"Actually," Jessica mutters, "I do recall you having a thing for boobs. And even though I've never had the largest in the class, to you, these babies must seem enormous" Jessica states as she starts to unbutton her shirt. What she revealed was a black lacing bra holding two large C, not quite D cup, breasts. Jack was flustered. "Uh, I'm sorry Jessica, but I really think that it would be better if I went back to my house on my own. B-but I really a-appreciate your gesture". Just when Jack turned away to run, Jessica snatched him by the arm and brought him to her face. "It's really not a problem, my little Jack. I do insist you coming with me" she said with an evil smirk before releasing her clutch on him. Jack hit Jessica's right boob, then slid into the vast expanse of her cleavage. He quickly squirmed his way to the top, but his attempt was in vain as a giant finger loomed above. "Let's get you nice and secure, Jacky. Can't have you falling out, that might hurt you". With that last little remark, Jessica's finger plunged Jack into the abyss of her pale and fleshy rack. Jack was then silenced by the two enormous hills, and Jessica giggled as she buttoned her shirt back up.
As Jessica gleefully walked towards the west exit of the school, Jack kept trying to squirm one of his appendages free, but without any luck. Jessica had pushed him low enough in her bra that the pressure from her two breasts pinned every part of his body together. Without any light to foreclose any opportunities to seek, Jack was unable to do anything about the unfortunate situation he was in. He could feel the pace of Jessica's heart, which was beating quick with excitement, and was more than warm enough for his liking. As her heart rate slowed down, however, Jack became accustomed to the rhythm, and drowsiness overtook him as he faded into a light sleep.
Jack soon woke up. It was still dark and he could still feel the pressure of Jessica's breasts around him, but it was less than before. Something must have happened while he was asleep that slightly jostled him. Unfortunately, Jessica was still walking, so if Jack could manage to escape, he would have to take precautions to make sure he would be able to make it off Jessica alive. Jack was willing to take risks, though, and soon began squirming once again to get some sort of leverage in his fleshy prison. But before he could get any sort of progress, Jessica stopped walking.
Was she undoing her shirt to check in on her tiny passenger, or had she become distracted with something?