Day and (Second) Date

Mandy starts earning her place in my house even before I wake up. When I do, the first sensations I feel are her lips around my cock; her warm, wet mouth; her teasing tongue; her delicate fingers lightly stroking my balls; and her happy little sissy hum.

Today's no exception. I wake up from a half-remembered dream, and instantly forget it. It couldn't have been much better than this.

I lower my hands to Mandy's head, and run my fingers through her mid-length, bottle-blonde hair.

"Good sissy-girl, Mandy," I sigh out.

Her humming gets a little louder and a little happier; it's music to my ears. She knows she doesn't have to use her words when she's servicing me like this. I grip her head and start thrusting my hips. My cock is already hard, but we both like the ramp-up to the main event. I push my cock into her throat a few times just to send the message: I own you. She has no gag reflex left. There's a muffled gurgling noise, and a slight change to the tenor of her wordless tune. The rest of her body actually relaxes when we switch over from a blowjob to a skull-fucking. She slips into sub space very easily.

I can't keep it up very long, though; I'll cum if I do. Her mouth and throat are fantastic, but that's not where my cum goes in the morning.

"Okay, sissy-baby," I say, "get the lube. Time to bite the pillow."

There are plenty of ways to talk about anal sex. Mandy and I like that one the best. It gives both us an extra thrill. She especially likes it when I drop it casually into a conversation with somebody else: "yeah, she bites the pillow for me twice a day, at least." If she's around to hear it, her flawless pale skin turns pink, and she squirms around her plug or teaser. It's adorable.

Mandy already had the lube in her hand. She offers it to me. I take it, and slowly withdraw my cock from her mouth. Mandy crawls up from under the sheet and presents herself. She's only wearing panties. They're dark red, lacy, low-cut bikinis, and they're nearly transparent in several places -- including the rear, so that a particularly-prominent anal plug base would be visible through them. Her perky sissy titties -- flirting with a B cup, and capped with delightful eraser-tip nipples - dangle down, just barely swaying as she breathes. I almost don't want to sit up. It's such a wonderful view.

I do, though, because seeing her face-down, ass-up from above is just as good. I take a moment to savor it. Her exercise regimen has done wonders for her legs and ass. The hormones ensure they stay feminine. Her diet ensures they stay slim.

Then I make the view even better. I shuffle over on my knees, hook my thumbs into her panties' waistband, and tug them down until they're almost to her knees. The base of her plug comes into view. It's a cute little heart, shaped from the same red silicone as the rest of the toy. Well, okay, it's not that little. Her cheeks push against its sides, and can't close around it all the way. That's as much a testament to her ass as is it to the plug, though. It's such a perfect shape, at least in my opinion: tiny, tight, and just a little bit bubbly, with enough flare from the hips to be undeniably feminine. The 'man' Mandy used to be must've been one in a million.

"That is beautiful," I tell her. "That's exactly what a sissy girl should look like." I find a nearby pillow -- already covered with a towel -- and position it underneath her cage. Mandy is very good at preparing for sex, and we both know our morning routine cold.

"Thank you, Master," she replies serenely. "I love you so much."

"Keep being good for me," I say. She nods; she understands. Sissies have to earn everything, every day. My love is a reward. That's how I prefer it, and I hope by now she prefers it that way too.

A year ago, she'd have been a very disappointed sissy. When I first met her, she was looking for outright abuse. I was fine with it for awhile, but honestly, it was exhausting. It was even a little heartbreaking, because Mandy is the most beautiful, most feminine sissy I've ever seen. On top of that, she works hard and she's a great fuck. In just a year, she's gone from burning pasta to making good french toast, and she keeps the house spotless.

Once she got addicted to my cock, I began mindfucking her -- or maybe even reverse-mindfucking her. I steered her away from the hardcore stuff. I played all the usual tricks a master plays to get what he actually wants from a submissive slave. Mandy still gets humiliated regularly; I don't have to do much to make it happen. I talk openly and honestly about our relationship to anybody who's curious. I make her do cam shows every day while I'm at work, in addition to all her other chores. I also make sure to go on dates with open-minded women. The first dates are a minefield, as you might imagine. Mandy comes with me on the second dates. They're almost always fun.

We've got one tonight, in fact. Before then, though, we each have a full day ahead of us.

I lube up Mandy's pre-stretched hole and ease out her nighttime plug. It's fairly long and thick -- just not quite as long and thick as my cock. That would ruin the fun. It's the perfect size to ensure that I can get to the fucking in short order every single morning.

I set the plug on a nearby towel; there's a fresh one waiting next to it for after we're done. I lube up two fingers and slide them inside of Mandy's rear sissy hole. She squeaks, then moans. Her voice stays high, breathy, and feminine. I find her sissy spot very quickly. I tease it just enough to get her hips rocking.

Most masters would swat their sissy at this point. I lean over and give Mandy's pale, perky ass a big kiss. She makes a noise like her heart is melting.

"Such a good sissy, Mandy," I whisper. "Don't you worry; my big, fat cock is going to give your sissy spot a deep massage very soon."

"Oh, thank you, Master," she sighs. "I'm so swollen. I need to be milked."

I rub her ass; I even tickle it with my fingers. She squirms a little, and giggles.

"Well," I say coyly, "I think we can do a little better than just a regular milking."

I can hear the smile on her face. I can picture the sexy lip-bite. If you strip away all the bullshit, we're basically a regular couple who've made compromises with each other for the sake of the relationship. We've always agreed on a few things, though. We agree that I have a great cock, and that I know how to use it.

I lube it up and wipe my hands. When Mandy feels me come closer, she spreads her legs and arches her back just a little bit more. Her head's right on the pillow. She's ready to bite it. She literally does, every morning. It's our fun little routine. I'm actually thinking about buying a bunch of tiny pillows to stash around the house, so that she can literally bite one when I decide to bend her over a table, counter top, or sofa arm.

I grasp her hips and press my thumbs into her ass. I get my throbbing cock into position. Mandy's breathing changes; she's eager, but she knows how to make it seem like she's scared.

"Whose sissy hole is this?" I ask her.

"Yours, Master," she answers. She makes her voice quaver; she sounds defeated.

I'm not cruel, but I'm still a master. I like conquering holes. I like dominating sissies. My cock twitches and swells.

I push it against Mandy's rear sissy hole. The hole itself offers no resistance at all. The inner ring is comfortably snug, but eminently pliable. I claim what's already mine. Mandy bites down, hard, and makes exactly the right noises so that I know she's doing it. She grips at the sheets, and her knuckles go white. She pretends my cock is still too big for her. She's pretty convincing, but then again, my cock really is that big.

The visual is stunning, but I try to focus on the sensations. I angle downwards as I thrust further into her, making sure I can feel my fat cockhead dragging against her sissy spot. Mandy makes more noises; she's not pretending anymore. She feels the sting and the zing. She feels the sudden urge to pee, knowing that she can't and won't. She feels her sticky sissy juice being forced down towards her caged clitty. She gasps, moans, and groans it all out to me.

It's all I can do to keep a slow, dominant pace for a while. She triggers something primal in me. I want to lean over, collapse down onto her, thrust my cock as deep inside of her sissy hole as it will go, and then rut to my own selfish orgasm right away.

I'll definitely do it eventually, but first, Mandy needs some milking. I keep fucking her slowly. I keep pushing down rhythmically, ensuring her sissy spot experiences two distinct waves of pressure and release: sawing and pushing.

"Let it flow, sissy-baby," I tell her. "Surrender your weak sissy juices. Let's get you nice and empty so you can focus on what really matters: serving me."

Mandy nods and moans while her teeth still firmly grip the pillow. Her hips start moving. I ease up, letting her fuck herself on my hard, throbbing cock.

"Aw, sissy likes it," I say condescendingly. "That's right, baby. Your little clitty has to stay locked up. If you want to cum, it's your sissy holes, your sissy spot, or your sissy titties. Work for it. Earn it."

I smile to myself. As good as I am at fucking sissy holes, I'll never be able to milk her faster or better than she can milk herself. It's another one of our very-mature compromises. I don't have to brutally ass-rape her every morning anymore, but I make sure to keep her in the right headspace with plenty of dirty talk.

Mandy's arms twitch. One of them starts to stray downwards. She gives me plenty of time to notice and react.

"Oh, no, no, no," I chide her. I release her ass, lean over, grab her wrists, and pull them backwards. I use my strong hands as makeshift cuffs. She huffs and whines. Her hips go into overdrive.

"Good thing I caught my sissy before she was naughty," I tease. "Touching the clitty-cage is a big no-no, even though it won't do much. I would've had to have spanked your ass raw!"

She's nice enough to pretend she doesn't actually want a spanking.

Mandy and I eventually start cooperating. I can't really see, but experience tells me she's leaking steadily. She gets into a rhythm; I hear it in her noises. I let her enjoy it for another minute or so, but after that, I just can't wait any longer.

"Hands to the front, sissy," I command. "Submit."

I release her wrists, and she obeys. Her arms form two sloppy L shapes to either side of her. Her hands are in line with the pillow she's still biting. I finally do what I've wanted to do for the past few minutes. Soon, all my weight is upon her. I hook my arms under her, and then she collapses prone. Her cage pushes down into the damp towel. Her titties are on the bedsheet; more's the pity I can't play with them right now, but I've got other things to do. I grab her shoulders from the back -- well, her front. I'll need the leverage very soon.

"Time to get fucked, sissy," I whisper in her ear. I stick my tongue out and tickle her there. She hates it, which means she loves it too. I don't abuse that paradox often, but, well, it's fun sometimes. The tongue in the ear gets an outsize reaction for how low-effort it is. She squirms as much as she can while pinned by my body weight. Her teeth finally release the pillow.

"Kiss," I command. She turns her head. I press my lips aggressively against hers. It hurts us both just a little bit. She whimpers.

I start fucking her for real. I seize her lower lip with mine. She squeals and cries. She squeezes her eyes shut, but can't keep them like that for very long. She's so overwhelmed that her eyelids start fluttering of their own accord. She can't control much of her face at all. It simply reacts to whatever she's feeling -- what I'm making her feel.

It took six months, but I trained Mandy's sissy hole and sissy spot. I'm not focusing on the latter anymore, but let's call it Cock's Law: any sufficiently vigorous ass-fucking with a sufficiently large cock is indistinguishable from a milking. Arthur C. Clarke, eat your heart out -- or somebody's ass, I guess? I don't know what he was into.

Thanks to the training, though -- and the cage -- Mandy doesn't merely get milked. She gets fucked to climax. She has a shuddering, submissive anal orgasm, and my relentless fuck-milking makes her buck and spasm through it. Every time my cockhead pushes past her already-quivering sissy spot, her entire body twitches. Pain and pleasure mix together perfectly.

I release her lower lip, and her mouth hangs open. I kiss her neck just as violently, threatening to bite. I want to, but it's too dangerous there; besides, she'll have a collar on most of the day. I turn my head and find that soft spot behind her collarbone. There, I finally sink my teeth in. Mandy cries out in pain, and I cum, hard. I feel pure dominance. For this one moment, I'm the master her old sissy self wanted so badly. For this one moment, I don't feel love; I feel ownership, and the uncontrollable need to assert it. I very nearly break my sissy's soft, pale, delicate skin with my teeth. I wrest my arm out from under her and grab her blonde hair. I push her face down into the pillow. I savagely grunt. I try to push a second load into her by sheer force of will -- a load my balls and prostate won't have in them for another hour or two at least.

I'm a little weird like that. My orgasms feel amazing, but right afterwards, I like straining my muscles to their very limit. I like the way it hurts.

Mandy's crying. It breaks my heart a little.

"I love you," she whispers into the pillow. My heart heals. I bite her somewhere else, but it's nothing serious. It's just a warning nip.

"I love you, Master," she says.

"Better, sissy," I say. I'm still a little out of breath.

We stay like that for awhile. My cock shrinks, but Mandy wills herself not to squeeze it out. I withdraw in my own time, then crawl off of her. I find the fresh plug, coat it with lube, and slide inside of her freshly-fucked, cum-flooded sissy hole.

"Thank you, Master," she says. It's muffled by the pillow. Otherwise, her body barely reacts to the new intrusion.

I get up off the bed, find some water, and take a few big swigs. I stretch out. I feel amazing. Everything is right with the world; my sissy knows her place, and has already done a lot to earn it for another day. I putter around, giving her more time to recover. I pick out my clothes for the day. Then I head to the kitchen, start the coffee, and eat a quick breakfast: a piece of fruit and some yogurt. Of course Mandy should be taking care of the coffee and the meal prep, but you have to be realistic about these things. I've got work in a little while, and we still need to shower.

Mandy pulls in way more money from camming and her little website than I would've thought possible, but she's not going to be supporting herself with it, let alone two people. I'm the earner in the relationship. I have a full-time job, and everything is in my name. On the weekends, Mandy goes all-out with breakfast. On weekdays, well, her master has masters of his own that need him at the office at a reasonable hour. I'm not giving up my morning orgasm. I'm also not waking up earlier. Fuck that.

By the time I get back to the bedroom, Mandy's at least able to walk. She's still cum drunk, and her legs are a little wobbly, but I know she'll be okay. I clap my hands twice.

"Bathroom, sissy-baby," I say. "Time to clean up."

"Yes, Master," she says. It comes out a little dazed. I smile; I take it as a compliment. We both head into the master bathroom.

I order her into the shower while the water's still cold. That certainly helps refocus her. She shivers and whines like a soaked kitten. I step in once the water's warm. I wait expectantly, and Mandy grabs the soap and washcloth. She knows the routine. In a few minutes, I'm clean as a whistle. A few moments after that, Mandy's on her knees, looking up at me with her deep, brown eyes. I smile down at her and sigh contentedly.

"Who do you belong to?" I ask her.

"I belong to you, Master," she says. "I'm your property. Everyone should know."

"Good sissy," I say. I take my cock in my hand, and mark my territory. Mandy shuts her eyes and sighs, utterly defeated for the second time this morning.

"Open," I command. She opens her mouth and sticks out her tongue. I make sure some of my piss hits the mark.

"Clean."

I move forward, and guide my cock to her waiting mouth. She licks and sucks.

"Worship."

I turn around, lean forward, and brace myself with the attached shower handles. Mandy shuffles towards me, and gives me my morning rim job. She only 'finishes' by virtue of the fact that I'm on a tight schedule. I'd have had her do it for another half hour, or forever.

"Up," I command. She stands up. I turn back around. She already has the soap waiting. I take it, and urge her to turn too. I wash my beautiful sissy girl thoroughly, paying extra-special attention to her sissy titties. They get a full massage, and their nipples get teased and tweaked. She squirms a little, but this part of our routine is mostly about pleasure -- well, and about actually getting clean.

Once I'm done, I detach the shower head, flick a setting, and put it up to her mouth. She accepts the forceful stream, swishing and then spitting. I reattach it. Now that I'm sure my urine's gone -- or at least too diluted to smell or taste -- I turn her around, lock her into a tight embrace, and kiss her passionately. She swoons, and melts into my arms.

I break the kiss and wait for her eyes to open. I move one hand to her throat, and grasp it. I move the other to her ass cheek, and squeeze it. She pretends to be scared for me. I let us enjoy the moment.

"Good sissy," I say, breaking the tension. "Your master loves you."

She cries again. She does that a lot. These are happy tears, and they make me smile.

"You know how to finish up, sissy-baby," I say. "After that, it's weekday schedule while I'm gone -- except for our date tonight. My after-work blowjob needs to be quick and intense. Make sure the lube's handy."

Mandy's eyes betray conflict. She loves second dates. She doesn't love penetrating her master and giving him a prostate massage. Sissies' masters aren't supposed to care what their sissies want or don't want, but that's just part of the game. This isn't. I like prostate action with my blowjobs -- at least the ones that are meant to make me cum. When Mandy starts pulling her passive-aggressive shit about them, specifically, I lose my patience. I remind her to be careful what she wishes for.

I squeeze her ass again, hard. I squeeze her throat too; it isn't playful. "Didn't you just tell me you were my property, sissy?" I ask her.

Her eyes widen. Christ, I wish she didn't like this so much. Sometimes the paradox cuts against the master.

"Yes, Master," she answers. "I'm your property." The water spraying down on the back of her head only seems to emphasize the point. She's still my soaked little kitten.

"Well then," I say, "I have a wonderful idea for a cam show today. You're going to tell all of your fans that you were a stupid fucking sissy this morning, and got a stupid thought in your stupid head. Your master told you to get ready to give him a prostate massage after he comes home from his real job, where he earns the real money that really supports you, and you thought to yourself, 'well, I don't really like doing that, because I'm supposed to be a submissive bottom.'

"You see," I continue, "you forgot that you're not a submissive bottom. 'Submissive' and 'bottom' are words that we use to describe people -- sexual partners who are people. You are fucking property. So once you explain all of that to the sad, fat, faggoty losers who perv on you every day, this is what you're going to do: you're going to go around to, say... seven other sex toys I have in this house, and you're going to interview them. You're going to ask them whether they're dominant or submissive, tops or bottoms, and whether they have any sex acts they don't like performing. If you find any that do have any hangups, you can go ahead and throw them in the fucking trash, because that's where defective property belongs.