Under Mommy's Direction

Jaime had spent the last hour or so browsing through the forum's recent posts, getting a feel for it and reading through posts. There was no judgment here and everyone was very much interested in either providing help or advice to one another, or searching for connections. He hadn't delved beyond the 'Advice' and 'Listings' categories, but there were others. Shops, Trainers, Hypnos like the one he had watched. There was also a whole other side to the forum called 'Dark.' Jaime wasn't sure what was there but he thought he should at least have an idea of what being a Sissy meant before delving too deep.

Still, Jaime was feeling curious, and with his new awareness of the world of sissies, decided to make a post of his own. Just a quick introduction to test the waters and see what was available. He set up an account for himself, using his webname, and wrote up a quick post.

JayMe1:

Hi. My name is JayMe1 and I'm new to all of this. I think I might be a SIssy and I'm looking for some guidance.

That was all he felt he needed to say. He didn't want to give away too much information or come across as too desperate, so he left it at that. Almost instantaneously he got a direct message in reply to his post.

HypnoMommy:

Hi Jaime~ It's always lovely to hear from new bois discovering their sexuality. I'm always eager to help if you need it.

Jaime let out a sigh of relief. He was half worried that he'd be bombarded with DMs from pervy old men or guys looking for a free fuck. Getting a response from a female, and probably a MILF at that, was a lot less intimidating. He was so relieved that he didn't even notice how they knew how to spell his name correctly.

JayMe1:

Thanks, I'm just trying to get a feel for what this whole Sissy thing, is there a sort of guide, or rules or anything?

Once again the reply came almost instantly, as if they were able to read the response before he was even able to post it.

HypnoMommy:

There sure is. But Mommy can't be wasting her time on just any Sissy that shows up at her doorstep. Mommy needs to make sure you're worth her while. Why don't you show Mommy how you look in a cute little pair of panties?

Jaime sucked in his breath. Talking to people online was one thing, but taking pictures and sending them to strangers? Jaime bit his lip, but as much as he didn't want to admit it, the idea of sliding into a pair of his Mother's panties was getting him excited. The snug fit, the way they slip over his ass and cup his groin...

"You need to wear panties from now on."

The voice echoed in his head and Jaime snapped out of his daydream and stood up. This wasn't a big deal, girls wear panties all the time, why couldn't he? Besides, no one would ever know except for some pervert online, and that was rather exciting in its own right. Like sharing a secret with someone, only they were probably going to masturbate to this secret. The thought of his little pantied bulge driving someone wild was starting to make Jaime's head spin so much that he didn't even notice he was already in his Mother's bedroom.

Taking in a deep breath both to clear his head and to calm his nerves, Jaime made his way over to his Mother's dresser. Opening the top drawer revealed a landscape of lace and frills, satin and cotton. Black lingerie with flowery patterns and plain white cotton spread throughout the drawer, but waiting directly in the middle, just for him, was the pair of pink trimmed panties with the bow that he had tried on in the bathroom.

Jaime didn't waste any time questioning the providence of these specific panties being front and centre for his underwear needs, but simply slid them up his pale smooth thighs, nestling them snuggly against his butt, and tucking his little clitty into the front, creating the perfect little bulge, marked with a ribbon on top.

His heart was pounding in his chest now, and his dicklette was already beginning to leak, although it was barely even hard. Jaime couldn't help but run his hands over himself, letting his fingers trace the outline of his clitty in front, and sinking them into his soft ass in behind. The wetness in the front of his panties grew, and a small wet patch began to form as he leaked like a bitch in heat.

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

"Little sissy panty slut..."

Jaime repeated the words to himself as he fumbled for his phone. He stood himself in front of the full length mirror in the corner, and held the camera up in front of his face. The picture he took didn't just show of his panties, but his entire feminine body, showing off how the cute little undies rested on his wide hips, with his long curvy legs stretching out beneath them, and his pale midriff flowing up to his underdeveloped chest, with two pink nipples accenting his lack of body hair.

As he posted the photo, Jaime didn't even care that his precum had soaked through, or that he'd only been asked for a panty shot. He was reeling in the intoxicated stupor of complete and utter arousal, mixed in with the mind-melting effects of the hypnosis he'd been subjected to.As his thoughts swam aimlessly through the pink fog in his head, the response came in.

HypnoMommy:

Jaime, do you know what Geo-Tagging Data is?~

She didn't wait for his response, sending the follow-up to her rhetorical question.

HypnoMommy:

It's the data that your phones camera attaches to photos, for all sorts of reasons. What's important is that someone can look at this data, and see where the photo was taken. With a little bit of time and information, you can find out all sorts of secrets.

Jaime tried to process what they were talking about. Geo-data? Where what was taken? He didn't have long to think about it, however, as the next message came in. A long series of details that made the colour drain from his face and his phones start to tremble in his hands.

HypnoMommy:

Jaime Williams, Age 18, Male. Virginia. Recent Highschool graduate, lives alone with his Mother. I have her cell phone number. Work number too.

HypnoMommy:

You belong to Mommy now, Jaime~

...

Back in her office, Sandra was giggling excitedly to herself. Such a naive boy she'd raised, it almost made her feel bad how easy it was to trick him. She didn't even need to set it up, she probably could have just said she knew who he was. It didn't matter, and now she had a direct way to talk to him without any risk to her anonymity and all the leverage she could ever need.

When you catch a fish though, you can't start reeling in at the first nibble, you have to set the hook. Sandra was going to make sure she got enough dirt during this period of what was undoubtedly shock for him, that he couldn't try to hide from the consequences.

...

Jaime could feel a knot tying itself in his stomach, and tears starting to well up in his eyes as panic set in. Someone knew who he was! Knew his name, address, even where his Mother worked! His hands shook above his keyboard as he tried to think of a way out, something to say, some magic words to make this all go away. Another message popped up.

HypnoMommy:

Such a pretty little Sissy~ Mommy is going to take such good care of you, and you're going to be so grateful. Your Mother looks like she has great taste, so let's see what she has for you to play with. Your Mother has been single for quite a while, so I know what she has something hidden somewhere in her bedroom. Go find your Mother's dildo, and pose with it.

Jaime gasped to himself as a flurry of thoughts of his Mother as a sexual creature crashed down on him at once. Turning around and scanning the room slowly, his eyes fell on his Mother's nightstand drawers. He slowly walked over to them, scared what he might find, and scared what would happen if he didn't. Before he could find out, his phone buzzed in his hand just as he reached out for the drawer.

HypnoMommy:

When Mommy gives you an order, you will reply immediately in the affirmative.

JayMe1:

Yes Ma'am.

HypnoMommy:

Yes Mommy~

Mommy. That word made everything feel so much worse. It made him feel like a weak little boy, and added a sick oedipus complex angle. Jaime had never thought about his own Mother sexually, but now this 'Mommy' was blackmailing him sexually. He quickly texted his reluctant correction

JayMe1:

Yes Mommy.

He put his phone aside and slid open the top drawer, revealing nothing more than a trashy romance novel, a bottle of aspirin, a hairbrush, and some other random accessories. His sigh of relief was short lived as he steeled himself to open the bottom drawer. As it creaked as he slid it open he could see the glossy over of magazine shining back at him. On the cover, two burly men posed, showing off their chests and muscles, as a third kneeled in front of them, his eyes level with their semi-hard cocks. The shocking revelation that his Mother looked at gay porn was short lived in light of the new discovery of a thick black 12 inch dildo, with relistic veins, balls, and a suction cup for mounting, along with a slim chrome buttplug with a pink jeweled base.

His mind racing, Jaime grabbed all three and tossed them onto the bed haphazardly, before picking the dildo back up. It took both hands to wrap all the way around its girth, and it was heavy, heavier than he thought it would be, softer too. It was solid, but as he gripped it, he could feel some give around it. It also seems to warm at his touch, and he felt the heat from his fingers spreading through it, making it feel more lifelike in his hands.

"You were made to please COCK."

Jaime tightened his hold around the fake dick as he felt his clitty throb in his Mother's panties. This whole situation was a nightmare, so why did this feel so right? His hands slid up and down the shaft of the dildo absent-mindedly as shifted on the bed, trying to find a good pose, finally settling on a sort of side saddle sitting position on the edge of the bed, with the dildo pressed over his heart in both hands.

Trying to keep his blackmailer happy, Jaime switched up his photography technique. Propping up phone on the nightstand, he set a timer and posed, holding the big black dildo up against his chest, contrasting the size and colour of it against his soft white skin. With a quick cursory glance, Jaime sent it off, his heart pounding in excitement. He hadn't realized yet how obvious it was that he was actually enjoying this. Handling the dildo, being ordered around, controlled, with the fear of reprisal looming over him, all of this was so new and exciting. His clitty had already begun to leak, and a crystal stream of precum was dribbling from it down the front of his panties.

HypnoMommy:

My, my, my, someone's Mother likes them big, and like Mother, like Sissy it would seem~ Is that a buttplug and porno mag on the bed I can see as well? Quite the find my little Sissy~

Jaime looked beside and saw the mag and plug laying on the bed next to him in plain sight. He was being sloppy, everything had to go back exactly as it was, he couldn't let his Mother know he'd been in here at all, let alone handling her sex toys.

HypnoMommy:

Since you Mother was kind enough to lend us her toy for your little photo shoot, I think it's only fair that you do her a favour and clean it. Put your camera and the head of the bed and set it to video. I want to watch you read through that magazine as you clean her dildo with your mouth. Now.

JayMe1:

Yes Mommy.

...

Sandra was finding it difficult to type with just one hand, and her other plunged in and out of her soaking pussy. She'd already discarded her panties, and kicked off her heels, and watching her Son suck on a dildo while reading gay porn was probably going to drive her insane. She'd been using it nightly in preparation for this, but not in her cunt. A strict regiment of anal only for the dildo destined for her Son's mouth. She definitely couldn't have him getting the taste of pussy into his head, even if that's what he thought it was. Sandra let out another moan as her asshole twitched from thinking about how Jaime was about to taste it second-hand.

...

His whole body shaking, Jaime pulled himself up onto the centre of the bed and set up his phone. Moving aside the myriad of throw pillows, he set down the magazine and laid on his stomach, propped himself up on a pillow for comfort. Then he reached back blindly, groping for the black dildo that he was about to polish. His hand gripped down on it hard when he found it, and hauled it over in front of him.

Having this monster mere inches from his face established how big it truly was. It's shiny bulbous head seemed like it would fit into his mouth, but It would have to, he didn't have a choice. His eyes turned to the phone and he reached out and pressed record.

Staring for just a moment, he swallowed what was left of his resistance, and opened his mouth, letting his tongue flop out as he brought the dildo to his lips. Giving the head a wet slurpy kiss, he closed his eyes as licked down the underside of it as well. It tasted mostly like silicone, but there was a musky flavour to it. Jaime let out an involuntary moan, and his cheeks burned red as his eyes flashed open and looked to the camera. Trying to compose himself, he shifted his body and tried to service the dildo nonchalantly, licking it and kissing it up and down as he pretended to read the magazine.

"You were made to please COCK."

"I was made to please cock..."

Jaime was feeling sensations he'd never felt before. All his life he'd felt weak and small and undesirable, but right now he felt... right. He felt like this was good like he was meant to do this. Behind the positivity however, his conscience was screaming. He was naked on his Mother's bed, sucking down on her dildo on video for a stranger online that was blackmailing him. And as awful and depraved and horrifying as that was, it also felt... right.

Jaime had given up all pretense of simply cleaning the dildo. He had begun to bob his head up and down on the toy, letting it plunge deeper and deeper into his mouth, prodding the back of his throat as he hungirly tried to get the entire length inside him. As he worked his mouth down on the few inches he could fit, his off hand hand slid to his crotch, and was idly playing with his leaking clitty. Jaime could feel a wave of pleasure welling up inside of him, ready to burst out when his phone lit up, and pulled him out of the clouds.

HypnoMommy:

20 minutes is more than enough Jaime. Send me the video now or your Mother gets to see her Sissy son pitching his little tent in her panties~

Jaime frantically typed out a response as he composed himself, reeling from the bliss of sucking the dildo and the burgeoning shame that he'd enjoyed it and been doing it for 20 minutes.

JayMe1:

Yes Mommy, sorry Mommy.

He hit send on his phone, well aware that he had gone far beyond simply cleanly his Mother's dildo. He'd been sucking it like a real cock, trying to get every last inch into his throat, and now she had that on video.

Jaime waited for the response but she must have been enjoying the video. Curious himself, Jaime pulled it up and pressed play. What greeted him was the sight of a femmy boy, laying on his stomach and suckling a dildo with a gay porno mag. Soon enough however he watched a haze fall over himself as his eyelids went heavy and he started taking the dildo deeper. And then he heard himself say it.

"I was made to serve cock..."

Hearing himself say that and Watching he went to town on his Mother's dildo was making Jaime squirm. He could hear himself moan and pant as he worked the silicone cock into his throat, and the admission of servitude was to erotic. Jaime could feel his heart pounding in his chest and his breath was short and frantic.

Jaime rolled over onto his back and stared to the ceiling, listening to the wet groans and gasps from his dildo sucking video. His hand reached downinto his panties and started jerking his clitty, gripping it between his fingers. His climax rose quickly, desperate for relief and at the peak of arousal, but he couldnt push himself over the edge. He squirmed and contorted as his orgasm boiled just below the surface, torturing him with a constant state of anticipation.

You love cock, Sissy, it's the only way you can get off.

"I-I need it..."

Jaime reached back for the dildo and plunged it into his mouth. His eyes rolled back as the musky taste overwhelmed his taste buds and fat bulbous head reached the back of his throat. He pumped it in and out of his mouth and jerked his dicklette in tandem, listen to the moans from the video mingle with the desperate whining he was squeaking out now. As he pounded the dildo against his throat, his gag reflex suddenly gave way and it thrust another 3 inches down his gullet, bulging his throat and making his eyes water.

His orgasmic bliss boiled over, squirting out watery streams of cum into his Mother's panties, soaking them through and spreading a dark wet stain across the front. His throat spasmed around the intruding cock,but Jaime held it in place for the duration of his prolonged orgasm, basking in the climax. As the peak wound down and his lungs burned, Jaime slowly slid the dildo out of his mouth, dripping wet with thick saliva and mucus. He gasped for air as he rolled back over to see a new message on his phone.

HypnoMommy:

A true Sissy can't resist a cock in her throat, even if it's a fake one~ I'm going to keep you Jaime. Break you down, reduce you to your bear essence, and then train and nurture you into the perfect little Sissy you were born to be.

Jaime replyed in affirmation of her intent, desperate to discover more of the pleasures of learning what it is to be a Sissy.

JayMe1:

Yes Mommy, please train me to be the perfect little Sissy that I'm meant to be.

HypnoMommy:

Good boy. First order of business for you is to throw out all of your boys underwear. It's panties only for good little Sissies. Then we're going to need to do a thorough exploration of what your Mother has in stock. Makeup, stockings, whatever other toys she's hiding~ We're going to have so much fun~

...

Sandra sent off the message and continued to wipe down her chair. Everything was going according to plan now. She couldn't wait to get home not only to setup for tomorrow, but to tease her poor little Son about what he didn't know she knew. She was going to drive her little Sissy wild tonight before letting him settle down in bed for a long night of hypnotic brain breaking.

Sandra let out a contented moan. All of this masturbating at work was cramping her workflow. Maybe she should take a sick day...