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 sinop escort 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 escort sinop 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 sinop escort bayan 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.