ACT 2
Chapter 1
Jaime tossed and turned in a restless slumber, his eyes clenched tight and his face in a grimace as he struggled with his dreams. Normally he'd fall asleep peacefully to the sound of a droning podcast, but not lately. Although he didn't know it, every night his psyche was under assault by waves of hypnotic programming designed to shift and warp his soft little mind into that of the perfect Sissy.
What had started out as a project by his Mother to help him realise his true self had taken a change. No longer contented with simply turning him from a young man into a femmy gayboy to be sent off to University, Sandra had become deeply entwined in her son's changes, anonymously leading him through his sissification under the guise of a domineering and controlling mistress known only to Jaime as 'Mommy.' More and more Jaime's feminization was becoming less about Jaime's self-realization, and more about her own sexual satisfaction, how low she could bring him, the debasement, the control, the thrill of reducing her own son into a Sissy faggot cumslut whose sole purpose in life was cock.
It was for this reason that she had uploaded the video Jaime was listening to now. Jaime was already deeply struggling internally with the changes to his mind and to his private appearance. He had been forced to wear panties since the beginning, but now he found his clitty locked away under chastity, with a henna tattoo above his groin proclaiming his new identity as a Sissy in elegant cursive black writing. He had even willingly taken a pill to eliminate his morning erections to better cope with being locked up. While he didn't know that the pill was actually a mix of female hormones, testosterone blockers, and nicotine to make them addictive, and that the act of relinquishing one's erections was a surrender of deep submission.
But these had all been very insular changes, private, easily hidden from the rest of the world. As things were, Jaime could live the rest of his life and no one might ever know what was happening to him under his clothes and skin. Jaime's Mom wanted to change that.
* * * * *
Sandra watched Jaime's fitful sleep through her camera feed, as he rolled about in his bed, his earbuds still firmly lodged in his ears. With the way he was tossing about, a more 'secure' solution might be required. It seemed like he was fighting it more and more, but the results were getting better and better. She'd actually implanted his fervent, impotent resistance, to make sure he didn't succumb too easily. Sandra wanted to enjoy this now, and watching her Sissy Son struggle to keep his masculinity and identity, and then to lose, made her squirm like nothing else.
Sandra slowly fingered herself as she watched him on one monitor, the text from the hypno file playing on another. She'd started this process with 3 sets of video and audio files in a well curated and designed package with the purpose of feminizing boys and men. She'd quickly broken away from that strict regimen however, and augmented it with other files she'd found online, and added a bit of her own voice as well.
Now however she was going to start the second set, the so called "Day-to-Day" portion of the hypnosis. This was designed to build the outward identity of the user, after the internal process had been initiated. It focused at first on clothing, make-up, posture and pose, but then turned to things like voice, attitude, speech patterns, and personality. There were different options for if you were looking for a true Sissy, a femboy, more prissy, more demure, even ABDL if you were so inclined. Jaime was going to be a Sissy through and through, but perhaps she would mix and match, and she was definitely going to add to this program like the last one.
As Sandra perused through the files, her attention kept going back to the third set of files. These ones were extremely intense and taboo, designed for those who were willing to fully embrace the fantasy, or those willing to force it on others. There were a plethora of pseudo-legal warnings in README.txt files in an attempt for the author to avoid any legal action, but Sandra ignored them. Instead she read the filenames as she plunged her fingers into her soaked cunt, biting her lip and the deliciousness of forcing one of these files upon Jaime. They were all video files, designed for VR but screen compatible, and sorted into folders simply according to their fetish.
AnalTraining
BBC
Bimboification
BondageBDSM
Chastity
ChastityPermanent
Incest
Maid
OralTraining
Prostitution
PublicUse
RapePlay
Secretary
Slavery
Watersports
Sandra felt a full body shiver of sexual anticipation as she read over the folders, some relatively tame, to the depraved, to the outright illegal. She'd only had Jaime watch a video once, but now he was ready for more, something stronger. And maybe if he was more aware of what was happening to him, the hypnosis, he'd struggle with it even more. Struggle and fail, all while starting to understand why this was happening to him, but far, far too late to stop it.
Sandra slipped a finger down the front of her panties, and idly began to flick at her clit. Maybe once she'd gotten him hooked on watching the hypnos, she could even upgrade him again...
* * * * *
In the once safe haven of his bedroom, Jaime was in a restless slumber. He hadn't actually had a proper night's sleep in over a week. Every night as he went to bed and plugged in his earphones to listen to his favourite podcast, his computer was hijacked and he was plunged into a deep and entrancing world of submission and feminization. Tonight's file wasn't about anal, or oral, or about his addiction to cock though. It was about clothes. And right now it was about boy clothes. And how they itched.
How can you stand it Sissy? The constant scratching, the coarse material? It feels like sandpaper on your skin~
You've done a good job already swapping out your dirty little undies for panties, but then you hide them away under ugly, baggy, boy clothes.
Well no more Sissy. Tonight you learn about the wonders of dressing up like your true self. That means skirts, bras, capris, leggings, dresses, and more Sissy!
Just the thought of slipping into a skirt gets you excited, the airy freedom between your legs, the risk of someone seeing the locked up bulge in your panties beneath, the accessibility for real cocks to get at your boipussy~
Leggings and girl's jeans too! The tight form fitting nature, showing off your natural curves, enticing all the men around you with your figure, maybe even having the whale tail of your panties expose themselves as you bend over~
Or maybe just a simple sundress, then thin material being the only thing between your body and the outside world, strutting around as if you were wearing almost nothing at all. Just the thought sends chills up your spine Sissy~
Jaime instinctively tugged the blankets up to himself as his body shivered.
It's time to stop hiding yourself Sissy. It's time to show off what God gave you. No more baggy sweaters, no more loose jeans, no more boys clothes period.
When you're wearing them, all you'll notice is how rough they are on you, how coarse they feel as they drag across your skin, and how much they itch, itch, ITCH!
You can try to cope, try to fight it, but it'll only get worse. The scratching will build and build until you're tearing the clothes from your body~
No more boy clothes.
Embrace femininity.
No more boy clothes.
Embrace femininity.
No more boy clothes.
Embrace femininity.
Jaime murmured in his sleep, as he rolled onto his side and curled up into the fetal position.
"No more boy clothes... embrace... femininity..."
* * * * *
"Jaime! Wake up!"
His Mother was shaking him awake, pulling away his blankets. Groggily he opened his eyes and the fog cleaned from his head. The tattoo! Frantically Jaime grabbed for the bedsheets and clutched them to his chest while his Mother let out a burst of laughter.
"Oh please Jaime, you're not a little girl~ You don't have to hide yourself from your own Mother~"
Jaime's face burned in shame at the very thought of his Mother seeing what his body looked like under those sheets. As he blushed, his Mother turned around and started heading for the door.
"I'm off to work now Jaime, but I want you to keep this house looking spic and span while I'm gone! If I find out you've been lazing around all day, there will be hell to pay!"
Her voice trailed off as she walked down the hall. Jaime waited in bed, still sitting upright with his sheets held to his chest. He didn't relax until finally he heard the swing of the front door and the turning of the lock as she left for work.
"Hell to pay, eh Sissy?~"
He hadn't even gotten a moment's peace before he heard her voice from his phone. He'd traded one tormentor for another.
"How did the pills work out Sissy? All nice and limp down there just like a good Sissy should be? Show me with your phone~"
Jaime picked up his phone and lifted the sheets as he aimed the camera at his crotch. Jaime didn't even remember putting on the panties last night but there they were, a pair of pink boyshorts with white trim. In the front Jaime could see the bulge of his locked up dicklette, and a large damp spot from leaking all night.
"Aw, looks like Sissy still had a hard night, even if he didn't get a stiffy. Maybe you'll need two pills tonight to keep that manly cock in check~"
Jaime winced at her mockery as he panned the camera around his crotch, scanning it over his newest feature as well. In an elegant cursive script across his silky smooth crotch was the word 'SISSY'