. But every time she touched me, pressed into me, gazed into my eyes, she filled so much of my world that there was no space left to think about myself.
My whole body was on fire. Those eyes, those hips, that ass, that fucking dress… And those god damned perfect tits. After one of her many trips down the front of my body, Delia popped up inches from my face. Her eyes bore into mine, deep chocolate pools that pulled on my soul with a force greater than gravity. Her boobs mashed into my chest, her lower body tight against mine. Her eyes darted down to my lips and back to my eyes several times.
She tilted her head, her eyes closed.
I kissed her.
***
When I woke, Delia was still asleep, cuddled beside me. I lay frozen for fear of waking her, but glanced around the room. It looked identical to mine, but with piles of skirts, tops, and dresses strewn over every chair and flat surface. This had to be her hotel room. Returning my gaze to the woman whose sleeping head nestled in the crook of my shoulder, I marveled. Delia’s eyelids fluttered, and I wondered if she was dreaming. I certainly felt like I was in a dream. How had I ever gotten so lucky? I must have been a saint in a past life to deserve this. Or maybe a warzone refuge.
Delia’s eyes drifted open, and as those hazel-browns met mine, her lips curled into a sleepy smile.
“Hi,” I said.
“Hi.”
“I don’t usually—”
She pressed a finger to my lips, then stretched up to kiss me. I tried to ignore how good it felt to have her chest pressed against me. Evidently, we were both naked—or at least topless. Delia gently nibbled my lower lip, then soothed it with her hungry tongue. I thought maybe she wanted to go another round, but then she drew back, breathing hard.
“Breakfast?” I asked.
Her body shifted against mine, and she said, “god, yes.”
Thirty minutes later, we were well into our first mimosas when our food arrived. I’d gotten avocado toast while Delia had a massive Eggs Benedict. With her first bite, Delia’s eyes closed, and she let out a little moan of pleasure. She said, “I wish I didn’t have to go home on Sunday.”
As reluctant as she was for this magical vacation to end, I was low-key desperate. Call it “post-nut clarity,” but I decided to go for it.
“Here’s a crazy idea: What if we don’t?”
She stared at me, eyebrows drawn together. “What do you mean?”
“How often do you travel?”
“Like every other month, or more if I can afford it.”
“Okay, so what if you just… didn’t go home? I’ll come with you, and we’ll just go wherever you were gonna go next, right now.”
Delia let out a delighted laugh. “Wow. I mean, I know I’m pretty good in bed, but I must have really broke you. How delulu would it be to just stay on vacation all the time?”
“Pfft, you’re more conceited than I thought.”
“Be for real; how would we even afford it?”
My heart skipped a beat when she said, “We.” She set down her fork and sipped her mimosa. “Unless you’re secretly a billionaire. In which case, let’s fuckin’ go.”
Now, it was my turn to laugh. “Unfortunately, not. But I think I learned yesterday that I don’t need to be at home to run my company. And I bet if we split the costs, it’d be more affordable than you think. I’ve heard there are all-inclusive resorts that are cheaper than rent and food back home.”
“I believe it. The prices in Canada are literally insane right now.”
“So, what do you say?”
“You’re actually serious?”
“It wouldn’t have to be a big thing. We just go somewhere not too far and try it. Like a week or so? Figure it out as we go.”
“You’re crazy.”
“That’s not a no…”
Her delicious lips parted in a wide grin, the sunlight glittering off the Mediterranean making the hazel flecks in her eyes sparkle. “No, it’s not.”
