The Exact Right Place And Time

I move around to the front, and push three fingers at her soft, pouty lips. She opens and accepts them immediately.

"You don't have to say anything," I say. "Show me what your sissy mouth is for."

She locks eyes with me and fellates my fingers while humming seductively all around them. I push them all the way to the back of her throat, eliciting tears. Then I give her a curt nod and pull them out. She lowers her jaw as fast as she can, hoping to avoid grazing any of them with her teeth.

I inspect my wet fingers for a second, then snap them and point to the ground.

Ashley's eyes follow, and she dutifully lifts her leg. She bends her ankle but not her knee, as though I'm about to put a glass slipper on her. She can barely keep her balance, and I let her know what I think of her pathetic effort.

"Sissy toes, Daddy, all pedicured and polished how you like them," she says.

Some days I make her stay like this until she falls, but the throbbing in my pants is turning into an ache. We've got too much more to get through.

I nod, and say "Down."

She lowers her leg, and I make a show of tracing my eyes upwards until they land, with contempt, on her caged dicklet. The cage itself is mostly clear, but the few solid-colored bars are pink to match the collar. A strand of sticky sissy juice is dangling from the pale, limp, hairless thing's downturned hole. The motion of her leg probably coaxed it out.

"Ugh, you're leaking already," I say. "Make a note of where it spilled. You're licking it up later."

Ashley blushes, and looks down at the tiled floor.

"Yes Daddy," she says, sniffling.

I reach out and tap the cage, hard, right at the tip.

"Sissy clitty, Daddy," she sputters, "it's completely useless and will never go inside anyone. It won't stop leaking and spurting weak sissy juices."

"That's right," I say. "The chore that never ends. Not only that, but tonight's a cleaning night, so I have to take the cage off, clean it -- the cage, and the dirty sissy clitty, too - and watch as you fail once again to stay limp for your daddy like a good sissy is supposed to."

Ashley breaks down and starts blubbering.

"I -- I'm so sorry Daddy," she moans. "Daddy's hands just feel so go on my sissy clitty, I -- I can't -"

"You can't control yourself," I interrupt. "I know. But that's part of why you're a sissy, I suppose. If you had self-control, you might have self-respect, and then you might at least have been a femboy who gets to lick his mistress's pussy, nipples and asshole in between fistings and strapon fuckings.

"They're certainly not men," I say, "but they're not... this."

Ashley hangs her head in shame, and waits for me to continue.

"You know," I say, "I even hear some women let their femboy inside of them as a special reward sometimes. It doesn't do much for the doms, but that's the kind of love you can develop for a sub that possesses at least some tiny shred of dignity."

Ashley just stands and sobs.

"At least they get to fuck and suck each other sometimes," I muse.

Poor Ashley doesn't even know what to do with that. Her confusion actually quiets the sniffling and choking for a few seconds.

"You, though?" I ask rhetorically. "You haven't even shown me enough discipline to make me consider letting you massage my prostate while I fuck your throat. I'll have to go find some other bitch if I want that."

Ashley lifts up her head, and begins to plead.

"Daddy, n-" she begins, but then a look of terror replaces the ugly cry-face. She stops herself.

If she'd dared to say the word 'no' out of turn to her daddy, she'd have been in a brand new world of shit. It wouldn't have mattered how hard and ready my cock was.

"Daddy," she starts again, still blubbering, "I would do anything for you. I love you so much. I would learn how to do it ten times better than any other bitch!"

I pretend to think it over.

"Anything?" I ask.

Ashley nods eagerly.

"Okay," I say simply. "Then this is what you're going to do for me. I'm going to take off your cage while I lick and suck on your sissy titties, and while I fuck the ever-loving shit out of your rear sissy hole with my big, hard cock. I'm going to fuck all that nasty sissy juice out of you -- well, at least until you fill up again in a few hours -- and all you have to do for me is stay limp. That's it. Then I'll trust you and respect you just enough to let you massage my prostate while I skull-fuck you, or when you worship my master cock with your sissy mouth."

Hope dies on her face. I savor it.

"Can you do that for me, Ashley?" I ask.

Her pathetic, tear-stained face telegraphs utter despair and total defeat. Her head drops. She doesn't have the will to keep it lifted.

"No, Daddy," she half-sobs, half-whispers.

As mind-broken as Ashley is, I honestly have no idea whether she realizes that I basically have control over her little dicklet. With a few tweaks to her hormones and enemas, I could make it limp forever. If I took a sharp left turn with her treatments, I could probably even stop it from leaking.

I walk over to her and wrap my body around hers.

"Well," I say, "at least you're an honest sissy. That's something."

I let her collapse into me and cry it out for a minute. I begin stroking her hair, and gently rocking her.

"Oh, my sad little sissy girl," I whisper. "I know you're trying. I know. Everyone's trying to make you a better sissy slave for me. Those women at the spa, they worked so hard on you today, and you do keep up with your exercises..."

I can feel the hope rekindling in Ashley's fragile breast. She puts her hands on me and gently rubs and caresses my masculine chest. I feel her puffy sissy lips start to give me tiny kisses there too.

"Well," I say, pushing her away and finding her eyes, "you need a milking regardless, and I might as well get something out of it."

Her baby blues light up, but she catches herself. She tries to look questioning, rather than hopeful.

I peel off my shirt, exposing my broad, well-developed chest. I kick off my loafers, and tilt my head up, so that I'm no longer looking at her.

"Strip Daddy's pants and boxers," I command her, "and then worship his ass."

Ashley drops to her knees immediately and undoes my belt, top button and zipper. She gets my pants down and I step out of them, forcing her to back up awkwardly on her knees. The same happens with my underwear, and she's slightly better prepared for the move the second time.

She looks up at me with wide, grateful, questioning eyes. She wants to know if she should worship my cock or my balls. I tilt my head to one side and give her a stern look, silently admonishing her to remember exactly what I said.

She scurries around to my rear, and I feel her soft hands on my ass.

Then I feel a tickle of hair, and then the awkward shuffling, blowing and rustling of a very stupid sissy.

I heave a big, loud sigh.

"Use a hair tie for fuck's sake, you stupid sissy bitch," I call out.

"Yes Daddy, thank you Daddy," she says quickly, and the hair tie comes off her wrist. Usually the verbal abuse is just a part of the unspoken contract, but sometimes...

I feel her lips, tongue and breath on my hole, and I allow myself to relax. I lower my hand and stroke my semi-hard cock. Those two shuffling steps out of my clothes have set me near a counter, because, unlike sissies, masters are smart and plan ahead. I lean forward a bit and brace myself on it with my other hand.

Since the leash has been either in my hand or around my wrist this whole time, I decide to make it work for me. I start giving it rhythmic tugs, urging Ashley's face ever deeper into my crack, and silently ordering her to redouble her efforts. We're up to three or four things I rarely admit to my sissy: she's gotten very good at worshiping my asshole.

After a minute or two, I direct my sissy to tickle my balls with one hand as I stroke my shaft. I let that go on for one minute more, and then I decide to finish the afternoon off.

"Sissy, lube!" I bark. I drop the leash.

Ashley halts her worship, gets up, and hurries to the nearest cache. I hear the leash end drag on the floor, and chuckle to myself.

She returns with a tube of thick gel and presents it to me.

"Sissy, leash," I order.

Ashley gets on her hands and knees, crawls to the leash end, and -- with some struggle -- picks it up between her teeth. She crawls back over to me and gets up on her knees, in begging position. I take the leash end from her mouth.

"Sissy, all fours," I command, and she lowers herself back down.

I give some sharp tugs and lead her to the bedroom, where I unhook the leash and cast it aside.

"Sissy, milking mat," I command, and Ashley fetches a large, clear, plastic mat from its storage basket.

I ponder for a moment, and decide to prioritize my own comfort.

"We'll be doing face-down, ass-up on the bed," I tell her.

"Oh, thank you Daddy," she says, and she sets up the mat appropriately.

"Position," I say, and she gets into the last one I mentioned.

Ashley is trembling with anticipation and desperate need. She's dripping on the mat; she never really stopped this whole time. She'll be licking up tiny little puddles of sissy juice from all over the linoleum and hardwood after I'm done sodomizing her -- well, after all of her other responsibilities are seen to as well.

I get on the bed and loom over her. Sometimes I tease her for a solid five minutes, complete with swats and taps, but today I'm ready to fuck and cum. I grab her plug -- a nice, big long one -- and slide it out of her. She grunts and exhales. Her sissy-hole stays mostly open, glistening from the lube that was just applied about a half-hour ago, right after she purged the last of her custom-tailored high colonic. Below it, her caged sissy-purse and sissy-clitty dangle, and those viscous, sticky strands are still hanging from the tip.

I open the lube and liberally coat two fingers. They slide inside Ashley's hole with no effort. I use only the gentlest touches, which causes her no end of frustration. She starts to squirm, and I give her a hard warning swat on her butt.

Usually I'd yell at her, too, but I'm just too horny. She'd be able to sense my own growing need in my voice, and that's no way for a master to begin a milking. Milking is a chore that a master does for his sissy, and his sissy must show gratitude in return.

I coat my throbbing, aching cock, and then it's time. I enter, brusquely. In mere moments I'm buried to the base.

"Ahhhhhhh thank you Daddeeeeee!" Ashley groans. It turns into a sissy squeal at the end, and after that the sissy noises never fully stop. They only quiet a bit when I rumble my bevy of commands and degradation into her ear, or when she needs to breathe.

"I want your sissy hole twitching and spasming around my master cock for this whole session," I growl at her, already fucking her asspussy with authority. "I'm going to get some pleasure out of this fucking chore, so help me."

Ashley's already lost most of what remains of her mind. Her sissy hole does indeed twitch and spasm, but I doubt she has the strength or control to actually milk my cock. I pound into her, pushing down while I'm inside, making sure my dominant rod hits all those glands and nerve endings like a stiff finger pushing along the tines of a comb.

"All those women at the spa talk about you when they go home, you know," I tell her. "They have husbands, boyfriends, maybe a girlfriend or two -- heck, they probably can't resist talking about you to anybody they meet. You're hot gossip. You're a completely feminized, completely owned bitch. And to think that two years ago, some people might have mistaken you for a male."

Ashley's already feeling too many feelings and making too many noises to properly cry, but I detect a distinct overtone of blubbering after I start properly tearing down her last bit of hope and defense: the thought that maybe, just maybe, her sissyhood stays a little bit private.

"I'm sure they're torn, just like this whole country is," I continue. "Some of them understand that sissies are a part of nature. The only thing worse than being a sissy is trying to pretend you're not one. The world will eat you alive."

I know I can't keep this up. All pretense aside, this is sex. This is fucking. My sexy little sissy bitch is begging for my superior seed with every ounce of her being, and I'm painfully close to giving it to her.

"Some of them don't, though," I say, almost panting. "They think you're a freak. They don't even want you in prison, getting raped by a bunch of muscle-headed gang members, because they're too worried you'll enjoy it. They want you in a nuthouse. Padded walls. Castrated. Doped up. Lobotomized."

I'd never go this far when my poor, fragile sissy was coherent. She isn't, though. All of this abuse no sooner hits her tiny, masochistic little sissy brain than it's all burned away, fuel for the fire, a bunch of electric signals shooting back down her spine and into her asspussy.

I take my hands off her hips and reach around to grab her sissy-titties. Her blubbering and squealing instantly amplify, then become gasps and howls. Her head snaps up, like a genuine bitch's would, to do the latter. I sink my teeth into her shoulder.

"Ooooooh, Daddeeeeee!" she cries, and I feel my cock grow another two sizes inside of her.

This is going to be a very quick 'milking' -- so quick she'll probably need a real one in only two hours. I release my mouth from her delicate flesh and change positions to get the best angle possible on whatever weak spot my swollen cockhead can hit. I'm no longer rubbing across all of them in a line. With every new thrust, I'm picking one at random and pounding it. If juices flow, they flow. If it's a nerve cluster, the impact of my cock electrocutes her with pleasure-pain.

I punctuate my conclusion with violent thrusts.

"You. Have. No. Idea. How. Lucky. You. ARE."

Ashley's mind melts even more. I see the drool start to drip out of her agape mouth.

"Milk Daddy's cock with your hole, you lazy bitch," I grunt. "Make him cum! Make him cum!"

I was going to cum regardless. She didn't need to know that.

She's also so far gone that she can't do a damn thing except take her fuck-milking like a bitch. I can tell from how her groans, moans, and squeals change that her sissy-clitty is trying to get hard in its cage, and that it's hurting her. That pain is mixing with her feverish anal pleasure; with the shame of being unable to follow her daddy's orders; with the complete emasculation of being a real man's ultra-sensitive, totally feminized fuckhole; and with the abject humiliation of needing her daddy to milk her multiple times a day so that she doesn't go an even worse kind of insane.

"I'm sorrrry Daddeeeeeee" she scream-whines - because she's cumming. She's cumming from her ass, like a bitch, but she's also shooting powerful streams of sticky, dirty sissy-juice from her straining little dicklet. They hit the plastic below her so forcefully I can hear them.

It's wonderful that I've chained Ashley's greatest physical pleasure to guilt and shame and humiliation, but in this very moment I couldn't fucking care less. I roar out in my own dominant, masculine triumph over my feminized sexual property. I grab her ponytail and yank, hard, and I shoot my cum deep into her completely conquered bowels. I collapse onto her. She collapses onto the mat, and I hear the thud of the cage. Luckily for her, most of her sissy-juice shot out to a point on the mat just behind where her cage landed, but she'll still have splotches and streaks of it on her groin and tummy.

We stay there for a minute or two, neither of us daring to speak. She's too afraid she'll say something wrong. So am I; it's just that they're two very different definitions of 'wrong.' Mine includes stupid, counterproductive phrases like "that was amazing" or "I love you."

I finally regain the presence of mind to give my sissy what she doesn't want, but knows she needs.

"You did the best you could," I say. It's soothing, but slightly disappointed. "Daddy got to cum, at least. He doesn't need to go anywhere else to be satisfied tonight."

As is our tradition, I dominantly bite-kiss her a few times on her shoulders and collarbone. Some days I take off her collar -- because what better place to hide bite-marks and hickeys? - but right now I'm just too spent.

Ashley starts crying again. It's a distinct phenomenon from the various wails and howls of her milk-fucking and sissygasm. These tears and sobs derive from that perfect balance of emotions that every master needs to reinforce: shame, humiliation, gratitude, devotion, and a persistent, overwhelming feeling of inadequacy.

Sissies aren't good enough at anything. That's why they're sissies. That's what it means to be a sissy. A sissy cannot get what it deserves; it can only deserve whatever correction it gets. Even that which seems like the worst abuse from the most callous master is really just education. It's a final, desperate attempt to make the sissy better, because all traditional methods have failed. Those final attempts almost always fail, too, but that's what makes every master a generous one.

In case you haven't figured it out by now, all of that is just one giant mindfuck. I just came like a fucking freight train, and I did it inside one of the hottest, horniest, most obedient, most submissive, most anally-receptive bottoms in the whole fucking world. I know exactly what I have. I'm keeping it forever.

For whatever it's worth, Ashley probably gets the most powerful orgasms of any sissy on that same fucking planet - maybe even of any sub or any bottom. I'm on the bleeding edge of better sex through chemistry. Not many people are willing to do what I've done.

Deep down, Ashley knows she's owned not by merely a good master, but an excellent one. I just have to make sure she never finds out how incredible I think she is. That would ruin everything, for both of us.

I lift myself off and out, and sit upright on the edge of the bed. I find the discarded plug, and I slide it back into Ashley's battered sissy-hole. She emits a soft, utterly defeated grunt. I knead her bubbly ass-flesh and give her a few moments; I stare at the brutally-fucked hole until it finally closes enough to keep the plug inside on its own.

"Okay, Ashley," I say, still panting a bit, "you know what you need to do. First Daddy, then the mess you made on yourself, then the mat, then the floor."

Ashley slowly, weakly pushes herself up off the mat, struggling to comply. It's a contest between pathetic sissy limbs and a slender sissy frame. With effort, the limbs do win out, barely.

"Thank you for milking me, Daddy," she says. I can hear every one of those vital emotions in the words, plus her complete emotional and physical exhaustion.

She crawls off the bed, and then between my legs. She pauses just before she begins cleaning off my cock with her mouth and tongue. Her face is a tear-stained mess. There's no running mascara today, but it's something to think about for tomorrow.

"I love you, Daddy," she says.

I look down at her, and, even though I technically don't say anything wrong, well... she looks into my eyes, and I think she knows.

Damn.

I stroke her hair and then pat it. She begins to lick and suck.

"Now, now," I say. "Just focus on being a good little sissy. Sissies are responsible for cleaning up, always, and you've got a lot of it to do."

She continues bobbing her head obediently, and her tongue feels amazing on my sensitive cock. She really does do it better than every woman I've been with. She might even be the best I've ever had.

Owning a sissy is a big responsibility. Owning one like Ashley is very expensive. Even though most of your disappointment will be fake, and even though most of their failures will be preordained by your masterful planning and manipulation, it's still a uniquely challenging relationship to build and sustain. Still, if you're not hung up on being with a 'real woman' or a 'real man,' I think it's well worth it.