Day 17 - Monday, November 17th
Freedom. The weekend is finally over. Miles was really on the verge of losing his mind. He spent about 95% of Sunday - hard. It just wouldn’t go down no matter what he did. When Hailey went with her friends, he tried to calm himself down by returning to his jigsaw puzzle. But the moment he sat down his body reacted to the memory of Hailey’s breasts engulfing his upper body, and them having sex on the chair. It felt like less and less places were safe these days. He still had 13 days left, which was less than half. But it was still a long time when you’re this much on the edge.
When he came to class, it felt like people around him were… snickering. It didn’t feel like they were mocking him. Just… that they knew something about him. Something juicy.
He passed by a group of guys on his way to class that he never really talked to all that much but knew their faces from some common lectures they shared. They stopped chatting once they saw him, then they gave him this look. Was it… respect? They closed their mouths and lifted their chins with this weird “yeah man” nod. Miles politely nodded back and kept walking.
There were 4 girls standing in a girls’ power-circle. They were hot, though nowhere near Hailey’s level. No one was on her level. They were all wearing these high boots, mini skirts, and tops showing varying degrees of their skin. Miles’s boob-radar immediately put them all in the range between C-cups and E-cups. His already hard cock jerked in his pants when the first thought that crossed his mind was that - if they summed up the total amount of boobage in this group of girls, they still wouldn’t be able to fill one of the cups on Hailey’s 28(Z)G bra.
The one facing Miles saw him and a mischievous smile trailed up her face. The other girls curiously looked at the direction their friend was looking and they all smiled widely as well.
“Hiiiiiiiiiiiiiii Miiiiiiiiiiiiles”, they said in unison in an over-sweet tone, waving their fingers at him.
Miles’s cock jerked again and he felt a bit of precum escaping it. He smiled shyly, becoming red faced quickly. “Hhhhi…”, he said, before he escaped them and continued walking straight. Their gazes followed him. He heard them snickering and whispering behind his back.
Miles spent his day trying to focus on his classes, and immersing himself in his own assignments in between. It… sort of worked. But he was still hard most of the day. And really - anything set him off. It was ridiculous. Plus, he kept seeing people giving him similar looks throughout the day.
He met Max for lunch at the cafeteria.
“Dude! Wow! Just… wow!” Max said.
“Wow… what? What’s going on?” Miles asked.
“What do you mean what’s going on? Don’t tell me you didn’t see it”, Max said.
“See what?!” Miles was frantic now.
“The video, obviously”, he said.
“What video??”, Miles asked, now becoming really scared.
“Dude, oh my god you’re always so out of touch. The video. Of you and Hailey. At the party…”, Max said.
“WHAT?!” Miles’s heart pumped like crazy. He felt his world collapsing on him.
Max rolled his eyes. “Everyone’s been talking about you two. Here, look…”
“EVERYONE???”, Miles shrieked.
“Miles, come on. Catch up quicker, will ya? Just look”, he said. Max pressed a few buttons on his phone then turned it to Miles. Miles’s eyes opened wide in horror.
Apparently someone was taking a video of their hot make-out session at the party. It showed Miles’s back while a girl’s legs were wrapped around his waist, and it was clear they were dry humping each other. Miles’s face could be seen from the side, though the lighting was bad since it was so dark. Hailey’s face wasn’t shown, but her huge breasts were clearly visible on both sides of Miles’s torso. They really did looked humongous. The video had a caption above saying “Challenge - try watching without getting a boner. Level: impossible.”
Miles was horrified. This was bad. This was really bad. The only saving grace is that the video didn’t show Hailey’s face. But the worst part is that it made him even hornier than before. It really was impossible not to get a boner watching them.
“Sooooo… what do you think?” Max said with a snicker.
“Stop smiling like that! It’s really bad. Shit! What was I thinking… I’m such an idiot…” Miles buried his face in his palms.
“Relax man, it’ll go away. Something else will happen in a few days and eventually everyone will stop talking about this and move on to the next thing”, he said.
“I guess… FUCK!” Miles said, unconvinced.
“And hey, it’s not like it’s an embarrassing video. It’s really hot. Seriously. Everyone’s talking about what a stud you are to land such a hot girl”, Max said.
“Fuck… I don’t care about that. I care that Hailey will get heat for it”, Miles said.
“No one can see her face though”, Max offered.
“Oh yeah, and it’s really difficult to narrow down the list of girls with boobs as big as beach balls”, said Miles, feeling lost.
“They’re really that big?” Max’s eyebrows lifted.
“Bigger actually…” Miles said with a groan.
“Oh my g…”
“Focus, Max. Please, what am I gonna do? I don’t want Hailey to get hurt”, Miles pleaded.
“Hurt? The only thing everyone’s saying is how hot she is. All the girls are jealous of her, and all the guys are drooling over her. The thing people actually said the most was ‘how did Miles manage to not cum on the spot?’, which I admit - I was one of those people”, Max said and raised his palms defensively.
“Ugh… I’m wondering that myself as well. Shit…I gotta go”, Miles said.
“But… what about our food?” Max said.
“Go ahead and eat, man. Send me that video. Sorry, I gotta talk to Hailey”, Miles called back at him as he started walking fast.
*
Miles paced nervously near the entrance of the small, empty room. It used to be the old Chess Club, but it had stayed abandoned for six years after the club moved to a new location. Hardly anyone even knew it even existed, which made it perfect for what Miles needed now. He finally heard quick footsteps and looked to the end of the empty hallway.
Hailey’s form appeared, dressed to kill as always. Even from afar he saw her wide, loving smile. She wore high heeled dark brown boots, see-through leggings and a short, tight, black pencil skirt that reached her mid-thighs. The skirt was so short, in fact, that Miles was barely able to see it. Her gigantic boobs now grew so big they covered more than half the skirt. They bounced and jiggled like crazy in a skin-tight, long-sleeved sweater that had a zipper all the way to the bottom. The sweater only reached her sternum level, leaving her upper chest and shoulders completely bare.
Miles’s eyes followed her boobs with hypnotized eyes as they bounced madly with each step she took. That zipper looked like it was holding on for dear life. Hailey’s boobs now projected about 2 whole feet in front of her. He stopped asking how the hell she even found clothes that fit her crazy frame and just assumed it was Zina’s hands doing magic.
But the cleavage…
Hailey wore her black 28(Z)G bra, and it was clear she was right. She really did have a single day where it fit perfectly. Despite his anxiousness, Miles’s cock stirred to full rigidity upon seeing the over-a-foot of cleavage jiggling and muffining above her bra and out in the open. How did car accidents not constantly happen around that girl? Miles remembered how despite Hailey’s previously huge size, the bra had been too big even for her a few days ago. So how the fuck is it already too small?? A small child could curl and fit in each cup! Yet it still wasn’t enough for her boobage.
“Hey babe”, She chirped casually with a wide smile when she finally reached him. “What’s with all the secrecy? Couldn’t wait to see me before the day ended?” she asked and approached Miles seductively, mashing her boobs into his chest.
Miles however, looked left and right before he put a finger to his mouth, opened the door to the old Chess club and guided in by gently pulling onto her lower back with his arm. An excited shiver ran up Hailey’s spine. She so loved it when he was doing these manly things, like guiding her or opening the door for her. Made her feel like a pampered lady. Plus, she felt like they were actually on a secret mission, which to her - was a game, which - she was always up for and went along with happily. Miles stuck his head back out to make sure no one was there before he closed the door behind them.
He turned back around to face the room, only to find Hailey beaming with excitement, standing a foot away from him and pushing his back against the door. Which meant that what should have been her second-foot of her boobs’ projection, was instead directly smothering his chest and arms. He was basically trapped and couldn’t move his arms, so all Hailey saw in front of her was his cute head and shoulders emerging from above her ginormous, soft tits.
“Oooo I’m so excited, baby! What are we doing here? Are we playing detectives or something? What’s our mission? Am I your sidekick? Or your side-chick…? I hope for your sake I’m not!”
“Hailey!” Miles whispered with urgency in his voice. God he was so cute when he was serious.
“Sorry, captain. I’m all ears”, she tried to be serious but couldn’t keep a straight face looking so close at him like that. She made sure to lean forward some more to “be more attentive to what he had to say”, and certainly not to drown him in a sea of tits.
“Hailey, this is serious”, Miles said urgently, though his body couldn’t not indulge in the wonderful feeling of those soft mega-mamms smothering him. Annoyingly, his dick was throbbing. Hailey snickered a laugh.
“I’m sorry, babe. You’re just so funny saying this is serious when your arms are trapped like that under my boobs”, she said and giggled. Miles took a second and had to admit this was kinda funny.
“Hailey please. Did you see it?” Miles asked.
“See what?” she asked, curious.
“The video. Our video”, he said.
“Ohhhhhhh that? What, from the party? That was so hot, wasn’t it?” she said with a mischievous smile and shook her shoulders excitedly.
Miles was shocked. Not only did she not mind the video… she actually… liked it?
“I… I don’t understand. I thought…” he said, confused.
“What?” she raised her eyebrows.
“I don’t know… that it would bother you. That you might be embarrassed or something”, he said. This was weird. He felt like an inner voice has been constantly feeding him lies for the past couple of hours just to mess with his head.
“Why would I be embarrassed about it? Do you think I have something to be embarrassed about?” she asked and now pushed him strongly into the door. Her boobs rose up to his chin. ‘Fuck, she could make an excellent FBI interrogator’, Miles thought with panic.
“Nnnnnno! No, of course not. It’s just…I don’t know. It was our private moment, and now everyone knows about it and it’s not private anymore”, he said as fast as he could, sweat forming on his forehead. Jesus, she could be terrifying sometimes. Hailey was partially satisfied by his answer and eased up a little on her boob-hold, though he was still trapped. Miles continued:
“I’m just not used to all this attention. It’s weird. Today guys kept giving me this… look. And girls kept um… hitting on me. Which I of course turned down immediately!!!” he clarified quickly.
Hailey bit her lower lip with a smile.
“Well, of course they were hitting on you. Did you see what a stud you were in the video? I’d hit on you with everything I had if I was them. It was so hot seeing you making my legs shake like that while humping me again and again. Plus I just loved seeing you being wrapped by these monsters like a cute pig in a blanket. Or, a cute stallion in a blanket, actually”, she said and emphasized by bouncing her right and left boob alternately from below. Miles felt the strong ripples traveling up to his chest.
Miles blinked, trying to process it all.
“So… you don’t mind that everyone saw the video?” he asked, and couldn’t help feeling a huge weight lifted off his shoulders. Though an equally-huge weight was pushing down on his torso right now…
“Mind?” she asked, then leaned way forward, smothering him more than ever before. She got as close to his ear as she could, before she whispered: “I fucking loved it, baby.”
Miles felt his erect dick being softly engulfed by the undersides of her gigantic boobs. So many emotions passed through his body right now. He didn’t know what to make of them all.
“I understand, though”, Hailey said, still close to his ear. Her voice softened and was more empathetic now. “You’re probably not used to so much attention. For me it just became white noise at some point. I’m used to always having everyone staring and whispering about me by now. It used to bother me when I was younger, yes, but now - I love it. Some girls will always be jealous, and the guys… well, you know guys.”
Miles nodded in agreement. He felt a hand creep down and hold his rigid package through his pants. His eyes opened wide. Hailey now whispered into his ear while she started massaging his cock and balls through his jeans in slow, sensual motions:
“But it really excites me to know those guys would all love to be in your place, and I get to tease them and show them you’re my stud. To make them all drool while you make me cum. To smother your body with my giant boobies and make them all wish they could be you. To know they’re probably jerking off to me, but you get to take me home and fuck the living shit out of me, to make me cum over and over and over and over and OVER AND OVER AGAIN AND AGAIN…” she said and emphasized each ‘over’ with a synced massage to his hard cock.
“Ohhhhh fuck… Hailey I…”
“Well… maybe not right now, I guess. But you’re getting really close. You only have 13 more days to go, my sexy stud. I know you can hold off cumming just a little bit longer”, she said. Her hand moved up the hem of his jeans and now entered inside his underwear. She grabbed his HARD dick that was spewing pre-cum held it in place. It was actually quite slick from all the precum that escaped it. She pushed forward as hard as she could, making her boobs reach Miles’s mouth!
“You know… that video was so hot, I took it into the girls’ bathroom today and got off on it”, she purred into his ear.
Miles’s eyes were opened wide.
“Oh god…” he said.
“I came again” she said and did her magic screw twist motion to his cock with her hand. “Oh fuck!”Miles groaned.
“And again”, she twisted again. “Jesus Christ, Hailey!”
“And again”, she twisted once more. “Shit I’m so close, Hailey”
“And then… again”, she gave another sensual twist. “Fuck FUCK FUCK FUCK FUCK FUCK Hailey stop I’m about to cum”, he said in panic. He clenched his ass with everything he had within him to stop the flood of cum from rising. Hailey stopped moving but held his cock firmly. However, she smothered him into the door with all her might and passionately kissed him while holding his dick.
His dick did something it never did before. It came, without cumming. The muscles underneath his cock strongly spasmed involuntarily over and over again and gave him a sort of a new thrill he’d never experienced before. Miles kept clenching as hard as he could, praying that the storm would pass without an accident. As Hailey kept kissing him with intense passion, Miles felt the chills and thrills going through his body as if they were an actual orgasm. He didn’t understand what was going on, besides the fact that it felt amazing.
He rode out his un-cumming orgasm for like a minute before he finally felt it die down. He couldn’t explain it, but it now felt like he could go on for a bit longer before he needed to cum again. It was almost like a little cheat code he discovered.
Hailey parted the kiss softly but stayed close. She looked at him hungrily.
“That was so fucking HOT, Miles. I felt your hot cock spasm in my hand. Miles didn’t know what to say. He was stunned.
“You know… those masturbation sessions in the bathroom didn’t help at all. I’m still so horny. I need you, Miles. I need your beautiful cock baby”, she said with an aching need.
Miles didn’t have time to realize what was happening. All he knew was that his dick was quickly pulled out of his pants and Hailey’s bare pussy clung to its head. He felt her sexy panties to the left of it.
“Fuck me baby. Fuck me right here. Just a little bit”, she said with a tease. Miles was almost furious. That fucking hot bitch was using his little stunt against him. But he was too fucking horny to be mad.
He felt her pussy opening touching his cock head. It was so wet and hot.
He looked at Hailey, Hailey looked at him and they both knew this was inevitable.
Then he shoved it all the way in. It entered smoothly. It was obvious her vagina was ready for his cock. No foreplay needed this time.
“AHHHHHHHHHHHHHH!!!!!!!!” she screamed and her eyes rolled back.
Miles felt like he still had some stamina within him. He pulled back slowly, then shoved his cock back in, as hard as he could.
“AHHHHHHHHHHHHHHHHHHHHHHHHHH!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!” She screamed even louder.
He pulled back and shoved again, drilling his cock like a police battering ram.
“AHHHHHHHHHHHHH I’M CUMMIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIING”, Hailey screamed so hard Miles was afraid someone will hear them. He kissed her passionately and she automatically kissed him back even more passionately. She felt her already strong orgasm only gaining more strength.
Miles shoved it again, and again and again, bringing Hailey to ever higher crests. She cried out passionately into his mouth and her eyes almost made a 360 roll in her head. She’s never cum this strongly. She obviously needed this really bad.
Miles managed to keep blasting his cock into her pussy for over a minute, bringing Hailey to inhuman levels of ecstasy, and making her squirt torrents of girl-cum onto their legs, before he again felt the familiar tingling in his balls. Thankfully, this was just as Hailey started coming down from her double-digit orgasm.
They both panted. Hailey looked at him like she wanted to become his sex slave and worship him for life. She kinda did, actually. Miles was just stunned. Mostly by the insane heights Hailey’s reached, but also by himself.
“Hailey…”
“I love you so much, Miles!” She said frantically and kissed him with utter devotion. His dick lurched in her hot, tight pussy.
After another long minute, he softly broke the kiss. “I love you too, baby”, he said.
Miles pulled back slowly. Hailey finally released her boob grip on his body and allowed him to awkwardly put his dick in his pants, while bulging above its hem.
“I gotta get to class, baby. See you later tonight?” he asked.
Hailey was enamoured with him. She nodded submissively.
“Yes. My super sexy, masculine, hot, PUSSY WRECKING STUD!!!!”, She said in the sexiest voice ever and really wiggled her shoulders aggressively so that her long, exposed cleavage of boobs jiggled like crazy in front of his hungry eyes.
Miles almost came just from that gesture.