Stop Teasing Your Sister 2 Part B (Patreon)

For story with images, see PDF below. 

Trent’s mother took him to see a gynecologist, telling him that his blossoming breasts were a “female problem,” so he needed to see a doctor who understood female bodies. It was all part of the psychological rewiring of Trent’s brain, as was the flowery medical gown he was made to wear.

The actual breast exam had been a nightmare, a woman—and an attractive older one at that—squeezing, kneading, cupping the breasts she shouldn’t have, while an attractive younger woman and his mother watched.

After, a blushing and humiliated Trent sat on the examination table, one slender arm draped protectively across his bust while his mind reeled from the feeling of having someone feel him up. A group of women—his mother, the doctor and the doctor’s assistant, were discussing his blossoming breasts. They were talking about him like he wasn’t even in the room.

“The good news,” Dr.  Patel said, “is that Trent’s breasts are perfectly healthy and well- shaped.”

“Well- shaped?” Trent thought, cringing even further.

“Oh, yeah,” Macy, her pretty young assistant chimed in. “Any girl would love to have breasts like Trent’s.”

“That is good news,” Jane, his mother said, playing along. “But, why does my son have a figure like an Only Fans girl?”

“Any girl would love to have his figure,” Macy chimed in, as she’d been told to do.

More cringing.

“Hormonal imbalance,” the doctor said. “Nothing serious. Trent has the hormonal makeup of a girl going through puberty. That’s all.”

“Is that why he cries all the time now?” Jane asked. Macy giggled.

“Mom!” Trent hissed, his voice now stuck in girl mode.

“Crying spells are normal for a—for someone with the hormonal profile of a girl, sweetie,” Dr. Patel said, patting him on the knee.  She then turned back to Trent’s mom. “He’ll need a good cry at least once a week. Have him watch something like A Fault in Our Stars so he can cry himself out, then he’ll be better able to control his emotions.”

“Like that’ll ever happen,” Trent thought, feeling even more cringey at the thought of his friends finding out he watched that girl movie.

“So, what can be done? Can we reverse this?”

“Trent will need to complete puberty before we can look for a solution,” Dr. Patel said. It was completely not true, but she was in on the plan. “Once his body has fully developed into that of a female, we can look at solutions.”

“How long will that take?” Trent asked, hoping for a quick solution.

“Not long,” Dr. Patel said.

“Thank God,” Trent said, smiling for the first time since his ordeal had begun.

Then, Dr. Patel added, “a few years.”

“Years?! I can’t stay like this for a few years!” Trent squealed, gesturing at his curvy body.

“Now, now,” Jane said. “Don’t throw a hissy.”

“You’ll also need to start wearing a support garment,” Dr. Patel said.

“A support garment?” Trent asked.

“This a type of clothing that will provide your chest with support.”

“Support? My chest?” Trent’s mouth fell open as he began to realize what the doctor was talking about. “You don’t mean--  a bra?”

Macy snickered again, which she’d been told to do, but she also found the idea of a guy having to wear a bra funny.

“I was trying to be sensitive, but yes. You’ll need a bra.”

“Never!” Trent said, slitting his eyes.

When they got home, Sandy couldn’t resist. “What did your gynecologist say, sis?”

“Shut up,” Trent said, too humiliated to even really fight back. He sulked off to his room, reeling from what he’d just heard and experienced.

Part 2

Trent refused to wear a bra. There was just no way. Bras were for girls. More, he loved the sight of a bra, filled out by a female or not. There were few things he loved more than the sight of a bra.  They really turned him on—even a plain black sports bra got him going. The idea of wearing one felt like the ultimate negation of his identity as a boy. Yeah, he had his own tits, but that had been something that happened to him. He had no control. He did have control over whether he started wearing girl shit to “support” his tits.

Confronted with the idea that he was going to have to live like this for years, he had crawled into bed and pulled the covers over his head, curling up and trying to ignore how wrong his body felt, crying, sleeping, crying some more.

His mother told him he would need to see a therapist, and so Trent found himself at the offices of Dr. Webster, who had a cottage industry going turning bad boys into good girls. “Have you ever worn a bra?” Dr. Webster asked the surly teen sitting across from her. He had his slender arms crossed over his chest. “Maybe you would like it?”

“Look, I’m never wearing a bra,” Trent said, concentrating to keep his voice low. “Guys don’t wear bras.”

Dr. Webster knew there was no talking Trent into putting on a bra. It was too great a violation of his sense of self, especially threatening given the way his body was betraying him. “Okay. You don’t have to wear a bra,” Dr. Webster said.

“Wait. Really?” Trent said. For the past two days, his mother had been haranguing him endlessly about his need for support, trying to minimize stretch marks. He’d thought about going to live with his father to get away from her, but he was too ashamed of his feminized body. For the first time in his life, he was glad his father had abandoned him.

“Let’s focus, instead, on seeing what we can do to limit those crying spells you’ve been having. How does that sound?”

“That sounds great,” Trent said, encouraged. Finally, someone was on his side.

Dr. Webster pulled out a gold watch on a chain. “Have you ever been hypnotized?”

Soon, Trent found himself in a hypnotic state. “Women’s underwear is sexy,” Dr. Webster said, and Trent nodded. “It’s pretty and fun. The materials are soft and comfortable. Tell me you agree.”

“I agree,” Trent said in his girl voice, which it wasn’t a super leap because he agreed with some of it, especially the sexy part.

“Men’s underwear is boring. It doesn’t fit. The feeling of men’s underwear hurts. It pinches. You’re shaped like a girl. It makes sense for you to wear girl’s underwear. Tell me you agree.”

Trent’s face crunched up. He fought, but the doctor made so much sense. He was shaped like a girl now. “I—I agree.”

“When you wear girl’s panties you feel confident, sexy, fun. When you wear boys’ underwear you feel ugly and ashamed. Tell me you agree.”

Once more, Trent’s face crunched up and he even shook his head no, but then he whispered, “I agree.”

“You hate the feeling of your breasts bouncing around. The way they jiggle. Agree.”

“I agree,” Trent said, and this time, he did.

“You love bras. They look so pretty. You need the support. You need a bra. You want to wear a bra.”

“No,” Trent whispered. “Never.”

Dr. Webster nodded. It would be hard, but she knew how to make this work. She would need a baby step.  “You find the feeling of your breasts jiggling and bouncing annoying. You envy the fact girls get to wear bras. You envy the support. You wish you could wear a bra, too, so your breast didn’t jiggle and bounce.”

“I—agree,” Trent said, struggling to fight the suggestion but losing because he did wish his breasts didn’t bounce so much. Even when he wrapped them in a bandage, he could feel them jiggling.

The doctor continued. “You should not feel shame at your figure. You didn’t choose to look like a girl.”

“Agreed.”

“You actually think it’s kind of funny you have a hotter body than most of the girls at your school.”

Trent shook his head. He didn’t want to think that. Didn’t want to think of this soft, bouncy body of his as anything but awful. “No.”

Dr. Webster decided to change tactics, slip on more little change into Trent’s mind. “When you check out girls, you’ll compare their breast size to yours. You’ll feel jealous of girls with bigger breasts.”

“Um… … oh, I agree.”

The next morning Trent opened his underwear drawer and tilted his head to the side. What he saw looked like a bunch of briefs, but shorter and all in pastel colors. He picked up a pair and saw that along the waistband they read “Girl Boxers.” He almost threw them across the room like he might catch cooties, but then a few surprising thoughts passed through his brain. “I have a girl’s figure now,” he thought. “I really should wear underwear shaped for my body.”

He stepped into the Girl Boxers, which were so close to men’s shorts as to be as non-threatening as possible. The material was cool and soft, and it felt good against his soft skin.  He looked in the mirror, turned to the side, thinking the shorts looked good. They made him feel pretty, sexy and fun. He felt confident. Plus, it kind of amused him to think he’d be walking around school wearing girl’s underwear and no one would even know. Trent didn’t realize it, but from that moment on he would never wear anything other than panties.

He'd worn one of his old t-shirts to bed which strained across his breasts, and as he stood admiring his profile, he thrust his hips back and arched his back, smiling as a new thought crossed his mind as he admired his curves. “That’s funny,” he thought. “I’ve got a hotter body than Wendy. She’d be so totally jealous of my ass.” Dr. Webster would have been quite pleased to know her suggestion had landed after all.

Having taken his first big step into crossdressing, he wrapped an ace bandage around his chest before putting on a super tight t-shirt under another t-shirt in an effort to flatten down his chest and hide his bust. He may have come to the point in private where he felt a little bit amused and even proud of his new, curvy body, but he had no desire to strut this stuff all over campus.  Yet.

That day as he walked around school, he saw Lindsey Wallace walking along in a tank top with her bra straps showing against her tan shoulders. The straps read Jockey.  “She’s so lucky,” he thought as he admired the way the bra lifted and supported her breasts. Plus, it looked so sexy and fun. “I wish I could wear a bra,” he thought, not even thinking the notion odd. He imagined what it would feel like to wear a bra, to feel the straps across his shoulders, the cups holding his soft, sensitive chest. Then his eyes dropped to her chest, and as much as the old him admired her abundant cleavage, another part of him felt a stab of jealousy that she was so much better endowed than him. “Unh,” he thought, crinkling his nose. “She thinks she’s hot.”

Part 3

Dr. Webster’s plans for Trent then took a slight turn as he suffered what Bob Ross might call a “happy accident.”  While playing doubles tennis, he got hit in the face, breaking his nose.  He would need surgery to repair the damage. As he waited at the doctor’s office, he was his mother and Sandy whispering with the doctor, and his mother showed the doctor a picture on her phone.

“What the hell are they gossiping about?” Trent wondered. He would find out soon enough.

After the surgery, Trent spent a week with bandages around his whole face, not understanding with his jaw and lips ached so much. He’d spent the whole week eating through a straw and couldn’t wait to get the bandages off. His mother and sister were there when the doctor unwound the bandages, and as they came off, his sister started to giggle. “You look just like a girl!” she said.

“What are you talking about?” Trent said in his now constant little girl voice.

“Don’t listen to Sandy,” Mom said. “You look very handsome.”

The doctor handed Trent a mirror, he screamed and fainted. The face looking back at him, with the pert, unturned nose, plump lips and small chin, belonged not to him, but to a girl.

Trent’s confidence was shattered. He did everything he did to hide his figure, strapping down his breasts, wearing long, baggy shirts to try and hide his slender waist and wide, round hips, but he couldn’t totally hide his face. The other kids smirked at him, talked about him. The girls were the worst, especially his ex-girlfriend, Wendy. She and the others would sneak up behind him and pinch or slap his ass. They couldn’t resist as the sight of a boy with such a juicy caboose drove them crazy and, besides, he would always jump and make a little squeaky noise, which was just too much.

Wendy nicknamed him “Pucker” after his big, soft kissable lips. Some of the other girls called him Cutey Commando because they said he sounded like the cartoon character.

The worst part was that he did sound like some anime girl.

With his pretty face, strangers assumed he was a girl. Baristas at the coffee shop called him “miss.” He didn’t bother to correct them, thinking of how ridiculous it would sound for him to try and explain with his little girl voice that he was actually a guy. He went to buy a pair of shoes, and the clerk led him right into the women’s department. Guys kept checking him out, talking about his ass. His life became more and more that of a female, and he hated it. Then, he got pulled over for running a stop sign. As the cop approached, he burst into tears. Rolling down his window, he gushed, “I’m so sorry, officer I didn’t even see—”

“Hey, there little lady,” the cop said. “Now, no need to cry. Just calm down.” He handed Trent a tissue and Trent dabbed his eyes. “I’m not going to give you a ticket darling. Just promise me you’ll be more careful. I’d hate to see a pretty little girl like you get hurt.”

Trent had looked up at the officer and smiled brightly. “Thanks, officer,” he said, relieved. As he drove away, he’d thought—finally, it paid to look like a girl!

He kept losing strength, especially from his upper body, dropping down from doing curls with 50-pound dumbbells down to puny little 10 pounders. Meanwhile, his breasts just kept getting bigger, heavier and harder to hide. His big, bouncy booty, at least, had stopped growing fatter, which was some consolation, though it was so big it jiggled when he walked and was a constant source of shame.

The time came when Sandy felt it was about time to even further knock her brother down and make him recognize he’d been returned to the second-tier status where he belonged. She found him sitting in the living room, watching A Fault in Our Stars. Despite initially refusing, after one of his sessions with the shrink he’d come home and just put it on without thinking. As predicted, it had brought on a Level 5 hurricane of tears, and after he’d felt so much relief, and it really had helped him control his crying. So, from that day on, Trent realized that sometimes he just needed a good cry.

“Wanna play some tennis?”

“Sure. Right after this is over,” Trent said, sitting curled up in a corner of the couch, clutching a pillow to his chest.

“Are you going to cry again?” Sandy said. “Like a little girl?”

“Shut up,” Trent said. It had become a regular thing for his sister to tease him about looking and acting like a girl. It annoyed him, but he’d just gotten used to it.

“I’ll never understand why some girls love to cry,” Sandy said as she went off to get ready.

Trent cried and cried at the end of the movie, then wiped his tears, feeling refreshed. It was time for him to put his annoying little sister in her place. He was way better at tennis than her.

Trent strapped down his boobs and got into his old tennis clothes. They were too big and too small at the same time, but they would do. “How about a bet?” Sandy asked, enjoying the way Trent’s legs had taken on the rounded shape of a girl’s legs, his arms had gotten slender and lithe.

“Sure,” Trent said, smirking. Since his growth spurt, he’d dominated his sister in tennis, and he was deep enough in denial not to even consider the possibility she might beat him. “What’s the bet?”

“You first.”

“If I win, you have to do my chores for a week.”

“If I win, you have to get a makeover.”

“A makeover? You mean, like—”

“Hair, makeup, nails—everything.”

“You’re a freak,” Trent said, shaking his head, but then he said, “You’re on.” He wasn’t going to lose anyway, so what difference did it make?

The two lined up. Sandy loved the way Trent looked. He’d worn his old clothes, and his sweatpants now strained across his big, bouncy butt and wide, round hips. She knew he was wearing an old pair of his sweatpants, but they looked more like girl’s leggings stretched over his new curves. He’d flattened his chest, but even so she could see the swell, and his tiny little arms sticking out from his old shirt were so cute.

Sandy tossed the ball in the air and delivered her serve. She had a good serve, but Trent confidently stepped up and swung, expecting to easily bat the ball back as he’d done a hundred times, but instead the racket twisted in his hand and the ball crashed into the net. Sandy saw the surprise on Trent’s pretty face. But then, he shook it off, thinking it was just a fluke. They kept playing. Trent soon discovered that in addition to having lost so much strength, he had lost a sense of how to move and react in this body with his wide hips and plump ass. He stumbled and fell down, missed easy shots, distracted even by the high-pitched squeaks he made when he hit the ball.

Sandy kept laughing and taunting him as he lost game after game. “Eeee! Eeee!” She started to shout, mocking his little squeaks. “You play like a girl, Cutey Commando” she shouted after he lunged at a ball and fell on his side, his round hip in the air.

To make matters worse, some of the girls from school, including Wendy, showed up, and they stood and watched, laughing as Trent’s sister dominated him. “Omigod, he plays like a girl! My little sister could kick his ass!”

Trent grew more and more enraged, and he was glad he’d had his cry because he could feel the stinging of tears behind his eyes. It was all wrong. He’d outgrown his sister, become bigger and stronger. How could things have gone back to when he was a little boy? It was terrible, and it was about to get worse.

Trent tossed the ball high in the air, and when he brought his racket over his head to serve, he felt the clips come lose on his bandage, which slipped off, his breasts bouncing free as he finished his serve. He squealed, and Sandy saw Trent’s shirt suddenly fill out, saw his boobs bouncing as he ran across the court to try and get the ball she’d hit back. Awkward, off balance, he completely missed the ball, spinning in a circle, his racket hitting nothing but air. He blushed and wrapped one arm across the breasts, which now strained against the front of his shirt.

“Omigod,” he heard Wendy shout. “Trent has tits?” The girls from school all laughed, while Trent wished he could just shrink into the ground. His secret was out. “Well, I’m not surprised,” another girl said. “I mean, with that ass?” Of course, the girls all pulled out their phones and started snapping pictures.

“Um, I need a break?” Trent said, looking around desperately for a place to hide.

“Why?” Sandy asked, pretending she didn’t notice.

“My—you know,” Trent said, glancing down at his chest.

“Oh,” Sandy said. “Your boobs. Okay, I guess, though I never heard of a boy wanting a time out so he could adjust his boobies.”

“Shut up,” Trent said. He pulled the bandage from under his shirt, then began looking around. He couldn’t find the clip. “We’ll have to finish up another time,” he finally said. “I can’t find the clip for my—um—”

“Bra?”

“It’s not a bra!”

“Well, you know the rules. You quit; I win.”

“I’m not quitting,” Trent said, stomping one foot, his breasts bouncing.

“You quit; I win,” Sandy repeated.  “It’s okay, Cutey. A girl can’t play tennis without her bra.”

Trent frowned. He couldn’t let her win. Not now, and not even with Wendy and the others filming him. “Let’s finish this.”

The sight of Trent running around the court, his breasts bouncing furiously, made Sandy laugh, and when the match ended, he looked devastated. He wasn’t even thinking about the makeover he’d agreed to, but instead how his sister had humiliated him, and how much his breasts ached, what was going to happen once the pics hit social media. His life was over. Over!

 To be continued...