Silly Sissy Captions!

Everyone thinks their secrets are still secrets. It’s a convenient little delusion that allows them to live dangerously without ever considering the consequences. Worse still, much worse, for spoiled brats, who think everyone loves them and respects their wishes no matter how much gossiping happens the moment they leave the room. This phenomenon was to be the complete downfall of Prince Henry of Pillipulia.

It was just the women in court, he told himself. Just the ones whose clothes he’d secretly borrowed, the ones who he tried pitifully to take as a man only to confess, whimpering, that he would rather wear their petticoats than fuck under them. The silly thing didn’t even think his Father, the King, knew. Of course, he did, and unable to look his swishy son in the eye and admit to him he knew, he was off trying to find an alliance to secure their future when he was captured by the armies of one of their adversaries, King Harald. The King knew of Prince Henry, and wasted no time seizing the opportunity to confront the newly elevated and very, very weak young Prince. He arranged a Royal meeting, to negotiate terms of Pillipulia’s total surrender.

“I could do this the hard way, you know. But if you want to go down that road, let me ask you, who would fight for a sissy like you? Who would sacrifice themselves so a prissy little prince-turned-princess can swirl and mince about? Isn’t the mere fact that I know this fact enough to assure you that everyone could know? You’ll end up the same way, the feminized toy for a man... only question for you, is would you rather that man be me, and you may continue as Princess, or if that man should be the lowest of my guards, perhaps even one of my slaves...”

Every word of counsel from Prince Henry’s advisors, on how to be strong and negotiate forcefully fled his mind, replaced with the natural submission of a true sissy, one who was being ordered and demeaned by a man. A man who would humiliate the Prince. Who would force him into service, as a proper Princess, despite any protestations or whimpering or pleas... it was enough to... oh my gosh!

Prince and King stared at each other in mutual shock as Prince Henry’s attempt at a confrontation ended, entirely, with the Prince spurting down his pant leg, his body convulsing and eyes tearing up as he displayed such pathetic weakness in front of a truly dangerous rival. Word spread far and wide that not only had the Prince surrendered, he’d spilled the final seed of his royal line into his breeches.

Two years later, Princess Henrietta’s shame knew no bounds. Her Father toiled as the lowest of servants, working with the other women servants laundering and cleaning in the castle. Her former Ladies of Court were now her handmaidens, each of them charged with the ruthless enforcement of the Princess’ feminine life. Their treatment of the Princess was informed by each maiden’s personal mixture of scorn and pity.

Her husband, King Harald, ruled her birthright with an iron fist. His soldiers were prioritized, meaning any Pillipulian male was second in line for the opportunity to breed with his own wife. Princess Henrietta was to be the role model for dozens of weak men like him, all who would become feminized brides to their new rulers. Henrietta, of course, was perfectly sculpted by priests, handmaidens, and even women who claimed to be witches to become the perfect, and plump, manifestation of the Princess her King desired.

“Now we HAD to get the boring stuff on the agenda out of the way, because we all know why attendance is so high tonight,” Hayley Howard, School Superintendent for Roscoe County, said laughingly into the microphone to a huge laugh from the crowd. “Now, for those of you who don’t know what I’m talking about... where the hell have you been??” Another big laugh. “Okay no seriously. It’s been a minute. Let me give just a little background...”

“So, let’s start with the worst part: my ex-husband, who most of you will know as Spencer Holcomb, had this job before me. You all know this, and I’m grateful for how welcoming you’ve been as I transitioned from Principal to Superintendent. Now, my ex-husband had a few secrets. Where to begin...” More laughs. “WELL, number one: he was spending school resources on sissification! Big word, that means turning yourself into a mincing, caricature of a woman, submissive and hyper-feminine. More hyper-feminine than me, or any of you, trust me!” Guffaws and gasps burst out from the crowd as Hayley walked through the sordid details. “Now, stealing money for this ridiculousness is a crime. What’s worse, is when that came out, a little more scrutiny revealed that he was even more of a liar, Mr. Smarty Pants was a high school dropout who’d faked his college degree to come work in our little district. Another big no-no!”

“SO! We hashed things out, girl to girl, and arrived at a perfect solution for all involved. I took his bank account and made his dream come true, and you’ll see in a second, his dreams came TRUE. But that’s not enough. We all know how important it is to educate yourself, and a high school diploma is a must-have for success. So, we agreed that Spencer would need to go complete his education. Now you’ll all meet the new Spencer here in a moment, but we wanted to leave this up to a vote. Obviously it will be a little disruptive for a former authority figure to re-enter the classroom as a junior at our High School. I’ve heard from many of you who think this is a perfect punishment, but if the vote is less than unanimous, we won’t do it! So... Steffi, come on out!”

To cheers, whoops, and sarcastic applause, Steffi strutted out wobbling on her heels. The former Mr. Holcomb had met everyone in the crowd as the superior, smart, sarcastic leader he’d pretended to be through his short career. Now, his secret was out... and he felt like his heart was going to explode! His face was flushed, he had cold sweats, his heart was racing... and of course, Hayley couldn’t have looked more beautiful and in charge, commanding the room completely while he surrendered to it.

Everything Hayley had said was true, of course. Spencer, or Steffi, was no stranger to the irony that he fantasized about being exposed as a sissy ditz while actually having a major lapse in his own qualifications. The one insecurity fed the other, he always supposed. Now, those feelings were ruining him.

“Anybody have any questions before we vote?” Hayley laughed from on stage. Hands shot up across the crowd.

Ryan Morris, coach of the football team, asked jokingly “So, does this mean you’re single?” Hayley winked and laughed. “YES.... technically I’m now even a single mother!” More laughter.

“That’s quite the hairdo! Is that a wig?!” Joanna Musgrave, local queen bee and Mom of 4 with a big blonde hairdo of her own, seemed genuinely impressed. “Well of course! No expense spared! We liquidated all his male possessions anyway, so we had quite a lot to work with! Thanks again to Coach Morris for buying Spencer’s old car for his daughter!”

“Where’s she living now?” A cute young english teacher asked, sincerely. “We re-did the guest room! Thank you to those of you who donated some things your girls had grown out of...” More winks and laughter as some of the Moms in the crowd giggled knowingly. Steffi’s new room was overlflowing with ridiculous girly toys, posters, leftover makeup and accessories, all sorts of things that would have made Spencer swoon when he was a closeted sissy. Now that he was living as one, it all felt... so ridiculous! So tacky! It almost felt as if he’d swapped being a closeted man who had sissy fantasies for being an open sissy with fantasies of being the adult man he’d once been! He trembled as it really hit him, what a terrible mistake this had all been, he’d gone along with the punishment Hayley had suggested because it tickled his sissy fantasies but it was so real, this wouldn’t really happen, no way, it- Just then, as he looked over the crowd, he realized every single one had their hand up in the air.

“Look at this room!” Kristi giggled and spun around the hotel suite, giving her newlywed husband a view of her perfect ass in tiny shorts as she admired their view of the ocean. “This is perfect!” Her giddy tone became slightly more serious as she saw her husband’s expression... somewhere between a whimper and a grimace? “Oh darling, don’t think I don’t know how hard this is for you, and I love you so much for doing this... for us! We deserve a vacation this nice, and you made it possible.” She winked and giggled, putting her glossy lips to his. “My little... provider!” More giggles, and these felt a little meaner.

Provider was about the meanest thing she could say to Brian. Brian wasn’t providing anything. Their Daddy was. Brian and Kristi had been having... bedroom troubles. Brian was sweet, he was helpful, he loved Kristi dearly, but he not only was... poorly endowed, he was generally just not up to the task of pleasing a girl like his then-fiancee. She tried idea after idea, and while buttplugs and pegging certainly made her man squeal and spurt, it didn’t help her much if he went from lasting 2 minutes to 30 seconds just because his rear end was stuffed. Kristi’s spicy online stories drifted from her usual fantasies of masculine men,enemies to lovers tropes, princesses and warlords... they never really fit her actual sex life anymore. Instead, she explored stories of cuckolding, men who took the dominant role in a loving but unsatisfied couple. In every story, both wife and husband ended up better off for ceding authority to a man. Brian would hear her vibrator running, and was aware this was the direction her fantasies had taken, sneaking looks at her phone when he felt weakest...

Brian had been struggling with fantasies of his own. Kristi pegging him had unlocked a submissive side that had been trying to burst out ever since. Quickly, he went down the rabbit hole from pegging, to cuckolding fantasies of his own, to sissification, chastity, denial. The little rule-follower began imagining a man who would enter their relationship and enforce all kinds of strict, humiliating, and punishing restrictions on him while Kristi lived her best and most well-fucked life...

When Kristi suggested they explore on apps, just for fun, each of them knew it was much more serious than that. The very first night, he licked her to orgasm while she messaged the man who would, eventually, become their full time and only Daddy.

And Daddy was perfect. Muscular, tanned, early 40s, divorced and very wealthy. Oh, and he loved rules. And even more than that, he loved sissies. How easy they were to toy with. Kristi loved his energy. She loved Brian romantically, of course. But Daddy was like the man from her fantasies. As the wedding approached, he took opportunities to exercise his control and authority over them both more and more. Every important milestone as they prepared for the wedding, Daddy would find ways to insert himself and humiliate Brian. He made sure to fuck her the afternoon just after she tried on her wedding dress, while Brian was forced to go to his own tuxedo fitting wearing a very tight chastity cage and panties. He even played a very dangerous game with Kristi on her bachelorette party, showing up as a stranger while she was bar-hopping with her sisters and girlfriends in Nashville and flirting hard over the night. Their chemistry was so obvious and hot, Kristi was forced to spill the truth to her group of girls... all of whom were totally supportive, after lots of laughter and teasing, and agreed to keep the secret. Mostly. From her parents, at least!

Then came the most escalated demand. Daddy would pay for the honeymoon. In fact, he’d pay for a whole new honeymoon at a luxury beach resort in the Caribbean. On one, major, condition: Brian would spend the entire honeymoon in his sissy-baby-wardrobe. What wardrobe, Brian had asked incredulously? Well, that would be arranged as well. Kristi, in a stroke of cunning, made the decision totally up to Brian... and how could he say no?

“You know, one day, I’ll be able to pay for a room like this for us... once I’m further along at work...” Kristi spun around with an expression of genuine surprise. “You don’t think so??”

“I- I’ve literally never thought about it! You’ve never talked that way before!” She appeared to think for a second. “Don’t... I wouldn’t talk that way in front of Daddy when he gets here. I don’t think he’d like it. Seriously. Daddy hasn’t sent his list of rules yet, but I’m going to guess comments like that would break at least a few of them...”

Marcus Willis Jr. had it all. Millions in NIL deals before his 22nd birthday, a guaranteed ticket to the NFL, and a father who’d played 11 years in the league guiding him. He was the perfect prospect and expected to go in the first round. There was only one real question mark as teams evaluated him. And it was a little awkward to talk about, but that didn’t stop the rumor mill.

Was Marcus dating his... sissified stepbrother?

The facts were undeniable. His Father had married a gorgeous ex-cheerleader when Marcus was in high school. She’d brought with her a nervous son, then going by Liam, 18, who was described by his former friends as smart but reserved... certainly not the type, they all said, that any of them would have expected would transform himself into a bubbly blonde, or certainly start dating a guy like Marcus!

These days, Lila was sweet, bubbly, beautiful, still reserved but very friendly, and absolutely adoring. Her TikTok was all dance videos and cute fits for Marcus’ games and events, the comments almost entirely supportive, definitely some naysayers and haters, but Marcus was too good a player for any of them to come from his fans.

The problem, for some, was the way he talked about it, when asked. He’d almost always defer and move on quickly, but with little hints. “Yeah, well, she learned what a man is,” he’d say. Or the remark that really raised some eyebrows: “I really don’t see the big deal... white boy, white girl, what’s the difference?”

Some of the more conservative, and more white, voices in the draft tried to object. Would it make other players, some in particular, uncomfortable to play with someone who held such a clearly... dim view of white masculinity? Those objections may have held back a lesser player. But the fact was, Marcus was too good to turn down. Worse still, he knew it, and had no intention of hiding his sissy away from the world. Even if he wouldn't discuss her in detail, she was nearly always there, and as the draft began she looked gorgeous and didn’t leave his side. Even some critics had to admit that she did seem to truly support him...

Ultimately, none of it mattered. The crowd burst into applause as Marcus was drafted in the first round. Cameras watched as he gave Lila a big kiss and grabbed her tightly as he walked up onto the stage. Millions saw a loving, gorgeous, submissive sissy on the biggest stage.

What would happen if she got even more popular? What if she started going on podcasts and tiktok and getting into much more detail about how she made the choice to go from reserved young man to girly-girl arm candy? Would people start looking differently at their boyfriends, or their sons, or their friends? Was that really a discussion that anybody was ready for?

1

“Absolutely it’s going to be embarrassing. Fucking absolutely embarrassing. That’s the point. You embarrassed me by having an affair with that stupid girl. You made me have to walk around places being gossiped about. After this, we’ll be even. It’s just one time, you won’t know the man, and it’s just for you to see that I can still put you in your fucking place if I want to. Otherwise, I have no power in this relationship. So that’s it: take it or leave it. But if you leave it, I leave you.”

That fucking BITCH! Ryan Fisher was furious. She never should have found out that he was fucking his assistant. It was all her loser of a boyfriend’s fault, what kind of man DM’s the wife of another man and gossips like this?? But... if Sarah left him, it would cost Ryan a fortune. Not to mention, be quite personally embarrassing, far more so than a little private moment he could forget about, even if it sounded fucking humiliating. So, Ryan agreed.

Sarah insisted that he do his whole Salon routine across town and drive him to and from before her date came over, a humiliation that was not part of the agreement and had left him feeling small and pathetic. As he rode back after a humiliating trip to a fancy wig shop to buy the ridiculous blonde updo perched on his head, he tried to reassure himself. He was going to watch his bitch of a wife get plowed by some loser, he was going to wash all this ridiculous shit off, and when he fucked Marissa again he was going to do it twice as hard, whether that boyfriend left her or not... thoughts of her sweet, perky tits danced in his head, that feeling cruelly interrupted by the small plastic chastity cage Sarah had insisted on as part of the fantasy. It made him feel so much more the part, a feeling that was intensifying as he awkwardly got out of the backseat of his own car, as Sarah had insisted upon. She hadn’t said a word, simply giggling and dancing as she drove to various sexy girly pop songs to hype herself up, each one more grating to Ryan.

So far, it was honestly a lot worse than his worst fears. And why had she insisted on this style?? He knew he’d be dressed as a girl, but this was like what a cartoon doll might wear!! So... juvenile, or vintage, or... it was somehow so much more emasculating than simple girl clothes... the way the tight bodice constricted his waist, the swish of his petticoats... he was about to watch a man fuck Sarah?? The deed taking place before Ryan could even have a drink or two to settle the fact that he was about to enact some kind of sick cuckold fantasy was trouble enough, just the idea of spending another second like this was horrible...

“One final little touch!” She giggled as she walked ahead of Ryan, still humming some Daisy Carpenter song with her hair bouncing. “Tonight, you’ll be named Lucy.” She burst into a big giggle. She was in way too much of a good mood for Ryan’s taste. And Lucy?? What the fuck?? He felt faint as Sarah open the door, striding inside, and then- 2

“Oh, HONEY!” Ryan’s jaw dropped as his Mother stood in the foyer, beaming and a little giggly, her arms open to give him a big hug! “Welcome home!!! I hear someone had a big day!!!”

Ryan looked around, his heart racing and head spinning. Behind his Mother stood his sister Kayla, the middle child, on the left, gasping and giggling. Behind her were two of Sarah’s friends, then his youngest sister Chloe, then Sarah’s sister Brielle... no, no no NO, this was bad, this was... standing right next to his Mother, Sarah held a smug expression that made him want to faint. This was a fucking setup! This was all- wait, if this was a setup, then they all think...

“My sweet Lucy!!! I can’t believe it, you’re so beautiful!!!” As his Mother wrapped Ryan in a huge hug, Sarah cheekily addressed the girls in the room.

“Our sweet girl here begged me to find a way to ask his Mommy what he would have been named had he been born a girl! Isn’t it such a pretty name, and finally put to use, isn’t that right Mrs. Fisher? Sweet Lucy here practically burst into sobs the second she heard it! Said it was the most beautiful thing she’d ever heard!”

“Well we’re all very happy to welcome another girl to the family!” Chloe giggled. “Plus, I’m not the youngest anymore!” Ryan stifled a whimper of confusion, still being held tightly.

“Oh yes, just so everyone knows, Lucy here feels it’s most appropriate, given her late blossoming into girlhood and her delightfully juvenile fashion sense that the family structure be re-oriented so everyone considers her the youngest sister.” One of Sarah’s friends nearly choked on her laughter, before managing to yell out a giggly “Makes perfect sense to me!”

“ME TOO!” Ryan’s mother squealed. “We’re all just so happy to see you embrace yourself... you’ve been so miserable these last few years and now we know why!! And as usual your PERFECT w-wife... well, we’ll have to figure that out,” she said, turning to Sarah warmly, “has helped us all understand so we can best help you!”

“H-Help understand...” Ryan spoke his first words since walking in the door, in a meek but still his own voice that caused the girls in the room to giggle further and whisper how that would need to be worked on.

“Yes, dearie!! Your Father couldn’t be here, and he’s going to need a little help adjusting, but he volunteered to handle your work for you! In fact, he’s there now getting your things in order!” Ryan’s stomach dropped. This was going from humiliating to apocalyptic.

“My t-things?” Another giggle from the group.

“Hehehe! Don’t worry dear, not your things, heaven knows how traumatizing those “Ryan” things and tasks must be for you! He’s simply explaining how best we can handle this and ensuring your last paychecks go to Sarah here, that sort of thing.” Ryan’s emotions went quickly from rage to panic. This was all far, far, too much. This was Sarah’s revenge? To force him to be some kind of mincing sissy?? To make everyone think this is what he wanted?? No, no NO!

To his further horror, the combined effect of all of this had him feeling like he was about to sob. His cheeks felt puffy, his eyes felt heavy, his breath was getting shallower and shallower... Sarah knew this happened, she must have been counting on it... and sob he did. Weeping, whimpering, sniffling sobs as the whole room gasped and giggled.

“Oh, she’s so overwhelmed!!” Cooed Kayla, who appeared genuinely affectionate.

“Welcome to girlhood, baby!” Sarah’s friend Maya laughed, clearly scornfully to those who knew.

“We have a million more surprises... wait until you see your room!!!” Chloe’s sweet voice made Ryan sob harder.

Sarah pulled the sobbing sissy in close for a hug, whispering in Ryan’s ear and letting her lips touch her ‘husband’s’ cheek.

“By the way, the other thing, the part where I get fucked by a real man, is still gonna happen. Probably many times. You’re stuck like this, baby.” She kissed his teary cheeks and thought of all the people who’d get to see what her husband truly wanted to become, deep down, all this time... maybe she’d start with Marissa and her boyfriend... 3

"Wave goodbye to Daddy! That’s my good girl! Say have a good day at work, Daddy! OH, how I love this part of the day! Don’t you, Lucy darling?”

“Yethh Mithh Thhawwah... I wuv waving bye-bye to Da-da!”

“I bet you doooo! A big strong man like that needs his girls to encourage and support him every day! You remember how hard a big finance job like Daddy’s used to be on you! But it’s just us girls now, just how you like it, right baby?”

Two years had passed since Ryan’s betrayal and Sarah’s plot to trap her cheating, misogynistic husband into life as a prissy, regressed, sissy had worked beautifully. In mere minutes, a formerly dominant and assertive man was viewed by all the women in his life as a simpering, whimpering, sissy in a silly little dress. It was an image none would ever forget, and a role Ryan had been incapable of talking himself out of. She skillfully deployed his overbearing Mother, the only woman Ryan was truly afraid of disappointing, as the padlock on the door back into his manhood. She was so convinced from the minute Sarah had told her that her oldest son was a secret sissy, and worse still for Ryan, she’d been so thrilled that the son she’d grown weary of watching act so coarsely was only doing it to over compensate for the softness she knew was there. It was a powerful emotional cocktail that had majorly helped keep Ryan in place as she locked him in as her sissy.

What really surprised Sarah was how nearly everyone in Ryan’s life accepted this truth. His sisters eagerly embraced their new roles as his older sisters, and dedicated themselves to wrapping poor Lucy in a feminine embrace, taking him shopping, going on girly errands together, taking him to the nail salon and even for tea like they had when they were young.

His male friends largely vanished, but his few female friends (mainly ex-girlfriends) all reached out to express their support. A few even reached out to Sarah to tell her how brave she was, and publicly supported and praised her for taking it all so well.

Then there was Marissa, the secretary he’d cheated on Sarah with. Initially, she had some ideas for what she could do to get her back, beginning with a sit down girl-to-girl to poke at her worst insecurities. It was there where Marissa tearfully apologized to Sarah, explaining she was worried she’d lose her job. Sarah forgave the sweet girl immediately, and hired her as a babysitter, for a very good rate, for all the dates she’d be going on in the near future. Marissa gleefully accepted, after insisting that the chastity cage “Lucy” was locked up in never be removed. Both women loved the perverse reality that Lucy’s last male orgasm had been inside his babysitter. The same babysitter who insisted on a 7 PM bedtime, G-rated princess movies only, lots of playing dress up and dolls, and no solid foods while she was in charge.

“Welcome back to Alpha Dogs. We’ve got a special show for you today. I want you to take a look at the two pathetic blondes I have with me today. Seriously look at these two. They’re sissies. That means they were beta men, and thanks to my program, they’ve become their true selves. As beta men, they had no value. None. Worthless. No ability to compete with men. No ability to attract women. And we have to be honest. Some men like this are unable to be saved. I can’t do it. I can’t help them be men. I’ve helped thousands of men be their optimized selves, but I can’t help betas like this, nobody can. They can’t even help themselves. So we needed to figure something else out, right? And you’re looking at the solution for so many former men like this. Sissies, introduce yourselves like we discussed. You have to explain things to sissies like this in advance.”

“I’m Jessi! I used to be Jason Kannock.” “And I’m Kylie! I used to be Kyle Morton.”

“Good job sissies. Sissies like these need to name and shame their former selves. When a man fails so spectacularly, like these two, they become something totally new. But here’s what’s special about them. They’re not like most modern women or modern beta males. They celebrate masculinity. They revere and worship real men. These two worship me. They support real men completely. Isn’t that right?”

“Yes Daddy!” “Yes Daddy!”

“Why don’t you explain a little more how you got here? Jessi, you first.”

“Yes Daddy!! I tuned in to Daddy’s channel after my ex-girlfriend dumped me for her self-actualized and totally alpha male boss! I was so lost and upset, I bought the premium counseling services so I could chat 1:1 with Daddy, and after I confessed to Daddy that I’d always had secret sissy fantasies I struggled with, he helped me realize there was no hope for me to EVER be a real man like him! DUHHHHH! Sooooo obvious once I heard it! The only hope was to serve real men! So, I paid Daddy for the full failed male package, and MWAH, look at me now! Ooooo, and follow me on OnlyFans!!! JessiJizz! All the money goes to Daddy, I gotta pay him back for the full package, hehehe!”

“Good job, sissy. Oh, and if her ex is watching, I’ll fly you to Miami for free to come on the show and meet the new and improved Jessi. Maybe even do some OnlyFans collabs. Now Kylie, it’s your turn.”

“Thank you Daddy!! I was totally lost, like, got fired from my job, was getting rejected by girls, and I started following Daddy too!! And then like, it wasn’t working, so I complained in the comments, and Daddy replied that I was too much of a sissy to learn from him and it got like hundreds and hundreds of likes!!! And then like, I got all turned on!!! Soooo like, I knew I just HAD to be a sissy for Daddy, so I maxed out all my credit cards to sign up!!! OOOOO and my OnlyFans is KylieCummyTits!! In my last video Daddy fucks me over the hood of his Lambo while I FaceTimed my high school bully and let him watch!!”

“Good work, sissies. Now, be good girls and stay quiet for a second while I talk to our viewers. For you beta males out there, weak sissies, total losers: there’s hope for you. You’re looking at it. We won’t help you be real men, but I’ll help you be reach the highest value you can hope to achieve. You know I’m right.”

“SOOOOOO right, Daddy!”

“Hiya Mithh Jenny!!” My new best friend, an over-eager and shockingly regressed sissy named Lulu ran up to the gorgeous brunette attendant and gave her a big hug. How the sissy could possibly feel those breasts against her own without bursting into sobs was beyond me! Every beautiful attendant here made my cage strain so awfully. Why were they all so pretty?? Was it truly just to remind us??

“Mithh Jenny, thithh ithh Thithhy Tabithha! Thee’s my new besthh fwiend! Thhay hi to Mithh Jenny, Tabithha!” Lulu is so sincere, so I feel bad about this, but... I can’t stand her! She’s so fucking annoying! Always gushing about how sweet everyone is, how pretty and sissy I am, which toys are her fave and how silly her titties are, it’s a nonstop barrage of sissy babbling! And her lisp, oh my god, I can’t take another second of it! Everything about her is fucking humiliating, watching how sloppily but eagerly she eats our horrid meals, how willingly and casually she messes her diaper, the fact that she always wants to cuddle with me even after spilling food all over her front and pushing a big load out of her rear!

I often wonder if she was like me, a year or two ago. I’m not sure when she arrived here, and she won’t really tell me. The fact that she’s here, in this facility at all, means she either had money or her family does. Most sissies here grew up very privileged, how else do you typically end up in a facility geared towards failed men that costs upwards of tens of thousands a year?

Did she also think she’d want this? That this kind of life would make her happy? Free her from the stress of manhood? I wish I could ask her and get any kind of real answer, but I know I can’t. Especially not without one of the attendants overhearing me and spanking us both. I did that only once, and the look of shame and betrayal from Lulu as she dutifully laid over Miss Ramona’s lap in a messy diaper is the closest I’ve seen to a flash of a sissified man under the ridiculous Lulu persona. It somehow made me feel worse to know there might be someone who is more like me under all of that...

Maybe she’d even been someone who deserved this. Some kind of pervert, or worse, someone who’d taken advantage of a girl or sold drugs or done any of the awful things rich boys do. There were plenty like that here, and I’d never know...

“Sissy Tabitha?? Hellooooo? Earth to sissy??” Miss Jenny waved her hand in front of my face and giggled. “I saaaaaid, you’re here with me for several hours, and you’ll each receive a didi change at the end! Now, what do you say?”

1

Meet Sissified Air‘s first, and so far only, pair of sisters! These two embody the ultimate ethos of Sissified Air, and are currently taking pictures that will be used on dozens of promotional materials. Due to the strict contracts all the sissies operate under, they won’t see a dime of it, but shouldn’t fame be enough of a prize for a sissy? And these two were no stranger to the spotlight.

Meet Brandi and Bambi Sky! Brandi here is one of our star Sissy Attendants: once upon a time, “he” was a hero! Brandon Early was the pilot who successfully landed a plane full of passengers even after the landing gear malfunctioned. You may remember him from his CNN appearance, or his late night TV appearance, or his magazine cover titled ‘Hot, and Heroic!’

Well, like so many of our Sissy Attendants, poor Brandi was caught in a lie! You see, the malfunction wasn’t a malfunction at all, and Brandi just made a big mistake! After the golden boy’s tumble down, she was offered the first ever Sissified Air TWENTY-FIVE YEAR deal, a deal that included a total settlement with her former airline. She instantly became the most famous and requested sissy in our fleet.

Now we come to Bambi! Bryce was Brandon’s younger brother, a high school senior at the time of his rise and fall. Bambi saw what a transformation her older ‘brother’ went through, and begged to join her! We couldn’t resist re-uniting the two, and gave Bambi the same twenty-five year deal. Now YOU can hire them both: these two are a package deal!

Brandi had to hold back her sobs as she read the promotional copy. She’d heard it all a million times, but something about seeing the picture of the two of them next to these lies made it all the worse.

Brandon had been a hero. The gear had malfunctioned. But, one call from the manufacturer, and his hero arc became a total nightmare. They refused to admit fault, and his airline was all too happy to sell him out. He was under so much pressure, clearly being scapegoated, when his new employer gave him a call. Brandon, 26 at the time, had been raising his younger brother as their father was a boorish drunk who couldn’t hold a job. He couldn’t possibly go to jail... so he took the deal.

He should have anticipated that becoming the country’s most famous ruined sissy of the week would be hell for poor Bryce. He went from popular kid to bullies’ target number one, with every guy in the school suddenly treating him like he was a sissy-to-be. Brandi didn’t blame her sister for what happened, she understood it. She even felt it herself, in some ways. Bryce folded. He started sneaking Brandi’s makeup, wearing her clothes, inviting boys from school over to the new smaller apartment they’d moved into. His girlfriend found out and dumped him, which only fanned the flames of the rumors. One day, Brandi came home early to find Bryce wearing one of her uniforms being double teamed by two of her former friends. She pretended her tears when Bryce admitted she wanted to join her at Sissified Air.

Now, Brandi was stuck as the supportive older sister to an eager sissy. Bambi had turned their lives into a neverending cycle of femininity and humiliation. A small pink apartment near the airport, a tiny pink VW Bug they drove to and from work, photo ops and promo tours for the company that had ruined her life.

Sadly, her trials and humiliations hadn’t ended yet. The day the article came out with the two of them on the cover, Bambi burst into her room crying what she would discover were tears of joy. “BRANDI! Guess what?? Daddy called!! He wants to be back in our lives!! Isn’t that so lovely??” Brandi’s jaw dropped, just before Bambi said the words that would ruin Brandi the most: “Honestly... I really need a male role model back in my life!”

2

“DADDY!” Bambi had greeted their father with an eager hug, kicking her back leg up as she kissed him on the cheek. “It’s been soooooo long!”

“And so many changes!” Their father, Bruce Early, looked better than Brandi remembered. He was more put together, his beer belly was mostly gone and his arms looked much bigger, and he’d even driven a Mercedes to dinner! He turned to Brandi, and she felt like he could see right through her. “And how’s my oldest daughter?” Bambi cooed, and said “AWWWWW!” so loudly that people’s heads turned. One of the things Brandi hated most about her new life was that when a head turned in her direction, it didn’t turn away. Bruce led the two sissies to their table, the restaurant was nicer than any they’d been in for quite some time.

“SO!” Bruce declared as he sat down, having pulled the chairs out for them both. “I obviously need to say something to you both. Bambi: you’re the happiest girl, sissy, whatever you want to be called I’ve ever met. I’m so glad you love life so much, I always knew you’d end up just fine.” Bambi started crying and giggling at the same time.

“And Brandi...” Brandi had been dreading this night for weeks, and she really felt like she might sink right through the floor. “I’m so sorry I forced you to grow up so fast and raise Bambi here. Clearly the pressure just built up inside you until it was all far too much, and then... I’m sorry I wasn’t there for you during your fifteen minutes of fame. I was still a bit lost, myself. But I have good news for you both: the last three years, while you two have been flying across the globe, I’ve become quite successful.”

Brandi sat, stunned, as her father drove nail after nail into the coffin of the self image she’d always had as a man, as more put together than him, more responsible... as she sat at the table in a skirt with heaving breasts as her formerly deadbeat father bragged about his wealth. As the waitress came out, giggling at the three of them, he ordered wine and insisted on paying for everything as he continued to regale them.

“My point is, if I wanted to, I’d never have to work again. But who wants that! So instead, I’ve decided as part of reconnecting with the two of you, I’ve purchased a 15% stake in Sissified Air! They’ve even given me a board seat, which actually makes me...”

“Our boss!” Brandi gasped. Bambi, who hadn’t yet understood, squealed with glee. Bruce came around the table to put his arms around them both.

“That’s right. I also can’t have the two of you living in that horrible little place by the airport, anymore. I insist you move into my house, I’ve purchased quite a large place not too far from you. It’s begging for two girls like you to spruce it up.” Brandi had no choice, Bambi was too excited for her to say no.

Tipsy from the wine, Bambi excused herself a little later to visit the restroom. Brandi sat nervously, as her father smirked at her.

“Boy. That little sister of yours sure is a ditz, isn’t she?” Brandi giggled a little, despite herself. “Except, she’s not as silly as my oldest, who thought she could do better than me only to end up like this. If you hadn’t let your pride get the better of you, I’d have made you my company’s Vice President. Instead, you and your sister bring champagne to men like me every day. That must just be killing you.”

It was. What’s worse, is Brandi was quickly realizing the only men she’d associated with for years were her total superiors, who she communicated with through submission and flirting. Now, her father who she’d hated for years was mocking her to her face, and she... she was enjoying it.

3

When Brandon was 18, he’d moved away, went to college, and said goodbye to his deadbeat loser of a father for good. When Bryce came to him, when Brandon was 22 and moved back to their city, and asked if he could move in with him while he went to high school, Brandon felt proud, and... superior. Of course he was above his loser of a Dad. He didn’t even know what he was doing now. He’d bounced around, from sales job to sales job, he could be stocking shelves by now. Brandon was a pilot, successful, nice car, dated hot girls... clearly, the family’s alpha. Or so he’d thought.

“Oh, DADDY! It’s HUGE! And so FANCY! AHHHHH! Brandi, let’s go pick our rooms!!” Bambi giggled as the two sissy sisters arrived at their Father’s house. Brandi had to admit, it was much nicer than the very girlishly decorated one bedroom they’d been sharing in a neighborhood that really wasn’t very nice. Of course, the sissies were experts at diffusing male attention, skills that were as useful on their flights as they were while getting the mail being catcalled from ten different directions. Brandi had been so... humiliated, seeing her Father’s reaction to their lifestyle in person when they moved their things out of the little rental.

“Now hang on a second!” He laughed. “Before you two go running around re-decorating those rooms, I wouldn’t be a good Father if I didn’t set some ground rules, would I??”

“Omigosh! No Daddy! Of course!” Bambi giggled and minced over to the kitchen table to sit down and listen. Brandi followed, embarrassed. You didn’t set ground rules before! She thought ruefully.

“Rule one: I know we’ve all had a lot of different names for one another over the last few years. And Brandi.” he looked at her, surprisingly sternly. “I don’t like ‘Bruce’ any more than you’d like ‘Brandon!’ So, I’ll call you two Brandi and Bambi, and you’ll call me Daddy.” Bambi squealed and nodded. Brandi’s heart sunk. Daddy???

“Rule two: Sunday dinner! Being a board member’s daughters has some perks, and one is that I’ll make sure we do a weekly family dinner!” Bambi ‘AWWWWWW!’d’ again.

“Rule three: keeping up our image! This home is now a public branding exercise for your little airline. That means any rules at work in terms of hair, makeup, attitude, those apply here too girls. We’re going to have lots of guests as the company grows! Including some of your other bosses!” Brandi hadn’t felt this kind of chest pounding, how is this happening to me feeling since the first days of her new job. “Y-you want us dressed up, hair in pigtails, calling you Daddy?” She regretted the backtalk as soon as she said it, but her Father simply smiled.

“Yes, good job keeping up! Rule four! Now Bambi, you’re too young to really remember this, but your older sister used to sneak all kinds of,” he whispered, “girls!” Bambi giggled. “Right into my house! No, if either onf of you brings a man home, he’ll be meeting me at the door and shaking my hand. None of this casual shit guys your age want to get away with. Understood?”

“You don’t have to worry Daddy, Brandi’s never had a girl over since she became Brandi! Boys, though, hehehe!” BAMBI!! SHUT UP!! Brandi wanted to scream. Instead she blushed beet, beet red.

“Rule five: because you don’t pay rent, you have to help out. There will be chores, and they will be performed. I don’t believe in wasting money, there’s no cleaning service here, so you girls will pitch in.”

“Rule six, and don’t worry Bambi, I’ll have these written down for you: Rule Six is I’m the head of the household. There’s no situation, Brandi, Bambi.” he said both their names but only looked at Brandi. “No situation where either of you are in charge. Not one. After so much chaos, it’s time for some control. I need both of you girls to tell me you understand.”

“Yes, Daddy!” They said in unison, to his sincere delight. Brandi’s head spun as her... Daddy posed them both for a picture: the first night in their new home, as a family again.

4

Daddy smirked as he swiped his Amex at the fourth store of the day. “They say sons cost you early, but daughters cost you later!” He laughed to the sweet woman behind the counter, who giggled and exlcaimed “It’s SOOOO true!” If only she knew how true it was, Brandi thought as her Daddy smirked at her. Also, she really wasn’t a fan of how many gorgeous women flirted with her Daddy these days... women Brandi would have been attracted to, had she not...

“You know how I know you were meant to be a blonde bimbo?” He joked to Brandi. He’d somehow become even more comfortable directly pushing her buttons. “Because I just spent $1,800 in the women’s section of Nordstrom?”

He laughed. “Well, yes. But I was going to say because you’re 100% comfortable swiping your Daddy’s credit card, but in all this time, you’ve never even asked me what I did to become so successful. I used to imagine you begging me to work for me. Little did I know what fate had for both of us.”

“Y-Yes, Daddy.” Brandi had spent a lot of time lately thinking about something one of her girlfriends had said once about going home for the holidays, where she always felt like she regressed to her angsty teenage self. Brandi was feeling a lot of that angsty vibe lately, except, she was also trapped in the body and life of an airheaded rich girl.

“You know something else I was thinking?”

Steeling herself for more humiliation, Brandi sighed a little. “Yes, Daddy?”

“Do you remember Madeline Herbert? I’m sure you do.”

Brandi felt her chest pang and her cage strain. Of course she remembered Madeline. She was the most beautiful, energetic, sweet beautiful blonde in her high school, and ‘Brandon’ had been totally in love with her. Madeline had always insisted on how sweet and cute he was but just wasn’t a romantic fit... which Brandon had always taken to mean ‘not rich enough.’

“You remind me a lot of her, now. I bet you’re a real heartbreaker on your flights. I’ve heard some stories!” He laughed. “What do you think Madeline would say about you now?”

“Da-addy!!!” Brandi’s voice cracked and she flushed beet red as her Daddy gripped her arm and led her into another store. She caught a glimpse of herself in the mirror, and to her horror, thought oh my god... I look JUST like Madeline Herbert... “You know, she’s married, I think... to one of my old friends...”

Daddy smirked, his goal of riling up poor Brandi clearly successful. “Well, I guess we’ll just have to make sure we send them a copy of the new Sissified Air magazine cover, so they can see everything that you’ve been up to!” Bambi giggled and laughed, winking at her older sissy sister, as Brandi mewled and distracted herself by flipping through some skirts.

5

Standing for picture after picture, with her long blonde hair in pigtails, her Father’s hand just above her derriere, her tits pushed up in a bra, with her younger brother-turned-sister looking like a carbon copy of herself and a constant reminder of how absurd she looked... Brandi felt a moment where she was pretty sure her male ego permanently died. Nobody saw her as anything more than a blonde bimbo, destined to only serve as a model for more and more failed men like she’d once been to become submissive cocksuckers like she was now. For years she had so much regret about how this all happened, now she was trying to stifle that internal resistance as much as possible. It was easier than failing to fight back.

This wasn’t her first promotional shoot for the airline with Brandi and Bambi shown off as the model girls for Sissified Air. It was, however, the first one where their Father was present, as he interviewed for a front page spread in some magazine. Something about business. Brandi found it easier not knowing the humiliating details.

The interviewer, a gorgeous but professional blonde woman, was peppering her Father with questions. “You know, some people think these sissies are really very exploited. What would you say to that?”

“Would I let my sissy daughters work a job where they’re exploited?? Think of it differently. Is there another job that offers such comfortable, rewarding, and stable work for people in times of crisis? I’m the first to admit, I lasped in my duties as a Father, and my poor oldest here suffered quite the breakdown... but being a sissy saved her! Just like it can save so many wayward young men out there.”

“And as a Father... you’re not... upset that...”

“Of course not. And between you, me, and your readers...” He leaned in for a dramatic whisper. “It’s no great loss!” This finally got a giggle from the reporter.

“Hehehe! Well, I was going to include this as a disclaimer in the piece, but I actually have first-hand knowledge of that fact!” The reporter turned to Brandi, and the poor sissy suddenly recognized her. “Brandi and I dated briefly, back when she was still Brandon! No great loss.” She winked at Brandi. He’d gone on a few dates with her and hadn’t called back... pretty standard for him back then. If only he’d known how precious the experience of being able to fuck a girl would be for him.

“So you’re still single, then?” Brandi’s Father said with a laugh, and the pretty blonde played with her hair and nodded. “Well then you wouldn’t mind if I took you to dinner after this, then?”

“Should one of us go help her??” Diamond asked, half-kidding, half-serious. The curvy, dark-skinned sissy had just returned from servicing one of her regulars to see the new sissy, one each girl knew quite well, totally freaking out in front of the mirror.

Destiny, a mean blonde, scoffed. “It’s not like she was ever nice to any of us when she had the chance to be! He knew the reality of every one of our situations, and still showed up every night so we could suck his little cock...” She shuddered, genuinely upset she’d let the big-titted sissy in front of her cum down her throat. “I’ll be nice after she’s sucked as many cocks as I have. And that could take years.”

“SO?? Like, every guy here does that, and we like some of them! Plus, he always tipped me pretty well... honestly girls, I just think we all feel a little... awkward! Like, I know I do... because I know how it makes me feel to see her go from man to sissy, and what that means about how everyone saw each of us when we were transformed... but that doesn’t mean we shouldn’t be helpful! She’s one of us now! And if I was having a night as bad as she is and you girls didn’t help me, I’d be totally upset!!” Rosalia looked at the other sissies a little judgmentally and walked up behind the newest sissy, putting her hands on her shoulders warmly. “What’s wrong, baby? Aside from... the obvious...”

The new girl, Alexa, felt her breath caught in her throat. She’d been a regular here, of course. She’d also been married. Imagine poor Alexander’s surprise when of all men, his father in law stepped out of a private room just moments after he did. Behind his father in law was Diamond, wiping cum off her lips. Both men stood in shock. But he was safe, right? His father in law couldn’t do anything! It was mutually assured destruction, they’d both be ruined, right? Right? Wrong.

“Aside from this??? How could it be aside from this?? Look at me!!!” Each sissy nodded knowingly. They all remembered how it felt to not only exist in their new, transformed bodies, but to be so completely feminized that they were even attracted to their new selves, all while learning to live in permanent chastity, their sex forever constrained by their new Master.

“But that’s not all... Daddy Derek... he just told me who my first client will be...”

The girls all nodded knowingly. This was Daddy Derek’s favorite move: the lecherous creep loved to make the first man each sissy serviced one that would cement their place forever as a ruined sissy. A link to their past life to show them their new status. For Rosalia, it had been the manager who’d fired her from the last job she held as a man. Diamond’s had been her old football coach, the man who told her she was too fat to play, now lusting for her curves. Destiny’s had been Derek himself: she’d bullied him all through school. Hardly a coincidence, she was his prized find. Now, Alexa was about to join the sisterhood of humiliation.

“It’s my...” The girls nodded, they all knew. “It’s my ex-D-Daddy in law... Daddy Derek is making me call him that, I just... I c-can’t take it, I don’t know how I’ll manage... my lips, his cock, his cum, my t-t-tits!!”

“Honestly, I just love the style!! It fits everything for me, it’s prissy, it’s oh so feminine, and it forces my loser of a husband to keep her head held straight lest that perfect wig fall off! I just kept thinking: what would he want men to see him wearing LEAST, and I worked backwards from there!”

“Well it’s perfect! And Brian, baaaaaby, you wear it soooo well, you’re like a total natural! If I ever need someone to play Marie Antionette, you’ll be my first call for sure!” The girls both giggled.

“No more Brian! My sissy husband has a new name: Babette!”

“BABETTE! AHHHHHH!!!” Olivia squealed with delight. “That’s AMAZING. So diminutive! I just wish we could go back in time and tell cocky, silly, embarrassingly desperate Brian that one day he’ll become his best self as Babette. You couldn’t have picked more perfectly babe.”

Julie and Olivia burst into laughter. Julie and Brian were married, and Julie’s best friend her whole life, Olivia, had been Julie’s Maid of Honor... which made Brian’s drunken decision to try and hit on her just a few months after the wedding all the more baffling. He thought she’d always had a little thing for him, and she was really hot, so why not give it a try? Well, the girls decided, we’ll show you why not. Threatened with divorce and total ruin, Brian was sent to a very special “instructor” the girls had found online who specialized in... this type of thing. Among many potential punishments, forcing Brian to be sissified was all Olivia’s idea! Julie had needed some convincing... and that’s where the chastity was so helpful. That, and...

“I’m so glad you’ve accepted the fact that real men need to be involved in Babette’s punishment,” Olivia giggled. “Your dear wife was all nervous, Babette! Hehehe, remember dear? Can I really just start fucking real men? Where will I even find them?”Olivia said in a mocking tone. Julie was cackling with laughter.

“I know, oh my gosh, I was just so overwhelmed. I didn’t realize that just the fact that Brian was out of the house would be enough to have some start sliding into my DMs! I can’t even IMAGINE what’s going to happen when I post Babette here. I think I’ll need an assistant just to handle my schedule! In fact, now that you’re out of a job, Babette, I think you’ll do just that! I’ll work from home, and we can set up a tiny desk next to mine for your new job finding me real men. Finding both of us real men, actually!”

Julie squealed. “I love it! She can do phone interviews with them and everything! So, just because I want to hear you say it to me, how long do you think this punishment should last, Babette?”

“You want to be a little mincing sissy??” Kelly, Chris’ wife of 18 years, was pacing around the room, screaming angrily. “You think you just get to humiliate me like this?? Be a little caricature of a slutty girl instead of being a fucking man for me?? You were never enough of a man for me! Of course you were a secret sissy! Were you a sissy the whole time??”

Chris had done nearly everything according to expectations. He’d married his high school girlfriend. He’d turned her into the perfect housewife, letting her revel in femininity and run around town as a perfect wife, volunteering and socializing while he ran a very successful insurance company.

Meanwhile, of course, Chris was secretly a sissy, posting online about his fantasies of being a desperate cock whore for powerful men and dominant women... fantasies his wife discovered and was horrified by. Then, she came up with a plan. You want to be a sissy? You want to be feminine? Just you wait, she said...

Today was the day, just as Kelly had planned immediately after the secret was out. Easter Sunday, the day when the entire town was packed into Church and scattered afterwards for brunch and garden parties, would be the day Christie was introduced to everyone.

Having been the talk of the town for weeks, thanks to Kelly describing the situation in detail to every one of her girlfriends, Christie felt ready to faint walking through the doors. Everyone looked, but few spoke to him, outside of a few of Kelly’s girlfriends teasingly welcoming him. Their husbands simply stared, embarrassed that one of their friends had so completely been transformed into something so...

“This is going so perfectly.” Kelly leaned into her husband’s ear as they sat down. “You thought you’d be some fun-loving slut... you’re going to be exactly what you forced me to be. You’ll clean the house. You’ll take care of the girls. You’ll spend hours on hair and makeup to impress me. Of course, I’ll notice more than you ever did. And just like you cheated on me with men online, I’ll cheat on you, as much as I want... look around. Men want me. You’re the only fucking loser who didn’t, and now, everything about you screams what you really are... my gosh, we should have done this years ago...”

“Hey Tristan??” Sarah called from the top of the stairs. “Will you come up here?? I’m in our bedroom!”

Tristan paused the dishes he was doing and obediently scurried up the stairs. Tristan?? Our bedroom?? She hadn’t called it that in... who knows how long! Tristan hadn’t slept in there in over a year. Mr. Matt had forbidden it even before he moved in! And Tristan was even stranger, Sarah hadn’t called him anything but Tiffany, or Sissy, or maid... well, she called him a lot of things, but she probably hadn’t used his boy name even before he moved out of the bedroom! Was this... he couldn’t get his hopes up, could he??

Tristan opened the door to the bedroom, and to his shock, Sarah was laid out on the bed! In pink underwear!! It was too much for his poor caged clit to bear!! Could this really be happening?? It had been... over a year!!

“Oh baby... Matt’s not here... I’ve really... I really miss us having alone time. Come here baby.”

“M-Miss Sarah!! Do you really mean it??” Tristan’s poor caged clit was on fire!

“No Miss, baby... come here... come fuck me, baby... I miss it so bad...”

Tristan didn’t know how to ask, will you unlock me then?? He jumped on the bed eagerly, his beautiful wife’s tits on display, a look of genuine lust and attraction he hadn’t seen towards him in years... she looked so perfect and beautiful, her tits had grown since Matt moved in and encouraged her to be her voluptuous, gorgeous self... not like when Tristan had tried to put her on a diet... he’d been so stupid...

“I wanna fuck you so bad...” He whimpered in her ear while they kissed. “I miss it so much...”

“How much do you miss it, baby?” Sarah’s voice was like honey. “Tell me how you miss my sweet pussy around your cock and you can fuck me...”

“I need it soooo bad!!!” Tristan’s voice was whimpery and whiny, he was having a hard time keeping the sissy inflection out of it!

“Bad enough that you’ll risk upsetting Matt...?”

“Y-Yes!! I’d take a spanking just to fuck you!! Anything!!”

Sarah started giggling and Tristan’s heart sank. “Anything? A spanking?” She giggled.

“Y-Yes... are you... will you unlock...” Just then, the closet door flung open.

“Unlock your cage?” Matt was standing there with his phone out, recording the two of them. Sarah flung herself out of bed, laughing in hysterics. “APRIL FOOLS! You thought you were gonna FUCK me??? Oh my GOD! I even defended you!! Matt said you’d go for it, I said you would know it was a trick! WOW!”

“I knew she’d be too weak to resist you, baby.” Matt gave Sarah a wet kiss and he slapped her ass. “You’ll get about a hundred of those later, and they won’t be as soft as I’m about to be on Sarah’s... but first, I need to give her what you can’t. Go finish the dishes, sissy.”

“Hehehe! I must say, you’re off to an absolutely lovely start this morning!” Maria giggled as she walked into the playroom. “Is Mama’s sweet girl going to spend her Sunday behaving as a perfect princess for Mama? No silly behavior this time?”

I nodded meekly. I still couldn’t believe how stupid I was not assuming that my wife had set up cameras in each room of the house. Last Sunday, I’d tried to catch at least a little college basketball... it was becoming difficult to explain what I spent my Sundays doing to the guys at work, so at least I’d have seen the game, even if it was while wearing my Cinderella gown... only for my stomach to drop when I received a group text from Maria and her boyfriend: “Back in your playroom, NOW, or 50 spanks will turn to 100.” When they returned to discover I’d tried to have some leftovers instead of my Gerber’s mushed carrots with cupcakes for lunch, it did turn into 100 spanks, 50 from Maria and 50 from her boyfriend Gary. Gary was older, bald, muscular and mean. I often wondered, was that really my wife’s type now?? Not that her previous type of guys like me worked out so well...

“If Gary and I learn that you touched the TV, your computer, or your chastity cage, last week’s spanking will seem like a pleasant correction compared to what Gary will do to that butt of yours this week. Do you want to spend another Monday in the office smarting from what a real man does to a sissy like you?”

No, of course I don’t! It was bad enough spending my Monday morning scrubbing off all the glitter from this ridiculous dress... “No, Mommy! I p-pwomithh! I’ll just dwink my tea!!” I had to use my most lisping and pathetic voice. Gary’s idea. Another idea from Gary was for my tea to not even be tea, just warm water Gary had spat quite a lot in.

“Good girl!!! That’s my sissy. What will you be doing?”

“I’ll be pwaying dollies, I’ll be dwinking tea, and going on my v-v-virt-u-waa pwaydate with my new bestie...” Maria had gone online and found another ‘Mommy’ like her who had similarly sissified her husband. I think he’d been much more willing and into the idea than I’d been, and fittingly, his life was so much more sissified than mine was. It really stressed me out every time we spoke, he’d quit his job over a year ago and his entire family and all his friends knew he was a sissy. He even went out in public like this! We mostly talked about silly girly things he was teaching me...

“OOOOOO, your BESTIE!! You mean Sissy Petunia?? I just adore her!! I hope your girl time is perfectly lovely, I wanna hear allllll about it!” I knew she probably would listen to the recording, as well... “I really hope that sweet sissy is a good influence on you! Ooooo, do me a favor, will you?”

“W-What is it Mommy?” This couldn’t be good.

“When you’re on your little zoomie, which I assume her Mama will set up for her, will you ask Sissy Petunia’s Mama to send me that little thing she was telling me about? If she needs a reminder, tell her it’s about diapers!”

“DIAPERS?? Mommy!!!” My jaw dropped. I knew Petunia wore them, but surely she couldn’t mean-

Simon came to south Florida with dreams of success. He’d just graduated from business school, secured a high-paying job at a large firm, his sign-on bonus was so large he’d even bought himself a BMW! The sales assistant had joked that he’d have no problem impressing his dates with this, and he’d agreed wholeheartedly. He had it all. His Mother had made him promise to visit his ‘Aunt Tamara,’ not really his Aunt, but an old friend of Simon’s mother from college who had been around a lot when Simon was younger. She was big, loud, and in Simon’s view, incredibly cringy. She didn’t even have a job, he didn’t think she ever had, she’d spent her whole life unmarried living off various men. What the fuck could they possibly even have to talk about, he thought. Of course he said yes, though. Of course he’d go to dinner with Aunt Tammy, or whatever.

Except, of course he didn’t. He ignored her, spending his time partying and taking girls out. Was he successful... well, not really. Did he max out a few credit cards? Oh yeah. Did he impress his bosses? Well, also no... first came a performance review, then came termination. In debt, with no real references, Simon freaked out. So when he couldn’t make rent, he called the only person he really could. He begged Aunt Tammy, please don’t tell his Mother, not until he figured his situation out...

“You wanted nothing to do with me until you were desperate. So yes, I’ll help you, you can stay here as long as you’d like for free. The lodging isn’t the concern. The lie is what costs you.” Simon’s shame was too much to bear. “P-Please. I’ll do anything. Just don’t tell her... what will it cost??” Aunt Tammy cackled.

“Well, it’s very funny you ask... a few things... some big, some small. One that I bet is very small...” To Simon’s shock and disgust, she pointed to his crotch and made a little indication with her fingers.

“I remember what a little pervert you were, so when in my house, you’re going to be locked up in chastity. Ever heard of chastity?” Simon nodded in shock. “Good! Additionally, I’ll be taking your car. I like it. Lastly, and this should be a given considering your... cage situation, but no girls allowed! In fact, you need permission for each guest, to be approved by me. Men only.”

“I don’t like men!” Simon heard how pathetic he sounded, and so did Tammy. “HA! Well, that’s too bad my darling, because men are how your Aunt Tammy has all this... so, with that in mind... you’re going to be pulling your weight around here. That means you’ll help me to entertain them.”

Simon was as shocked and horrified as he was stuck.

“Now, here’s the good news: I have a certain gentleman who I know has a special thing for young men in your situation. Well, the situation you’re about to find yourself, that is!”

“Aunt Tammy, I d-don’t understand... what situation is that??”

“Young men, down on their luck, who have been forcibly feminized, of course! I have to admit, I actually have thought about this before for you, I was ever so upset when you declined my social invitations, and look how life works out! You simply dropped into my lap! How perfect is that? Now, we have quite a bit of work to do... unless you’d like me to tell your Mother, that is...” 2

In a span of mere weeks, Simon’s life had gone from working in a high-rise, putting his card down at clubs, trying to pick up girls... to financial ruin, total collapse, panicked nights... to this. Living in a palace of pink. A cage around his admittedly small cock, a cage his Aunt Tammy held the key to. His humiliations were almost too much to bear, as Aunt Tammy ran him around to appointment after appointment in his car he’d been forced to hand over. Blonde extensions were added to his hair, his clothing was locked away in some storage unit and replaced with trips to Lilly Pulitzer, Francesca’s, Charlotte Russe... places Simon had heard of but never considered stepping foot in.

As horrified as Simon was, Aunt Tammy was equally thrilled. Watching her best friend’s dorky-turned-douchey son forced to spend his evenings learning to blend foundation and speak in a lilting voice made every day a hilarious adventure. The young man cringed soul-deep every time she introduced him as her niece, but they hadn’t quite settled on a name yet.

“We need something as fab as Simon was borrrring. I even told your Mama how I hated that name. Good thing I get to change it now!” Aunt Tammy cackled over a glass of rosé. “SABRINA! Like that little pop-star, I just love her, so do you, Sabrina is perffff. Agreed? Agreed!”

Simon went from desperate to apoplectic as the reality of life as Sabrina set in. Frantically, every night, he fired away job applications to any position that would pay enough to get him out of there. Weeks passed with no response to any application, until one night, he recieved a reply to an application for a junior associate position to a wealthy local man’s family office, Frank Dimopolous. Simon scheduled a phone interview while he knew Aunt Tammy would be away one afternoon, and to his slight surprise and total relief, nailed it! The pay wasn’t great, but still, close enough, he thought. When he got another follow up email from Frank requesting an in-person interview, he was elated, for about half a second. HOW would he go to an office like this?? He didn’t even have his clothes, and these extensions were sewn in! He stared a the email with a mix of elation and despair.

Just then, Aunt Tammy burst into his room and he shoved his laptop away. “Wishing you could masturbate like a stupid teenager?” Yes, Simon thought ruefully.

“Oh heavens no, Aunt Tammy!” Simon said in his most practiced lilting Sabrina voice. “What’s happening, Auntie?”

“Good news. You’re finally ready for your first gentleman caller. And from what I hear, he’s quite the wealthy man. He’s a friend of one of my closest friends, and he’s the one who mentioned wanting a girl just like you. So do what your Auntie’s taught you, and there won’t be a problem, understood?”

Sabrina’s knees were wobbly as he got ready to greet the men in his bathroom. His blonde hair up in pigtails, his soft arms exposed by the dress, his bra stuffed to give the illusion of breasts with his dress. He looked like an older, perverted man’s wet dream. It was objectively the most attractive he’d ever looked, as a man or as a girl. He was gripping his skirts in terror as he heard the door open.

“Hiya boys!” He gasped as he heard the door open, with Aunt Tammy greeting each man. “My silly niece is still primping, but come on in!” Sabrina could barely think over the anxiety screaming in her head as she opened the door, to see...

“Hi there, Sabrina!” The voice was unmistakable. “I’m Frank.” A tanned and dark-haired man greeted her with a handshake that he used to pull her in for a kiss. “This is going to be a fun final interview!” Sabrina gasped, as she saw Aunt Tammy in absolute hysterics behind Frank.

“Did you plan this???” Sabrina gasped as she shook her head. “Can you believe it?? NO! Fate strikes again!” 3

For Sabrina, it was the date, or fake interview, that never ended. Aunt Tammy had created Frank’s dream girl in every way: blonde, flustered and ditzy, a taste for the finer things but a glitzy and girly vibe, even quite a bit of intelligence under all that prissy exterior and false bravado. Unwilling, yet perfectly feminine and incapable of true resistance. And that man was never, ever going to let Sabrina go.

He could feel the depth of Frank’s attraction from the first kiss. Those interviews went well because he was assessing his prey, not hiring an associate. Just as Frank wanted her, Sabrina became perfect for him as the depths of humiliation he felt made him the perfect submissive sissy girlfriend for the man, allowing himself to perch on his lap while Aunt Tammy looked on gleefully. The two blondes each heard the other through the walls that night, stumbling out the next morning with messy hair and smeared lipstick in a condo that now smelled of sex.

“We’re going to the mall later. The boys want to take us shopping. Clean yourself up, slut!” Aunt Tammy giggled and winked and Sabrina couldn’t help but giggle a little in return. This was her life now, she thought. And even though when she looked in the mirror she saw a pink and freshly fucked girly-girl instead of the successful man she’d imagined. The successful man was in her bed.

Soon, it was time to actually call her Mother and tell her the truth. The experience brought the two actually quite close. “Aunt Tammy, I love you.” The admission shocked Sabrina to say out loud, but it was true. Even if it was true due to the pure depths of humiliation she’d been forced into...

Her Mother was, shockingly, elated. She found it shocking, certainly, but she trusted Tammy and she trusted Sabrina. She’d never even really liked the finance bro wannabe her son had become. And honestly, Sabrina seemed happier than Simon had ever been. So, she kept up with his Mother, who would visit and queen out with her best friend and her daughter.

So it went on like that. Nights of wine and sex, days at brunch with the girls, trips to the mall, the beach, whatever events the men wanted to go to. Aunt Tammy had her usual rotation, Sabrina only had Frank. He was quite insistent on that point. Every once in a while though, when Frank was on a business trip, Sabrina would cuddle in bed with Aunt Tammy, and the two of them would trade tips on blowjobs, what men wanted, how to use both of their skills to perfectly entertain men. Tammy loved to tease that if any of Sabrina’s type-A ex-girlfriends from high school saw what a male-centric ditz she’d become they’d die of shock. Sabrina thought the real shock would come from her male classmates and friends, the ones who saw the smart, alpha male version of her former self.

Without telling Sabrina, Aunt Tammy decided to put that theory to the test with a new Instagram account of Sabrina’s new life. After following as many people as she could find, she posted this picture of Sabrina and her on the beach, taken by Frank. Tammy got permission from Frank to even tag him, he was wealthy and powerful enough not to care if his truth was out in the open, and loved how it would humiliate Sabrina!

And humiliate her it did. Turns out when it came to the question of exes vs. friends, it was basically a tie. Both groups were completely shocked and made no secret of it. I need to start manifesting more, clearly it works!!!!! posted a college girlfriend he’d cheated on. A classmate who’d always resented Simon’s intelligence texted Sabrina: Hey, do you mind if I call the school and let them know I should move up a class ranking? You MUST have been cheating! One of his most immature bro-friends, to Tammy’s elation, posted DAMNNNNN girl you look fucking hot now and so does that MILF you’re friends with!!!!

“Honey, I promise... this little period is the worst it’s ever going to be.” Dakota clasped his hands together and stared pleadingly at his wife, but it felt to them both like he was more trying to reassure himself.

McKenzie Matthews gave Dakota Matthews a sort of soft smile, and an ‘are you serious?’ look. “Honey, you’re signed up to be a sissy for six years. For some reason, I don’t think this is the worst it’s going to ever be.”

Dakota Matthews was the love of McKenzie’s life. She told everyone that, and she really meant it. They’d met freshman year of high school in a small town and almost immediately started dating. People said Dakota had sweet, golden retriever himbo vibes, but like, in an ‘is he actually an airhead?’ way. But she loved how sweet and silly he was. And it wasn’t like she didn’t have options. One of the guys who was obsessed with her all those years was Mason Horne. Mason wanted her so badly, he even offered Dakota a job at his car dealership just to have a reason to bring McKenzie around. She was the hottest girl in town, valedictorian, and now an English teacher back at the high school. She didn’t care that Dakota wasn’t conventionally successful. She just loved him. They were married at 20.

That’s why when she got the call from Dakota that he was in major trouble at work, money was stolen and he was responsible, fake cars, blah blah blah... she’d felt so guilty. Of course Mason had framed him, that fucking asshole! When her husband called, she reassured him, knowing it wasn’t his fault.

Still, Dakota had $65,000 in debt he had to find, and quickly, or Mason would press charges. McKenzie reassured him, it would all be okay. She promised. The next day, she went to work, and spent the morning incredibly nervous, until she got a text at lunch. “Problem solved. I’ll tell you tonight. I love you honey!” Her heart lifted. She knew it would be fine. And sweet Dakota had finally solved a big problem!

That’s when she learned about Sissified Air. How he’d only been able to trade $10k of debt for a year, but they’d rounded down. How it wouldn’t be so bad, and he’d be based out of the big city airport near us, and...

“Did you say SISSIFIED? What on earth does that even-- Oh my god.Wait. No!” Then McKenzie said something so cruel, she’d feel bad about it for a long time. She stared at her anticipatory mess of a husband and said, full of snark: “A man obsessed with me tried to ruin you, and you responded by figuring out how to fucking completely emasculate yourself completely as soon as possible? Seriously?”

Dakota broke into sobs. “I didn’t want THIS!!! I- I- they’re going to l-l-l-lock up my p-p-p-p...”

McKenzie had been heartbroken and upset for weeks. It hit her quickly that this was her last window for years to become pregnant from her husband, but she couldn’t bear to have sex with him knowing everything that was about to happen. When he’d inquired about that exact thought, she was even crueler. “How do you know I won’t get pregnant?” He’d gone to his initiation the next day.

She got her sympathy back after poor Dakota came back for the first home weekend. “I can’t believe they cut that messy hair of yours into bangs... are these... extensions?” He’d nodded meekly. “And the uniform?”

Dakota explained it was required attire at all times for Sissy Attendants on their first break at home. It was designed to humiliate and make them feel how feminine their bodies were becoming.

“Well, as a strategy it’s genius, because it’s going to make dinner with our Moms at your favorite restaurant... a lot more interesting.”

“So... am I forgiven for...” Dakota looked up and down. McKenzie gave him a little kiss and said with a bit of a giggle, “Honestly... I haven’t decided yet, honey.” 2

“Honey!! Oh my gosh!! Look at you!! I mean, like, you are gorgeous! What the fuck!!”

Six months of training was finally over. Six months, by the way, that didn’t count towards the contract Dakota had signed. Speaking of ‘Dakota’... McKenzie had been shocked to learn that like everything else, his name would be changing.

“Delilah?? Delilah Matthews. I’m married to Delilah. McKenzie and Delilah. Oh my god.” Delilah had blushed so hard when she’d told her, knowing this was coming. “Dakota’s practically a girl’s name- I mean, unisex- already!” The sissy ignored the barb and told her they change everyone’s names, it was just part of the program. As she learned over time, facial filler, lip injections, breast enhancements, obedience training, cosmetology, makeup, and ‘serving men’ were all part of the program.

Meanwhile, as her poor husband- poor sissy? poor wife?- was practicing heels and lipstick, the man who’d ruined him was starting to text her more and more. Her biggest mistake, one lonely night, was replying.

She loved Dak- She loved Delilah. Her sissy, Delilah. But her sissy was away, and the reply wasn’t disloyal.

“How’s the world’s worst car salesman and world’s soon to be greatest sissy flight attendant?” Mason had sent at 9:44pm one night.

“Just the loveliest person in the world, why?” McKenzie was satisfied. Except when Mason replied with “I bet she’s getting VERY lovely!” She replied again with a blushing emoji.

They hadn’t really stopped texting. In fact, McKenzie noticed herself thinking to him... fuck! No! Her... Delilah was right in front of her. She leaned in for a kiss, only for the sissy to kind of stop her.

“Well, don’t kiss me yet, you can still taste my final exam!” Delilah said with a smirk and then blushed. “Was that too much??”

“AHHH!” McKenzie giggled. “Oh my GOD!” Even though she felt awkward how much the romance had just been stepped on, she was secretly sort of happy to see a joke-y, silly version of her husband back. She nervously changed the subject. “Did all your girlfriends pass??”

“Yes!! And thank GOD, because remember how it was Maia’s second try?? And Valentina passed too!!”

“Okay, and remind me...”

“Maia’s the one with Daddy issues, and Valentina’s the one who grew up on a farm...”

“Delilah, I have to tell you something.” McKenzie blurted out. “Before dinner. I’ve been talking to Mason. Just talking. But... I thought... I should tell you.” She stood there nervously for a second.

“It’s okay, honey.” Delilah was sweet, if clearly a little sad, or... she wasn’t sure. “Everyone told me this would happen. I told my story, and all my friends said it was just a matter of time. I understand, honey.

McKenzie was shocked. She felt a little surge of... was she turned on? She’d think about it after dinner. 3

“Okay, I’m just going to say it: I forgive you. We’re even.. You have nothing to make up for, honey. I think I’ve proven that I love you no matter what.” McKenzie was staring at a very blushy Delilah in the middle of a busy terminal. “You’re totally sure you’re okay with this. I know it’s moved really fast...”

“DUHHH it’s moved fast! He’s hot, he’s a man, and he wants you sooooo badly, honey! Nothing to apologize for!”

McKenzie couldn’t help but feel guilty, and she couldn’t believe how normal this was starting to feel. Mason was the entire reason her husband was a sissified little prissy thing with big tits and a bubbly, girly-girl attitude, and he’d done it purely to make this happen, and she was letting it work?? What kind of awful wife was she??

That said... Mason was really apologetic. He did feel bad about all of it, he’d sworn to her, it was a dumb idea that had just gotten out of hand... he’d apologized directly to Delilah, and she’d just coo’d and awwww’d and folded so badly, McKenzie couldn’t believe it. “Oh my gosh! That must be so hard for you, I’m so sorry!” SORRY? SORRY? Her husband was the one in the chastity cage earning a tiny wage paying off a fake debt, and he was apologizing to his tormentor?? I mean, if that’s how Delilah was going to behave, what reason did McKenzie have to stay good?

Funnily enough, all the guys who’d been happy to hit on her when she was literally married to Dakota now had totally dried up. Mason had clearly marked his territory. It turned her on a little, but it also left her stuck at home with no options except for him. He’d even stopped this other teacher at her school, Allison, who’d been totally bullying her about Dakota. She guessed her and Mason were friends or something. She’d even apologized, and said Mason had totally explained how selfless Dakota had been when he’d... well, she’d burst into giggles after that, but it still seemed like a sincere apology.

Now, Delilah had been the one to escalate things. She’d won a prize! Of course, prizes for the sissies were designed to humiliate. One free vacation for a woman of her choosing and that woman’s man, to be served by Delilah. When Delilah told her about it, McKenzie couldn’t believe it. Her husband wanted to wait hand and foot on his wife and the man his wife was... she didn’t know what they were. They’d started having sex, though...

“You know we’ve...” Delilah giggled and nodded, as if it was the most obvious thing in the world.

McKenzie crossed her arms and gave her husband a side eye. “So, be honest with me. Does this totally turn you on?”

Delilah sputtered and nodded. “Oh my GOD...” She blushed. “You have literally NO idea.”

“Would it turn you on if I treated you like the sissy you are on this entire trip?” Delilah was giddy at this point.

“I’ve been trying to get you to do that for like, months now honey!!!”

They both giggled. I guess the trip’s on, McKenzie thought, right as she saw Mason coming up behind her husband. She gave Delilah a quick kiss, giggled, and shouted out “OH HEY, BABE!” to her new man.

Suddenly, seeing Mason walk up gave poor Delilah a surge of... it felt like post-orgasmic clarity, but she hadn’t cum in almost a year. But seeing Mason smiling and McKenzie giggling, she suddenly didn’t find it hot or funny any more. What had she done??? 4

So much time away from Delilah’s tormentor had made the concept of him pretty hot. A man with a crush on his wife who’d wanted her so badly he ruined Delilah’s? Forced her into skirts, and cages, and a lifestyle of emasculation... like, what a man! Well, ‘Dakota’ didn’t feel that way when he first got to his Sissy Training program, but then with so much sissy energy, so much reinforcement of the idea that being a cucked sissy is perfect... she grew to believe it. It didn’t help that Delilah felt like she was a walking lust-filled ticking bomb of aroused energy. So, for almost a year, Mason had been hot! McKenzie clearly thought so too...

But, McKenzie had felt too guilty to bring him over when Delilah was home, so the sissy hadn’t actually seen him (outside of some snapchats of his cock) since ‘Dakota’ had worked for Mason. Not that she hadn’t thought about him. Daily. With every emotion possible.

Then Delilah saw him, for real, saw the annoying, rude, conniving, asshole who’d totally stolen his wife and his manhood, and... and they were all friends! This was all her fault!! What the fuck was she thinking?? And when she looked at her wife, McKenzie was comfortable, and infatuated!

Internally, it was the most resistant Delilah had felt since the very first days of her training. A real man was acting like her wife’s boyfriend... I mean, he was her boyfriend, wasn’t he?? And she was stuck in this body... and she choked back a sob, stuck in this job! One of total service to them both!

Delilah thought all this while strapped into the tiny jumpseat during takeoff, while her wife had her head on the chest of the man who’d ruined her. Once they got up to altitude, Delilah did her trademark mincing strut over to the two of them as McKenzie gasped and giggled at how feminine and subservient her husband was.

“Mrs. Matthews? Mr. Horne? May I get you anything?”

“Finally!” Mason teased. “Yes, I’d love a tequila on the rocks, and a screwdriver for this one!” As Delilah came back with the drinks, she could tell they’d been giggling about something.

“Oh Sissy?” McKenzie was now practically on Mason’s lap with her hand on his chest. “Quick note, there must have been a mistake on the ticket. Please be sure to refer to us as Mr. and Mrs. Horne!”

The two of them laughed as a horrible sinking feeling flooded through Delilah.

“Yes Mrs. Horne! Of c-course!” McKenzie mistook her husband's distress for severe arousal, and kept doubling down.

“Oh yes, well we’re not married yet, it’s a bit of a scandal at home, you know how gossipy small town girls can be, I’m sure!” Oh, could she. A million group chats of high school girls followed their story religiously. “But who knows, maybe this weekend he’ll propose!” More giggles as Delilah flushed beet red. This was going to be the longest week of the sissy’s life, Delilah thought as she held back tears and scurried back to get them another round. 5

“Isn’t this so beautiful?” McKenzie was glowing. She’d suggested a little morning walk for the two of them the night before, and Delilah had been so excited to finally get some alone time with her wife, away from her wife’s nasty, cocky, jerk of a boyfriend...

Of course, this morning when she’d shown up at their hotel suite at 7 am sharp, she’d had to wait through twenty minutes of hearing Mason fucking her. McKenzie had stumbled out of the room giddily and wobbly, hugged and kissed Delilah (Mason laughed when she gave her a wet kiss on the lips, a laugh that confirmed Delilah’s suspicions about where Mason had finished that morning) and simply said “Good morning honey! Time for that walk!” with a smirk and a giggle.

Once they finally got out there, Delilah worked up a little courage. She was going to stand up for herself. There’s no way she could live with Mason in her life for a minute longer. “Honey, I need to- I- I want to say-”

“Oh honey, may I go first?” Delilah nodded awkwardly. “I just want to say how thankful I am for how much you’ve managed to adapt to this situation. Most men... or, people who were born men... would be in like total meltdown mode right now. But look at you, dear! Even your little swimsuit, your body, oh my gosh, I’m always so shocked how much it’s changed... you’re so feminine, but it fits you so well!”

Delilah was at a complete loss for words. She wasn’t sure how this morning could get any more humiliating.

“And, you know... when you first ran off to sign up to become a sissy when you got into that trouble, I wasn’t sure if I could make this work. But you’ve shown me how much you care about my... needs... and you’re clearly enjoying it almost as much as I am!!”

Delilah had no idea how to recover back to the idea that Mason had to go... would McKenzie choose Mason over her??

“H-Honey, yes! I love you!” She couldn’t help but ask... “You wouldn’t... have chosen him over me... would you?” McKenzie gave her a very non-reassuring soft smile.

“You know me better than anyone, Dak- Delilah. What do I want?”

“To... be happy?” McKenzie giggled. “Well, yessss... but I also want a nice home, kids, and to be loved! And I’ve figured out the perfect arrangement for all of that to happen.”

Delilah’s sinking feeling she’d had all trip reached it’s worst level yet.

“You’re my best friend, dear. That’s why I married you! But... like it or not, you’re not my husband anymore. I know they tell you sissies that you can go back to a boy life, but... I want to be with a man.”

“Mason?” Delilah whimpered.

“Yes. I love him, and I need you to love him too. You’re my family, after all! Except... not my husband. So, I am asking for a divorce. And I’m going to be changing my name, when Mason and I get married. But I did have a fun little idea...actually, it was your Mom’s idea!”

Delilah had no idea what about this could be fun. And her MOM already knew??

“Well, I’ll be McKenzie Horne. He’ll be Mason Horne. And if you’re living with us... I actually don’t think you can be Delilah Matthews anymore. How would you feel about taking my maiden name and becoming ‘Delilah Dockery?’”

“Delilah’s jaw dropped. Did she mean... “Don’t you love it?? You’d be my sister! Plus, it’s so much easier to explain you that way, as an Aunt....” Poor Delilah could only nod. “Oh how lovely! Mason will be so happy! I love you, sis! This is going to be so perfect. You’re literally the best sissy-husband-best-friend a girl could ever ask for. I’m so lucky!” 6

It was two years after the beach trip. Three and a half years after Mason’s betrayal sent Dakota Matthews running to Sissified Air to cover what he owed. Three years until that contract was up. One year since the divorce was finalized. One year and two months since Delilah had her name changed to ‘Dockery,’ McKenzie’s maiden name, accepting their new dynamic of sisters instead of husband and wife. One year and three months since Mason and McKenzie were married with Delilah as the maid of honor. Seven months since McKenzie FaceTimed Delilah, who had just spent three hours pleasing a group of very horny German investors, to tell her that she was pregnant.

Delilah Dockery had the day off. These days, that meant pregnancy errands with McKenzie and listening to her go on and on about Mason... the good (hot, big cock, wealthy, hot, good kisser, so into her, did she mention he’s hot...) and the bad (not super sensitive, too into sports, works too much, wants anal too often). Delilah suffered all of it, including McKenzie’s admission that she does like anal, just not all the time, not like “some girls I know!” as she giggled and poked Delilah.

It was true. Word about Delilah’s situation had gotten around. Her pilots, who had previously felt sort of bad about all of it and largely left Delilah alone aside from the occasional blowjob, told her they intended to make up for lost time now that McKenzie had come to her senses. One of them, Marcus had even been her date for the wedding! Honestly, that was actually kind of sweet, Delilah thought she’d go so crazy had she not had someone to go home with that night. A night of explaining how happy she was, really, truly, to be her ex-wife’s sister now was enough to make her willing to let Marcus fuck her doggy style twice that night. She’d been pretty tipsy, and started screaming out “Yeah Daddy... get me pregnant... get me pregnant... pleeeeeaseeee!!!”

Well, she wasn’t the only one begging her man to get knocked up that night.

Now, the pair of exes were out running errands while Mason was at work. Delilah thought often about how unfair it was that his rival got all the best parts of marriage while she did so much of the work. She supposed that’s what happens when you let your manhood and your marriage be stripped away from you.

“Hey, Di?” McKenzie looked a little nervous. “Can I ask you something?”

Delilah felt an uncommon surge of hope. Was she about to complain about Mason?? Did she...

“You know, I was thinking, when the baby comes... I mean... it would be confusing for them, if... I’ve never said this to you directly. You have no plans on switching back, do you? It would be pretty confusing... for everyone.”

Delilah knew this was coming. She’d accepted it. Hearing it from her ex-wife wasn’t fun, but... maybe it would be easier if she... just leaned into it.

“Switch back? To what, Kenzie? A smaller cup size? Brunette instead of blonde?” She giggled, and McKenzie did too, before breathing a sigh of relief as she put her arm around Delilah.

“Oh my gosh, hehehe, I love how much you’ve come out of your shell, girl. I’m so relieved. I should have known I had nothing to worry about, but Mason insisted I make sure there was no misunderstanding. When your little stint as a flight attendant is over, we want you to be our Nanny, full time! Mason can even pay you! I mean, not a lot, but about what you make now... nothing crazy, just cleaning around the house, watching our kids, letting me get some rest and relaxation... what do you say, sis?”

Delilah nodded along nervously. Nanny??? It sounded more like a maid! But, what choice did she have...

As if she was reading her mind, McKenzie giggled in her ear. “Mason wanted to call you maid, but I insisted we keep it as Nanny... unless you disagree, of course!! I bet some of your sissy besties have a maid outfit you can borrow...” She giggled. “God, I love you. I love how flustered you must be seeing me like this, all from another man, from my husband... hehehe! Oh my gosh, am I so fucked up? God, I’m lucky you love this as much as I do!” 6

“Hi there, maid! It’s just me!” Mason shouted from the front door. The fact that he called her ‘maid’ was enough to let Delilah know he was the only one home: McKenzie didn’t like it and would chide him a little if he called her that in front of anyone. Of course, she still treated Delilah as a maid, so what was the difference, really...

“How was your day, Master?” Delilah and Mason had their own little dynamic when it was just the two of them. “Delilah” and “Mason” became “Maid” and “Master,” anytime it was just them, whether that was a trip to the mall or a weekend where McKenzie went to her mom’s house. Delilah hated those the most. This evening, though, her Master was in a good mood.

“It was great.” He sat down at the kitchen island in front of her. “Bourbon, rocks.” Delilah scurried to fetch him his drink while he continued on about some deal he’d finally closed. Delilah had noticed that while she was sucking cock and serving drinks in her six year sentence as a sissy, her rival had gone from rich kid to quite successful. Delilah never thought she’d live in a house this nice. Of course, she never thought she’d be the maid to her ex-wife, either.

“Now, Maid- I need you to work your little magic with Kenz. She wants a whole date night routine on Saturday, but I have box seats at the Georgia game. So just suggest a little girls’ night or something. Tell her you really need some girl time or whatever, got it?”

Delilah nodded. Mason often used her for things like this. Just another little humiliation, what was the difference anymore?

Mason relaxed and loosened his tie. Delilah thought, not for the first time, that one of the worst parts of this whole ordeal is she both loathed Mason personally and found him very attractive at the same time. He’d even gotten bigger, more muscled, and poor Delilah had become so accustomed to serving men sexually that it was genuinely strange for her to not be on her knees for him. Unfortunately, Mason didn’t cheat on McKenzie. He even liked to tease that her last husband had been off flirting with men while they were married...

“By the way. We got quite the interesting three letters in the mail the other day. Kenz and I talked about it, and we’ve decided to put our decision on this up to a vote. Majority wins. Want to guess what I’m talking about?”

Delilah shook her head. She had no idea, but ‘majority rule’ in this house was never a good sign for her.

“Honeyyy, stop asking me, you’re well aware of the rules and you just don’t like them. If you want to break them and receive a punishment, that’s entirely up to you, baby!”

“Mommy, please! This is s-so humiliating, and if we wait for Daddy, it’ll just be humiliating for longer! I d-don’t wanna be here longer!!”

“Baaaaaby, I think you’re a little overwhelmed and you’re not thinking very clearly. And when Daddy asks me if you were intentionally disobedient, I am going to have to explain that you were very intentional. Is that really what you want? Do you really think Daddy’s punishment won’t be worse than some humiliation you’re already experiencing?”

For the first time in months, after begging and begging, Charles had been allowed to take out his car for a few errands and drive it himself. Formerly a prized possession, his Mercedes had been a special gift to himself out of his trust fund, just before he’d met Isabella. He’d felt so successful, so...

So when his Daddy gave him permission to drive a very pregnant Isabella around for a few errands, he’d jumped at the chance... even knowing it would mean his outfit would be... well, ringlets and ruffles and pink and made up, designed for maximum sissy exposure. Just like everything else in his life was...

Then the worst had happened. He hadn’t driven in almost a year! The car had barely been touched, just a few times, always Daddy driving, and it stalled out, forcing Charles to drive it to the nearest service station, knees wobbling with humiliation as a bunch of mechanics watched him and his very pregnant wife exit the vehicle. The worst part of his wife’s... condition... was that even when Daddy wasn’t there, he might as well have been, because nobody, ever, assumed he’d knocked her up. Many didn’t even assume he could if he tried. He had to get out of here. He decided no punishment was worth stewing in this sweaty room with all these eyes on them... he stood up. His wife giggled but didn’t say anything.

He knew he’d made a massive mistake as the receptionist at the counter and one of the mechanics behind her burst into laughter before he could even say a word to either one. “So, we heard every bit of that.” The receptionst said through giggles. “It sounds like you don’t have permission for us to begin work on this car!”

“N-No, she was just, she was ki-” He spun around, and his wife shook her head as if to say, I’m not helping you.

“That’s absolutely right!” Isabella giggled and shouted across the room without getting up.

“N-No, no no, look in the glovebox, it’s under Charles Wh-”

“CHARLES? Hehehe, well I don’t see a Charles! Go sit down, honey. When your Daddy gets here, I’ll speak to him.” The receptionist and Isabella giggled as Lottie minced back across the dingy lobby in shame.