Under Mommy's Direction

Jaime looked down on himself, still glowing in the blissful afterglow of his orgasm, but also burning up with shame inside. His tiny 3 inch cock leaked the last few pitiful drops of his orgasm into his hand, and he looked up to compare it to the load plastered all the girls face in the video he was watching.

As she scraped the massive thick load off her face, and then sucked her fingers clean, he looked down to his own. He stared at them absentmindedly, watching his jizz glisten as it trickled down his hand. He felt a sudden plunge in his guts as came to terms with what he was thinking. Still despite his own confusion, he looked back up to the screen and stared at the large cock that was now grinding on the girls face. His little cock started to get hard again.

...

From the privacy of the washrooms at her work, Jaime's Mother; Sandra, watched with delight as her son questioned his sexuality on her phone's screen. The hypnosis that she had been subjecting him to was working far better than she ever could have imagined, and he had reached the point where it was time to start applying the next video in the set.

He had been just listening to a hypno designed to destroy his sexual identity, self confidence, willpower, but now that he had begun to openly question himself, she could start using one designed to implant new, more intense ideas about his sexuality, as well as sissy behaviours such as cross dressing, shaving, and makeup. As she idly rubbed her soaking wet panties beneath her skirt, she started to plan how he was going to fall deeper into his new identity.

That night, after Jaime went to sleep, Sandra stayed up a bit later, setting up a few surprises and installing her newly purchased spy cams in strategic places around the house. Then she settled down into her room, opened up her computer, and dragged the hypnosis file over onto Jaime's computer using her administrator access. She stopped the podcast that he had fallen asleep to, and started up the hypno.

"Hello there sissy"

The disembodied spoke over a swirling mist of pink smoke.

"It's time you learned how to act like the little sissy faggot you are."

Flashing images of sissies, cross dressers, and traps blinked on the screen, showing off how pretty they looked in their panties.

"A little sissy always looks pretty for men."

As she spoke, a second voice echoed in the background.

"Sissy, sissy, sissy, you're a pretty sissy."

The pink smoke over black swirled more turbulently, twisting and spinning.

"You need to wear panties from now on."

Up close shots of panties flashed on screen, with and without bulges in them.

"I don't care where you get them, buy them online, borrow them from a friend, even steal them from your Sister."

Sandra felt herself squirt a little at those words, and she continued to rub her clit.

"You're going to be a little sissy panty slut, and it's going to feel so good."

The words echoed:

"Sissy panty slut, sissy panty slut."

Close ups of sissies cumming into their panties played on the screen, wet damp stains growing across the delicate fabric.

"Once you feel the soft material cradling your little clitt, you'll never be able to wear boys underwear again."

More and more images of cute boys in women's underwear flashed onscreen, and one of them looked so much like Jaime that Sandra gasped as her body shuddered through an orgasm.

"Jesus Christ..."

Sandra moaned as she doubled over through the aftershocks of her climax and clenched her legs together on her hand. If Jaime even got half as far gone as the sissies in the video he would be snapped up by the first open-minded stud that laid eyes on him once he went off to University. She couldn't picture a whirlwind romance for him however, just a lot of time spent on his knees and all fours.

Looking back to the video, Sandra saw one of the triggers that she had been waiting for being planted.

"A good sissy doesn't waste a single drop of cum, and good sissy savours it."

Quick clips of sexy women and cute boys sucking cum off their fingers flickered over the screen as the hypnotic background voiced echoed.

"Good sissies savour cum, good sissies savour cum, good sissies savour cum."

Sandra couldn't help but smirk deviously to herself as she watched Jaime writhing in his sleep through his webcam, reacting to the thoughts being planted in his head. Even if he managed to resist tonight, it was only a matter of time before his willpower broke. As she turned off her display, she settled into bed, shedding her soiled panties, letting the cool sheets caress her naked body as she drifted to sleep, images of her future sissy son on her mind.

...

Jaime woke up to his Mother shaking him awake. He had slept in, and she was dressed to go out the door to work.

"Don't forget to tidy up around the house while I'm gone, if you're not going to be working a job for the summer you're going to be working here."

Jaime nodded subservently as his Mother towered over him, looking down at him. He couldn't help but feel beneath her as of late. Maybe lazing about at home was making him feel guilty, he thought. As she left his room, satisfied with his response, he lifted his covers and looked down at his crotch.

Every night for the past week he had been having wet dreams, and last night was no different. He groaned at the sight of his cum soaked briefs, and threw off the covers. Maybe this meant he was finally hitting the final stages of puberty, and that he'd start to see a little bit more muscle development soon. He headed off to the bathroom, making sure that his Mother wasn't still lurking about, and examined himself in the mirror. His slender figure didn't look any different to him, from his smooth hairless torso down to his curvy legs and ass. Despite the contradiction between his desire for more muscle, and the shapely figure of his rear, he couldn't help but feel some pride in it.

As he spun around in the bathroom mirror, something caught his attention from the corner of his eye. Laid neatly on top of the closed laundry hamper, was a pair of his Mother's panties. Without even thinking he reached over to them and held them up in front of his face. They were simple cotton panties, mostly plain white, but with pink trim and a little pink bow of the front. Jaime started at them for what seemed like ages before he noticed the aching throb of his cock in his own soiled underwear. Stripping them down, he found himself completely naked, holding the panties delicately in his hands.

"They feel so soft..."

Jaime lightly stoked the fabric, letting his fingers trace over the waistband and fiddled with the little pink bow on the front. He could feel his heart pounding in his chest, and a pit in his stomach as he slowly lowered the panties down to his legs, and stepped into them. As they glided up his nearly hairless legs, he let out a gasp and shuddered and they nestled around his balls, and pinned his cock to his body.

Looking in the mirror was shocking to him, as he realized what he was doing, and much worse, that he looked almost entirely like a girl from the wait down. The panties framed his waist and the top of his legs perfectly, the pink trim contrasting against the white fabric and his pale white skin. Even the bulge of his hard cock was barely visible from this angle, and even worse, somehow only served to make him look more feminine. As his entire body turned red from the shame, he frantically reached down and grabbed his cumstained briefs.

Feeling the wet spot in his hands triggered a voice in his head. "Good sissies savour cum." Jaime brought his briefs up to his face, and inhaled deeply. He could smell the light musk of his own body mingling with the salty sweet scent of his cum. His cock throbbed in the panties and his lips trembled.

He felt so hungry. Not like a normal hunger but like a pulsating, longing desire. His heart raced in his chest as his breath quickened, his cock pulsating and grinding against the panties with every beat and breath.

Panting, Jaime gasped his fingers around the bulge of his cock, gripping it through his Mother's panties. With only a few quick strokes, he felt his knees go weak as his legs buckled and he slumped down onto the plush bathmat. Kneeling on the floor, Jaime came the hardest he ever had in his life, his cock spurting his thick load into the front of his pretty panties. With each pump, his cock rubbed up against the soft material, creating a feedback loop of pleasure that made his head go fuzzy. Doubling over forward, he spent what seemed like eternity hunched over himself on the bathroom floor, as waves of orgasmic bliss cascaded over his entire body.

As Jaime gradually slid down from his euphoric high, he began to realize what he had done. He stumbled in front of the bathroom mirror, wearing nothing but a pair of his Mother's panties. He could see the large wet stain on the front, spreading slowly as his cum soaked into the fabric. Disgust washed over him as he braced himself on the counter, reeling from the shock of what he had done.

"What the hell is wrong with me?"

...

Sandra was reeling from an orgasmic realization of her own, having cum three times at the sight of her effeminate son first wearing her panties, then huffing his briefs, and finally enjoying the taste of his own fresh cum. She panted softly, hoping she hadn't made too much noise from her corner office. Jaime was progressing far faster than anything on the hypno forum had led her to believe, galvanizing her conviction that her son truly was a sissy at heart, and that she was doing the right thing. After adjusting her skirt and sanitizing her hands, she straightened herself up at her computer and rapidly set to work.

After a shock like that, she was worried that Jaime might try to go to the straightest porn he could find in order to reaffirm some sense of his fragile masculinity. Sandra had thought ahead for just such an occasion however. Signing into Jaime's account on his most frequented porn site, she started changing his account preferences. She blocked all the lesbian and solo female videos, ensure that no matter what, he would be staring at a least one cock. Then, she started altering his browsing history, using a bot to rapidly select videos in order to alter what would be recommended to him. She focused it on female on male blowjob videos, so as to not raise too much suspicion, but also set it to work on sissy, cross dressing, and trap videos, to ease them into his recommended videos.

As Sandra let the bot do its work, she watched Jaime towel off from the cold shower he had taken in the wake of his shameful masturbation session. She stared at his body enviously. His naturally perfect and smooth skin, his shapely legs and ass. Hell, even his cute pink little nipples would look cute on a proper set of tits. She hadnt had a figure like that since her 20s and even then it had been the result of careful dieting and hard work. Jaime simply had it too easy, and she wasn't going to let him waste this natural beauty.

When he finished toweling himself off, he hesitated for a minute before tossing both his briefs, and the panties she had bought specifically for him, into the laundry hamper. It would be fun to see him come crawling back to pick them out of the hamper, or even to sneak into her room for a fresh pair.

Switching camera feeds, she saw him drop his towel, and settle into his computer chair. She could see his screen and the links he was clicking as he made his way to his favourite porn site and started going through his recommended videos. His pretty face twisted in frustration as he jumped from blowjob video to cumshot compilation video to interracial gangbang video.

With each video his skin was turning redder and redder with what she suspected was a mix of shame and confusing arousal as watched cock after cock pump hot sticky loads of cum into and onto pretty young sluts. Finally, his rapid clicking stopped after he found himself on a type of video he had never seen before.

A young cross dresser was wearing a white cotton bra and a pair panties. His hair was done up in a cute little do, and it looked like he had put some eyeliner and lipstick on. The real interesting thing though, was the fact that he was on his bed, upside down, with his back propped up against the wall, and his hips hanging over his head. For a cute little trap, he had a sizeable dick, and it was hanging mere inches above his open mouth. Jaime was frozen in his seat, enthralled by what he was seeing.

The little sissy was jerking his cock, pumping it frantically at his open mouth, all the while whimpering and softly begging himself for a fresh load of his own cum.

"P-please... fuck... I need it... I need to taste it!"

Suddenly, he thrust his hips forward in synch with a series of passionate strokes and pathetic whines, and the head of his cock met his lips. Holding it there, his balls clenched up, and Jaimed watched as his cock throbbed and shot a load into the sissy's hungry mouth.

"Good sissies savour cum."

A voice spoke only within the confines of Jaime's head. But he repeated it back regardless

"Good sissies savour cum."

His head jerked to attention and he looked around frantically. Why did he say that? He'd never even watched a video like this before. Was that even true?

The cross dresser on screen rolled over on his bed, and he crawled over to the camera, showing off his mouth full of yummy cum, before swallowing with a big dramatic gulp, and showing his empty mouth. Jaime automatically licked his lips, as he was once again sucked in by the video. With a wink a giggle, and a peace sign, he reached offscreen and the video ended.

Staring at the now black screen, Jaime feverishly opened up the trap's profile, looking for more.

...

Sandra sat back in her chair, basking in her success. Not only had she not raised suspicion with the alterations to his account, but he had watched the entirety of that sissy's self suck video with rapt attention. Now she could start loading almost anything sissy video into his feed without the least bit of concern, dragging him further down as she rewrote his subconcious. She was going to need to step up her preparations however. With the rate Jaime was developing at, she couldn't risk him getting too far ahead of her. She needed to keep him busy at home, trapped and isolated, fully under her direction.