For Age 18 and Older Only
Blondie's Humiliation Stories
Chapter 1: Shame Clothing
Fri Mar 7, 2008 5:22pm
71.202.144.81

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 diagramming sentences. Boredom was already setting in for the majority of the students, as they were entrenched in what looked like just another mundane Wednesday with Sister Ruth. But thanks to one of their fellow students, coupled with their teacher’s strong propensity towards enforced humiliation, this day would be anything but mundane.

The thirty-four year old Sister Ruth had been teaching grammar school for over eleven years. For the last year or two her job was starting to feel a little stale. The monotony of it all was setting in for her, and she longed for something to spice up her life. She knew she wasn’t going to find that “spice” in the convent, so she often looked to her students for her diversions. As alluded to, she took considerable pleasure in embarrassing, if not downright humiliating her students. She had recently started using her position of power for that purpose, but up until now, not quite to the extreme that she desired. There was the time earlier in the year that she punished one of her students by making him stand in front of the room and sing in front of the whole class. She remembered the pleasure she felt watching him blush profusely while singing his song.

Then there was the time she wrapped a woman’s scarf around another boy’s head. Again, she took extreme pleasure as his face grew redder by the second while she slowly tied the scarf under his chin and purposefully adjusted it until she was satisfied. She had conjectured that imposing female clothing on a young man might be one of the more powerful forms of enforced humiliation, and the boy’s extraordinarily embarrassed reaction to the scarf certainly confirmed that suspicion.

It had been over a month since she had utilized the scarf punishment, and since then she had been waiting for the opportunity to humiliate one of her students in a similar manner. Maybe today would be the day, she thought to herself earlier that morning. So when she spotted Tommy turning around and whispering something to the boy behind him, she decided to pounce on the moment. Little did Tommy know what the consequences would be of the seemingly minor transgression. As it would turn out, he picked the wrong day to make a false step.


Introducing Sally and Cindy

“Tommy, is there something you’d like to share with the rest of the class?” inquired Sister Ruth.

Tommy blushed slightly at the admonition. “No, Sister Ruth. Sorry, Sister Ruth,” answered Tommy.

A slight smile formed on the corner of her lip. This was the opportunity she had hoped for. “Well, ‘sorry’ isn’t going to be good enough, Tommy. Stand up, please.” Tommy, who was seated in the very front of the second row of students, apprehensively complied. “This isn’t the first time I’ve had to interrupt our lessons because of you, is it Tommy?”

Tommy shifted his weight uncomfortably. “No, Sister.”

In fact, it was quite true. Tommy, though generally a good kid, did have a habit of becoming restless when the subject matter didn’t interest him. Already during this school year Sister Ruth had punished Tommy on three different occasions. The first time he had to write one hundred times, “I will raise my hand before speaking in Sister Ruth’s classroom.” The second time he had to stand in the corner for an hour, which he found mildly embarrassing. The third time came on the day of his thirteenth birthday. On this occasion he had to wear a sign on his chest. Sister Ruth made it on the spot, writing in bold and capital letters, “I HAVE BEEN A NAUGHTY LITTLE BOY.” The teasing he received from his fellow students was relentless, especially during the recess and lunch periods. Tommy, embarrassed to no end, seemed to have a constant blush going throughout that day. That was more than a month before, and he had been very careful not to give his teacher an excuse to embarrass him again, especially in light of the fact that Sister Ruth’s punishments seemed to be escalating in their level of humiliation. When she tied a feminine scarf around the head one of his fellow students Tommy had cringed, and was ever so relieved it wasn’t happening to him. But now he watched his teacher reach into her drawer and pull out the very same scarf. He felt himself literally tremble with fear as Sister Ruth approached.

[Oh, there goes Tommy again, talking while I’m trying to teach. I think I’ll have a little fun with him…yes, he’ll be a perfect little victim…I’ll bet I can make him blush …ah, he’s already getting a little nervous while I’m reprimanding him…I think I’ll use the scarf…I do love the way they blush when I do this…get it out of the drawer here…oh, look at him, he’s already turning red…just wait until I wrap it around his pretty little head .]

{Uh-oh, she caught me talking…and she’s got a funny smile on her face…oh, no, she’s opening the drawer…she’s got the scarf!…oh, please, no, I’ll just die!}

It was at that moment that another student chose to become involved. The student was Tommy’s sister Sally. Tommy had pulled many a practical joke on his slightly older sister, and she had not been amused by any of them. Her intrusion would go a long way towards leading to Tommy’s fateful punishment. She raised her hand, and Sister Ruth stopped short of Tommy, somewhat annoyed at the interruption. “Yes, Sally?”

“Sister Mary Ruth, I think you should know that Tommy has done something much more serious than just talk out of turn in class. You may well want to consider a harsher punishment when you hear what I have to say.” Sister Ruth raised her eyebrows. She was now suddenly quite interested. In fact, she secretly was hoping to hear of serious misconduct on Tommy’s part, one that might warrant a severe, even more humiliating punishment.

Meanwhile, Tommy was becoming panicky, as he knew what his sister was about to divulge. The day before, during the morning recess, Tommy was walking by the drinking fountain with one of his friends. Laura, a fellow seventh-grader, was leaning over the drinking fountain taking a sip of water. Tommy, in an attempt to impress his friend, lifted Laura’s skirt, resting it on her back. The two laughing boys scurried around the corner before the startled and embarrassed girl could see who the culprit was. Tommy had thought no one had seen him, but that night his sister said to him, “I know something that will get you in deeeep trouble.” Tommy dismissed it at the time, but now it appeared his actions were coming back to haunt him.

“I’m listening, Sally,” answered Sister Ruth, somewhat anxiously.

“Well, you’ll be interested to know that yesterday Tommy lifted Laura’s skirt up and exposed her panties while she was leaning over the drinking fountain.”

Tommy clenched his eyes shut in anguish. Sister Ruth outwardly appeared riled, but inwardly she was thrilled with the possibilities that were presented by the revelation. She looked at Tommy accusingly. “Is this true, Tommy?” she asked with feigned irritation.

“No, it wasn’t me,” Tommy lied, desperate to recover from his increasingly dire situation.

Sister Ruth turned to Tommy’s victim, who was sitting on his immediate right. “Laura, did Tommy lift up your skirt yesterday? It’s okay, sweetheart, you can tell me.”

“I…I…somebody did it, but I didn’t see who,” answered the young, blushing girl.

It was at this moment that another student chose to contribute to the discussion, an overture that ultimately would seal Tommy’s miserable fate. The student was Cindy, Sally’s best friend. Cindy was a pretty little blond girl who sat immediately to Tommy’s left. Tommy had always had a crush on her, but she treated him more like Sally’s little brother than as a peer. She had also been involved as a victim in a couple of Tommy’s practical jokes. The two girls had talked about getting back at him on numerous occasions, but so far the opportunity hadn’t presented itself. Cindy, sensing that her immediate involvement would solidify Tommy’s guilt in the eyes of Sister Ruth, raised her hand.

“Cindy, do you have some insight into these distasteful proceedings?” asked Sister Ruth.

“Yes I do, Sister Ruth. I saw the dirty deed, too. Lifted poor Laura’s skirt straight up her back; her panties were out there for all to see. It was definitely Tommy.” She was lying, since at the time of the violation of Laura, Cindy was engaged in a game of volleyball around the corner from the drinking fountain. But Cindy’s fib notwithstanding, Tommy was now in serious trouble. Sister Ruth wore a look of agitation.

“Thank you, Cindy; you have been very helpful.” She turned to the troubled youth, who was now overwhelmed with dread. “As for you, young man…” She let the phrase dangle there momentarily as she contemplated how she would deal with what for her was a delicious situation. She held the scarf up. “I think, given the gravity of your offense, that we need to come up with a punishment that is a little more creative…something a little more embarrassing than this.” Tommy’s trepidation increased, while many of the students sat up in their seats, keenly interested in the scene playing out before them. “Yes, I do believe we can find something much more interesting for you to wear.”

[Yes! Sally and Cindy’s revelation really opens the door for me…bless their devious little minds …so the little perv is lifting up skirts, is he, checking out the girl’s panties…if he’s so interested in girls’ clothes then I’ve got just the thing for him…heh, heh…I’ve always wanted to pull out the nightie…forget this scarf…we’re about to escalate the humiliation…oh, this is going to be fun!]

{Oh, please, I’ll never talk in class again…please don’t put the scarf on me…what does Sally want…oh no, Laura’s skirt…she’s telling her!…Oh, God, Cindy’s backing her up…I’m in for it now…what does she mean, something more embarrassing for me to wear?…worse than the scarf?…oh, God!…what is she doing?!}


The Nightgown

Sister Ruth smiled to herself. She had already decided on a course of action. Two months before, she had stowed a nightgown in her desk drawer. It was the nightgown that she had worn when she was a young girl. She often fantasized about forcing one of her boy students to put it on as punishment, but she never had carried out the fantasy. She was concerned that there might be some backlash from the one of the students’ parents if word got out about what some may consider an act of depravity. But at this particular moment the need to satisfy her prurient desires far outweighed her concern about any possible repercussions.

“Yes, I’ve got just the thing for you, Tommy.” She stuffed the scarf in the pocket of her habit and walked purposefully to her desk and opened the bottom drawer. When she stood up, to the fascination of the students and to Tommy’s utter distress she was holding a long-sleeved, pink, flannel nightgown, femininely decorated with a darker pink floral design. She held it up and examined both sides. Seeming quite satisfied, she turned her attention to the cowering boy standing next to his desk. “Do you know what ‘shame clothing’ is, Tommy?” asked Sister Ruth.

Tommy frantically tried to extricate himself from this most disconcerting predicament. “I-I’m really sorry, Sister Ruth; I promise…I promise I’ll never misbehave again. Please, I promise.” His quivering voice betrayed his apprehension.

Sister Ruth wasn’t about to back down. “Answer my question, Tommy. What do you think ‘shame clothing’ refers to?”

“I g-guess it would be…clothing that…clothing that…that would…shame somebody.” The nervous student fidgeted noticeably.

“You are quite right, Tommy. And I’m sure when you’re on display wearing this nightgown for the class you will feel an extreme sense of shame. I think you’ll find this a very effective punishment,” she said as she strolled towards the wide-eyed and horrified Tommy. “I expect that you’ll be blushing like a little schoolgirl.” She stopped in front of Tommy and briefly looked down at the nightgown. “And you’ll look like one, too,” the grinning nun said with a laugh. While his classmates joined their teacher in laughter, Sister Ruth held out the garment for the very red-faced student. “Here you are, Tommy. I’d like you to go back into the cloakroom, strip off your clothes and change into this,” ordered Sister Ruth.

Tommy was frozen in his tracks. His arms remained at his sides, as he was too stupefied to move. Sister Ruth used that moment to assert her power and establish her dominance. With swiftness reminiscent of Muhammad Ali in his prime, she slapped the stunned boy across the face. The noise of the slap reverberated throughout the classroom, and the sting elicited a well of tears in Tommy’s eyes. It was obvious to Tommy that his teacher meant business. Tommy grudgingly reached out and took the nightgown from her hands. Sister Ruth continued with her instructions. “Now, I’d like you to go back into the cloakroom and take off all of your clothes, including your underwear. When you are naked, you’re to slip on your pretty new nightgown, then come out and show off your new look for us.” Sister Ruth looked Tommy up and down and used her imagination to envision the unfortunate lad naked, then in the female attire. She looked at Tommy’s blushing face and was unable to suppress a smirk. “Yes, I’m sure you’ll make quite the pretty little model, don’t you think so? ” She paused momentarily while Tommy fixed his stare to the ground, wallowing in his wretchedness. “Now, if you behave yourself then I’ll let you have your school uniform back in time for the morning recess. Move along now; you’ve wasted enough of our valuable time already. I’m sure your classmates are very anxious to see you in your new finery.”

  • Tommy's DebasementBlondie., Fri Mar 7 4:32pm
    • 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
        • 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
                • 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 :-))
    • 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., Sat May 14 1:11pm
        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., Sat May 14 1:24pm
          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 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
    • 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 HumiliationBlondie., Tue Apr 1 10:01pm
      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... more
      • 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 Clothing — Blondie., Fri Mar 7 5:22pm
      • 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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