A few minutes earlier, in Alisha's classroom...
It had been a couple of minutes already but Jade didn't mind. She was rather lazy when it came to school so she didn't care that much about arriving late, plus she could easily get excused by Alisha's request to help with Shirley's punishment, who remained imprisoned inside Jade's truly enormous ass. She kept struggling frantically as she was revolted by Jade's trapped sweat but all she managed was to unknowingly give her a pleasant mini massage.
Jade wasn't listening in but even with the door closed, she could at least hear that there was some kind of conversation going on. Once things went silent, she waited for a bit before slowly turning the knob and walking in.
Just like when she had sat on you before, you didn't fully understand what Alisha's aim was with this test and there wasn't too much that you could do about it anyway. Looking at things on the bright side, you tried to get comfortable as her generously sized bosom thoroughly engulfed you. The thing you found strange is that she was giving you similar vibes to those of your own mom, but whether that was a good or a bad thing was also anyone's guess.
Alisha sat comfortably in front of her desk and finished some paperwork. The workload wasn't nearly as great due to the lack of homework to grade but she didn't mind as much either way. She hadn't lost track of you though and was pleased to find that even with a bust as large as hers, you appeared to be not just completely fine, but comfortable even. Still, she lost her focus for a moment when the knob turned and Jade slowly walked in. It was only a split second startle but she got startled nonetheless, so subtly that nobody would've noticed.
"Oh, Ms. Galewind" She said, quickly regaining her composure "Apologies for the wait"
"Don't worry Mrs. Kshatriya" Jade smiled. Given her not-so-stellar academic record back in her previous school, it was best for her to try and befriend as many teachers as she could anyway though in this case she sincerely appreciated her.
In her previous school there was a Zero Tolerance policy that punished both parties on any given incident, causing her even more trouble than she would've already faced ordinarily. For Gulliver High, it was a fortunate turn of events that as soon as young Principal Abalos was appointed by the city's Mayor herself, the very first thing she did was to completely abolish that policy and rewrote school rules from the ground up.
"As you may have guessed already, I'll be tasking you with administering extended punishment to Shirley for her actions during our last class. But do bring her back to me at the end of the school day, understood?"
"Of course, ma'am" Jade smiled. Alisha thought she'd go on her merry way but upon noticing that the large goth girl lingered around she wondered why and it didn't take her too long to figure out, glancing at the hour on her phone's screen, which was on her desk.
"Oh, I see. You must need a pass to cover for this little bit of tardiness" She said, quickly pulling out a small piece of paper from a large bunch of them and quickly filled it out. She then grabbed a different paper and also filled it out.
"This one's a written authorization for enforcing class punishment. It stands in for detention..." She explained, but then gave Jade a slight smirk "If Shirley were to lose that paper, she'd have to face detention all over again after classes are over"
Jade giggled and her eyes lit up. Not only she wanted to get revenge on Shirley, but in some ways she also wanted to avenge herself for all the past grievances she suffered in her previous schools, half of which were caused by Gullie students.
"You could say that it got misplaced but keep it on yourself just in case, it'll serve as your legal defense in case Shirley tries to stir something" Alisha added. Jade noted that the way Alisha said the Gullie girls' name carried a hint of disdain and that she had dropped the more formal addressing for her. Even if she didn't have anything against Gullies, it made sense that Alisha would deem students incurring her wrath unworthy of her basic respect, a position Jade could easily agree with.
"Thank you so much, Mrs. Kshatriya" Jade then left the room, looking forward to making her tiny captive's life hell. Lunch had been fantastic, as a big fan of Mexican food herself and she hadn't thought that she'd get to eat fresh, authentic versions of her favorite dishes on the regular but it'd still take a couple of hours for their full effect to kick in.
With her gone, Alisha unbuttoned the first few buttons on her blouse to reach into her cleavage, carefully fishing you out with two fingers. She brought you to her eye level and examined you, seeing no signs of discomfort nor being hurt, though you looked a tad disheveled due to the immense amounts of womanly flesh that had been enveloping you whole for a while, which brought a subtle smile to her face.
"I'd say our second test is a success as well. And I'm no slouch up here for that matter either" She said "How was it for you?"
You immediately blushed. It had been a surprisingly pleasant experience but it felt awkward to tell a woman how staying between her boobs was. Jen had already gotten into a similar predicament, with the added concern that she's a really gorgeous girl you're attracted to, and even then she still got you to admit you enjoyed it in the end. Your mom and your big sis had given you plenty of unintended "practice" with their own antics and even others like Dolores and Arianna had placed you on their massive chests at times but it was never easy for you to recount what the experience was like.
"I see, that look speaks volumes" She chuckled, making you blush harder.
"Not so many young ones would've felt as comfortable with a lady as old as I am" She added, sounding like she was speaking more to herself than to you.
"Y-You look great...!" You blurted out but almost immediately regretting it.
As soon as you heard her calling herself odd, there was a quick debate in your mind and the option to reassure her trumped over the keeping quiet one. Definitely a side effect of growing up raised by your mom. When her eyes focused on you, you couldn't help but panic and even flinched in response.
Alisha, however, only found this even more endearing and cute. Even more so because she saw through your reaction and could tell that this wasn't the first time you'd reacted like this, further cementing her previous assumption that you'd been raised by a Brob woman. Even if you hadn't told her, this would've led her to believe that not only you'd been raised by one but that with near complete certainty you were the son of one.
"Thank you" She smiled "The pure sincerity in that response only makes me even more curious to meet the fine lady that did such a superb job raising you" She said, half-jokingly. She made a mental note to ask for a teacher-parents meeting as soon as it was reasonably possible. Unable to give a proper answer, you simply looked away while trying to wait out your embarrassed blush to wear off.
"Also thank you for entertaining these personal tests of mine. We're almost done, we just need one more. It could get a bit rough but I trust you'll be just as capable as you've been so far" She said and with that, she began lowering you down but this time her hand went below her chest level, that alone was enough to worry you but when you saw that her hand moved around her waist you knew what was coming next, having experienced this scenario countless times with your mom, your big sis, Dolores, Arianna and several other women throughout your life.
Rather than pulling her skirt's zipper down, Alisha simply pulled the waistband back, opening a tiny sliver of space that revealed just a slight hint of her massive, bulbous buttcheeks and the deep, dark crevice of her crack. She was wearing some fancy-looking lingerie but the back of it was largely swallowed greedily between those gargantuan meaty mounds, though mounds was probably the wrong word, for her behind was even bigger than your mom's or Lillian's, the biggest you could recall besides Dolores'.
The view was just as imposing as it was breath-taking and unfortunately for you, it took you a bit too long to fully process what was happening and by then it was too late, Alisha's fingers released their grip on you, sending you plummeting down into that growing abyss. The last thing you could see was an increasingly overwhelming amount of smooth, dark brown surfaces and then everything went pitch black.
Alisha shuddered for a moment. As usual with Lilliputians, your body temperature was quite a bit lower and retained heat much more poorly than her own kind, resulting in feeling as if she'd just dropped a diminutive ice cube down her ample posterior, rapidly engulfed by her bountiful, bouncing glutes. Wanting to savor more of that cold, she clenched her cheeks a bit tightly, enveloping with their gigantic mass more thoroughly than before.
To you, this feeling was familiar, similar to being trapped inside Dolores' or Arianna's tremendous behinds, although neither of them needed to do any clenching, their sheer size and weight was more than enough that gravity alone did the trick, smothering you in seemingly never-ending thiccness.
'I'll still have to ask him some questions to get some more info on his likes and dislikes but at the very least I can tell I'm going to have a fantastic son in law. And if I play my cards right, Fulki will be a very happy wife' She thought, finding it amusingly surprising that on her first day, without even meaning to, she had already found a great addition to be made for her family.
Her body rapidly warmed you up and the cold was utterly smothered out of you, getting infused with a relatively gentle warmth coming from absolutely every direction. But the pressure was much greater than when you were in her cleavage. You sighed, your pseudo-theory that Brob women were all quite touchy feely was proving true, much to your own disbelief. This was the sort of thing your mom would've done, so you weren't that surprised that yet another mom went and did it. All you could do was to hope she didn't keep you there for too long or worse, that she forgot about you back there...
What happens next?
