The Exact Right Place And Time

Special Thanks to Null_Void, a generous participant in Literotica.com's Volunteer Editors program, for editing this piece. All remaining errors and questionable stylistic choices are the sole responsibility of the author.

* * * * * * *

In another few decades, I imagine that a relationship like mine and Ashley's could be considered normal.

A master like me, and a sissy sub like Ashley, will be walking down the street of some mildly-futuristic town -- you know, the ones where you genuinely start to wonder if it's the hydrocell car or the drive-in theater that's the true anachronism - and most passers-by will barely even notice. The master will be holding the leash or have it affixed somewhere convenient; the sissy sub will be collared, plugged, and/or otherwise bound, with the leash attached to her neck, waist or wrist. They'll go about their business with little more than a wave or a nod from an acquaintance or two. Maybe a friend or colleague will briefly stop to chat. If the sissy sub is free-use, a titty- or ass-squeeze will be the equivalent of reaching out to shake (or kiss) a wife's hand.

Are you scoffing right now? Well, okay. This isn't a dissertation on the psychosexual dysfunction of historical western societies. Do the net-dive yourself and get back to me. Focus on women's rights -- or lack thereof -- and how they intersected with societal norms surrounding traditional het-cis marriages. Use your brain a little bit. I think you'll be surprised at what dots you can connect.

Really, what's the difference?

Well, here's one to chew on: our hypothetical future sissy sub probably had, at one point or another, a lot more say in where she ended up than a hypothetical historical wife did.

As I've said, though, this is no dissertation. This is a piece of smut, so let's get to my smutty conclusion: I'm not sure I'd prefer living in that saner, more tolerant future I just dreamed up, master though I am, and sissy sub though Ashley be. I like being here, in 2067, dancing atop a social pressure cooker that could explode at any moment. I like walking around with Ashley in public right now, always on the tightrope of plausible deniability.

"The collar she's wearing is awfully thick, but it's not like it says "Bitch" or "Sissy" or "Anal Slut" on it, right?"

"...well, there is a tag attached to it. Can't quite make out what it says from here, though."

"Sure, there's a strip or chain hooked onto the collar that goes down her back, but it's not like her boyfriend is holding an actual leash."

"Is that a pathetic, caged little dicklet under her schoolgirl micro-skirt, or is it just how the fabric falls and clumps? Maybe she just has a puffy mound, or a pad, or really thick pubes."

"Well, she's definitely not wearing a bra, but I suppose that's her choice -- unless it isn't. And those breasts, well, it would be terrible of me to think that just because they're a little small, she's more likely to be a sissy."

"Did I just see a hint of a plug between those perky, bubbly ass cheeks, or was it just a part of her underwear? Wait... is she even wearing any?"

"Oh shit. Oh SHIT. She might just be trans, and trying out some kind of schoolgirl-goth-punk look. Oh shit. Wait... what's the difference between a trans girl who's a sub to her boyfriend, and a sissy? Fuck, that's bigoted. I'm a bigot. Fuck!"

I fucking love it. I love that everybody we meet becomes a part of our sex life, whether they know it or not. I love that this place, this culture, this moment in human history has everybody worked up into a perpetual panic that precious few of them fully understand. It's so easy to fuck with my little sissy's mind and reframe all of that social tension as sexual tension, all of which exists as a part of our own relationship.

Every confused glance and every knowing one; every awkward interaction; every bit of strained professionalism; it all comes back around again when I'm balls deep in Ashley's mouth or asspussy later that day. I let loose with the litany of her likely failures in passing; of all the men and women who know she's a completely emasculated slut-slave; of all the old and conservative folks who are disgusted by her very existence; of all the tops who want to fuck her, but would have to deny it if they knew she was a sissy and not a girl; and of all the bottoms who wonder if she's any good -- and if maybe, hypothetically, they could replace her or demote her further by showing me a better time.

The best taunts are always about 'real women.' Once a sissy has given up on being a 'real man,' the next logical step is for them to compete with 'real women.' If you want your sissy to scurry, beg, and weep like nothing else, all you need to do is drop a few hints that they are, in fact, in competition with them - and losing.

The sissy's own spiraling psyche will do the rest for you: what if their master loves bigger tits, but can't stand fake ones? How can their asspussy ever compete with a proper vagina, let alone a 'real woman' who's willing to offer up all three of her holes? Do they smell wrong? Are they still too masculine? They'd better pray their faint memories of having a working penis give them an edge when it comes to servicing their master's cock. If not, they'll be tossed aside and left to the wolves.

As wonderful as it is to watch Ashley's mouth stretch around my cock, to see tears well up in her eyes as I verbally degrade her, and to hear her choking and gagging as I fuck her throat, it still can't compare to the thrill of full-on intercourse with my sissy's overly-sensitive, severely-trained asspussy. My whole body presses into hers, prone on the bed, and I get to rattle off the day's humiliations in low, masculine tones right into her ear. I can see the pale skin of her face get beet red, and I'm close enough to hear every pathetic sissy noise that squeaks out of her expertly-tweaked vocal cords.

Those cutting-edge synthetic hormones and designer enema solutions are worth every Euro, too, because I want my sissy's entire existence balanced upon a razor's edge. Shame and humiliation are vital ingredients. Pain is another, but so is pleasure. Every time I dominate and violate my sissy's asspussy with my thick, swollen cock, I want her to be asking herself over and over again: "why do I like this so much? Why do I need it? Why does it feel so good?

"What is wrong with me?"

That's how you trigger the sissy spiral, all the way down, forever. That's how a master can get away with saying nice things to their sissy once in a while, because sooner or later everything feeds into their confusion and their shame. If being a sissy is shameful, then being a good little sissy is even more shameful, and being a bad little sissy is even worse than that. There's no escape.

She does, by the way -- like it, need it, want it. And trust me, there's plenty of pleasure mixed in with the pain. Indeed, my favored approach to completely conquering a sissy is inflicting a pain-from-pleasure overload. Even if Ashley could think about lying to her master anymore about her desires and her reactions, her body simply can't. Its shameful, involuntarily-outed truths are also plain medical facts.

She's been on the hormones for over a year now, and taking those devilishly clever cocktails all the way up into her colon for even longer. As a result, every single part of her with any passing relationship to sex has been thoroughly feminized. Often, that's an understatement. Quite a few of her bits have been pushed past mere femininity into a brand-new realm of hypersexualized sissyhood. The one exception is her dicklet. It's a core source of sissy shame, and so I'm never having it removed or replaced. As luck would have it, Ashley's was so small to begin with that I didn't need any drugs or hormones to tweak it.

Setting that aside, though, the changes have been significant. Ashley's skin has gotten much softer, and of course I've already had all her body hair permanently removed. Her lips are wetter and fuller; their kisses feel like hot, gentle raindrops, and their suckling feels like a spongy, elastic sex toy. All of her former masculine angles -- few and weak though they were to begin with -- are now soft, rounded, feminine curves. The only part she has to work at is her butt, and I make sure she does so at least four times a week.

The hair that I allow her to keep -- her eyebrows, and what's on her scalp -- are both playthings for the sissy-friendly spa I've found in a nearby town. I haven't settled on any favorite styles yet, but I'm having lots of fun pairing up options with all the revealing, humiliating outfits I force Ashley to wear. In the meantime, though, the spa's staff of 'real women' -- some supportive, some coyly disapproving, some playfully competitive for my affections -- keep Ashley so turned around that they should charge extra for sissy psyops.

Ashley's also grown proper, natural sissy-titties, a puffy A-cup pair that are never allowed a regular bra, and rarely any bra at all. They've been sexually sensitized almost to the point of overload, where she can hardly make up her mind between begging for attention from my fingers or tongue, and begging me to stop once I start. The natural release of oxytocin -- the love hormone -- has also been ramped up. A sissy-titty-sucking session will leave her weeping, shuddering and proclaiming her undying devotion to her master. Even though her sissy-titties don't leak, her sissy-clitty surely does, just from that stimulation.

Her sissy entrance has undergone a similar change to her nipples, though not so extreme; I still want to be able to fuck the shit out of Ashley's asspussy without permanently frying her circuits. Behind the entire length of her rectal wall lies nerve cluster after nerve cluster, swollen gland after swollen gland, defenseless against any invader. Those glands produce constantly, which gets her plenty close to mind-broken if she doesn't get regular milkings. The other side, meanwhile, is primed to send pleasure signals straight up her spine and into her brain.

When she does get milked, her pathetic, caged dicklet oozes and drips almost constantly. That's not enough for me, though, generous and enlightened master that I am. When I full-on fuck her with my dominant cock, I want her to cum -- from her ass, like a sissy bitch, of course, but also with a machine-gun burst of involuntary spasms that strain her dicklet against her cage and send her impotent juices flying. Science and money be praised, that's exactly what happens. I make the center of her former manhood a helpless, involuntary participant in a submissive sexual climax that originates from her new sissy core. The triangle is the key: pain, humiliation, and pleasure. Ruined orgasms are fine for punishment. Real orgasms are how you seize total control. It doesn't work that way for male slaves, but sissies aren't men. That's rather the point.

* * * * *

I picked Ashley up twenty minutes ago from the spa, and I can smell how fresh and pampered she is. Her long, honey-blonde hair has been straightened out completely, and, per my request, a section of it falls over one eye to lend an extra hint of tomboyishness to the final picture. Her blue-plaid schoolgirl miniskirt is one of her shortest, since this outing wasn't really, truly public -- and because all those 'real women' at the spa have let me know how much they enjoy tending to - and psychologically torturing - a little sissy slave. I did let Ashley wear panties just in case of trouble; since I knew they'd be flashing everyone at the spa, I made sure they were as lacy and feminine as possible while still being low-cut and skimpy on the fabric. The bulge from her cage is visible in them, but no one can say for certain what it is without really getting in there.

Ashley's also wearing a thin, tight shirt that doesn't make it to her belly button, and would practically vanish if it got wet. Even under the dry fabric, her sissy nipples would be just barely visible if they weren't excited -- but, again per my instructions, they are. Once the little nubs stiffen and poke out, the thin shirt rubbing against them is all it takes to keep them that way. Unlike with the cage bulge in her panties, everybody knows exactly what they're looking at. Boys, girls, and sissies all have nipples, after all. That's plausible deniability.

That shirt, worn in combination with the severely low-cut miniskirt, exposes several inches of smooth, hairless, flat-but-soft tummy, plus the faint outline of her lower ribcage. Even then, this style of shirt is just a little bit more tomboyish than the blouse that usually completes the schoolgirl look.

The collar is especially dangerous today. Since Ashely is 'out' to the spa staff, and will only be visible to the public for a few minutes here and there, I decided to push the envelope. It's thick and pink, with bold capital letters spelling out "CAS TO DADDY," separated into two halves by the heart-shaped leash link and the full-size ownership tag dangling from it.

Is it a name? A typo? Does the casual observer assume they just can't see all the letters? The latter would be a reasonable assumption, especially with this particular hairstyle blocking the view.

But it could also be short for "Complete Anal Submission To Daddy," and -- what a coincidence! - it is.

Jelly sandals on bare feet complete the look, at least as far as clothing is concerned. The mani-pedi, brow job, and fresh coat of lipstick all turned out great. I only gave her a cursory inspection in the spa's parking lot -- just long enough to get her worried about random witnesses -- and then linked her leash once we got into the hydrocell sedan. It's my own, which offers Ashley the merest hint of relief. There'll be no state-mandated rideshare pings, just voluntary ones. My little sissy will have to pray that my lust for her freshly cleansed, dosed, relubed and replugged asspussy wins out over my desire to be a good citizen.

I'd never tell her, but today it definitely does. My cock is already straining in my pants. The schoolgirl vibe always hits me just a little harder, and -- adding to the list of things I don't admit to my slave - my sissy's slight, pale frame really pulls it off. While science certainly does its part to make her twenty-five-year-old body look more like a college freshman's, it had some help. I picked Ashley in part for her potential. Nature did decent work in spite of itself. Thank goodness there are perverts like me in the world who see something besides failure and disappointment when they catch sight of a soft, petite, feminine boy.

We just pretend to see failure and disappointment, to better torture our sissy slaves.

We're almost home now, and Ashley is squirming, practically sweating. Once again, the 'real women' at the spa put her into a sissy tizzy, and I have no doubt that all sorts of panicky, insecure sissy thoughts are rattling around in her mostly-empty head. She's desperate to know that she's still good enough for her master, but that master has thus far withheld his approval -- even after she was just made over to his exacting specifications, and endured another deep colon cleanse. Meanwhile, her nipples are on fire, it's been four hours since her last milking, and the anal plug's been in her any time an inflatable enema nozzle hasn't. Her panties will be stained where her sissy-clitty's pee-hole is pointed; I'm sure of it.

I pull into the driveway, unlink the leash from the front passenger restraint loop, and silently order her out. She glances for the briefest of moments at the opening garage door, yearning for partial cover before she exits, but she knows she must comply. She gets out of the car and stands dutifully in the driveway, waiting for me to pull in, get out, and come back to retrieve her.

I take a few extra seconds, but, well, I'm horny as hell. I don't even bother scanning for nosy neighbors.

I attach the leash and guide her to the adjoining door. Then we're inside, ready to play. There are windows all over with drapes partially open or blinds halfway up. Ashley knows every single one by heart. They're a source of constant fear and paranoia. I do close the doors, though, because I don't actually want uninvited guests.

"Ashley, present standing," I bark out, and my little sissy bolts upright with her chin tilted upwards. More hair falls down over her face, tickling her nose. Now, in addition to her sissy panic, she's fighting the urge to break position and scratch her itch.

I loom over her with my six extra inches of height. I move the hair away and grip her head, inspecting the spa's handiwork. My sissy is downright beautiful, and could pass anything but the most intimate inspection.

She doesn't get to know that.

"Hrm," I reply. "Well, they did what they could."

Ashley's eyes are already wet.

"Arms out," I order, and she goes into a T-pose.

I inspect each of her manicured hands and then run my bigger, rougher pair all over her arms, back towards her torso. I walk all around her, leering. I make sure to brush against her nipples through her shirt. She can't help but react with a twitch and a whimper.

"Hold still unless I say otherwise, bitch," I growl. "But whatever, let's move along. Strip."

Ashley tries to be careful taking off the shirt, but I clap my hands in warning and she finishes with a yank, causing another yelp and wince. The sandals come next, then the skirt, then the panties. Everything is in a bunch on the floor. The delicate little sissy is shivering, T-posed again and almost bare, trying not to react too much to how her long, straight hair is tickling her back and her front. The collar, plug, and cage mean she's not technically naked, but they're cold comfort.

I begin my inspection.

I tug the leash hard enough that she feels it around her neck.

"Sissy collar, Daddy, to show everyone that I'm your owned sissy bitch-slave," Ashley says.

I let her riff on the dirty talk. It keeps me hard, and it's some of the only creativity she's capable of.

I touch each of her outstretched palms with my fingertips, then push down. She struggles to push back, and inevitably fails.

"Weak sissy arms, Daddy, but soft hands to serve you and please you, all freshly manicured," she says.

I grunt. "You can keep them down."

"Thank you, Daddy," she says.

Next, I run my hands all along her shoulders and back, before giving one of her perky, bubbly cheeks a firm swat.

Ashley almost jumps, but just manages to keep her feet planted.

"Sissy bubble butt, Daddy, that I must always exercise to stay sexy for you," she says.

I scoff at the word 'sexy,' and that almost does it. I don't give her enough time to really work herself up, though. My next swat is on the plug's base.

"Oh! Anal plug, Daddy, to keep my hole warm and stretched for anything you want to put inside of me, and to remind me of the only use I have," she says. The surprising jolt up her spine helps keep the sissy-weepies at bay for a few more moments.

"We'll see," I reply skeptically.

Against all reason, these two words actually seem to increase her resolve.

I'm not sure I like that. I come up behind her and cup her puffy sissy-titties.

She shudders and gasps. I begin teasing them immediately. She groans, and her enhanced nerve endings send urgent, contradictory signals into her useless head: maximum pleasure, tilting over into pain.

"Oooooh," she says, "aaahhhhh, sissy titties, Daddy, ah, ah, I -"

I take one hand off a titty and start smacking her butt again, harder than before.

"Ow!" she grunts "Uh, sissy titties Daddy, to show everyone I'm less male than a femboy, and for you to use however you want!"

The swats stop, and I take another minute to rub and tweak her nipples. Finally I relent, and Ashley can't decide whether she wanted me to stop or not.