Day 1 - Saturday, November 1st
Miles woke up surprisingly refreshed.
For a moment, he even forgot about this stupid bet he’d made with Hailey last night, until she entered their bedroom.
“Good morning, babe” she sang, her voice bright and full of energy.
She was holding a coffee cup in each hand. Hailey wore a fitted white spaghetti strapped tank top, paired with a pair of shorts which showed off the majority of her toned, shapely legs up to her mid thighs. The tank top, despite being XXL, was taken up almost entirely by Hailey's massive juggs jiggling within, looking as full as ever. It clung to them for dear life, clearly still inadequate at containing them properly despite its large size. Hillocks of breast flesh crested in great volume above it, the spaghetti straps digging into them as a result. Her sturdy bra was at capacity, despite its immense size.
Miles recalled he'd once secretly snooped around Hailey's closet while she was away, a few months into their relationship, taking out her immense bra and trying to fit various objects into its cups. Apples were a drop in the bucket, as well as oranges. Even honey dew melons fit with a lot of room to spare. Desperate to find something to challenge this bra, he brought his size 10 basketball. Yet, even that fitted into each cup with some room to spare. The straps were so thick, yet somehow worn out, like they carried a heavy load each day. He counted 8 hooks in the back, it was insane! His dick had been rock hard by that point, as he then checked the tag. 28S cup. Fuck! He couldn’t stop being shocked at how such a slim girl could have such an outrageously gigantic bust. She wouldn’t look out of place in any Anime or Mange show with those exaggerated figures of slim, super-busty girls.
Looking back at Hailey's sexy form in their bedroom now, Miles sat up in bed and forced a yawn, trying to seem casual. However, he already felt his dick hardening.
“Morning,” he grumbled, rubbing his face. “Why are you awake?”
“It's 10AM already, sleepyhead,” she said cheerfully. “And I wanted us to plan our day together.” She made her way closer to him, her breasts jiggling madly with each step. Miles couldn't help but follow those jiggles with hypnotized eyes. God she was gorgeous, with those big, blue eyes, that lustrous, abundant hair. But fuck, her boobs were just… errrrm!
He intentionally looked away and nodded, maybe a little too confidently. “Sure. Totally. We should… plan.”
“Here, I put extra creme like you like”, she handed over his coffee.
“Aww, you're the best”, Miles said and reached his hands to grab the cup from Hailey's hand. However, she lowered way more than necessary, reaching a straight angle before handing the cup over to Miles. As a result - her cleavage deepened enormously. Miles’s eyes opened wide as a sea of breasts unveiled in front of his eyes. His mouth opened wide and he forgot to blink.
“Babe?” Hailey asked, smiling knowingly.
“Huh?”
“Your coffee…”
“Oh… yes, coffee, thanks”, he grabbed his coffee cup and was about to take it when Hailey suddenly inched herself closer and absent mindedly touched her cleavage to the back of his hands.
Afraid, Miles quickly took the cup and focused as hard as he could on drinking that coffee and nothing else. Hailey took another moment to softly jiggle her heavy breasts before straightening up. Miles felt his dick now fully hard underneath the covers. The only thing he wanted to do was reach out, maul these breasts, grab Hailey and ravish her sexy body. Usually they'd use Saturday mornings for a fun fuck session, but now Miles couldn't. He had to unnaturally resist his urges. ‘Shit, this is going to be harder than I thought. And it's only the morning of the first day!‘ He had to keep his shit together.
Hailey sat down on the bed next to him, making her breasts shake madly in the process. Her shoulder was brushing his. She pretended not to notice Miles's hungry eyes following her huge breasts' every jiggle and shake. She took a sip of her coffee, “So… we have no classes today, but we both have some assignments to get done. How about we have breakfast, then you do your stuff, I'll do mine? We can grab lunch later.
“Uh, yeah, lunch, yeah, sure, yeah” Miles repeated, trying to force his brain to focus on his assignments and not the very distracting, massive watermelons in Hailey's tank top. “Yes. Lunch is good.”
She flashed him a grin. “See? You’re already doing better than I expected. This month should fly by easily for you. I'm sure you can do this, babe.”
“Ha. Ha. Yeah…”, he said nervously. He wasn’t sure what game she was playing, encouraging him like that, but he was extremely suspicious of her.
“Come on. Shower, breakfast, study. Easy.”
She planted a wet, sensual kiss on his cheek, then lovingly gave two gentle pats to the bulge tenting his blanket and hopped off the bed.
“Hailey!” he warned.
“What?? I’m just being friendly”, she said innocently. However, that playful, wicked sparkle in her eyes said otherwise.
Miles thought he was going crazy, but he was sure Hailey was messing with him all day long. It felt like every little thing she’d been doing was intentionally sexual. At breakfast - she hummed joyfully after every spoon of her cereal she put in her mouth. When they sat together in the living room to finish their tasks, each on their own laptop, she kept adjusting her top or stretching exaggeratedly, thus pushing and further emphasizing her huge juggs for his hungry eyes to feast. She kept approaching him and asking random questions where she’d get very close, put her hand on his shoulder or back and lean forward, almost “accidentally” touching her breasts against him.
After two hours of study, Hailey pushed back her chair. “Gotta stretch my legs.” Miles nodded, grateful for the breathing room, but Hailey didn’t walk away. Instead, she stood right beside him, peering down at his laptop like a curious cat. “Show me what you’re working on.”
Miles felt her breasts mash into his back for about the tenth time that morning and breathed in and out heavily. He explained the code… badly… while trying not to think about the fact that she was close enough for her perfume to hijack his brain. He closed his eyes momentarily and relished the soft feeling of her breasts on his back, before opening them back up in panic. He felt his dick throbbing.
“Miles?” she said quietly, “you okay?”
“I’m fine,” he lied.
“You sure? Because your ears are very red.”
He slapped his hands over them. “No they’re not.”
“You’re so adorable when you lie,” she teased.
Lunch was no better, with Hailey having placed her huge boobs on the table of the restaurant and leaning forward multiple times during the conversation to grab the salt or whisper something to Miles, and causing her cleavage to further bulge in front of him. Miles did his best to stare at his plate, even when it was empty, or admire the dull decor, but it was impossible not to be bombarded by the view of Hailey’s massive tits bulging at him.
Hailey found out she was really enjoying this. It seemed silly at first, but seeing her cute boyfriend being tormented like that, knowing she has that power over him was so exhilarating to her. Sure, she’d love to have her usual sex sessions with him, but there was something else about this whole bet. Something way more fun. And she had the whole month to keep exploring ways to torment him. Yay!
Somehow Miles made it through until dinner. They made dinner together — pasta alfredo. After being scolded by Miles, this time Hailey genuinely behaved. No “accidental” brushes, no bending over too slowly, no implied threats. Just a couple cooking and laughing and trying not to burn things.
When they finally settled on the couch to watch their show on Netflix, Miles felt… almost normal again. ‘I’ve got this’, he thought. ‘She’s not invincible. I can handle her.’
Then Hailey yawned and rested her head on the indent under his shoulder. Her right breast mashed soothingly against his side. It was so big it touched from underneath his armpit down to his hip joint.
“Tired?”, asked Miles, not daring to look at her.
“What? No no, I’m ok. Just… making myself comfy”, she said sleepily and scooched back and forth to try to find a good position.
Miles’s hands were on the back of his head, making sure not to touch anything. It would’ve worked if not for Hailey’s arm to then also hug his waist. Her right tit was mashed more forcefully against his side, and her left tit smothered his left thigh. His cock was tenting his pants, mere inches away from either boob, calling out to him to grab it. Miles took a deep breath, closed his eyes and exhaled slowly and quietly. ‘FUCK this is HARD!’
He didn’t take the bait. Not tonight. His cock was yearning to be touched, but he didn’t dare do anything.
It was an hour and a half of pure bliss and torture. He couldn’t help enjoying the feeling of constant, soft pressure from Hailey's pliant boobs against him, but he also couldn’t do anything about it. But eventually - Miles made it through. As the credits rolled on the movie he barely paid attention to, Hailey awoke with a start, groggy.
“Mmmmmm…”, she purred sleepily. “Was the movie any good?” she asked.
“Uh… it was nice”, Miles lied.
“Ok. I’m going to bed, baby. Are you coming?” she asked.
“I’m uhhh… gonna take a quick shower first. You go ahead, good night”, Miles said.
“Ok, babe. Good night”, she said and gave him a loving kiss, which made her breasts get smothered even more forcefully against his body. She then wandered off to their bedroom and fell asleep almost immediately.
Miles stayed there on the couch for another minute, just breathing deeply. In. Out. In. Out. His dick was still hard. He looked at the ceiling and sighed heavily as he did his best to ignore his most basic instinct to jerk off right now. Then he got up to take a cold shower, which sort of helped his dick to finally soften, although he still felt this general sense of pent up arousal. He went to bed, looking at the two massive hills on top of his gorgeous girlfriend’s form and then shut his eyes forcefully. He put his two hands underneath his pillow so they wouldn't wander off by themselves and forced himself to go to sleep.
He survived day 1. Barely.