Big Sister's Feminization Program (Patreon)

A $25 reward for an anonymous patron. Enjoy!

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Josh excitedly arrived home, his heart skipping a beat. For the longest time he’d had a crush on Sandy Jenkins from 2nd period Math, and he’d finally found the courage to ask her on a date. She’d happily agreed, and he eagerly looked forward to tomorrow, when they’d take a trip to the movies and hopefully cement their young love.

Josh went to enter his bedroom, but recoiled as he found a familiar face sitting atop his bed.

"Hi little bro!" said his older sister Kat, the dark-haired bully wearing a devious grin. Though the siblings had once been close, his sister had begun to morph into a militant feminist over the years, and now regarded her brother as little more than another member of the oppressive sex.

“K-Kat!” he squeaked out. “You’re supposed to be at college!” 

"Didn't mom tell you? She’s going on a business trip for a few days and put me in charge of watching the house.”

“O-oh…” he murmured his understanding. “Well fine, but get out of my room!”

“Why, so you can jerk off?” She asked.

“No way!”

“Oh no? Are you sure? Because I figured you’d be excited to watch these little home movies you’ve been making.” Josh then noticed she was holding his laptop, and she spun it around to show him what she’d found. It was a video from a secret camera hidden in the girl’s locker room, showing his female classmates undressing and showering. 

“G-give me that!” he demanded, lurching forward to try and grab the laptop. The much bigger girl reached out and slapped Josh hard, the boy stunned by the sudden blow.

“You’re sick” she declared. “You know, some of those girls look underage. If this got into the wrong hands you wouldn’t just be expelled, you might even go to jail.” The reality of the situation hit him.

"Please Kat, I’ll do whatever you say!” Josh pleaded.

“That’s the right attitude” she remarked with a smirk. “Luckily, I’ve been planning an experiment for one of my classes, to try and condition men to accept that women are the superior sex. You’re going to be my first test subject!” Josh watched helplessly as his cruel sister opened the suitcase beside her, pulling out a pink, frilly dress.

“This is a dress for little girls” she told him. “Isn’t it so soft and pretty?”

“Y-yes…” Josh agreed, nervously.

“Wrong!” She announced, slapping him. Josh whimpered. “This is a tool of the patriarchy, an attempt to reduce women to frilly, helpless slaves. In the future, this sort of ridiculous costume will only be worn by men, to reinforce their position as the weaker gender.” She grinned again, looking her brother over. “Aren’t you happy to know how progressive you’ll be wearing it?”

“Y-yes…” he whimpered, knowing any other answer would result in more torment. Within minutes he was indeed trapped in the ridiculous pink dress, blushing deeply as he felt the silky fabric against his skin. It actually felt kind of nice… though he would never admit it. Especially how the delicate frills swished around his crotch region.

“Are you getting a boner!?” Kat shrieked angrily, grabbing hold of his semi-erect penis and squeezing it painfully tight.

“Owie!” He cried out. “I’m not, I’m not!”

“Liar!” she slapped him hard, still gripping his penis. “How disgusting. In the future, male pigs like you will be kept in full-time chastity to keep those filthy things under control.” Josh blinked away tears as she pinched his organ mercilessly, before finally relenting. “Lucky for you, I don’t have a chastity cage small enough for you.” Josh felt a small twinge of relief. “But! That doesn’t mean I can’t suppress that dirty thing with another surprise…” she again went to the suitcase, and quickly returned with a soft, crinkly pink garment. Josh’s eyes went wide.

“Please sis! Not a diaper!”

“Quiet!” she yelled, pushing him down onto the bed and throwing up his skirt. “To truly accept female superiority, you must be reduced to the status of an infant, before having your mind built-back up with the proper conditioning!” Josh moaned as he felt the thick, humiliating diaper pulled between his legs, listening as the heavy duty tapes were pulled into place. From out of the suitcase came a pair of thick rubber pants, with a chain around the waistband. “And this will ensure you can get your hands on that pathetic twig between your legs, and that whatever you might fill that diaper with stays properly contained.”

“No no no…” he whimpered softly, truly helpless as the soft cottony diaper was wrapped in the pink rubber covering.

“And finally! Your feminizing formula!” Kat announced, pulling out a thick baby bottle of formula and pushing the nipple deep into her little brother’s mouth. “Swallow that milk, unless you want to suffer the consequences!” she demanded. Josh obediently nursed from the rubber teat, a sickly sweet milky substance rushing down his throat. “That contains some special drugs I’m experimenting with. Some female hormones to give you a more womanly perspective, some muscle relaxants to make you more receptive to your coming hypnosis sessions, and of course some laxatives to ensure you use your diaper like a good sissy boy.” Hearing all this made Josh truly afraid of his sister, but already the milk was making him too weak and drowsy to resist.

“Josh!?” Josh turned his head, eyes wide as he found Sandy standing in the doorway with a look of disgust on her face.

“S-Sandy!? You aren’t supposed to be here until tomorrow!”

“Quiet!” his sister yelled, forcing the nipple back into his mouth. “You just earned yourself some serious punishment for that outburst!” Josh whimpered, too afraid to do anything but continue suckling. “I can explain” Kat said. “I found those flirty little messages on your instant messenger, so I asked Susie if she’d prefer to move your date to today. Luckily she agreed, and gets to see what a little wimp you are!” Completely humiliated, Josh began to sob, releasing his bladder into the waiting diaper between his legs.

“Oh gross!” Sandy remarked, the scent of piss already apparent. “Well Josh, forget about our date, I don’t date sissy diaper boys!” Kat laughed at this.

“Spoken like a true feminist” she said. “You seem like a very proud young woman.” Kat stood up, putting the bottle in Josh’s hands, making it clear he’d better continue nursing. “Tell you what” Kat began, putting an arm around the pretty redhead’s shoulder. “How about I put little Prissy to bed, and me and you can go enjoy our own little date.” Sandy’s face turned pink, clearly excited at the prospect of being alone with the strong-willed lesbian woman.

Just a few moments later and Josh was strapped into his bed with leather restraints, ready for his early bedtime. “Bye, bye Prissy!” Sandy announced as she and Kat switched off the lights and headed for the door. But Josh had no way of hearing them, the drowsy boy’s ears encased in large headphones, a hypnotic loop of his horrible sister’s voice floating through his head.

“Men are babies. Babies wear diapers. Diapers are for wetting and messing. Use your diaper like a good girl.”

Subconsciously, Josh released another stream of urine into his padding. Soon, he’d be a true feminist, just like his sister.