Blossoming Sissyhood

“I don’t even... I can’t... you shouldn’t even be here!” Luke whispered the last words in a way that was almost a hiss. Agent Marstow couldn’t really blame him. More noticeably, he couldn’t even really recognize him!

“Luk-” Before he could even say anything, the blonde’s eyes went wide, he put his hand over the Agent’s mouth, and dragged him into a side alley. “Did anyone see us??” The blonde was looking around frantically. “If anyone sees me talking to a fucking FBI agent around here... I’m sorry, but like, I can’t risk this...”

Marstow gasped as his witness started to get on her knees and undo his pants. “What the fu- Lu-”

Again, Luke popped up to silence him, this time by planting a wet kiss on his lips. “Don’t say my name, you fucking idiot!” He continued kissing his neck a little. “We can talk like this... Papi’s across the street. He knows some of the guys like to kiss first...”

“Who the fuck is Papi?” Marstow whispered.

Luke kept kissing the Agent’s neck. “Papi’s my fucking pimp, you idiot.” He licked up his ear. Marstow was tingling, now. This little crossdressing whore was quite good. Except, he wasn’t supposed to be that. He was supposed to be living in a safe house and working as a waiter in a bar.

All this because, a year and a half ago, he’d realized the firm he worked for was laundering money for one of the worst gangs in the city. He thought the FBI would welcome him as a hero... instead, they barely seemed to care, while the gang he snitched on found out. So he was stuck. No case on the people who were after him was moving, and he was in a lot of danger. When he begged for protection, his uppity attitude had landed him here, in the very neighborhood where he was in the most danger. “Hide in plain sight,” he’d been told.

“You all thought it was sooooo funny, didn't you?” More kisses. “Put the finance bro nepo baby rich kid in this neighborhood... make me work a menial service job... I remember hearing how you all talked about me...”

Marstow now felt really terrible. That was true, actually. It was also why when they stopped hearing from Luke, it took awhile to get around to him. “Luke...”

“Stop... using... my... fucking... name...” The kisses between each word were starting to drive Marstow crazy. “It’s Lola. Understood?”

“But... if you do this... don’t they know?” Marstow regretted the question as “Lola” gave him a look of pure hatred. She flipped up her skirts and shoved the Agent’s hand down to let him feel the tiny cage around his cock. “They know I was born with this. They don’t care that I don’t WANT this. Enough foreplay. Tell me when I’m getting out. What’s happening with the trial??”

“N-Nothing... this is just... a check up... you’re not being removed. I can put in an application, but...”

Lola looked like he was about to cry. “Papi’s one of them, you know... you fucking asshole... you’ve got your witness working for the people I’m supposed to snitch on... as a fucking sissy whore!!!”

Agent Marstow really did feel horrible. Unfortunately, what he felt even more than that, was... aroused.

1

Nick was a positive person. He always believed that everything would work out for him, and he worked extremely hard. He’d grown up a nerdy, lower-middle class boy, but was incredibly intelligent and even quite modest. After graduating from college with a business degree, he took a high-paying job at an insurance company in his hometown, one dominated by some very boorish and masculine men who loved golfing, hitting on their secretaries, and getting drunk.

Nick saw this as an opportunity to advance. Surely these men who were so lazy and entitled could be brought down. A bunch of right-wing entitled rich guys brought out the competitor in Nick. He even got a little drunk at happy hour and told everyone he wanted his boss’ job, and he deserved it. That was right around the time his boss took a flight on Sissified Air, and decided to take action. Poor Nick soon found his name on a bank account that had been used to embezzle over $1.5 million from the company. Every single executive swore he was a thief, but they had an... idea, rather than to press charges. 23 year old Nick was forced to sign a contract that ensured the bright and hardworking up and comer would be in skirts and heels for twelve years.

But the poor sissy-to-be took his fall better than most. He didn’t lose hope when one of the other sissies-to-be in his training class, a former attorney, told him that he wouldn’t have recieved more than a year given his history. He held back the tears when his sweet girlfriend Emily insisted she needed a break, but that they could stay friends. He even kept a brave face when he realized that for the first time in his life, he was one of the worst students in his program. Academic smarts and a quick wit couldn’t do much for you in a program of  cosmetology, etiquette, and obedience.

So, poor Nikki Cherry graduated at the bottom of the training class for Sissified Air. It didn’t matter much except to hurt his pride: it’s not like there were raises or promotions available for the sissies. He told Emily some silly line about how he’d learn every bit of the industry, listen to the businessmen’s conversations on the flights, come out of it ready to re-join the professional workforce... the pity and barely withheld laughter in her voice didn’t dissuade poor Nikki.

Now he found himself click-clacking in heels through the airport, carrying a suitcase full of makeup and outfits just as skimpy as the one he wore, humiliated beyond his ability to consider as his dreams of being a high-flying businessman turned into a reality of mincing steps and leering men. His need for praise and recognition was bubbling up as it always did, but this time, he knew it would only come through being the best and most submissively sweet sissy he could be. It would all work out just fine, he thought to himself. He introduced himself to the pilots- “WOW! This might be the hottest one we’ve had yet,” leered one. He checked the manifest, hoping it would be a group he could learn something from- only to burst into sobs as he saw his former boss’ name, Tim Reynolds, and his old company. He’d spent the last nine months doing his best to ensure nobody would see him finally break, and he lasted all the way up until the moment that mattered most. Tim laughed as he walked in to see his former competition sobbing in skirts.

“Well, good things happen to good people, I suppose!” He laughed, referring to himself. “Nikki, get me a drink!” Nikki snapped to attention and swayed her hips, handed him a bourbon, and for the first time, realized just how fucked she was.

2

“She’s pretty cute!” One of Nikki’s pilots, Logan, laughed as the mincing sissy showed off a picture of his ex-girlfriend Emily. “Does she know you don’t even travel with the key to your own chastity cage?”

Logan and his co-pilot Colton burst into laughter. The three of them had grown quite close, because like all Sissified AirSissies, Nikki was a dutiful little cocksucker for the both of them. Long layovers, lonely nights in hotels, boring lunch breaks... poor Nikki spent them all on her knees for the two of them.

“She looks like a good girl.” Colton jumped in. “So I’m guessing you didn’t learn to be an expert cocksucker from her?” Nikki blushed beet red. It was true, he’d only ever talked her into it once, for his 21st birthday. His 24th had been spent in an airport hotel, with Logan in his mouth and Colton up his ass, waiting for a group of Russian businessmen to finish up a deal before spending another 14 hours in the air listening to them call him all sorts of Russian words that he now knew meant weak, effeminate, and prissy.

His dreams of corporate eavesdropping had been for naught. For the most part, any real business was done while he was so busy fetching drinks and flirting with men that he hadn’t picked up on a thing. Worse still, a few pictures of his new look had gotten on Instagram, and his few remaining friends from high school told him that one of them had over 150 reactions in an alumni group chat. He couldn’t bear to open the group chat... but was reminded of it almost daily now, as every guy who bullied or mocked him DM’d him now, up to 10 a day. Even worse, the bullies weren’t the most persistent: the worst were the boys who he’d been superior to, nerds in his friend group he’d always been smarter than. It got so bad, he had his notifications off almost all the time. Scrolling through one day, his heart leapt as he saw Emily’s name! “Hey babe... hope you’re hanging in there 💕 I’ll be in the Dallas airport soon!!! Drinks??? 💋”

“See?? She totally wants to get back together!!” Nikki excitedly bragged to the pilots. They each took a look at each other and laughed. “Oh yeah? You think so?” Colton said with a mean look, and Nikki’s heart sunk. “If you suddenly get a girlfriend, you think you’ll be able to get out of serving us?” Nikki’s face went white. “You think she’d be okay with you sucking cock 7 days a week?”

Logan was even more stern. “If you dare act like you could be a faithful sissy boyfriend to her, you’ll majorly regret it. Enjoy those drinks, sissy.”

Nikki arrived at the bar completely humiliated, as Emily’s eyes went wide seeing what her cute ex-boyfriend had become. Eager to move past the discussion of how Nikki now had breasts much larger than hers, Nikki couldn’t take it anymore.

“Babe, I’m so so so glad to be with you again, and I so want to get back together, but-” Emily’s eyes went wide and she stifled a giggle, but Nikki didn’t notice. “I have to tell you... I have... duties, to perform, with my pilots... they’re sweet guys, I swear, but it’s just part of my job...”

"All I want to make sure of is that you truly want this.” A sweet, magical Cupid, pigtailed and with fairy wings, fluttered in front of the blonde boy with his tie loosened.

The boy, Ollie was frustrated with the little magical fairy. “Of course I want this!! You’re supposed to give me everything I want!!” The excitement, the disbelief and joy he’d felt when the little thing appeared, his pathetic dream actually come true, whether it was Cupid or a fairy or what, Ollie wasn’t sure. All he knew is he’d wished on his lonely night to finally get everything he wanted. No more loneliness. No more Valentine’s Days spent alone!

Ollie had it all, but it never felt that way. He’d gone to the best schools, done it all right, undergrad to law school to a prestigious firm. Except it didn’t feel that way spending every night alone in his fancy apartment. His Cupid finally appeared that night when Ollie was deep in a bottle of expensive Bordeaux wishing, pathetically, that he had a Valentine.

“I just have to insist you understand,” the fairy continued. “I can make people fall in love, sure, but what truly builds happiness is when I construct a reality where you both truly need what the other is. A completely compatible relationship that’s most suited for you personally. For some people, that can be a bit of a shock. What your heart is most suited for is almost never what you’d expect.”

Ollie was drunk, lonely, and had a mental image of maybe a hot blonde who was a little fatter than he’d prefer or something. Who cares. “OBVIOUSLY!” He’d shouted. “Just... do it! Give me a loving relationship. I’m ready.”

Ollie’s Cupid smirked a little. Some cases were harder than others. Many of the people whose wishes she granted were deserving sweethearts who just wanted love. Then there were the Ollies: entitled, stuck up, not really marriage material for most without some serious changes. Ollie wasn’t evil or cruel, just a bit of a brat. Brat... that made her think of one of her more deserving men of the day. But she... why not? Ollie would be perfect, actually. She was sure he would disagree... for now, anyway. Had he annoyed her less, she might have been reminded of Megan: the perky redhead who specifically said she wanted a rich lawyer whose cock she could worship. Oh well!

Instead, she was reminded of Dave, a sweet divorced man with a sissy kink and a Daddy vibe. She’d make Ollie suddenly obsessed with the idea of being a sissy... connect them online... deepen both of their feelings for one another... Ollie would need some serious pushes to being the type of sissy Dave wanted, but she’d made more dramatic changes...

“Look Daddy...” Olivia purred in Dave’s ear. “It’s snowy! So pwetty!”

The now failed attorney giggled as her Daddy patted her diapered bottom. “That’s right baby, snow! Do you wanna go play in it later?”

“Hehehe... noooo! So cold! I want Daddy again later...” Olivia giggled and nuzzled her head into her Daddy’s warm chest. She’d had Daddy six times that day already. For a man in his 40s, Dave wanted it as badly as anyone she’d ever met. Certainly more than she’d been able to, back when she was playing grown-up (a perfect term her Daddy had given her for her time before meeting him!)

#1

“Can I ask you something? I hope it doesn’t sound...” Marcus seemed a little unsure for the first time tonight. It made Maya somehow even more attracted to the man, which she didn’t really think was possible.

“Does it... does it offend you, that he... well, that your husband... husband? Again, I don’t mean to offend. Does it offend you that he doesn't want to... be with you, anymore?”

Maya threw her head back and laughed. “Can’t, darling. It doesn’t offend me because he is not capable of being with me, which is a decision I could not have agreed with more.” Marcus appeared a little more comfortable. “It’s perfectly reasonable that you’re so confused by it, because you’re a real man, Marcus. Honestly, it’s a red flag to not be confused by it. One sissy in my life is plenty, I have no interest in another!”

“Well I’m... I mean, I’m not...”

Maya laughed again. “Honey. I know.” They both laughed a little and sipped their wine. Maya liked this one, she thought. She liked him a lot. He ticked basically every single one of her boxes. Drives a truck, check. Masculine job, check. (Fire captain? YUM!) Big hands, big arms, big feet? Check, check, check. Notably, all her new boxes were things her husband would have failed when they’d been dating. Speaking of, her last one... accepting of the fact that she was married to a sissy baby? To her surprise, it seemed like a check! Time to test the waters a little...

“Now that you understand, I have to say, I never call my lovey by male pronouns or my husband. She‘s either my sissy, my baby, any cute pet name, or her name! I’ve only ever called her Bella for years now when it’s just the two of us, and basically always since she came out. She loves it. Sound good?”

“Bella it is.” Marcus smiled. This was good.

“Wanna see her?” Marcus nodded and appeared genuinely curious. Maya gestured him over to her side of the table and sidled up to him a little. Oh, it was going to be fun later. She could tell.

“Here she is!” Maya opened her phone to a picture of a pigtailed sissy baby, diapered and wearing a baby blue frilly dress, who appeared genuinely upset as she spooned some sort of mushy meal into her mouth.”

“She hates those peas! Except, she begged for no adult food. Everyone wants strict rules until you’re eating Gerber’s while your Mommy prepares for her Valentine, am I right?” Marcus appeared both stunned, and... Maya got excited. He was into this.

“Enjoying this? Because that was literally only a few hours ago. We could go back to my place and see her after this. What do you think?” Marcus simply kissed his date and she flushed. This was shaping up to be a perfect Valentine’s day gift for both her lovey, and her lover.

#2

“What’s the matter, sweet darling? Getting a little too much of what you dreamed of?? I think I’ve re-created your fantasy quite perfectly, right up to the final moments anyway, which you’ll just have to tell me all about tomorrow!”

This little teasing created more tittering from Peyton’s friends and more all-out panic from David. For a weak-willed sissy like him, there’s no feeling worse than being unable to resist a worthy punishment. Poor David certainly deserved everything he was getting. He’d even wanted it, once upon a time.

He hadn't been an awful boyfriend to Peyton. Last year, he’d gotten her flowers, they’d gone to dinner, they’d made love afterwards... but she always had a suspicion that something was off. She’d assumed cheating, or maybe even just an emotional affair he was having with some other girl. What she discovered in his phone that night was far worse: her boyfriend was a full blown sissy. No wonder she didn’t feel like he was attracted to her, she thought as she read message after message to other sissies on Tumblr. David laying out, in detail, his type (older, working class, dominant men) his style (prissy and sissy to the max) the hidden personality he was keeping inside (a mincing, pathetic sissy). Her jaw dropped at some of these messages, it was an explicit side of her boyfriend she’d never seen. When she read her name, it was usually in the context of how guilty he felt about leading her on, how hot she was (she loved that!) and how ideally she’d start fucking “Real Men” so David wouldn’t need to feel as guilty.

Well, she thought... that didn’t sound like such a bad deal. In fact, all of this sounded pretty fun to her. So, she started to make David’s fantasies a reality, from microdoses of hormones to suggesting they explore gender play. Seeing him gasp, blush, and spurt when she called him a ‘pretty sissy’ while stroking his cock made her giggle too much to hold back the truth any longer. She confessed she knew everything, and nothing short of making every fantasy a reality would suit her.

Now, a year later, David’s ultimate fantasy was coming true. A Valentine’s Date with an older man while Peyton and her girlfriends giggled and went out with their own men. He wanted to pout and deny it, the reality of it felt far more humiliating than he could bear. But there it was, and there he was, aired out as a sissy to his lovely girlfriend. In preparation, he underwent the makeover. He hadn’t noticed just how soft and feminine his body had become until truly seeing it dolled up.

Peyton, seeing her boyfriend for the first time as his true sissy self, knew she’d done the right thing. “Are we ready for the big date, Prissy?” The poor sissy cringed hearing his ridiculous sissy name spoken from her lips. He nodded meekly.

Sissified Air. It was one of those things people in the industry would joke about to one another. ‘That pilot is such an idiot, he’d be a better fit with Sissified Air!’ ‘God, this flight crew are such ditzes, you’d think I was a pilot for Sissified Air!’ ‘Did you see Jim drunk at the bar last night? He was groping one of the bimbos from Sissified Air!’ The thing is, though, some people actually did know a few cautionary tales. That’s because the top priority targets for Sissified Air corporate to hire for their flights- all private charters, obviously, for the wealthy and devious clientele, were in fact former, male, pilots. They even laid it out in their handbook for new hires.

The perfect Sissified Air Sissy Attendant is a young man, between 25 and 35. He should have a college degree, formerly a member of the upper middle professional class, a hard worker who is accustomed to dealing with our usual clientele of successful businessmen. His former position should be one of status: executive, attorney, or best of all and most preferable; a former pilot or rival airline executive. Their ‘descent’ from status to sissy, we find, makes for the very best of our Sissy Attendants.

Well, Jim Hardgrove had been a pilot. He’d wanted to be one his entire life. At first, he just thought planes were cool! Then he got older, and a life of hotels, cute girls, and nights away from his highschool sweetheart Courtney became more and more appealing. Except, Jim wasn’t quite the ladies man he thought he was. More of a sissy’s man, it turned out, and he realized that the Sissified Air girls were really easy to get into his hotel room. That was until word got around among the sissies that his cock was much smaller than his ego, and they stopped being so eager. Jim didn’t take that well, in fact, he was so angry with one of them for rejecting him that he grabbed the poor sissy and spanked her, right there at the airport bar, laughing as he said “Bad sissy! bad sissy! You still wanna say no to me?”

Nobody had ever accused him of being a genius, and the video of the incident went a little viral. Some used it as a rationale to go after Sissified Air, which to them, just wouldn’t do. So they decided to teach the cocky, arrogant loser a lesson. He’d be fired, charged with assault, and go to court to defend himself, or... a 10 year contract. He was the perfect candidate. Arrogant, dumb, and completely trapped. Courtney took it pretty hard at first. She was humiliated! Her successful husband had been fucking and abusing sissies, and now he was going to become one? Obviously, she called a divorce lawyer immediately, and it was finalized right around the time Jim graduated from the training program with his new identity: Gemma Sky, a name fit for a life spent bringing drinks to bachelor parties and seedier corporate trips.

Gemma was now three years into her ten year deal. Her cock had been caged for so long that what was once small was now permanently ruined. Her tits strained against her uniform, her lips were perfectly plump and glossy, her blonde extensions perfectly done. Even her voice had changed, as using their man voice was one of the worst offenses possible. It wasn’t until all that had become second nature that a special request for Gemma came through. These were common, usually men who’d loved her before would request her again. Wondering who it would be from, Gemma’s heart skipped a beat when she saw the name and occasion. Courtney Hardgrove – Bachelorette Party.

“Another round, SISSY GEMMA!” Courtney cackled with laughter as her and her friends kept Gemma so busy the poor sissy could feel her sweat dripping down her cleavage. Courtney hadn’t even acknowledged any relationship they’d once had, she’d engaged with Gemma plenty, but only to order the poor ruined sissy around and brag to her about her new fiancé. Gemma wanted to curl up in the lavatory and sob as she minced up and down the aisle, cock caged and ass plugged, hearing her ex-wife tell all the girls present what a stud her new man was. “Trust me ladies,” she’d giggled. “Being stuck with one, ahem, ‘man,’ for so long, I didn’t know how big they got! I don’t know how he stuffs it in his pants!”