Thanks for the great comments and suggestions, I've tried to apply them to the third installment of the Problem Student story. Please enjoy!
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The teacher had asked James to take the bandage with him, and try doing the wrap himself before the next Phys-ed class, but to come see her before class so she could check it. James headed to the boys locker room a little early, and did his best to emulate the snug, and slightly complex pattern Mrs. Meyers had created with the bandage. After pulling on his gym clothes, he headed to the teacher's office, which adjoined the girls locker room, on the opposite side of the gymnasium.
James knocked on the heavy steel door and heard Mrs. Myers' voice call "come in" from the other side. He opened the door and went in, closing it behind him.
"Hi James" the teacher said brightly, looking up from some papers on her desk. She looked different to James. Her dark, shoulder-length hair was wrapped in a loose bun, showing the fair skin of her slender neck. The upper of her thick, smiling lips protruded beyond the lower in a little overbite James had not noticed until now. Her lips looked darker, and more striking than usual, because of the lipstick she wore. She normally wore a much lighter shade, if any.
"James?" Mrs. Myers probed, waving her hand at James. He blinked and shook his head slightly. He had never looked long at this beautiful teacher who had been so nice to him, and he was nearly swooning as he took in the details of her face. Her nose was rounded, but not broad, with faint freckles across the bridge, continuing over the tops of her rounded cheeks, lifted by her smile. The light creases at the corners of her eyes gave her face a motherly quality, without detracting from her beauty.
"Uh, hi Mrs. Meyers." he croaked, then swallowed "You just look so beautiful!". The honest words tumbled out of his mouth before he realized what he was saying.
"Oh, why thank you." The teacher turned her head slightly, looked back at him, and her cheeks colored. "That's nice to hear from a handsome young man."
James' face became several shades closer to red and he couldn't think of anything to say.
Mrs. Meyers stood up from her desk, walked over to James, saying "Let's see how you did with your homework." and flashed a warm smile. She immediately pulled down his shorts and began to examine his work with the bandage. He noticed her sweatshirt was partially unzipped, allowing glimpses of the inner curves of her breasts. She tugged gently at various parts of the wrapping, especially near the obvious bulge it was meant to contain. James could feel the pressure as he began to become aroused.
"Oops!" Mrs. Meyers exclaimed "Look what we have here." James' rapidly swelling penis had slipped out between two layers of bandage, and the teacher had gripped it between thumb and forefinger and was flopping it up and down. "You did a good job James, but the wraps didn't overlap quite enough. Let's get it fixed up." She said and began undoing the bandage, starting at his waist. By the time she got it undone, his semi-hard dick was standing out, arcing down slightly, swaying by her left ear.