He kept taking peeks at her, waiting for his chance. She entered an unskippable cutscene, and he decided to do it now, since it might not ruin anything.
He lifted the front of her skirt up, to which she immediately pushed it back down. "Jeff, not now!" He responded with "Why not?", getting "I'm streaming and on record pace, so it'd have to be seen everywhere..."
He took in what she said. "Wouldn't more people come in to watch it though if they saw your little diapers?" He moved her hand to the side, and lifted it back up, flashing her pink patterned diapers.
She was clearly blushing, but the cutscene ended so she couldn't do anything about it. "Just, please not now..." "Too late!" He decided to pull her skirt below her diaper, leaving it exposed until she fixes it. Just to be a bit more annoying, he lifted her diapered butt off the bed, and pulled it all the way off. "Jeff! Please stop.."
"Alright, I'll leave your skirt alone now." He did still go for her diaper, pulling the front out. Pulling it down a bit, almost flashing her genitals for the entire stream, he got an angle where he could crawl in. He could tell she tried to focus on her run, and he pushed on in.
He adjusted his position, and she shifted to try and stay comfortable, pressing her lower lips against him. Now, this was his confirmation that it worked, he knew he was free to do basically anything