Under Mommy's Direction

The sun shone in through the cracks between the curtains on Jaime's window, spreading a long thin strip of golden sunshine across his bed and onto his sleeping face. The beam shifted with the rising of the sun until it shone over Jaime's eyes, which fluttered, then slowly opened.

As Jaime awoke to the world, memories were awakened within him. Panties, dildos, Mommy, fucking his ass. His eyes snapped open wide as the events of late last night came back to him, as well as the tender pain in his still stuffed asshole. Jaime groaned in discomfort as he reached back and slit the thick black dildo from his formerly pristine anus. He could feel the pain and heat pouring off of his tender ring, having been stretched to its limit the entire night. He traced his fingers around the rim of his asshole, soothing it slightly as he fingertips slid over his smooth and freshly shaven ass. He could feel his heart starting to beat faster, and knew he had to stop.

It was Saturday. His Mother was home.

...

Wrapped up in her housecoat and sipping a cup of coffee, Sandra was watching the recording of the spycam hidden in her Son's bedroom. Watching Jaime toss and turn as the hypnosis warped his mind and implanted instructions was always a treat, but she nearly spat out her coffee when she saw him wake into a half dazed state about halfway through.

Sandra's eyes were locked to the screen as she watched her Sissy Son fuck his ass for the very fist time with her own dildo, building up speed and depth as he loosened himself. He writhed and moaned into his pillow, until his eyes snapped open and he started to jerk himself off wil fucking his ass.

Sandra let out a short sigh of disappointment, a prostate orgasm would have made this a legendary experience, but his little clitty had to get in the way. That needed immediate fixing. She wasn't planning on getting him one just yet, but things were advancing at a rapid pace, far faster than she'd ever imagined possible. She'd have to go out shopping this morning, and give Jaime a few "chores" to keep him busy while she was out.

...

Jaime was just pulling on a pair of his Mother's work-out underwear, a pair of black boyshorts with a magenta trim, when there was a pounding at his door.

"Jaime! Get up! I'm going out on some errands. And if you're going to be so lazy and sleep the day away I've got more chores for you! Strip the beds and get the bathroom towels, and do a load of laundry. I'll be back around lunch and I expect it to be done!"

Jaime could hear the heels of his Mother's shoes clip clopping down the hall as she went to the front door. He listened for the creak of it opening, then heard it slam shut. It wasn't 5 seconds later that his phone pinged with a new message from his "Mommy."

HypnoMommy:

Looks like someone has the morning to themselves~

Jaime stared at the message, frightened at the implications that this strange woman knew what was going on in his home.

JayMe1:

How did you know?

HypnoMommy:

Mommy has her ways~ But that doesn't matter now Sissy, what matters is what you'll be doing this morning in addition to any chores your Mother may have given you~ DId you sleep well last night? Were you able to resist from sucking and slobbering all over that greasy dildo?

Jaime decided to answer truthfully, if not the whole truth. As much as being under this woman's control excited him, she already had way too much dirt on him. We worried how far this could go if he kept following her commands...

JayMe1:

Yes Mommy, I didn't suck on it all last night, just like you said, I promise.

HypnoMommy:

I'm not sure I believe you Sissy~ No matter, we got interrupted yesterday, now it's time to go back and take full stock of what your Mother's room has to offer a budding little Sissy. I want you to take pictures of her lingerie drawer, her makeup stand, and then we're going through her closet to see what secrets she has hidden away. You can even stash that filthy dildo back where you found it. And if you're a good boy, I've got a special surprise for you later~ Hop to it Sissy~"

Jaime quickly replied with a "Yes Mommy" and sprung into action. Stripping his bed, he dragged his sheets into the hall and threw the bathroom towels in a heap on top. Then he went to his Mother's room, stripping her sheets and taking the towels from her bathroom.

Throwing those out into the hall, Jaime looked back into his Mother's room, her bare mattress dominating the room. He slunk back into his room and retrieved the dildo that had changed part of him forever. Still wet from an entire night in his ass, he felt a twinge of pain in his rear as he bent over the bed and tucked it into the middle. He stared at it for a moment, as it sat there, his mind starting to wander, but snapped back to reality as he remembered the tasks his Mommy had set out.

He went into the bathroom and surveyed the products and makeup strewn about the counter and in the cabinet. Mascara, eyeliner, eye shadow, lipsticks, rouge, foundation, and plenty of things he'd never even seen or heard of. He took several pictures, making sure that he got a photo of everything that Mommy may want to see.

As he sent them off he opened his Mother's underwear drawers, revealing her mixed collection of bras and panties, including her dark lacy lingerie sets. Jaime could feel his heart pounding in his chest as he imagined his own Mother, and then himself, fully dressed up in the delicate lace. His phone's camera shuttered noisily as he took picture after picture of her unmentionables, spread across two full drawers of her wardrobe.

All that was left was her walk-in closet, and Mommy hadn't responded to any of the photos he'd sent her yet. Opening the door and stepping in, Jaime could smell his Mother's perfume, that she would only wear on special occasions. He closed his eyes for a moment and took a deep breath in. Lining one side of his Mother's closet was a long rack of dresses, on hangers, business suits, even a bathing suit or two. On the other side was a set of shelves built into the wall, filled with shoeboxes, loose shoes, hats, a large jewelry box, and other various accessories.

Jaime took a wide photo of the entire closet, then began taking ones of individual items. There was no way he'd be able to take photos of everything, so he began picking and choosing, and sending them off, waiting to see if there was any other direction from Mommy. A little black strapless dress that she would wear on the occasional night out, a red gown backless gown with a deep v-neck and cut-aways for the legs that he'd never seen before, a light yellow flowery sundress she would wear in the garden, and a black and white polka dot bikini with red trim that he remembered from his childhood.

Looking at the shoes, Jaime was far less knowledgeable. Any array of footwear some with almost no differences and others with diverse shapes and sizes were tucked amongst shelves and shoeboxes. Jaime took photos of sandals, high heels, wedges, flats, boots, and even a pair of what he could only describe as stripper heels, tucked in back behind a pair of green crocs. Her jewelry box was even more out of his depth as he took photos of entire drawers crammed full of rings, necklaces, bracelets, earrings, all jumbled together and organized in a way he suspected even his Mother didn't fully understand.

Finally his phone pinged with a notification as he was preparing to take photos of a particularly wide brimmed sunhat.

HypnoMommy:

Your Mother has good taste SIssy, I can see she is quite the sophisticated woman. It is not, however, the style of clothing for a slutty little Sissy like yourself. Most of it at least~ I can see a few things I'll be having you "borrow" but I doubt the rest would fit you and your flat chest, and I'd hate to have you ruin any of your Mother's beautiful clothes.

Jaime let out a short sigh of relief. Maybe this meant she wouldn't be making him do anything too extreme if his Mother's clothes didn't suit him. He could still feel a twinge in his stomach as he looked back at the bikini however.

HypnoMommy:

No matter, we will have to make due. There is one more thing I would like you to look at for me Sissy. I can see in your first photo a shoebox tacked way in the back corner, behind those boots. My woman's intuition is giving me quite the vibes about it~ Stream it live to me.

Jaime craned his neck to lean over and spotted the lone shoebox, meticulously hidden behind a barrier of knee high boots. It had a thin layer of dust on it and looked like it hadn't been moved from its spot in some time. He took his phone in one hand and turned on the camera, streaming live video directly to Mommy. He awkwardly lifted it out of its hiding spot with one hand and set it atop the jewelry box. Making sure that the image composition was good first, he flipped off the lid of the secret shoebox.

What greeted his and his Mommy's eyes was a box full of straps and buckles, cuffs and chains, gags and blindfolds, and a 12 inch strap-on that made Jaime's blood run cold. Jaime could only breath out the words "holy shit" as he stared stunned at the contents of the box.

"Quite the collection your Mother has there, Sissy. Think she'd ever use it on you?~"

Jaime nearly flipped out of his skin at the sound of his Mother's voice, no, his Mommy's voice! He looked down at his phone only to see the image, indicating a lack of a profile picture, but seeing that she was talking to him over the stream.

"I'm only kidding Sissy. Mostly~"

Her voice was rich and husky, and practically dripping with eroticism. Every word she spoke seemed to scream sex, and yet it sounded so much like his Mother's sweet, if sometimes, critical voice.

"I hope I didn't scare you too much, I can see the shock in your pretty little face~"

Jaime realised as he stared down at the screen, that the active camera had changed to selfie, and that his wide eyed look was being seen by his Mommy. He quickly turned the phone away, his heart still pounding in his chest, his body trembling, and his cock rock hard as he listened to a hypersexualized version of his Mother's voice tease him and call him a Sissy. He stammered out a reply, his voice wavering and shaking.

"N-no Mommy, you j-just startled me!"

"I could see that Sissy, you nearly hit the ceiling~ But you've been a good little boi so far today, so what you're going to do now is take that polka-dot bikini from the back, there, hang it up in your closet, and then do some more chores for your Mother. I'm not the only woman in your life that you have to keep happy, and it seems like she has her own way of punishing naughty bois~"

Jaime's mind was filled with scenes of himself cuffed and gagged, with his Mother towering over him, twelve inches of dildo hanging from his hips. His stomach twisted and his dickletee ached.

"I'll have something else for you to do later though, along with your reward for being so obedient. Take care Sissy~"

With that the video stream ended with a beep, and Jaime was left alone in his Mother's closet, and her box of secrets open wide before him.

...

Sandra was sitting in the front seat of her car, parked outside of a seedy local stripmall with some particular bussinesses, and she was grinning from ear to ear. It was almost too easy. She'd spent the whole morning shopping, only watching the messages from her unwitting son for when he finally ended up in the closet. The irony was not lost on her. Making him open that box and discover what was within had been her main goal for him this morning. Having him livestream it and then surprising him with her 'bedroom' voice had just been icing on the cake.

And now that she'd broken the ice on voice chatting, it was time to get him on camera 24/7 knowingly. The spy cams in his bedroom had been fun, but for what they provided in stealth, they lacked in video quality. A box of high definition wifi cameras sat on the backseat of her car, along with several shopping bags from some local teen girl and young woman clothing stores. She just had one more stop, and then she'd be getting them ready for 'delivery.'

...

Jaime was back at home trying to keep his mind off of what he'd just discovered. He had taken his Mommy's advice and was busying himself by cleaning up around the house; cleaning windows, tidying the living room, doing the dishes from breakfast. Every time he took a moments rest though, he found himself thinking about his Mother, chastising him for his laziness, while brandishing the strap-on hooked to her crotch.

His disturbing fantasies were interrupted by the sound of the front unlocking and swinging open, and his Mother coming in with arms full of groceries.

"Jaime! There's bags in the car, come give me a hand!"

His Mother yelled out from the front door, and had a look of pleasant surprise when Jaime immediately appeared from the kitchen, evidently having been doing some cleaning.

"Oh perfect, you've been getting the placed cleaned up. There are more groceries in the back seat, as well as a package for you that I picked up at the post office. Thanks sweetie~"

Sandra leaned over and gave Jaime a kiss on the forehead. He was noticing for the first time how tall she seemed, especially with her decision to wear heels as part of her day to day. As he bowed his head and made his way to the car to hide how much he was blushing, he turned back to watch her as she clip-clopped down the hall towards the kitchen in her heels, her hips sashaying the whole time.

Jaime gave his head a shake and looked into the back seat of the car. There was indeed a package for him, and it was large. The box was at least the size of microwave, and definitely had some heft to it as well. Looking for any sort of mailing tags, Jaime froze before he could notice that it didn't have any. Mommy had said she had a surprise for him...

Not wasting a second Jaime lifted up the box and headed for his room as fast as he could without drawing attention, but couldn't avoid his Mother stepping out from the kitchen just in front of him.

"Careful there sweetie, gotta watch where you're going. What in that box anyways, I had quite the time manoeuvring it into the car for you?~"

Sandra was playing up the loving Mother role, and she knew how uncomfortable it was making him. She could see the panic in his eyes, and the sweat forming on his forehead. If it weren't for the box full of goodies in his arm, she would probably be able to see the little tent his was undoubtedly pitching as well.

"Uh-uh-uh... Ch-Christmas shopping! I didn't want to uh, spoil the surprise?"

She smiled knowingly at him, though he wouldn't be able to tell. It was almost pathetic how bad he was at lying, he couldn't even pretend to sound like he believed it.

"How thoughtful of you, getting ahead of the rush. I won't pry then, just be more aware of your surroundings."

With that she put her hand on his shoulder as she stepped past him, holding him firmly with her weight on him, rooting him in place. She strutted her way towards the front door to retrieve the rest of the shopping, letting Jaime stew in his fetid fantasies.

Jaime slammed the bedroom door behind him and set the box up on his bed. This was getting to be too much he thought as he peeked out back down the hallway. He saw his Mother coming back inside, a few bags in her hands, and shutting the door behind her. She took the bags into the kitchen, and then yelled out after him.

"I'm going to put these away and then go out into the garden, make sure you toss the rest of the laundry into the dryer!"

"Yes Mommy!"

Jaime cringed as the words spilled out of his mouth almost instinctively. Mother and Mommy had already been confusing enough, but now that he'd heard her voice, it was almost indistinguishable from his own Mother's. The only clear difference was the way Mommy infused each syllable with perversion when she spoke. And almost as if on cue to make his point, a voice spoke out from his phone.

"Seems like someone got their package. And who is this other Mommy that I'm hearing about~"

Jaime was beginning to understand that the line of separation between his day to day life, and the fantasy that Mommy was building with him was getting thinner and thinner.

"I just mispoke Mommy, th-that was my actual Mother..."

"Ooh, you mean the strap-on wielding dominatrix~ You don't even realise how lucky you are to have two women like us in your life. Look at how I spoil you, buying you gifts and presents to make you happy! Do you like what I got you?~"

"I haven't opened it yet Mommy, I just got it in my bedroom."

"Well don't keep me waiting, set up your phone and open it up, I want to see your reaction as we go through what I got you~"

Jaime set up his phone on his nightstand, aiming the camera at him so his Mommy could see him. He picked at the tape, and pulled it off in a single long strip, letting the flaps of the box spring open. The first thing that Jaime saw wasn't a sex toy, or a new pair on panties, but it made his heart flutter just the same. A series of battery powered wifi enabled webcams were setting in the box, their red lights already blinking as they recorded his reaction from slightly different angles. Beneath he could see even more packages, all sealed with numbers on them.

"Hello there Sissy~ I was getting tired of waiting for you to be in front of your computer or phone to get a glimpse of you, and now I won't have to~ Anytime you're in your room, I'll be able to watch my little Sissy slut. They've automatically linked up to your wifi, so get up on a stool and use the two way tape to install them in the corners."

Jaime trembled as he held the small camera in his hands, staring directly into the lens as his Mommy instructed him to destroy the vast vestiges of privacy he had from her.

"Or I could just use the footage I have already and send it to your 'real Mommy~'"

Jaime had to listen to her laughing derisively as he obediently climbed atop his desk chair, and started installing the cameras. For the first time she actually sounded mean as she teased him about his predicament, and Jaime wracked his brain trying to think of a way he could ever possibly get out of this.

"That's perfect Sissy, nowhere to hide~ Now how about we do something about that outfit you're wearing? Jeans and a t-shirt may be fine for chores, but Mommy wants to see you dressed up. Strip. And then go get your Mother's bikini from your closet~"

Jaime looked up at the cameras in the corners for a moment, before resigning himself to the situation. He was falling deeper and deeper under her control, and what was worse, was that he wasn't sure if he wanted to stop it. So slowly, and sensually, he slid his shirt up and off over his head, revealing his pale undefined chest, and his small pink nipples. He unbuckled his belt and let his jeans fall down around his ankles, revealing the black boyshorts with the magenta trim that he'd stolen from his Mother. But even those came down around his ankles, until he was sitting on the edge of his bed, tugging the socks from his feet.

Even with the fear and anxiety that Jaime was feeling about his predicament, he couldn't deny he was desperately aroused. His meager dick standing at full attention as he stood up and went to the closet to retrieve the pilfered bikini. Breathing heavily, images of his Mother sunbathing in the polka dot bathing suit while he splashed in the water, flashed through his head, as he soiled the memories by tugging up the bottoms and nestling his hard cock into them.

Pulling the top tight against his chest, he had to tie the string in back much tighter to keep it on, highlighting his flat chest, sexualising his body in a way he'd never experienced before. Looking in the mirror, he could feel the shame and excitement as he scanned over his body. Had it always been this skimpy? Even with his lack of breasts, the bra seemed to leave so much of his chest exposed, and even his 3 inches of dick looked ready to burst out of the bottoms. His reflection was interrupted by his Mommy's voice however.