The Men Of Boondock Stripped

The eight male faculty of Boondock Elementary School were worried. They had lost a very important bet to their women coworkers as to whose classes had read the most books over the summer. Whichever group lost the bet would get a spanking by the winners. In the case of the men, the agreement was ALL of the guys in the school would be paddled, not just the teachers. So, there they were, assembled in a line in the faculty lounge after school. Most of them figured the "spanking" would be a wimpy pat on their covered butts, yet admittedly had no idea of what was coming. That is, until Ida Finklewrinkle, the school prinicipal stood before them sternly.

"Welcome gentlemen, I'm glad to see you are all here. As you know, you lost the bet fair and square and Ms. Strongheel and myself will be administering your punishment in front of the entire women faculty. You are going to be spanked...completely nude!" "N-n-n-n-n-ude!" Mr. Target, the gym teacher stammered. "But you c-c-an't you just c-c-an't, that wasn't part of the agreement!"

"The agreement is whatever the women decide, since you all are the losers. Got a problem with that?"

"B-b-but-t-t-", Mr. Target sputtered. "Can't we at least keep on our shorts?"

There was some tittering and giggling among the women. Ms. Finklewrinkle and Strongheel had a quick conference with their coworkers. Smiling her best wicked grin, Finklewrinkle addressed the group.

"The women have decided you may keep on your undershorts."

There was an audible gasp of relief among the men.

"With one condition...you have to pull your little weenies out of the fly, for everyone to see."

The men groaned. That was just about as bad as being completely naked!

"Let's get going!" Finklewrinkle growled. "We don't have all day. All of you take your shoes off."

The men slowly removed their shoes, still not fully comprehending what was going to happen. Most of their faces were beet red and they were sweating profusely. However, the sixteen women in the audience were loving it! When all the men were shoeless, Finklewrinkle continued:

"Socks next!"

The men very awkwardly removed their dark dress socks and put them inside their discarded shoes.

"Now, everyone take off their shirt!"

The male faculty of Boondock Elementary continued to whine and complain, but eventually all of their shirts were at their feet. Most wore sleeveless undershirts, but a few crew neck t-shirts were represented as well.

"Undershirts, too!" Finklewrinkle was unrelenting.

Eight pairs of t-shirts were nervously peeled off as the men waited for their next command.

"Ok, I want each one of you in turn to take your pants off. Mr. Wingdale first."

Wingdale was a 3rd grade teacher. He was about 50 years old, and very boring. His hands were shaking so violently, he could barely get his belt undone. With infinite difficulty, he undid the clasp and slowly stepped out of his trousers. His undershorts were pretty unremarkable, standard full cut white boxers. That was pretty much what the women expected.

"OK, Mr. Hines you're next!"

Hines was the School Psychologist. At 45, he was very hairy and the women could hardly wait to see his legs. They were not disappointed. As Hines' pants fell to a heep at his feet, his plaid boxer shorts and curly black hair sprouting all over his legs were plainly visible to the crowd.

"Not bad," Mr. Johnson, it's your turn."

Johnson taught 5th grade and was in his 30's. He was very tall and thin, and quite good looking. The women eagerly anticipated viewing him in his underwear. Johnson did not disappoint. He wore blue trim boxers which complimented his youthful frame nicely.

"MMMM...quite good. OK, Mr. Target, let's see your legs."

Target swore under his breath. His hands were shaking as he lowered his sweats. Underneath were gray boxer briefs with an unmistakable bulge in them. Indeed, despite their humiliation, the other men were getting aroused as well. Their boxer shorts were slowly being converted into small tents, to the delight of the women.

"Now it's time for Mr. Clark to lower his pants!"

Clark was the youngest guy present at 24. He taught 2nd grade, and was very nerdy. With trembling hands, he lowered his pleated pants and stepped out of them. He was so aroused that part of the head of his boner poked out of the flap of his striped boxers. The women gasped.

"Now, Clark, we're not there yet. Put your weenie back in your shorts."

The women giggled as Clark nervously pushed his dick back in his boxer fly.

"Next!" Finklewrinkle glared at Mr. Bradley. He was also young at 26, and quite arrogant. The women could hardly wait to paddle his butt!!

"Jesus!" Bradley couldn't believe what was happening to him. He very reluctantly lowered his dress trousers, exposing teal silk boxers.

"I can see you all have been letting your wives buy your underwear!" Finklewrinkle managed a little smile.

The men made an effort to grin in their embarrassed state. They had to admit, it was true!

"Only two more. Mr. Owens, you're next!"

Owen taught Kindergarten and was the nicest of the group. Once his pants were down, the women could see his underwear was as inviting as the rest of him, tight white CK boxers.

"OK, last, but not least, pants off Mr. Downey."

Downey was the school janitor. He was 42 and very overweight. With considerable shame and crimson red cheeks, he slowly lowered his tight jeans. The women screeched with laughter. Downey was wearing tighty-whities and looked ridiculous!

"Tighty-whities are out Mr. Downey, especially on you....they look like a shrunken band-aid!"

The women roared as Downey's face turned even redder. He wore boxers to bed at night, but always chose white jockey briefs under his tight jeans. Despite his shame, he started to get a boner and his briefs bulged a little in the front.

"Now, I want each one of you to reach into your shorts and pull out your weenies. Let's see what you've got!"

"Please Ms. Finklewrinkle, don't do this!" Mr. Target got on his knees. "We'll do whatever you say for a year!"

"For two years!" Wingdale quickly added.

"You'll do whatever I say anyway! Now haul em' out!"

Slowly, but surely, eight very erect penises were removed from eight pairs of undershorts. There was a collective gasp from the women faculty, who all planned to have their husbands expose themselves in a similar manner when they got home. Mr. Bradley sported the longest erection, at well over seven inches, while Downey was the smallest at barely five. He hung his head in complete humiliation. The women then positioned themselves so that half of them were behind the men, while the remainder got a nice front view. Both positions were going to be very rewarding to view the spanking!

"OK men, bend over and Mrs. Strongheel and myself will administer your punishment."

The men groaned yet ultimately did what they were told.

"Here we go!" Finklewrinkle smiled triumphantly.

The men squealed with a mixture of embarrassment and pain as the administrators went down the line, giving then ten spankings each with their paddles. The thin material of their undershorts offered little protection, and they were all very worried about how they were going to explain the red welts on their asses to their wives. After what seemed like an eternity, Finklewrinkle and Strongheel were finished. All of the women were completely enthralled, as they had never seen men get spanked with their boners hanging out of their shorts before. Little did their husbands know what "surprises" their wives had in store for them that evening!

"Alright gentlemen, you have been thoroughly demoralized and the women are pleased. Now put your clothes back on and get the hell out of here!!"

The men threw their garments on, amidst a chorus of giggles from the women. Never in their lives had they been so completely embarrassed! Suffice it to say, things at Boondock Elementary School would never quite be the same again!

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It didn't take long for the women faculty of Boondock High School to learn the unhappy fate of the eight male faculty of Boondock Elementary....forced to strip to their undershorts, take their cocks out of their flies, and bend over for a thorough paddling. It was the general consensus of the Boondock High female teachers that men were far sexier in their underwear than completely naked. That made them determined to get the twelve male members of the Boondock High faculty down to their underpants, one way or another. But, before that eagerly anticipated event took place, a fortuitous opportunity presented itself. Four members of the Long Dong Club, one of Boondock High's worse gangs, were caught harrassing four officers from the Boondock High Gay Alliance. It was left up to the six female members of the faculty to determine their punishment. After school, the four boys from the Long Dong Club, along with the group of boys they had teased, were led into the school auditorium. "Alright boys", Ms. Grannypepper, the school principal boomed. "You know why you are here. Bullying is absolutely not allowed at Boondock High and it is time for your punishment." She took a deep breath. "You are going to be stripped to your underwear by the four boys you bullied and then paddled ten times by each of them. Oh, and there's one more thing...you have to take your dicks out of your underwear for everyone to see."

The four bullies groaned and swore up a storm. Two of them tried to escape, but were quickly blocked by the six women. Although they were all strapping 18 and 19 year olds, the women clearly had the upper hand.

"Anyone that tries to escape again will not graduate...I will see to that!" Grannypepper was adamant.

The boys whined, but each one knew he had to graduate with the rest of the class, having a repeated at least one grade. Very reluctantly, the two unsuccessful escape artists took their place on the stage with their Long Dong gang mates.

"Alright, it is time to begin!" Grannypepper continued. "I want Andy, Joe, Chip, and David to undress Pedro, Carlos, Mike, and Robert."

The four gang members tried to look cool and macho, but were very nervous. Very few people had ever seen them in their underwear, much less with their dicks sticking out!"

"Come on Ms. Grannypepper," Carlos pleaded. "We'll never do it again, we promise!"

"We said we were sorry," Robert added.

"Sorry isn't enough!" Grannypepper retorted. "Now, remove their sneakers!"

The four eighteen year old Gay Alliance members got on their knees and took off the Long Dong mens' sneakers, putting them in a neat pile.

"Now, take off their socks."

Four sets of white socks were hastily removed and added to the pile.

"Shirts next."

The Gay Allliance members got up and unbuttoned the gang members' shirts. Underneath, they all sported white wife-beaters which emphasized the dark hair on their chests. "Now, the t-shirts"

The Long Dong men had their wife beaters pulled off by their victims and added to the growing pile of clothing. They were really gasping and sweating now, knowing full well what was going to happen next!

"Ok, now the fun part. I want each Long Dong boy's pants taken off one at a time. Andy, you start!"

Andy slowly but surely undid Pedro's belt and lowered his zipper. His baggy jeans quickly fell to the ground, exposing blue and white striped full cut boxer shorts. Pedro grunted loudly. Despite his acute embarrassment, the slow stripping was turning him on. His eight inch penis surged to life, pressing the right leg of his boxer shorts out awkwardly.

"Good, very good!" Grannypepper beamed. "Now Joe, take Carlos' pants down."

Joe's hands were shaking in anticipation of seeing the handsome Carlos in his underwear. He quickly opened his baggy chinos and watched in awe as they fell below his knees. Carlos was wearing baby blue boxer shorts, and his cock was so full the thin material of the underpants barely held it in.

"Excellent...now Chip, take care of Mike."

Mike was the timidest of the gang and was really having a hard time being stripped. He practically hyperventilated as Chip undid his belt and lowered his zipper. A pair of green plaid boxer shorts were gradually revealed as Chip pulled down Mike's trousers agonizingly slowly. The six women gasped at the sight of the left boxer leg being pushed out to oblivion by Mike's monster wang. The thing must have been a good nine inches!!

"And last, but not least," Grannypepper beamed. "David, please take care of Robert."

Robert let out every cuss word in the book as his pants were undone and lowered to his ankles. His cock gave a mighty jump, but was held in place by the material of his white full cut boxers, at least for the moment! So, there they were, the four feared members of the Long Dong Club, clad only in their underwear. The women faculty were not surprised by the boxer shorts...that pretty much was the underwear of choice by the "Gangsta" type boys in the school. But before the paddling commenced, they wanted to find out how the handsome Gay Alliance boys looked in their undershorts as well.

"OK, good job Gay Alliance boys. But, I can see by the front of your pants that stripping the bullies was very arousing for you. I'm afraid you are going to have to strip to your undershorts as well!"

The Gay Alliance boys were shocked and scared. They had stripped to their underwear in gym of course, but this was completely different!

"Please Ms. Grannypepper," Joe pleaded. "We didn't do anything!"

"It will be much more comfortable for all of you to administer the paddling in your underwear. Now strip!"

The four boys grunted and groaned, but slowly started disrobing as the bullies guffawed and smirked. In a manner of minutes there was a large pile of garments on the floor and they stood beet red in nothing but their underpants. The six women faculty tittered and giggled. Joe and Andy wore white boxerbriefs that fit them like a second skin. Their fat peckers were so hard they pressed out a quarter sized piece of cloth. Chip wore blue boxer shorts that were similar to Carlos'. Only Chip was very tall and had long legs so they were sexier on him. However, it was David that took the honors in the underwear department. He was sporting a pair of blue plaid trim boxers that had cute little slits on the sides and were mouth watering on him.

"David, what brand of underwear are those?" Grannypepper had to know.

"Uhh, I don't know...my mom bought them for me."

Joe walked over and quickly turned down the back waistband of David's boxers until the tag was revealed.

"Jockey Life, Size 32!" Joe cracked up as he said it.

The bullies roared with laughter as Ms. Grannypepper started to frig herself.

"Make a note of that, girls, Jockey Life." Grannypepper was radiant.

The women faculty visualized a mental picture of how their husbands would look in the Jockey Life trim boxers. Their panties were soaked and their eyes were tightly shut as they fantasized about their next lovemaking session.

Grannypepper jolted them out of their pleasant reverie. "OK, now that everyone is comfortable, it is time for the unveiling." She turned to the four bullies. "Whip em' out guys, let's see what you've got!"

The four boys'hands were shaking so hard they could barely get them inside the flies of their boxers. With obvious difficulty, they manipulated their massive members and huge balls out of the small openings.

The women practically fainted. Each dick was at least eight inches, with Mike's closer to nine. The Long Dong Club, indeed! Grannypepper regained her composure after almost creaming her white panties. "Now, bend over, facing us, and the paddling will begin!"

Six pairs of eyes gaped as the Gay Alliance boys began paddling their enemies with glee. The Long Dong men grunted and screamed, swearing up a storm. Their audience put their fingers in their panties as the boys' big cocks bounced up and down like billy clubs. Never in their lives had they witnessed anything this hot! After a few minutes in which three women had loud orgasms, the paddling was over. The Long Dong members continued to slouch over in complete humiliation, afraid to even look at the women.

"Alright boys," Grannypepper bellowed. "I think you have been embarrassed enough for one day and will never bother the Gay Alliance again. Now get dressed and get out of here!!"

The Long Dong boys were in such a hurry to leave, they just picked up their clothes and ran out, putting them on in the hallway. The Gay Alliance boys got dressed quickly, thanked the women, and walked out of the room with contented grins on their faces.

Grannypepper turned to her colleagues triumphantly. "That was just a prelude to the main event...tomorrow the entire male faculty of Boondock High will be stripped to their undershorts!"

The women gasped with anticipation. Would tomorrow ever come?

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Note: This story originally appeared on the Stripping and Humiliation Sexboard, but has long since been deleted. If you want subsequent Boondock stories to be posted, put up a public message or email me privately. I am happy to submit more chapters if there is sufficient interest. Best, Sack