The Long Path to Feminization

Editor's note: this story contains scenes of incest or incest content.

*****

It started off inconspicuously enough.

He was your best friend since at least the end of high school - or at least, you suspect that's the case. It became so hard to remember sometimes.

And one day after class, out of the blue, he introduced you to hypnosis. You accepted his offer.

Your first session with him was remarkable. It felt amazing. So relaxing, so calm, so cozy and content.

It became a regular part of your routine. To go visit him, to enjoy your daily trance after school, before heading home for the day. With time, it'd even feel unsettling whenever those rare occasions sprung up where one of you would miss a day.

Then, one day, you had an incredible, brilliant idea that was totally your own, and most certainly not a suggestion fed to your mind by somebody else.

You proposed that he come home and offer a hypnotic session to your mother.

You were her only son, and she was a single mom. And hypnosis simply felt so amazing. It would be borderline criminal to not let others experience it too.

He sat her down, explained what it was, and got to work with his words. It felt so nice to watch her slip into trance. Her eyelids growing heavy and limp. The corners of her lips curling up in a cozy little smile. Just watching it happen to her proved to be contagious.

When he awoke the both of you, you felt renewed. Refreshed. Mommy was behaving a little different, too. You couldn't quite put your finger on it, but he suggested that he come over again tomorrow evening. Neither of you could accept the offer fast enough.

As they days went on, Mommy seemed to develop a new set of mannerisms. She started assigning you more chores around the household - and you accepted them without much thought or hesitation. Cooking. Cleaning. Helping with the laundry. You didn't mind it in the least. It felt so fulfilling to do what you were told.

As the last school year drew to a close, you noticed a few changes in yourself. Progressive differences in your mannerisms. That one cute girl you spent your morning English class admiring didn't interest you so much anymore. Your nightly routine of browsing your favorite porn sites on your laptop didn't inspire the same feelings. You found yourself content with being passive. Docile. Gradually, you found that obeying Mommy's orders proved to feel much more fulfilling. And in class, your eyes found themselves wandering towards the cuter boys in the front rows.

Then it happened.

The morning after an especially deep and powerful session the night before with your besty. You bolted out of bed, just before your morning alarm went off, and you realized something:

You'd never be comfortable being masculine. You couldn't ever live with yourself pretending to be a real man.

You wanted to be a pretty girl.

And it was completely your own idea, too. No doubt about it. Absolutely your own, and totally not because somebody else had recommended or suggested it.

You broke the news to Mommy, and she was overjoyed to hear it. It was almost as though she was expecting to hear it from you. You were both so eager to share the news with your best friend, which happened soon enough, considering that he now spent more time at your house with every passing day. When you told him of your resolution, he seemed happy, but not surprised. He politely suggested that - since school was nearly over - Mommy should start introducing you to the world of female. There was plenty of enthusiastic talk between you two over it: teaching you how to do your hair, your nails, your makeup. Even going out clothes shopping. Pretty pink dresses and hairbands and stockings and heels. It was all so exciting.

Mommy was willing to do whatever it took for her beautiful daughter.

Graduation came, and with it, all the free time you two needed to indulge completely. A mother and her brand-new daughter. And you made the most of it together. Even the nitty-gritty little things. Hygiene. Keeping your feminine body shaven silky smooth.

Your eighteenth birthday came, and you decided you'd want a more private celebration, at least during the start of your transition. Just Mommy and your besty.

That's when Mommy gave you the very best birthday present you could ever hope to ask for.

Mommy presented you with a certificate for hormones replacement therapy.

Mommy was willing to do anything for her perfect little daughter.

Oh, you were so overjoyed. You wanted to run straight to the clinic to get started right away.

With the treatment that began over the summer, your body slowly began its change. You stopped growing taller. You remained pretty and petite. Your hips grew wider, your waist remained thin. Your voice stayed high pitched, and your wrists remained tiny. With every passing day, you grew more and more proud of how round and pretty your face was becoming. At the recommendation of your best friend, you had adopted a morning workout routine - squats to make your tush nice and toned, sit-ups to keep your tummy modest. Your breasts even started growing in - extremely tender and sensitive at first, but Mommy assured you that soon enough, they'd develop in full. And they'd be so beautiful.

But with these hormones came needs. Just as any teenager might experience.

It happened one day, your first day of community college. A fresh start. Not one person so much as questioned whether you were female or not - it just seemed obvious. It felt reassuring. It felt like a new beginning.

Your eyes happened to fall upon a particularly tall and handsome young man walking the other way down the halls. You started feeling the tingles, the stirrings. You felt drawn towards him. You felt the all-familiar stiffness under your skirt.

And it was so shameful.

With great difficulty, you managed to hide it and make your way to the lady's room. Eventually, your calmed down. But it all felt so unladylike.

When you came home, you confessed the incident to your besty. He only nodded and made his way to your mother's bedroom to have a private conversation with her. When they were finished, she promptly strolled over to you with that mischievous smirk of hers and produced her diamond pendulum. You remember her soothing voice, her gentle whispers, her body pressed against yours...

...and you remember the conversation you had with her. That good girls don't get hard. Good girls don't penetrate others. Good girls are penetrated. No more ladyboners. No more masturbating that little cocklet, soften and shrunken from the hormones.

And then you remember that beautiful gift she gave you: a pretty, pink chastity cage, secured with a silver heart shaped padlock.

You remember her slipping it onto you. You remember her staring deeply into your eyes. And you remember hearing the soft *click* of the pretty, silver, heart-shaped padlock closing shut.

And it felt amazing.

You're a good girl.

And Mommy would absolutely do anything for her pretty little daughter.

Each passing day, your besty reinforced the behavior associated with chastity. Training your mind to keep your clitty soft and limp. You began to feel so secure when wearing your cage. So cozy and content. So obedient and pure. Such a good girl. And when it was removed, it brought upon you a creeping fidgety feeling. Squirmy. Anxious. Second guessing yourself.

But the moment it was slipped on again...

Bliss~

But a girl still has needs. Class was in full swing, and there was still the problem of boys.

You remember conversations in the hallway. Making new friends, new acquaintances. Some of them male. Some of them really cute.

You had a hard time keeping yourself collected through trembling legs and blushing cheeks. It was only after your third conversation that you realized your girly clitty had been leaking precum, drooling it out from under your skirt. When you checked the hallways behind you, you noticed a small clear puddle on the floor, right where you had been standing, squarely between the spot where your ankles had been.

You still remember how scorched your cheeks felt.

When you came home from class that day, you realized you had to do something about this. There had to be some remedy for your sexual tensions. Girls had needs. It was only normal. But poor little you didn't know what to do.

That night, you confessed your dilemma to your best friend. He was supportive and understanding - as usually - and offered a remedy through hypnosis. He entranced you before you went to sleep, as was his special little routine with you. That night, you found yourself have warm, cozy dreams. Vivid fantasies of hot studs, cute boys.

When you woke up on that bright and beautiful Saturday morning, Mommy was sitting at the edge of your bed.

She told you it was about time that you learned the sissy girl version of the birds and the bees. Good girls didn't penetrate others. Good girls were penetrated. And it was time that you learned that message in full.

She taught you everything. Enemas. Cleaning. Lube. Caring for your pretty girl-hole. And she gave you gifts. Toys of all sorts. But most important of all, a pretty, silver little plug, with a bright pink gem at its base.

Mommy would do whatever she needed for her beautiful daughter.

It was amazing.

When it was slipped inside of you for the first time, it kept you just stimulated enough. Just a little nudge or stroke with every step, every sway of your feminine hips. Not ever quite enough to keep you satisfied, but just enough to keep you calm and collected in your everyday life.

And for a while, it did the trick.

But girls still have needs.

After barely making it through the next Monday of school without going completely boy crazy, you rushed home and clamored up the stairs to your room. You used everything that Mommy had taught you and masturbated your pretty sissyhole. You played until you were absolutely spent.

But it still left you feeling hollow. It was still lacking something.

And so, you turned to your besty.

Turns out, he was more than happy to help, now that you'd learned a little more about your body.

That first night with him was so fulfilling, so passionate. You remember deep kisses and warm embraces, and the feeling of his long, thick cock deep inside of you. His tip rolling over your prostate over and over, milking you empty. It felt so satisfying. In no time at all, your balls, your sissy ovaries had been drained, leaving you aching from how empty they were.

You were hooked.

With time, it became routine. You'd go off to class with a skip in your step and a bow in your hair, you'd perform well - just as a good girl ought to - and you'd come home for a that wonderful passion you shared with your best friend. Sometimes, you might come home to find him having a little fun with Mommy, but you understood - he made a very convincing argument, after all. Mommy was single. Lonely. Mommy had needs just like you did. And who could blame her, when he was so strong and manly and handsome...

The years went along naturally enough. Your body continued to develop. Your breasts formed into a round, supple bosom. Your pretty dresses started fitting you better. You performed excellently in school. You developed all sorts of close friendships with other girls. You dated a few cute boys, but you never went very far with any of them. And you spent long, sleepless nights pleasuring your besty. With time, you started referring to him as 'Master'. You couldn't explain why - it just felt more natural that way. Besides, Mommy was doing it too.

Then, one day, something rather unexpected happened.

You were in bed, taking Master's cock deep inside of you from behind. You remember his balls slapping against you, you remember him pulling your hair and calling you horrible, naughty names. It was so romantic, and you were so close to climax.

But you couldn't cum.

You were on the brink, locked in that wonderful state of euphoria. Your legs were trembling, threatening to collapse underneath you. Your clitty was drooling precum until your ovaries were aching. You were gasping and moaning, so desperate to feel resolution.

Then finished inside of you. You felt his cum flooding your girl-hole. He was even gracious enough to keep going for a few minutes after finishing. But when he finally stopped, when he pulled his member out of you, all the feelings slowly faded away. It left you feeling so squirmy, so needy. So desperate for satisfaction.

But Master told you otherwise.

He told you that good sissy girls don't feel satisfaction.

Their purpose is in life is to satisfy others.

Things began to change for you, from that moment onwards, as you ventured into your adult life. You began blowjob training with Master, as he brainwashed your gag reflex away. With time, you'd begin to feel a deep psychological contentment when you felt his load hit the back of your throat.

Both Master and Mommy started becoming much more stern with you. Punishment for trivial shortcomings were common. But you grew to adore the feeling of being bent over either of their laps, feeling their palms striking your plush ass. Sometimes, you'd intentionally act like a brat, just so that you might get that helpless thrill of being bent over and spanked.

Mommy started developing hedonistic tendencies. She began abusing her power over you around the house. A new present came - a pretty little French maid uniform. After a while, you grew to expect her to order you into wearing it the moment you came home, before doing your chores, serving her a drink, or - the newest task in your repertoire - pleasuring her.

You remember that first time Mommy issued you that order, Master watching over you from the comfort of his armchair. The urge to obey was so powerful, you didn't even hesitate. You dropped to your knees, just as you'd instinctively learned to do at the sight of Master's cock. Mommy pulled down her panties and leaned back, that mischievous smile on her face. You remember her taste. It was so warm and delicious, so creamy and smooth. You remember her hand on the back of your head, nudging you, guiding you, stroking your hair. It didn't take long before she squirted straight in your face.

Mommy would do anything to her pretty sissy daughter.

Nowadays, performing such acts are pedestrian in comparison with how you're otherwise expected to perform. Occasionally, Master will invite guests over for you to entertain. Sometimes, he'll order you to go out and find other girls for you to bring home for him - new subjects to hypnotize and play with. Sometimes, Master will play with Mommy right in front of you, and order you to lap his cum out of her holes - the chore is a personal favorite of yours, though you wouldn't ever admit it to either of them.

Sometimes, you sit back and reflect upon the drastic changes in your life. The way that Master treats you, the way he lives his life with you and Mommy.

Even if you're largely helpless in the face of the power he has over you, you aren't entirely blind to it. You know how he takes advantage of you, how he misuses you, how he keeps you completely under his thumb.

You're a pretty sissy princess. You're his pretty sissy princess.

And you couldn't be happier with your life.