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The Sissy Inheritance

“Smile Claire”

Claire looked up from cleaning the toilet with the toilet brush attached to her gag to see her Stepmom Megan and Stepsister Emily taking a picture. Claire was use to them taking pictures of her while she was bound and gagged and let it happen. She thought back to earlier in her life, when she would have been embarrassed by this happening. Back then she was known as Clark.

Ever since his mother passed, it had just been Clark and his dad, Alan. Despite being a very successful businessman, Alan was still a very good single father to Clark. They were very close. That was until Clark went to college. During Clark’s freshmen year, Alan met Megan. They hit it off. When Clark was home between his first and second year, Alan and Megan got engaged. It was after this Clark met Emily, his new stepsister. Clark could see a change in his father, but he seemed happy and that made Clark happy. During Clark’s second year of college, Alan and Megan got married. When Megan moved in she brought her own maid, Tiffany, with her to take care of the house. Life was going on, until Clark’s third year of college, when Alan disappeared. Clark was in complete distraught over this. Eventually Alan was declared dead. They had a funeral. Then at the will reading, Clark discovered what his fate would be. Clark thought he would inherit a decent amount of money, but was shocked when his part of the will was read. It stated that Clark would need to move back home and serve his stepmom and stepsister to get an allowance or he would have to move out and get absolutely nothing. Clark was scared about being forced to move out and have nothing to his name and not knowing what serving his stepmom and sister would entail, he chose that option. He was forced to sign a contract, which of course he didn’t read throughly enough.

Over time it became clear what serving them meant. If he didn’t do exactly what the contract stated, he would face huge legal ramifications. He was forced to dropout of college altogether. He moved back home and was forced into a pink chastity cage. All his male clothes were donated. His boxers were replaced with panties, his socks were replaced with stockings and garter belts, his sleep shorts were replaced nighties, and his jeans and tshirts were replaced with skirts, blouses, and maids uniforms. When he was serving them he was in a maids uniform, when off duty, it was female clothes only. Finally he would no longer be Clark, his new name was Sissy Claire. While he did resist at first, through bondage, Hypnos, and chastity, she eventually learned to accept her fate. Eventually his stepmom and sister simply became Mistress Megan and Mistress Emily. She hasn’t worn anything male related since the day of the will reading. Now two years later, Claire is having her picture taken while bound, gagged, and cleaning the toilet with the attachment on her gag. Her little clitty has not been freed in over a year. Her only form of pleasure comes from her vibrating plug, which is controlled by apps on his mistresses’ phones. Claire learned to work well with Tiffany, who also had a hand in training Claire.

“Claire we need to have a meeting once you finish in here come down stairs” Megan said. Claire finished quickly and met his mistresses down stairs. Tiffany was already standing behind Megan. Emily led Claire to a chair and bound her even more to it. Finally Emily took out the gag Claire uses for chores, but her mouth didn’t stay empty for long as Emily added Claire’s penis gag, a gag which Claire has learned to love.

“Claire, you have been our sissy slave long enough, it’s time you’ve learned more about how your fate led you here. When I married your father I had been training him for some time to be a sissy like you are now. I used that power over him to change his will to how it was. In the original will you were set to get most of his fortune. But I felt like this turned out for the best. Now onto the truth about your father. He never disappeared, I sold him to a friend of mine. He is sissy Alice now. One day soon I will allow y’all to be reunited again. Perhaps y’all will both serve at a party we will throw for all of my mistress friends. The reason I didn’t keep your father for myself is because I already had a sissy. Tiffany here is actually my first husband and Emily’s father Timothy. Show Claire your locked up clitty Tiffany and now that your secret is out, go put on your gag.” Megan commanded as Tiffany lifted up her skirt and pulled down her panties to reveal a tiny locked up clitty. Then Tiffany left the room, only to return is a similar gag to the one Claire was wearing now.

“Now I’m sure your thinking we are just some gold diggers for what we did to you and your father. But the truth of the matter, it had nothing to do with him or his money, that was just an added bonus. We actually did this, because of you. Once I met you, I just knew you would make the perfect sissy for my daughter. She had helped train her father growing up and she always wanted a sissy of her own. Once she got old enough, we found you and that has brought us to today, where your ownership goes to her.”

“Umm…hi. This is, um, my presentation…”

My heart is pounding under my frilly blue frock, my gut churning, my mouth dry as I try to articulate the words. Mommy is in the little eight-person audience: watching, waiting with our other kinkster friends to see just how well her little sissy babydoll can humiliate herself. I need to obey her orders, to give my little show-and-tell as best I can, and most of all, to make it through without embarrassing myself any more than absolutely necessary…

“Honey, such big words!” Mommy calls sternly from the audience. “Remember - you need to be a convincing baby girl!” Oh, poopy. I clutch the pacifier dangling from my dress and jam it nervously into my mouth. Mommy really does want me to do it just like we practiced, doesn’t she? And so I begin again, my stomach knotting as I lisp out the words: “Zhiff iff my pweefentayfhun…on why I neeth my Mommee…”

The mommy dommes are cracking up now, clearly amused at my infantile enunciation - or lack thereof. “I wuv my Mommee tho mush,” I flounder on, blushing, desperate to make it through before - well, before I lost control. “Thee makef me bwekfis’, an feeth me my ba-ba, and dweffeth me in pwitty, pwitty cwoves…” A squeaky fart escapes me, resounding through the thick layers of padding between my legs and provoking giggles among the audience. Oh, yes, Mommy does do all those things. Over the past twenty-four hours she’s been taking special care of me, stuffing me with oatmeal and prunes and milk until I felt like I was bursting… Which, quite literally, was what I felt on the verge of doing right now - in my pants.

“I neeth my Mommee becauth…becauth I’m jufth a-a widdle giwl,” I stammer, shifting from foot to foot, fighting back the urge to clutch my stomach, hoping desperately to quell the growing tempest in my gut. “I don’ know mush, an’ I neeth hew to take good cawe ov me.” My audience is snickering now at my increasingly obvious discomfort - discomfort that Mommy has precisely timed to strike during this little show of ours. Oh, Mommy is so devious. But worst of all, even as I rage internally at how she’s stacked the odds so firmly against me, we both know deep down that I crave this humiliation so disgustingly much…

Then Sheila, the most forward of the mommy dommes, calls out: “Looks like you’re feeling a little nervous, baby! Do you need your Mommy to take you potty?” Oh, God, yes - I need a toilet so very, very badly. But even now…no. I can’t. My cheeks aflame, I shake my head, determined to make Mommy proud. “No, ma’am,” I mumble meekly. “I don’ need da pottee.” “Oh, really?” she asks, clearly amused by my stubborn response. “Why not, little sissy?”

Here it was. “’Cauth I don’ know how ta wooze it,” I lisp loudly from behind my pacifier, blushing as I pull up my skirt and petticoats to reveal the frilly bulk beneath. “Mommy thayth I beewong in dyeputh,” I grit my teeth as another pang grips my abdomen, my sphincter screaming for release. I should, I must. I can’t hold on any longer… can I? But I stubbornly hold out, praying that I can finish somehow before the inevitable explosion occurs.

“Oh, of course!” she exclaims, giggling. “I should have known such a little sissy as you wouldn’t be out of diapers yet.” She cast a mirthful glance back at my Mommy. “But sweetie, shouldn’t you actually show us just how much you need them, instead of just telling us?” No, please. No! I cast a panicked glance at Mommy, begging wordlessly for her to come to my rescue. Please, Mommy, I’m already humiliating myself so much here for you. Please…

But all she gives me is a knowing smile. “But of course, Sheila. Don’t worry. My little sissy needs them more than she even knows - and I’m sure she’ll be more than happy to give us a pretty little demonstration.” She gestures firmly at me. “Go on, baby. You heard the nice lady. Why don’t you-”

Alas, she is too late.

I don’t know whether it’s a subconscious impulse on my part, or whether my poor muscles really have just reached their limit. Whatever the case, even before my Mommy has finished speaking, a series of muffled explosions emanate from under my frilly skirt; and with a sickening, torrential rush, the semisolid contents of my laxative-stimulated bowels squirt messily out into my pants. I double over in mingled pain and relief, clutching the little blackboard prop beside me, suckling instinctively on my dummy and not even caring anymore that I am giving my audience the most delightful upskirt view of my rapidly filling and sagging diapers. I am a messy baby indeed, and now the entire audience knows it beyond the shadow of a doubt.

And I know you were nervous about the whole chastity thing at first but we REALLY appreciate being able to feel safe in our own house. It's a good thing you were tiny enough to fit, huh? I also bet it's rough for you being stuck in that thing when there's a bunch of college girls walking around in our underwear and bringing guys over to fuck. I know we can get a little carried away when we're having our holes filled with loads of cum.

Anyway, since you've been so nice looking after us, we all decided we're going to be nice and look after you... as our new sissy baby!! Yayyy! You don't have to worry about a thing from now on, snookums. You just need to sit back and be da cutest widdle baby guwl and let your new Mommies take care of everything. We'll do the dishes, clean the laundry, pick up around the house...

We'll even change your stinky pampies when you make a boom boom! Oohh I bet the boys we bring over will be SO jealous when they see how much attention you get from so many hot girls.

No you can't change yourself, silly! That's a job for Mommies. Steph was worried you'd be a feisty pansy. Good thing she convinced us to buy those pwetty mitties. They make sure baby can't make naughty grabbies to take off her didees. They also make it almost impossible for baby to make wubbies with her cwitty cage by herself. Which reminds me, how do you feel about a daily milking? Sarah thought it was too much but...

Of course I didn’t forget about putting on your diaper. We don’t want you wetting the bed sweetie. But Mom’s not comfortable with me seeing your PP in her house. So she insisted that she do it tonight.

I know, I’m not super excited about either. I’m fine with her seeing your little penis, that’s not what bothers me. I just hope she doesn’t notice that I’ve already taken your virginity, and then some LOL. Although technically I’m still a virgin. I’d still not like her to notice how I’ve ruined your little hole.

Oh ya, I loved their little nubbies. It’s naughty but I would grind my pussy against their little stiff penis. Nothing get’s me off like that does. Which is why I’m obsessed with guys with little dinkies, LOL. I’m technically a virgin still, I’ve never been penetrated. I’m saving myself for marriage, so you'd have to wear a chastity cage till we did. We can’t have it slipping in on accident! But don’t worry, I can still get off rubbing your hard little caged numb just fine. And I’ll let you out to make cummies often.

Yep, these are all natural H cups. I’ve been doing breast enhancement and lactation induction ever since I learned about it. Breastfeeding would be a multiple times a day requirement. I also have gallons of it stored up in the freezer. It’s very healthy, you’ll love it.

Yep, 24/7 diapers with me. I’ll change every diaper you wear for the rest of your life. Messy diapers are my favorite so no potty ever! Some guys like to sneak and use the potty for number 2, but don’t you try it because I’ll know and you’ll be punished.

Exactly, you would be my boyfriend, and I would be your Mommy. I mean, I’d still sleep with other guys of course. But you’d still get to have sex with me orally. I just need a real man dick every now and than as well.

That’s right, you could tell people I was your girlfriend. You could even tell them we have sex and you’re not a virgin. No one would have to know that you’re actually my baby boy. There is one catch though.

It’s just a minor detail. You’d have to wear a chastity cage 24/7 along with your diapers. Zero potty privilege's, and zero cumming without permission. Mommy changes all of your diapers, and controls all of your orgasms.

The stroller’s wheels squeak softly as Mommy pushes you through the front door, the sound of laughter and chatter spilling out from the living room. You can feel the weight of the thick diaper between your legs, the plastic backing crinkling with every slight movement. The shortalls do little to hide the obvious bulge, the fabric stretched taut over the padding. You wiggle your toes, the socks on your feet feeling absurdly small, like they belong to a child rather than a grown man. But that’s what you are now, aren’t you? Mommy’s little boy, strapped into a stroller, about to be paraded in front of people who once knew you as an equal.

You grip the tray of the stroller, your fingers tracing the edge of the plastic as Mommy steers you into the room. The conversations falter for a moment, then die entirely. You can almost hear the confusion in the silence. A few of your former coworkers glance over, their expressions shifting from polite smiles to outright bewilderment. One of them, Mark, from accounting, does a double take, his beer bottle pausing halfway to his lips.

“Uh…” he starts, then stops, as if his brain can’t quite process what he’s seeing.

Mommy doesn’t miss a beat. She stops the stroller in the middle of the room, her hand resting on the back as she beams down at you. “Look who I brought!” she announces, her voice dripping with that infuriating, affectionate pride. “Say hi to everyone, sweetheart.”

You squirm, your face burning. You want to shrink into the stroller, to disappear entirely, but there’s nowhere to hide. The diaper is impossible to ignore, the bulk of it pressing against the seat, the tapes digging slightly into your hips. You can feel the warmth spreading through the padding, you’d peed a little on the way over, nerves getting the better of you, and the wetness indicators are probably already an embarrassing blue.

“Hi,” you mumble, your voice small, your eyes fixed on your lap.

Mark, your old coworker, is the first to break the silence. He tilts his head, squinting at the obvious bulge beneath your shortalls. “Dude… is he wearing a diaper?”

Mommy doesn’t hesitate. “Of course he is.”

Sarah, from HR, steps closer, her eyes flicking between Mommy and the unmistakable outline of the diaper. “No way. Seriously?”

Mommy nods, her fingers already working at the snaps of your shortalls. “Seriously.”

Jake from marketing crosses his arms, his expression a mix of disbelief and amusement. “But does he, like… use it?”

Mommy’s grin widens as she unfastens the last snap and tugs the shortalls down your legs in one smooth motion. The fabric pools at your ankles, leaving you in nothing but your t-shirt and the thick, crinkling diaper. The room falls silent again as the full sight of you is revealed, the bulky padding, the plastic backing, the way the diaper forces your legs apart.

And then they see it.

The wetness.

The deep blue stripe on the front of the diaper is  impossible to miss, the plastic glistening slightly where the moisture has spread. Sarah’s eyes widen. “Oh my God. He peed in it.”

Mommy chuckles, bending down to pull the shortalls free and set them aside. “Told you he uses them.”

Mark lets out a disbelieving laugh, crouching down to get a better look. His fingers hover just above the diaper, as if he’s afraid to touch it. “That’s… that’s wild.”

Jake shakes his head, his grin spreading. “So he just sits there, in a wet diaper, like it’s normal?”

Mommy ruffles your hair, her touch affectionate. “It is normal. For him, anyway.” She taps the front of your diaper, the squish loud in the quiet room. “See? Nice and wet. Just like a good little boy should be.”

The room erupts into laughter, the initial shock giving way to teasing. Sarah reaches out, her fingers brushing against the plastic backing. The crinkle is deafening. “Damn. That’s thick. And wet.”

You squirm, your face burning, but you don’t protest. What’s the point? The evidence is right there, plain for everyone to see. The diaper is heavy between your legs, the wetness a constant, embarrassing reminder of your regression. But beneath the humiliation, there’s something else, something warm, something comforting. This is who you are now. Mommy’s little boy, diapered and cared for, and if that means being the center of attention for a while, so be it.

The teasing continues for what feels like an eternity. They ask if you can walk (you can, but Mommy prefers to keep you in the stroller for “safety”). They ask if you want to be like this (the answer is complicated). They ask if Mommy changes you (yes, and you hate how much you love it).

Eventually, though, the novelty wears off. The adults drift back to their conversations, work, politics, the latest sports game, leaving you and Mommy on the periphery. Mommy bends down, her face softening as she looks at you. “You doing okay, baby?”

You nod, but your throat feels tight.

She smiles, brushing a strand of hair out of your face. “Good boy. “Now go play.”

Play. The word makes your stomach twist, but you obey, shuffling toward the corner of the room where a few toys have been left out, a stuffed bear, a stack of blocks, a coloring book. You can feel the eyes on you as you move, the occasional snicker, the whispered comments. But you ignore them, because Mommy told you to play, and good boys listen to Mommy.

You sink down onto the floor, the diaper crinkling loudly beneath you. The blocks are in front of you, but you don’t reach for them. Instead, you sit there, your hands resting on your knees, the thickness of the diaper a constant, comforting presence.

Across the room, the party continues. Laughter, clinking glasses, the hum of adult conversation. And you? You’re just… there. A curiosity. A joke. A little boy in a diaper, left to his own devices while the grown-ups talk about grown-up things.

It’s humiliating.

It’s perfect.