Sissy Bimbo Captions

 My personal collection of sissy captions, stories and musings for sissies, their bulls and their mistresses to enjoy. Be a girl, be a bimbo, submit to Alpha Males. 18+, NSFW

[sissybimbocaptions]

[sissybimbocaptions]

All alphas can be daddies!

[sissybimbocaptions]

Ghetto sissy!

[whatswingntenex19]

Costumes http://bit.ly/2NAFR5V

[christisplayroom]

“Curtesy just like me, little sissy! Oh, what’s the matter? Scared all those big strong men over there will see the thick diaper I taped you into under than short little skirt? Honey, a gust of wind came up when we were crossing the street and they all saw what you’re wearing. That big black guy hasn’t taken his eyes off you. Maybe you should go over and say hi. Ok, fine, I’ll help you go talk to him. I swear, if it weren’t for me, you’d still be at home in front of your computer, fantasizing about being a diapered sissy bitch for some Real Man. Come on, sweetie, let’s go meet your new Daddy!”

[justsexyness]

[christisplayroom]

“Come on, wear a diaper for me. Please? It’ll be like truth or dare, but just for us. I promise I’ll keep it a secret. Just think. I’m the only one who will know you wore a diaper. I’m the only one you’ll wear a diaper for. Doesn’t that sound fun? And just think. After you put on a diaper for me, it’s your turn to decide what I put on…or take off. So, are you going to wear a diaper for me?”

[femmified-deactivated20230628]

It’s up! A whole new extra-long chapter of The Special Place, the choose-your-own adventure story where YOU are the sissy baby!

You can play from the beginning or use the new fast-forward system to speed through the early chapters.

As always, would love feedback, and bug reporting, and just chattin’ about ideas, get in touch!

CLICK HERE TO ENTER

[tonilipsticklesbian-deactivated]

"Explain to me why you're not wearing a chastity device."

[wimpe-deactivated20190709]

I know you're just a lowly mere male paralegal in a prestigious firm of female-only top-flight brilliantly-accomplIshed Harvard, Yale, and Stanford attorneys, but I still expect a certain standard of professional decorum, even from you.

So kindly look me in my hypnotic azure eyes instead of flicking back and forth between my coltish bare legs, the tight black leather Milan-made skirt that nicely rounds my perfect arse, and my Parisian designer silken blouse that perfectly molds to my smallish yet firm ripened breasts.

Despite your surfeit of legal training and experience, I know that you did in fact sign your written employment agreement with us.  Whether you read and understood it or not is another matter, and irrelevant to the question at hand.  Namely, why are you NOT wearing a chastity device, as per the agreement?

Oh, I see, it's uncomfortable and emasculating and humiliating, you say?  Especially the attached brass bells what tinkle whenever you walk or move, audibly announcing your presence like a belled cat?

Look, I'm not going to sugarcoat this.  There was considerable resistance among the women to my hiring of this firm's first male employee.  After intense negotiations, your chastity requirement was a compromise of sorts.  Some of the women who suffered terribly at the hands of men, including brutal sexual asault, needed reassurances that you would have active control measures.  Your effeminate appearance and nature and tiny stature were necessary for me to get everyone aboard with your hiring, but in and of themselves were insufficient.  The audible chastity is non-negotiable.I

Yes, I said "effeminate appearance and nature".  Of course, everyone sees you that way because that's how you present yourself.  Good lord, are you really that blind, that unaware??  Everyone here assumes you're gay, or else a hopeless sissy.

I can see from your intransigence that further measures will be necessary.  Pursuant to the disciplinary section of our agreement, I will be installing a shock collar around your neck, and selected colleagues will be given remote controls, so I suggest you be on your most exemplary behavior from now on. 

Now follow me into my private office for your shock-collar installation and calibration, as well as your chastity re-reinstallation.  This time you will not be given your own set of keys; you have forfeited the right to presumption of innocence.  Any release will be at my sole discretion.

No, you silly ridiculous worm, you may certainly NOT quit.  Yes, strictly by the letter of labor law, of course you can legally leave, but as a practical matter I'd strongly advise against it.  I have fabulous wealth and innumerable connections, and I will not abide you proving my naysayers correct.  As CEO, office politics and company optics dictate that my decisions stand.  Including my decision to hire you, a decision which I am coming to regret.

You will either succeed here as my hand-picked male employee, or else you will find yourself kidnapped, then forcibly reinvented as a silk-draped, powdered and perfumed, castrated lady's maid, slavishly serving and being mercilessly whipped by the Aayatolla's first wife, the biggest bitch in Tehran.  Come to think of it, a sissy like you might actually secretly prefer that option.

 Soooo ... Are you coming with me to my private office?  Or do I call the white slave trader for a pick-up and a one-way overnight international dungeon delivery?

Good boy.  Wise decision, maybe you're not quite as stupid as I'd initially assumed.  Do be a dear and hand me my tawse; it's hanging on the wall as you enter the office.  As part of your employee improvement program, we still need to discuss in depth today's rather ill-advised mini-rebellion.

[sissybimbocaptions]

All good sissies need pampers

[sissybimbocaptions]

I'm back! Reblog if you need a big man to protect you ;)

[howyoulikethatp-deactivated2020]

BOUNCE BACK - Little Mix (Official Video)

[furcoatvegan]

2 kewt to not bury my caps with ! 

[sissybimbocaptions]

Aaaah, what looks!

[denverbob]

lois lane - superman

[wimpe-deactivated20190709]

After being kidnapped by evil super-villain Lex Luthor and having his poor neglected formerly-vibrant cock cruelly caged in chastity for three months, unfortunate intrepid Daily Planet cub reporter Jimmy Olsen psychologically cracked under the unrelenting pent-up penile pressure.  Ninety naughty nights of constant teasing of orgasm-less edgings from Lex’s sultry slinky sizzling sexy sister Lena Luthor was enough to take a “hard-up” tormented Jimmy right up to the very edge of the bottomless pit of insanity - only to fall right in when his long-awaited promise of release was somehow delayed “due to unavoidable technical difficulties.  We here at LutherCorp apologize for the unexpected delay.  Try to have a nice day, ya caged loser wimp.”

Then voluptuous vixen Lena then smiled brightly and offered Jimmy a little sweet kiss if he would simply stand in as a dress dummy model for her while she designed and sewed her own quite pretty clothing.  In a near-catatonic state due to his horribly unfulfilled needs, a trembling teary-eyed Jimmy felt compelled to agree.   As he gradually got more and more accustomed to being clad in custom-sewn panties, garters, hose, girdles, hose, waist-cinchers, bullet bras, merry widows, plus tons of fashionable girly outerwear, Jimmy’s sense of masculine identity was catastrophically shattered.  Lovely Lena now totally OWNED his sissy cub reporter’s ass.

Finally, a single ruined hands-free orgasm at the very capable hands of Lena was what permanently sealed Olsen’s fate.  Willing to do anything for even the tiny bit of unsatisfying relief that the pleasure-less leaky dribble provided, Jimmy was easily persuaded by Lena to impersonate Lois Lane, lady reporter.  Same hairdo, same clothing (underwear as well as outerwear), same shoes, same makeup, same nail varnish, same everything.

Setting their clever deadly trap, Lex and Lena arranged for Jimmy (who was now masquerading full time as Lois) to call Superman for a meeting, using the 1938 version of the cellphone (see above pic).  The dastardly duo knew that a smitten Superman could not resist a summons from his paramour Lois, and they figured (correctly) that Superman would be far too much of a respectful gentleman to use his X-ray vision to detect the wholly unexpected “jewelry” encasing the even-more-unexpected appendage hiding provocatively beneath the fashionable skirt of “Lois”.

By clever design, Jimmy’s hidden cock-cage was fashioned from kryptonite, and so once Superman responded to "Lois’s” distress call and was within close range, he became as weak as the chastised sissyboy Jimmy, utterly unable to harness any of his former superpowers.  He was now slower than a speeding turtle, less powerful than a loco señorita, and unable to leap small Lego buildings in a single bound.

Forever imprisoned by Lena and Lena’s lovely lipstick lesbian lover (a traitorous Supergirl), Superman now lives at his former Fortress of Solitude, which has become his new Fortress of Sissitude, where he resides as a permanent sex slave to the women along with Jimmy ("Lois”).  Catwoman and Poison Ivy and Harley Quinn simply can’t wait to come up and visit.

The Daily Planet is still capably run by veteran editor-in-chief Perry White, but it’s now become Metropolis’s most beloved porn and smut rag, with frequent printed updates and erection-inducing photo features on what poor Superman and Jimmy (Lois) are being subjected to now.

[sissybimbocaptions]

This sissy wants to see Wimpe rewrite every superhero story!

[hungry4chocolate-deactivated202]

[wimpe-deactivated20190709]

Hi babe, I hope this letter finds you well.  Since we haven’t spoken, or even had any contact at all since you left the good old U.S. of A. five years ago to follow your dreams of hedonistic narcissistic self-seeking pleasure, I decided to drop you a line just to let you know what’s been happening in my life, should you even still care.  I mean, we were almost married, and I hate that things ended on such a sour note between us.  You were my first real love, and I will ever hold that precious memory in my heart, regardless.

As you can see from the attached pic, I’ve successfully moved on with my life since you up and left so suddenly.  I met a fabulously great guy, an incredibly wealthy successful ingenious software entrepreneur from Martinique.  He’s very athletic, like me, not to mention a full 6′7″, so I can even wear fashionable 4-inch high heels before reaching his height!  Quite a contrast from me always having to wear flats with you but still being a full head taller regardless.

Anyways, we’re living in Palm Springs, married now for four blissful years, with a gorgeous little daughter, but just found out that we now have another on the way!  It’s too soon to know if it’ll be a boy or another little girl, but either way, we’re SOOOOO excited, and our little Jasmine can’t wait to be a big sister!

I appreciate you coming clean to me shortly before our wedding day, about how you decided that you didn’t really want the grown-up adult responsibilities of being a husband and father after all.  Instead, you decided you just wanted to be a big adult baby girl 24/7/365, penis pierced and forever riveted away in unbreakable inescapable tungsten-steel chastity cage, and forcibly dressed in diapers and girly attire, hand-fed by spoon and bottle, bathed and changed and even horribly enema’d by full-time nannies and governesses like a spoiled-rotten recalcitrant little child.

Oh yes, then there were your equally-lurid fantasies of the painful over-the-knee spankings too.  Lots and lots of spankings.  I’ll never forget about all the planned spankings for you, you oh-so-naughty little “girl”.

You know, if this was just going to be a part-time fetish of yours, a means of unwind and escape and sheer fun and thrills on the forbidden wild side, then I’d have been totally down with that.  We could have had our own private dungeon, where I would have been more than happy to bring you innumerable physical and psychological and physiological and spiritual delights to continually tickle, tease, delight and otherwise thrill your heightened sissy senses.  Any role you wanted me to play, any toys or tools, any naughty actions to satisfy you, and I’d have happily indulged you and your very kinkiest whims, your very basest of black desires.

Just as long as your fantasies didn’t so overwhelm you that you could no longer function as husband and father back in the real world, away from the playroom dungeon and out into the light of the real world.

But no, even that was asking too much.  No compromise was acceptable; you had to have it all.  If I had gone through with marrying you and had held fast to my wedding vows, then I, as your ever-present dungeon mistress, would have been every bit as much of a slave as you to that cruel fantasy world.

So anyways, I understand that you completely liquidated your twelve-million-dollar trust fund inheritance, all just to pay some corrupt-as-hell Russian oligarch’s international corporation to assume responsibility for your perpetual lifelong care as an adult sissy baby.  Your family was aghast, and tried every possible measure to get you to change your mind, but in the end, despite their tearful pleadings and, ultimately, angry attempts at legal action, it was your decision to make, and make it you did.

Now these are just rumors, but I heard tell that the old abandoned Soviet-era gulag concentration camp where you and a few other formerly-wealthy like-minded ultra-submissives are being held is actually very un-glamorous, unsafe, unsanitary, freezing in winter, and is nothing at all like whatever your twisted fantasies had conjured up.  Your nurses and nannies are not gorgeous high-cheeked full-lipped luminous-eyed Slavic Instagram models, but rather 400-plus pounders who look like the old steroid-pumped East German “women” divers.  Your sissy-girl lives are a living hell and you long for escape with at least part of your sanity (not to mention your once-ample funds) still intact, but the binding contracts you signed (perfectly legal in the Russian Motherland where you now permanently reside) won’t allow it.

Plus, the total ban on you initiating any outside contact (since “babies” can’t talk, dontcha know), and the extreme secrecy of your remote location makes it impossible for you to reach out for any help at all from us here on the outside.  Supposedly this letter and pic will somehow reach you in your cell crib - we were assured through Russian Mafia intermediaries that it would.

Enjoy your life, my darling.  May everything you ever hoped for or wished about or dreamed of come true for you in every way, today and for the rest of your life.  May your diaper be extra full and especially squishy and stinky.  May your enema nozzle be especially cold and big and ridiculously high-pressured.  May your poor prisoned peenie be particularly throbbing and twitchy.  May your backed-up sperm-packed balls be as round and full and delightfully swollen as deliciously overripe Siberian plumbs.  And may the stinging cuts and bluish-blackened bruises from your well-deserved birch-limb spankings be especially painful.

[female-domination-chastity]

[wimpe-deactivated20190709]

I can’t believe that she so blithely reveals the most private, embarrassingly intimate details of our relationship in such a blase’ matter-of-fact manner, to her friends whom I’ve never even met before, with no more care or concern for my feelings than if she were dictating a simple grocery list.

I cringe whenever she immediately accepts a couples invite on behalf of both of us (without even checking with me first), be it a swanky soiree in a 19th-century hand-carved stone mansion in the Hamptons, or a summer cotillion at a Cape Cod beach house, or an exclusive private wedding ceremony in a sky-rise mid-town Manhattan penthouse, or a no-expenses-spared debutante ball on the grounds of an expansive leafy Westchester County Estate.  These obscenely rich and all-powerful movers and shakers in the political, financial, and celebrity entertainment realms, along with their equally spoiled and bratty children, are all part of her inherited old-money crowd.  Her tribe, her people, NOT mine.

I’m just a regular working-class guy whom she picked up while I worked a side gig as a caterer’s waiter during one of these events.  I was stunned by her bold assertiveness, her beauty, her superficial charm, her unbelievable family wealth and influence.  Initially, I felt like I’d hit the jackpot with the boss’s favored daughter somehow, and kept pinching myself to make sure it wasn’t all just some crazy fantasy dream.

It didn’t take long for my happy dream to become something else entirely, as she gradually revealed her true nature.  Somehow, her razor-sharp wit and wickedly delicious sense of humor and extensive repartee’ skills wasn’t so enthralling when she deftly turned them against me, making me the cruel butt of her jokes and on the short end of her once-favorable comparisons.

Now that she’s had me in chastity the latter part of the spring and most of the summer, I’m forever frustrated and terribly twitchy and desperately horny.  For that reason, at night I’m continually moving, turning over in bed like a log rolling down a steep hill, which strangely enough doesn’t seem to bother her sleep patterns at all.  Instead, she just giggles that she really likes to feel my warm, tightly-caged member fruitlessly, futilely throbbing up against her magnificent creamy ivory thighs and butt.

Damn it, this should NOT be happening!  I’m a good-looking (if I do say so myself) very fit 21-year old in peak health.  I’m not gay, so locking me away and only allowing me a “milking” (i.e. a leaky pleasure-free release, NOT a satisfying sleep-inducing relaxing, soul-refreshing proper-as-shit orgasm) by pegging is excruciatingly emasculating, conniving and cruel.  Once her strap-on induced my involuntarily seeping pre-cum and a little clouded milky-white ejaculate, she sneeringly asked me if I was disappointed it wasn’t a real cock that had done the deed, and laughed at my subsequent tears of shame.

So why don’t I just hire a discreet locksmith to “free Willy” and walk away from a toxic rich-bitch mean-girl like her, you ask?

Simple.  The reach of her family wealth and influence is extensive, to say the least.  My mom’s employment with the state, my dad’s small-business contracts, my sister’s state research funding, all of that could suddenly go up in smoke and throw my already-precarious family’s financial footing over the precipice in a heartbeat.  Oh yes, my rich-bitch girlfriend already hinted at all of that, if only obliquely and not directly.

That’s her.on the right in the photo above, taken at yet another one of this endless summer’s interminable whirlwind of high-falutin’ high-society social engagements.  She only reveals the most hidden humiliating details about me to her closest friends, of which she unfortunately has many.  I have to wonder how many people are now in on it.  When a well-dressed, well-appointed still-quite-attractive forty year old flashes me a lovely coquettish smile from across the patio or from across the dance floor, I have to wonder: is she smiling at me because I’m young, handsome, and fit?   Or because she knows the terms of my slavery relationship?

So certain was I that she innately despised me (and why shouldn’t she?  I proved myself many times over to be a pathetic sissy wimp when it came to standing up to her) that I was mentally preparing for her to dump me just as soon as this super-silly season of sizzling summer soirees was over and the rich went back to whatever constituted “normal life” for them.

So imagine my surprise one evening in bed when she absolutely floored me by presenting me with a hideously-expensive ladies’ solitaire multi-carat diamond engagement ring, sized perfectly for my ring finger, and did not ask me, but rather TOLD me, that we were going to get married.

Whoo boy, a life as the rich bitch’s sissy-assed bitch.  Totally didn’t see that coming.

[thepinkfog]

[wimpe-deactivated20190709]

Hold still now, be patient just a sec longer while I finish zipping up your dress recital costume … there, perfect.  Oh, it’s just too-precious-for-words!!   My sweet sweet Jeremy I must say you are the very picture, the quintessential essence, the true representative of classical femininity and grace.  I have had many genuinely female students, but you, my love, despite your Y chromosome and accompanying twig and berries, outshine them all in feminine appearance and deportment.  You bear no resemblance at all to the stubborn, spiteful, angry, rebellious young hellion of nine months ago.  I vividly remember those big burly ill-mannered court officers laughing and mocking you as a “soon-to-be-sissy” as they forcibly dragged you here into my dance studio under mandatory court order, courtesy of the brand-new experimental juvenile delinquent mitigation strategy.  Man oh man, did we ever have to upgrade our physical security to keep you from escaping?

But then, wonder of wonders, miracle of miracles, against all expectations, against all  odds, who could have possibly predicted you’d turn out to be the most natural of ballerina bunheads.  You took to the unyielding discipline of ballet as a duck takes to water, and we soon had you transformed into a lovely elegant swan, not as though you ever had any choice real choice in the matter.  It was either here or the toughest boy’s toughest reformatory for you, and I know for a fact that it would not have turned out well for you there.  No siree bob, not at all.  I think you were aware of that, and that’s why you worked so diligently to fit in here amongst the girls.

Speaking of “fitting in”, you DID remember to put on your tight dancer’s gaffe tonight, right?  Oh, good!

I know it was incredibly difficult for you since you grew up with and went to school with so many of the very attractive female students here, and you had to endure the indignities of them knowing all about the silken finery you had to don, both underwear as well as dance outerwear.  I encouraged them to call you sissy and taunt and mock and berate you at every turn, because that’s what the judge’s sentencing guideline called for.  Oh sure, they may still giggle and point and gossip and show you their exaggerated limp wrists, but by and large you’ve won them over, and they basically accept you as one of them.  I  knew this to be true when I noticed that they no longer bother covering up while changing in front of you anymore.  They no longer see you as a guy, in their eyes you’ve regressed into a soft, sweet-smelling no-threat mama’s boy pantywaist sissy.

Oooh, hear that?  It’s the orchestra’s opening number, the prelude to your show-opening solo dance, so let’s go get you into position to enter the stage when your cue comes.  All your old male classmates, sports teammates, coaches, boy scouts, etc, are out there in the audience tonight to see the new you.  In fact, community interest in this recital has been unprecedented, thanks to you.  We’ve sold out every night’s performance, which has never happened before.

You’ve won the hearts and minds of the girls, now let’s see if you can do the same with the rest of the community.  Break a leg, Jeremy!

[frsgump-deactivated20190925]

[wimpe-deactivated20190709]

Oh hello there Jeffrey, I’m so glad I spotted you!  You really need to be more careful about carelessly wondering off the marked hiking trail.  When your frantic girlfriend reported you missing, then a whole bunch of us volunteered to spread out and start a thorough grid search of this entire extended recreational area.  Hey, I’m really sorry if my off-road vehicle’s loud engine startled you so badly.  I’m sure it can be kinda scary for a lil’ fella like you if you’re not used to hearing it  - now, now sweetheart, no need for tears, and certainly no need for you to lay down in the fetal position, suck your thumb, and curl up in a little ball like you’re doing.  I promise I’m not gonna hurt you honey, cross my heart and hope to die.  I’m your newest bestest friend, and I’m here to help.  My name’s Cassandra - my friends call me Cassie for short, and since we’re friends now, you can just call me Cassie too, okay baby?

I know, I know sugar plum, I’m awfully dirty, filthy from head to toe.  It can’t be helped since intense wilderness “muddin" will do that, but I promise - pinky swear - nothing wild on the way back!  I’ll go super-duper slow, you just hang on tight to me, even though I’m icky-muddy.  No problem - we can wash you off back at the trailhead, where your girlfriend and a park ranger are anxiously waiting for word of you.  She’ll be so happy to see that you’re safe and sound, she won’t even care that you’ll be a wee bit dirty.

So how old are you, sugar lump?  Eight?  Nine?  Oh … wow.  Nineteen?  Yikes, I mean … hmmm, I see.  Err, sweetie pie, I can’t help noticing, are those crushed velvet back-buttoning skin-tight high-waisted legless shorts, with your white nautical sailor-collared blouse’s - err uh, I mean your shirt’s bottom hem buttoned directly underneath them at the waist?  And you’re also wearing scrumptious frilled ankle socks along with with classic black patent leather single-strap Mary Jane shoes?  Wow, just like I used to wear way back in Kindergarten and early elementary girls’ school.

Well, at least I see that you’ve got a pretty dolly with an outfit just like yours to help keep you company so you don’t get too scared whenever you find yourself all alone, like you were just a minute ago.  She’s very pretty - oh, she’s a he?  Well, now that I think about it, that makes perfect sense, I suppose.  Oh, and you sewed your dolly’s outfit all by yourself?  Oh, so you had some help from your mommy?  Well, together I must say you two did a fabulous job.

Okay, stud muffin.  You and your dolly hop up here behind me and hang on.  Miss Cassie’ll get you back straightaway - this wilderness is no place for someone like you to be alone.  What’s that?  Oh yes, my mistake hunny-bunny, this wilderness is no place for someone like you and your dolly to be all alone.

Incidentally, I’m curious, macho man.  Was it you, your girlfriend, or your mommy that dressed you so … er, nicely for the day’s outing this morning?

[bulliedbybrats]

You turn into a little beta wimp when I flash my ass to you 😂😂😂 such a loserrrr! Look at you! Humping the ground in your pampers 😂 WHAT A FREAK!

[kayleethelittlesissy-deactivate]

Mommy makes me wear the prissiest little dresses with a fluffy diapy underneath every day of my life other wise she will punish me, but I love wearing my diapys and dresses!