Under Mommy's Direction Ch. 01

Editor's note: this story contains scenes of sissification and gay male sexual content.

Chapter One

Jaime had never had much luck with the girls in high school. It had come and gone, and now he was enjoying one last summer before heading off to college with his virginity intact. It wasn't his fault really, he wasn't a creep or a douchebag, it's just that life and genetics had left him woefully under equipped for the seduction of the opposite sex. Jaime had never known his father, he had died while he was very young, and he'd lived alone with his mother for all 18 years of his life. He hadn't been neglected or abused, and had always been well provided for, but he never had any sort of male role model, or even close male friends.

His figure on the other hand, had actively worked against him his whole life. Jaime was only 5' 6", and weighed maybe 110 lbs. He was slender and lithe, but had a rear end that had no business being attached to a boy. Finally, his dick was pitiful. He had never had a chance to show it off to a girl but it was only 3 inches when fully erect, and even smaller when soft. Jaime had always been the last one out of the locker room for gym and it was no surprise.

Jaime's Mother, Sandra, pondered over these facts as she sat at her computer, a tall glass of red wine at her left, as she browsed internet advice forums. She knew that college was the best choice for him academically and professionally, but she was worried for his personal life. All throughout high school girls hadn't been interested in him, and she couldn't blame them. She always thought that he was maybe just a late bloomer, but as high school ended and college loomed, she realized that his body was never going to change, he was going to be a skinny little weakling forever.

She didn't want him spending his time at university pointlessly trying to compete with real men, so she searched online for parents in similar situations looking for some way to prepare Jaime. And as the night went on and the wine disappeared she was getting more and more desperate. Too many stories of sons becoming "incels" or joining gangs for a sense of masculinity. It wasn't until she found herself on a sexual advice forum that something piqued her interest, something she'd thought about in the back of her mind for a very long time.

The title of the post read "Sissifying our Son for a Better Future" and was a long and detailed article. The couple's son had always been a "femme little thing" in their opinion, and rather than wait for life to guide him down the proper course, or lead him astray entirely, they had taken matter into their own hands to ensure his happiness. Long family bonding sessions, open therapy, promoting a feminine lifestyle, they had done the work for almost a decade, starting it as soon as he entered puberty and they saw where it was heading. Sandra frowned at this, since she didn't have years, she only had months, but a comment on the article caught her eye.

"Sure it takes years if you want to guide them to the answer, but with sissy hypnos you can turn even the most rebellious boy into a mincing little faggot in a matter of weeks~"

The words mixed with the wine made her heart pound in her chest. They brought up old memories of when she'd first caught him masturbating, and had seen how waifish he looked and how small he was. She'd tried to put that scene out of her mind but it had always come back, more and more perverse for some reason. First she'd imagined him in her panties, then playing with his ass. It wasn't long before she was daydreaming about Jaime in full lingerie pounding his ass with a dildo. It was a sick series of depraved fantasies that had haunted her ever since. She bit her lip and tried to drive the images from her head. This wasn't about her fantasies, it was about Jaime, but maybe it could be about both...

. . .

Jaime was in his bedroom, up late in front of his computer as well. He had his hand fully wrapped around his 3 inch dick as he browsed images of pornstars revealing themselves to him. He'd always stayed away from porn with better endowed men in it for obvious reasons, and so only looked at porn of solo females or lesbians. He was truly getting into a fantasy of this woman inviting him into her bedroom when a sudden knocking at the door sent him scrambling to hide his activities. As his Mother burst in he had only just managed to hide his erection as he clicked away to another tab.

"Jaime dear you can't spend the entire Summer up all night on the computer! Go to bed."

Jaime offered weak resistance as he could tell his Mother had had more than a sip of wine. As she came over to give him a kiss goodnight he could only blush with shame as his erection wilted away. He certainly couldn't have noticed her plugging in a USB drive into his computer, or the odd smirk she had in the pale light of his computer screen.

"Get some sleep, and I'll see you in the morning."

His Mother then turned and left, leaving him to his ruined masturbation session. Frustrated, Jaime obliged his Mother, but not before turning on a podcast to fall asleep to. It was a bad habit that had led to him always needing some sort of white noise in order to get to sleep, but it was a bad habit that his Sandrawas counting on.

As she went back to her computer, she waited for the USB to automatically run the program she had downloaded onto it. The USB she had plugged into his computer gave her complete remote access and administrator privileges and permissions to everything. As she started changing system settings and snooping through his files, she waited for Jaime to fall asleep.

It wasn't long before any rustling from his room could be heard, and the slow drone o his breathing set in, but she waited another half hour to make sure he was sleeping deep enough not to wake up, and for what she had planned to take root. She had found a series of videos, highly recommended by the online sissy hypno community, that was apparently capable of melting the brain of even the most alpha of males into a submissive cum-sucking sissy slut.

She took along sip of wine and giggled to herself. She wasn't going to go that far with Jaime, but she was going to make sure he knew what he really was. Sandra hadn't been this excited in years, and she could feel how wet her panties had become. With another drink, she transferred the first file over to Jaime's computer and pressed play.

The video started off completely black, with a voice echoing in as pink smoke filled the void.

"You're not a real man."

A beautiful woman flashed onscreen with the words. Jaime's Mother grinned with delight, it was starting off strong.

"Look at yourself. You know what you are."

Images of small dicks and soft boys who looked a lot like Jaime flashed by.

"You're just a little SISSY."

The word "SISSY" flashed on screen repeatedly as her words echoed, driving it home.

"You're not made for women."

Images of women laughing and pointing.

"You were made to please COCK."

A barrage of dicks came across the screen all different shapes and colours, but all of them large.

Jaime's Mother shifted in her seat, this was going to be just what he needed, she thought. Even without the intense visuals, the audio alone was mesmerizing. She set a timer for the file to delete itself after it had finished, in 5 hours. These videos were made to reprogram boys as quickly as possible the forum had said, and 5 hours of audio hypnosis a night, she could see why they had come so highly recommended.

This first video was all about attacking and destroying the viewers self image, and building a foundation for the following videos to work off of. The next videos in this set focused on reinforcing a sissy mindset, mannerisms, along with introductions to cross dressing and makeovers. They were all a part of the "Closeted" set, making sure the viewer was firmly established as a sissy inside, before showing off to the outside world.

The next set was called "Day to Day" and was about building that outward sissy identity. It even had customization options for if they wanted to femboy, ABDL, frilly, what have you. Jaime's Mother knew her son wasn't an actual girl inside, he just wasn't a man, so she discarded the others and kept the femboy videos.

As she scanned over the files she was keeping and deleting, she came to the third set of videos. These ones were best described as... extreme, designed for a fully committed viewer, one who was willing to throw everything in their lives away for a lifestyle, a fantasy. She chewed her lip as she idly reached down with her hand to feel her sopping wet panties. "I really should just delete these too..." she thought to herself.

. . .

Jaime woke up late the next day, well after his Mother had left for work, being none the wiser and seemingly no different. He did some chores around the house to keep his mother off his back, played some video games, and browsed online.

Inevitably however, his browsing led to less and less wholesome websites. Soon enough he had his pants around his ankles and was looking for videos to jerk off to. But as he trawled through his usual line up of women flaunting their goods at him, he found it just wasn't cutting it. His little dick was still standing at attention, but he wasn't able to cum as easily as usual. And so Jaime did something he hadn't down in a long time, and clicked on a video of a big titted blonde getting fucked up the ass by a big black cock.

Jaime had his full attention on the woman's heaving breasts and panting moans, imaging that he was the one fucking her senseless, but even if he didn't notice it, his eyes would dart down now and again, to the thick ebony dick that was pounding into her soaking pussy.

As the video came to its climax so did Jaime. The woman pulled herself off the cock and fell to her knees in front of it, jacking it off quickly before basking in shot after shot of thick cum being sprayed all over her face. Jaime meanwhile, had only managed to dribble a little load into his own hand, and as he came down from his post-orgasmic bliss, his eyes were drawn to that big black cock and it's handiwork, and he heard a voice inside of his head. "You're not a real man." Jaime burned red with shame at the sudden thought, but his cock was harder than ever.

At work, Sandra watched the live stream of her son's masturbation session and smiled as she saw the self doubt in his eyes and shame on his face through the webcam. Having gone through all his browsing history she knew that he stayed away from videos with actual men in them, so this was a pleasant development. She only wished she could see into his head and know what he was thinking at this very moment, what triggers from the hypnosis were going off. For now, having full access to his computer and webcam would have to do.

. . .

Over the next couple days Sandra kept reapplying the first video, observing through his porn habits the effect it was having on him. At night when the video was playing, she would watch him writhe and groan in his sleep, as his subconscious tried to fight the programming. During the day he was masturbating more and more and more often, and his choice of porn was changing rapidly.

The cock to pussy ratio was dramatically shifting, the videos involving more and more men, going from threesomes to foursomes, and to full on gang bangs. The point at which he chose to stroke his little member to orgasm had shifted as well. No longer satisfied with climaxing at the sight of female participant in orgasmic bliss, he was consistently waiting until after a cumshot, be it across her face, over her ass, or down her throat. Less and less frequently was he orgasmsing to vaginal creampies however, and he frequently found himself fast forwarding through to the scenes where you could see the cock shooting and throbbing.

Regardless of when he chose to orgasm however, Sandra noticed that his attitude was changing as well. Not only did he seem more submissive around the house, listening to her more, perform his chores when told, But he also no longer looked so mortified whenever he came watching a cock shoot it's load, but instead was looking more and more satisfied with himself. Even if he was blushing bright red at the end of it, he started to grow a hesitant little grin as he rubbed his pathetic dick. He would bask for a few minutes, enjoying the scenes of the woman cleaning off her lovers' cocks, and once or twice, she caught him staring a little too long at the mess he had made in the palm of his hand. She knew that it was time to step it up to the next video.

This is the first piece of erotic literature that I've decided to publish. If you have any constructive feedback or even things you'd like to see as the story progress, don't hesitate to say so in the comments.

Thanks~

Mommy's HypnoSissy