Harry Can't Win

[flyingmonk]

The following story and all characters therein are entirely fictional. No similarity to real life individuals or situations is intended.

Synopsis: A freshman boy flees from upper class boys to avoid a stripping. He enters a room where four Junior girls are working. He finds out that the girls are worse than the boys.


Harry fluffed up his pillow and turned out the light. Would he have the dream again? Initiations were going on at high school. Tales of juniors and seniors stripping freshmen had given the fifteen-year-old some recurring and very vivid nightmares. So far Harry had avoided the embarrassing ritual at school, but not in his dreams.

The Dream

Harry burst into the school room as if he was running from a fire. He peered out the window of the door looking frantically in each direction. A rustling sound from the side caught his attention.

Inside, four Junior girls, all aged 17, stopped working on some signs for the upcoming football game and looked at what the commotion was.

“Oh, sorry,” Harry muttered as he turned to see the four girls staring at him. “I’m hiding.”

Harry was tall for his age. He had a crop of blonde hair that he combed straight. It laid on his ears on the sides and rested just above his eyelids on the front. A set of braces were on his teeth, and he hoped they would be off soon. He didn’t play sports but had tight abs and stomach.

“Hiding from who?” Jenny, one of the four remarked.

“Some Junior guys are chasing me. They are going to strip me.”

“Strip you?” Jenny laughed. “Oh, you’re a freshman then. Yea. We do that to the freshmen girls too,” Jenny replied as the other three laughed.

“What? You strip the girls, like naked?” Harry asked as he continued to scan the hallway.

“Completely naked,” Jenny replied. Right girls?”

“Every stitch,” the other three replied in unison.

“Then we spank them or something. Rite of passage sort of thing. So, what makes you think you can hide here? If the guys don’t get you today, they will get you another day, and it might be worse. Just let them strip you and get it over with.”

“No!” Harry replied. “I don’t want to be stripped. They take your clothes and hide them, and you have to walk around the school naked trying to find your clothes. It’s humiliating.”

“Sounds like fun to me,” Jenny replied.

“Oh crap. Here they come. Where can I hide?” Harry replied nervously.

“Cowards hide,” Jenny replied curtly. “Are you a coward?”

“No, I just don’t want them to take my clothes off.”

“What’s your name?”

“Harry.”

Just then the door burst open again and four Junior guys came in.

“Look boys. He is hiding in here with the girls,” They teased.

“Sorry girls, but we’re going to strip him. You can’t save him from that.”

“Oh, we don’t care if you strip him but leave him in here with us after you do. We won’t tell anyone,” Jenny said sarcastically as their treachery was beginning to form.

“Fine by us.” Get him boys.

The four girls watched as they drug Harry to the floor and began pulling his clothes off. Harry wriggled and tried to free himself, but it was a losing battle. They were just too strong.

They boys were cheered on by the four girls who delighted in watching Harry’s ordeal.

They grinned when his shirt was taken off revealing the fair skin of his bare chest.

When the boys pulled off his pants they all leaned closer to note the bulge in Harry’s white undies. Their eyes raised in approval when the boys stripped off his underwear to reveal what was underneath.

In short order, Harry lay naked on the floor with his hand across his privates and his face beet red.

“He’s all yours girls, “One of the guys said as they left the room with Harrys’ clothes in their arms.

“See, I told you hiding in here would not help you. Now look at you. You’re naked in a room with four girls. I bet you think we're going to go easy on you and have some sympathy. Well, you’re wrong.”

Stand up!” Jenny snorted.

Harry sheepishly rose to his feet as the four girls walked over and stood directly in front of him.

“Well, Harry, I am Jenny. This is Amanda, Tina, and Kim. If you do exactly as we tell you to do, we may help you find your clothes when we’re done with you.” If you don’t, we will sick the boys on you again and it will be even worse,” Jenny relayed as she locked the door and pulled down the curtain.

“Thanks,” Harry replied in a soft voice as he studied their appearance. Jenny was a brunette of average height with doe-like eyes and soft complexion. She also had an assertive and dominant personality. Amanda was a dark-haired girl and slightly shorter than Jenny. Like Jenny, she had a light complexion with gorgeous eyes. Tina had long blonde hair that went down to her chest. She was average height and build. Kim was rather tall and thin but not skinny. She had wavy blonde hair that was shoulder length and was wearing a school shirt like that of a cheerleader.

“Put your hands on your head Harry. Let us get a better look at what you are trying to hide down there,” Amanda then ordered.

Harry took a deep breath and slowly removed his hands, placing them on his head. The four girls then began surveying his body. They rubbed his chest, rubbed his butt, legs, and arms probing to find the right sweet spots and watch his reaction.

“Gee Harry, for a freshman, you have a decent body. Nice penis even,” Kim chimed in.

“Yea, his balls are huge,” Tina added.

“So, Harry, back there when we were telling you that we stripped the girls too, you acted like that turned you on. Did it?” Jenny asked. “Does the thought of us stripping other girls naked get you hard?”

“A little,” Harry replied. He wasn't sure why, but their probing questions as he stood naked before them was strangely exciting.

“Well, we do Harry, “Jenny replied as she ran her hand down his abdomen towards his lower stomach.

“We corner them and make them take off everything. Skirt, dress, pants, shirts, bra, panties. Makes no difference. They are shy just like you and try to cover their tits and pussies, but we won’t let them. We’ve even made them play with themselves for us,” Jenny replied.

Harry’s penis twitched and began to harden at Jenny's words, making the girl’s all cackle with glee.

“Oh, I think he likes that idea,” Amanda teased as they watched his erection grow.

Jenny reached down and cupped his balls in her hands, making him even harder.

“Harry, shame on you,” Tina teased. “Standing naked in front us girls with a raging hard on. We should spank you.”

“That is a wonderful Idea, Jenny quipped.” Do you want us to spank you, Harry?”

“No,” Harry replied shyly, silently hoping they were just kidding.

“Too bad because that is exactly what we are going to do. Get over there and lean over that desk, put your hands on in, palms down,” Jenny ordered.

The four girls led the hapless boy over to the desk and guided him into position. Harry could not believe this was happening. He would have probably fared better with the guys he thought, but now it was too late.

“You have such a cute butt,” Kim remarked. “Tight, and athletic. Now spread your legs.”

With Harry leaning over, the four girls took their places behind him. Each one took turns slapping his bare bottom. They even made sure to run their hands between his legs and graze his balls to keep him hard.

It wasn’t long until Harry’s butt was glowing red, much to their amusement.

They then turned him back towards them, grinning at his raging erection.

“How many times do you jerk off in a week Harry?” Jenna quizzed.

Harry shrugged his shoulders. “I don’t know?”

“You don’t know how many times you stroke yourself?” Amanda interjected. “That’s pathetic Harry”

“Think Harry. Tell us how many?” Kim teased.

“Two,” Harry replied in a strained voice.

“You only jerk off two times a week? That makes our school look bad,” Jenny huffed. “You’re a slacker jacker, Harry. We want our males to be virile and masculine not weak and unable to get it up."

“Who do you think about when you’re doing it?’” Jenny probed sadistically.

“Yea, what girl do you imagine naked Harry?” Amanda chimed in.

Harry swallowed hard as he felt his arousal growing at their rapid-fire sexual questions. He thought about the freshman girl he often fantasized about.

“Ava,” Harry replied.

“There’s an Ava? I don’t know her. Too bad we don’t have Ava here. You could watch us strip her. I bet you would like that wouldn’t you Harry?” Kim replied, joining in to excite Harry all the more.

“Do you really want us to help you find your clothes?” Jenny questioned.

“Yes, please, Harry pleaded.

“Then picture it in your mind Harry. Stroke yourself while you’re imagining it,” Kim barked.

All four girls surround him as he began to slowly massage his rigid shaft.

“It’s the girl’s locker room. Ava walks in. She’s wearing a cute yellow dress with spaghetti straps over each shoulder. We all surround her blocking her from running. I pull the straps off her shoulder and lower the dress until her bra is showing. She’s wearing a bright yellow bra. it's practically see-thru. We can see her nipples,” Jenny teased as she rubbed Harry’s chest with her open hand.

Harry's penis was throbbing as he began to stroke faster.

“She’s scared. Nervous. She asks us to stop but we just laugh,” Amanda joins in to add to the vision and Harry’s torment.

“I look at Jenna. She nods for me to proceed, “Amanda continued as she leaned into his ear. “I reach behind and unsnap her pretty bra. She gasps begging me to stop as the bra falls off. Ava’s bare tits are now on display. Her chest is heaving. She’s breathing wildly as we all rub her tender breasts. The nipples harden, “Amanda whispered into his ear.

“While they are working on her tits, I pull her dress downward. She tries to fight, but it’s useless,” Kim joins in placing her hand on his butt and rubbing it as he strokes himself harder.

We take her shoes and sock off and force her to raise her feet as we remove the dress from her body. All that is left now is a pretty pair of yellow panties,” Harry,” Kim teases.

“Poor Ava begs us not to take her panties off,” Tina joins in as she rubs Harry’s thighs. "She is practically in tears.

“Kim and I reach into the top of her panties and begin to pull them downward. We are going to strip her naked and she can’t stop us. Her panties slip past her crotch and down her legs. We make her step out of them, then make her sit down and spread her legs wide. The pink, puffy lips glisten in the light of the room. Her clit sits begging to be toyed with,” Tina continued,

The narration and vivid descriptions had Harry in an erotic twilight zone.

“We stand her up, whirl her around and pin her to the wall,” Jenna remarks as she joins back in. “Her perfect little ass sticks out in all its naked glory. I slap her butt with my open hand. She winces. I spread her butt cheeks wide and bend her body. We all look at her puckered little hole,”

“I’m going to cum,” Harry groans.

Jenny slides a trash can in front of him.

“Cum in that!” Jenna scolds. “Don’t get it on the floor.”

Jets of semen splatter onto the black liner of the trash can as the girls laugh and high five each other over their erotic manipulation of Harry.

Amanda hands Harry some paper towels. “Wipe the head of your penis off.” She murmurs.

“Well Harry it’s been fun, “Jenna remarks “Let’s see if we can find your clothes. We have work to do. Big game Friday night.”

She texts one of the guys that had stripped Harry earlier and he informed her that they hid them in a trash can by the back door of the school. Harry ran down the back stairs to retrieve his clothes.

End of dream

“Harry Mitchell!” His mother’s voice woke him up. Drowsy, Harry batted his eyes until he saw his mother standing over him with her arms folded and head shaking as she looked down at the sight of the semen splattered on his chest.

“Get in the shower right now! Your breakfast is getting cold and you will be late for school. I just washed those sheets yesterday too young man.”

Harry dragged himself out of bed wondering if today they would be the day they get him at school.

The end

[TeenFan]

Fun dream.
The reality of his mother waking the poor guy up, his chest splattered with cum...that is a nightmare in itself.

I'd want to know where this school is, where both the Freshman boys and girls get stripped.
I'd be sure I am a grade or two above the Freshman, then I'd find a group of girls to hang out with...since they strip boys and
make girls masturbate. It would be cool to have a naked freshman boy watching a naked girl rub herself. The girls will place
a bet on whether or not the Freshman boy will do a hands free orgasm just watching that.

Feel free to use this idea for a follow up chapter.

[flyingmonk]

Fun dream.
The reality of his mother waking the poor guy up, his chest splattered with cum...that is a nightmare in itself.

I'd want to know where this school is, where both the Freshman boys and girls get stripped.
I'd be sure I am a grade or two above the Freshman, then I'd find a group of girls to hang out with...since they strip boys and
make girls masturbate. It would be cool to have a naked freshman boy watching a naked girl rub herself. The girls will place
a bet on whether or not the Freshman boy will do a hands free orgasm just watching that.

Feel free to use this idea for a follow up chapter.

I do like that idea. Most of my stories are silly one offs, but that would be a fun thing to write. It's possible Jenny was just blowing smoke in his ear about stripping the girls, but it also may be true. Thanks for the suggestions and kind words. I can imagine a few boys having a hands free orgasm while watching girls strip other girls.

[NickTwisp]

The story set-up also leaves open the possibility that the in-school public stripping is just a dream sequence. It will be interesting to see if the stripping really takes place in the actual school setting in front of numerous other students.

[flyingmonk]

Exactly!

[flyingmonk]

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Harry Can't Win Part 2

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flyingmonk
Harry Can't Win Part 2
Post Tue Oct 06, 2026 9:05 am

Like a man on death row awaiting his execution, every day brought a new anxiety about being stripped at school. Being naked in front of others is fine if you’re in public showers or changing rooms, but not in the hallway of a school with 200 of your peers looking at you, laughing, and capturing your embarrassment on the latest technology.

Friday dawned with an ominous foreboding; Dark clouds, drizzle, and a chill filled the air.

The first two periods went by as always. Harrys next class was on the second floor where the upper classmen were as well. He had an extended break before class so he dunked into the boy’s restroom to pee.

The only available urinal was in the center. Two junior students were on either side. Harry paused, but the need made him take his place and he began emptying his bladder.

“This guy’s a freshman. I don’t think we’ve got him yet,” the boy on Harry’s left side yelled to the boy on his right.

The alarm bells went off in Harrys head. This was it. The gods had abandoned him. Harry cut off his stream, stuffed his penis back into his undies, zipped up and headed for the door.

“Freshman! Get him!” the two shouted to others coming in the door. Like Daniel in the lion’s den, Harry was set upon with reckless abandon.

They dragged Harry kicking and writhing to the back of the room. While some watched for any approaching teachers, Harry was lain face up on a wooden bench. His arms pinned and his legs held, Harry watched helplessly as one by one every piece of clothing was removed from his body.

They stood him naked, Showing him off like a Roman soldier parading his naked captives down the village streets.

A sizeable crowd had formed now. The bathroom was filled with bawdy laughter all at Harry’s expense.

Escaping was futile. Harry was the object of amusement. His arms pinned behind him, he was helpless to their taunts as they pointed to Harrys flaccid member and his hairless balls.

It could have stopped there, after all, Harry was buck naked. They did the deed, but now the second part came. The humiliation. The denizens of disaster worked feverishly on their helpless victim.

As Harry was held in place someone grabbed a can of shave cream. Before Harry knew what was going on he felt the gooey substance against his skin. Then they started rubbing it on his balls. His penis hardened. Luckily for Harry, it wasn't the kind of gel that would irritate the skin. It did the opposite. It stimulated it.

Harrys subconscious began questioning his sexuality. His mind answered. Relax Harry your not gay, your penis is just responding to external stimuli.

Harry snapped back to reality. What was this? Toilet paper. Rolls of toilet paper. They worked to wrap Harrys body from his waist to his balls in sheets of toilet paper, like a half naked mummy until their work was done.

Then came the challenge. Harry would be taken into the hall.
Clad only in a half assed wardrobe of toilet paper. He must make a dash down the hall, retrieve his clothes and run back to dress.

A careful check was made to ensure no teachers were around. A sea of students lined the hallway on each side. The guys stood with Harrys clothes at the opposite end.

The signal was given. Harry bolted like a wild animal heading to devour it’s prey. Cheers, jeers, and guffaws erupted as Harry began his sprint.

The cool air slithering over the shave cream gave Harry another unwanted erection. His penis jutted out from the toilet paper. There he was running down the hall wrapped in toilet paper with his dick sticking out bouncing up and down like a springboard at the pool. A sight not lost on the girls.

Now, the action of Harry running was causing the toilet paper to unravel. Strand by strand was falling to the floor. Harry was naked again. Just as he reached his clothes his penis erupted with globs of semen. He was cumming in front of them all. His face went ashen with shame.

Cameras moved to catch the eruption. Harry grabbed his clothes and turned to run, only to slip on his own semen. Getting up he ran naked to the shelter of the boys room.

Back in the restroom, Harry quickly dressed. It was over. The hallway grew silent and everyone went about their business.

The janitor tried to figure out what the hell was on the floor.

Harry made it to his class and was the talk of the day. At least it was Friday. By Monday a new victim would be sought and Harry would no longer dread the day.

Maybe….