Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Recent Inactive Sissy Stories => Topic started by: sissyboy1212 on October 26, 2021, 07:58:54 PM
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I enjoyed revisiting Clarissa a little while ago, and I decided to check in with her again for Halloween. This is a multi-part story, and all the parts will be posted in the coming week (5-6 parts in total are planned).
These events take place several years ago when Mike was 15. It was late October...
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PART 1
Glumly, Mike Bradley winced as his mother yanked at his hair again.
“This is long overdue anyway, Clarissa,” his mother observed with little sympathy for his plight. “You’ve let your hair become a tangled mess, so I’m afraid you’ll just have to sit still until I finish brushing it out.”
“Yes Mother,” the subdued fifteen year old meekly replied. It was early Saturday morning. Instead of sleeping in as usual, he sat nervously before a fussy vanity table. He was back again with his mother in the ultra-girly guest bedroom where Clarissa always stayed. He glanced over and for the umpteenth time saw that photo he detested… the one with Clarissa in her precious pink Easter dress and girly pink hairbows. His room had already been locked up and was now off limits.
Mike watched in the mirror while his mother continued brushing all the tangles from his long brown hair. The lavender nylon beautician’s cape around his neck was uncomfortably tight, but he didn’t want to say anything about it and risk annoying her further. She had been furious when she got the call yesterday, and he knew Clarissa was going to stay a while. He had really stepped in it this time.
Carol Bradley worked meticulously with her hairbrush and then her styling comb until Mike’s hair was finally tangle-free. She decided she needed to comb in a little conditioner to make it a bit softer and shinier. Finally, she combed it all straight down so that it hung nicely and she could work with it. Now that she had Clarissa back in the house, her mood had improved somewhat.
Her initial reaction to that phone call yesterday had been shock and disbelief. Then, her mood turned to anger. When she had gotten Mike back home, she had just restricted him to his room with the warning that Clarissa would be here today. Last night, she knew she had to calm down before taking further action. She was extremely disappointed by the situation that had brought all this on, but seeing Clarissa always brightened her spirits. Looking at her teenager’s brunette hair, she noted with satisfaction that it touched his narrow shoulders now. The longer hair opened up so many more adorable possibilities.
“I think it’s grown long enough to do some French braids darling,” Carol said after some thought. “Wouldn’t that be lovely?” she asked her sissified teen.
“Oh yes, Mother,” Mike answered softly. His mother made eye contact with him in the mirror but said nothing. After a silent pause, she pointedly cleared her throat. Clearly, more was expected. Mike reddened slightly and rushed to add, “Thank you, Mother, I would just love that. French braids are so cute! I can’t wait to try them with my longer hair.”
His mother’s face softened a bit and she said, “That’s better dear.”
He watched in the mirror as his mother parted his long hair straight down the middle. She used an elastic tie to keep the left side out of her way while she went to work on the right. Chagrined, Mike sat motionless as she began braiding his hair. At this point, the usual humiliation set in and he felt his groin start to tingle.
She worked methodically, and the flustered teen was keenly aware of how tightly she was pulling his braids. She repeatedly tugged harshly as she made her way down to the base of his scalp. When she got down below the nape of his neck, she reached for another elastic tie. She used it to secure his new braid close to the base of his head, and she left the last couple of inches unbraided in a sweet little pigtail which dangled down the side of his neck.
“There Clarissa, I think this is going to work out beautifully,” his mother observed. “Your braids must be tight so they will stay properly in place,” she explained cheerily, “I simply won’t tolerate you mucking around with unkempt hair!” She then asked pointedly, “We can’t have that now, can we dear?”
“Oh no Mother,” Mike replied at once. Nearly choking on the words, he added, “I want to make sure my braids are neat and tidy.” Watching his reflection grow progressively more sissyish only intensified the tingling down below.
“Very good, dear,” his mother replied approvingly, “now for the other side.”
Mike sat on pins and needles as his mother repeated the process on the left side. In no time, his hair was done up in lovely even French braids ending in two adorable little pigtails. He shut his eyes tightly as she sprayed his braids liberally with hairspray to secure them in place.
“Now for the finishing touch,” she announced. Using two lengths of bright red ribbon, she tightly tied off his pigtails with playfully girlish bows.
Appraising her handiwork, she said “Any little schoolgirl would envy those braids and pigtails, Clarissa. Simply precious!”
“I love them, Mother thank you,” Mike said as his heart sank. Staring at the girlish vision in the mirror, he immediately knew she was right. He looked nothing like a fifteen year old boy. With this sissyish hairstyle, he looked just like a prim and proper little schoolgirl. That, of course, was exactly what his mother wanted. Clarissa was always expected to be a perfect goody two-shoes. The worst part of this was that a hidden part of him obviously desired it too.
After a moment, his mother unsnapped the nylon cape and set it aside. “Stand up dear, and let’s see your whole look,” she instructed eagerly.
Weak in the knees, Mike slowly stood and stepped to the freestanding full length mirror. Carol noted how easily feminine and graceful his movements had become. She had carefully nurtured Clarissa’s mannerisms in him for years. By now, they were practically second nature. With his mother beaming by his side, the feminized teen gaped at himself in the mirror and shuddered involuntarily. As always, it was horrendous.
His new schoolgirl braids and pigtails went perfectly with the rest of his outfit. Dressed in a charming school uniform, Mike looked just like a little girl ready for her first day of class. He wore a crisply starched short sleeve white blouse with a rounded Peter Pan collar. The collar was accented with cutely understated lace scalloping detail around the edges. A large and beautifully floppy ribbon bow matching his hairbows was knotted fussily under his collar. The loose ends of the girlish red bow dangled sweetly down the front of his blouse.
His fingernails glistened with a fresh coat of clear polish. Colored nail polish, of course, was not permitted with his uniform. He also wore a pair of tastefully subdued and feminine pearl stud earrings. He regretted now that moment of rebellion a few months ago when he got his ears pierced and came home with a pair of goth-style silver skull earrings. His mother had looked at him curiously, but she hadn’t really commented at the time. In retrospect, he obviously hadn’t thought that decision through.
Over his white blouse, he wore a classic red, black and white plaid jumper dress featuring a pleated skirt that reached just to his knees. The smart plaid jumper was fussily tied at the waist with a black ribbon in another neat little bow. Thankfully, his skirt was just long enough to hide his frilly white rhumba panties as long as he sat with care. Of course, the skirt puffed out beautifully due to the white tulle petticoat underneath. It tickled his bare legs and rustled with even the slightest movements which only heightened his shameful excitement. Looking down, he saw his knee-high bobby socks remained neatly in place. Similar to his blouse, the white socks also had scalloped white lace on their darling fold-over cuffs. The clingy cotton/nylon/spandex blend of the socks hugged his slender legs tightly and didn’t sag a bit. To complete his utterly girlish look, a pair of glossy black patent Mary Janes were snugly buckled on his petite feet.
From head to toe, he was a picture perfect little schoolgirl now. Sighing gloomily, he awaited the inevitable. He had a fairly good idea of what would come next. After all, it wasn’t his first time wearing this uniform. Once again, his mother’s skill with alterations ensured it still fit him to a tee.
“Well Clarissa I think that should do it,” his mother announced with satisfaction, “you look absolutely darling.” She continued, “I doubt you’ll need your blazer in the house, but bring it along in case you get chilly. Mike glanced at the recently tailored girls uniform jacket hanging by the door and grimaced. Freshly pressed, the dressy black jacket sported cute red piping and ostentatious brass buttons.
Slightly smiling now, Carol addressed him again, “We’ll eat a quick breakfast, and then I’m sure you’ll be eager to get to your lessons, dear.” Mike’s spirits sank further as he waited for her to say it. Pausing, she looked him over carefully as if trying to make a decision. Mike’s blushing grew more prominent, and he fidgeted fitfully while he waited for her to speak. “I think we’ll start today with some lines, Clarissa,” his mother finally concluded.
After a brief hesitation, Mike reluctantly faced his mother. Carol’s spirits rose instantly as she watched her prettified teen drop into a delightful little curtsey. She allowed herself a moment of satisfied reflection: These lessons were extremely hard fought. It pleased her greatly to know they still held fast. Years of repetition and practice had made these motions almost automatic for him. Daintily holding his skirt out by the hem. Placing one foot sweetly behind the other. Bowing his head. Bending his knees and dipping his body gracefully forward. It had all progressed to the point that she noticed he sometimes did it accidentally even while dressed as a boy. It was so reassuring for her to know that this sweetness was always just beneath the surface no matter how naughty Mike might be.
“Yes Mother,” Mike said softly before rising from his curtsey. Subdued now, he gracefully gathered his uniform blazer and followed his mother downstairs. Clarissa was back.
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I absolutely loved 'Clarissa's Visit' as well as the Prequel to the story. Creative and beautifully written stories that touch on my favorite theme of a dominant mother and a reluctant but weak son. Thank you so very much for this Halloween addition!
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Thank you jenniesissy! I appreciate your feedback and I'm glad you are enjoying the story. The next part will come later today.
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PART 2
Carol Bradley had barely gotten home from work on Friday when her phone rang. It was shortly after four and she noticed Mike was still not home. She answered the phone, and her mood quickly darkened.
“Mrs. Bradley, my name is Jeannette Elkins. I’m the manager at Belmont Pharmacy and Drugstore,” the caller began. “Are you Michael Bradley’s mother?” she asked.
Somewhat taken aback, Carol replied, “Yes I’m Carol Bradley, and Michael is my son.” With sudden concern, she asked “Is Mike OK?”
“Mrs. Bradley… Carol…” Jeannette continued hesitantly. First, she answered Carol’s immediate concern, “Yes Michael is fine. He’s here with us at the store now.” Then she added, “I don’t believe you and I have met, but I’m sorry to tell you he’s unfortunately caused a bit of trouble.”
“I see,” Carol said evenly. Her concern rapidly turning to annoyance, she continued as calmly as she could, “Please tell me what happened.”
Jeannette explained that Michael and one of his friends, Kyle, had been caught shoplifting at the drugstore. They had shoved several packages of miniature candy bars from the Halloween displays under their jackets and also took some cheap cologne. They were caught when Kyle tried to sneak behind an unattended counter and pilfer a pack of cigarettes. It was all captured on video, Jeannette informed her. She had called the police when they ran, and they were rounded up in short order.
Since it was such minor stuff and all the items were recovered, Jeannette decided not to press charges. Unfortunately for Kyle, he had already been involved in some prior incidents, so the policeman cited him and took him to the station. As it was Michael’s first offense, however, they would release him to a parent or guardian with a warning citation if Jeannette agreed to it.
Thus, Michael sat in Miss Elkins’ office now. Red-faced and dreading what was coming, he listened while the manager spoke to his mother.
“Thank you… Jeannette. I’ll be there right away,” Carol said and then hung up. Her hands were trembling. Why on earth would Mike do something so stupid? It surely had to be some sort of misunderstanding. She had to get hold of herself. She grabbed her keys and drove to the drugstore.
When she arrived at the store, however, one look at Mike’s face told her there was no misunderstanding. She knew he was guilty as charged. The events after that were a blur for both of them. She thanked Miss Elkins for her lenience and promised to follow up with her. She assured her Mike would learn his lesson. “His lessons…” she thought as she began to calm down.
They drove home in near silence. Mike stewed. Carol fumed.
At one point, Mike began a weak protest, “Mom I didn’t…” But then he stopped. His voice quickly trailed off. He couldn’t even finish the lie and just stopped. His mother gave him a withering look and arched her eyebrow. She sniffed curtly and turned her attention back to her driving.
When they got home, Carol could only trust herself with a few words: “Go to your room, Michael. You can make a sandwich for dinner before you go. You’ve displayed incredibly poor judgment and an appalling lack of maturity. We’ll discuss it tomorrow.” Then she followed with the words Mike had been dreading since he was caught, “Of course I’m sure you know by now, but Clarissa will be here tomorrow morning. Early. It’s not open for discussion, dear. Good night.”
With a hollow feeling in the pit of his stomach, Mike dreaded what awaited him tomorrow. He knew, however, it was all his own fault. Dejectedly, he trudged to his bedroom which he knew would soon be off limits. He slept very fitfully.
And so now it was early on Saturday morning. The clock showed just a few minutes before eight. Mike was immaculately dressed as an absolutely precious and prissy little schoolgirl while he picked halfheartedly at a simple breakfast of oatmeal, juice and fruit. Dismayed by thoughts of the day looming ahead, the petticoated teenager had little appetite. He hated to think about how many more Saturdays he was going to lose. He could hear his mother moving some things around in the adjacent den. Unfortunately, he knew exactly what she was doing. Absent-mindedly, he reached up and brushed his new pigtail. He was very conscious of the unfamiliar tightness of his pretty French braids.
When the kitchen clock’s hands ticked to eight, he heard his mother’s voice, “Clarissa, don’t dawdle, dear! You’ve had plenty of time to finish your breakfast.” Continuing, she ordered, “Come into the den right away, please. It’s time to start your lessons!” Belatedly, he looked up suddenly and realized he had lost track of time. He was already late.
Hurriedly, the sissified teenager dabbed his mouth with the cloth napkin and left it folded by his half-eaten breakfast. Then he scurried quickly into the den. He felt his petticoat tickle and swish with each dainty step. Of course, he saw what he had expected.
His wooden school desk had been moved over to the center of the den. His mother had found it at a thrift store a few years ago. It was an old-fashioned writing desk with a walnut finish and a separate wooden chair. Next to the vintage desk was a free-standing chalkboard she had picked up months later. On the desk, he saw a thick stack of ruled loose-leaf notepaper and the little cup holding Clarissa’s pencils and pens. He grimaced. It was time for his lines.
“Well take your seat dear,” his mother directed, “you’ve wasted quite enough time already!”
“Yes Mother, of course,” Mike said as he felt his face grow hot. After another quick little curtsey, he hurriedly took his seat at the small wooden school desk. He was keenly aware of the tulle petticoat tickling his bare legs when he sat. Smoothing his skirt nervously, he tried to sit up straight and keep his legs close together. By now, he knew better than to lean lazily against the back of the chair. The combination of nerves and embarrassment made his groin jump again. He hated that this had begun to happen more and more frequently during his stints as Clarissa. He adjusted his plaid skirt again—much more gingerly this time. Finally, he looked tentatively up at his mother.
When he met her gaze, he squirmed uneasily in the wooden chair causing his petticoat to rustle again.
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PART 3
Carol was of two minds at the moment. On the one hand, she was gratified to have her delicately girlish child back with her again. On the other, she was still quite upset at Mike’s misbehavior. She decided this refresher would do them both some good. Somewhat impatiently, she began, “We will obviously need to improve your punctuality, Clarissa. As you know your lessons always begin promptly at eight.” Without waiting for an answer, she continued, “As I said earlier, we’ll start today with some lines. After what you did yesterday at the drugstore, you obviously have lessons to learn. Stealing? Honestly, sometimes I think you almost try to get into trouble!”
As his mother lectured him, Mike shivered and felt a bead of cold sweat run down his back under his blouse. He cast his eyes down in humiliation. He had no good excuses. Idiotically, he had just been trying to show Kyle he wasn’t a chicken. He knew it was stupid to respond to that dare, but he hated being seen as a wimp. It pained him to think what Kyle would say if he could see him now. Mike just tried to concentrate on maintaining his girlish posture. His shiny Mary Janes were already growing uncomfortable.
His mother began writing on the chalkboard with a piece of white chalk. The clicking sounds of the chalk instantly triggered memories of previous unhappy lessons at this desk. He watched in silence as she wrote. The first sentence was expected. It was always something like that. The second sentence caused him a little angst since it was somewhat longer than normal. But then she wrote a third and he groaned inwardly. He’d never had to do three before. This would easily take half the day. Miserably, he read the three sentences he would soon copy line after line:
“My name is Clarissa, and I have been very naughty.”
“I am ashamed for stealing from Miss Elkins at the drugstore.”
“I will learn from my mistakes and try my best to be a good little girl.”
“Let’s start with two hundred, Clarissa,” his mother said dispassionately. “After that,” she added sternly, “we can see where we are.”
Crestfallen, Mike replied in a very small voice, “Yes Mother.” The prettified sissy took his purple pen and slowly began his lines, carefully numbering each one. With time and correction over the years, his handwriting had evolved from a nearly indecipherable scrawl to a feminine cursive with expressive flourishes. He worked painstakingly to copy the sentences neatly and precisely. His stiffly starched collar itched, and he felt cool air under his pleated skirt. He was also increasingly aware of the other familiar sensation. Dismayed, he remained unmistakably aroused in his ruffled panties.
As the morning dragged on, his mother frequently popped in to check his progress and make sure he didn’t slouch or dangle his legs lazily. Occasionally he crossed his ankles in a very girlish way, but he was always mindful to remain modest and sit up straight. This all made writing more difficult, but he was well practiced in how to sit like a young lady. He made slow but steady progress. After the first 50 lines, his mother rejected several of them for sloppiness. “You’ll need to redo numbers 9, 29, 32 and 49 Clarissa,” she chided, “I know you can do better than that.” His mother used a red marker to put an “X” next to the lines that were unsatisfactory.
Time slowed to a crawl as he spent all Saturday morning copying line after laborious line.
Finally, well past noon, the sissified teen finished his lines to his mother’s satisfaction and they had tuna salad together for lunch. She was in a better mood now. “I am so enamored with your French braids, dear,” his mother complimented him, “I just love how sweet they are on you!”
“Oh Mother thank you! They make me feel so pretty!” Mike said submissively. Dressed as he was, he remembered now that the more he embraced his situation, the sooner it was likely to end. And of course, to his shame, part of him truly seemed to crave it without any pretending.
After lunch, his mother announced, “Clarissa, now that you’ve practiced your handwriting, please return to your desk. Instead of more lines, I think you should write a nice note of apology to Miss Elkins. She was kind to let you off so lightly.”
Although his hand was still tired from the morning’s work, Mike nevertheless replied at once, “Of course Mother. I really want her to know how sorry I am.” He was thankful at least that it appeared he was done with lines. Just as quickly, however, he came to a painful realization: His mother intended this note to come not from Mike… but from Clarissa! Only a very small circle of people besides his mother knew about Clarissa. Mike agonized as he realized that circle would expand now. Intuitively, he knew every time Clarissa was introduced to someone new, it was less likely she would ever truly leave.
Mike plodded through numerous cringeworthy drafts of his note. Each time he completed one, He stood demurely in front of his mother and read it aloud. Finally, after several "suggestions," he had one that passed muster:
“Dear Miss Elkins,
My name is Clarissa, although you met me yesterday as Michael. I am very sorry for stealing the candy and cologne from your drugstore. I am so ashamed of my actions. If there is anything else at all I can do to make amends, I am more than happy to do it. Please accept my sincere apologies. You were generous to be so lenient with me. I promise to be a good little girl from now on.
Gratefully,
Clarissa Bradley"
It was now late in the afternoon. Mike was tired but still dressed in his darling schoolgirl uniform. Using his neatest cursive, he had painstakingly written his apology note to Miss Elkins on a light gray sheet of stationery with his purple pen. Finally it was done. After his mother reviewed his work, he folded it and placed it in a pale pink envelope. As he addressed the envelope, he resigned himself to the fact that Miss Elkins would soon know about Clarissa. At least it appeared this miserable day was coming to an end.
“Go put on your coat, dear,” his mother said unexpectedly, “it’s cool outside.” Mike flinched. He was worried to realize his mother was taking him outside now. He had thought this day was over, but his mother continued, “It’s a wonderfully sweet and appropriate note, Clarissa. It will mean more when you deliver it to Miss Elkins in person.”
Panicked, the teenaged boy’s heart starting beating rapidly. For a fleeting moment, he decided to resist. He would finally stand up to his mother! This was just too much!
But just as quickly, tears of frustration welled in his eyes as he knew he wouldn’t. Already his will was fading. He was acutely aware of his pigtails with their adorable red bows. He looked down, and his glistening black Mary Janes seemed almost to be teasing him. They looked so girly with his pretty ruffled knee socks. The thoroughly feminized teen felt his petticoat rustle again, and his face warmed once more as another unwanted tingle ran under his skirt. Unable to think or speak clearly, Mike surrendered as Clarissa took over. He put on his smart school uniform jacket with the cute red piping. After he buttoned it, he fluffed his floppy red bowtie and smoothed his pleated skirt out of sheer habit.
Pleased to see Clarissa’s feminine nature easily overpower Mike’s pitiful posturing, Carol smiled. “There’s a slight chance of rain this evening, dear,” his mother went on, “you’ll need to bring your hat along just in case.” Obediently, Mike went to the coat rack to retrieve his matching uniform hat. The petite bowler-style girls hat was made of black felt with a bright red hatband.
Trembling slightly, Clarissa dutifully followed her mother out the door.
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PART 4
It was late in the day and almost closing time when Jeannette Elkins heard the bell ring in front. She supposed she would have one last customer today. Since the afternoon had been slow, she had let the cashier off early. She walked to the front of the store to take care of it herself and was surprised to see Carol Bradley again. Carol was accompanied by a young girl in a dapper school uniform. That was strange. Jeannette could have sworn that Carol had said yesterday her son Michael was an only child. A moment later, Jeannette’s jaw dropped as she recognized this girl in the cute plaid jumper and knee socks.
“Hello again, Jeannette,” Carol said warmly. “I’m sorry again for all the trouble yesterday,” she added.
“Carol… that’s Michael isn’t it?” she asked haltingly. As she looked closer, it was clear that this was the same misbehaving teenager who fidgeted nervously in her office yesterday while she called his mother. She was confused as to why he was dressed this way, but she was also amazed at how feminine he looked. If she hadn’t seen him yesterday, she’d never have guessed this was a boy.
“Well,” Carol explained, “not exactly.” Mike’s secret shame exposed now to Miss Elkins, he was beet-red and his heart fluttered rapidly. “Honey, go ahead and introduce yourself properly,” his mother directed.
His face on fire with humiliation, Mike turned to face Miss Elkins. He promptly dropped into one of his well-practiced curtsies and said, “My name is Clarissa, Miss Elkins.” Then, he added, “I’m so sorry for all the trouble I’ve caused.”
Still confused, Jeannette drew in her breath a little as the nattily dressed teen curtsied sweetly. Speechless for a moment, she gawked at the sissified boy standing before her and then looked back at Carol.
At this point, Carol spoke again, “I know it’s a bit to take in. Let me explain.”
Mike stood timidly before Miss Elkins while his mother told her all about Clarissa. He cringed when she explained “petticoat punishment” and shifted his feet skittishly. At the mention of his petticoat he unconsciously swished it before he could stop himself, and Miss Elkins’ eyes grew even wider. His tummy did backflips when his mother even told Miss Elkins about his ballet lessons. It was excruciating to listen helplessly while his mother related in detail just how effeminate and prissy he had become as Clarissa.
As she spoke, Carol studied Jeannette’s expressions carefully. Slowly, the confusion on her face turned to dawning comprehension. Over the years, Carol had given this explanation a handful of times. She knew the right words to use. Given those past experiences, she soon gained the sense that Jeannette might be receptive. By the time Carol finished, she was sure she detected the beginnings of a slight smile on Jeannette’s face. “And so,” she finished, “Clarissa is here to help Michael behave better.”
“I can’t believe how feminine he… she… is,” Jeannette said at last. She hadn’t appreciated yesterday how soft and fine his features were. That other boy had been much bigger than him, but she hadn’t thought much of it considering the situation. She appraised the girlish teen with new eyes now, taking him in from those fussy French braids all the way down to his shiny Mary Janes. After a moment’s reflection, she spoke to Clarissa, “Well Clarissa, you seem to be a very sweet little girl.” She added with a slight twinkle, “You’re far too pretty to be a boy anyway, and I just love your pigtails and bows! Oh, I’ll bet you were cute as a button in your little tutu!”
“Th-Thank you very much Miss Elkins,” he said as nicely as he could manage. Mike was beyond humiliated at this point which just exacerbated the familiar stirring in his panties. He was aghast that Miss Elkins knew all about Clarissa now. When she mentioned his pigtails, he almost wished he hadn’t left his hat in the car so he could have at least covered them up somewhat.
“Clarissa has brought you something, Jeannette,” Carol prodded as she took Mike’s note from her purse and handed it to her blushing teen.
“Mother suggested that I should write you a note of apology,” he reluctantly explained.
His mother spoke next, “Clarissa, why don’t you read it to Miss Elkins? I’m sure she would appreciate that.”
Exquisitely embarrassed, Mike opened the pink envelope and began to read. He looked every bit the chastened schoolgirl in his smart uniform and darling pigtails. As he spoke, Jeannette thought he looked about twelve years old at most. She realized after a sentence or two how expressively he lilted his words. And his mannerisms were so feminine! When he was done, he refolded the note and presented it to Miss Elkins with a shaking hand. “Again I am so sorry,” he said bashfully.
Jeannette took the note and read it again as Mike continued to blush. When she got to the part about “anything else at all I can do to make amends,” an idea sprang into her head. After a brief pause, she looked up and said, “Your handwriting is lovely, Clarissa.” She then added, not unkindly, “That’s such a very sweet note, thank you.” She thought to herself that if this little angel was the same teenager she’d caught shoplifting yesterday, maybe there was something to this form of discipline.
Miss Elkins continued warmly, “Apology accepted, honey.” She smiled graciously at the ultra-girly teenager and spoke once more, “You’ve already returned the Halloween candy and other items you took… but since you offered, there is possibly something else you can help me with.” Instantly concerned, Mike tried to imagine what she had in mind and squirmed awkwardly. Meanwhile, Carol listened expectantly.
“It would all be for a good cause, of course,” she added. “You see, Clarissa,” Jeannette continued, “It’s Halloween in a few days, and I happen to need an Alice.”
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PART 5
“An… an ‘Alice’ Miss Elkins?” Mike asked uncertainly with a mix of confusion and trepidation on his face. He didn’t understand this, but it didn’t sound good.
“Yes dear, you see I’m on the board of the Belles!” Jeannette said as if that explained everything. When she saw a blank look on Carol’s face as well, she elaborated, “Oh that’s our little nickname for ourselves, Carol, the ‘Belmont Belles.’ The official name is the Belmont Ladies Civic Club. We’re a social and charity organization, and we support charitable events in the community.”
“Of course,” she added with a wink, “we do fun things too. She added jokingly, “It’s such a riot every time all us cackling ladies get together!” When Mike heard the phrase “cackling ladies,” warning bells began to ring in his head. Given his current situation, that sounded more ominous than humorous to him. Jeannette went on to explain that every year the Belles helped organize a Halloween carnival to benefit the local food bank. This year’s was being held next Saturday.
“Oh I see,” Carol said. She had vaguely heard about this ladies club but didn’t really know much about what they did.
“And that’s where Clarissa here comes in,” she said brightly. Jeanette trained her attention back on the nervous petticoated teen in the darling schoolgirl uniform. Yesterday, her first impression of Mike had been that the boy was somewhat effete, but now she saw him in an entirely new light. She thought wryly that she ought to trust her instincts more often. She continued, “Our carnival starts with a short parade, and the Belles always co-sponsor a float. This year, our float theme is ‘Famous Fictional Belles.’ We already have girls lined up to play Snow White, Cinderella, Dorothy, Pippi Longstocking, Ariel, and obviously Belle from Beauty and the Beast. Unfortunately, the young lady who was going to be Alice in Wonderland has a nasty case of the flu, and so we’ve been hunting for another Alice!” Grinning mischievously, she said, “and now it seems the perfect one has fallen right into my lap! You’re practically born for the part!”
As the other shoe dropped, Miss Elkins asked directly, “What do you say Clarissa? Will you help us out for a good cause?” With a warm grin, she waited for a reply.
Mike was horrified by the prospect of dressing up as Alice in Wonderland in such a public setting. He tried to form the words to answer Miss Elkins, but they wouldn’t come out.
When Mike failed to respond immediately, his mother shot him a look and then spoke for him, “Oh of course she will, Jeannette!” Next, she pointedly spoke to her feminized teen, “That sounds like a wonderful way for you to make up for all the trouble you’ve caused! You’ll be happy to help out Miss Elkins won’t you Clarissa?”
Trapped, Mike finally found his voice. With the matter now decided, he answered squeakily, “Oh of course Miss Elkins. I’ll be happy… to be your Alice. Th… Thank you so much!”
“Wonderful!” Jeannette exclaimed happily. “Following the parade, all the girls will help give out candy to the little ones and assist with some of the carnival games. You’ll just love it Clarissa! And that adorable little Alice costume is to die for. It will look wonderful on you!”
“That sounds perfectly fitting, Jeannette!” his mother said approvingly. “Instead of stealing candy, now she’ll give it out for a good cause,” she added. Carol was already picturing her sissified son dolled up as a delightfully girlish Alice in Wonderland.
“Speaking of fitting, that reminds me. Haverford’s Bridal is one of the other sponsors, and they already have all the costumes,” Jeannette told them. “Do you know Dolores Haverford who runs the shop?” she asked Carol.
“I’ve seen the shop in town, but I don’t believe I’ve met Dolores,” Carol answered.
“She’s another board member with the Belles, and I’m certain you’ll get along with her famously. I’ll call her right away and tell her I found our Alice!” Jeannette replied. “If you take Clarissa to her bridal shop on Monday, Dolores will furnish Clarissa all the accessories she’ll need for her costume and ensure it fits correctly. Incidentally, those patent Mary Janes she’s wearing now will be perfect.” After a moment’s reflection, she added in a lower voice, “and I’ll be sure to explain to Dolores that Clarissa is… not exactly like the other girls. I’m sure she’ll understand and handle your situation appropriately.”
“We’ll absolutely be there on Monday, Jeannette, thank you,” Carol replied. At once, she realized that another lovely lady would soon join Clarissa’s growing circle of admirers. The idea pleased her immensely even as it pained Mike to no end. Almost as an afterthought, Carol said “I also do a bit of sewing, so between Dolores and myself we’ll make sure you have a picture perfect Alice for the parade!” Mike could see his mother’s wheels spinning as she had already begun to visualize his costume.
By this point Miss Elkins was practically bubbly, and she addressed Mike again, “Congratulations Clarissa! You’re now an honorary Belle!”
With both his mother and Miss Elkins looking at him happily, Mike felt the walls closing in. Why had he tried to steal that stupid candy and cologne? This Saturday that had started horribly had only gotten worse. Still, it was shocking how fast it had devolved into utter catastrophe. Dismayed, the jittery teen stood frozen to the floor in his lovely schoolgirl uniform and gloomily contemplated his week ahead. His Halloween would truly be frightful.
“Thank you Miss Elkins,” he finally said again in a flat little voice.
With a sinking feeling, Mike knew he faced a long week filled with petticoats, dresses and lessons. On Monday, yet another new person would meet Clarissa. And then on Halloween, of course, he would become Alice in Wonderland for the carnival. As the tingling in his groin inevitably returned, he uneasily adjusted his skirt. His fluffy petticoat swished gaily in response.
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Happy Halloween!
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PART 6 - EPILOGUE
The following Saturday, Mike daintily waved his white-gloved hand to the carnival crowd as he rode atop the Belles’ float. It was Halloween, and the late afternoon sun had begun to set. The entire humiliating situation was surreal, and time seemed to stand still. Desperately hoping no one would recognize him, he did his best to smile demurely and play the part of a wide-eyed Alice in Wonderland. Self-consciously, he repeated his modest “pageant queen wave” over and over just as he had practiced earlier with the other girls. His translucent lacy white gloves only served to accentuate the exquisitely feminine gesture. Across the float, he saw Snow White giggling at him again and cringed.
As anticipated, his week had been mostly awful. When Clarissa visited during the school year, Mike was only permitted to dress in normal clothes while at school. Thankfully, Clarissa did not make appearances there. Each school morning, he would change out of his nightgown when he got up. Although ashamed to admit it—especially to himself—he had actually begun to enjoy sleeping in the frilly nighties. In fact, he had furtively “enjoyed it” almost every night this week. It was the one part about being Clarissa he secretly found himself looking forward to now. He no longer protested when his mother told him it was bedtime—no matter how early it was. He tried hard not to think about it. It bothered him greatly. Inevitably, the shame was always most intense afterward. Every time it happened, he tried to hide any evidence because he absolutely did NOT want his mother to know about THAT. This week, however, Mike had gone through an awful lot of tissue.
In any event, on school mornings his mother always laid out his school clothes and he would change when he was done in the bathroom. It was never anything he would normally pick himself, but at least it was boys clothes. Usually, it was a polo or button down shirt with a pair of slacks or khakis and dress shoes. When it was cool, sometimes she added a preppy sweater or cardigan. A few times when she had been really annoyed, he’d had to wear a bowtie. By now, when he came to school dressed like that, his friends knew he was in trouble for something and would kid him about it. Thankfully, they did not know about Clarissa.
On these days following school, Mike would return directly home and change again. He rarely had time to waste as his mother expected to see Clarissa at her desk doing homework when she got in around four. On his way home, he always grew anxious as he wondered which of Clarissa’s outfits would be laid out for him when he got to the house.
On Monday afternoon, his mother had taken him to meet Mrs. Haverford at her bridal shop. Carol had put him back in his school uniform for the occasion. She thought that would make the “right first impression.” Instead of having his hair rebraided, it was pushed back sweetly by a lovely red hairband with an attached plaid hairbow matching his jumper dress.
When Mrs. Haverford got her first look at Mike, she had complimented him on his “smart little uniform.” Knowing by now that he was “not like the other girls,” she still seemed genuinely surprised by his petite build. She said she doubted any alterations would be necessary and the costume should fit beautifully. They had followed her back to a fitting room in the rear of the shop, and he had winced when he saw it. It was even fancier and frillier than he had expected. “Gorgeous isn’t it Clarissa?” Mrs. Haverford said admiringly. Without awaiting an answer, she had ordered, “Let’s get you in it dear!”
Ruefully, Mike recalled that it was then that he had been blindsided by Mrs. Haverford. He had removed his school uniform behind a flimsy curtain partition and put on a heavily ruffled pair of white tights Mrs. Haverford had provided him for the costume. They had felt so incredibly clingy and girly that he couldn’t avoid a few tingles again. Sheepishly, he had then emerged from behind the curtain clad in his ruffled tights while his mother unzipped the Alice dress and prepared to hold it for him to step into.
At that point, he had heard Mrs. Haverford’s authoritative voice behind him. “Just a moment, Clarissa,” she directed. Quickly wrapping something around his chest, she said “you’ll need this first.” Before he even realized what she was doing, she had already begun tugging something behind his back. “Have you ever worn a corset, dear?” she asked matter-of-factly.
Caught completely off guard, the sissified teen had only managed to stammer, “A corset? Uhh… no… no… Mrs. Haverford.” Powerlessly, Mike had just stood paralyzed while she expertly cinched the laces tighter and tighter. He was startled by the sudden confining sensations as the stiff satiny garment compressed his waist and midsection. He had begun taking shallow breaths and felt a little dizzy as its unyielding panels pressed firmly in on him.
At last she seemed to finish and knotted the laces tight. “Well there you are now,” she had announced with satisfaction, “your first corset!” She went on to explain nonchalantly that several of the girls would be wearing them with their costumes. “I know it takes some getting used to, Clarissa, but you’ll get the hang of it in no time!” she added with a chuckle.
His mother had watched this transpire with twinkling eyes. “Oh my, Clarissa,” was all she said, but she was clearly intrigued.
Lightheaded, Mike had looked down at his body and was astounded. Already self-conscious about his slender build, he was dismayed to see the white satiny corset made his waist positively tiny. He had little time to absorb the shock as moments later he had been dressed in the ultra-girly Alice outfit for the first time. He felt himself blushing more as he continued his shallow breathing. Then, Mrs. Haverford and his mother had inspected the costume and discussed a few minor adjustments. “Clarissa, dear” Mrs. Haverford had pronounced in a commanding tone, “I’d say Miss Elkins was exactly right about you!” “You’re quite a lovely girl,” she continued, “and when I’m done you’ll look just like you stepped from the pages of a storybook!”
Standing stiffly in his dress, Mike replied uncomfortably, “Th.. Thank you Mrs. Haverford. That will be wonderful!” And then, despite himself, he had begun to shiver in tingly, embarrassed excitement. By the time they had departed the shop, Carol had made another new friend in Dolores Haverford. Walking to the car afterward, his mother had carried the gray garment bag with his costume, and Mike had a fancy shopping bag filled with his corset, tights, and several other girlish accessories.
Then, on Tuesday afternoon when his mother came home from work, Mike had gotten another unpleasant surprise. She had gone upstairs and returned holding the white satiny corset. “I had an idea today, Clarissa,” she announced pleasantly, “I think we should get you in your corset now so you can start getting used to it for Saturday!” She had helped him unzip the lemon yellow party dress he was wearing and then securely laced him into the confining garment. “This will help you with your posture too,” she had added brightly while zipping the flustered teen’s dress back up. To his dismay, this pattern had continued the rest of the week. Each afternoon after his mother had come in, Mike had been subjected to his unrelenting corset until bedtime. Making matters worse, he had quickly realized there was no easy way to remove it without help.
Finally, on Saturday, his mother had excitedly gotten him dressed in the full Alice costume and driven him to the carnival. Dressed so prettily and preparing to face all those people, he was absolutely on pins and needles. He had been dreading this moment all week. An icy ball formed in his tummy as his mother parked the car. His imprisoning corset only heightened the conflicting feelings and sensations.
When Mike arrived for the parade and met the other girls, he was shocked when Snow White had immediately recognized him, “Clarissa, that’s you isn’t it? We haven’t seen you in ages.” He paled when she next called out to the girl dressed as Pippi Longstocking, “Molly look, it’s Clarissa from ballet!” In response, the girl dressed as Pippi looked and then squealed with delight. To his consternation, it turned out that Molly and Mary, the twins from Mrs. Cranston’s dance class that summer, were two of the other girls on the float. At thirteen, the twins were a little younger than him and positively thrilled to catch up with their old friend. They asked if he was still taking ballet, and of course, they also knew about Clarissa’s secret. “Don’t worry, Clarissa,” Mary whispered excitedly, “we won’t tell!” They were delighted by his costume and raved about how cute he was.
“And look how teensy your waist is!” Molly observed in amazement. “Oh that’s right, it's your corset!” she realized with a chuckle. “You look just like the fairy tale!” she exclaimed giddily.
It was true. The fifteen year old made an absolutely adorable Alice! On Monday, when Mrs. Haverford had pulled out a blonde wig at the shop, his mother had insisted it would be very easy and more realistic to temporarily dye his hair blonde instead. As a result, his long, girlish hair was now a summery golden color and prettily curled in gentle waves. He desperately hoped he’d be able to get the color washed out before school on Monday. His yellow locks were held delightfully in place by a black Alice hairband with an oversize black velvet hairbow. The only good part about the hair dye was it provided him a partial disguise in case any of his schoolmates were here. Ironically, he was also thankful for the pink blush and lip gloss that gave him an extra rosy complexion since they helped the disguise too.
Mike’s enchanting blue Alice dress sported a lovely Peter Pan collar with a natty white bow. Its short puffy sleeves were elaborately trimmed in lace and gathered with elastic just off his delicate shoulders. Naturally, the devilishly restrictive corset gave him an extremely girlish figure while ensuring he maintained perfect ladylike posture. The frilly tiered skirt reaching just past his knees was generously decorated with tulle and more lace. Mrs. Haverford had fitted him with an extravagant multi-layered tulle petticoat for “maximum storybook fullness” as she put it. A crisp white pinafore apron with ruffled straps was tied snugly in a prim bow behind his back which only highlighted his minuscule waist. Of course, the clingy ruffled tights matched his pinafore and contrasted preciously with his girlish shoes. Miss Elkins had been exactly right about those. His shiny black Mary Janes went wonderfully with the rest of his outfit.
Just then, he heard his mother’s voice call him from the crowd, “Clarissa, look over here honey! Smile, Clarissa!” He saw his mother standing with Miss Elkins and Mrs. Haverford. And next, he was shocked to see that Mrs. Cranston, his ballet teacher, was with them too. Taken aback, he was disconcerted by what that might portend. He hadn’t seen her in quite some time. Meanwhile, his mother was busily snapping more pictures. Resigned, he knew those photos would soon fill several additional pages in the detailed albums that lovingly held all of Clarissa’s memories.
When Molly’s Pippi Longstocking also noticed his mother holding her camera, she caught Mike’s eye and winked at him playfully. Then, to his surprise, Molly and Mary jumped next to him on either side and put their arms around his narrow waist for some group pictures. Trembling but suddenly grateful for the moral support, he smiled weakly as they all “pageant-waved” again.
Mike moved his lips and silently mouthed the words, “My name is Clarissa.” Then, in a barely audible voice, he whispered, “I’m Clarissa.”
THE END
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Such a delightful, beautifully written tale. Thank you! Though I am always hesitant to request more from authors, Clarissa's Visit, Prequel and Halloween were so wonderful I am going to do just that. Please???
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Brilliant and beautiful.
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sissyboy1212,
When I saw this story, I wasn't aware of your Clarissa trilogy, so I went back and read them all in order. I enjoyed them all.
Your stories are well written. I can imagine myself in the Alice costume, in my voluminous petticoats and tightly hugged by my corset.
I hope that eventually you will write of further adventures of Clarissa.
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I really loved your Halloween Story of Clarissa, her pigtails, school girl uniform and especially her Alice In Wonderland costume and appearance at the charity event and parade. Thank you.
JaimieS
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Thank you all for the lovely feedback. I’m very glad you enjoyed my little story. I imagine Clarissa will need another visit at some point but not immediately.
Hugs to all that read and commented.