By Pink Bra
By Pink Bra
Chapter 1 - Gustav's Troubles
Meet Gustav: An Average looking high school senior -
Gustav walked into his level four biology class and sat next to Charlie, a friend from a grade below who he had met in the weeks since school began. Gustav was a slight, average looking eighteen year old young man and on the verge of finishing high school. While his grades were good, they fell way below what his mother expected. As Gustav sat down next to Charlie, one could tell these two boys were not the exactly the most popular kids in school.
For reference, here is a picture of Charlie:
"Given any thought to the school Halloween party, Gus," asked Charlie, who was interested in winning the five hundred dollar prize for best costume.
"Not really," sighed Gustav, who was more worried about his grades than a silly Halloween costume contest.
"There are more important things than money and holidays, Charlie - like our grades! Class is about to start, we better shut-up before Mr. Douglas starts giving out detentions."
"Sure, whatever, Gus, but you know it'd be sweet to have that kind of money," said Charlie in opposition as he opened his books, ready for class.
Gustav and Charlie had decided to spend some time together to study after school. Midterm reports were going to come in soon, and Gustav wanted to make sure his grades were as good as possible. The boys met up in front of the school and decided to walk to Gustav's house because it was closer and Charlie had not been getting along with his mother at all lately, who had taken to drinking heavily ever since his father died three years ago.
As they entered Gustav's house, Gustav's mother, a beautiful middle aged woman walked in from the kitchen to greet them.
"Nice to see you again, Charlie - you boys plan to study, I hope? I do know that your midterms are coming up very soon," said Gustav's mother in a firm, but approachable manner, "and I'd hate to see you two nice boys do poorly."
"We'll be fine, mom - we're going to go use the den, if you don't mind."
"Of course not, Gustav, just make sure not to make a mess of it, I just had it cleaned."
"Yeah, yeah," said Gustav.
As the boys walked to the den, Charlie's mother, a woman by the name of Sophie Spencer walked back to her laptop on the kitchen table. As she continued research into the best university choices for Gustav, she couldn't help but worry about him. She knew he was working hard but his grades, in her eyes, remained mediocre at best. Sophie, a successful doctor at the local university, scanned the various top tier college websites where she wanted her son to go. As she browed the page of her alma mater, the University of Westlake, she recalled how Gustav could never attend this particular school. Though she had done well for herself in her life and donated to the school generously (even having a building named after her), it was one of the rare girls-only universities remaining in the world. Otherwise, Gustav could have easily been admitted under the alumni-legacy program.
"I don't think Gustav would be up for it," she joked quietly, "besides, what are the odds of that ever - ," stopping herself, thinking the possibility preposterous. As Sophie continued to scan other schools, she thought about how worried for Gustav she had been recently. She knew that he was trying his best, but the pressure was really getting to him and he seemed depressed and edgy. Sophie couldn't let up on him though - she needed to be strict for his sake and for his future. Sophie wanted Gustav to be a doctor as well and continue a new family tradition. She hoped that her grandchildren could be doctors one day as well. Sophie continued to research with that happy thought in place.
Gustav and Charlie had been studying for over and hour and decided to take a break. As Charlie stood up to stretch out his legs, he walked around and noticed an open door to a smaller room.
"What's all this?" Charlie said as he entered the small room. Gustav walked in behind him and reached for the light switch, flicking it on.
"It's my mom's trophy room. Well, it's our trophy room, but it's mostly her stuff. She leads a pretty interesting life as you can see!"
"Tell me about it," said Charlie as he scanned the photos, plaques, and other memorabilia, "your mom won the state beauty pageant?"
"Yeah, pretty neat, eh?" said Charlie as he pointed at the gown hung up on the mannequin bust - "This was the dress she wore when she won it."
Charlie looked at all the pictures of Gustav's mother and was in awe. Gustav's mother, Sophie, had lived a very interesting life before she had a child. Sophie was so beautiful in her youth that she had won pageants, modeled, and traveled the world. Charlie even admired the photo of her working as a Bunny in one of the Playboy clubs.
Even though it might seem strange to display such a picture, Sophie would often remind Gustav that the work she obtained through her beauty was what paid for medical school and it was nothing to be ashamed of - and that is exactly what Gustav explained to Charlie. Other photos depicted Sophie as a stewardess and even a lingerie model.
Gustav would also use this room to remind himself that his mother was a remarkable woman, and though she may be harsh at times, she was only so because she cared for him. He only wished she would pay more attention to his needs as her son.
"Wow, your mom's so cool! Look, a picture with Mick Jagger!? Man, I wish I could be like your mom - all cool and stuff!" said Charlie as he gushed over the memorabilia.
"We should get back to studying, Charlie - damned test is coming up and before we know it, we'll fail it miserably."
"Relax, relax, I just wanted a quick break," said Charlie as the boys exited the room.
A few hours later Gustav was seeing Charlie out as Sophie came into the foyer to wish Charlie a good night. Gustav was carrying his clipboard in his right hand as the Halloween flyer slid out and slid to Sophie's heels. Sophie picked it up and quickly scanned it.
"Gustav, are you planning to enter this contest?"
"No, mom, that Charlie's flyer - he wants to win that contest. Don't worry about me! I'm going to be studying that night!"
"Nonsense, Gustav," said Sophie, "you should enter the contest. After all, you've been working to hard lately. In fact, I want you to do this and I want no arguments."
"But - ! Sure, whatever," said Gustav submissively. Spending a lifetime with his domineering mother, he was trained not to argue with her. He would submit himself and go along.
"Well, it looks like I have another friend to go with then," said Charlie triumphantly, "Now, all I need to do is come up with a prize winning costume!"
"Do you have any ideas?" asked Sophie.
"None yet, Ms. Spencer, but I still have a week."
"Time is running short, Charlie, but I wish you the best of luck!"
"Thanks, Ms. Spencer!" Said Charlie
"Man, what have you got me into, mom?" sighed Gustav.
"Pish-pash, Gustav, this will be good for you, sweetie," said Sophie as she placed her left hand on his shoulder.
"I hope you come up with a good idea, Gustav - one of us has to win that prize money!" said Charlie.
"Don't you worry about Gustav, Charlie - I'm sure his costume will blow you away!"
Charlie left Gustav's house knowing that Sophie, a certified winner and a doctor, would come up with a great idea. He would have to keep up if he wanted to compete. As Gustav watched Charlie walk down their driveway from the large windows in the foyer. As he did so, Sophie removed her hand from her shoulder and took a slightly more strict tone.
"Now, I want you to study for another hour and then dinner, alright? We'll work on your costume tomorrow after I get back from the hospital - I'll need to get a few supplies," stated Sophie.
'What do you have in mind?"
"Something I feel would suit you, dear - you'll have to trust me on this one."
On one hand, Gustav was kind of worried what dumb idea his mother might come up with, but on the other, it was an opportunity to spend some time with his mother - a rare opportunity indeed.
After dinner that night, Sophie made sure to grab Gustav's measurements. Gustav knew better than to protest the act and he stood quietly as she measured his bust, waist and hips. He just figured it was for the no-doubt stupid costume she would have him wear.
The next day, Gustav arrived home to find his mother busily preparing his costume in the lounge of their large home.
"Before we get you dressed, we need to prepare you, honey," said Sophie as she rushed to the door and lead Gustav up the stairs.
"Honey? What's that over there? Looks like a dress or something!"
"Don't question your mother, Gustav," said Sophie sharply.
"That's better, now take off your clothes."
"All of them?"
"It's nothing I haven't seen before, Gustav - now, if we are going to make this costume work, you must do as I say and stop asking questions. Now stop being difficult!"
"But - "
"Quiet, now take off those clothes!"
Gustav, in constant fear of reprisal from his demanding mother, immediately stopped asking questions and removed his clothes.
"Now, I need you to put this one. Here, I'll help you into it - it has a zip and clasp in the back," said Sophie as she approached a naked Gustav holding a pink all-in-one support undergarment.
"M-mom, that looks like a woman's underwear."
"Of course, dear, you are going as a girl for Halloween - and before you open your mouth, you know what I'll do if you give me any trouble! Now step into the briefer - I'm sure you can figure it out."
Gustav had that sinking feeling as he grabbed the extremely feminine underwear from his mother and stepped into the leg holes. He didn't like the idea of going outside dressed as a girl - especially in front of his school mates - but the idea of contradicting his mother was even worse. As he slid the lingerie up his body and wrestled with the straps, his mother zipped and clasped the back.
"As you can see, Gustav, it controls the crotch area, smoothing it out, and cinches in the waist. It is the beginning of a decent approximation of womanhood!"
"Now, I want you to sit down and relax for a moment while I grab some falsies for you."
"F-falsies - you mean fake breasts?"
"Please, Gustav, it's all a part of the costume - now shut-up!"
"Sorry," said Gustav as he looked down at the empty cups of his underwear.
Sophie returned moments later with a pair of false breasts which she quickly slid into Gustav's cups.
"How do you feel, Gustav?"
"Well, I guess it's not that bad," sighed Gustav.
"Good, things are always easier when you play along, dear. Besides, lots of young men go as woman for Halloween. I can see it - I bet you'll win. Spencers always win. Don't you like winning?"
"I-I guess I do," said Gustav as he caught a glimpse of his feminized form in the mirror. He looked like a boy with big fake boobs but he trusted his mother.
"Good, Gustav. Now, let's go to my vanity and finish up. I'm glad you finally relaxed," said Sophie with a pat on the shoulder and a warm, rare smile. She even gave him a little peck on the head. Sophie was suddenly having an unprecedented streak of motherly warmth.
Gustav and Sophie walked up to Sophie's bedroom and as Gustav walked into his mother's bedroom, he admired the serene quality of her environment. His mother instructed him to sit in front of the mirror on the padded stool as she went back downstairs to grab a few items she forgot to bring up.
"I'll be right back so just relax, alright," said Sophie as she minced out of the room.
Gustav couldn't remember the last time his mother had become so suddenly pleasant. As he stared in the reflection of himself in the mirror, his eyes glanced to all the feminine accessories on the counter.
"When in Rome," Gustav said to himself. He decided then and there to have a little fun as he vamped for the mirror. He crossed his legs, squeezed his big fake falsies together and grabbed a large make-up brush. As he was messing about, his mother walked slowly into the room and observed Gustav without being noticed. Sophie was desperate to get Gustav into a good school, and being a doctor, she had seen transsexuals in the past. If Gustav went to Westlake, it would solve all of her worries. She wondered if Gustav was really born to be a woman at times. She always observed how frail and feminine he was. That is why she decided to dress him up as a girl. Though it was a ruse, it was also a womanly litmus test. She had to know if she had the option. It would be best for Gustav.
"Maybe, he could take after his mother. Maybe he could be a woman. It wouldn't be so bad for him," whispered Sophie to herself.
Chapter 2 - Charlie's Fun
"God, I'm so sick of high-school, Stacey. I can't wait to graduate and get the hell out of this town," said Charlie as he sat on the edge of his bed.
"I hear you, Char, I hear you! What do you want to do tonight, by the way?" said Stacey as she toyed around in Charlie's closet.
"I figure we could just go to the mall and hang out."
"Which mall? The mall out of town, or the mall here? Oh - when did you get these shoes?"
"I got those heels over the internet, aren't they fabulous? They're going to look great with my new skirt. We're going to the mall out of town tonight, Stacey," said Charlie with a hint of danger in his eyes.
"Awesome - but aren't you afraid people are going to recognize you, Charlie? I know I encourage you but I worry what would happen if you get caught."
"You know I'm hot, bitch - no one would recognize me. Besides, the hormones are really starting to kick in. My ass is getting bigger and my breasts are finally starting to be - you know - breasts," said Charlie as he undressed and undid the bandage around the chest, letting his pert, small breasts jiggle in the cold air.
Charlie was becoming a woman!!
"You're like a totally different person in your 'girl-persona'! Aren't you afraid your grandma is going to see you smuggling those little balloons around the house?"
"Have you seen granny, lately? She's as blind as a bad these days - her eyesight is almost completely gone now - not like it was any good for the last 5 years. The only person that could see me would be granny's nurse and I know exactly when she comes and when she leaves."
"Gotcha, hun - c'mon get dressed so we can get out of this house. It smells like mothballs."
As Charlie went to the closet, he let out a big sigh.
"What's wrong?" asked Stacey.
"I'm just getting sick of the charade - I'm going to run away one of these days, Stace, and just go to the big city and become a waitress or something. I need to be a woman and every day, the feeling gets more intense."
"Don't leave me so soon, hun. Who am I going to borrow clothes from? You've become quite the clothes horse lately."
"I'm serious. I can't do it anymore. I even have a crush on a boy now! Remember when we were dating? Everything is so upside down."
"Yeah, I remember when we were dating - I feel kind of bad for starting you on your first bra and panty set! Who do you have a crush on? That dorky Gustav kid you're always hanging out with?"
"Maybe - maybe if I dress up as a girl for Halloween, he'll notice how beautiful I am."
"I thought you were going to dress up as a girl anyways - I told you that you would look so good, you'd be a shoe in for the prize money."
"Yeah I was thinking about it, but what if people, you know, find out?"
"They won't - it's Halloween! C'mon, get dressed and let's get out of here."
Charlie chose an outfit any normal girl his age would wear and laid it out on his bead. He chose a pink set of bra and panties, put them on and sat in front of his vanity and did his hair and makeup.
He finished by putting on the casual skirt and top and slipping on his shoes. He was indistinguishable from any other girl.
Charlie decided he would buy a pretty dress tonight and use it to get Gustav to see him for who he truly is...
Chapter 3 - The Pretty Gustav
Gustav heard the whispers and suddenly turned to discover his mother.
"Did you get what you needed?" he asked as he quickly uncrossed his legs.
"Yes, dear," said Sophie as she put a box down on her desk. "Now, I want to put some makeup on you, Gustav. So sit perfectly still while I apply it for you."
Gustav watched as Sophie slowly transformed his face into that of a young woman's. Gustav continued to be in shock of how he looked. He thought he was looking just like a regular girl now. He had to wave at his own mirror reflection to make sure his eyes were not playing tricks on him.
"Now, we will add a nice wig to complete the effect of femininity," said Sophie as she reached for the box and grabbed a red wig. Sophie secured the beautiful, full wig on Gustav's head. When she finished, they were both a little surprised. None of them were prepared for how convincing the effect would be.
Sophie was so happy for how Gustav looked, that she began to tear up a little. She broke the silence and maintained her composure though.
"Now, I have a nice pair of stockings, shoes and a dress for you as well."
"O-Okay," said Gustav nervously. He wasn't sure if it was right to feel this good with all of these girls clothes on - but he had to be sure. He wanted to complete the transformation now.
Sophie helped him put the stockings on leg by leg, reminding him to watch how she did it because she wanted him to do this part on his own come Halloween. Gustav then slid on the heels by himself and as he stood up, he lost his balance a little, but managed to correct himself.
"Okay, now, sweetie, I want you to come and step into your dress."
Gustav's mind reeled at the idea of "his" dress but he walked up to his mother, and stepped into the lovely blue dress. It was nothing fancy, but was merely an understated party dress. Gustav wasn't impressed with it, but he let his mother zip him into it regardless. Sophie fluffed the dress up and held her hands together in please as she watched Gustav gaze at his reflection.
He couldn't believe it. This was the kind of girl he would have a crush on under normal circumstances, but it was himself in that mirror. He grabbed at his dress and body in disbelief.
"Turn around, let me get a good look at you, sweetie," asked Sophie.
"How do I look?" asked Gustav.
"You need a little work, but you make a pretty beautiful young woman. You're a shoe-in to win the Halloween contest, dear."
Gustav was flooded with strange emotions. As he looked into the mirror, he saw something different than what he had been seeing for his entire life up to that point. He had become an attractive person. As a boy, he always felt ugly and plain, but as the girl in the mirror, he felt good. He dare not share this feeling with anyone else, especially his mother, and suppressed the thought.
Gustav continued to glance at his feminized being in the mirror. He was excited, scared, and confused all at once. He didn't know if he completely liked what was going on his is head, but some aspects were appealing. He could feel something change inside of him, but he couldn't understand it.
That night, Sophie trained Gustav in the second half of being a convincing female – the presence. As they sat and had tea, Sophie showed Gustav how to properly sit and cross his legs, and use his arms to make feminine gestures. Gustav, being a quick learner and open to adaptation, played the role quite well. He was beginning to almost look forward to going to the Halloween party. It wasn't like he had much choice in the matter, but he figured if he played the role well enough no one would recognize him. Then he would be welcome to leave without garnering too much attention.
As the night came to a close, Sophie was proud of Gustav's effort and was seriously considering that her plan could work. She felt sad that she had to end the night and get Gustav out of those clothes.
"Dear, its almost time for bed – we need to get you out of those clothes," said Sophie regretfully as she began to remove Gustav's wig. Gustav felt as though this experience may have been too short, but Sophie had other plans for him. Sophie finished helping Gustav remove the dress, the stockings, corselet, and the makeup. Gustav walked into his room and found a pair of shorts and a t-shirt to sleep in. As Gustav looked in the mirror in his bedroom, he noticed one problem.
"My eyebrows – why did we have to pluck them! Everyone at school is going to laugh at me. They'll know!" screamed Gustav.
Sophie quickly entered Gustav's room after hearing the commotion and found Gustav doubled over on his bed crying and clutching at his slightly feminized brows.
"They're going to laugh and they're going to beat me up." Gustav continued into a blubbering, frantic cry. He was near inconsolable. Sophie sat next to him and realized she may have gone too far with him too soon. Or possibly, she took him out of the feminine clothing too fast.
Sophie grabbed Gustav gently by the shoulders and lead him back into her bedroom. She gently sat him down and began to remove his clothes again. Gustav responded well to this and though he was still crying, he did not resist. Sophie found a pair of panties and nightie she had purchased just for Gustav. Gustav's eyes were so blurry from the tears he didn't notice his mother removing the tags from the new girlie articles.
Sophie motioned Gustav to stand up as she ran the pink panties up Gustav's legs. She tried to tuck his modest penis under the sheer panties, but it didn't look right. Almost as if she had done this before, she reached for a role of tape she happened to have ready and then began to reform Gustav's penis into a flat form against his body. Amazingly, Gustav made no complaint and merely sobbed acceptingly as Sophie did her work. She slid the panties back up. Sophie, wondering how much further she could go, reached back into her bag of tricks and pulled out a maxi-pad. Gustav noticed the feminine implement but again made no mention. He seemed to be regressing into a super feminine mode of some kind due to his stress over his eyebrows.
Sophie positions the maxipad in place and smoothed over his panties, smothering his penis. She then grabbed the nightie and slid it over his head. Gustav just submissively raised his arms as she slid the beautiful nightie over his head. Sophie lead Gustav over to the vanity and began to work on his face. Sophie asked Gustav to control his crying as she began to do his makeup. She then set his natural hair into a cute style and tied a ribbon in his hair. As a final feminine touch, Sophie slid a garter up Gustav's leg and lead him to the soft bench in her room.
Gustav bounced into his feminine persona again as he daintily explained his situation while still sobbing.
"Mother, my eyebrows are going to be a dead giveaway – they're going to call me gay and kill me," Gustav said as he fingered the soft fabric on his new nightie.
"I don't like being dressed like this," said Gustav in a distinctly feminine manner.
"Of course not, dear," said Sophie.
"I'm doing it because I'm a winner – and I'm going to win. I need to practice, after all," Gustav said – he was beginning to calm down.
"Of course – I'm so proud of you. Your eyebrows will grow in soon. I'm so proud of you, but you must go to school."
"No one noticed me anyways," sighed Gustav.
"Gustav," interrupted Sophie.
"No, its okay, I'm fine now – I don't think this will be a problem," said Gustav as he got up and walked, fully dressed in his girl persona, to his room to go to sleep. Before he fell asleep, he rested his hand over his flattened crotch and felt his maxi pad covered penis. For some reason, he felt a little more at peace. Sophie had felt that she had made serious gains that night, even at the expense of possibly traumatizing Gustav in some way. Her plan was unfolding in ways that were faster than she had hoped.
That night, Gustav had strange dreams of femininity. So startling and abstractly strange were these dreams, it shocked him out of his nightie that morning. He didn't like the way he had submitted to the clothes last night. He would only dress in the girl clothes one more time – only for the Halloween dance – and then this confusing ordeal would be over.
Halloween had finally arrived. Sophie encouraged Gustav to get ready for the day on his own in her bedroom. As Gustav was taking his time getting the girl costume back on, Sophie was downstairs, enjoying a tea. She heard the doorbell ring and then Gustav yelled from upstairs – "That's probably Charlie!"
As Sophie opened the door she was pleasantly surprised at the coincidence.
"My, my – aren't we beautiful, Charlie. Come on in."
As Charlie entered Sophie's house, he was lead to the kitchen area to enjoy a tea and wait for Gustav. Charlie was wearing the new super short, and cute dress he had bought for Halloween. As he walked into the kitchen and sat on a chair, Sophie noticed how well he walked in the heels and even how his breasts jiggled.
"That's a really convincing costume. Those little boobs almost look real. And those hips…"
"Um, ahhh, well, its all in the make up and tape," said Charlie, nervously. "Is Gustav almost ready?"
"Of course, he'll be down soon – he's getting his rather, how do I say it, elaborate costume on – I think you'll like it," said Sophie as she leaned into Charlie and unceremoniously touched his very real budding breast. Charlie was frozen. Sophie figured him out.
"You know I'm a doctor, Charlie, right? I know what you are doing to yourself."
Charlie, confident but cautious, blurted out "Please don't tell anyone – I'm not ready yet.
"You seem pretty ready."
"This is Halloween – its my night to walk out and feel comfortable as a w- wo- woman. They woman I truly am."
As Charlie confessed to Sophie, they began to talk comfortably. Sophie could understand how Charlie may have felt. As Gustav was rolling his stockings up his legs upstairs, Sophie gave some valuable information to Charlie. Meanwhile, Gustav slipped on his heels, checked his look and descended the stairs.
Charlie met Gustav at the base – they both looked at each other without saying a word and then took Sophie's car to the Halloween dance.
They dance was uneventful. Compared to the rest of the Halloween costumes, Gustav and Charlie looked like just another pair of girls. They spent most of the night dancing awkwardly in the one of the corners. They politely turned away the drunk high school losers trying to hit and them and spent much of the night not saying much to each other. Both were too nervous about being found out to enter into the costume contest.
Finally, Charlie said "This dance is lame, let's get out of here."
Gustav demurely agreed as they both walked, clicking their heels to the parked car. As they both sat in the car, Gustav needed something to do and opened the purse his mother had lent him to help sell the costume. He filtered through it, looking for something to do to break the awkward silence. He finally gave up and pulled out one of the only things in there, a lipstick, and began to refresh his make up in the mirror. Charlie interrupted.
"How come you didn't tell me you liked to dress up as a girl?"
"Oh – My mom made me do this. It was her idea. She wanted me to win the contest. She is going to be mad when she finds out I didn't even enter"
"But, you're so good at it"
Gustav blushed with anger and embarrassment.
"What about you, Charlie? I mean, I'm not the only one in panties here."
"I wanted to tell you something, Gustav – I want to be a woman – for real. This is not a costume," said Charlie as he moved closer to Gustav.
"I don't know what you mean," said Gustav nervously.
"Can I tell you another thing, Gustav? I like you more than a friend should like you. I want to be a woman, so you can love me as woman. But I didn't know you were into being a girl too!"
"I don't want to be a girl!" said Gustav defensively – almost oblivious to Charlie's confession of love.
Charlie leaned into Gustav and began to kiss him. Gustav reciprocated for a moment but regained his composure immediately.
"Stop it, stop it! I'm not gay! Get out of my car!"
"But Gustav I – "
"NO! Get out of my car. I cant handle this!"
"Gustav, please. I don't think you understand!"
"I do. I understand completely. I'm not like you. Now get out! Please!"
Charlie got out of the car, defeated. He kicked off his heels and went home. At that moment, he made the choice that he needed to move on with his life. Gustav would not see Charlie for another year.
Gustav sped home that night, slammed the door, ran into his house, past his mother, throwing his wig at her and ran up to his bedroom. He locked his door and looked in the mirror and he wept.
"What's happening to me?," Gustav asked his reflection. With his dress and stockings still on, he collapsed onto his bed. Sophie knocked at the door.
"Are you okay, Gustav."
"Leave me alone! I'm never wearing this girl shit again. I HATE it! Leave me alone, mother!"
Sophie walked away from Gustav's door. She feared she made a dreadful mistake.
For the next little while, Sophie and Gustav did not speak. They came and went at different times and rarely was it that they crossed paths. Gustav was in an especially depressed mood, crying by himself in his room at night. One afternoon, while his mother was not home, he was in an especially foul mood. As he lay in his bed, he thought about the time his mother dressed him in that nightie. He remembered how good it made him feel and how calm it made him. He began to look for the nightie but remembered that he had thrown it out in a fit a rage after his post Halloween girl purge. He had wanted nothing to do with girls things.
Things were different now. He wanted to bathe himself in femininity. Maybe it would make himself feel better. In an act of desperation, he took his savings stash from under his bed, grabbed a baseball cap, which he wore close to hide his eyes, and then got into his mother's second car and sped for an out of town mall.
While Gustav was in the mall, he went to the department store and made a beeline for the women's section. He was nervous as hell but he needed the clothes. He quickly went to the lingerie section, grabbed a brassiere and panty set but wasn't sure if they would fit. Suddenly, a young woman made herself available to help Gustav.
"Don't worry – I get lots of young men here. You're very pretty. You'll make a pretty girl one day," whispered the pretty young woman.
"Its not for me. It's a present for my girlfriend," said Gustav embarrassed.
"Oh! Of course. What size is your girlfriend," said the young saleswoman understandingly.
"I'm not sure," said Gustav.
"I bet I can guess what size she is," said the saleswoman knowingly.
The salesgirl helped Gustav find a bra and panty set and then lead him over to the young women's clothing area. Gustav picked out a skirt and top and a pair of tights with her help. She also helped him get some makeup, heels and even a brown wig.
"Thanks for helping me out," said Gustav.
"You're girlfriend will love the panties, bra and outfit you bought her. I bet they will fit you, - er, I mean her, perfectly. I'm sure SHE is very pretty."
Gustav paid for his items and rushed home. He was broke, but content that the clothes would make him calm again.
Luckily, he came home long before his mother came home and decided to get dressed. As he stripped, he caught his naked body in the mirror and marveled at how much weight he lost from his recent stress. He went to the washroom, took a quick shower, shaved all of his body hair off and patted himself dry. He grabbed a maxi pad from the dusty bag under the sink, and some tape. He ran to his room and then immediately reached for the bra and panty set and slid them on. He tucked his penis under his legs quickly. He stuffed his new bra with socks and then slipped on his new heels. He looked in the mirror.
Gustav was pleased, but he wasn't done yet. He sat on his bed and looked into his mirror. He contemplated his face and noticed that his eyebrows had grown back in. Did he want to pluck them? He did buy a set of tweezers. He spilled his new cosmetics onto the counter and got to work. He did his makeup, and then put on his new wig.
"Why do I like this so much?" Gustav asked his refection as he blew a kiss.
He modeled his bra and panty, looking in the mirror before realizing that he had missed something. He pulled his panties back down and applied some tape to his penis to keep it in place. He reached for a maxi pad, unrolled it and stuck it to his panties. He carefully slid his new panties up and smoothed them over his now flat crotch.
"Why does this feel better?"
Gustav removed his heels, and then rolled his tights on. He finished by stepping into his skirt and pulling his top over his head. He placed his heels back on his feet. With his eyes closed he stepped in front of the mirror and opened them.
"What's wrong with me?," Gustav asked his reflection. He did not expect an answer. He felt calmer, and he liked the result, but he knew this was not right. He pushed those feelings aside and spent the rest of the night reading women's magazines in his bedroom. For the first time in weeks, Gustav felt at peace with himself.
Chapter 7 - Caught and Punished
As the weeks passed, Gustav became more comfortable with his activities. He'd only dress when he knew he had enough time to do so without risking his mother catching him. He'd also gone twice more to the same store to get more women's clothes. The first time, he wanted a new outfit and lingerie, and the second, he felt he could use a swimsuit for sunbathing. He hadn't used the swimsuit outside in the backyard yet, as he felt the risk of exposure in his backyard was too high. He was having trouble hiding all the clothes he was collecting. All in all, Gustav had come to accept his strange habit and hoped that he would be able to keep it his own little secret. Unfortunately, others had started to take notice in his personality changes. Others had noticed the trimmed and sculpted eyebrows, some had seen the way he walked change - but for people who thought he was a bit of a loner and strange in the first place, it was nothing to get excited over.
One person who had been keeping a distant eye on Gustav was his mother - She had noticed the still plucked eyebrows and had even thought she had seen a hint of a pink panty when Gustav bent over to pick something up in front of her one day. Sophie definitely knew something was up...
One night has Gustav had been in his room trying to hide his recent new purchases of femme delights, he noticed a recent purchase he had not tried on yet. A new pink baby doll nightie. He slipped on the delicate garment and admired himself in the mirror.
Suddenly, he had heard something against his window. At first, he dismissed it, but the small sound came back, again and again. Someone was trying to get his attention. As he looked out his window on that dark, rainy night, he couldn't make out the figure, but he knew who it was by the voice.
"Hey, Gus! It's me...er, Charlie! Let me in, I'm getting soaked out here!"
"Shhh, you'll wake my mom up," said Gustav in a loud whisper. He remembered what he was wearing and threw a robe over it in order to hide his shame.
Gustav ran down and let Charlie inside. Charlie was wearing a large rain jacket and hat which were soaked. Gustav noticed something was amiss, but it was too dark to see anything clearly.
"Hurry up, no time for greetings, mother is strict with visitors at this time of night. Quickly, to my room. And with that, a trench coat and hat clad Charlie followed Gustav up to his room.
"You can put your jacket on my coat rack to dry, Charlie," said Gustav. He feared what he would see under that trench coat. The last time they had been together, Charlie had admitted to Gustav that he wanted to be a girl for keeps and had then tried to kiss him. It had been months since that night and since then, Gustav had only heard the rumors. He had heard that Gustav was working in the big city under strange circumstances.
"Thanks, Gus. Hold on, let me get this wet stuff off," said Charlie as he removed his wet clothing revealing the surprise underneath. Charlie was wearing a beautiful dress, heels, and jewelry. His hair was all done up and his makeup looked perfect. Gustav could not believe it. He knew what Charlie was up to, but he had no idea you could take it this far in less than a year.
"Char- Charlie?" gasped Gustav. Gustav felt ill. Is this how far you could take it! Would this be him one day if he kept up his strange habit? Did he catch whatever it was Charlie had?
"Well, I know it's weird, but I figure you should know. I've truly found myself. I feel like a woman and it feels great," said Charlie.
"Charlie! But how?! You're a girl now!"
"Gustav, honey, I love you, but can you please start calling me Maggie? I'm Maggie now! And I'm not a 'real girl' yet. But I will be a woman one day. Gotta save for the 'operation'"
"O-okay, M-Maggie...Everything looks so real," said Gustav as he poked one of Maggie's breasts.
"That's because it's all too real," said Maggie as he motioned to Gustav to his dress zipper, "Help me out here, dear."
Gustav reached for the clasp of the dress and helped Maggie get it down enough so he could take over. Maggie undressed to his bra and panties, revealing a flat crotch and very real set of breasts.
"You see, Gustav, when I got into the city, I started work at a drag cabaret. The owner encourages all his talent to take female hormones and he even sponsors certain surgeries. I'd had some ribs removed and my breasts were done."
"Oh, that's tucked away. Still have the pesky thing. But that's what I came here to tell you. I'm going in for the full sex change. I'm going all the way, Gustav."
"By the looks of it, I thought you already had. You look like a princess!" said Gustav as he sad down, flabbergasted. He unconsciously let his tight grip on the bust area of his robe go when he did so, revealing pink fabric to Charlie.
"Um, Gustav, you look like you have something to tell me too."
"Oh, this, um," said Gustav as he grabbed the collar of the robe.
"Why don't you come back with me, Gustav. To the city. To the Cabaret! I can tell you'd be beautiful. You'd make lots money!" said Charlie as he sat next to Gustav.
"No - I'm not like you. I'm a boy. I just like," paused Gustav as he let loose his grasp on his robe, "I like wearing this, but it doesn't mean I want to be like you. I don't know what's wrong with me Charlie, but I can't do what you did. It's not for me."
"But you'd be so pretty, Gustav. You weren't meant to be like this. You'd be better off with me in the city. The men would love your look. I can tell," begged Charlie.
"The men? What do you mean?"
"Well, you know. I always thought you liked, you know...boys, like me?"
"I'm not gay, Charlie. I'm NOT!" Get out, Charlie, get out!" cried Gustav. He didn't want to think about the possibility.
"But, Gustav! We could be sisters! Reborn as sisters! Please!"
"No," sobbed Charlie as he turned to his bed and cried into his pillow. The full extent of his babydoll revealed to Charlie.
"Oh- okay, then, Gustav. I understand. I'll let myself out then," said Maggie as he quietly exited, being sure not to wake his mother.
Gustav cried himself to sleep. Unable to accept what had just been offered to him. He did his best to suppress that evening.
"Ooooh, that Charlie, thinks he knows everything!" cried Gustav. Outwardly, he was very angry with Charlie, but secretly, Gustav was very jealous. He just didn't know how to process those feelings.
On a Sunday, Sophie had made a brief announcement before she left the house.
"Gustav, I have to make a few emergency appointments today - I'll be out all day and I've left some money for lunch on the counter."
What Gustav didn't know was that Sophie knew something was up. She had planned to come back shortly, and see if Gustav was up to anything. Gustav heard his mother slam the door shut and was happy she was out. She was usually always home on Sundays, and Gustav decided he would do something extra girly that he had his mind on for a few days now.
As Gustav walked down the stairs to the family den with all of the trophies, he paid special attention to the blue nightgown his mother had worn as a beauty queen. He walked up to the dress and felt the exciting and shiny fabric - he wanted to wear this. He didn't know why, but he wanted to put this dress on right away. Gustav removed his clothes, leaving on only his pair of pink panties. He removed the dress from the dummy and carefully slid it onto his body. He was quite comfortable with women's clothes at this point, and was able to zip it up without problem. As he twirled around, could help but feel giddy. Wearing the evening gown felt so great to him.
As he spun once more, he lost his balance and struck his hand against the wall, knocking loose a piece of the stone at the wall. As he kissed his sore hand, he took a closer look at the loose stone in the wall, he noticed that it looked strange. He grabbed the stone and with a little jiggering, he was able to get it out. Behind the stone, he found a small book - a journal of some sort.
Gustav sat down and paged through the first few pages of unreadable handwriting until he came across a picture of a young man.
Gustav felt as if he had seen this person before. Could it have been his father? Gustav was intrigued and crossed his legs to get more comfortable in the elegant gown. As he turned to the next page, he thought he heard something, but he ignored it and carried on. He passed some more unreadable handwriting and came across another picture. This time, it was the same man, but he looked younger.
There was something very familiar about the picture, and as he was about to turn the page, he heard a familiar throat clear. It was his mother. He had been caught in the blue dress!
"So this is what you have been doing when I was away? And that book? Where did you find that!? Give it to me!"
"I...I....I - was just seeing if it would - um - the book - ugh," said Gustav, who was at a loss for words.
"Take that dress off right now," said Sophie in anger. She helped Gustav out of the dress and noticed his pink panties - with a flat crotch as his penis was tucked; a thing which he was doing quite often.
"Where did you get those? I thought you were done with girls' things - I thought you were too manly?"
"Um -," Gustav could not say a thing. He just grabbed his clothes and ran for his room. He could hear Sophie only murmur as she placed her prized dress back on the dummy.
As Gustav ran into his room and fell on his bed, he was in a state of fear. He didn't want anyone to know he got pleasure from wearing women's clothes. Even though he knew his mother had even encouraged it at one point, he didn't want anyone to think he was less of a man. He wanted to keep it private. He was fine with that.
Gustav heard his mother coming up the stairs - she then knocked on the door. Gustav answered it.
"Where's the rest of it - show me your stash," said Sophie very plainly. Gustav got up, walked to his closet and procured a box that contained all of his feminine pleasures. It even had some makeup and a little girly hand mirror.
"From this point on, I'm in complete charge of your girly little problem. Do you get off on this stuff? Do you want to be a girl?"
Gustav didn't answer. He didn't want to. He knew he didn't want to be a girl - but he just liked wearing the gear. He was content with that.
"I'm going to send you away. If you want to dress in girls things, I'm going to have you cured."
"No," Gustav answered - "Don't send me to an asylum! I won't wear this stuff anymore, I promise!"
"Oh - I won't send you to a psychiatric ward - I'm sending you to a better place. You'll like it - maybe," Sophie's tone took a sudden turn for the softer.
"What are you going to do with me?"
"I'm convinced you are not what you seem, Gustav. You need a change in life and I know of a program that can offer you an alternate solution."
"What do you mean?"
"You wear these clothes, Gustav, but being a girl is not about fun. Its serious business and you're going to learn that. I'm going to send you to an academy that specializes in turning confused young men like you into normal young women."
"I - I don't know if you are serious, but if you suggest that I get a sex change - "
"Not a sex change, Gustav. We're going to reassign your gender. I mean, that is what you need. Why else would you be wearing women's clothes?"
Gustav had no answer.
"If you like the clothes, you'll love the real deal. You're going all the way, Gustav."
"No - I never meant to have a sex change - Please, Mother! Don't do this to me," Gustav said in a panic.
"It's too late. I've already paid for the full program. After one year, you'll be thanking me for the choice I made for you. You'll be better off."
"I'll run away!"
"No you won't - You'll go. And you'll like it!"
Gustav knew he would never run away. He knew he was socially inept. He knew he would starve or die in the real world. He submitted to his fate rather quickly and Sophie knew he would.
"You ship out for the Future Girls Academy on Monday, Gustav. They'll provide you with everything you need for your transition into a new gender. Training, clothes and life skills will be imparted to you while you are chemically and surgically transformed into a girl."
"Does that mean, they cut off-"
"It's a complete deal, Gustav - I'm not sorry though. It is what you need."
Gustav began to sob uncontrollably. Sophie left him on his bed and left the room and quietly closed the door.
Gustav stood up, tears streaming down his face and walked to his mirror. He tried to imagine himself with breasts - real breasts. Like Charlie, who was now Maggie. He wasn't playing anymore. He was caught and now he had to pay the price for what he perceived to be his sins. Gustav was conditioned by his mother to always accept his punishments. Because if he didn't, she could make it much worse.
Sophie drove Gustav to the out of state Future Girls Academy the next month for the start of the new semester. Gustav was to be part of the fresh stream of confused youths to enter the Academy. The school was divided into two streams, six months apart. As Gustav looked out the window to the front gates of the academy, he noticed the crest.
Sophie parked the car and Gustav got out and removed his suitcases from the trunk. As he lifted the two suitcases up, he thought about the girls clothes they contained. Sophie purchased sets of panties, and frilly bras. She had found his full set of bras, and decided to indulge him - making him want more. Gustav knew what she meant. The suitcase also included his uniform, which he did not have to have on just yet. He was allowed to arrive at the Academy in his regular clothes. He knew this was the last time he would wear them and he picked his favorite slacks and golf shirt. The suitcases also contained a variety of casual, semi formal and formal girls clothing for him to wear. Sophie promised to ship more up in the coming weeks.
As Gustav and Sophie walked in the courtyard to the dormitories, carrying the suitcases, they took in the scenery. Gustav observed what he would learn later to be the "second stream" students, who had already been there for six months. They all appeared to be relatively happy young women. They were six months ahead of Gustav, and he noticed very little masculine about them. Would he have to go that far? Was this a strange dream or nightmare? Gustav knew he had no other options and rolled his suitcases to his dorm room.
It was in his rather large and posh room that he met his two roommates. Gustav first met Steven, who was a rather short and bookish young man. He was clad only in his underwear, unpacking his suitcases into his closet.
"Oh - hello," said Steve as he blushed slightly.
"M-my name is Gustav."
"I'm Steve - well, I want to change it to Shawna, actually, but my mother tells me she was going to name me Stephanie if I was a girl. Do you have a girl name, yet?"
"I - I, " stuttered Gustav, who was slightly put off by Steve's forwardness, especially as he was wearing nothing but undies and holding girls clothes in his hands.
"We haven't decided yet," interrupted Sophie, "but I'm sure Gustav will be inspired soon - its nice to meet you, Steve."
"Likewise," said Steven.
Steven then carried on with his unpacking as Gustav turned his attention to Roger, a rather normal looking long haired boy.
"Hello - I'm Roger," said the lanky young man.
"Nice to meet you - I guess we're all roommates in this together."
"You - you don't seem to be, um - a," Gustav was at a loss for words looking at Roger.
"A girl?" said Roger bluntly.
"I'm sorry," said Gustav.
"No worries, I'm just in boy mode - you know? You have to spend so much time being 'normal' - you know what it's like Gustav, right? Don't worry, I'm one of you girls," said Roger.
Gustav remained silent as he grabbed his mother's hand and gestured for them to walk out of the room. Gustav excused himself and walked with his mother to the hallway.
"These guys want to be girls? I thought it was a punishment? They seem to want it?" whispered Gustav to Sophie.
"I never said this was a punishment, Gustav. You're the one I caught wearing dainty brassieres, skirts and blouses. It seems to be what you want. Are you going to give me trouble, Gustav?"
"Oh, no, mother. I don't want you to make this worse," said Gustav in complete obedience.
"Now, run along to the car and go grab my purse. I forgot it there," said Sophie as instructed Gustav, but it was a ruse. She wanted some time alone with the other boys in his room.
"Steven, Roger, I need for you to do me a favor. Gustav may seem like he doesn't want to be here, but being a girl is all he can think about. His psychiatrist says girldom is the only thing that can cure his emotional problems. He is just having some trouble coming to terms with his condition like you two have. I want you to make his time here as girly as possible. No boy stuff. 110% feminine. Understand??"
"Yes, ma'am, but why do you want us to help you?"
"I'll reward you of course," said Sophie avoiding a direct answer," I'll pay you two enough to keep you in feminine finery of the best kind."
"Rewards, eh," said the boys," well, since we're already dying to get girled up, I guess helping Gustav won't be too hard."
"Good. Just remember, you'll be reporting to me. I want to know that Gustav will be getting the full female environment in her dorm that the classes will provide. And I won't forget about your rewards."
"Thanks, ma'am," said the boys. It seemed like an easy task for them. It was, actually, but it would be hard for Gustav.
"Don't be afraid to be a little rough if you need too. And here, take this" said Sophie as she handed Roger a box.
"It contains super girl hormones of my own patent. You two can take them, but make sure Gustav gets a good dose every day. Wait until he's asleep to inject him. Results will be quick!" said Sophie as she left with a smile.
Chapter 8 - September
The next day classes were set to start. Gustav wondered what the classes were all about when he opened his orientation package and found that the first semester consisted of Makeup, Dressing, Movement, Group Therapy, Transition with Hormones and Voice Training. He felt butterflies in his stomach. Along with his orientation package, he received a school uniform in five multiples - one se for each day of the week. It consisted of a tie, blouse, jacket and skirt. The jacket had the school crest on it. Gustav couldn't help but admire the fabric of the skirt but he snapped himself out of it.
"No," he said to himself, "this is not me. I'm not going to be like Magg - er, Charlie."
"Did you say something, Gustav," asked Roger.
"Um, no," said Gustav as he removed his hand from the skirt.
"Well, you should get dressed already. It's almost time for orientation."
"I'm just going to wear what I am now," said Gustav.
"I'm afraid you can't," said the bookish Stephen, "Uniforms are mandatory."
"I'm sure it will be okay - it's just orientation," said Gustav, "just leave me alone."
"As your roommate, I'm afraid I have to take responsibility here, Gustav," said Roger, who seemed the leader type.
"What do you mean?"
"Well, do you want to get in trouble? I hear the punishments here are strict! Why don't you just fall in line."
Gustav thought about what would happen if he didn't wear this uniform and his mother found out. He did not want to ever be on her bad side. Even without her even being there, she kind of was. Gustav sobbed a little while sitting on his bed.
"Listen, guys," cried Gustav, "this is really weird and I don't think I even belong here. I just like to wear girls things. I don't want to be a girl. Isn't there a difference?"
Stephen and Roger, remembering their orders from Sophie moved closer to Gustav.
"It's okay, Gustav. We can help you get dressed today," said Stephen as he approached Gustav, "now get up."
Gustav submitted. He had no choice. Everyone was against him in this femme prison. He lifted his arms as Stephen removed his sweater and shirt. Roger took his pants off.
"Tsk, Tsk, Gustav! Boy underwear. I'm pretty sure I watched you unload a mass of lingerie in your drawers. Let me see here," said Roger as he went to the dresser and retried a bra and panty set and handed them to Gustav. Gustav grabbed them and placed them on his bed. He didn't want people to dress him and decided to suck it up and go along for now. He would figure a way out of it.
"I'm okay now," said Gustav, " I can dress myself."
"You sure," asked Stephen.
And with that the other boys supervised Gustav as he went to his dresser, grabbed some tape and proceeded to tuck and tape his privates. He put on his brand panty and then skillfully dressed in his uniform. Though he still looked quite boyish, he wouldn't be breaking any protocol.
When Stephen and Roger dressed, they looked considerably more feminine.
Gustav felt these two might give him trouble. They were girls for keeps.
Gustav's first day went well. He flew under the radar as not to be caught up in the feminine brainwashing. The class that most scared him was Hormones. It wasn't a class so much as it was a clinic. For an hour, all the boys in his class waited in a room while each one was called up. They would come out looking considerably happy. Gustav knew what was happening to them to be so happy. When it was his turn to go into the small room for his visit, he almost fainted.
The nurse asked him to expose his buttocks.
"I'm not sure I should be here," said Gustav as he watched the nurse prepare an injection of what was no doubt female hormones.
"There's always one like you, isn't there? Well, this can be easy or it can be tough. I have instructions to get everyone one of you boys medicated. DO you want it the hard way?"
Gustav, ever the pacifist, again submitted to his fate. How would he get out of this?
After all the students received their injections, they were to meet in an auditorium where it would be explained to them what was in store for them.
A beautiful woman stood up at the front of the auditorium and explained to them the process.
"Congratulations on your first step to womanhood!" The woman said.
The entire group applauded except one.
"The first injection will get you on the way. You will be required to be on a regime of vitamins and weekly injections that will eventually complete the chemical process of becoming a young lady. Soon, surgical options will be offered as well."
One student raised his hand. It was Stephen.
"What kind of surgical options?"
"Breast augmentation, castration, facial surgery and eventually a full sex change."
The room erupted in excited murmurs. Gustav was silent. The rest of the meeting outlined the complete change which would take place over the next year. All Gustav could think about were the hormones coursing through his body. Fast action female hormones which promised results.
Chapter 9 - October
With time, Gustav found that though Roger and Stephen could be forceful, they were also becoming good friends to him - as long as he stayed in character. He found that the more girlish he acted, the nicer they were to him. Which made his life at girl school easier.
Every week, a care package of feminine items would reach Gustav from his mother. Panties, bras, razors, dresses and the like. Gustav has to resist his urges to the highest degree in order to resist falling to much into the trap.
One day, as the future girls were studying for school by reading women's magazines, Stephen and Roger looked at each other understandingly.
"You know, Gustav, you're mother is nice enough to send you all this great stuff and all you do is use your boring pink pajamas for bed time." Said Roger.
"These are girl's pajamas, guys. See the hearts?" said Gustav.
Roger and Stephen were both wearing teddies and babydolls every night. They couldn't get enough of the freedom they offered.
"You're mom sent you a nice teddy, why don't you try it on, Gustav?" asked Roger, "you might hurt her feelings. What if we tell her you're not wearing the stuff she goes through all the trouble to send you. You wouldn't want to make your mom sad would you? Or mad?"
"Fine! I'll put something else on. If only to get you two off my back, damn it," said Gustav as he went to his dresser and removed a teddy from the top drawer and slid it on expertly.
Stephen and Roger began to laugh at him.
"What now?" asked Gustav
"You didn't tuck, Gussy!" said Stephen.
Gustav resigned and quickly tucked his penis away to please his roommates so he could get back to his reading. Something felt strange though. The feeling of the silk against his skin felt better than it usually did and he felt that feeling he so enjoyed from girl's clothing. For a moment he was enraptured in his feminine bindings. Usually, at this height of femme pleasure, Gustav would feel his member bulge, but not this time. It seems the hormones have deadened that movement. The kind of sexual pleasure he was feeling now was slightly different and more sensual. Roger snapped him out of it.
"Now, doesn't that feel better?" asked Roger as he stroked his hair in a sympathetic manner
Gustav ignored him and fought the feelings back. Things were getting too feminine for him. Tomorrow was Sunday and it would offer a reprieve from the womanly bindings of his new life.
Gustav awoke on Sunday, still clad in his pink silk teddy to an elated Roger and Stephen. As it turned out, the headmaster had arranged for a formal tea later on in the afternoon and had made it so uniforms were not required. The only requirement was that all students dress in their best dresses. Roger and Stephen could not wait to get all gussied up for the semi-event.
Gustav was not so pleased. This school had begun to indulge his fantasies but he was approaching a future that worried him. He again felt as if he was losing himself every day he was here. The incident with the teddy he was wearing, and the pleasure it gave him, was proof he was in over his head.
"Gustav, you'd better wear that big bra your mom got you. You know, the one that you can use those expensive falsies for? What would your mom think if those falsies went to waste?" said Roger as he began to get dressed. Gustav watched Roger as he transformed into a girl.
Roger loves his thigh highs.
Roger likes to take his time to tie his hair up and put his bra on as well.
And finally, time to cross his legs and put some makeup on.
Gustav found it interesting how quickly Roger's demeanor changed the moment he got dolled up.
"Mmm, I feel so cute and sexy," said Roger as he moved his bands from his chest to his crotch. He made sure to pat his crotch down so his penis was as flat as possible.
Gustav also watched as Stephen dressed. It was the same thing. Stephen would transform from a nerdy boy to a cute and sexy young woman. It was so strange.
"Now, it's your turn," said Roger. Gustav began by placing his brassiere and panties on. He then stuffed his falsies into his bra cups.
"Oooh, those look so real," said Stephen as he felt Gustav up.
"Ouch," said Gustav as he pushed her hand away. His chest was beginning to become quite sore as the hormones were finally taking effect. His hair had also grown a little more so his roomies could not do a little something with it.
Once they were finished getting him into his dress they made him parade around so they could get a look.
"Very beautiful," said Roger as he helped straighten Gustav's rather revealing dress. Gustav felt extra embarrassed by it. He could feel the cool breeze caress the tops of his thighs.
Roger and Stephen giggled as they held Gustav's hands and lead him to the headmaster's private area.
The next we see our girls they are exiting the headmaster's room with large smiles on their faces. Well, Roger and Stephen had smiles. Gustav didn't. It seems the three of them had been chosen to be put on the surgical fast track ahead of all the other boys as part of a pilot program in the school. They were to be a part of a study on accelerated gender reassignment as they all qualified. It turned out, the person leading the study was none other than Gustav's mother Sophie.
"Can you believe it? We get our orchedectomies tomorrow and Breast Implants the next week?" said Roger.
Gustav was pale and sick. He didn't say a word the whole morning. He couldn't believe his mother was doing this to him. But he wouldn't stand for it. He was planning to run away that night and live as a grafter. Maybe Charlie could help him. He would live as a girl part time if that was what it meant to survive, but he wouldn't need any surgeries to pass. He knew how femme he looked already. And from what he learned from Hormone class, the effects were reversible, but having his testicles removed was forever.
"Gustav, you're not saying anything," said Stephen.
"Umm, I'm just hungry, is all. I need to go to my room and relax for a bit," said Gustav nervously. Roger and Stephen could sense something up with Gustav.
"Let us follow you and help you out," said Roger.
As Gustav sat down in his bed and stared a the wall he tried to devise a plan, but Roger wouldn't have it.
"Here, Gustav, why don't you try this."
"What is it?"
"It's red wine. Why don't the three of us girls celebrate! We're on the fast track to being real girls. I can't wait to get my balls chopped off," joked Roger.
"I don't really drink."
"Nonsense," said Roger as he essentially forced a wine glass into Gustav's manicured hands.
"Well, fine," said Gustav, figuring the alcohol would sooth him. He was having trouble thinking.
Gustav took a sip and as he looked at the lipstick stain on the tip of the glass he began to feel dizzy. He was drugged by his roommates with powerful stuff.
The next thing Gustav knew, he was lying down in his bed and he felt a dull pain in his groin.
"What happened?" said Gustav as he awoke. He needed to go to the bathroom real bad. As he pulled his panties down and felt around for his penis, he noticed something was strange. His penis was still there but something felt different. Then it hit him. He was drugged by Roger. He must have had the procedure as he was passed out!
Gustav couldn't even stand any more. He sat down on the toilet as he relieved himself and cried into some toilet paper.
As the months sped by the changes began to add up. Gustav's breast surgery went well and the super hormones he was getting were taking great effect. Within a short period of time, Gustav's transformation was very impressive. As were Roger's and Stephen’s.
It was a Saturday, so the boys were allowed to do as they wished for the day. As Gustav sat in front of his vanity and put his makeup on, he noticed that his hair was not very pretty that day. He was letting it grow out, but now was the time to get it styled. Something he had been putting off as girl lessons and school were always keeping him busy.
"What are you doing today?" asked Roger as he walked behind Gustav. Gustav could see him in the reflection of his mirror.
Roger had taken well to the hormones and surgeries. If it wasn't for the penis in his panties, no one would ever know he was once a scrawny boy. He had gained lots of weight, but in all the right places. Gustav admired his full bosom as it pushed against his specially made DD bra.
"My mom is coming to visit soon and I figured I'd get a nice haircut today. You know? Get it styled and whatnot."
"Mind if I come?"
"Not at all, Roger!"
"Did I hear someone say HAIR SALON!?" said Stephen from his vanity.
Stephen had also developed curves in the right places. He was a total transformation. Almost nothing remains of his maleness and of the three roommates, Stephen was the most prissy and feminine.
"Yeah, you might as well come too," said Gustav.
And with that, the three boys got ready for their visit to a women's hair salon.
Of the three Gustav was the most casual. He decided to wear a denim skirt and a T-shirt, while Stephen and Roger wore pretty dresses.
As the boys exited the school they discussed the issue of the real world they spent so very little time in.
"So, don't forget 'girls,' I want be called Tiffany in the outside world," said Stephen as he was fluffing his hair, clicking along in his heals.
"Oh yeah, call me Rebecca. I've taken to that name," said Roger as he adjuster his large breasts in his dress.
"What about you, Gus," asked Stephen, who was now Tiffany.
"Um, I don't know. I'm so used to Gustav, you know?"
"We're not calling you GUSTAV!" yelled Tiffany.
"Fine...what about Ashley?"
"You sound like you don't even care!"
"Okay, I've always liked...this is embarrassing to admit I was even thinking about it...but I've always liked...Cindy."
"Finally," said Tiffany, annoyed.
"Alright, Cindy, Tiffany, let's go get pampered." said Rebecca, formerly Roger.
All three boys made it to Miss Jennifer's hair salon and lucky for them, they didn't have to wait very long before they were all seated.
"What would you like, honey," said the middle aged hair dresser to Gustav.
"Oh, you know, something cool, classy, easy to take care of. I'm not as girly as my friend over there," said Gustav as he pointed to Tiffany and Rebecca who were waving their hands around instructed the stylists what exactly to do.
"I've got you all taken care of, hun," said the woman, and began to cut Gustav's hair.
As the boys were having their hair done, conversation began between the women in the salon.
"So, did you hear about the strange school? I hear it's for drag queens or something. You know, the gays?" said one woman.
"No, I heard it was for boys who wanted to get sex changes. My brother's, wife's old highschool boyfriend is now the headmaster...who is a WOMAN!?" said one portly woman excitedly.
"Wow, can you believe? In our small town? How come we never see any of these freakshows in town? Those fags better never try to seduce one of my sons," said another round woman.
The boys just sat their silently as they were suddenly very aware of the extra equipment tucked between their legs.
Eventually, Gustav's hair was done and the hairdresser spun Gustav around so he could see himself in the mirror.
"I love it," said Gustav excitedly. The three boys paid for their coifs and left the salon in very good spirits.
Gustav was especially nervous because he knew he would be meeting his mother after not seeing her for months. She wanted him to become a girl and Gustav was going to make sure she got what she wanted.
It was now the evening and Gustav was just finishing getting ready for his meeting with his mother. He had exiled his roommates from the room and he made sure the area was presentable for his mother. Gustav had dressed in a nice pair of Capri's pants and a conservative black blouse.
Just as Gustav was finished getting ready, his mother knocked on the door.
"Come in!" chirped Gustav. The months of vocal training made him sound just like a young woman now. Sophie walked in, placed her hands on her hips and took a good look.
"Well, well, well, looks like someone was wrong!"
"What do you mean?"
"Well, look at you! You're beautiful. When I left you months ago, you were an awkward boy. And now..."
"I'm still a boy, mom!"
"We'll see about that, dear. Now take off your clothes so I can take a quick look at my...son."
"Gustav, you will do as I say!"
"Fine," mumbled Gustav as he undressed. He didn't suspect his mother would continue to embarrass him.
Gustav stood there in his Bra and Panties. His body was almost perfectly shaped by the surgeries, hormones and exercises.
'There, are you happy? Look at what you have done to your only son!"
"Why, Gustav, according to your psychological reports, you should be ecstatic with the changes! Why are you being like this?"
"I just tell them what they want to hear. I just want to tell you that you should be ashamed of what you did to me!"
"Why would I be ashamed!"
"Look at me," said Gustav as he slid of his panties.
"I'm a freak! Do you know how the world will treat me! I am not normal!"
"No one will ever know once we take care of that...thing. Please, sweetie, put your panties back on and tuck that...disgusting piece of boy flesh away," said Sophie as she looked very upset.
"Yes they will too! They will know, mother. A part of me...wants to wear this stuff...and I...have come to like having breasts...and the attention I get.."
"Attention from whom, dear?" asked Sophie very interested.
"Oh, never mind. I'll always be a freakshow, mom. You don't understand what it's like to be me. I'm only living a lie!"
"Gustav, let me show you something," said Sophie as she sat down on Gustav's bed and pulled a book from her purse.
"Yes, it's the book you found in the basement. Now, if I recall correctly, you left off at this page."
"Yes," said Gustav, "That man. Is that my...father? What would he think if he saw me now? That's probably why he left, isn't it? He could tell I was different."
"In a way, yes, was your father a long time ago." Sophie didn't say anything more and merely turned the page to reveal something very shocking.
Gustav was at a loss for words. It was the same man, but now he was wearing a dress and he looked awfully familiar. Sophie turned the page again.
Gustav didn't say a word. Sophie merely filled in the blanks.
"That was taken a few weeks after my operation. It was so liberating to be able to wear a short skirt. They sure don't make stewardess uniforms like the used to, do they?" chuckled Sophie nervously.
"Yes, dear. I'm your father."
"And then...who's my mother?"
"You're mother was a very good person, and you could say was responsible for what I became. When she first caught me in her clothes, she was livid. She kicked me out of the house for a week until she cooled down.
"She let me back into the house, but the relationship was never the same."
"Mom, I don't want...I'm confused...do I have to hear this?"
"Yes, I've kept this from you too long. You see, when her shock wore off, she tried to accept me, but she says she was not attracted to me anymore, but she still loved me. She accepted my cross dressing and gave me lots of tips. Over time, our relationship transformed from lovers into sisters. We slept in different rooms and we had separate wardrobes. Eventually, we agreed that we would officially become roommates. She even began to bring other men home. It was awkward to say the least, but I don't blame her."
"Quiet. She sensed my depression and eventually convinced me to see a doctor who diagnosed me as a transsexual. From there, everything snowballed. Hormones, surgeries, implants. Everything except the final procedure. I was at where you are now when I decided that I wanted to have children. Long story short, your mother agreed to let me impregnate her as long as she would have nothing to do with the child. You were born nine months later. During that time, I had the final operation and...here we are, mother and...daughter?"
"Oh, mom, I never knew. No one knew. No one thinks of you as a freak?"
"Very few people know, Gustav. And it looks like femininity runs in the family. You're even prettier than I was."
Gustav gave his mother a hug and had a good cry. He finally understood what his mother was all about and he was happy to have so much in common with him. After a period of happy tears, Gustav lifted his head.
"Mom, I want to go all the way! As soon as possible. I've finally accepted myself. I'm not a freak!"
"Good. I was hoping this would a decision you would make for yourself. I know you felt like I was pushing you and tricking you, but I was doing it for your own good."
"I'm so happy, mom."
"Here, dear, I brought you another present," said Sophie as she procured a large box from an expensive lingerie store, La Petite Femme.
"Lingerie," said Gustav as he wiped a tear from his eye.
"Yes, I want you to try it on. It will give me an idea to see if we got our money's worth from this school or not."
"Wow, it's so pretty", said Gustav as he peeked in the box and carried it away to the bathroom so he could change.
Gustav emerged from the bathroom five minutes later a vision of womanly beauty.
"You are ready for the change!" said Sophie proudly.
Six months had passed and Gustav's procedures were successful. His vagina was fashioned expertly and he looked just as beautiful as any girl his age.
He was now known officially as Cindy and her doctor had officially given her the go ahead to use her vagina as any other young woman her age would.
As soon as Cindy got the okay, she rounded up her best friends, Tiffany and Rebecca and headed for the clubs. Tiffany and Rebecca were very jealous that Cindy would be the only one taking someone home tonight as they had not had their surgeries yet.
Cindy was having a great time at the club with Tiffany and Rebecca. Cindy's goal was to pick a guy who would do the job. She wanted to see if her new vagina worked as advertised and wanted to sleep with someone who looked normal. A trendy dresser who was taller than she was in her heels and in good shape.
It was a tiring search. The night was starting to take a toll on her heeled feet and she was ready to give up until she spotted someone familiar. It was Stan Stevens, a guy she knew from her highschool when she was Gustav. Only now, Gustav saw him in a different light. A few years ago, Stan was one of the assholes who fucked the cheerleaders in highschool and now he was perfect club fodder.
Cindy decided to approach him.
"Hey..." said Stan trying to place the face.
"You don't remember me. I was only at Compton High for one semester, but we had a class together, and well..." said Cindy as she flipped her hair, trying to flirt with Stan.
"Oh yeah, I remember you now..."
"Cindy," she said, helping him out.
Cindy and Stan danced together for a few songs until Stan began to get increasingly close to her. Eventually, Cindy felt what was Stan's erection against her thigh. Cindy didn't want him to blow his load yet, so she offered to take him back to her place. Luckily, Cindy didn't drink too much, so she could do the driving. Cindy was very excited to get back home.
"Tiff, Becky, this is Stan, we're heading back to the school, so, you know," said Cindy, suggesting that Tiffany and Rebecca should not come home for a few hours. They had this all planned out.
"Cool, Cindy, we'll see you later. We'll catch a cab."
Cindy grabbed Stan's hand and ran for the exit.
Cindy finally got Stan to her bedroom and they began to kiss passionately and undress each other. Cindy pushed Stan onto her bed and mounted him. She could feel his penis push against her panties and they dry humped each other.
Eventually, Stan helped Cindy with her panties and Cindy pulled Stan's penis out of his underwear. She took a good look at it and began to kiss and felate it to get him as excited as possible. She didn't like the idea of come in her mouth so she stopped just short of that. She reached into her dresser and pulled out a condom. She unwrapped it and then rolled it onto Stan's penis.
Cindy then straddled him again, reached for his penis and gently lead it into her newly fashioned vagina. As Cindy pushed herself onto Stan, she experience a feeling she never knew before. It was the first time she had sex with anyone and she loved it.
Stan suddenly took charge and flipped Cindy onto all fours and proceeded to mount her from the rear. It was this position that gave her the most pleasure she had ever felt in her life up to that point. After what felt like an eternity of pleasure, Cindy experienced her first orgasm as a woman and it was intense. Soon afterward, Stan began to thrust heavily and he came as well. The young pair collapsed on Cindy's girly bed.
After a few minutes of afterglow, Cindy politely asked Stan to leave.
"Alright, big boy, time to leave."
"Can I get your number?"
"I'll think about it," giggled Cindy.
"Seriously, I'll call you baby."
"Sure you will. Listen, Stan. It's okay. This is just a hook up. I get it. Now, get dressed before my room mates get home. And try to avoid security. I hear young boys get lost around here."
Cindy's adventures as a woman were only starting,
but you won't read about them here.