Stop Teasing Your Sister 2 Part C (Patreon)

For story with images, see PDF below.

Trent lay on his back, watching his breasts rise and fall with each breath. Occasionally, he shook his shoulders from side to side so he could watch them sway, or he lifted his hips and dropped them down so he could feel them bounce. Mostly, though, he just liked to watch them rise and fall, to feel their soft weight moving with his breathing. It still didn’t seem possible to him that he had such big breasts, breasts just like the ones he’d admired and drooled over when he looked at the girls at school or surfed the net for porn. Breast were something they had, not him, but, yet, there they were, rising and falling, rising and falling.

A thought that had been implanted by his therapist popped up: I wish I could wear a bra, he thought, feeling a little tweak of jealousy. Girls were so lucky.  He needed support as much as any of them—more even—but boys didn’t wear bras. He would be too ashamed.

He lived in a constant state of agitation now. He loved boobs. He loved looking at them, and he’d fought valiantly when he’d been with his girlfriend to cop a feel every chance he could get. He loved breasts so much that he loved anything that might ever touch a breast— the sight of a bra, a halter top—anything a girl might wear on his body made him crazy.

Now, he had breasts of his own—big ones, and they had a way of constantly reminding him of their presence. They were heavy and gave him back aches. When he strapped them down, he found it hard to breath, and even then he could feel them jiggle. The result was that he was always horny and at the same time confused and ashamed.

It wasn’t just his jugs, either. Whenever he caught a glimpse of himself in the mirror he saw a girl’s curves,-- a slender waist, round hips, a plump rear. Thanks to the work of his therapist his new shape confused, aroused, amused and ashamed him all at the same time. He hated looking like a girl, he loved looking like a girl. He didn’t even know anymore.

Everyone at school plus about 500,000 people he’d never met had seen video of him running around on the tennis court, his breasts bouncing, with the hashtag nobra as well as others. When horny guys searched the hashstag nobra they were as likely to find a picture or video of Trent now as some hot girl. A lot of the guys were cruel, calling him a sissy or boob boy. He’d gone from being a cool guy to an outcast.

Just like at school, certain girls seemed to revel in the role reversal, and he had been bombarded with IMs from hot girls asking him to send them tit pics.

His life was over.

His sister, Sandy, for her part loved seeing her brother lose all his confidence. He moped around the house in pajama bottoms that stretched across his big butt and a t-shirt that stretched across his bouncy bust. He didn’t even bother to hide his feminized body anymore—not at home, and he barely left the house. He hadn’t gotten his hair cut in weeks and now had what looked like a messy bob that only enhanced his feminine features. He spent most of time lazing on the couch, watching romantic movies, crying.

It was just about time Sandy, her mom and his therapist decided, to start building Trent back up—this time as a girl who only felt confident when she was as feminine as possible.

Trent’s price for losing the bet was that he had to get a makeover. Sandy had timed her humiliation to coincide to the end of the year. There was only a week of school left, and Trent’s Mom had arranged for him to finish his classes online. He didn’t want to leave the house and show his new face to the world, but she insisted he couldn’t back out on his bet.  She, Trent and Sandy had all been sitting in the kitchen discussing it. Trent wore a pair of pajama pants and a t-shirt, the top ballooning out, as he didn’t even bother hiding his breasts at home anymore.

“I’ll do your chores for a week,” Trent said in his squeaky little girl voice.

“Nope. Makeover,” Sandy said, shaking her head.

“A month, then!” Trent said, his tea kettle voice growing more shrill. Sandy had already informed him that his makeover would take place at the mall, and the thought of walking around the mall now made him feel sick with embarrassment.

“Makeover,” Sandy repeated, tossing a French fry into her mouth. “That was the bet.”

“Moooom!” Trent screamed.

Sandy exchanged a conspiratorial glance with her daughter. “Your father always said that a real man never welched on a bet,” she said. ‘But, well, with your hormonal imbalance and all, maybe you aren’t much of a man anymore.”

“Fine,’ Trent said, crossing his slender arms under his heavy breasts. The ploy had worked. Even in his curvy new body—especially in his curvy new body—he hated the thought he was a disappoint to his father, less than a man. “It’s so stupid,” he sneered, pouting. “You’re the worst sister ever.”

You have no idea, Sandy thought. You have no idea. Now that Trent had agreed to the makeover, she got up and headed to her room. She had such plans, and she couldn’t wait to get started on the next phase of her brother’s transformation.

Dr. Webster, meanwhile, continued to work on Trent’s psyche. She’d hypnotized him once again, and he lay back, a dreamy look on his face as she continued his programming.

“Boys pick on you. Make fun of you because you look like a girl.”

“Yes.”

“You’re scared of boys now. They’re bigger and stronger than you.”

“Yes.” So far, although he would have been ashamed to admit it, everything Dr. Webster said was true. This was part of her plan.

“You could fool them. They wouldn’t make fun of you if they thought you were a girl.”

Trent’s face twisted as he struggled against the thought.

“It would show how much smarter you are than them if you fooled them. It would be so funny to pass as a girl and fool them all.”

“Y—yes,” Trent said as the idea took hold.

“Going places along makes you feel scared. You feel safer when you are with someone else—especially your sister. Your sister knows what’s best for you. She’s older and more mature.”

“Y—yes.”

“I am going to make some suggestions now. These ideas will simmer in your subconscious, but they will be activated when you go to the mall with your sister and get your makeover.

“Makeup is your war paint. When you wear it, you feel safe, protected. You like the way it feels and smells. You like the way you look when you wear makeup. Makeup makes you feel safe.”

“Yes.”

“You need to look pretty.”

“Yes.”

“Girl clothes are your armor, and when you wear high-heels you feel powerful, confident. Dressing like a girl makes you feel brave. Passing as a girl makes you feel dominant.”

“Yes.”

“You don’t feel complete without jewelry. It will help you pass as a girl.”

“Yes.”

“You will slowly come to as I count down from 10… 9… 8…”

Trent’s eyes fluttered open. He sat up.

“You did really well today,’ Dr. Webster said, putting her hand on his knee.

“Did I?” Trent asked, brushing his bangs from his eyes. He always woke from the hypnosis sessions with Dr. Webster feeling confused, blurry.

“Are you sure you’re going to be okay getting home on your own?” Dr. Webster asked.

Trent’s eyes went wide and his mouth fell open. His heart raced. “I think so,” he said as a new anxiety gripped him.

Dr. Webster handed Trent a glittery pink tube with a chain attached. “It’s pepper spray,” Dr. Webster said. “In case a boy tries something.”

Trent though the pepper spray looked ridiculous, but he was so scared of boys and didn’t like to go anywhere alone. He clutched the glittery tube to his chest and smiled. “Thank you so much.”

Part Two

Trent crouched next to Sandy, half hiding behind her as the two of them entered the salon.  He’d worn his New Amsterdam Warriors t-shirt, one of his favorites, but the way the word “warriors” was stretched and distorted by his boobs humiliated him. Sandy had forbid him to strap his breasts down as part of his makeover would include bra shopping—and wearing. The thought terrified him. Bras were for girls.

“Hi,” Sandy said to the girl at the desk. “My brother here has an appointment for a full make over.”

The girl laughed. “You’re brother? Right.” Based on the looks on both Sandy and Trent’s faces, she realized her mistake. Trent knew he looked like a girl, but it still shocked and embarrassed him that everyone assumed he was a girl now. Could he blame them, though, with his huge boobs stretching out his shirt?

 “I’m so sorry,” the girl said. “Danny is ready for you.”

Danny? Trent’s heart started to race again. Boys made him nervous and having a boy give him a makeover? He’ll make fun of me, Trent thought. Call me—

“Hi, guys,” a pretty young girl with red hair said. Trent sighed with relief. He felt more comfortable around women these days.

Sandy put a hand on the small of Trent’s back and guided him to the stylist’ chair. His face was bright red as he sat, and Sandy and the stylist talked about what she wanted done. He was just a spectator to his own pending feminization, but it was probably better, he thought. Sandy was older, more mature. He trusted her. Besides, once this humiliating makeover was done, he would go straight home and undo everything, so all he had to do was get through this so he wouldn’t disappoint his father.

Danny tied Trent’s hair back. Looking in the mirror, Trent cringed at the thought of what he would look like wearing makeup. He already looked like a girl, and he was sure the makeup would only make that worse, but it was more what the other kids would think of him if they saw him wearing makeup. They would think he wanted to be a girl.

He closed his eyes as Danny began to brush eyeshadow over his eyelids. She and Sandy chatted as she worked, and Trent sat just focusing on his breathing and staying calm, wanting this all to be over and—hmmmm. The makeup actually smelled pretty good, and as Danny worked he realized it felt good—especially the smooth, creamy lipstick she brushed over his lips.

“Okay, honey. You can look now.”

Trent opened his eyes and squeaked. He looked—pretty. Prettier. Feminine. Danny had, at Sandy’s direction, painted his face with pinks and powder blues. Everything that had looked female about his face now looked even more so from his plump lips to his big eyes, now framed by long, curly lashes almost dripping with mascara. He felt like what little of him that had been left had been erased.

For a second, white hot rage rose in him, and he almost got up and punched Sandy for doing this to him, but then he blinked as Dr. Webster’s conditioning kicked in. He tilted his head to the side, turned it right and left. He batted his long, sexy lashes, and a smile spread across his lovely face. “Is it weird that I kind of like it?”

“Not at all,” Sandy said. “You look pretty.”

“So pretty,” Danny agreed.

Pretty. Yes. Trent liked being pretty. He needed to look pretty. He shrugged and giggled, not sure what was happening to him. “What’s next?”

Trent watched as the girl pierced his ears. Sandy held up a pair of heart-shaped earrings. “Tell me you don’t love these.”

“I don’t love them,” Trent said, giving her the stink eye, though part of him was churning them over in his mind. They certainly weren’t anything a boy would usually wear, and he was starting to think that as long as he was walking around the mall after his makeover, he should probably just pretend he was a girl. No one would make fun of him then. Maybe he would ask Sandy what she thought.

Danny pierced his ears. It didn’t really hurt all that much. Then, she pulled a long, wavy blonde wig out of a box. The wig was long, big. “Does it have to be so long?” Trent asked, wondering how he would manage with all that hair.

“Yes,” Sandy said, laughing. “You need to find out what it’s like for a girl to have long hair like that. It’s a lot of work.”

“Fine,” Trent pouted, though he had every intention of yanking the wig off as soon as he got home.

Danny went to work, pulling some of Trent’s hair through the wig, affixing it to his head. “You could walk through a hurricane and your hair won’t fly off,” Danny said as she finished, mussing the golden hair that now framed his pretty face.

Trent had always loved women with long, sexy hair. He’d pressured his last girlfriend, Wendy, to grow her hair out over her objections, and when she’d complained at how much work it was to have long hair he’d just laughed at her. Now, at least for a few hours, he would have long, gorgeous hair. Well, he thought, at least it makes me look less like a boy.

Finally, Danny pressed pink nail extensions over his nails. Trent held up his hands, looking at the way his long, pink nails glittered in the light. He liked glittery, sparkly things.

“Omigod. You’re gorgeous,” Sandy said as Trent stood up. “You look just like a model. Hey, everyone. Isn’t my brother the prettiest thing you’ve ever seen?”

“Sandy!” Trent hissed, but the women at the salon, thinking Trent had come to get the makeover on purpose, applauded. “You’d never think she was a boy!” An older woman said, mixing up her pronouns.

Sandy took Trent’s arm and dragged him back out into the mall. “Time for a new outfit,” she proclaimed. “The first thing we need to do is get you fitted for a bra.”

Trent winced. He knew it was coming. He’d been fighting it for weeks, but the truth was he was jealous that girls got to wear bras. He needed the support. Still, he stopped. “Sandy,” he said, making his sweet, please do me a favor face. “Is there any way, pretty please, we can just pretend I’m a girl for the rest of the makeover?”

“Wait,” Sandy said, pretending to be surprised. “You want to pretend to be a girl?”

“Yeah?” Trent said, crinkling his nose. “I just, well, I think it would be a little less embarrassing?”

Sandy cupped Trent’s smooth cheek. “Anything for my little sister.”

Soon, Sandy introduced her brother to a salesgirl at Victorian Closet. “My sister, Tabitha,” she said, “recently blossomed, and she needs to be fitted for a bra.”

“Of course,” the girl said. Soon, a blushing Trent found himself holding his arms up as the girl wrapped a tape measure first over his breasts and then just under them. “You’re a C cup,” she said. “Lucky girl.”

“I know, right?” Trent giggled, thinking if he was a girl he’d be proud of his big breasts.

Once they knew his bra size, Sandy picked out a push-up bra for him to try on and went into the changing room with him. Trent pulled his shirt up over his head, but it got tangled in his long hair. Sandy helped him get it off, glancing at her brother in the mirror, enjoying the sight of his firm, perky breasts bouncing in the mirror. Then, she slipped him into his first bra, hooking it in the back, then coming around the front, adjusting the straps. Trent’s breasts were plenty perky, but the bra lifted them even more and presented them to the world like a delicious desert.

 Trent slouched over, burning with shame to find himself wearing a bra, getting helped into it by his sister.

“Stand up straight,” Sandy commanded. “Shoulders back, chest out.” Trent complied. “Now, how do you feel?”

Trent looked at the busty blonde girl in the mirror, the slender straps over his little shoulders, the cups pressing her breasts together to create a shadowy valley of enticing cleavage. Sandy and her mom had been gradually making his girl boxers smaller, and had then replaced them with Tanga shorts, so he was totally wearing girl’s underwear now, and not some girl’s version of guy underwear, either. Having his sister see him wearing lacy panties was even more humiliating than the bra, so he hunched over and tried to cover his panties.

“Do I have to wear a bra?” He said, a slight whine to his tea kettle voice.

“You need the support, sweetie and, besides, it will make you look more like a girl so no mean boys will pick on you.”

That was true, and it gave Trent some sense of relief. Plus, he was glad Sandy wasn’t teasing him about his bra and panties. He turned to the side, lifted his hands to his bra and felt the cool, silky material. “I do need the support,” he admitted. “Oh, I suppose I’ll get used to it.”

Sandy smiled. You bet you will, she thought. “Let’s pick out some more bras for you,” she said. “You need more colors and at least a few more styles.”

“Why?”

“I’ll explain as we shop.”

The shopping makeover was a whirlwind, and soon a very bashful Trent found himself walking through the mall in a miniskirt, a vest with a plunging neckline that left not only his boobs visible but even the top of his bra. He had a pink purse tucked under his arm and was hobbling along on cork-wedge sandals. Guys looked him over, letting their eyes linger on his tits, even old guys like his Dad’s age were looking him up and down, which was so gross. Half of them craned their necks around to get a look at his ass as they passed. He felt totally exposed, and it mortified him that his outfit now celebrated every embarrassing thing about his body from his tiny little arms to his slender waist to his plump, bouncy butt and boobs.

“Can’t we just go home?” He whispered as he walked along, his long golden hair bouncing prettily with each step.

“I’m starving,” Sandy said. “We’ll go by the food court and grab salads. Then we can head home.”

“I can’t wait to get out of this skirt,” Trent said. “It’s so tight I can barely walk.” It was true. He’d never felt so limited and controlled by his clothes before, and yet for reasons he couldn’t understand, somehow he felt safer dressed like this, more confident.

Sandy led him to Salad House. She ordered for both of them. Then, she almost died laughing when they got to the table. Trent put his purse down, then started to sit, stopped, started again. He’d never sat down in a mini-skirt before, and when he finally gave it a try he almost fell onto his chair. His skirt had ridden up his legs and he tugged it down, terrified people would see his panties.

“You’ll need to work on how to sit when you’re wearing a skirt or a dress,” Sandy said, smiling.

“Um, I am not going to be wearing skirts and dresses,” Trent said as he started to nibble on his salad.

“We’ll see.”

He never saw Wendy walking up behind him, making eye contact with Sandy, who smirked. Wendt walked around the table so she was facing both Trent and Sandy. “Hey, girls,” she sang out.

Trent squeaked, instantly super self-conscious about his outfit. This was his former girlfriend, and he felt naked now, ridiculous with his breasts swelling out from the top of his vest, his long legs exposed by his tiny little shirt. He felt hyper-conscious not only of the tight women’s clothes that showed off his soft curves, but his whole soft, bouncy feminized body. He looked away. “Sandy,” Wendy said. “Who is your pretty friend? She looks like a model.”

Trent, trying to hide behind the curtain of the long golden hair framing his face, glanced at Sandy and mouthed, please with his pink frosted lips.

“That’s my cousin Tabitha,” Sandy said. “She visiting from, um, Trenton. Tabitha, this is my friend Wendy.”

She won’t recognize me, Trent thought. She can’t. I don’t even recognize me. Still averting his gaze, he raised his hand, which Wendy took his fingertips and squeezed in the girliest handshake ever. Then, she took Trent’s soft hand and held it in her palm. “Your nails look great,” she said.

“Thanks,” Trent whispered thinking, at least there’s not a chance in hell she’ll recognize my voice.

Wendy kept holding his hand, then reached down and brushed his hair away from his cheek, letting her hand rest on his smooth, hairless cheek. She cupped his chin. “Let me get a look at you,” she said, turning his face so he was now looking up at her. “I want to just kiss you to heaven, and I’m straight. Wow. Say, are you sure we’ve never met? You look familiar?”

Trent felt himself panicking, his heart racing. No. No. No. He couldn’t have his ex see him like this. She would tell the whole school. “I don’t think so,” he said. “I mean, I’ve never been here before so—”

“Omigod!” Wendy shouted, pretending as if she’d just recognized him. “Trent!”