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From Locker Room to Lingerie - Final Part 1
🕑 Added 2025-03-20 14:34:13 +0000 UTCNOTE - If forced feminization offends you, please refrain from reading or listening to this story. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions.
Reader discretion is advised. Enjoy responsibly within the context of fantasy.
Ms. Smith quickly seized Billy's arm and angrily pulled him to her.
"You listen to me! If you want to stay out of prison, you'll do exactly what I say. I thought I'd made that abundantly clear.
If Rachel and I want to see you waltzing down the runway in a pretty dress, then that's just what you'll do! Now, you owe Ms. Gladstone an apology," his mother hissed. Ms. Smith swatted the boy's pantied and girdled bottom.
"I, I'm sorry, Ms. Gladstone. I'd love to be in your fashion show."
Billy stole a glance at his mother and saw that she was still angry at his outburst. "Apology accepted, dearie. I just know that you'll be the talk of the show." Billy could well imagine. "Although your little tantrum reminds me that your feminine comportment could use a lot of work. If you're going to wear darling clothes, your mannerisms should match, don't you think?"
"Why Ms. Gladstone, what a wonderful idea. If Billy insists on wearing pretty things, I don't want him slumping around like some, boy!"
The women all laughed at Ms. Smith's joke.
"Luckily, I know just the person who can help. Ms. Tuttle is a friend of mine who conducts charm classes for girls. I'm sure that she will be able to bring out the 'girl' in your son in no time!
I'll simply give her a call to explain that she'll soon have a new student."
Ms. Gladstone thought cruelly that Ms. Tuttle would give Billy exactly what he deserved, particularly if she called with some 'special instructions.'
"I must warn you though, that Ms. Tuttle is very strict with her girls. But she does get results! I'm sure Billy will just love being a 'Tuttle girl'."
Of course, Ms. Gladstone's suggestion amused Billy's mother and sister to no end, and once again, Billy was made to thank Ms. Gladstone for her "kind offer."
Taking the card offered by Ms. Gladstone, Billy's mother promised to call her that afternoon. Finally, the trio was ready to leave the store.
Each of the three was laden with several large pink shopping bags containing Billy's new wardrobe.
As they approached the entrance to the store, Billy stiffened up as he realized that he was about to leave the relative safety of the store.
He trembled at the thought. Recalling his sissified image in the dressing room mirror, Billy shuddered at the thought of anyone seeing him dressed as he was. Instinctively, he stopped in his tracks. In the end, ignoring his tearful protests, Ms. Smith and her daughter simply took Billy's arms and forced him out of the store.
As they led Billy to a small cafe for lunch, Ms. Smith and Rachel snickered at the teasing comments and incredulous looks directed at the feminized boy.
During lunch, Rachel realized that she was having so much fun that she didn't want the shopping expedition to end.
Billy, who couldn't get home fast enough, listened in abject terror as he heard his sister enthuse, "You know, mother, when I turned 13, you started letting me wear makeup. I think that it's only fair that you let Sissy do the same."
Ms. Smith, who was thinking of a way to make Billy pay for his outburst at La Femme, readily agreed.
"What a coincidence! I was thinking the same thing. Let me give Ms. Gladstone a call to see what she thinks. She has the most wonderful ideas!" Billy sat quietly as his mother dialed the store's number on her cellular phone.
Billy hoped against hope that Ms. Gladstone would veto the idea. Billy listened as he heard his mother's side of the conversation:
"Hello, Ms. Gladstone? This is Sarah Smith, Yes, Billy's mother.
We were just having a delightful lunch when Billy insisted that he be allowed to wear makeup.
I know, I would think that he would be embarrassed enough to appear in public dressed as he is, but you know Sissy!
You do, I see I think that's a marvelous idea, and I know Sissy will too. Bye-bye." Billy waited anxiously as his mother reported the details of the conversation.
"Well, darling, Ms. Gladstone simply couldn't get over how quickly our little girl is growing up! She had some marvelous ideas about your makeup, and I can't wait to see the results. Let's go."
Billy tossed the shopping bags on his bed. His mind had gone numb. Without a doubt, he had just endured the most embarrassing and humiliating day in his life. As he sat on his bed, he caught his reflection in the mirror on the back of his closet door. He was still wearing his "pretty in pink" outfit, but that's not what drew his attention.
It was the heavy mask of makeup that the salesperson had laughingly applied under the direction of his mother and sister.
As Billy sat at the cosmetic counter in a busy department store, Ms. Smith had explained that her son had begged them to allow him to use makeup and that he was so precious, that they simply couldn't refuse him.
As Rachel whispered instructions to the giggling salesgirl, Ms. Smith had directed her attention to Billy, who was not allowed to see what the woman was doing to his face.
"Sissy, Ms. Gladstone agreed that you were ready for makeup. Most girls your age use a little makeup-maybe some lip-gloss and some mascara. The idea is to look pretty, but natural.
But since you're only a pretend girl, Ms. Gladstone suggested something a little more obvious, something dramatic.
Something that screams, 'I'm a sissy!' With that, Ms. Smith wheeled Billy around to face a mirror on the counter. Billy gasped with horror.
He looked like pictures he had seen of actresses from the fifties heavy foundation, exaggerated blush, false eyelashes, and the finishing touch, a Cupid's bow of bright red lipstick that matched his fingernails.
Transfixed by the horrible image, Billy barely noticed as the sales girl placed all of the products Billy would need to reproduce his "look," as well as a moisturizing mask, in a large bag. Laughingly, the pretty sales girl had added, "We're having a special today.
With each purchase, you get a free fragrance gift. I've picked one out how especially for you.
Here, let me try it on you.
Don't you love it? It's called Pansy!" Wearing his new "look," his mother and sister had insisted on dragging him to every girl's clothing store in the mall.
As a sample of what Billy had to look forward to, the two women picked dress after dress for Billy to hold in front of himself as he was forced to view his girlish image in the mirror. Billy thought ruefully, the mall should pay him for serving as entertainment for all the customers.
Billy was lost in thought of as the door to his bedroom slowly opened. Suddenly, in a burst Rachel and a group of her friends.
"I don't believe it! Look at him? Isn't he the most ridiculous thing you ever saw?"
"Look at that makeup! He looks like he's ready for the theater!"
One of the girls shrieked as she started pulling things out of the shopping bags. "Oh my gosh! How precious! No way your brother wears this stuff!"
"Way!"
"How in the world did you make him do it?"
"Oh, that's the best part. Sissy dearest picked out all these lovely things himself!
He's such a girl!"
Ms. Smith watched with satisfaction as Rachel and her friends made Billy try on his new outfits.
Ordinarily, she would have asked the girls to tone down the shrieks and the squeals, but she decided to let them have their fun.
After all, Billy had were ruined many of Rachel's slumber parties and had generally bothered the girls when they came to visit showing off and playing practical jokes.
Besides, she was really enjoying hearing the girls make suggestions to improve Sissy's appearance and their teasing comments.
Ms. Smith invited all the girls to stay for dinner, and the girls watched in amazement as Billy donned his apron and did the dishes. His periodic tears all only served to encourage the girls.
Of course, the girls insisted on staying and "helping" Billy with his beauty regimen and did not leave until he was dressed in his nighty and his face was encased in the moisturizing mask.
Ms. Smith and Rachel assured them that they could stop by anytime and "play" with their former tormentor. As Billy lay in bed Monday night, idly fingering the bow on his nighty, he reflected on the day's events.
Before going to school that day, Billy had seriously thought that any day, he would be able to go back to his old life.
He kept expecting Ms. Walker to tell him that she thought he had learned his lesson and he could resume life as a boy.
Billy knew that there'd be some kidding about his eyebrows and the bra and panty stuff, but he knew that he could make up some lie that would appease his buddies. He thought that he could rejoin the team, having only missed a couple of games.
He'd probably even get his old starting position back. More importantly, Billy had even started to plan how he was going to make Rachel pay for the stuff she had done to him. And that Ms. Gladstone!
After he found out where she lived, he and his buddies were going to have some serious fun trashing her house! After that Monday, though, Billy no longer harbored such illusions.
Rachel had wakened him earlier than usual that morning, explaining that he would need extra time to put on his "face."
Billy had assumed that the makeup was a one-time punishment. He couldn't believe his mother and sister were going to force him to wear it to school. He had shouted some choice obscenities at his younger sister until his mother intervened and warned Billy about the price of disobeying Rachel. After Ms. Smith left the room, Rachel had pinched Billy's ear - hard - to let him know that she was in control for a change.
Rachel had lain awake the previous night too, recalling the innumerable times Billy had embarrassed her, made her cry, or teased her about some aspect of being a teenage girl from her period to her choice in boyfriends. She had been powerless to stop it.
During the night she had decided that no matter what it took, she was not going to let her brother "go back" to his old self.
With a sneer on her face, Rachel had started in on her brother, who had never seen her so angry.
"Now, you little pansy, watch carefully. I'm going to do your makeup this morning, but tomorrow you're going to start doing it yourself.
Mother and I decided that it would be best if you never left the house without your makeup on."
Seeing the hate in his sister's eyes, Billy gave up trying to intimidate her and started pleading with his sister not to make him up. He began promising things that he'd do all her chores, that he'd never bother her again, that he'd let her have his CD collection.
Anything. Rachel loved hearing her older brother beg and promised herself that she'd hear more in the future.
She had simply laughed derisively. In the end, Billy's face looked like it had at the department store perhaps worse. After dragging her brother in front of his mirror so "he could see how pretty he looked," she shoved her bra and panty choice at her brother.
After watching with a satisfied smirk as her brother dejectedly donned the girdle, bra, and panties, she had sighed disgustedly and roughly adjusted his the flesh in his bra so that his boobs were bigger. Rachel opened Billy's closet, a broad smile on her face. "What a lucky little girl you are, Billy, to have so many cute things!"
Finally, Ms. Smith entered the room, and she and Rachel had an animated discussion about what Sissy should wear on his first day of being fully "out." Billy had hoped that the two would relent and let him wear his old clothes. However, Rachel and his mother dismissed his protests.
"Now dear," his mother said, "you're starting a new life today, and Rachel and I think you should wear something that makes a 'statement.' Something like this!"
As Ms. Smith turned from the closet, Billy saw that he she was holding pink stretch pants and a sheer white sleeveless blouse with enormous ruffles down the front.
Rachel hummed to herself as she added pink pumps with low spike heels, gloves, and a big bow for Billy's boyish hair.
Realizing that trying to reason with his sister was useless, Billy quietly begged his mother not to make him go to school dressed as he was.
Ms. Smith responded with a curt, "You picked it out and insisted on buying it, so you're going to wear it!" After he was dressed, Rachel snapped countless pictures of Billy's "coming out" outfit.
When the time came for Billy to walk to school, Rachel and Ms. Smith literally had to push Billy out the door.
As they did so, Billy's mother shoved a pink purse over his arm, explaining that a girl like him should never be without his purse.
"Besides, you'll need to freshen your makeup during the day. Ta-ta!" Underneath the mask of makeup, Billy's face burned red-hot with shame as he saw the incredulous looks on the other students' faces and endured the taunts of his classmates. It was all he could do to keep from crying.
It was all Cindy Jackson's fault, he thought bitterly. He tried to hurry to the relative safety of Ms. Walker's office, but the unfamiliar high heels impeded his progress. The faster he tried to walk, the more wildly his hips wiggled in the damn things!
When he finally reached Ms. Walker's office, he quickly slammed the door behind him as if to shut out the world. He soon realized that it didn't make any difference, as Ms. Walker forced him to recount the weekend's events. When Billy could take it no more, he cried, "Please Ms. Walker! Don't make me do this anymore. I look like some kind of drag queen!
All the kids will think that I want to look like this!"
"But Billy, you do! You could have taken your punishment like a man, but you took the sissy way out. Unconsciously, you wanted your mother and sister to do this!" Billy's protests grew weaker as Ms. Walker's psychological double-talk confused him more and more.
Billy knew further denials were useless, and he sat slumped in his chair. He listened as Ms. Walker called the principal to inform her that she was providing therapy to Billy and that his attire for the remainder of the school year would be somewhat "unusual."
The principal had assured Ms. Walker that the school's diversity policy would protect Billy from any physical harm and that he should wear whatever he felt was indicated by this therapy. The principal told Ms. Walker that she would inform all the teachers and that she would be happy to assist Billy's therapy in any way possible.
"Great!" thought Billy. As Ms. Walker pushed Billy toward the door, she handed him a school registration card.
"I think it's time that you started taking classes that will prepare you for your new future. Don't you?" Billy glanced at the card and quickly saw that his college prep courses had been replaced with Home Economics and secretarial classes. Relishing in the crushed look on Billy's face, Ms. Walker whispered in his ear, "Won't you look sweet on some hunky executive's lap taking dictation in a short skirt and darling sweater set."
Later that day, Billy's mother picked him up from school to drive him to Ms. Tuttle's charm school.
As they waited in the well-appointed lobby, a large group of girls slightly younger than Billy filed out. Billy wished he could die as they saw him in his sissy attire and began to titter.
Soon, a large immaculately dressed woman approached Billy and his mother. After Ms. Tuttle introduced herself, Ms. Smith started explaining about Billy and his "special" situation. Ms. Tuttle interrupted: "I know all about Billy, or should I say, Sissy. Ms. Gladstone and I had a delightful conversation."
Ms. Tuttle went on to recommend that Billy come to her establishment every afternoon for a month. After that, she explained, only an occasional refresher class would be necessary.
She also encouraged Ms. Smith to watch the sessions so that she could see firsthand the behavior and mannerisms they had "corrected." That way, if she saw any return to old ways, she could report the deficiencies to Ms. Tuttle for "appropriate action."
After situating Ms. Smith in a comfortable love seat on the perimeter of the room, Ms. Tuttle led Billy to a chair in the room's center. She glared at Billy with a mixture of amusement and disgust. Billy slumped in his chair as he heard her explain that in her normal charm classes, she developed behavior and manners that would help young girls succeed in the business world if they elected to pursue a career. "In your case, however, I intend to make you the swishiest, girliest, model of exaggerated femininity that anyone has ever seen!"
Panicking, Billy glanced at his mother only to see that she was nodding her eager assent to Ms. Tuttle's plans.
"Now, for our first lesson, we're going to learn to sit like a little lady."
Billy slumped down in his chair. Who did this woman think she was. He might have to look like Doris Day on estrogen, but they weren't going to make him act like some queer. Billy had been a football player.
What did this woman think she was going to do to him? When Ms. Tuttle instructed him to sit up tall, back arched, to show the world his "pretty little boobies," Billy simply ignored her. As she repeated her instructions, Billy could sense that she was losing patience with him.
Finally, Ms. Tuttle said, "Okay, Billy, we can do this the easy way, or we can do it the hard way. Actually, in your case, I think that I would prefer the hard way. Now which is it?" Billy continued to slump in his chair sullenly and smugly.
Without warning, Ms. Tuttle quickly reached down and grabbed Billy's upper arm. She snatched him out of the chair with such ease that Billy immediately started to panic. Easily dragging the struggling boy to her desk, Ms. Tuttle seized a riding crop from a drawer. In no time, she had tattooed Billy's bottom with six short strokes. Billy cried loudly, more out of surprise and shame at being so easily handled by the woman than from pain. "Well, Sissy. Do you want some more?" "No!" he cried.
"Do you mean 'No thank you, Ms. Tuttle?'"
"No thank you, Ms. Tuttle!" From her vantage point, Ms. Smith watched on in amazement. She thought back to all the times Billy had reduced her to tears over her inability to control his behavior. Now, apparently, the shoe was on the other foot.
Soon, following Ms. Tuttle's instructions and commands, he was sitting with his legs crossed at the knee, toes pointed, back arched prettily, with his hands prissily folded in his lap.
At Ms.Tuttle's command, a simpering "sissy smile" was on his face.
His mother's giggles of delight told him all he needed to know about how he looked.
However, the ever-present riding crop prevented him from doing anything other than what Ms. Tuttle instructed. Ms Tuttle also gave him a lesson on walking like a little lady: hips rotating in an exaggerated fashion, mincing little steps, elbows bent, and hands above the waist at all times, with his purse either over his elbow or in his hand.
Every hesitation or mistake on Billy's part earned him a sharp blow from the riding crop, which fell with a large THWACK!
Finally, it was time to go home. After Ms. Tuttle admonished Billy's mother to watch him carefully to see that he did not forget the day's lesson, mother and son left the establishment. Once outside the door, Billy let out a huge sigh of relief and began walking in his normal boyish fashion.
Observing her son, Ms. Smith rebuked him sharply, "What do you think you're doing, Miss Prissy? Didn't you just learn how to walk in a manner befitting your personality?"
"Mom! You can't be serious! That woman's nuts. I'm not going to walk like that! I'll look like a complete fool."
"You can and you will, you fairy! You'll follow Ms. Tuttle's lessons exactly! Or do you want me to report tomorrow that you've been a bad girl?
I don't think Ms. Tuttle likes you very much, and I'll just bet that riding crop stings!"
Billy had hoped that once his mother had seen the ridiculous way Ms. Tuttle was making him a move and act, she would reconsider.
Obviously, he was wrong. Knowing instinctively that his mother's threats about Ms. Tuttle and the riding crop were accurate, Billy had no choice.
Tears welled in his eyes, and he began to mince his way to the car, as instructed by Ms. Tuttle. Ms. Smith couldn't help but grin as she offered "constructive" criticism.
"That's it, girly! Take smaller steps. Remember to wiggle that big bottom. Arch that back more you act like you're ashamed of your darling breasts.
Keep those elbows and wrists bent." Rachel was delighted in the "improvement" in Sissy, and had him practice all night long.
Rachel and her mother agreed that they had never seen a real girl who moved in such an exaggeratedly feminine fashion.
Billy was mortified when he heard his sister declare him more prissy than Margaret Johnson, the most fastidiously girlish female in school. Inwardly, Billy knew she was right.
In the days that followed, Ms. Tuttle "corrected" every masculine movement and mannerism that Billy had. She didn't stop there, however. She soon had Billy talking in a girlish lisp and had altered his vocabulary to match.
Billy's formerly boisterous laughter had become a high-pitched giggle, and no matter what his true emotions, he always wore a simpering "sissy smile."
It was Ms. Tuttle who "convinced" Billy that the sissy in him should be enthusiastic about everything he did, especially if it was suggested by his mother or sister. After all, they knew what was best for him, didn't they?
Rachel and her mother were wildly entertained by the changes in Billy. The sight of him swishing around the house never failed to produce laughter on their part.
Of course, this just made Billy feel worse.
To add to his humiliation, Rachel made Billy practice in front of the large mirror in her mother's room, knowing full well that having to view himself acting and moving as he was completely devastated him. Rachel had also talked Ms. Smith into getting a riding crop like Ms. Tuttle's, which she wielded with great abandon.
Any perceived slight on Billy's part resulted in stinging blows from his sister forgetting to cross his legs, not putting his make-up on heavily enough, mistakes in his crocheting and knitting.
Of course, the fact that it was his younger sister delivering the blows made them sting even more.
One "charm class" held particular significance for Billy and his family. From her seat Ms Smith could see that after a particular remark by Ms. Tuttle, Billy had reverted to his normal voice and was starting to argue with her. Ms. Tuttle had simply seized Billy's arm and whispered something to him.
As she was talking, Billy's face went white with fear. Ms. Smith could never get to Billy to reveal what Ms. Tuttle had said, but it had the desired effect. Billy slowly minced over to where his mother and sister were sitting, enjoying the "show."
"Oh, Mommy dearest, Ms. Tuttle says she has some special pills to help me be prettier. She says they'll make my little boobies grow bigger and make my hips more girlish!
Wouldn't that be simply divine? May I take them please?" Although her son's breathless voice was asking her to say yes, his eyes were pleading with her to say no. Ms. Smith and Rachel exchanged smirks as Billy's mother decided to have some " fun" with her son.
"Frankly, Sissy, Rachel, and I have been expecting this. After all, we both knew that it wouldn't be long before you would want to do everything possible to feminize your body. But I don't know, it's such a drastic step. Are you sure you want to have girlish hips and large breasts? After all, there will surely be no going back to being a regular boy," she said with pretend concern.
Ms. Smith could feel the resentment coming from her son as she forced him to beg him for his worst nightmare. Billy quickly became sullen, but as Mr. Tuttle took a few steps toward them, he quickly assured, "Oh yes, Mommy!
I want to look as feminine as possible, and Ms. Tuttle says these pills are just what I need. Please?"
Ms. Smith smiled as her son's already girlish voice rose half an octave at the approach of Ms. Tuttle. "Well, Sissy, I must confess to being a little shocked.
After all, those times you insisted that you weren't a sissy ... and now this! But who are we to stand between you and your true desires!" As Billy jumped up and down and clapped his hands in apparent girlish glee, Ms. Smith saw a tear run down his cheek. On the drive home, Rachel couldn't help but stare at her older brother. She was imagining him with large breasts and hips.
A few weeks ago, she would have never imagined that she would have in her hands several large bottles of estrogen tablets for him. The fact that her brother had been made to beg for them made them even more precious.
At supper that night, Rachel had insisted that her brother start taking the pills immediately and happily held one out for him.
To her surprise, Billy had actually slapped her hand and knocked the pill out of it. After recovering from her shock, Rachel whispered in her mother's ear. Soon, Ms. Smith had Billy's arms pinned behind him, while Rachel held his nose to force him to open his mouth.
"Well, brother dear! Since you seem to have had a change of heart, we'll just have to help you on the road to womanhood."
Instead of the one pill that she had offered Billy earlier, Rachel popped three pills into his mouth.
This scene was repeated over the next several days until Billy quickly realized that his resistance was only speeding up his physical feminization.
After that, he reluctantly took his "medicine," with his sister happily double-checking to ensure that Billy had swallowed the pill.
After that, Rachel delighted in making her brother strip down to his panties in front of the large mirror in her mother's room.
She would then carefully examine her brother's breasts for signs of growth. To further humiliate her brother, she had taken one of her mother's "C" cup bras and put it on him.
After stuffing the cups with tissue, she had made him try on several of his mother's sweaters and clingy dresses, just to get an idea of what he was going to look like in a few months. "Just think," Rachel mocked, "there's a good chance you'll be even bigger than Mom!"
Comments
Brett Schuhkraft
His only hope now is to embrace the change or he’s going end up broken permanently But on a serious note every boy should spend a couple of years as a girl to understand how it feels to be objectified and made to feel inferior Maybe the world would be a better place
Amanda
Loving the quickening transition in this Story.🫠❤️💁♀️
My Freeze
The laddie is on her way to becoming feminine. Such is life, have fun and enjoy the ride. Really enjoyed this chapter.
