"Mr. Schue?" Finn wheeled himself out from under an old Cadillac as he heard his old show choir teacher call for him.
"Finn! I have an exciting proposition for you." Will rushed over to his and offered his former student a hand up. "I want you to help direct the new high school musical."
Will could tell he was in for a problem when he saw Finns face fall, refusing to maintain eye contact.
"Look Mr. Schue," he said with a sigh. "I just got back into town and I'm tired."
Will shook his head, as he placed and reassuring hand on the tall teens shoulder. "You're not tired, you're depressed. You need something to pull you out of your slump."
"I said no." And that was that. Finn turned back to the car he was working on, bending over to pick up his tools.
"There are other ways to convince you."
Finn rolled his eyes at Wills threat. "Mr. Schue, I've been wedgied daily for like the past two years. You honestly think that's going to convince me?"
"You're right. That's why I asked for some assistance." Burt stepped out from his office wiping the mustard from his sandwich onto his shirt.
"Now we both know you've been aimless since your discharge and we both agree helping New Directions would be in your best interest. But if you still wanna say no..." Burt grabbed ahold of a hook just above his head and pulled it down into view. Just at the sight of it Will blushed, remembering when Burt had hoisted him up by it.
Finn walked past the two, pushing the hook away. "Its still not going to work, hanging wedgies were Azimio and Karofsky's speciality. After a while I learned to zone out."
"Fine, then you leave us with no choice." Will shoved his smooth, clean hands down the front of Finns jumpsuit, easily grabbing hold of his underwear. And with the speed and precision of a man who has given his fair share of wedgies, quickly attached it the hook.
"Burt please!" Finn pleaded as the winch slowly lifted him up onto his tip toes. His briefs slowly slid higher and higher up on his stomach, squeezing his balls close together. He cried out as the pressure increased, "I thought you wanted grandchildren?"
Burt shrugged dismissively as he and Will enjoyed the show. "Eh, Kurt and Blaine can adopt."
Will lightly cupped his crotch, unable to not feel some sympathy pains for the poor kid. One last time he decided to give Finn a chance to free himself. "We'll stop if you promise to direct the musical."
"I already told you," Finns voice had gotten noticeably higher by now. "My time with glee is over."
The two grown men looked at each other and sighed. As Finn was lifted off his feet, his weight completely supported by the front of his briefs they turned and walked away.
"I'll hang up here all night, I won't do it!" He insisted.
Sad to see that he wasn't going to budge on the matter Will sighed sadly. "Fine, we'll let you down. But you'll need to help raise some money for the production."
Finn nodded in haste. True to their word Burt lowered the winch enough for Finn to stand on solid ground while Will detached the young mans monster melvin from the clamp.
"So how are we raising money?" He asked as he dropped his filthy jumpsuit to his knees. He was more than used to being exposed into front of the two men and felt perfectly comfortable fixing his briefs with them present.
"A car wash." Mr. Schue explained. "The rest of the kids will do the washing, all you have to do is hold the sign."
"That's it? Easy." Finn beamed as he fished his no longer tighty whities out of his smooth pale ass.
"In a special costume," Will added with a devilish smirk. "Or you can just give in and direct the musical."
-------------------
"This isn't a special costume." Finn said in frustration as he stood out in broad daylight in a baby blue jockstrap. "Where did you find this anyway."
"My own collection," Will admitted as he waved around a sign to advertise the car wash.
"What?!" As if being nearly naked in public was bad enough, now Finn how to be caught in another mans underwear. "Mr. Schue I can't-"
Will was quick to shut Finn up with one knowing look. "Please Finn. This wouldn't be the first time you wore my underwear."
"Will!" Finn quickly looked around to see if anyone heard, his face bright red.
Mr. Schue rolled his eyes, ignoring his old students complaining. It was true that Finn had, in the past begrudgingly worn his teachers briefs, though only because he had to. It would be days were Finns undies were torn off and he neglected to bring an extra pair. Most of the other boys didn't mind going commando but Finn absolutely detested it.
The only problem they had run into was a slight size problem. Will tended to wear medium, liking his underwear tight whereas Finn preferred the loose comfort of a large. This discrepancy usually went undetected save for the occasional squirming of Finn when dealing with a rather nasty natural wedgie.
Today however, the sizing issue was much more noticeable. As the tall teen shifted uncomfortably from side to side he tried to nonchalantly pull down the pouch of the jock to cover more but all did was expose the top of his curly brown pubic hair.
"How it hanging Finn?" Burt chuckled as he slapped his son in law on the back and peered down at his bulge. "To the left I see."
"Ha ha." Finn said as he adjusted himself. He turned bright red as he noticed a testicle slightly hanging out and quickly tucked it back in. "I've had two bored housewives come over to spank me and one dude even yanked these straps up my butt. Am I done yet?"
Mr. Hummel didn't enjoy watching the poor guy suffer but he had brought it upon himself. "Nope, the news crew isn't here yet."
"The what?!" He didn't even need to understand to react, snatching the sign from Will to cover himself.
"KBBL, they got word about the car wash and wanted to film a report on it. Oh, there they are now." Both older men waved down the large news van as it pulled into the parking lot.
Out popped Lisa Larkin, the prettiest news reported in Lima county. Finn had always had a crush on her, ever since her report when the local lake caught on fire. Finn dropped the sign and dashed for the auto shop, ignoring all of the cat calls as his bare butt bounced.
"No way, no how." Finn said, his eyes as wide as saucers as the new crew approached the building. "I am not going out there."
Both Will and Burt looked at each other, the same mischievous smirk appearing on their faces as the rushed forward at Finn, grabbing him by the arms and dragging him towards the door. Seeing they meant business the teen relented. "OK! OK! I'll do it, just please help make them go away!
Burt and Will looked at each other, their smug expressions plain to see. "Glad to see you finally came around," Will said with pride as he left to greet the reporter.
