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Sissy Heaven @sissyheaven

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You need to admire sluts. You need to be mindless and silly. You need to wear too much makeup. You need to obsess over femininity. You need to be a cock princess. That's why you're here. - Sissy Heaven (@sissyheaven)
Femslut21 a classic caption reblogged from monica @sissyheaven


A classic caption reblogged from Monica Maxxxwell.

It’s weird when a caption you made shows up on Tumblr.

Captioning is such a strange subculture.

Hxcgorgeous my fantasies are bizarre but i know @sissyheaven


My fantasies are bizarre but I know I’m not the only one. Reblog the hell out of this please. I wanna be exposed as a cockhole I am.

I have a sort of rule against reblogging something that tells me to reblog it. Or even reblogging something without adding something of my own to it.

Because she isn’t the only one!
Because it helps her realize the fantasy of exposure!

When it started she was slipping hypnotic drugs @sissyheaven

When it started, she was slipping hypnotic drugs in your evening beer, and then whispering sissy suggestions in your ear as she gently jerked you off. You found yourself jealous of her clothes and you didn’t know why. You started mincing and your voice slipped slowly into falsetto. Men at work and in public started mocking and laughing at you, and she made it so you felt an intense desire for any man that disparaged you. You hated every moment, but you couldn’t stop yourself. You’d spend the rest of the day disgusted with yourself for fantasizing about their hard cocks in your mouth.

And then on those nights she’d make you tell her about them. She’d coat her dildo in hypnotic drugs and whisper sissy suggestions as she plunged the dildo down your throat while playing with your pansy clit.

Then one Monday morning you couldn’t walk without heels anymore. Your feet wouldn’t work without them, and so you pranced into work in them. Your boss fired you, and you begged him not to, and told him you’d do anything and finally to shut you up he shoved his cock in your whimpering mouth. You gagged and hated what was happening, but you needed to keep sucking it. And the moment he came in your mouth was the moment you knew you’d be forever addicted to his cum. He offered you an unpaid internship as his personal assistant, and told you if he fancied you he might keep you around.

She found out, spoke with your boss, and then they suggested you ought to get big bimbo tit implants to show him how thankful you were. You hate being a sissy, but you love the dizzy high his jizz gives you, even if you know each load makes you more subservient to him. You’ll wear and do anything if it means you can get the cum you crave


Always fun to see my old captions floating around @sissyheaven

Always fun to see my old captions floating around :)

Youre addicted to femininity you get a buzz from @sissyheaven

You’re addicted to femininity. You get a buzz from applying makeup. Pink is your impulse. Frills are your fix. You peak on rhinestones and feathers. Giggles are your comedown. Cocks are your ultimate high.

Hard truth time you have a rather specific kink @sissyheaven

Hard truth time: you have a rather specific kink. And there is plenty of wonderful things about being kinky, but here’s the downside.

Unless you embrace it–and I mean really come to term, come out, get over yourself embrace it–then you are doomed to shitty sex. I mean that. The kind of sex people leave their significant other over and then later tell you “the sex was awful.” And you nod like you’ve been there before, but if you haven’t let yourself just be, then you have no idea. Shitty sex and these secret jerk off sessions are all you have.

This is your life. You get one of these for sure, and then who knows. Hiding is wasting it. I’m serious. I’m not trying to get you hard or make you come. I’m telling you that if you’re sittting there like some submissive in training that will magically will themselves into full being one day when that wonderful perfect dom like in your head comes a long, you are just fucking with time and running away from desire.

The two biggest doms you’ll ever know are time and desire. Everyone’s their bitch. Your desire won’t got away. Time won’t stop. You get to, if you choose to, share yourself with someone and make then lonely world a little less lonely. Or you get to hide out in some meek corner, probably lying to everyone and yourself, counting life in missed chances.

Yea, it’s really scary to share the real you, but if you ask me NOTHING is scarier than the threat of bad sex until you die.

Dream pink @sissyheaven

Dream pink.

Thanks so much to all you submissivesand the few @sissyheaven

Thanks so much to all you submissives–and the few doms/other that follow me–who submitted their opinion on my costume! I’m going as Barbie! Above is the wig I bought and the outfit I am planning to buy! I’m pretty giddy about it!

Also to be extra silly and get into the swing of things I made a computer background that is absolutely silly. Hooray for me?

As you sit there giggling you realize you cant @sissyheaven

As you sit there giggling you realize you can’t remember your name. You mince nervously across the room, unable to recall the way a man is supposed to walk, speak or act. All you can remember is the overwhelming flavor, and the sense of fullness, the last time a cock was in your mouth. All you can remember is the utter powerlessness, the total vulnerability you felt when he called you a good sissy.

I used to do a lot of captions then i quit but i @sissyheaven

I used to do a lot of captions, then I quit. But I did one, just for old times sake. Enjoy, you lawless image monsters, you.

My sweet babydolls i need your help can any of @sissyheaven

My sweet babydolls, I need your help!

Can any of you help point me to where lovely divas like Nikki Nicole and Barbie Dawll buy their wigs? Or where I can find wigs like these for sale?

You knocked on his door to tell him to keep it @sissyheaven

You knocked on his door to tell him to keep it down. That’s all you remember.

You wake up in your computer chair naked, body shaved and your own jism drying on your stomach. Your net browser has tab after tab open of naked men, erect and ready. You feel disgusted, violated, and frightened. For the next few weeks you desperately try to jerk off to the normal porn you used to love, but you can’t cum. You can barely even get hard to it.

He still plays his music loud, but you don’t dare go back over. You’re afraid of him, you tell yourself, but really you’re afraid of you. Afraid of the naughty thoughts that drift in your head when you hear his music thudding. One time he spent the whole day on his porch, and you called in sick to work. You hid, peeking through blinds to see him talking and drinking with friends.

But eventually your luck runs out. On that day he catches you on your way home from work. Suddenly he’s in front of you. “Slow down, Princess,” he chuckles, “I have something for you.” Your pants reflexively tent when he speaks to you. It’s the first time you’ve been truly hard in months, and that fact makes you want to puke. He grins knowingly, handing you a burned CD with PRINCESS written on it in sharpie. Then he walks you to your front door, his arm firmly guiding your shoulder. “You’re looking good,” he tells you as you walk into your front door, and you realize only then how thin you’ve become. You are supposed to hate this, but you feel delicate and treasured. Protected. And then he’s gone. You want to throw the CD away and move to another city, but instead you slip it into your computer. For hours in a haze you are listening to strange audio files, watching video after video of makeup and dress up tutorials for transvestites. You don’t remember most of what you do that night, but a week later as packages arrive it’s obvious. After that every free moment at home is spent dressing up, practicing, perfecting.

When he finally does knock, you answer the door already prissed out and done up to the tranny nines, ready to go. “It’s time,” he tells you, and you giggle like a ditzy faggot should. You spend the car ride playing with the strands of your blonde wig and staring at his crotch. You hate yourself right now, but his cock is so close and it’s all you can think about. He parks at a warehouse. The parking lot is full of cars and you can hear music pounding inside. He leads you past the leering bouncer and through double doors where you are greeted by the sight of vending booths full of naughty things, dance floors, all kinds of men, and lots of feminized bimbos like you. “Cock hungry,” he whispers into your ear, and you are overwhelmed by need. The desires you felt in the car ride now seem like a joke compared to this.

You wrap your arm around his bicep and point to lingerie vendor. “Buy me something pretty, baby,” you whimper out in a forced falsetto. He does, it’s lacey and white and you love it. You put it on immediately. A passing sissy dressed in all pink tells you it’s super cute. You look to your man. You owe him now. You drag him to a nearby couch and the crowds pass as you snap open his pants and watch his dick flop out. For a while you just stare at it, trying desperately to stop yourself, but your mind and your body insist. You are a cocksucker. You’re starting to drool just staring at it. You take this final moment to touch-up your lip gloss.

The taste is everything you hoped it would be. The saltiness of lingering sweat, that masculine stench that permeates your mouth, the hint of bitter precum. His cock slides deeper in, filling up your mouth. You glance up into his eyes. “Good girl,” he assures you. You feel the thick makeup on your face, the bleach blond hair down your back, the sheer encasing your legs, his manhood between your lips—every little emasculating detail making you hornier. A few people have stopped and are filming you with their phones. You want to make them all happy too, put on a good show. That’s how it’s supposed to work. If a man gives you attention, you owe him a reward. So moan with pleasure and deep throat him all the way. Your eyes roll back in ecstasy. “Like what you see?” he confidently asks the growing crowd. You slide your mouth all the way back off him, strands of saliva glistening as you turn to the crowd with a gleeful smile. Then, you pin his cock to his stomach with two dainty fingers and begin to lick his balls.

He groans with pleasure, and then speaks, “Non-hormonal genetic male 32-28-30, forced fem with original personality intact. Her programming is entirely moddable with a few easy-to-learn trigger words making her versatile and perfect for whatever kink you have in your sick little head.” They laugh. A few are casually jerking off as they watch. “Extensive knowledge of makeup, fashion, and sexual techniques, all driven by a deep seeded need to obey and pleasure you. “ You work his cock faster now, excited for the reward that is coming. “As always, upon sale she comes with the basic wardrobe,” he gasps, “of lingerie and costumes.” His speech is tense and stuttered. “I have. Named her Princess but. You can. Of course change that.” He gasps, then taps you on the head and moans out, “face.”

You take his dick out of your mouth and tilt your face up as you jerk him to completion. Jism sprays out landing half in your mouth and half on your cheek. You guide the stream across the bridge of your nose and up into your blonde wig. All you can think about is the overwhelming flavor of semen, and the feel of it coating your face. You try to get the rest of the load into your mouth. When it’s over you wait to swallow until told. He takes a deep breath, rubs his eyes. You show your face off to the crowd. “Oh and one more thing you won’t find elsewhere: she cums on command.” You have a moment of total clarity just then. Blush fills your semen-streaked cheeks. “Princess, cum now.”

You close your eyes as the surge of orgasm overwhelms you.

You rest the lollipop in your open mouth you @sissyheaven

You rest the lollipop in your open mouth. You tease it with your tongue and then it disappears behind closed lips.

You are just another straight guy. You aren’t into this kind of thing. And yet you are. You are consumed by the need to act as you are dressed: a sissy lost in pink and without any will of her own.

He watches you perform, his erection in full view–your one fixation. Oh God, that hard swollen cock, object of your need and proof of his power.

It’s so hard to even think. You don’t want to think, don’t want to stop yourself, don’t want to do anything other than be at his command, his silly princess and lustful slave.

He can see your obsession in your glittering eyes, and he knows he’s won. He knows you are ready. He’s broken you, destroyed the man inside. You are nothing now except what he needs of you. A prancing trophy of his dominance. A pansy barbidoll fuckhole,  A mouth to christen with ownership.

The promise of cocks trigger your need to further @sissyheaven

The promise of cocks trigger your need to further feminize, and feminizing further enrages your need for cock.

Normally i dont post anything about myself on @sissyheaven

Normally I don’t post anything about myself on here, and that’ll pretty much continue as such, but I just had to post that I just ordered this wonderfully girlish jacket.

Just some sloppy cum hungry faggot now living one @sissyheaven

Just some sloppy cum hungry faggot now, living one load to the next. Making just enough money to keep yourself cute and sissified. It’s pathetic, living like that, but oh god none of the shame and embarrassment matters because the taste of a man’s sloppy load is worth it, the feel of it running down your face.

When you sleep you dream of yourself being covered in jism, twirling your blonde curls, giggling like a ditz.

Just reached 800 followers i am still working on @sissyheaven

Just reached 800 followers! I am still working on a special project for you all, and hoping to have it done around the time I reach 1000 followers.

I know that’s being vague like that is a cocktease, but you’ll just have to deal :P

Youre a helpless sissydoll the need to do as @sissyheaven

You’re a helpless sissydoll. The need to do as your told bubbles up inside you every time you see a hard cock. It’s like a reflex. And now your surrounded by naked men.

You need to be used. You need to be their cum-hungry pink faggot. You wanna be fucked until you forget your name. You wanna spend the rest of your life in a bimbo daze, being pretty and pleasing cock.

Its always lovely to see my work floating around @sissyheaven

It’s always lovely to see my work floating around tumblr!

You will one day look into the mirror and realize @sissyheaven

You will one day look into the mirror and realize what you’ve let yourself become. The last of your masculine dignity will snap with embarrassment and only your sissy lust will remain.

Look its as simple as this if you could help @sissyheaven

Look, it’s as simple as this:

If you could help yourself, if you could control your urges or change them, then you wouldn’t be here in some obscure corner of Tumblr reading this. You wouldn’t wrap your fingers around your dick and yearn for high heels, big wigs, and a mouth full of cock.

So stop acting like some guy that occasionally jerks off to sissy fantasies, because that isn’t you. You are the bimbo princess that must occasionally act masculine.

So stop living your life like a man with a fetish and start living it like a sissy with a guy disguise. Keep up pretenses only when you must. Go shopping,get better at makeup, train your voice, join internet groups, take pictures, go to queer clubs, find a mistress or flirt up a hot guy. 



You know your not supposed to you know how @sissyheaven

You know your not supposed to. You know how embarrassing it is. But the makeup and the nylon are stronger than you are. The brush of the wig against your cheek, the elegant ecstasy of smooth, lotioned skin… Already your dick betrays you.

Being a sissy makes you pathetic, but you can’t help yourself. Sissies never can.

You will turn your body into a plaything for @sissyheaven

You will turn your body into a plaything for others.

You will love being cute @sissyheaven

You will love being cute.

You will love your sissy on sissy playtime @sissyheaven

You will love your sissy on sissy playtime.

You will love deepthroating @sissyheaven

You will love deepthroating.

You will be nothing but a lust addled cum @sissyheaven

You will be nothing but a lust-addled, cum addicted tranny cockslut.

You will crave being degraded and then fucked @sissyheaven

You will crave being degraded and then fucked.

You will be the perfect dicksucker @sissyheaven

You will be the perfect dicksucker.

You will love nothing more than being fucked in @sissyheaven

You will love nothing more than being fucked in the ass while dressed like a total slut.

You will let the commands guide you @sissyheaven

You will let the commands guide you.

You will rewatch all your hypnos @sissyheaven

You will rewatch all your hypnos.

You will adore being naughty and extra girlish @sissyheaven

You will adore being naughty and extra girlish around other sissies.

You will love wearing pigtails and pleated skirts @sissyheaven

You will love wearing pigtails and pleated skirts.

You will do anything to please @sissyheaven

You will do anything to please.

You will crave the taste of cum @sissyheaven

You will crave the taste of cum.

You will always need to be girlier @sissyheaven

You will always need to be girlier.

You will be helpless to resist @sissyheaven

You will be helpless to resist.

You will applyyour makeup heavy @sissyheaven

You will applyyour makeup heavy.

You will be glamorous @sissyheaven

You will be glamorous.

You will be the ultimate bimbo @sissyheaven

You will be the ultimate bimbo.

You will like it rough @sissyheaven

You will like it rough.

You will moan and scream and whimper loudly when @sissyheaven

You will moan and scream and whimper loudly when you are fucked.

You will walk like a girl @sissyheaven

You will walk like a girl.

You will always be a cocksucker @sissyheaven

You will always be a cocksucker.

You will wear the girliest lingerie @sissyheaven

You will wear the girliest lingerie.

You will touch up your makeup instinctively @sissyheaven

You will touch up your makeup instinctively whenever you’re nervous.

You will live for pleasure @sissyheaven

You will live for pleasure.

You will be a silly bimbo @sissyheaven

You will be a silly bimbo.