Day 16 - Sunday, November 16th
Miles woke up with the most raging boner so far. He felt like his cock would explode any second now. He held it firmly in his hand to try to control it. It was so pumped up with blood it felt like holding a pillar made of cobblestone.
“Ohhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh fuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuckkkkkkkkkkkkkkkkkkkk what am I gonna doooooooooooooooooooooo…”, he groaned at the ceiling in a low voice. He rolled left and right on the bed while holding his dick in his hand. The only thing he wanted to do was pump his hand up, but since he couldn’t, he just squeezed it harder. It didn’t really help but it was the only thing he could do.
Yesterday was a turning point as far as Miles was concerned. He had sex with Hailey. True, it was… very short, and very unsatisfying, at least for him, but sex nonetheless. He crossed a threshold he thought shouldn't be crossed during this stupid NNN challenge, and now he was paying the price for it. He could also not help but wonder if he now opened a Pandora's box he wouldn't be able to close. Is this the new status quo between Hailey and him? Little sex sessions where Hailey cums her brains out and he's left with his dick in his hand? FUCK!
Hailey was already up, doing her morning jog/walk, which was more of a walk than a jog at this point, given her size.
Miles kept having sexy dreams last night about Hailey and sex and boobs and cumming and more sex and kissing and making out with a Hailey, smothering him with her boobs on all sides. The funny thing was, his dream wasn’t that far off from reality. Except for the cumming part.
He rolled to the side and his face landed on her pillow. He instinctively smelled it. It smelled so good, having remnants of the alluring, feminine smell of her hair. Of course it did. “Mmmmmmmmmmmmmmmmmm I wanna fucking cummmmmmmmmmmmmmmmmmmmmmmm!!!!!!!” he groaned again into her pillow and just stayed there, face down, wearing only boxer's underwear, his hand in his boxer's holding his dick firmly.
He really was a wreck by now. He wasn't usually a guy with a sense of self pity, but this time he actually felt that. The thought “poor ol’ me” actually crossed his mind once. It first made him giggle and then almost cry.
He stayed like that, face down on Hailey's pillow, his knees folded into her chest, dick in his hand, until he drifted off to sleep again.
Hailey got back from her light jog.
“Hey babe!”, she called cheerfully into the apartment. She was full of energy. She loved a good morning workout. Plus, she just felt extra cheerful today, she wasn't sure why though.
“Miles? Baby?” She called into the hallway. Curious, she walked to their bedroom only to find Miles in his shameful fetal position, asleep.
She had to stop herself from bursting out laughing and managed to only slip out a quiet snicker. He looked so… bad. But so cute.
Hailey entered and walked next to him. She only now saw that his hand was holding his stiff cock. Hailey bit her lower lip with a mischievous smile. How she wanted to replace that hand and shove that hard cock into her wet mouth. She was becoming very aroused just thinking how even in his sleep he was hard.
But she decided to give her poor boyfriend a little break and went to take a shower.
Miles kept having more sexy dreams about Hailey and her gigantic breasts enveloping him. His cock involuntarily jerked in his hand, as if begging it to take care of it. He dreamed of heavy, soft pillows caressing his back, smothering it and enveloping it on both sides. It just felt so real. So good.
He felt a small kiss on his upper back. Then another kiss and another. He suddenly stirred in his sleep. This felt… too real. It was real!
He slowly opened his eyes, though he could still barely see anything since he was face down into the pillow. But he definitely felt something. Two somethings.
Starting from his lower back and its sides, two soft, warm and heavy somethings rubbed and smothered against his body. They then continued to engulf more and more of his body, going higher to his mid, then upper back until they reached his shoulders. Due to his awkward position, they also reach low enough to smother his folded legs as well, basically trapping him from shoulders to toes.
“Ohhhhhhhhhhhhhhh”, he groaned in pleasure, still not fully awake and just enjoying the blissful sensations engulfing his body all around. They were so wonderfully soft and heavy.
“Mmmmmmmmm good morning, my love”, he heard a familiar voice purr into his ear.
Miles stirred awake and opened his eyes. It all returned to him. He panicked, but his body wouldn’t allow him to move. It all just felt too fucking good. He smelled Hailey’s feminine, fresh smell after her shower and his dick jumped in his grasping hand. Everything around him was soft and soothing and so fucking arousing. But most of all, he understood one crucial thing - Hailey was completely naked.
Hailey was hovering above him, allowing her soft but firm breasts to engulf most of his body. It turned her on so much, knowing she could do that to her sweet boyfriend. Despite their immense weight and size, her boobs had an inherent cleavage even without a bra on. So the inner parts of her boobs were also smothered against his back as well.
She hovered with her torso a few inches above his back, and moved back and forth. Her heafty, gigantic boobs moved like giant pendulums against Miles’s body, caressing him over and over again.
“Ohhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh goddddddddddddddddddddddddddddddd Hailey aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa”, he groaned quietly and felt his dick pumping with more and more blood. It felt like holding a rod made of pure diamond in his hand.
“You just looked so cute I couldn’t not say hi”, she leaned right into his ear when she purred sensually at him. Miles shivered in response, which made Hailey smile victoriously. She loved having so much effect on him.
“Hiiiiiiiiiiiiiiiiiiiiiii”, he groaned back in blissful agony. Hailey bit her lower lip.
“I had such a great morning workout babe”, she kept purring softly right into his ear.
“Mmmmm hmmmmm”, he moaned helplessly. Fuck he wanted to cum so bad.
“But you know”, she said in a mock-frustrated tone. “It’s getting harder and harder to run. My boobs just keep growing, and growing, and growing, and GROWING. I don’t know what to do. They jiggle so much when I run. Back” she said and moved her breasts back, which made Miles groan.
“And forth”, and she moved her breasts forward, and Miles groaned again.
“Back”, she moved again and Miles groaned louder.
“And forth.”
“Back.”
“And forth.”
Miles was shivering all over and groaning in agony. This was the most epic massage he ever got. A boobs massage. A MASSIVE-BOOBS massage. This was heaven and hell simultaneously.
“Plus”, she continued purring into his ear. “It’s getting harder and harder putting on my sports bras. The 5XL barely fit today, and the 4XL almost exploded. Do you think they sell 6XL? But no, actually, the 5XL only covered like a third of my boobs. Maybe I’ll get an 8XL? What do you think, babe? Do you think it can cover these babies? I’m not sure even that would be enough to cover these babies” she said, and with that she hugged her own breasts inwards and really smothered Miles on all sides.
“Ohhhhhhhhhhhhhhhhhhhhhhhhh my godddddddddddddddddddddddddddddddddd”, he groaned and his eyes fluttered upwards.
“Oh, by the way, here…”, she said and placed something on the pillow next to Miles’s face. He looked at it and recognized it immediately. It was their tape measure. His dick jumped again in his hand.
“I can’t use it anymore. I tried measuring myself now in the bathroom and was a bit short. Can you imagine? A 5-feet long tape measure is now not enough to measure me. Good thing I got from Zina her 8-feet long tape”, she said in a relieved tone. A little precum shot from Miles’s cock upon hearing that.
“Do you wanna know how big I am today?” she asked nonchalantly.
Miles didn’t know if he wanted to know the number or not. It was like he was simultaneously trying to both enjoy this and hurt himself. Hailey didn’t wait for an answer, though.
“I’m 61 inches around, Miles. 61 inches”, she said. Miles groaned loudly.
“That means my 28(Z)G bra fitted perfectly today. It was so great. I put it on and it actually fit, then over it I put my 2 sports bras but these boobs still jiggled like hell. Anyway, I’m so excited, babe. What do you think?” she chirped and shook her shoulders left and right, which made her boobs swing over and over again into Miles, making a loud thud sound each time.
“Ohhhhhhhhhhhhhhhhhhhhhhhh”, Miles again groaned. He was helpless. She was just so many orders of magnitude stronger than him sexually. He had no chance to do anything but sit and take whatever she lashed at him.
“Yeah, I know, you’re right”, she kept having a solo conversation with herself. “It probably won’t fit by tomorrow already. Such a shame. It’s like those trees in Japan that bloom for only like a week or two in a year. Damn, I forgot their name…”
“Cherry Blossom”, Miles groaned in a what-the-heck tone.
“Yeah! That’s the one, thanks babe, you’re so smart!” She said and kissed his back, which sent a shiver throughout Miles’s body.
“So this bra is like the Cherry Blossom season. Just think, babe, I was 58 inches 2 days ago, and now I’m 61. That’s now an inch and a half a day!” She squealed with excitement.
“Ahaaaaaa”, agreed Miles as he felt himself drooling on Hailey’s pillow.
“I hope they're not too big for you, babe. What do you think? Are they too big?” She asked with some concern. She leaned forward and hugged them again into Miles’s body, making them balloon all around him.
“Aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa”, he groaned.
“I knew you’d be ok with them. But let me know if you think they’re getting too big for you, ok babe?” she said sweetly into his ear.
“Aha”, he drooled.
“I love you so much, Miles! You’re always listening to me talking and talking forever and you’re so patient”, she kissed his cheek, “and attentive”, she kissed him again, “and thoughtful”, another kiss, “and supportive”, another kiss, “and loving. You’re the best boyfriend ever”, she kissed a long smooch again on his cheek and hugged her breasts into him with everything she had within her for a solid minute. Her breasts muffined and smothered him all around his body.
Miles almost fainted from stimulation overload. His dick spewed so much precum it almost equaled to an actual load.
“Ok babe, I’m gonna get dressed and then I’m meeting the girls. We have this annoying group assignment we have to get over with for next week. See you tonight. Bye baby. God you’re so fucking cute!!!!” she couldn’t contain herself and smooched his cheek again before she got up and left Miles in the same position, his dick in his hand, spewing precum.
“Aha”, Miles groaned back into the pillow long after Hailey had left the room.