ACT 2
Chapter 2
Jaime sat across from his Mother at the kitchen table, staring blankly ahead as she happily prattled on about her day to him. He could see her lips moving, watching her overly exaggerated hand-gestures, but he didn’t catch a single word of it.
Instead his eyes were locked on the burgundy romper she’d put on after work. The very same one that he’d been wearing in her walk-in closet just hours before. He’d never seen her wear it before today, he thought he’d put everything back in order. Did he leave evidence? Did she know? Was it just a coincidence?
Jaime shifted in his seat, trying to adjust his jeans that were roughly scratching against his bare skin. Maybe he could have worn the panties just for comfort, but it was the principle of the matter! He’d finally stood up for himself, and he wasn’t going to back down over some itchy jeans. He’d just have to go out and buy proper men’s underwear tomorrow.
“Jaime, are you even listening?”
Jaime snapped back to reality, his Mother’s annoyed face staring him down.
“Honestly, it’s like you’re trapped in your own little world sometimes…”
She looked down at her dinner, seemingly hurt at Jaime’s inattentiveness. Jaime quickly stammered out an apology. He had been trapped in his own little world so to speak, and she’d helped him out of it, even if she didn’t know that.
“I er, uh, sorry Mom, I was completely zoned out.”
His attention turned back to her outfit. He still needed to know.
“So uh, what made you choose that outfit today, I don’t think I’ve ever seen it before?”
A wicked grin came over Sandra’s face, but she managed to twist it into a sweet smile as she lifted her head up to face her unsuspecting Son.
“Oh this old thing? I’ve had it for years but barely had the chance to wear it. Then today, someone came into work wearing the exact same outfit!”
Jaime let out a quick sigh of relief. It felt like a massive weight had been lifted off of his shoulders. Maybe he could do it, make a clean break from Mommy, get rid of evidence and everything could go back to normal.
Sandra could see his eyes lighting up, that glimmer of hope. It was almost too easy, too cruel. But she couldn’t help herself. Just the thought of crushing his dreams right before eyes was making her wet. Sandra paused to take a bite of her meal. What would a therapist say about all this she mused.
“She had come into the office for some reason or another, and we got to talking, and I mentioned I had the exact same outfit. We started talking about clothes, and makeup, and men~”
Sandra giggled at the last word.
“She doesn’t have too high of an opinion of the man in her life right now. Passive and effeminate, and then sometimes throws fits over things that are for his own good, or at least that’s how she put it. But we had a grand time talking so I asked her name so I could add her online, and you know what she said?”
Jaime raised an eyebrow as he took in a particularly large mouthful of food.
“Just call me Mommy, that’s what the men in my life seem to think I am.”
Jaime coughed and half choked on his meal as his Mother laughed to herself about her story and the other woman who called herself Mommy, before turning her attention to Jaime’s choking fit.
“Oh careful there Jaime! Go clean yourself up in the bathroom and I’ll clear the dishes. Thank you again for making dinner, it’s so nice to come home to a freshly cooked meal.”
She got up and started to usher Jaime to the bathroom, and as she collected the plates she called out after him.
“It feels like ages since we’ve really talked like this too, there’s this movie on streaming that I’ve been dying to watch, maybe we can see if it’s any good and catch up a little more after dinner~”
…
Jaime splashed water on his face, wiping off the spittle and mess he’d made of himself. The cool water felt nice against his flushed face, but it didn’t help with the thoughts swirling in his head. Had she met his Mother? Was she setting something up? What were the odds that some random woman wearing a burgundy romper who called herself Mommy would walk into his Mother’s office?
Jaime knew he was fooling himself, something had to be up. He hesitantly checked his phone. No new messages. It had been radio silence since he’d talked back, and now he was in the dark. He felt his stomach tie itself into a knot. What had felt like a time of freedom now felt like he was awaiting his execution.
Jaime interrupted his introspection with a fit of scratching at his itchy legs. No wonder people don’t go commando every day! Slowly and carefully he tugged down his jeans, to get a look at how irritated his legs had gotten. His pale smooth thighs were all covered in red marks from where he had been itching. Jaime sucked in air between his teeth, but could feel the itching subside once he fully tugged his jeans off. Was he having an allergic reaction? Was it because of his shaved legs? Feeling the material of his jeans, he’d never noticed before how coarse and rough it was, how much it even made his fingers itch.
No more boy clothes.
Jaime found himself thinking of the clothes in his Mother’s closet. The delicate fabrics, the soft materials. His mind wandered back to the cotton panties he’d been wearing all this time, how much better they had felt, how they cupped his caged dick so snugly and comfortably.
Embrace femininity.
Jaime looked back at his tender red marked legs. They still tingled with irritation. Maybe he just needed to moisturize? He looked through the medicine cabinet and found the lotion he’d used after he shaved his legs. As he poured the cold liquid into his palms, and began rubbing it up and down his legs, the tingling itch faded into a tantalizing electric buzz. He let out a soft gasp as he stroked up and down his thighs, enjoying how smooth they felt, and how luxurious it was to work in the lotion. As he worked in the last of the lotion, and the redness in his legs subsided, he felt a patch of stubble on the back of his calf that he’d missed. He’d have to shave again tomorrow to make sure he got everywhere.
Embrace femininity.
Jaime looked back to his scratchy jeans laying in a heap on the floor. Maybe just for tonight, he thought. He kicked them up into the hamper with his foot, and grabbed a towel to wrap around his waist before he left the bathroom, almost immediately bumping into his Mother in the hall.
“O-oh Jaime, be careful sweety! I just wanted to check and see if you were alright.”
She leaned in to give him a smooch on the forehead, and her eyes drifted down to notice the towel.
“Aw, did you get your jeans all messy?”
Sandra smiled. She knew. She could smell the delicates scented lotion on him. She saw him squirming all through dinner, scratching and itching. He couldn’t stand them anymore, but he wasn’t too bothered by his hoodie yet. Sandra gave a slight shrug to herself, she’d just have to reinforce it more tonight, although he did look rather cute in that oversized hoodie, like he’d borrowed it from his boyfriend.
Jaime just gave a quick nod, and mumbled something about having to go change. He said he’d just be a few minutes and then they could watch the movie together. Sandra just smiled and turned back toward the living room to leave him to it. She’d watch the camera feed on her phone while she waited.
…
Jaime swung open the bedroom door and closed it behind him. His Mother seemed to be able to sneak up on him at any moment these days. Maybe he should look into getting a door lock? Some way to make sure she couldn’t barge in on him when he was… Jaime pushed the thought from his head. No! He could do this. He just had to stay strong, and fight whatever Mommy had in store for him. Even if she came back with a vengeance tomorrow, he was free tonight, and he was going to enjoy it.
Still, as he dropped the towel and looked back down at his glistening smooth legs, he knew he couldn’t just freeball it in another pair of rough scratchy jeans. And he still needed to go out tomorrow to buy some boxers or briefs, something other than panties. For now though…
Jaime looked through his underwear collection, all the pilfered delicates that he’d stolen from his Mother. He hadn’t done any laundry yet, he’d been too afraid of getting caught, but now he’d gone through almost all of them, leaking presumably stains into the front. And he didn’t want to wear the thongs or lacy negligee. All that remained then was his Mother’s workout boyshorts. Black with the magenta trim.
He held them up by the waistband, stretching it tight across his thumbs as he examined them. He’d pulled them from her dirty laundry hamper like the rest of them, but this was the only pair that she’d done any sort of physical activity in. He could almost smell her sweat in them, a delicate aroma of perspiration and women’s deodorant, mixed with a hint of something else.
Jaime swallowed hard, and then quickly lowered them down and stepped into them. The tight fitting form compressed his caged dick against his body, but he kind of liked the snug feeling, and as he tugged them into place, the comfortable tightness was a breath of fresh air compared to what he’d endured while going commando.
He still needed some pants however. He dug through his drawers, dismissing his jeans, sweatpants, slacks, cargo shorts. Just touching them felt rough and irritating. Had everything always felt this uncomfortable? How had he managed to not notice all this time?
No more boy clothes.
Slowly but surely, he found himself thinking back to his closet.
Embrace femininity.
The outfit he’d chosen, the one he’d stashed.
No more boy clothes.
Girls jeans are basically the same thing as boys, just more comfortable and without pockets.
Embrace femininity.
Jaime stepped over to the closet, and dug out the outfit. Would his Mother recognize her jeans, with the lights off while watching a movie? His right hand slipped its way into the jeans back pocket. He’d forgotten they were heart shaped. His left hand was idlin playing with the poof ball draw string of the baby blue hoodie that was paired with the jeans. It was so soft and cozy too. Jaime was suddenly aware of his stiff nipples, and how they were chafing against the inside of his hoodie.
No more boy clothes.
Embrace femininity.
It was an outfit, paired to be worn together after all. He could just tuck the poof all drawstrings in, and sit down quickly so his Mother couldn’t see the pockets. It would be dark, and his Mother would be distracted by the movie. And they felt so cozy and soft… In his head he could hear the same mantra that he’d heard while trying on clothes in his Mother’s closet, a constant repeating chant that made his eyelids heavy and his mind fuzzy.
No more boy clothes.
Embrace femininity
No more boy clothes.
Embrace femininity
No more boy clothes.
Embrace femininity
…
Sandra watched as Jaime stripped off his hoodie, and picked the clothes off the hanger. Maybe he didn’t need any more reinforcement after all. Jaime’s movements seemed almost ethereal, dream-like. He’d worked himself up into a trance fantasizing about wearing it, and it was out of his hands now.
As Jaime tucked in the poof all drawstrings, he dreamily turned around and began heading for the living room. Sandra smirked as she shut off her phone, and set up the movie. It was a foreign film, something about romance and deceit, betrayal and love, but none of that really mattered. It was all just an excuse to get him right next to her so she could feel him squirm, and she’d taken the additional liberty of adding her own custom subtitles.
…
The living room was mostly dark when Jaime found his way in. From the doorway he could see the silhouette of his Mother on the couch from the glow of the TV screen. It was showing the preview image of some foreign film with a title that he didn’t understand. Still it was what she wanted to watch. Jaime walked forward as if in a dream. These new clothes felt so good, so right on him, but he couldn’t let her know. They felt incredible against his skin, and the risk of his Mother seeing, recognizing them as her own, made it feel like he had butterflies in his stomach.
He saw her head perk up, and as she turned to greet him he quickly slipped around the couch and took a seat on the opposite end. In the pale glow of the TV everything looked like it was in black and white, and he let out a short sigh of relief that she wouldn’t be able to clearly see what he was wearing.
“Finally Jaime, there you are! Come on now, your Mother’s had a long day, snuggle up a bit~”
Before Jaime could react his Mother reached over and wrapped an arm around his waist. Jaime had to stifle a squeak as he felt her hand on his ass. She grabbed an ample handful of his butt and dragged him in close to her, so that he was right up against her as she lounged over the arm of the sofa. She didn’t let go of his ass until she felt him settle in place, and then slowly released, keeping her hand in place.
Jaime had his hand over his mouth, holding in his breath. His eyes darted to his Mother who was now flipping through the menu options on the TV, and then to the coffee table, where he saw a half empty bottle of wine, and a quarter full glass. Oh, he thought to himself.
“I’ve been dying to see this for ages, and I haven’t had anyone to watch it with! It supposedly has been doing wonders at all the film festivals.”
Jaime could only nod as he slowly lowered his hand from his mouth, and tried to hide how on edge he was from her touch. As she pressed play however, he found himself relaxing, getting used to the feeling of her hand on his ass, and letting himself rest his body against hers more and more. The movie rolled through the opening credits, a montage, and a whole bunch of establishing shots before settling in on the view of a young woman on a park bench. The narration of a female voice spoke over the scene, in what Jaime presumed was French, and subtitles appeared at the bottom of the screen.
You just couldn’t help yourself, could you Sissy?
Jaime’s eyes snapped wide and darted to his Mother, who didn’t seem to notice anything amiss. He looked back at the screen and the words were still there, before changing with the narrator’s next line.
You don’t even need anyone to tell you, you just instinctively know what needs to be done.
Jaime’s breath quickened as he felt his heart begin to beat faster in his chest.
You’re such a good Sissy, even when you’re naughty.
Again Jaime turned his eyes to his Mother, who was taking another sip of wine, and seemingly enjoying the film.
You know you have to make it up to her, to your Mommy. You know you have to find a way to apologize for being so bad.
Jaime’s heart was full-on pounding now. Was this real, was it all in his head? Was his Mother simply not noticing because she was drunk? Was this more of Mommy’s sick tricks?
You have to be a good little Sissy, Jaime. You have to keep pushing yourself.
His name. He could feel a cold sweat on the back of his neck. This couldn’t be real, he had to be hallucinating. He wasn’t a Sissy, he was a boy! He had to be a good boy for his Mother!
Be a good Sissy for your Mommy. Take your fate into your own hands. Go and open the next gift from her box of treats.
Just then his Mother let out a yawn, lifting her hand from his butt and reaching over to pour another glass of wine. Jaime took the opportunity.
“I-I-I’ll be right back!”
Jaime jumped up from the couch and ran to his room, the calls of his Mother to hurry up trailing behind him.
…
In his room, Jaime had already pulled out the next box in sequence. It had a weight to it, but the box wasn’t all that large. It felt dense, heavy in his hands. This was the next step that Mommy had for him. That the TV told him… that he had hallucinated, that he had to take. He had to know what it was so he could… so that…
Be a good Sissy for your Mommy.
Jaime grimaced. He could still see the subtitles from the film, burned into his vision, as if they were subtitles on his life now.
Be a good Sissy for your Mommy.
He… he had to fight it… but he needed to know what he was fighting against. Yeah, that was it! How could he resist if he didn’t know what was in store for him? And with that twisted logic, Jaime quickly opened up the package, and dumped the contents out onto his bed.
Laying on his bed, and sinking into his sheets from the sheer weight of it, was the fattest, thickest, and most textured buttplug he’d ever seen. Not that he had much experience, but compared to the one in his Mother’s nightstand, this thing was a monster. It was a shiny dark pink, and a sort of egg shape, with a narrower pointed tip, and a wider rounder bottom, before merging into a wide flared base. All around the circumference were thick knurled ridges and bumps, in a spiralling cross-cross pattern. Jaime’s eyes went wide in a mixture of shock, and hunger.
He’d been so distracted throughout the day with all the clothes, and scratching, and busying himself cleaning, that for the most part he’d been able to put it out of his mind. But with this massive plug laid out before him, the empty ache inside him came back with a vengeance.
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~
That dull, throbbing, hungering ache in his ass, that Mommy had been training him to soothe with dildos, was now a pulsing undeniable hunger. He caught his mouth watering at the sight, imagining himself lubing it up with his mouth, preparing it to…
No! He couldn’t! He was fighting back! For his Mother! For his Mommy! For…
Be a good Sissy for your Mommy.
For his Mommy.
Jaime felt his knees go weak. This was going to be a struggle. He slipped his Mother’s jeans off over his ass, letting them bunch down around his thighs. He bent over the bed and lifted the fat plug up to his lips, and he kissed it, gently, letting himself drool all over it, watching it pour and ooze down across its textured surface.
As he did so he slipped down the sweaty boyshorts. He was glad he had worn them, they’d help keep this beast in place. With his ass bare to the world he couldn’t help but arch his back, putting on a display for an invisible audience.
His gentle kisses across the surface of the plug turned into a sloppy make out session, his tongue twisting and writhing across it, smearing thick drool along its intense surface. As he did so, he could feel his locked up clutter tingling, twitching up and down with a dangling stand of presumed swinging between his legs.
Throughout his intense lovemaking with the plug, Jaime almost forgot to breathe, and he leaned back, panting and drooling as he stared down at the plug. It was so fat, thicker than his dildo, thicker than anything he could have dreamed of taking at this point.
“Jaime? I’ve still got it on pause! Don’t make me come get you!”
He had to hurry. His insides were pulsing with such an aching empty hunger. He NEEDED this. Jaime’s eyes turned to the post at the corner of his bed, and its strong and sturdy design. He grabbed the plug and set it square on top, its size and mass keeping it upright. Even as he stared down at it, it seemed to tower before him like a monolith. A great challenge to be overcome. Jaime would beat it.
Climbing up onto the bed, Jaime turned on the uneasy footing of his soft mattress, with his jeans tugged down around his thighs. He couldn’t wait any longer. He needed it inside of him now!
He slowly bent down into a squat, and let out a soft coo when he felt the slick surface touch his cheeks, and then slide between them. He clenched down instinctively when it touched his tender hole. He was no longer a virgin to silicone, but this beast still scared him. As his cheeks clenched around the plug, he could feel it’s exotic texture, and fantasized about how it would feel inside of him.
Jaime took a deep breath, and willed himself to relax. His cheeks loosened, and he felt the tip of the plug press a little deeper into his asshole as it slowly began to spread across it. The ridged surface clung to the folds of his pucker, and he could feel it tugging slightly around the edges. Releasing his breath, Jaime pressed down on his thighs, and began to push the plug home.
“Hah-ah-ah-ahhhhh~”
Jaime didn’t even try to hide his moans as he began to stretch his ass around his new toy. Each time a ridge or a nub slipped over the ring of his anus, he let out a gasping moan that he prayed his Mother couldn’t hear. Despite the risk however, he kept pushing down, desperate to fill the void inside him.
As he pressed on, he felt a layer of saliva being pushed along the surface, as his hole got stretched tighter and tighter, and hungrily gripped the plug. Every aspect of it got more and more pronounced, more apparent, more intense, until Jaime found himself at a precipice. He could feel the sting of his pucker, strained as far as it had ever been so far, and he had to take it further.
Rhythmically, Jaime started breathing in and out, like a woman giving birth. With every breath he could feel himself slowly sliding up and down on the plug, gradually getting deeper and deeper. Every time he slid down, he could feel his locked updicklette twitch, another jolt of precum leaking out through the tip of the cage.
“Jaime?!”
A sudden sharp intake of breath at his Mother’s call was all it took. He felt himself slip over the event horizon, the widest part of the plug, as gravity and momentum did the rest. With a wet slapping thud he felt the plug seat itself inside of him, mashing into his prostate like a thrown football. Jaime’s cock ached against the confines of his cage as another fat dollop of pre was forced out of him.
“Ooohhhhhh…”
He could feel all of it, seated inside of him. It was like a piece of him that was missing had finally been reunited. The ridges and nubs and girth seemed to fit perfectly inside of him, as his stinging answers tightly gripped around the base. He… just needed a minute, and then he’d be back with his Mommy to watch the movie. His M-Mother!
…
Sandra meanwhile was sipping her wine and smiling deviously to herself. The comments section was going wild over Jaime stretching his ass around that monster, and donations were pouring in to buy him bigger and more exotic toys. She’d set up the shot to show multiple camera views, so you could see the expression on his face and his asshole stretching around the plug. People were posting about how thick they thought he could go, how much they wish they had access to his ass, and even a few expressing admiration for him as their own role model. One commenter even said how much they’d be willing to pay for the plug after Jaime was done with it. He was becoming quite the spectacle to his fans~
She’d had to restrain herself quite a lot to keep herself from fingering herself right there in the living room, but she wasn’t sure that even a Sissy like Jaime wouldn’t have been able to tell. Instead she slowly enjoyed her wine and watched the camera feed, taking delight in watching Jaime struggle to stand and pull up his borrowed undies and jeans. Little did he know that he’d taken a full 20 minutes to seat that plug in himself, which had also given her plenty of time to plant an empty wine bottle on the couch and set up a few donation goals on her livestream account.
She’d started off with only a few dozen people from the BDSM board that Jaime had been looking at, but with the videos and streams she had been posting, she was now up to almost 800 followers, many of which were more than willing to donate funds to ensure more content. Sandra had set up some donation tiers where contributors could suggest outfits, choose toys, and if they donated enough, select hypnosis tracks to guide his development. That was only for the high rollers however, and she’d retain the option to veto.
As she waited for Jaime she watched as the bar to the first goal quickly filled up, and outfit suggestions quickly filled in. Every donation of $25 dollars got to submit a suggestion for a later poll, and some of the suggestions were already quite scandalous. Video game and anime cosplay suggestions, the usual assortment of waitress, schoolgirl, and maid uniforms, one for a woman’s business suit, and even one suggesting a full latex encasement bondage suit. Now that would be something!
As she read through the comments and suggestions, she could see out of the corner of her eye, Jaime slowly sneaking down the hallway. She could tell from here how stiffly he was walking, and even in the dim light could see his face flushing red. She set down her phone and got herself into character.
“Jaaaiiimeee~ what took you so long! I’ve been waiting aaages for you!”
Sandra picked up and waved around an empty wine glass to punctuate her supposed inebriated state. She could see the look of discomfort on Jaime’s face seeing her like this, but she knew he wouldn’t refuse her.
“Hurry up and come sit down! I wanna see how the movie ends!”
Jaime could only offer up a diminutive apology as he quickly scooted over to the couch, and tried again in vain to sit on the far side. Sandra wasn’t having any of it however, she wanted to have him up close and personal for what she had planned. She reached over for him again, this time taking a much more aggressive squeeze of his ass as she dragged him in, like a spider would with a fly caught in its web.
“No more getting up, you hear me Jaime? Your ass belongs to me tonight and I want it planted in that seat right next to me!”
The look on Jaime’s face as she claimed ownership of his ass was a treat all in and of itself, and she gave him another squeeze before letting her hand slide up and rest on his hip. She slipped a finger beneath the trim of his borrowed hoodie, and let it rest along the top of his jeans. His skin was almost red hot, like his entire body was blushing. He was so stiff and uncomfortable at her touch, it was so adorable.
“Relaaax Jaime, it’s just your Mommy~”
She forced herself to look away from what was certainly another blushing fit, as she grabbed the remote and resumed the video. There wasn’t any dialogue in this part of the movie, just some artsy landscape shots and pensive looks. Still, she kept Jaime on edge, hiking up his sweater slightly and sliding her fingers along his exposed hips. He shuddered at her touch, and in turn she felt a shiver of lust course through her every time he let out a soft moan that he hoped she didn’t notice. Soon enough however the characters started talking again, and her custom subtitles resumed.
She can tell Sissy.
Anyone could.
She knows what you’ve been up to.
She knows what you’re wearing
She knows what you’ve got inside of you.
With each subtitle Sandra pulled Jaime up against her tighter and tighter. And with every new line she could feel him squirming, trapped in her grasp, trying to find a way to escape. Throughout this she continued to feign her ignorance, and even poured herself another glass of wine.
She knows you’re a Sissy.
She knows you’re a dildo stealing, cross dressing, caged little Sissy.
She thinks you’re pathetic.
She’d throw you out on the street if she could.
You’re garbage beneath her feet.
Sandra could swear she felt Jaime muffle a sob. She squeezed tighter, closing her trap around him.
She thinks you’re a coward.
Lying, hiding, fooling yourself.
Every time you pretend you’re a man in front of her, she sees right through you.
Jaime let out a soft gasp. It took every ounce of willpower Sandra had not to slide a hand into her pants. But she had other plans. With a dip of her head Sandra let her wine glass fall, as she laid her head against the arm of the couch, and almost closed her eyes, keeping them squinted open enough just to see the screen.
Stop lying to yourself.
Tell the truth.
You’re a Sissy.
Stop lying to your Mother.
Tell the truth.
You’re a Sissy.
Jaime was starting to hyper-ventilate. Reading those lines, wearing those clothes, being plugged, being locked away, being trapped in his Mother’s grasp. He hadn’t experienced anything yet. She let her hand slide down his hip, letting out a soft yawn as she pretended to sleep. Her fingers found the top of the heart shaped pockets on his girly jeans, and then slipped inside.
…
Jaime was panicking. Was this real? Did she know? Was the text really there on the screen? His eyes darted between the TV and his Mother. She looked like she was fast asleep.
You’re a Sissy.
Jaime shuddered in her grasp as her warm fingers slipped off his exposed hip, and back over his jeans. He let out a breath of relief, until he had to suck it back in as her fingers found his pocket.
She knows.
Then he felt it. Her fingers sliding in, and slipping under the waistband of his boyshorts. These jeans didn’t have any pockets! They were just slits that went right to his ass! He nearly jumped out of his skin as he felt his drunken Mother gliding her hand over his freshly lotioned ass, but he couldn’t force himself to move. He felt petrified as her hand went where no Mother’s hand should.
You’re a Sissy.
Jaime let out a whimper as her fingertips thudded against the base of the fat plug jammed in his ass, pressing it against the button inside of him. Oh god why did that feel so good? Did she hear that? Was she still asleep?
She knows.
His Mother didn’t stir, her eyes shut, her mouth slightly open and drooling. She nudged the plug again, and let out a moan. Holy shit, he was leaking like a faucet. This was so fucking wrong…
You’re a Sissy.
Then she stopped. Her hand didn’t move, it just lay there, cupping his ass, fingers resting firmly against his plug. His clitty twitched. Oh god what was wrong with him.
She knows.
He needed it.
You’re a Sissy.
He needed to feel it again.
She knows.
He couldn’t help himself.
You’re a Sissy.
Jaime could force himself to move and escape, but he couldn’t stop himself from flexing his hips, and grinding the base of his buttplug against her fingertips.
…
As she felt his hips push back against her hand, Sandra moved her index finger just slightly towards the middle of the base of the plug. There was a reason it was so heavy. There was a reason it was so large.
She knows.
With a whirr, the fat plug in Jaime’s ass began vibrating with the power of a cordless drill motor. Her finger pressed firm against it, driving it deep and hard against his faggy love button. Jaime’s entire body shivered against hers, and he let out a long whine as she ground the rumbling plug inside of him. The intensity of the vibrations was set to grow stronger and stronger, and she found herself having to press firmer to keep it in place.
You’re a Sissy.
…
Every panting breath out of Jaime’s mouth was a loud desperate whine. He couldn’t keep it together. He pressed his ass against his own Mother’s hand, mercilessly battering the fat silicone knob against his prostate, forcing the vibrations deeper and deeper into his core.
“Haaannnhh… M-Mommy~”
She knows.
He could feel a pressure inside him building. A faint buzzing tingle behind his clitty. He’d only felt it in passing before, with the dildos, but this was unrelenting. The plug was now vibtrating in pulses, sending thunderous waves of pleasure through his body that broke down and the foundation of his resolve. He could feel himself letting go, getting louder, pressing harder against his Mother’s hand.
You’re a Sissy.
He couldn’t stop himself. He didn’t want to. It felt like he’d been caged for ages, like he hadn’t orgasmed in ages. With each pulsing wave he felt himself getting closer, closer to release, closer to an orgasm.
She knows.
“Oh god!”
You’re a Sissy.
“I’m gonna cum!”
She knows.
“I’m a Sissy and I’m gonna cum!”
You’re a Sissy and she knows!
“I’m going to have a sissygasm!
His Mother yawned.
…
Sandra pressed her fingers hard into the base of the plug and held down the button. The vibrations stopped. She shifted in her seat and then quickly drew her hand out of her Son’s pocket, dragging her fingernails along his smooth perfect bottom, before throwing them over her head and letting out a loud overly dramatic yawn. She held it for a moment, watching Jaime out of the corner of her eye, waiting to see if he made a move. He’d gone white as a sheet and was curled up looking down at himself. His skiing shone in the light of the TV, wet with sweat, and he was breathing in quick, rapid, shallow breaths.
“Oh my goodness Jaime, just look at me! A glass of wine or two in the evening and I’m useless~”
Sandra let out a little titter as she drew her hands back into herself, taking a moment to breathe in the smell of her Son’s ass on her fingers.
“I think I need to head right to bed, otherwise I won’t be able to get up in the morning!”
She reached over a tousled Jaime’s hair with the same hand she so enjoyed molesting him with. She didn’t wait for a reply from him.
“You can stay up and finish the movie if you’d like. Obviously if I fell asleep at couldn’t have been enjoying myself very much~”
And with that Sandra wobbled off, still pretending to be a little drunk. With her back to her Son, she couldn’t resist bringing her fingers up to her lips, and giving one of them a suckle, savouring the flavour of his boipussy on them. She was going to finger herself raw tonight. No wasting time setting up Hypnos, no carefully watching him fall asleep. Tonight was all about her. Jaime could sleep on the couch for all she cared
Thank you all for reading my latest chapter in the destruction of Jaime’s fragile masculinity and his Mother’s growth into becoming a sexual predator. It has been a long time coming that Sandra got to have her way with him a little, and I know how excited some of you are for more~
As always I love reading your feedback and comments, and I love reading about new idea that you have regarding poor little Jaime. It always warms my black little heart.~
Thank you kindly~
Mommy’s Hypno Sissy