Spending the day with Cindy Pt. III
Cindy headed for her next class, which was Math, a subject she was decent at, though not quite a top student, but still, that made her leagues better than yourself, as you often joked that everything past basic Arithmetic made your brain hurt, and even that made you struggle. Cindy was often willing to help you out, even though Zuemy was far smarter, but she only helped you when you were at your most desperate.

But once Jen came along, she was the one who took over helping you with that kind of stuff, though Jen was on pretty much the same level as Cindy. Later, when you met Yamile, you learned that she was quite decent, more proficient at them than both Cindy and Jen though obviously not on Zuemy's genius level, and this had to do with the fact that her mom was a Math teacher, but for some reason Jen didn't seem to like it that you hung out with her...

You were quite comfortable yourself, though initially, you were very nervous and embarrassed, as all that touched you was Cindy's boob flesh, and you had no idea how to feel about it. She seemed pretty chill about it herself, and even told you to enjoy it guilt-free since she made the choice for you, but this kinda served as a sudden reminder that she's a girl... a fact you were always vaguely aware of, but not truly aware of it on the conscious level.

Cindy was actually quite flustered despite having looked much more aloof about it than she actually was, though she was happy it worked. Even if this shrinking thing was quite a tragedy, in a way she appreciated that she'd get to spend some more time with you than you normally would. She also felt something she wasn't sure she could explain, a surge of a protective feeling, but she couldn't tell if that was some form of maternal instinct or some other form of affection for her friend, who was very vulnerable and currently relied on her in almost every way.

She entered Math class and acted as normal, but she couldn't completely tune out the tiny indent in the depths of her cleavage. She giggled quietly, wondering about your reaction when she took you out to ask how it had been in her chest, she was sure you'd blush madly and struggle to speak.

She glanced down at her hips, they more than completely consumed her seat, and a significant bit of her large butt overflowed from it. She knew it was big, though she didn't get to flaunt it as much as Lillian, or even Jen, as she had gotten bolder in recent years. She also lacked Lillian's self confidence while arguably having a chubbier build than hers, which only made her more self conscious. Maybe because of that, she wanted to get you to feel her butt up close, and transportation made about the perfect excuse for it. She knew Celeste had a horrible plan for you in mind, but she couldn't help but wonder if it'd be really that bad if it were her butt instead, and with her being aware of your location.

She listened to the class and took notes, but occasionally jiggled her chest and squeezed it with her arms, but made it look really casual so you wouldn't think it was on purpose, but feeling you engulfed in her chest gave her goosebumps and made her shudder in an enjoyable way. It also served her to try and lowkey test how durable or fragile you were, though she had a feeling you were more likely the former since you were unharmed during her fight with Celeste, which had been a mess.

Time went flying for her, while to you it felt like it was going at a snail's pace, but as you got over the nervousness and awkwardness you first felt, you allowed yourself to relax. Cindy's skin was smooth, smoother and softer than any pillow you ever touched, and the gentle warmth it gave off had a soothing quality of its own. Her heartbeat was also the loudest thing you could hear, as her sizable boobs muffled the noises from the outside enough to be little more than white noise to you, and with all of these things together, plus the shock and fatigue from your traumatic experience earlier, you were lulled to sleep before you knew it.

Two hours later, the class was dismissed as the 'bell' chimed and Cindy got up, grabbing her stuff to go to her locker and get what she needed for her next class, after which, she went to the bathroom and checked that there was no one around before taking a deep breath in relief, as this meant she'd be able to talk to you. With a mischievous smile, she gently reached for you and dug into her cleavage to retrieve you, which was a bit difficult given her size, but that was a 'problem' she was rather proud of. She blushed when she saw that you were peacefully asleep, and couldn't help but coo at how cute that was, but that was enough to wake you up.

"Good morning sleepyhead!" Cindy teased as you yawned and stretched.
"I see that you enjoyed a nice nap" she giggled.

"Well, what else was I gonna do? Math's boring anyway..." You said, as you managed to hear as much.

"Hmm... but that still means you enjoyed your 'ride' in here..." Cindy pointed at her cleavage, pushing a finger into one of her boobs to show off how big and soft it was. You gulped and your reaction made her laugh.
"Relax, I told you you could enjoy it without worry!" She gently poked you.
"But... tell me... is it as good as they say it is in anime?" She asked with a chuckle. Blushing a lot and hesitating for several seconds, you then nodded, much to her surprise and delight.
"Alright! Then, I think that pretty much settles it..."

"What?" You asked, unsure on what she meant by that.

"Your next ride of course!" She happily replied.

"Huh?!"

"What, you thought you'd ride on the booby express all day?" She asked in a mock-stern tone.

"I don't know how you can say those words with a straight face" You said, and she promptly burst out laughing.

"Well... still... do you remember the other choice I offered you back then?" Cindy said after she regained her composure.

"Uh... yeah..." You blushed and looked away. Cindy giggled some more as she patted her admittedly large butt.

"It's time to ride in the 'caboose'" She said with a silly look, she then lowered you and brought you around her waist, facing her immense booty, which strained her jeans to a near unbelievable degree. You gulped quite hard.
"Aww! It's not that big! I mean... Lillian's is bigger... and Lulu's is a lot bigger than that..." She pouted.
"But it's bigger than Jen's, I'll concede" She softly giggled and playfully shook her hips, showing off her big butt's softness and bounce.
"Now the question is where to put you..."

"What do you mean where? I'm guessing your pockets it is..." You said, feeling a bit more confused and nervous.

"Hmm, yeah, I guess I could do that" She said, bringing you right before one of those pockets and then lightly pressing you into her plush flesh, rubbing you on it a little. Even with the tight denim on top, you could still feel a hint of how soft and squishy her butt was. She then raised you and brought you back to her face.
"But I also feel like making a fair comparison, you know?" She then said, and quietly giggled when she saw the confusion in yoir face increase.
"I mean, you rode in my cleavage no problem... so... I think you should go... right between..." She said in a soft, vaguely and ambiguously flirty tone as she brought you back to her immense behind, this time dangling you above her deep crack, which showed as her pants rode a bit low.

"C-Cindy!" You were getting more nervous as she lowered you closer and closer to that dark chasm.

"I really want to know which one's better, my butt or my boobs... I have my theories, but for the first time ever we can get a first-hand account!" She giggled at your expense and once again brought you to her face.
"I'm letting you choose... but you're riding with the 'cushions' anyway" She said, remembering how you called them earlier.
"So, it's gonna be up to you Blaise... where do you want to go?" She said as she brought you yet again before her immense ass.
"Do you want a cozy ride in one of my pockets? I think it'll be pretty tight, but my butt is super soft, you should be fine" She teased before bringing you above her crack.
"OR... would you like to try my 'second cleavage'?" She couldn't help but laugh for a bit after she said that.
"I think this is the luxury ride option, you get to enjoy two 'pillows' that are probably bigger, softer and overall better than the ones you enjoyed before..." She dangled you really close to her crack, and it was pretty much clear that was the option she wanted you to choose, but you were scared, it was even bigger than her cleavage.

"Uhh..." You scratch your head, either choice will make things embarrassing, but what are you betting on? Will you choose the safer option, her back pocket, and feel her plump flesh engulf you from behind until she takes you out? Or... will you take a greater risk for a greater reward, trying Cindy's larger 'cleavage', where certainly no man or boy has ever been before? and also give her what she seems to want... but knowing her, she will probably want you to give her a very detailed comparison between it and her cleavage, by the look of it before.

After a moment of hesitation, you take a deep breath...
173 views
·
May 12, 2023