A Sissy Cinderella Story

Caption #1:

Cameron's wicked stepmother ran a cleaning service for the rich and famous, specializing in mansions and other large undertakings. To especially appeal to the traditionalist and old money clients, she made each of her workers dress like classic maids.

Naturally, not a lot of people wanted such an embarrassing and laborous job.

With Cameron's stepsisters too spoiled to work at all, he was forced to do the job for free, forced to pretend he was a girl, forced to be his evil stepmom's whipping boy.

But everything changed one day while he was cleaning up some old money estate. "You need a date to the gala! I don't care if your latest floosey got boring, you RSVPed plus one" exclaimed the father of this wealthy family, as his rakish son stood there and listened.

"Who cares? And it's too late to get a new date anyway."

"I care! Appearances matter. You have to learn that. Find someone. Anyone!"

Grinning slightly, and happy to test his dad's definition of 'anyone,' the son turned to Cameron. "Hey, are you free tonight?"

Caption #2:

Dean's father had tried to talk him out of dating the help, and Cameron had tried to talk his stepmom into making an excuse, but the date was happening. Dean needed a plus one and Cameron's stepmom didn't want to lose a client, so 'Cindy' stood there waiting after what seemed like a full day at the salon.

No more wigs. Extensions were put in his hair.

No more hiding his legs under stockings. He'd been thoroughly waxed.

They even glued on breastforms, blended to his skin with makeup to look like the real thing.

He felt like such an idiot as he stood in the hall, finally seeing Dean come out the elevator. "You clean up good" he smiled, politely looking her over.

"Well, I am the maid" they joked in reply.

Dean chuckled and extended a hand. "I know you might not want to be here, and I didn't want a date but...let's have a good time. Stick it to my dad...maybe even have some fun?"

Cameron looked down for a moment, thinking about how long it had been since he had a night not working for his stepmom. "I think I'd like that."

And he took Dean's hand.

Caption #3:

The date at the gala had been...fun?

Other than Cameron being a boy who was leading Dean on so that his stepmom wouldn't lose a contract, they got along well. They had a lot of the same interests, the same sense of humor and found it easy to talk to each other. Cameron hadn't really been able to hang out with anyone outside his stepmom and stepsisters, so it was nice to be around someone who actually treated him nicely. He even opened up a bit about his dad passing away, which he hadn't done with anyone in the year since it'd happened.

However, a great date wasn't entirely good news.

Dean had called the house the next day, and 'Cindy's' stepmom had told him that she'd love to go out again. She was so serious about it that she made Cameron talk, dress and act like a girl at home to stay in character, all while his stepsisters wistfully asked themselves why Dean Lugwood wasn't asking them out.

This date was much more low key than the gala, with Dean taking Cindy out for a walk on the boardwalk. The wooden planks made her heels even more annoying as they walked together and Cameron had gotten a smaller ice cream than he wanted to keep up the girly act.

Still, Dean was smart, funny and easy to talk to. 'Cindy' was telling him so much that it was almost hard to keep the lies straight, and to remind himself to change details so he was telling a girl's life story.

"I'm sorry, you don't want to hear this..." he trailed off.

Then, Dean stepped in front of him, taking both their hands in his. "Don't ever tell me that. I want to hear all about you. Everything there is to know. And if you can't tell me now...I guess I'll just have to keep buying you ice cream."

Cameron blushed, looking down from Dean's smile for a moment before meeting his gaze. What the heck was this feeling?

Caption #4:

As strange as it might seem, being with Dean was the happiest that Cameron got to be. They'd been going out for a month now and despite his playboy reputation, Dean had been the perfect gentleman. All they'd done was kiss outside the door when Cindy was dropped off, a kiss that was like fireworks and lighting going off all at once.

But Cameron's stepmother seemed happier than anyone else. And as Cindy came in, as if walking on a cloud, she explained why.

"Wait, you want me to bring one of the girls on my next date and talk them up to Dean before breaking up with him?! Are you crazy??!"

"We can't keep this lie up forever, but you can give your stepsister pointers to woo him. Then, I'll have a daughter that's married into one of the richest families in America" she explained with a cold, logical tone.

"But Dean is...Dean wouldn't go for them. He's not like most of these rich jerks."

"Well he went for some brat of a sissy that cleans his house" snorted the stepmother. "I'm sure he'd go for a real woman. So listen and I'll give you the-"

"NO! No, I'm not helping you! I'm tired of helping you! You work me like a dog while your daughters do nothing, you treat me like dirt and act like I'm just supposed to make you money and it was a mistake for my dad to ever marry a b-"

SLAP

Cameron's stepmother was a bit shocked at herself, mainly because Cindy couldn't take part in this plan if she had a black eye. But when she saw her sissy stepdaughter looked fine, she shook her head. "You're going to do as I ask or you're going out on the street, you ungrateful brat. It's midnight. Your tits were going to turn back into pumpkins sooner or later."

Caption #5:

It was their two month anniversary, and Dean was so head over heels that he got all romantic about the day. His plan was to take Cindy to the hottest restaurant in town, wine and dine her and hopefully take her home.

Cameron's plan, despite his protests, was to run into Sarah, the stepsister who'd won the cointoss, and try to start this tradeoff. Knowing it might be Cindy's last date with Dean, she got herself all dolled up, and greeted him with a deep and loving kiss. He complimented her dress, made her blush, made a big romantic deal out of everything in a way that stirred up butterflies in Cindy's stomach.

He introduced her to all of his rich boy friends, grinning wide as they told her that Dean never stayed with a girl this long. Then, as they waited for their food to arrive, Dean gave her a string of pearls that were probably worth more than rent in his stepmom's apartment.

With it around her neck, Cindy sawe a message from Sarah on her phone. She was waiting for the signal. The end was about to begin...

"Cindy...this might be a bit forward" said Dean. "But I know."

"...excuse me?" asked Cindy innocently.

"I know about Cameron and about your stepmother's charade she has you do for clients. I've known for a while."

"Dean, I...I..."

"No, Cindy. Don't say a word. I don't care. I like you. I like you a lot, more than I've liked any girl. And I know how your stepfamily is. I guess what I'm saying is...if you want to be Cindy. I can help you. We can end this here and now or...or you can be my girl. For real."

Despite all he'd felt, the full weight of that ultimatum hit Cameron like a ton of bricks. Becoming a girl? Transitioning? Forever? Being Cindy for the rest of his life...it was just too much, just too permanent. As an almost knee jerk reaction, he shook his head. "I'm sorry...I can't."

"I see...well, it's been fun" said Dean with a deep sadness. Cameron wanted to comfort him...but he just let them walk away.

Caption #6:

Cameron was grounded for ruining the plan. He didn't have money of his own to begin with, not even a credit card or loose change. He was trapped, hopelessly trapped in his stark bedroom as he tried to sleep.

But he couldn't.

He couldn't tell himself he'd made the right choice, couldn't put tonight out of his mind. No matter what he told himself, the feeling was still there, overcoming any logic.

So he took out the pearl necklace, hidden so that his stepmother wouldn't confiscate it for herself. He'd wanted something to remember Dean by but as he teared and sniffed, thinking of their time together...

He knew he wanted more than a past with him.

He wanted a future.

So he snuck out onto the fire escape, making his way to the all night pawn shop and getting enough for a taxi. He knew how to get onto the estate grounds after so much time working there, so he snuck his way to the mansion until he saw Dean, sitting mournfully on the back patio.

"Cindy! I mean...I guess Cameron?" he said, sitting up with a start.

"Dean...I was wrong before. It was so fast and I was scared but...I'm scared all the time. I'm scared of this decision. I'm scared of my stepmother. I'm scared that I'm never going to be anything more than her workhorse but... I'm scared of everything, but being scared is okay when I'm with you. I want boobs and estrogen and all that because I've never felt more right than when I was your girl. I want to be yours. I want it. I want you."

Dean sat there, staring in shock before standing up and walking over.

"And I understand if the offer is gone. I lied to you and said no and-"

Dean cupped her chin and kissed her. "I love you, Cindy."

She smiled.

"I love you too, Dean."

Caption #7: 

"Dean! Hurry!"

Cindy and Dean had been together for two years, and married for one. It was a wonder what doctors can do when you marry into one of America's richest families and by now, Cindy was hotter than any of her stepsisters.

Something she never failed to remind them of.

She often thought of them in those ugly bridesmaid dresses, scowling at her as she said 'I do.' To think how much they mocked her when they glued those first breast forms onto her, and how jealously they looked at her cleavage in her strapless white dress.

But right now, she wasn't thinking of them. She was only thinking of Dean.

Ever since that night they both put everything on the table, Dean had shown her why he was known as such a lady's man. He was still a gentleman, just a very hot and hunky gentleman who knew how to make his darling wife moan. At the galas and parties, they were the most enviable, romantic couple of all the glitterati. But in the bedroom...

"You think I'm not hurrying?" he smirked as he walked into the bedroom. Cindy bit her lip as his towel dropped.

"You still kept me waiting..." she smiled, her C cups poking slightly above the bubbles.

Dean climbed in, kissing her on the neck. "I guess I'll just have to make it up to you. Any suggestions?"

Moaning at his touch, Cindy could only be thankful of all she'd gone through. All the pain and mistreatment, all the doubt and trouble...it had led her here. It had led her to him.

"I have some ideas..." she purred.

And they both lived happily ever after.

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That's the end of Cindy's story (but perhaps, only for now) so I'd love to hear what you guys thought!