Under Mommy's Direction
By Mommy's Hypno Sissy

Posted With Permission from Mommy's Hypno Sissy

Chapter 5

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his boys underwear. Mommy had made him take scissors to them, cutting them all to ribbons before bagging them up. Then it was doing the rest of the chores that his real Mother expected to be done before she got home.

At least he'd been allowed to put on some real clothes to get all these chores done, but every time he bent over he could feel the panties he was wearing ride up his ass, surely showing off a glimpse of pink trim, betraying his secret. As he finally took out the kitchen trash, and his own shredded undergarments, he felt his phone vibrate in his pants.

Mommy had forced him to give over all of his contact information, the passwords to his porn and forum accounts, as well as allow her to remote access his desktop. Every last bit of privacy he had once held had been handed over to Mommy, who was sure to use it against Jaime if he ever felt the urge to resist her. The truth was however, he didn't think he'd ever want to. Being controlled by this woman had been the most erotic experience of his life thus far, and even as he was doing his chores, he'd been in a constant state of blissful arousal.

Checking his phone he saw a text from his Mommy.

HypnoMommy: Do you have all of your chores done yet?

JayMe1: Yes Mommy, everything that you and my Mother have asked is done.

HypnoMommy: Good, I have another task for you. Your Mother should have left work about 15 minutes ago. Judging by how far away she works it should take her about 10 minutes to get home to you. That's all the time you have to go back into her room and pick out another 6 pairs of her panties for yourself. One for every day of the week. Oh, and do it in just your panties. If you're going to get caught I don't want there to be any chance of denial. Send me a photo of you and all your choices laid out on her bed when you're done. Have fun~

Jaime quickly sent his reply of 'Yes Mommy' and ran down the hall to his Mother's bedroom, shedding his shirt and kicking off his pants as he went. Flinging open the door his eyes darted across the room to his Mother's dresser. Digging through that would make a mess, he'd never have the time to clean it up. He scanned the room until he saw something through the door into the ensuite bathroom. Her laundry hamper!

Jaime rushed over into the bathroom, yanking open the hamper to be greeted with a rush of air tainted with sweat and musk. Inhaling deeply, Jaime took a moment to compose himself before he began his task. Sitting right on top was a purple pair with frilly trim around the waist and legs, along with a plain white cotton pair. Setting those aside, Jaime delved deeper until his hands found something moist. Pulling them out he had a sweaty pair of black boyshorts with a magenta waistband, his Mother's workout undies. His heartbeat quickened in his chest as he added the sweaty shorts to his pile.

Halfway done, Jaime thought to himself as he returned to hamper. There was a surprising amount of clothes in here considering how often his Mother seemed to do laundry. Digging deeper Jaime found a lacy black thong all wadded up. Mommy would send him back for one of these eventually he mused. A red pair revealed itself next, the fabric sheer enough that Jaime could see his hands through it. They felt silky and elegant, sliding gently off his fingertips into his selection pile.

One last pair. Jaime looked at the time on his phone, only a few minutes left. Leaning all the way one with his arm stretched down to the bottom of the hamper, Jaime felt the familiar sensation of soft cotton. Gripping them and yanking them free, Jaime held them up to his face. The style was like skimpier pair boys briefs, with the seams in the front and everything. They were a pink however, and had white trim, but what really caught Jaime off guard was the writing in back. Written across the butt of the briefs, in white lettering were the words 'Anal Addict.'

The thought of his Mother wearing these made his heart pound out of rhythm in his chest, which was only further exacerbated by the sound of the front door unlocking. Grabbing up his pile and darting out of the bathroom door, Jaime threw himself into his bedroom, slamming the door behind him. He heard the front door close as high heels clip clopped down the hallway towards his room.

"Jaime? What was that... Why are your clothes in the hallway? Were you in my room?"

Panicking, Jaime stammered out a lie, something, anything to buy himself some time before his Mother got to his room.

"I-I-I was about to hop in the shower! I w-was just looking for some shampoo!"

The sound of heels stopped just outside his bedroom door. And he heard the jiggle of hius doorknob as his Mother gripped it.

"There's more shampoo in the hall closet. Don't use mine, its specifically for my hair and its not cheap... and pick up your clothes!"

The footsteps carried away as Jaime breathed a sigh of relief. He quickly laid out his haul across his bed and took the required selfie to send off to Mommy. He didn't have to wait long before he got a less than pleased reply.

HypnoMommy: I said to lay them out on your Mother's bed, not yours. Go and fix this.

JayMe1: I can't, she's home now, I almost got caught!

HypnoMommy: Are you refusing me?

Jaime realized his mistake, talking back to the woman who had enough dirt on him from a single day to ruin his entire life.

JayMe1: No Mommy, I just can't complete the task while she's home, I'll have it for you tomorrow.

HypnoMommy: Not good enough. When I give you a task I expect it completely promptly and to the letter. I'll think of a way for you to make it up to me tonight. Go have your shower.

JayMe1: Yes Mommy!

Completely cowed by his online Mommy, Jaime didn't even notice the comment about showering that she had no way to know of. Stripping out of the panties he was wearing, Jaime stashed them under his pillow for now, put on a housecoat, and went to the bathroom to shower. He brought his phone with him just in case Mommy thought of something sooner rather than later.

Shedding the housecoat and stepping into the hot stream of water, Jaime let all his worldly concerns wash down the drain. Taking the time to thoroughly scrub himself clean, shampoo his hair, Jaime soaked under the shower head for a few moments, letting himself relax.

As he stepped out of the shower, and the cool air kissed at his wet naked body, Jaime could feel himself almost glowing. What was glowing however was the notification icon on his phone, indicating he'd received instructions.

HypnoMommy: Step one of making it up to Mommy tonight will be ensuring that you're always ready to be on display. Take the time to make sure you don't have any hair on your body below the ears. I know faggy little sissy bois like yourself don't have the testosterone to grow much, but make sure your boipussy and clitty are nice and smooth for Mommy. Don't forget to moisturize.

Jaime could feel the annoyance in her words as she used them to sting at his masculinity. He might be a sissy but he was still a male, in some way at least. Still, Jaime dug through the drawers to find the razor he'd never had to use before. He bought it just in case he ever managed to grow some facial hair and needed to shave.

Jaime ran his hands over his body, feeling for any patches of hair that he might not have noticed before. He started off with his legs, making sure the few whisps up and down his thighs were taken care of. His arms were next, completely devoid of muscle definition, and now completely devoid of hair. Even at 18, puberty hadn't had an effect yet, so he hadn't grown any real pubes, but Mommy did specifically mention his 'boipussy.'

Reaching back, Jaime spread his curvaceous ass, giving a finger access to his untouched anus. He let out a soft moan as his finger brushed across the surface, setting off nerve endings that had never felt sensations like this before. Nibbling his lip, he also felt a few coarse hairs encircling his tight puckered ring.

Squatting down, Jaime splashed some hot water onto his anus, feeling it clench and release at the sudden heat. Lathering it up was a treat as well as the slick foam let his fingers slip around as he rubbed it around to ensure an even distribution. Even the cool kiss of the razor against his skin gave him shudders as he shaved away the last few vestiges of his body hair, leaving him soft and smooth.

Jaime then bent over to look through the cabinets for moisturizer, the cool bathroom air kissing his now defenceless anus, giving him shivers. Beneath the sink was a large bottle of baby oil, almost brand new, with only a little bit used. Taking it in hand, Jaime poured it over his legs and arms, working it in thoroughly, leaving himself slick and scented. His soft stomach and crotch were next, his slippery hand gliding over his tummy down to his little balls, massaging the oil in until they slid around his waist and began oiling up his asshole. He spent almost as much time ensuring that his butthole was protected as he did the rest of his body, which was too long at that, as a pounding on the bathroom door scared him half to death.

"Hurry up in there, your dinner is on the table!"

Steadying himself on the counter and clutching his chest, Jaime quickly cleaned up in the bathroom and hurried to his room. Getting dressed with absolutely no body hair felt different, erotic even. He slid on the same pair of white and pink panties he had on earlier, wanting to get through the rest of the day with them. Feeling the back of them nestle against his now baby smooth and oiled butt made him feel all the more aware of his own ass as the fabric rubbed over his ass cheeks. Even pulling up his jeans over hairless legs made him excited, and he had to compose himself by the time he was dressed for dinner.

"It's about time Jaime. Why do you even need so long in the shower anyways?

His Mother had already finished her meal and was washing up dishes in the sink, with her back turned to him. Jaime mumbled out an excuse about losing track of time as he sat down to eat. He heard his Mother sniff at the air, hoping she couldn't smell the baby oil that he had rubbed into his skin. He didn't have time to think too much on it as his phone vibrated in his pocket with another message notification. Looking up to see his Mother distracted with her own phone, Jaime quickly opened it.

HypnoMommy: I know how my naughty little Sissy is going to make up his disobedience to Mommy. You're going to go back into your Mother's room, steal her dildo, and then spend the night snuggling it like a child with a teddy bear~

The blood drained from Jaime's face as he looked up to make sure his Mother was still distracted. She was still fiddling so he typed out quickly.

JayMe1: My Mother is home! I can't, she spends her evenings in her room and if she noticed it gone she'd know it was me!

HypnoMommy: Aw, does your Mother already suspect that you're a Sissy faggot who sneaks into her room to use her dildos? I don't care if she catches you, she deserves to know what a Sissy her son is blossoming into. So, you're going to go and steal it, sleep with it, all snuggled up to it. If you don't, your Mother can see the video of you choking yourself on her big black rubber friend.

Jaime was frantically typing, trying to come up with any sort of argument, excuse, any way to get out of this when his Mother spoke up, looking over her shoulder.

"No phones at the dinner table. Jaime! I'm going to have a shower in a few minutes, I want you to clean up the rest of the kitchen."

"Y-yes Mom!"

She'd startled him. If she'd caught a glimpse of what he was writing it would have been all over, but she'd given him a way to complete his task.

JayMe1: My Mother is going to be hopping in the shower. I'll get it then.

HypnoMommy: I don't care how. Just do it Sissy~

Jaime's Mother had a complete ensuite bathroom with a full shower/bath, so he knew he wouldn't be able to just wait until she left her room. Instead, he crept up to her bedroom door once he was sure she'd had enough time to get ready, and pressed his ear to the door. Straining to listen, he could hear the water of the shower running, and so he began to slowly crack the door open to make sure the coast was clear.

Instead of being presented with the empty bedroom that he had hoped for, what Jaime instead got to see first hand his Mother on her bed on all fours, her rear facing towards the door, plunging her dildo in and out of her glistening asshole. Jaime choked down a gasp into his throat as he heard his Mother moan out in bliss. The very same dildo that he'd been sucking on was now balls deep into her anus. She was grinding it as the balls rested against her. Her breathing was ragged and panting as she was clearly enjoying herself. Jaime's questions about why she'd have a pair of panties with 'Anal Addict' emblazoned across them were now answered. It also made Jaime realize that the musky flavour of her dildo wasn't the taste of his Mother's pussy, but of her ass.

Jaime let out an involuntary moan at the thought that he now knew what his Mother's asshole tasted like, but was drowned out by the sound of her reaching a groaning climax. He watched her entire body clench up, and then shudder for a few moments as she loosened up and went limp. Taking a few moments to recover, she slowly pulled the dildo from her ass, glistening with lube and juices. She tried to set it on the edge of the nightstand but it tumbled to the floor. Ignoring it, and ignoring the gawking eyes peering at her through the cracked door, she stood up on shaky legs, revealing her bare C-cup tits to Jaime for the first time since he was a baby. If he weren't so distracted by trying to see where the dildo fell to, or by imagining the taste of her ass on it, Jaime might've had a chance to revisit his heterosexuality. But he was distracted, and so he missed his chance as she stepped into her bathroom and closed the door.

Reacting quickly to the sound of the latch, Jaime snuck in and over to the side of the bed by the nightstand. There it was, glistening wet and half hidden under the bed. With any luck she'd think it had just rolled somewhere and he could hide it in the morning for her to find. Snatching it up and feeling the slippery stickiness of it in his hands, he crept out of her room, shutting the door behind him and absconding off to his room.

Jaime took a picture and sent it off to Mommy, proving he'd completed his task.

HypnoMommy: Good job Sissy. It looks like it was just used~ Go and wash it off, no pussy juice for faggots like you.

JayMe1: It wasn't in her pussy. She was putting it up her ass...

HypnoMommy: You watched your Mother pound her back door to orgasm? What a filthy little freak of a Sissy you are! Not one shred of respect or decency for your Mother's privacy~ Well you're not cleaning it then, but you're not sucking it either. I want the smell of ass and lube to soak into your face all night as you snuggle up to that filthy dildo. Now say 'Yes Mommy."

Jaime slowly typed out the words, wondering how far his 'Mommy' was going to continue to push him. What risks she was going to force him to take.

JayMe1: Yes Mommy.

HypnoMommy: Good Sissy, now go finish up your chores, and have a pleasant sleep with your new bedtime buddy~

Jaime stashed away his pilfered phallus, and went to work cleaning up the kitchen, his mind on edge every time he heard his Mother's footsteps around the house. She must have certainly noticed that her dildo wasn't where she'd left it, but what conclusion would she come to? More than once had she stopped in the kitchen doorway while he was washing the dishes, looking like she wanted to ask him something. But each time she had walked away before she could pose the question. Jaime tried his best to not look guilty, but he had never been a good liar.

Still, after an antagonizing evening of chores and killing time, it was finally late enough for him to head off to bed without arousing suspicion. Finally alone in his room, he stripped down to his panties, admiring his body in the mirror. He liked how the panties complimented his slender form in some ways, and his curvy butt in others. Jaime grabbed his headphones, loaded up a podcast, and crawled into bed. Reaching under his pillow, he pulled out his Mother's still wet dildo. The musky aroma of her well fucked asshole intermingled with the scent of lube.

Jaime's heart pounded in his chest as he cuddled up against the silicone cock, the utter perversion and taboo of the situation giving him heart palpitations. His mind raced with thoughts of his Mother's gaping ass, licking and sucking on her dildo, and now how that greasy ass flavoured cock was now snug up against his face as he slept. To top it all off, he was doing it at the behest of a mysterious online persona who had the power to utterly destroy his life should he refuse.

Despite all this, his cock was rock hard, and even if he didn't know it yet, he was becoming addicted to the fear, the helplessness and the submission. As the podcast droned on, and Jaime's thoughts became more and more cyclical, he slowly drifted off to sleep, cozied up against the dildo, drooling slightly over it. Down the hall and in her room, his Mother watched and waited.

There had at one point been the idea of using a strict regimen of videos to shape Jaime's mind into that of a delightful femboy, but that plan had already gone off the rails. That was meant for a more passive process, and Sandra had already gotten herself inextricably involved with her Son's morphing sexuality. So Sandra had decided that a case by case application of hypnotic programming, tailored to what she subjected him to during the day would be far more effective, and tonight she was going to test that theory.

Having Jaime watch her fuck her ass with that dildo had been a delightfully perverted experience for her, and she could only guess what went through his pretty little head at the time. Right now though, she knew exactly what would be going on, as she dragged the hypno file onto his computer. "Sissy Hypno: Anal Addict" was the name of the file, almost too fitting, she thought.

As the swirling pink mist swirled around on her screen, Sandra mused about how she was going to get him to start watching these as well, instead of just listening to them. If the audio alone had been giving her such potent results, then the video was sure to warp his weak little mind even faster. Poor Jaime wouldn't stand a chance. With a stretch and a yawn she got up from her computer and made her way to bed. She'd had a long day trapping her new Sissy Son, and she'd earned a nice long rest.

...

Jaime laid in bed, tossing and turning in his sleep as his subconscious was bombarded with thoughts and suggestions.

Hello Sissy~

Let's get one thing straight right now.

Your faggot ass was made for cock.

Jaime arched his back unconsciously, sticking out his butt as he squirmed side to side.

You're not complete, not whole, unless your queer Sissy ass has something stuffed deep inside it, whether it be a buttplug, a dildo, or a nice, thick, juicy cock~

Jaime's breathing quickened as his body scrunched up, his dicklette hardening in his panties, as he snuggled up closer to his Mother's dildo.

You can't deny it, when your faggy ass isn't being pounded you can feel that dull, itching ache, deep inside of you, just begging to be scratched~

He let out a groan that shifted into a moan as he wiggled his ass side to side, trying to scratch the itch.

That's why you need to be stuffed, every second, of every day~

Jaime's hand wandered down to his ass, holding his Mother's dildo, rubbing it against his asshole through the thin fabric of his panties.

Dildo training every day, cock whenever you can get it, and buttplugs at all times~

Jaime pressed harder, his panties acting as the only barrier between his ass and the thick black dildo.

Your queer little ass is going to gape for cock whenever its not filled, gasping and panting for it like I'm sure you are right now~

Jaime's breathing was getting erratic, his body was starting to sweat, and inside his ass was burning with a dull, scratchy ache.

Well, what are you waiting for Sissy? Start fucking your ass and get to work!

Jaime's eyes opened up, glossy and foggy, like he was still in a dream. His ass was aching and he could feel the pressure he was putting on it with his Mother's toy. Slowly his other hand slid down, taking a hold of the waist of his panties, tugging them down to reveal his fat pert buttt, and freeing his little clitty. His Mother's dildo, still greasy with lube and her ass, mixed with the saliva he'd been drooling over it, wetly kissed against his bare unprotected pucker.

Stuff it in there Sissy. Your ass was made for cock~

"Made for cock..."

Jaime mouthed the words as he pressed the head of the dildo harder against his ass. A pang of pain wormed up his spine, but it was nothing compared to the consuming need to scratch the itch burning inside of him. He let out a mewling whine as the pucker of his anus began to spread open over the tip of the toy, and then sucked in a gasp of air as it popped into his ass.

That's a good faggot, work that cock deeper and deeper~

The pain spiked and Jaime bit into his pillow, moaning into it as he relieved the pressure for a moment. But he needed to go deeper. Slowly but surely, he pressed down on the toy, deeper and deeper. 1 inch, 2 inches, 3, his asshole spread wide open around the thick black dildo as it slid deeper and deeper to his core.

Suddenly a wave of relief washed over him, a brief respite from the consuming need to fill himself. His clitty twitched as a pearl of precum began to form at the tip. Jaime instinctively drew his hand back slowly, dragging the head of the dildo over his newly discovered g-spot. Jaime's mouth let go of the pillow as he let out a moan that would have alerted the whole house had anyone been awake.

That feeling, the spot inside of you that makes the itch go away? That means you're a faggot~ Only queers, fags, fairies and Sissies have that inside them. If you feel it, it means you're gay, and there's no going back~

"No going back..."

Jaime plunged the dildo back in himself, faster this time, the tip of it grinding over his prostate releasing more endorphins and more precum. Building a rhythm, what started as a slow probing was turning into a steady fuck, as he slide his Mother's dildo in and out, over and over, his clitty twitching and leaking the entire time.

Faster and faster, his ass loosening to accept more and more of this cock, plunging deeper and deeper each time. 4 inches, 5 inches, 6. Jaime was training his boipussy to take cock like a proper little Sissy.

As you fuck your Sissy pussy, I want you to remmeber everything I've told you. You were made for cock. You can feel that ache. You'll train every day.

"Every day..."

And you're a queer little faggy fairy Sissy!

Jaime's eyes snapped open wide as his brain woke up from his hypnotic slumber. Waves of ecstasy washed over him as he groaned in pleasure as his hand continued its pistoning, fucking his ass deeper and deeper. His free hand snapped down to his clitty, stroking its thin length as his ass pushed him closer and closer to orgasm.

Panting loudly, Jaime dove his face down into his pillow, arching his ass high up in the air, for easy access, giving a show to the cameras his Mother had hidden about his room. The sounds of his whines into the pillow were drowned out by the wet slapping of the dildo plunging back and forth in his ass.

The pressure began to build inside of him, and Jaime began to feel something he never had before. A buzzing, tingling behind his clitty that was growing stronger and more intense with every thrust of the toy. It was becoming overwhelming as Jaime frantically stroked his dicklette, desperate to relieve the pressure.

It came to a head as Jaime's dribbling clitty twitched suddenly, shooting rope after rope of cum onto his bedspread, his entire body trembling as he finally stopped fucking his ass and let the orgasm take hold of him. His legs wobbled beneath him and gave way as he slumped down into the pool of his own cum. His entire body was wracked with afterglow, as he began to slide his Mother's dildo from his ass. But when the head popped free from his loosened anus, a hungry gaping ache took its place.

"Uunnhh, fuck..."

He felt so empty, so hollow. Maybe just for a little while longer...

Jaime slid the cock back inside, his hungry ass greedily accepting every inch he could fit inside of him. 8 inches of thick black dildo nestled into his body. The relief was immediate, but so was the mental anguish. He'd just fucked his own ass, in his sleep, with his own Mother's back dildo, and it was the best orgasm he'd ever felt in his life, a fact that was becoming a repeat occurrence as of late.

"What the hell is wrong with me.." Jaime mused that though as the afterglow faded and was replaced with a heavy, overwhelming need to sleep.

"You're a queer little faggy fairy Sissy~" Was the answer that followed.

...continued in Chapter 6