Blondie's Humiliation Stories

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Chapter 5: Playground Humiliation
Tue Apr 1, 2008 10:01pm
99.7.175.77

Skipping Around the Playground

When the seventh grade class stepped outside to join the rest of the students, Sally and Cindy, grinning freely, each grabbed one of Tommy’s hands and began parading him around the girls’ side of the playground. Within a matter of moments there was a crowd of wide-eyed, giggling girls trailing the trio. The boys on the other side of the yard had halted their baseball and basketball games and were watching from a distance. Word quickly spread about Tommy’s earlier female clothing shame and subsequent stripping. There was a buzz in the air, and the excitement level was extraordinary. As all eyes focused on him, Tommy, blushing crimson, avoided eye contact with everyone.

Sally and Cindy, clutching Tommy’s hands securely, gradually started walking faster and faster, until they sped to a skip. Tommy walked briskly, occasionally speeding to a trot to keep up with the grinning twosome. “Skip with us, Tommy,” ordered Sally. “We promised Sister Mary Ruth you’d get some exercise. You want us to give Sister Ruth a good report, don’t you?”

Tommy had no choice but to follow the lead of his two tormentors. While he skipped around the yard the back of his skirt bobbed up and down, briefly exposing his ruffled panties with each skip. His attempts to hold the skirt down were rebuffed, as the girls had a firm grasp of his hands. Sally and Cindy were having the time of their lives while being cheered on by their appreciative audience. It was certainly a recess session no one would soon forget.


The Eighth Graders

Sally and Cindy eventually became winded, so they stopped with Tommy by a bench against the wall of the school building. Tommy used the opportunity to sit down, being careful to smooth down his skirt. Most of the girls were milling around in the vicinity of Tommy, very much absorbed in the unusual spectacle. Within moments after Tommy was seated, three girls from the eighth grade approached him. Two of them sat down on either side of him, while the other stood facing him next to Sally and Cindy. Not far behind them, a large gathering of girls looked on with considerable interest. Tommy was becoming more ill at ease by the second. The cute girl on his left spoke first.

“Hi, pretty boy, my name’s Karen,” she said as she ran her hand through Tommy’s blond hair. “This is Linda on your right, and that’s Nancy.”

“Please, just leave me alone,” pleaded Tommy while staring down to the ground.

“His name is Tommy,” Sally offered.

“Gee, Tommy,” teased Karen, “You’re dressed more like a ‘Tammy.’ May I call you Tammy?” Tommy started to get up, but Nancy persuaded him back down with a gentle but purposeful push to his shoulders. “Don’t leave, Tammy,” Karen said. “We’re just trying to be friendly. We heard you were quite the slut in class today, with your little striptease act. We feel like we really missed out. We’re thinking that since you showed your goodies to the seventh graders, then certainly you can put on a little show for your upper classwomen.” A look of fear swept across Tommy’s face. Although wearing the girl’s uniform caused him considerable humiliation, it sure beat the heck out of public nudity.

Tommy’s skirt had risen up a couple of inches when he sat down. Karen, eyeing Tommy’s thighs, ran the tips of her fingers back and forth across the top of his left thigh. “You’ve got very pretty legs, Tammy. Just like a little schoolgirl’s.” Tommy squirmed uneasily. “Feel Tammy’s legs, Linda,” continued the grinning Karen. “They’re so nice and silky smooth.”

Linda stroked Tommy’s right thigh. “Ooh, you’re right, Karen,” taunted Linda. “They’re smoother than a baby’s bottom. Probably as smooth as Tammy’s bottom. Can you show us your smooth little bottom, Tammy?” There was giggling all around as Tommy sunk deeper into the throes of his wretchedness. Then Karen’s hand delved a little higher up Tommy’s thigh, probing under his skirt. Tommy instinctively grabbed her wrist and pulled her hand away. Karen immediately slapped him across his face, marking the second time that morning that his face had been slapped.

“You keep your hands off me, Tammy!” warned Karen, “Do you hear me? You touch me again and we’ll strip off your girly clothes and have you skipping naked around the playground. From what I hear, it would be quite a site, your itty-bitty penis bobbing up and down for us all to laugh at.” Tommy now had tears in his eyes. “Oh, poor baby,” said Karen as she softly wiped a tear from his cheek with her thumb. “Did Auntie Kawen make you cwy?”


Nearly Stripped

Meanwhile, on his other side, Linda was surreptitiously working on the zipper of Tommy’s skirt. It had gone completely unnoticed by the unsuspecting Tommy that his skirt had been zipped as far down as it would go. Karen didn’t miss a beat. “All right, you can go now, Tammy,” she said. “I’m sorry. I didn’t mean to make you cry.”

Their plan worked to perfection. When Tommy stood up, the skirt instantly dropped to his ankles. Panicking, he bent over to pick it up, affording the giddy girls a marvelous view of his pantied behind. Karen reached for the back of his panties and managed to pull them down far enough to expose his buttocks, eliciting yelps of glee from the spectators and a cry of anguish from Tommy. He reached back with one hand to pull them up while struggling with his skirt with the other. But Karen continued tugging on the panties. In serious danger of having them pulled further down and possibly completely off, Tommy had to forego his efforts with the skirt to devote full attention to Karen’s onslaught. In doing so, the skirt dropped to the ground, and as Karen pulled, Tommy moved with her, causing him to step out of the skirt, much to the hilarity of the onlookers.

Meanwhile, Linda and Nancy swooped in to the aid of their friend Karen. Linda pulled upwards on the blouse while Nancy pulled on Tommy’s arms. “Let’s strip him!” cried Linda.

Tommy was in serious trouble. There was no way he would be able to stave off the attack much longer. “Strip him naked!” shouted an energized girl from the crowd, and when Sally and Cindy moved to join in, it seemed quite likely that they would do exactly that. Indeed, for one brief moment, Linda had the blouse pulled all the way up Tommy's back and from behind Karen had pulled the panties down to his knees, affording Linda a fleeting glimpse of the teenager’s prepubescent package and Karen a pleasurable view of his naked behind.

“No! No, please!” Tommy cried out in distress.

Then, for the first time all day, something positive occurred for the beleaguered Tommy. It was the classic “saved by the bell,” as the loud shrill rang throughout the schoolyard. The aggressors backed off, and Tommy quickly yanked up the panties and recovered the skirt.

“I saw it!” squealed Linda to Karen. Grinning derisively, she held out her thumb and index finger, spreading them about an inch and a half apart. Both girls laughed bawdily.

“Thanks for the sneak preview, Tammy,” Karen chortled as she walked past him while he was zipping up. “I saw your cute little butt, but it wasn’t nearly enough, you little tease. I’ll see you again at lunchtime.”

Tommy, unnerved, shuddered as he shuffled into the building amidst the throng of thoroughly entertained students.

Back in class, Tommy slinked into his seat, still wearing the girls’ uniform. It was time for math class, and he hoped to survive the whole period without drawing any more attention to himself. His hopefulness increased when Sister Ruth paid him no notice and said, “Pull out your math books, class, and open up to page ninety-two.”

It would be ten minutes into the lesson when Sister Mary Ruth pulled her calculated move.

“Okay, you’ve got x=2y + 7, and you’ve got…Tommy, why are you still dressed? Shouldn’t you be naked?” Tommy was at first shocked, then crestfallen. “Please come here, my little schoolgirl, so we can remedy that situation.”

The interest level of the students suddenly increased exponentially.

  • Tommy's DebasementBlondie., Fri Mar 7 4:32pm
    • Spin-Off(ish) Suggestionfundies123, Sun Mar 12 4:23am
      I absolutely adore this story, as well as the rest of your writings, but I have a question: have you ever considered doing a story in this setting, a teacher humiliating one of their students, but... more
      • Small breast humiliationrickkink, Sun Apr 9 3:52pm
        I think fundies123 has a wonderful idea. As a man, I adore women with small breasts. I think tiny titties are extra sexy. But not all women agree with this. A woman being humiliated because of her... more
      • Good IdeasBlondie., Mon Mar 13 9:11am
        I like your suggestions and would certainly enjoy writing a story or two with the teacher/girl premise. I won't rule it out, but I can't make any promises. Ah, so much humiliation to dole out, so... more
    • Chapter 18: The Final HumiliationBlondie., Thu Aug 25 1:50pm
      Belly Dance Instruction Tommy's mortifying trek down the gymnasium steps came to a momentary halt when he felt a tug on the back of his skirt. He turned around to see none other than Laura holding on ... more
      • Chapter 18: The Final HumiliationBlondie., Thu Aug 25 1:52pm
        The Disrobing Begins That is because the intrepid Karen, who had made no secret of her desire to see Tommy dance naked for her, had decided to take matters into her own hands. She had belly-danced to ... more
        • I Just Love That School!Hooked6, Sat Aug 27 3:50am
          Great ending to a marvelous story. I'm glad you added to it. Looking forward to reading more stories from you soon. You have such a wicked talent for humiliation and fun! Hooked6
    • Chapter 17: The Moment of TruthBlondie., Sat Aug 6 5:26pm
      Facing a Nemesis "I'm waiting," called out the eager Karen to the ill-fated teenager. Tommy quickly forgot about the throbbing pain in his freshly spanked backside as he came to the realization that... more
      • Oh, Karen...pixiemuledonkey, Thu Aug 11 9:53pm
        How i do love her. The delicious build-up to this moment was entirely worth the wait. As she said, it's all about the journey - i've loved her ever since she first tugged down the rear waistband of... more
        • Karen, Oh KarenBlondie., Fri Aug 12 3:50pm
          She is definitely one of my favorite dominant, humiliation-loving characters I have written about. I can feel her unbridled enjoyment as she inflicts her debasements on her chosen victim. Wouldn't... more
      • Chapter 17: The Moment of TruthBlondie., Sat Aug 6 5:28pm
        A Minor Reprieve But once again an unlikely source saved him, at least temporarily, from furthering his humiliation. "Hold it!" It was the voice of none other than Miss Richards. Betty Richards had a ... more
        • Re: Chapter 17: The Moment of Truthcaughtoflore, Tue Aug 16 10:42am
          Thanks for committing to return to this story. Not a single instalment has failed to bring me immense enjoyment.
    • Chapter 16: A Sibling SpankingBlondie., Sat May 14 1:52pm
      Confrontation With Miss Richards The sound was almost deafening as the tall, athletic high school volleyball player entered the gymnasium hand-in-hand with the slender, red-faced, seventh grade... more
      • morepleasing, Sat Jan 14 9:37am
        Please, Blondie. I'd like to see this story continue soon, too. Thank you.
      • next chapterrhysaford, Tue Jan 10 5:14pm
        Hi Blondie, I'm a huge fan or your story telling and you have such a talent for it. When is the next chapters coming for tommy's story.
      • Chapter 16: A Sibling SpankingBlondie., Sat May 14 1:53pm
        “Oh, you naughty boy!” shrieked Cindy when she became aware of Tommy’s elevated state of arousal. She looked up at Sally and grinned wickedly. “He’s getting a little stiffy!” While giggling, she... more
        • A Sisterly Squeezepixiemuledonkey, Thu Aug 11 9:46pm
          Ohh, Blondie...you are so skilled at raising the tension and raising the stakes of humiliations. i absolutely adored it when Cindy had Tommy straddle her lap and played with his teenie weenie while... more
        • morelongitude, Wed Jun 8 4:22pm
          ...and I'll beg for the next chapter if it will help.
        • brilliantlongitude, Sun May 29 9:49pm
          I've read some of these stories here, and elsewhere, but this is by far, my favorite. I was happy to check in and see new chapters. The sister angle is brilliant and increases the humiliation factor. ... more
          • Re: brilliantBlondie., Mon May 30 5:40pm
            I do see your point about making Tommy a little larger. Either way would be a huge source of embarrassment. It's already been established, though, that Tommy is lacking in the penis department, so... more
            • Re: brilliantlongitude, Wed Jun 1 11:41am
              I agree. It's been established. Maybe a zoom lens would help. LOL. I hope you write more soon. It's very good.
              • re: brilliantsailorbarsoom, Thu Jun 16 6:47am
                I suppose the boy could be more of a grow-er instead of a show-er, but yeah, he can't be sporting Big Wood.
        • Oh, the poor boy!sailorbarsoom, Sat May 28 10:10pm
          But I'm enjoying it. And looking forward to more! Any chance of Carlene's teammates getting into the gym just before the panties come off? This would not only be more people to see him naked (which... more
          • Re: Oh, the poor boy!Blondie., Sun May 29 1:59pm
            Carlene's teammates will definitely have to find their way into the gym. Like you say, the more that see him naked, the merrier, and the greater the humiliation. It's already been documented that... more
            • Tommypecs4, Sun Jun 29 6:40am
              Hi Blondie, I hope you are still alive. I am working on a "missing chapter" for Tommy's humiliation. It will involve the principal of the school, and other things. It will occur before the dance... more
              • Alive and KickingBlondie., Thu Jul 3 4:15pm
                I'm happy to say that yes, I am very much alive. Not writing much these days, but eventually that will change. Sure, I'd look forward to reading your "missing chapter." Please post it on the... more
                • Link to Stripping & Humiliation sitepecs4, Mon Dec 8 8:34am
                  Hi Blondie--It's been awhile but I'd FINALLY like to post the "missing" chapter of Tommy's debasement. However I cannot access the website you mentioned in your last post to me. Could you provide a... more
                  • S&H LinkBlondie., Mon Dec 8 9:37am
                    Looks like you found it, but here is a link for anyone having trouble: http://disc.yourwebapps.com/Indices/240409.html
                • Re: Alive and Kickinghufan, Sat Jul 5 6:49pm
                  Not past this point, I guess ;) Would love to read any additional chapter, by whomever. The story so far is one of the best I've ever read. Nice to see you back Blondie (or so we hope :-))
                  • Return?Bitter_Arron, Sat Jul 18 4:20am
                    Any word on the next instalment at all Blondie?
                    • Just No Time These DaysBlondie., Sun Jul 19 11:47am
                      I'm really sorry, but I just plain haven't had the proper time to sit down and write. I really do hope to free up some time and finish this story, but I can't honestly say when. Sigh.
                      • UnderstandableBitter_Arron, Sun Jul 19 11:52am
                        Fair enough. That makes sense, outside life very often takes presidence.
                        • Re: Understandableblockster, Sat Oct 31 6:29pm
                          Hopefully you find the time to pop a new chapter or two up eventually. It'd be a shame to never get a resolution to such a great story.
                          • It Will HappenBlondie., Sun Nov 1 4:11pm
                            Thanks, blockster. Trust me, it has bothered me to go such a ridiculously long time without adding to/finishing this story. I do see potential in the next few months to hopefully hunker down and bang ... more
                            • Blondie!Bitter_Arron, Sun Jan 17 4:28pm
                              Please come back Blondie, we miss your awesome work so much.
    • Chapter 15: Submission to a Volleyball PlayerBlondie., Sat May 14 1:06pm
      Facing Karen Tommy felt a tug on his elbow, and within moments found himself face-to-face with his nemesis Karen, who had been eagerly anticipating his return. “Well, here we are, Tammy,” said the... more
      • Chapter 15: Submission to a Volleyball PlayerBlondie., Mon Dec 15 4:05pm
        When Tommy turned away from Karen to make his ill-advised but understandable escape attempt, Betty Richards wasted no time. She reached for her cell phone, and while giving Sister Ruth a knowing... more
        • Chapter 15: Submission to a Volleyball PlayerBlondie., Mon Dec 15 4:11pm
          Carlene took a few breaths and, quite satisfied with herself, addressed the whimpering lad as she rose. “Stand up, little boy, I want to talk to you,” she ordered. Tommy, keeping his back to Carlene, ... more
          • Chapter 15: Submission to a Volleyball PlayerBlondie., Mon Dec 15 4:20pm
            Invasion of the Volleyball Players Just as Carlene was about to push the door to the gymnasium open, she had an idea. For her, it was a wonderful idea. Her companion, as he would soon discover, would ... more
            • Chapter 15: Submission to a Volleyball PlayerBlondie., Mon Dec 15 5:07pm
              The Twelve Peeks "Okay," continued Carlene. "Paula, would you like to do the honors?" Without hesitation Paula advance toward Tommy. She knelt down on one knee and looked up at the beleaguered lad,... more
              • Re: Chapter 15: Submission to a Volleyball PlayerTerwiliger, Fri Dec 19 1:36pm
                Wow. Just found this board today and this has got to be one of my favorite stories Ive read. You write REALLY well, cant wait to see how this all pans out
                • Thank YouBlondie., Fri Dec 19 4:40pm
                  Thanks so much for the feedback. It is much appreciated.
                  • Amazonian Antagonistpixiemuledonkey, Thu Aug 11 9:09pm
                    Up until this point, Karen had been my favorite character, but Carlene is the one who would have been my dream girl in school: nearly six feet tall, auburn hair, athletic, dressed in skimpy spandex... more
    • Chapter 14: Prelude to a StrippingBlondie., Sat May 14 12:52pm
      Tommy’s Debasement, Chapter 14: Prelude to a Stripping The Pink Bow As Tommy made his tortured trek up the gymnasium stands he spotted a little opening next to one of his friends. Trying to avoid... more
      • Chapter 14: Prelude to a StrippingBlondie., Sat May 14 12:53pm
        “That’s right, Tommy. You’ve given me no choice but to take your punishment to the next level. It’s time to render you completely………..and totally…………..nude.” She emphasized the word “nude” with a... more
    • payback?samos, Wed Mar 25 2:22pm
      Hi Blondie, is there a possibility for Tommy's payback? I would like to see humiliation of girls, teacher sister Ruth... etc.? I am pretty sure that they need to get their lesson:-) in front of... more
    • Re: Tommy's DebasementAlex C, Sun Jul 27 8:50pm
      Great job! I look forward to future chapters. I particularly like the chapters with the volleyball beauty in it. I hope she takes a bigger role. Also Leslie and the bully Danny really add to the... more
    • Chapter 13: Depantsed AgainBlondie., Sun Jun 8 11:42am
      The Shuffle Tommy continued to go through his steps at the guidance of Miss Richards, much to the amusement of his audience. His tee shirt was tucked into his white briefs, and his pants were... more
      • Uh oh just underpants??!!toastershout, Mon Jan 23 7:35am
        I love the moment when he's in just his underwear and he feels her starting to tug his T shirt out of his briefs ... he knows that soon he's going to be stripped to just his underpants in front of... more
      • Fan artsTsupandurwei Raewrednu, Sat Jul 26 1:10pm
        Hello Blondie! I read the Tommy's saga and I really enjoyed it. Thank you for your amazing work. These are some fan arts I did after read. I love this chapter in particular. X3... more
        • Re: Fan artsTsupandurwei Raewrednu, Sat Jul 26 2:15pm
          http://sta.sh/03qpvmuyq47
          • Re: Fan artsBlondie., Mon Jul 28 8:51am
            Thanks. Nice to have some nice artwork to go with the story.
    • Chapter 12: The Dreaded Dance ClassBlondie., Sat Jun 7 5:17pm
      The Gymnasium “Okay, class, it’s time to go down to the gymnasium for dance class with Miss Richards. I’m going to come down and join you today to see how you’re all... more
    • Chapter 11: The Spanking GauntletBlondie., Sat May 31 12:13pm
      Tommy’s Debasement, Chapter 11: The Spanking Gauntlet Rulers at the Ready Sister Ruth removed the panties from Tommy’s head and deposited them in her drawer. Tommy stood in the front of... more
    • Chapter 10: Forced Outside NakedBlondie., Wed Apr 23 5:20pm
      A Strip on the Teacher’s Desk After the lunch bell rang, Sister Ruth mused over how to spend the next hour before the 2:00 dance class. The devious plan she and Betty Richards devised called... more
      • Re: Chapter 10: Forced Outside NakedElbow, Sat Apr 26 8:52am
        Blondie, I remember part of this from the old site. It is absolutely brilliant and I can see why you have such a great reputation for story telling. I don't think I ever read the ending though so... more
    • Chapter 9: Sisterhood of HumiliationBlondie., Tue Apr 8 6:09pm
      Reminiscences of Humiliations Gone By During the lunch period, Sister Ruth spent most of her time gazing out her window. Her view was of the girls’ play yard, and she was enjoying the... more
      • Chapter 9: Sisterhood of HumiliationBlondie., Tue Apr 8 6:10pm
        “Thank you,” she giggled. “And please, call me ‘Ruth.’ Anyway, I told him to face me and put his hands behind his head. He was reluctant, but I think he understood that... more
    • Chapter 8: Girls' Lunch Meat: TommyBlondie., Mon Apr 7 5:23pm
      A Reunion With the Eighth Graders Tommy walked apprehensively with the girls out to the schoolyard. They were all carrying their lunches, though Tommy, quite understandably, didn’t have much of ... more
    • Chapter 7: The Girls' BathroomBlondie., Mon Apr 7 4:57pm
      The Training Bra It was noon, and the dreaded lunch hour had come for Tommy. As expected, Sister Ruth reached into her drawer and pulled out the girls’ uniform. Again Tommy had mixed emotions.... more
    • Chapter 6: Forced to EntertainBlondie., Mon Apr 7 7:53am
      A Slow, Torturous Stripping Tommy, with his head bowed, slowly walked up and faced his teacher. He figured he’d be told to take the uniform off, but it appeared she had something else in mind.... more
      • Re: Chapter 6: Forced to Entertainlongitude, Wed Jun 1 11:38am
        The use of the desk here, and the stool in Chapter 4, really add to the display factor, and heighten the humiliation. You write well. Thank you.
    • Chapter 5: Playground Humiliation — Blondie., Tue Apr 1 10:01pm
      • Tommys RevengeBlake, Fri Apr 4 1:29pm
        Hi Blondie, I hope you will also repost Tommy's revenge stories as well.
    • Chapter 4: Anatomy LessonBlondie., Tue Apr 1 9:46pm
      Please see below.
      • Chapter 4: Anatomy LessonBlondie., Sat Nov 19 2:40pm
        The Reluctant Model There was no way out for Tommy now. Resigned to his fate, but with an extreme sense of dread, he slowly turned around and faced his fellow students. It was an excruciating moment... more
      • Chapter 4: Anatomy LessonBlondie., Tue Apr 1 9:48pm
        “Sister Ruth, I have a question about the total lack of hair.” She addressed Tommy, who was now in the throes of wretchedness. “Sorry, Tommy, I noticed your face turned even redder... more
    • Chapter 3: Naked in the ClassroomBlondie., Tue Mar 11 6:50pm
      Nightgown Stripped Off Tommy walked briskly back to his desk and sat down. He sensed the grinning gaze of Cindy on his left, but he avoided eye contact with her. Sister Ruth began the history lesson... more
      • Chapter 3: Naked in the ClassroomBlondie., Tue Mar 11 6:53pm
        Tommy cowered before his teacher, looking straight down at the floor, his hands over his crotch. He knew that Cindy was just a couple of feet behind him. He shivered slightly as he considered the... more
    • Chapter 2: Nightgown Up, Underpants DownBlondie., Sun Mar 9 3:11pm
      Taunted in the Nightgown Back in the cloakroom, Tommy could hear the buzzing emanating from the students. With considerable trepidation he poked his red face out and saw the faces of thirty-five... more
      • Chapter 2: Nightgown Up, Underpants DownBlondie., Sun Mar 9 3:12pm
        Underpants Hauled Down Sister Ruth turned Tommy back around so he was facing her again. “I think we’ll proceed with our English lesson now, class,” Tommy heard her say. It appeared... more
    • Chapter 1: Shame ClothingBlondie., Fri Mar 7 5:22pm
      Sister Ruth’s Propensity It started out as a normal school day in Sister Ruth’s seventh grade classroom. The first hour was devoted to English, and the nun was droning on about... more
      • Chapter 1: Shame ClothingBlondie., Fri Mar 7 5:24pm
        [My, the look on his face when I pulled out the nightgown…like a frightened kitten …oh, he won’t take it…I’ll show him…I hate to slap him, but he needs to know... more
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