Under Mommy's Direction Ch. 07: Condemned

You're a Sissy

You're a Sissy

You're a Sissy

The words pulsed through Jaime's mind in step with his heatbeart, each pump of blood further dragging him deeper and deeper into sexual submission and feminization. Over the course of a week he'd gone from being a regular 18 year old boy, to a panty wearing, cum eating, dildo junkie, Sissy.

And his Mother wasn't going to stop there.

Jaime had come so far, but he still had so far to go before he was the perfect little Sissy cumslut that could be sent off to university to truly discover himself, and hopefully, snag himself a wonderful man to take care of him. And while maybe he wouldn't need all the lessons that Sandra had planned for him, she wasn't going to risk sending him unprepared! She was going to make sure he was the model Sissu, and his new boyfriend could decide how often he wanted Jaime in panties, or plugged, or locked in his little pink chastity cage~

...

"Jaime~ Jaime?~ Can you hear Mommy? You're still basking in the afterglow, aren't you?~

Jaime stared blankly ahead as his heart rate calmed down and his ragged breathing began to subside. His entire body was still tingling from his orgasm, and he could feel the sensation of his cum cooling on his face as he revelled in the post-climax bliss. He could hear his Mommy's words but could hardly process them as his mind kept repeating the same phrase over and over again.

You're a Sissy

You're a Sissy

You're a Sissy

All Jaime could do was nod in agreement with whatever his Mommy was saying to him. Subconsciously however, he was processing every word, eager to accept and follow his Mommy's direction, to go deeper and deeper under her control.

"I've still got more presents for you Sissy, and I think you're just going to love the next one~ Now snap out of your cum-dazed stupor and open the next gift from Mommy~"

Jaime weakly rolled over, the blood rushing from his head as he righted himself, no longer resting on his shoulders with his clitty hanging over his face. On shaky legs he stood up and stepped over to the great big box of gifts that Mommy had sent him. He'd only made a dent in the top layer of packages, and there were plenty more after this one, his cum-addled brain half wondering what they could all be. A small box labeled #2 was sitting on the top, with a little pink bow, just begging to be opened.

"Sit in front of your computer when you open it Jaime, think of it like a Sissy unboxing video~"

Jaime dutifully sat down in his computer chair, the black leather feeling cool against his mostly exposed skin. He was still wearing the polka dot bikini that he'd pilfered from his Mother's closet, his limp clitty still hanging out the side. He scooted around in the chair, positioning himself to be centred with the webcam that his online Dommy Mommy had hacked into. Jaime watched as his computer screen came to life, and as his cursor moved across the screen on its own, opening up the webcam program so that he was staring at his own cum-covered face.

A shiver of utter shame went down Jaime's spine as he stared at himself, his face coated in cum, wearing his Mother's swimwear, and sitting dutifully for his Mommy, waiting to open his present. How did I get here? Why am I letting this happen? I need to escape! It's not too late! I can go back! Jaime's heart started to race again as the reality of the situation we was in began to sink in, his jizz soaked face a testament to how trapped he was.

You're a Sissy forever, and there's no going back.

Jaime's warped subconscious twitched in response to his panic, spitting out the messages that had been drilled into his head by a weeks worth of sleep hypnosis, positive reinforcement, and direct verbal imprinting from his Mommy.

You're a Sissy

You're a Sissy

You're a Sissy

"I'm a Sissy."

...

Sandra watched her son from the garden, using her laptop to control Jaime's computer and record everything from the cameras he had set up in his room. Watching the sudden look of panic develop on his face, and the tears begin to well up in his eyes, only for them to glaze over as he mumbled out affirmations of his Sissyhood was almost enough to make her orgasm on the spot. She leaned over and spoke into the mic.

"There's a good Sissy~ Now go ahead and open your present from Mommy, it's something that has been long overdue~"

...

Jaime slipped out of his hypnotic fog and nodded out an affirmation to his Mommy. He took hold of the pink bow on the box, peeling it off and tearing away the wrapping paper. Lifting up the long strip of tape holding the box closed, he unfolded the flaps, and opened the box.

A chastity cage.

Jaime only seen one once before, on a porno site with hundreds of categories. A quick look of revulsion had been all he'd given it at the time. Even with only a passing knowledge of them, Jaime recognized immediately what it was, and what it meant.

Inside the box lay the small pink chastity cage, and a little open gold lock in the shape of a heart. In the corner of the box was a small satin lined box, like one for earrings or a wedding ring, wrapped in pink ribbon. The keys.

"Don't worry Sissy, it's just your size~ I was worried that they wouldn't make them small enough for you, but we were in luck~"

Jaime's dicklette twitched as his Mommy's words stung at him, but he didn;t take his eyes off the cage, too afraid to look up and see his own reaction to it.

"Enough oogling it now Sissy, I want to see how it fits~ Show Mommy how cute your little clitty looks when it's locked away~"

Jaime swallowed hard. This was going to be a new low, a step further down in utter submission and domination, a complete admission of his inferiority as a man.

You're not a real man.

Jaime felt like he was being crushed, the breath being driven out of him.

Look at yourself. You know what you are.

Jaime slowly looked up and stared at his cum covered face on the screen.

You're just a little SISSY.

"Just a little Sissy..."

Jaime picked up the chastity cage and scooted back in his computer chair, so that he could himself in the webcam. He further pulled aside his Mother's bikini, fully revealing his limp 3 inches of dick, and tight little balls. He stared down at his manhood, fully drinking in how pathetic he truly was in this moment, how he was going to lock it away rather than deal with the shame. Jaime struggled for a moment, contemplating how it was supposed to go on.

"Slip the ring over the balls first Sissy~"

Jaime looked up to his screen, half expecting to see the face of his Mommy for the first time, ordering him to lock himself up, but only saw his only scared face. Looking back down he took a hold of his balls, and began to squeeze them through the tight pink ring, one at a time. The dull pain of forcing his nuts through the cage made him bite his lip as he steeled himself, and finally pushed through. He could feel the tightness of the ring, held firmly in place, snug behind his balls.

"Now slide the hood on over your clitty~"

Breathing deeply, Jaime took the pink plastic hood, and lined it up with the metal locking pins on the ring. Slowly, he slid it on, watching his dicklette disappear underneath the hard pink shell of his chastity cage. It clicked into place as it slipped over the pins, with one of them extending further through, a small hole drilled through it.

"Now lock it up, and tell Mommy how thankful you are~"

Jaime lifted up the little gold heart shaped lock, its shackle swinging freely. His eyes looked over to the ribbon wrapped jewelry box in the present as well. I have the keys. As long as I have the keys I'm free. As long as I have the keys I can go back. As long as I have the keys I can be a man.

You're not a real man.

Click.

Jaime's eyes snapped down to see that he'd closed the lock, sealing his clitty in its new pink prison. He hadn't even meant to do it, he'd just, blanked, and now...

"And what do you say, Sissy?"

Jaime didn't even think of the words. They just came spilling out of his mouth, flowing freely, and without hesitation.

"Thank you Mommy for helping me to be the perfect Sissy~"

He'd even said it in a little feminine voice, and sing-song cadence to the way he spoke.

Look at yourself. You know what you are.

Jaime stared at himself once more on the screen, now less of a man than he was before. His feeble shred of manhood now locked away.

You're just a little SISSY.

Jaime took a hold of his locked up little clitty, and slipped it under the fabric of his Mother's bikini bottoms, leaving only a hard little bulge to betray the fact that he was once a man. His Mommy's voice pierced through his moment of self-reflection.

"You're very welcome Jaime~ I'll always be here to make sure you're the perfect little Sissy that I know you can be~"

Jaime could feel the cold hard implications of what she meant. She'd always be there, watching, controlling, with the noose of revealing him to the entire world hanging above his head. Inside his cage his clitty twitched and stffened, straining against the hard shell of his new prison. He shifted in discomfort, betraying his current state of arousal.

"Aww, is Sissy already having difficulties? Don't worry, I know there will be an adjusting period for your Jaime, so I found some very helpful online resources to assist you in acclimatising to your new accessory, and to help with some basic personal hygiene~"

The mouse on his screen whizzed over to his web browser, letters flashing into the search bar and links being clicked and followed before ending up on a video on the forum site where he had found his Mommy mistress.

"Now I want you to watch the entire video, no breaks, no distractions. Just sit there and watch like a good little Sissy so that I know you can take care of yourself~"

"Y-yes Mommy."

Jaime scooted himself forward, staring at the website as his Mommy switched it to full screen. He reached for his headphones but was cut off by his Mommy's voice from his phone.

"No headphones. I want to be able to speak to you while you watch."

"B-but my Mother is home!"

"Then you'd better cross your fingers that doesn't need you for anything~ Enjoy Sissy~"

And with that she pressed play, and the black screen came to life.

...

This was it, thought Sandra, the first time Jaime was going to watch a hypnosis file, and not just listen to it in his sleep. If he sits there, just watches and listens, and lets the hypno do its work, then there will be no hope for him. No chance of resistance, no chance of escape. Audio on its own had already done so much damage to his subconscious in such a short amount of time, she couldn't wait to see what fully conscious visual hypnosis would do to him~

The livestream chat pinged to life as viewers began to trickle in, eager to watch her Sissy Son fall deeper and deeper. Something about exposing his transformation to all these people made the whole thing even hotter, as Sandra began to rub her tender clit, eager to bring herself to another orgasm at the expense of her Son's psyche.

...

The video started with a puff of pink smoke swirling in circles over a pure black background. Jaime stared and the twirling twisting plume, watching it rotate in silence as he sat obediently, waiting for the video to begin in earnest.

Hello there Sissy~ So you finally accepted who you are, and locked your clitty away~

The voice caught Jaime off guard. Clearly feminine, it was distorted and twisted. He could swear it was doubled up, speaking over itself, with each channel coming through separate speakers.

Good job Sissy, you've taken one of many important steps in becoming who you are~

Jaime winced at the thought, that there were more steps to come, further to fall.

But don't you worry your pretty little head, I'm here to help, to help you cope with your newly imprisoned clitty~

You'll face urges, desires, and it's perfectly understandable that you'd want to break your chastity~

But I'm here to give you the skills you need to stay strong, my sweet little Sissy~

Jaime shuddered, wondering what she could possibly say that would make him not want to masturbate, to willingly remain in chastity.

First we're going to start with some breathing exercises, to ensure that you're nice and calm. Follow along with me Sissy, and breath deep.

Breath in

"Breath in Sissy"

His Mommy's voice slipped in from his cell phone, sitting on the desk in front of him. Jaime breathed in.

Breath out

"Breath out Sissy"

Jaime exhaled, letting some of the tension that had been building up in him release.

Breath in

Breath out

Breath in

Breath out

Breath in

Breath out

Jaime followed the pattern, inhaling and exhaling, letting each breath take away more and more tension as his body and mind relaxed.

Breath in

Breath out

Let go Sissy, just relax

Breath in

Breath out

Let each breath take away more and more of your tension

Breath in

Breath out

Let each breath take away more and more of your stress

Breath in

Breath out

Let each breath take away more and more of your resistance

As the voice commanded Jaime to let go, breathing in and out, the swirling smoke on screen became more and more intense. What started off as a twirling wisp of pink smoke had become a roiling deep pink cloud, with light flashing through, vibrant and intense.

Breath in

Breath out

Fall deeper and deeper

Breath in

Breath out

Jaime's breathing had become automatic, in and out with the pace of the video, as his glossy eyes stared into the tumultuous storm of pink smoke.

Good Job Sissy~

Now listen carefully~ You're not a man. A real man has a cock. You're a Sissy. A sissy has a little clitty to be locked up in chastity.

Be acknowledging this, and locking up your little clitty, you've made the ultimate admission that you're not a man, that you never will be, and that you're destined to be a little Sissy slut for real men~

"Little Sissy slut..."

Jaime exhaled the words with each cyclical breath, his hazy eyes drinking in the swirling smoke that was now being cut into with images of throbbing erections, and locked up dicklettes. Every mention of real men was associated with a thick dripping cock, while Sissy was an image of a chastity cage.

...

Sandra watched as Jaime mindlessly gave into the affirmations of his Sissyhood, delighted to see his masculinity being washed away with every breath. Judging by the comments on the livestream as well, Jaime was quite the popular little Sissy. People were eager to see how far he could go, praising his passiveness, jealous of how quickly he was falling.

One comment however caught her attention, and she couldn't help but read it over and over, thinking about the implications of it in her head.

You're so lucky to have such a good little Sissy for a son. It's almost a shame he's so weak, it's always more fun to watch them fight back than give in~

Sandra couldn't help but agree. She'd enjoyed watching the confusion, the shame, the pathetic attempts at resisting her commands before submitting. He never really stood a chance, but his pathetic struggles made it all the more delicious when his willpower was overcome.

Sandra paused the video.

"Jaime~ Jaime~ Can you hear me? This is your Mother speaking~"

She watched as Jaime drowsily nodded his head, still staring at the screen of his computer, which was freeze-framed on the image of a locked up clitty in a pink chastity cage just like his.

"I want you to do something for me Jaime, something that might not make sense right away."

Sandra bit her lip, talking to him like this was risky. Without the soothing smoke or the hypnotic audio, he could wake out of his trance if she was too forceful.

"I want you to resist Jaime. I want you to keep fighting, no matter how deep and dark you fall. I want that little light at the back of you mind, the one that says 'no, I'm a man' to stay lit, no matter what I put you through~"

Jaime nodded again.

"I want you to do this, not because you're a man, and not because I don't want you to become a Sissy, but because I don't want to see you give up."

Sandra's voice was trembling as she saw the power she had over her son, how his mind was drinking in every word she said.

"It's because I want to see you lose~"

"I want to see you put up all the resistance you can muster, to fight for every last shred of your manhood, to struggle all the way through. And I want to see you lose anyways. I want to see you lose after all that fighting, because then I'll know, everyone watching will know, and you'll know, deep down inside, that you were doomed from the start."

"No matter what you did in life, where you went, what path you took, you were doomed to be the little Sissy that I'm molding you into now. You were born to be a Sissy."

"Born to be a Sissy..."

Sandra's lips curled into a devious smile as Jaime said the words back to her.

"Good Sissy~ Don't give up now, and enjoy the rest of your brain melting sissy hypno~"

Sandra pressed play, and watched the images flash on the screen again, dragging Jaime down deeper and deeper, while his subconscious tried to fight all the way.

...

Jaime's eyes fluttered, his vision out of focus and hazy. Had he fallen asleep? He rubbed his eyes as he tried to remember what he had been doing when he heard the voice.

Good Sissy, now lets get that dildo all nice and wet~

Jaime snapped to attention. The video was still playing, he must have fallen asleep with it on! His Mother was home, and she could walk in at any moment, find him in her swimsuit, the box on his bed, see the video...

His new dildo was mounted on the desk in front of him. Thick and pink, and with the words "Sissy Jaime" molded into the base.

You're going to need to make sure it's nice and slick if we're going to get it in that tight boipussy of yours~