Yes, but hesitantly

Matt hesitated...but tucked the book under his arm and looked over his shoulder. He started to unbutton his pants then hesitated..."Will you give them back?"

“Of course” Alan smiled. “I just need to see your little guy again, think of me as Gregg Davies” he smirked making a Taskmaster reference. “And you're my famous person humiliating yourself for my and everyone's amusement,” he teased.

Somehow the logic was enough for Matt. Maybe it made sense, but he knew he was thinking with his penis now. He felt the ache in his balls driving his decision making. He really needed to please Alan. So he nodded, triple checked that no one was around, and dropped his pants. Matt quickly stepped out of them, bent over and picked them up, and reluctantly handed them over to Alan. He now stood in the library in a shirt and his underwear

Alan smirked as he looked over the choice of underwear… a plain pair of white briefs that both did little to hide his small bulge and also showed it was small!

“Love the underwear” he teased as he reached forward. “Did you pick out your most embarrassing pair just for little old me or do you always wear such dorky pairs”

"These are my normal pair...I was always told I didn't need all that extra room from boxers..."

Alan laughed softly. “And whoever told you was right… now are you hard” he asked staring at the bulge.

Unable to admit it straight out, Matt simply whines quietly, "I can't help it, its reacting to all the adrenaline."

Alan put his hand on Matt’s shoulder. “Shh… it’s ok lil guy… embrace the fact you have a teenie tiny little boner… I’m not going to judge you for it… just humiliate you for it like you want me to” he added with a smirk. “Was it hard when I saw it before?” He asked with a sly grin.

Feeling the hand on his should sent a jolt through Matt's chest and down to his penis, which jumped a little. "Yes Alan...I was hard"

“And does it embarrass you if I tell you it’s the smallest teenie little weenie I’ve ever seen?” Alan smirked with a grin

Matt examined Alan's face. Was he just saying that? Or was it true? He wasn't sure if he knew which answers he wanted, but he replied "The smallest you've ever seen?" Matt practically whimpered and Alan would be able to see his rock hard tiny erection pointing right at him, and if he looked closely he would see a little precum already forming on the tip

He smirked.

“Well… almost” he laughed.

“Why don’t you pull out your tinky winky and show me how you jerk it… right here in the library, with your tightie whities at your ankles, like the teenie tiny perv you are…”