The Dress-Up Mess-Up

 

Looking At Me

 Wow, keeping up with a caption a day is hard, especially since Secret Boyfriend and Becoming The Fake ID's sequels are both feeling too big for single caps. So I'm gonna try and sneak in some shorter still image caps to fill the gaps. I had a bunch of ideas, but it's hard to keep up with them! Even if I don't get anything done until those sequels next week, we still have the next installments of Tricks, No Treats every even-numbered day of the month! 

The Moves

 

A fun lil' one. As I'd hope you all know, Halloween is coming up and I'm hoping to do another caption blowout, I conjured up some fun AI pictures with spooky themes to make a few, but if anyone has any GIF suggestions (or scenes I could turn into GIFs, I'm a slight bit more technically savvy than I was then!) Or story ideas they'd like me to try to elaborate on, send them to SydMixUp@gmail.com or comment here. As always, I might not get to every idea, but I'll do all I can. Look forward to hearing from you. 😀 

XOXO

-Syd

Everyone tried to warn me, but I thought it was ridiculous. Why would Anthony try to put the moves on me!? He could have any girl he wanted, and I say that as his best friend who has watched him bed every chick, bimbo or brilliant, buxom or bratty. He'd pick a target and charm the pants off them within the week. He tried to teach me a time or two, but I just didn't have the money he had. Or the height. Or the frame. Or the mass. Or the confidence. Or the experience. But I'd be able to swing by his apartment in the morning and see them wander around the house in their undies, awash in leftover ecstasy from the night before. Let's just say a lot of deposits were made into my spank bank from that couch. 

But recently, things have been a little different since I got my new job. Finding a new job was tough, especially for someone as meek as myself. My Aunt offered me a job, but she mentioned her company had enacted a diversity quota. If they could get another woman of color, it would mean a bonus for all of us, and that would help me catch up on the back rent hanging over my head. So I agreed. My Aunt could turn me into her new office girl.

My training period consisted of teaching me to carry myself as Amy. As I worked through it some of Anthony and my friends stepped in to help. They were all women, all of which I had crushed on at some point and all of which I had watched stroll out of Anthony's bedroom at some point. Within the ending of my training period the practice, Hormones, breast forms, and tuckjob made me indistinguishable from other women my age. If anything I looked a bit younger. But I noticed Anthony being nicer, grabbing the bill for lunch (which he usually did, but while making fun of me for being broke beforehand), letting me vent about my day, and complimenting my skirts and dresses. I should have noticed initially that he liked the shorter ones.

The other girls we hung out with began to tease me about our flirtacious interactions, but I kept telling them I didn't know what they were talking about. Then when he hosted a game night, I walked past his chair and he pinched my ass. The fact I turned, giggled, lightly slapped his muscular, chiseled chest in that tight t-shirt and said "Stawp it!" Like a smitten teenager hurt my masculinity more than wearing a bra, knowing how to walk a flight of stairs in high heels, having a preferred selection of cosmetics, and looking at a smooth front to my frilly panties in the mirror every day for the last few months ever could. I left and didn't respond to any of his concerned texts or any of the girls asking if I finally got what they meant.

I buried myself in work for the next week. Coming home, changing into my nightie and lying in bed at night. Replaying those events in my head and cringing at how I let him treat me like a girl. Then my panties started to get tight and I'd toss and turn, imagining confronting him... but couldn't help but imagine him doing the dumb thing he does to avoid responsibility every time he upsets a girl. Where he just makes that dreamy look and draws in closer. Wrapping those thick arms to hold them in place. Whispering "sorry" as he rubs the bristles of his beard across her forehead. I mean her forehead. While pressing his bulge against her stomach, he loved short girls. And whispering "hey" until they look up, then following it up "I'm sorry" before tenderly kissing me, I mean her, and when I get to that point... I finish. No hands. Shouting in surprise and pleasure. It happened Monday. It happened Tuesday. It happened Wednesday. It happened Thursday. I'd clean up, change my nightie, and go back to bed. I'd peacefully sleep and wake up before spending the day feeling ashamed and confused before doing it again. 

Friday rolled around and asked me to join him and the girls for a movie night. I asked around and he hadn't asked anyone else. He was trying to corner me and make his move. I thanked the girls for the heads up and ignored them asking if I was still going to go. I planned to give a piece of my mind, but I made sure to make a quick last-minute salon visit and pick out a cute outfit, you know, to look cool while I put him in his place. 

I arrived, he had candles lit, my favorite takeout on the table, a romantic comedy ready to play on the TV. "Oh hey," he said unconvincingly, "the girls couldn't make it, but I already bought this movie so I guess we're stuck with it. Oh and I had to spray the chair, spilled a drink, so we can share the couch." I was ready to bite his head off but he went to so much effort that I found myself next to him pressing play before I knew what hit me. I regained my wits when he tried to put his arm around me and accused him of trying to seduce me. Even though he knows I'm really a boy.

"It's just... Amy... It's so hard to remember that when you're more beautiful than every woman I've ever met. Plus you're so cool, I know we get along, we have a connection that neither of us has ever felt... I just thought that... We could try." I tried so hard to remain serious, until it became clear that I was blushing and smiled. He smiled, knowing he charmed his way out of consequences once more. 

"You say that stuff to all the girls." He smiled. I called myself a girl. He was going to hold that over my head as he started toward me. And I'd never felt more vulnerable. His whispers dancing down my body, giving me goosebumps. His strong arms locking me into place, preventing me from running away from this. My head against his chest, breathing in his scent. Looking down as his already-prominent bulge grew and size and temperature and pressed against my stomach, only separated by the thin fabric of my shirt and his pants. Then I heard it.

"Hey" and I looked up so fast that I think I actually kissed him first. My smooth soft face felt the scratch of his beard and I lost it. I trembled. Moaned. Went limp in his arms. I excused myself to the restroom and changed into the spare panties I'd packed into my purse and returned to him. There was no denying anything now. I stared at the floor embarrassed. But he comforted me and said it was ok, he convinced me to stay and said we could go slow, we didn't have to do anything I didn't want to. He'd never waited more than a night to get off... Maybe he was serious. I sat back on the couch and let him put his arm around me.

I never did see how the movie ended.

RBF

 Another attempt at the new method, tried a few things differently. Let me know how it looks. Also, a little proud I gave a double meaning to "RBF"

I walked out, swinging my hips and clicking my heels to greet my Aunt, I smoothed my skirt and sat obediently on the couch across from her in the den. I crossed my legs despite the dull pain it applied to my shrunken and now-useless member. The weight of the budding breasts from the hormone treatments I'd agreed to and my long, styled hair were a constant reminder of how much I'd changed since getting here. The make-up on my face I put so much time into practicing that I could do it in my sleep was a skill I wasn't proud to possess. I cleared my throat, making sure i was going to hit my girly voice properly and said "what do you think, Mother?"

Obviously, she was my Aunt, not my Mother. And not by blood, she married my rich, aging Uncle for his money. The same Uncle who was my insurance policy if things didn't work out for me in life. Unfortunately, I heard through the grapevine that she had come along and now everything was going to her. I came back to get on his good side, but he was all but checked out and I was at the mercy of Ellie, who was only 15 years older than me but a handful of decades younger than him.

At first she wrote me off, but I was desperate and was willing to fight her on this. But I couldn't afford a lawyer and had very few cards to play. So when she said she'd put me back in his will if I played along with this little scenario of hers, I agreed and was bombarded with contracts. She said she feared the time had passed, though she always wanted a child of her own, and if it was one related to her husband, all the better. I agreed, not realizing that the contracts all specifically called for a Daughter, not a son.

After that it was off to the court house where my name was changed to Elizabeth. Yes, I was now named after Ellie. My crash coarse in femininity began for the next few months and before long, here I sat before her. A makeshift Daughter.

"You look wonderful, Elizabeth. I think we'll both be very happy with this arrangement. I'll have the Daughter I've always wanted and you'll never have to work a day in your life."

"I do put a lot of work into looking this..."

"Oh, nonsense, that's not work. You have to do some cardio, squats, and paint your face up to live in the lap of luxury. Don't let any of our gentleman callers know, but it's a simple price to pay."

"Good point, Mother." I attempted to smile but the disdain on my face felt very clear. I knew better than to try and reason with her about the whole not-into-men thing, lest I be taken over her knee again.

"That, my dear, is also something I want to point out. You have what they call 'Resting Bitch Face,' everything you say and do looks it's against your will." No shit.

"I'm sorry, Mother. I'll work on it."

"Nonsense! You're the spoiled brat Daughter of a wealthy socialite, it's only natural you'd be a bit of a bitch. The men will love it. I can't wait to show you off."

"Shall we celebrate with a drink?" Because God damn I need one.

"Sweetheart, I really need you to get smarter and learn your way around a contract if you're going to take up my stilettos and bag your own man."

I stifled a sigh "whatever do you mean?"

"You're not 24 anymore. Mark was 24. You're 18."

"Can you... Can you actually legally change my age?"

"I'm rich, Princess. I can do anything legally. Now, our driver is here and we have shopping to do. He's quite handsome and around your age, I think I'll keep him around for you."

I didn't have any words. I could only smile and nod, though it was a bit of a relief to let my "resting bitch face" do it's thing. I followed my new Mother outside. A tall, muscular guy in a suit waited by the car, he couldn't have been older than 20. But he was dressed very nicely, and opened the door of the limo for us. He kissed my hand before I got in.

"You know, I've had the most wonderful idea!" Ellie chimed in, addressing the driver. "We're going to be shopping today, lots of outfits, lots of shoes, lots of jewelery. You know, girly girl things. But what's say you help sweet little Elizabeth out and let her model some for you, help her see what a real man would appreciate?"

"Whatever you need, ma'am. It would be my pleasure." He said before stealing a glance at my legs then making eye contact, I met his gaze with my plastered-on glare, he responded by smiling and licking his lips before closing the door. I got chills up my spine, is this how men were going to look at me? What does Ellie expect me to do with this guy? Why was she so right about men liking the resting bitch face? My reluctance being a turn-on to these guys was going to make things much harder... I didn't mean like that.

"Don't worry, dear. I'm not going to make you marry a driver. He's just someone we can keep close, get you some practice to reel in a real big fish. So, anything you were imagining these gold digging little bimbos doing to you once you had my Husband's money, make sure you let him help you get the hang of." 

Can't Stop Smiling

 

Charmed

 

A Letter Home

 

 Dear Auntie, Here's a photo of me on the set of my very own movie. It's been a long time coming, especially since the whole cultural reset occurred I thought it would be difficult for me to find a role, especially a leading role as a guy in a dress after getting my theater degree, but you believed in me. My siblings always talked about how out of touch and loopy you are, but when they disowned me for not being deemed essential or manly enough to avoid the new mandates, you took me in helped me become my new self, and bought me a ticket. You even helped me decide my new name when I got here, no longer Corey, I'm Destiny!

It was difficult at first, not having your guiding hand or your safe house I have a place of my own, well I share it with a few other gurls in the same boat as me but, not to brag, I'm definitely the most successful one of us. I had a guest spot on a sitcom where I went on a date with Damon Wayans, Jr. and I got to play a real girl! And Damon was super nice!

But now I'm starring in my own movie, with talks of a sequel! That's my co-star after we had a quick rehearsal, which reminds me I need to reapply my lip gloss after this letter. The movie is a slice of life story about a bouncer taking a rambunctious club girl backstage and well.. I think the subject matter is a little inappropriate, so I won't share a name, I know you love to support me and I appreciate it. But it pays decently and seems like a steady role, plus it lines up with my interests. Anyway, thank you again for everything you've done. A check reimbursing you for the plane ticket is in the envelope.

I'm needed on set. just wanted to catch up my favorite family member. I have so many new outfits, every time I buy one I think about being that nervous guy confused about his body and the world around him changing, and you'd always talk me into modeling your old clothes until I got some of my own. Totes in need of a visit and another fashion show once we're wrapped!

Hope all is well and please write back! -Destiny

P.S. If my parents ask please tell them I'm still waiting tables. It's just... Easier that way.

Repost - Improved

 

Repost - Closet

 

Repost - Day Drinking

 

Repost - Awaited Touch

 

Repost - Everyone Needs A Hobby

 

Repost - Punishment or Training

 

Repost - Misunderstanding

 

Repost - Happy to Help

 

Repost - Birthday Visit

 

Repost - Christmas Card

 

Repost - Anna

 

Repost - You Do For Family

 

Repost - Auntie's Fashion Victim