The Humiliation of Jimmy

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Oopsydaisy
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The Humiliation of Jimmy

Post by Oopsydaisy »

The Slumber Party

My older sister Emily and I didn't exactly get along.
On this particular evening, she had two of her friends spending the night and I had my best friend who lived across the street over as well. My parents had gone to a party and weren't expected home for awhile.

My friend Jon and I were admittedly being jerks. In retrospect, I'm sure that it was pent up sexual frustration although we wouldn't have had a clue!
My sisters two friends were what we would now days call "mean girls," but back in the late 70's, we just thought of them as, well, mean girls. Jan and Erin came by it honestly, they were both pretty, from wealthy families, popular in school and used to getting their way. Jan had red hair and big boobs (70's lingo). Erin was blonde, not as well endowed, but she had a great figure.
We were doing what any hilarious immature 15 year olds would do. We repeated everything they said, put tennis balls under our shirts and said clever things like "look at me, I'm Erin" or putting a basketball under my shirt and saying "look at me I'm Jan."
My sister was beside herself with frustration as we were ruining her little slumber party.
She pleaded with us to stop, but we were relentless.

At one point my mother called to say that they were going to be out later than they originally thought, so she wanted to check in and make sure we were okay.
My sister proceeded to tell her that things were not okay and told her everything Jon and I were doing. She told Emily to have me to pick up the other phone. I knew I was in trouble and slowly walked to the kitchen to pick up the extension. The last thing I saw was Jan and Erin huddling up next to my sister so that they could hear what was coming.
And come it did. My mother was PISSED. I had gotten a few C's on my still very recent report card and that coupled with my current behavior had set her off.
She used the word "mister" a lot and the phrase "straighten up and fly right."
She then told me that Jon had to go home right now and that I better behave perfectly for my sister and her friends or there would be no going to the pool tomorrow or anytime in the foreseeable future.
This got my attention. Going to the pool was the high point of my social life. We lived in central Florida, so we had plenty of heat, but no beaches nearby. What we had, was a big public pool, where every kid hung out. Most adults avoided it, which gave it sort of a Lord of The Flies vibe.
Not going to the pool was unacceptable, especially since Amy would be there. She was a girl in my class that I had a major crush on. I could tell Jon liked her too, so there was no way I could have him go to the pool if I wasn't going to be there!
So I sent Jon home and skulked back to my room, planning to pout for the rest of the night.
I flipped through some comic books feeling pretty sorry for myself.
My sister and her friends were in the den watching the only TV and I didn't want anything to do with them.

After awhile, my sister called out in a sweet, sing songy voice, "hey Jimmy, we're thirsty, will you bring us some cokes?"
No doubt you've figured out where this was going, but I hadn't. So I shot back in a sing songy voice of my own, "get 'em yourselves."
A minute later my sister appeared at my door. Doing her best mom impression, she said, "you'll get us those cokes mister or there will be no pool for you tomorrow!"
An entire war was waged and lost or won, depending on your vantage point, as we exchanged looks. I realized that whether she meant to or not, Mom had totally set me up. My look of horror created a look of pure joy on my sisters face. She literally skipped out of my room all the way to the den. I could make out excited whispering then loud laughter and then more whispering.
I trudged to the kitchen and my sister called out, "in glasses, with ice."
I got down three glasses and pulled a couple of ice trays out of the freezer. I struggled to free the ice from the metal trays, and Jan yelled out "hurry up already."
Once I poured the cokes and refilled the ice trays, I carefully walked to the den with three full glasses. I was about to set them on the coffee table, but my sister stopped me and told me to hand them out individually. This was tricky since I was holding three drinks with two hands. Jan took the first drink and I almost dropped the other two, but caught myself.
"That was close," Erin said as I handed her her drink. "If you'd spilled it, I guess you would have had to mop up the mess with your tee-shirt."
"Well," I said, "luckily I didn't." I then handed the last drink to my sister, who yanked it from my hand, causing some coke to spill on the floor.
"Oops" she said. "Would you be a dear and clean that up...with your shirt?"
"C'mon," I said, "that's not funny."
"We'll be the judge of that," Erin and Jan said at the same time, cracking the three of them up.
Then my sister stopped laughing and simply said, "now!"
I gave her a pleading look and then pulled my shirt off and proceeded to mop up the mess. As I did so, I heard more coke hit the floor behind me. Jan said, "oh dear, I seem to have spilled some as well." I crawled over to where she was sitting and mopped up her spill, only to hear more coke hit the floor. Erin didn't say a word, she just smiled at me. I started to get up to go mop up her spill, but my sister said, "no, I like that crawling bit, keep doing that." So I did.
"Now," she said, "go put that disgusting shirt in your dirty laundry hamper and then come right back."
"Can I get another shirt?" I asked.
"NO!" This time all three of them said it at the same time.
When I came back, I was informed that there had been another spill.
This time it was my turn to say "no!"
I'l spare you the back and forth, suffice to say a picture of no swimming all summer was presented to me in such a way that I knew my shorts were coming off.
I was literally shaking and doing my utmost to keep from crying.
The three of them just smiled as I slowly peeled off my shorts, revealing my tighty whities. Defeated, I moped up the spill and took my shorts to the hamper as well.
When I returned, I was relieved to see no more spills and even better, it looked like the girls had drained their drinks. Just three glasses with ice sat on the coffee table.
"You know," Jan said, "I'm still thirsty."
"Me too," said Erin.
"Why don't you go get another can and refill us," my sister said.
At this, I'm sure I looked panic stricken, because my sister said, "don't worry, no more spills, I promise."
Relieved that I could keep my underwear on, I went to the kitchen to get another can of coke. While I was in there, I heard my sister run into her room and then quickly come back, causing Jan and Erin to laugh. When I came back out, she was nowhere to be seen. Then, she came out of our parents room with something hidden under her shirt. She hid whatever it was behind a sofa cushion.
The girls had all grabbed their drinks and were standing a few feet apart. I approached Jan and was about to pour her some more coke, when she stopped me.
"You know what, I don't think I want ice this time."
"Okay," I said, I'll go dump it in the sink."
"Oh I hate for you to have to go all that way. What might be a better solution? Oh I know," and with that she pulled the elastic waist band of my underwear towards her, looked in and snorted a little and then dumped her ice in.

It took my breath away. It was so cold that I barely had time to register the humiliation.
"So," she said, "are you going to pour me some coke or what?"
Next came Erin. She did the same thing, only her ice was more water than ice. It pooled at the bottom of my underwear and seeped down my leg. I poured Erin some coke as I started to shiver.
When I got to my sister, she told me to turn around and proceeded to pour her icy mix down my butt.
The three of them laughed as I stood there shivering.
"Okay," my sister said. "Just one more thing and you can go to bed. If you can stand there with your eyes closed and a big goofy grin on your face for 20 seconds, we'll let you go."
I was elated. This had been humiliating as all get out, but I was just 20 seconds away from being done! I gladly closed my eyes and the girls started the countdown.
20, 19, ...3, 2, and with that I felt my underwear being pulled down to my ankles and then I heard a clicking whirring sound. My sister had pantsed me and Jan and Erin were pointing Polaroid cameras at me and had each snapped a picture. One caught me still smiling, the other with a hilarious (to others) expression on my face of confusion and panic.
While I was getting that coke earlier, my sister had gone to her room and grabbed her camera. Worried that I might lunge out and grab the picture, she had gone to my parents room and grabbed theirs as well. She was right to worry. I did lunge for Jan and her camera, but I slipped on the wet floor and fell flat on my face. This gave Erin an excellent opportunity to get a lovely butt shot. And they just kept coming. Sure polaroids are slow, but they still managed to get five or six more pics.
After that they did indeed send me to my room. They told me to sleep in the nude and that they would be in later to check on me. "And don't jack off in there, you pervert," one of them called out.
Later, I heard my parents car pull up. I crept to the end of the hall to listen to my sisters report. She told mom that I had been a perfect gentleman and that I should definitely be allowed to go swimming tomorrow. "Yes," Jan said, he was picture perfect."
It suddenly dawned on me that I was naked in the hallway, so I hurried back to my bed, missing the next part of the conversation...
"Oh I'm so glad he was good. I would have hated to keep him home. I know he is so eager to see that Amy girl."
"Wait, who's Amy?” my sister asked.
"Oh just some girl he has a crush on. He doesn't think I know, but we mother's know more than you kids think.”
"Amy Stewart," Erin said. "I know her. She's best friends Anna."
With that the girls all looked at each other and smiled.
An hour later the girls crept into my room. "Hey perv, you awake?"
Of course I was awake. Trauma has a way of doing that to you.
"Nudie check," said Jan, lifting up my sheet and shining a flashlight on my privates. I quickly cupped them, and Erin whispered in my ear, "pretty sure you could do that with just one hand pal."
"We thought you might enjoy seeing the pictures. Now here is the deal, we hand them to you one at a time. If you try to keep one or tear it up, we show the rest to all your buddies at the pool tomorrow. That's right, we've decided to join you tomorrow."
So I looked at the pictures and my heart sank. Not even one of them was out of focus.
Four front shots and three butt shots, each one more humiliating than the last.
Finally, I said, "you know, I've decided not to go to the pool tomorrow."
If they were going, the risk of humiliation was just too great.
"Oh you're going," my sister said. "You're going and you're going to do everything we say or else," and with that, she waved the pictures in my face.
So I was going. Maybe it wouldn't be too bad. After all, if they were blackmailing me with naked pictures, they couldn't exactly make me get naked. That thought gave me some comfort. That and the fact that they didn't know about Amy...
NudeBaG
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Re: The Humiliation of Jimmy

Post by NudeBaG »

Great start!
TeenFan
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Re: The Humiliation of Jimmy

Post by TeenFan »

Jimmy had his underwear packed with ice for a minute or two and after the stripping the girls didn't tease him about "shrinkage"?
Jimmy must be big down under. Please confirm if this is so.

Nice start to this story.
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Re: The Humiliation of Jimmy

Post by Lola »

It's great the way they stripped him! Funny when they said "No" all at the same time ahahah
Oopsydaisy
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Re: The Humiliation of Jimmy

Post by Oopsydaisy »

An Embarrassing Morning

I must have finally fallen asleep, because the next thing I knew my mother was shaking me awake.
"Wake up sleepy head, everybody else is already up. Your dad is out playing golf and Maria needs to clean your room."
I realized a second too late that mom was going to fling my sheet back, exposing me to both her and Maria.
"Where are your PJ's?" she gasped. I looked over at Maria who was covering her mouth with her hand and trying unsuccessfully to stifle a laugh.
"Muy pequeño."
"Si, si," my mother said, not really understanding Spanish.
"Mom," I yelled, trying to grab the sheet back.
"Oh no," she says, "if you can't be bothered to put on pajamas then live with the consequences. You know Jan and Erin are still here. I've half a mind to send you out there just like this. How would you like that? Think about that! Think about how humiliated you would be if they saw you like this. Just put on your bathrobe and come out so Maria can get started in here."

I didn't have to think about it. I was still standing there naked in front of Maria since my mother was blocking my path to the closet and Maria was not the least bit shy about looking me over and enjoying my predicament. Finally, mom moved enough for me to snatch up my bathrobe.
I followed my mother out to the kitchen and she told everyone what had just transpired, clueless to the fact that they were the reason that I was discovered in that state. Jan and Erin pretended to be scandalized.
She then grabbed her purse and a piece of toast off the table.
"Anybody need anything from the grocery?"
"Wait," I said, "where are you going!?"
She stared at me for a beat and then said, "the gro-cer-y."
"Right," I said a little panicky "but what's the hurry?"
"Aw, does little Jimmy miss his mommy?" My sister said.
My mom kissed me on the forehead. "I gotta go kiddo. Don't worry." She said, looking from Jan to Erin, "they won't bite."

And just like that she was gone.
A minute later Maria passed through on her way to the laundry room with a basket of my dirty clothes. I shuddered at the reminder of my clothes from last night.
Maria came back holding those very clothes and asked, "que paso?"
Well this cracked everyone up.
Maria was 17. Her mother had worked for us for a year or so and Maria had recently started helping out on weekends. She and my sister were pretty close. She helps my sister with her Spanish and my sister helps her with her English. They treat each other like friends. I treat her like the maid.
Emily started talking to her in Spanish, which I don't really speak, but by the way Maria was looking at me, I had the feeling she was telling her everything.

Maria went back to start the laundry, but then came back with a grin on her face.
She pointed at me and said, "sucio."
At first my sister looked confused and then started to laugh.
"She says your bathrobe is dirty, it needs to be washed."
"It's perfectly clean," I said.
Next thing I know, my sister grabs my bowl of cereal and dumps it in my lap.
I jump up and screamed, "what the hell!?"
"Oh yeah," Jan says, "that's dirty alright. Erin, let's help him out of this."
And before I know it, they have pulled off my robe and given it to Maria.
"Look at the mess you've made," my sister says. "You need to apologize to Maria."
"For what," I say, "for being naked!?"
"Among other things," my sister says. "Mostly for just being a jerk."
So I am standing there naked, covering my privates yet again. I tell Maria that I am very sorry.
Maria smiles at me and then turns to my sister and asks, "Como se dice 'pequeño' en ingles?"
My sister translates for the rest of us, although she needn't have bothered since Maria used the universal thumb and forefinger sign for small penis.
"Little," my sister says.
"Tiny," says Erin.
"Microscopic" adds Jan.
Everyone, but me, has a good laugh, when the word Maria latches onto is 'micro-escopic.'
I ask if I can go to my room when Maria starts talking to my sister again, repeating the word azotaina.
My sister laughs and invites Maria to sit in her chair. Maria does so.
"You know, Maria is always saying you need a good azotaina. Well, no time like the present. With that she guides me over to Maria who takes hold of my arm and yanks me down so that I sprawl over her lap and she begins to spank my behind with gusto.
Meanwhile, Jan races out of the room and comes back with a hairbrush that she hands to Maria.
"Muchas Gracias!"
Now it's Erin's turn to run out. She is back in a flash, and over the sound of WHACK WHACK WHACK, I hear "click whirr..."
After my spanking, I am made to mop the floor in the nude. Emily tells me that from now on, when mom isn't home I'll do the housework that Maria usually does. I am then told to go get ready for the pool.
"Oh and we laid out your suit for you," my sister called out after me. Not surprisingly, it was the skimpiest of my suits. Not a speedo, but a cousin to be sure.
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Re: The Humiliation of Jimmy

Post by TeenFan »

"Muy Grande" would be just as funny, when Jimmy is compared to a beast of burden, a donkey...a burro with a boner, but that is just my humble opinion...lol
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Re: The Humiliation of Jimmy

Post by Oopsydaisy »

IT BEGINS

After I'm dressed we head to the pool. Jon sees us leaving the house and meets us in the street. It is only 4 blocks to the pool, a walk I usually enjoy.
Jon gives me a questioning look as he stares at my suit and I just shrug. Then he starts to make a crack about Jan's sexy bathing suit and I tell him to shut up.
He looks wounded and doesn't say anything else. I feel bad, but there aren't naked pictures of him in anyone's pool bag!

When we get to the pool, I look around for Amy and I am both relieved and disappointed not to see her. The girls share a sly smile and Emily asks me what I am looking for.
Speaking of the girls, I was to find out later that they had stayed up half the night working out different strategies on the best way to humiliate me at the pool. Most of them were ridiculous and relied on coincidence, amazing timing or others being able to intuit exactly what was going on. As it turned out, some of their plans worked out just fine!
It had dawned on them also, that they couldn't force me to strip naked at the pool by threatening to show everybody naked pictures of me. No, they planned to get me naked, but they wanted to make it count.
So I was feeling cautiously optimistic that maybe I'd just have to get my sister and her friends drinks and food when they wanted and other pesky little things like that.
Those hopes were quickly dashed.
We all go through the entrance turnstile, my sister, then me, and then the others following behind. Only we don't quite go though. As soon as she gets through, my sister turns and holds the bars so they don't turn.

I better take a second and explain. This particular kind of turnstile is all bars running parallel to each other from floor to ceiling. You could climb them like a ladder until you hit the mesh at the top. The whole pool area is enclosed by a chain link fence. Not exactly high security, but enough to make sure a kid pays his dollar to get in.
Also, due to possible injuries, it was very much frowned on to do what my sister was doing. Sure enough, a pool employee, all in their teens to early 20's, comes running over and tells my sister to "stop it."
"Oh it wasn't me," she says pointing my way, "it was him." Now anyone with eyes could see that this was not true. Not only not true, but not possible. This guy did have eyes and those eyes saw my sister. Those eyes saw that she was way out of his league and those eyes saw that she was smiling at him. So he turned those eyes on me and said, "I'm warning you kid, pull another stunt like that and you're outta here!"
A few other pool employees looked over at me and shook their heads.
I was about to object, but didn't see the point. I did, however, see my sister stroking the arm of the guy who had just yelled at me and whispering into his ear. He looked over at me and grinned.

Plans, plans.

Jon asks me to head over to the diving pool, because that's what we usually do. We like to sit and watch the older, bikini clad girls dive. Our favorite part was when they get out and run their thumbs along the back side of their suits and yank them up. Every time we’d get a glimpse of a butt crack, we hoot and high five each other. It annoys the girls, but what do we care? Sometimes, if the life guard happens to be a woman, she will blow her whistle and tell us to move along.
I tell him to go without me, that I'll be there soon enough (I hope). He calls out to another friend he sees and is gone.
"Don't worry," my sister says, "we'll get to the diving pool soon enough."
Just then another friend of Emily's walks up to us.
"Hey Mindy," Jan says, "want to see some naked pictures of Emily's little brother?"
I literally jump back and scream "NO."
Mindy cracks up and says, "what!?" "Um, yeah!"
And just like that, Jan whips out the pictures and hands them to Mindy who looks at each picture wide eyed and laughing. She is about to wave them in the air and call over to a group of friends, when Jan pulls her arm down and takes the pictures from her.
"For now," she says, "you can't tell anyone. We were just impressing on little Jimmy here that we mean business!"
With that, Erin, who had walked away a few minutes earlier, came back over to us and gave Emily and Jan the OK sign.

"Alright," my sister said, "you're first assignment is right up your alley. We want you to 'accidentally' walk into the girls changing room, count to ten and walk out."
"But someone might be in there," I stammered.
"Of course, someone will be in there, dumb ass, that's the whole point!"
I didn't really understand how this was a punishment, but I was really nervous as I walked towards the changing room. Jon and I had snuck into Carrie at the theater last month, and were thrown out pretty quickly, but not before we'd seen the slow motion shower scene. I kinda had that in my head as I rounded the little hall and walked in.
No such luck. There were six or seven girls in there, some in street clothes, some in bathing suits, but none in any state of undress.
As it turns out, Erin had warned them. She told them that she overheard me bragging to some guys that I was going to walk in there and then play it off as some kind of accident.
So they were ready for me, but they were still pissed!
As soon as I said, "sorry, sorry," and started to back out, they started yelling at me. I ran back to the pool area, but at least one of them followed me out and yelled to anyone in earshot what I had just done. I got some dirty looks as I walked back over to the girls.
They wagged their fingers at me and told me to grow up. Then, when the attention died away, they laughed and told me I had done a great job.
I was hoping that was that. Not great, a bunch of people around the entrance thought I was a perv and hated my guts, but if that was it, I could manage.
Of course, I didn't know that while I was "on assignment," Emily, Jan, Erin and now Mindy were letting other people in on their plans and teasing them with a brief glimpse of a picture or two.

Next up, they told me about my next job. Again, not what I expected. They had me call Jon over. He came trotting over and the four girls started peppering him with questions.
I think he quite liked the attention, so it was easy to slip around behind him and pull his suit down to his ankles. The girls all roared with laughter and pointed as Jon struggled to pull his suit back up. I took off running as I was instructed to do. A couple of guys yelled after me, "not cool man" and the life guard blew her whistle at me and gave me a dirty look.
Jon, of course, was all set to chase me down, but the girls stopped him and calmed him down a bit.
When he eventually came over to me, I begged his forgiveness, explaining that they had made me do it. He told me that they had just got through telling him the same thing. He was embarrassed, but all was forgiven.
"Let's go watch the girls dive," he said, and off we went.

We had only watched two or three girls yank up their suits when the Gang of Four appeared.
Emily came up to me and said, "I was just telling the girls what a great diver you are. Will you show them what I mean, please?"
I smiled a little. I was pretty good, so I said "sure."
"Oh and one more thing," she said and whispered into my ear.
So I did just as she asked. I dove off the board into the water and went as deep as I could. On my way back up, per my sisters instructions, I loosened my draw string and yanked the backside of my suit down so that most of my butt was exposed. I then climbed up the ladder and didn't pull my suit back up until I was all the way out of the pool.
Jan and Erin hooted and high fived, but it didn't seem like that many people noticed.
Mindy came over to me and asked me to do it again because she had missed it.
I was about to tell her "Hell No," when I spied my sister behind her smiling and nodding.
So I did it again and this time a lot of people noticed. A third time. A fourth time.
Someone said, "is it just me, or is his butt blushing?"
I wondered if it was or if that was simply Maria's handiwork shining through from this morning.
After my fifth dive, the life guard blew her whistle and called out "enough already, I'm sick of looking at your ass!"
I was starting to think this was not going to be just fetching drinks for the girls!


AMY ENTERS THE PICTURE

I was left alone for a little bit, but couldn't help but feel like I was being looked at and discussed by a growing number of people. Then Erin came up to me and told me that I needed to walk into the changing room again.
"But I did that already," I whined.
"And now you are going to do it again. And this time, I promise it will be worth your while."
I had to admit, that piqued my interest a little bit.
Erin walked with me and as we got close to the entrance, she grabbed my arm and whispered, "not yet."
We stood there a few minutes listening to the muffled, echoed conversations on the other side of the wall. Somebody sneezed loudly and just like that, Erin propelled me into the room where I came face to face with Amy, who was topless.
She screamed, I screamed, everybody screamed!

“Get out,”Amy yelled. She looked at me with a shocked expression that quickly turned to hatred.
I started to explain when a chorus of "GET OUT" erupted.
I ran out of there and straight into Erin. "So, how'd that work out?"
I screamed at her that it had turned out horribly!
"Oh gosh," she said. "Was that your girl friend? Or maybe just a girl you have a crush on. Oh that is too bad. Okay look. You wait out here and I'll explain the whole thing to her."

I didn't trust Erin, of course, but what did I have to lose at this point? They had after all, set things right with Jon, so maybe there were lines even they wouldn't cross. And sure enough, a few minutes later Amy came out and wandered over to me. I was sitting at the shallow end of the pool, head down, trying to process the yin and the yang of seeing Amy topless. I mean, I saw her topless, but now she hated my guts...but, I had seen her topless!
She sat down next to me and gave me a sad little smile. "Erin told me about last night. About the pictures and everything."
I winced.
"She said she would show them to me if I needed proof."
I must have gone bug eyed, because she laughed and put her hand on my wrist and told me that she had declined the offer.
"Why don't we go over to the snack bar and you can buy me an ice cream cone."
Just then, another girl called out to Amy and waved her over.
“I'm just going to go say hi to Melissa. Why don't you go get us some ice cream and I'll meet you over there."

I was glad she took off. To my horror, between seeing her topless and then having her come sit right next to me and touch me, well, I was starting to get an erection. In my regular suit, this would not have been a problem, easy enough to shift and disguise, but in this suit it was barely contained, much less disguised. I slid into the cold water and that started to do the trick, that and the shock of hearing my sister say, "whatcha doing there?" with a giggle in her voice.
Before I could even answer, she said, "Jan and Erin have a little job for you."
I tried to beg off, explaining that I was going to buy Amy an ice cream cone."
"Well what a coincidence," she said, "that is pretty much what they had in mind."
Just then Jan and Erin strolled up. My sister took them both by the arm and pulled them away a little bit and started whispering animatedly to the two of them. It seems that my little predicament had not gone unnoticed by my sister and she was filling her two friends in on it. Jan and Erin threw back their heads in laughter and then looked my way. Jan crooked her finger at me, my signal to get out of the pool.
Not good.

"Your little 'ice cream date' with Amy will have to wait," Jan said. We started to walk over to the Snack Shack (where soft Ice cream cones, burgers, etc. could be charged to your parents account).
Amy saw me coming and looked at me quizzically and maybe a little hurt as I passed by.
"Do you see Becky and Donna over at that far table?" Erin asked me.
I looked and saw two pretty girls sitting at a big table with their boyfriends and three or four other couples.
"You are going to buy two ice creams cones and give one to each girl and this is crucial, you are going to say 'I just wanted you girls to know I was thinking of you.' If you don't say that exactly, your photos get distributed, no second chance. Got it?"
"Sure," I said. This didn't seem that bad. I mean it would be embarrassing and their boyfriends might threaten me, but I could handle all of this.

So we got in line to get the ice cream with about four people ahead of us.
"I got this," I said, feeling pretty confident, "you guys don't have to wait with me."
"Oh but we want to sweetie," Erin said as she gently raked my back with her nails.
"You have been such a good sport about this," Jan cooed in my ear, leaning into me and letting her breasts graze my arm.
If my mind hadn't yet figured out what was going on, my body was much quicker on the uptake. I stiffened and then I stiffened as the fabric on my suit began to stretch. Suddenly, the task at hand was raised to a Code Red!
As the fourth person stepped away, I stepped up to the counter in a daze, grateful at least that the girl behind the counter hadn't seen and now couldn't see anything. Jan and Erin were relentless. Really, they had me at first touch, but they weren't taking any chances.
"Isn't this exciting?, Erin said.
Jan looked down at my gapping suit and laughed, "Obviously he thinks it is."
I ordered the two cones, gave the girl my parents info and waited.
She handed me the two cones and thanked me.
"Jimmy, right? she said.
"Um yeah," I said.
"We had Ms. Walker together, 2nd period."
"Oh yeah," I said weakly. I took the cones from her and turned to walk away knowing that things were about to get really embarrassing.

It started a little sooner than I thought.
As I started to walk away, Jan called out sharply, "Jimmy, where are your manners!? Turn around and thank your friend."
So I turned back and said, "Thank you for the," but I was cut off by the girl laughing and saying "Oh My God!"
She was staring at my erection and without taking her eyes off of me, reached out and tapped the other girl she was working with on the shoulder who turned as if to say, "yeah, what," but followed her co workers gaze and also laughed and shrieked out her own "Oh My God!"
Now others were starting to take notice as I turned and headed for Becky and Donna's table which now seemed a hundred miles away.
Amid all the commotion I was causing, I snuck a quick glance over Amy's way. I regretted it instantly. She was sitting with Anna, Erin's little sister and a couple of other girls, all of whom were doubled over with laughter, but Amy was just staring at me with a shocked look in her eyes and her hand raised up to her mouth.
As I approached the table, everyone was already laughing, so when I reached out with the dripping cones and said, "I just wanted you girls to know I was thinking of you," everybody just roared.

I just stood there, not knowing what to do. They weren't taking the cones.
Finally, Becky, wiping tears from her eyes, said, "no thanks baby, we're not hungry."
Now I really didn't know what to do. Would I be punished if they didn't take them?
I was about to plead with the girls to take them when Becky's boyfriend came to my rescue.
"Here" he said, standing up and taking the two dripping cones out of my hands.
"First, let's see if we can't calm you down a bit." With that he stretched my suit away from my body a bit and flicked a glob of ice cream onto my erect penis and then let the suit snap back into place. Well that had the desired effect alright, and if it hadn't, dumping the remaining ice cream and cone on my head sure did.
He then took a bite out of the other cone and waved his hands at me as if to say "dismissed."
I turned to walk away and as I did so, he grabbed the back of my suit and chucked the remnants of the second cone in and gave my ass a big swat, sending ice cream and cone all over my ass and dripping down my legs.

All I could think about was getting to the changing room and getting all of this gunk off of me.
But before I could leave the snack area, Amy blocked my path and told me how sorry she was.
"That's, that's okay", I said, not able to meet her eye.
"That boy was so mean, and all those people laughing at you, you poor thing."
I knew Amy meant well, but she was inadvertently prolonging my humiliation.
Just then, Anna stepped forward and said, "serves you right asshole."
And then her two friends joined in, "yeah, Anna told us what you did to Amy you little creep."

Now let me just stop here and tell you why this situation was particularly galling.
Anna had conspired with Erin to set up Amy so as to set me up.
Anna's loud sneeze in the changing room was Erin's signal to send me in at just the right time.
So here is Anna, recruiting a couple of pals to admonish me for what I had done.
Had I not been so busy defending myself and trying to explain that all was good with me and Amy, I might have noticed that while these two girls did indeed appear to be furious,
Anna actually seemed to have a little twinkle in her eyes and just the slightest hint of a smile on her lips.
"Alright," I thought to myself, "I'm done here." I started to side step around one of the girls when she reached out and shoved her own cone into my face. The three of them laughed at me as ice cream clogged my nostrils and ran down my cheeks. Before I could really react, the other girl dumped a coke over my head.
People standing nearby laughed and applauded. Clearly, I was not a sympathetic character at this pool.
It was at this moment that Amy reasserted herself. She snorted out a quick laugh when she saw me and then regained her composure.
She took me by the hand and led me away from the gathering crowd.
"You might want to get yourself cleaned up," she said.
I then walked towards the Men's changing room with as much dignity as I could muster. No easy task with ice cream dripping off my face, my crotch and my butt. Not to mention the coke.
Oopsydaisy
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Re: The Humiliation of Jimmy

Post by Oopsydaisy »

And then it gets better, no wait, worse.

Once inside, I stripped off my suit and got under the shower.
Just then, the two guys who had called out "not cool" after I pantsed Jon, walked in.
"Well, well, look who it is" one of them said.
"Leave me alone," I said, "I just came in to take a quick shower. I'm going right back out.”
"Then why did you take your suit off?" one of them asked?
And then they started a conversation, excluding me.
"I think it's because he secretly likes being naked."
"He wants to be naked all the time. I bet he wants to go back out there naked, but he just doesn't have the guts."
"Poor little fella, he just needs a helping hand."
"A push in the right direction. A friend whose got his back."
"Hey, we could be those friends!"
"No," I yelled, seeing where this was going. "Please!"
"Aww, the little guy is begging for our help."
"I think we gotta help him."

And with that they each grabbed an arm and lifted me off the ground.
I was squirming and begging them to stop. We had exited the changing room and were now in a common area about ten yards from the pool. Another ten steps or so and I'd be naked at the pool. And then suddenly, there was Jon and Amy blocking our path.
Amy put her hand to her mouth and with eyes wide, gave me the once over.
Jon said, What are you guys doing?”
“We are taking your buddy on a tour of the pool, and by the way, you’re welcome.”
“Let him go,” said Amy.
“Don’t think so,” said the other guy.
“Well he can’t go out like that, he’ll be arrested.”
The two guys looked at each other and nodded. “Okay” one of them said, “if you can find a pair of underwear in the lost and found, he can wear that, if not, he goes out naked.”
I let out a sigh of relief, because I knew there were two baskets full of lost and found in the men’s changing room.
Jon started for the room when one of the guys, put an arm on his chest to stop him.
“ugh uh,” he said.
“Not you, her, in there.” He was pointing to the women’s changing room.
Amy looked at me with a sad face and mouthed the word “sorry,” as she rounded the corner into the changing room.

**And here is what I wouldn’t know until it was too too late.**

As Amy rounded the corner into the women’s changing area, I assume that frown turned into a giant grin. She must have been so exited, everything was going exactly as planned.
Yes, my sister, Jan and Erin had indeed confessed to her all that they had done to me, but they had told her that Jon’s pantsing and seeing her bare chested earlier had been all me! According to them, I had pantsed Jon because “misery loves company.”
As to seeing her, hadn’t I already been forced into the women’s changing area?
I had insisted on going back because I saw through the fence that Amy had arrived and, again, insisted on getting a little treat for myself.”
They then told Amy and Jon to “forgive me,” so they could be in a better position to gain my confidence and get revenge later.
And here they were, doing just that!

Amy comes out, again looking mournful and says “sorry Jimmy, this was all I could find.” And with that she holds up a a pair of light blue underwear with a white unicorn on the backside.
“Perfect,” laughs one of the guys. “Help him get them on.”
They lift me up a bit so that Amy can place each foot through and then shimmies them up my legs. If I wasn’t totally humiliated before, and I was, this takes it to a whole new level. From Amy seeing me naked, to having her put these little girl panties on me, to the feel of here fingers as they glided up my legs, I was actually glad these guys were holding me, because I don’t know that I could have stood by myself.

“Okay,” one of the guys said, “everybody happy now? Here we go.”
With that, we started moving towards sunlight.
“Jimmy, Amy called out, when you can, race for the exit and we’ll meet you outside with a towel.”
“Yeah dude, we’ll be right behind you’” said Jon.

And just like that I was carried out into the pool area. There were a couple of problems with the “run to the exit” plan.
First, I was still in the grips of the two guys and secondly, there was no path. Had I been thinking, instead of in a wild panic, this might have been the moment that I figured something was up. There were about thirty kids there, ready to greet me. Obviously, this was no spontaneous event.

One of the guys yelled out, “look who we found in the girls locker room!”
Everyone howled with laughter. At this point I was finally released and reflexively tried to cover myself as if I was naked, because I felt so naked! This caused even more laughter.
And right there were Emily, Jan and Erin. “You look adorable,” called out Erin.
“That explains all my missing underwear,” yelled my sister, obviously reveling in the moment.”
Jan then blocked my path, spun me around, yanked the panties down far enough to expose my butt and then gave me a hard slap on my right butt cheek.

As embarrassing as that was, it also gave me the incentive to get moving. I jostled my way through the crowd. It was no easy task, Jan had planted a seed and every yard or so I was spanked, pinched and/or had my undies snapped.
Finally, I made it to the turnstile and pushed, knowing that I was 180 degrees from freedom.

And then the turnstile quit moving. I couldn’t figure out what had happened. No one was holding me in. I looked around wildly and that’s when I saw that same pool employee who had falsely accused me of playing with the turnstile when I walked in. He was smiling at me, holding some piece of metal in his hand. I don’t pretend to know the inner workings of turnstiles, but obviously he had used this thing to lock me in place.
I thought back to my sister talking to him when we arrived, and wondered if all this had been set in motion back then.

Plans, plans.

“Please let me through,” I asked defeatedly, knowing that it wouldn’t be that easy.
“Well,” he said, “I’m thinking I’m going to need something from you.”
I looked around for Amy and Jon, but didn’t see them anywhere. I saw everyone else though. The crowd was starting to swell.
“I don’t have anything,” I said, head bowed.
“Oh I beg to differ,” he said.
“C’mon man,” I pleaded. Then remembering what Amy had just said to the two guys, I took my shot. “But I could be arrested for indecent exposure and you’d, you’d be an accomplice.”
He just laughed.
“Do you see any cops? C’mon now. Hand me the undies and I’ll let you through.”

“Undies, Undies, Undies!” Everyone was shouting.
I needed this to end. With my whole body shaking, I pulled off what little cover I had left and handed them over with one hand as I covered myself with the other, determined to thwart anyone seeing me totally naked.
That dream was short lived.

“Okay,” the guy said, here we go.”
Only nothing happened. “Hmm,” he said. “it seems to be stuck.
Oh I know, sometimes if you stand on it like this, and bounce up and down, it shifts the weight just enough to turn.”
With that, he put each foot on the lowest bar and then stretched his hands up and grabbed the highest bar he could.
“Well silly me, I can’t very well stand like this and get it to turn now can I?
But you know what, I bet if you stood like this, it would work.”
I sighed, and turned, exposing my butt to the crowd as I did as he instructed.
He laughed again. “Nice try hombre, but it’s only going to work on these bars,” he said as patted the bars that would have me facing the crowd.
I looked out and saw Amy and Jon working their way through to the front of the crowd.
They had no towel. Both of them were laughing and pointing at me.
Almost in a fog, I stepped onto the lower bar and stretched up and grabbed a higher bar. And guess what fit perfectly between two bars, leaving me totally exposed. The laughter went up another notch as I jiggled up and down.

As I sloooowly started to turn toward the exit, I saw my sister with a look of pure satisfaction on her face, Erin and Jan doubled over with laughter and tears streaming down their faces and Jon, with his arm draped over Amy’s shoulder, both of them laughing and Amy clapping her hands with glee.


Epilogue

Once the turnstile made a complete turn and dumped me outside of the pool area it sank in that I was naked and four blocks from home. Everyone was still laughing and pointing at me and now I was getting open mouthed stares from people just arriving.
In a panic I ran across the street and hid in some bushes while I caught my breath.

Well now what!? All I could figure out to do was walk home as quickly as I could.
Most houses had fences and dogs, so there was no “back way” or alleys. I would simply have to walk (run!) four blocks. I jogged by about two houses when a car turned onto the street I was on. I quickly dove behind another bush as it passed. I started again and then saw another car. This was ridiculous, I was barely making any progress.
Then, just as I was about to dart out again, I saw a cop car. I stayed where I was and watched it pass by. Coincidence or had someone called the cops? Now I was freaking out!

“Jimmy, is that you?”
I tentatively looked around the bush and saw Maria sitting in the passenger seat of the first car I had seen earlier. “See Rosa,” she said, “I told you I saw somebody.”
“Why are you naked?” She laughed.
“It’s a long story,” I said.
“Do you need a ride?”
“I looked at her car. There were two other girls in the back. I groaned, but really, what choice did I have. That cop might be coming back around any second.
“Okay” I yelled and sprinted towards their car, covering myself as best I could.
As soon as they saw me coming, one of the girls in back got out and opened the back door making it clear that I would be sitting in the middle.
“Thanks,” I said weakly as we started off.
“Oh our pleasure,” one of the girls in back said and they all laughed.
A few things struck me all at once. Maria’s english seemed much better than I remembered, there was a polaroid picture of her spanking me taped to the rearview mirror and I couldn’t help but notice that we were headed away from my house. What fresh new hell awaited me now?
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Jeepman89
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Re: The Humiliation of Jimmy

Post by Jeepman89 »

Funny turn of events! Love this story and it just got better!
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Re: The Humiliation of Jimmy

Post by Luca »

Very nice story. Thanks
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