#crossdressing tg cap

[vthunder42]

One of my favorite caption artists has returned to the game after a very long absence, I won't say her name, but if you've been seeing my reblogs lately, it's pretty obvious who it is, and that's reminded me of one of her captions from back in the day that I adored and this picture made me want to try my hand at a similar premise.

Text under the cut for the visually impaired:

“Come back to bed, baby!”

“I don’t know what I’m going to do. I mean the makeup washes off, but the highlights? The extensions? And my eyebrows!”

“What are you talking about?”

“I’ve got work in the morning! I can’t show up looking like this!”

“Why not?”

“Because I’m a man! I’m not supposed to...”

“Because you’re not supposed to have long, lustrous hair, shaved legs and delicately arched eyebrows? Honey, I think it’s time to face facts and stop living a lie.”

“What are you talking about? This is just a game, just your fantasy.”

“My fantasy? Maybe that’s what I told you, but don’t think I haven’t seen the looks over the years, looking more at my dress than me, this was always supposed to be your fantasy. The one you were too afraid to admit.”

“But...”

“But nothing. Call out tomorrow and we can discuss this later, right now, I’ve got some more fantasies for us to fulfill...”

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Royal Replacement: (Caption Text Under the Cut)

It was nearly time, the Duke’s son would be here soon and I’d be expected to greet him while our fathers discussed their business dealings. It was hardly the first time I was made to play nice with visiting royalty, but the first time dressed like this. Usually, this was reserved for my twin sister, Penelope, but when her lady-in-waiting went to wake her up this morning, she was gone! She’d been complaining recently about not wanting to marry any of the suitors she had, and had confided in me once that the suitor she desired was actually a Countess, but I never expected her to actually run away from home. This particular Duke’s son was the one my parents favored her to marry, so she needed to meet him. Fortunately for them, even as we get older, our genetics still favor each other enough that I could pass for her if I had to.

And boy, I had to. Even my father was in favor, so my mother and the handmaiden spent the entire morning making me over and stuffing me into one of Penelope’s dresses. My body was smooth and free of hair below my plucked eyebrows, my makeup immaculate and my body accentuated thanks to padding and creatively sewn garments. They even had me attending her harp lesson for authenticity’s sake, it was strange watching my delicately manicured fingers plucking at the strings.

“It’s only temporary!”

“Your sister will return home soon enough, you won’t actually have to marry him!”

But I knew my sister, strong-willed and wickedly intelligent, she’d never be found, but Penelope would become the Duchess anyway, and her brother the prince would vanish into obscurity, never to be heard from again.

[vthunder42]

Saw this image and my brain actually managed to carve out a story for it! Hope you enjoy!

“Hey, you’ve been grabbing water for a long time, Ms. Ernst is getting restless and oh… Oh!” My eyes widened as I saw Chrissy in the arms of one of the ranch hands, passionately kissing him.

“Chuck, can you give us a minute?” Chrissy batted her eyelashes, an effective tool of persuasion, as I knew firsthand.

“Sure thing, babe, but don’t be too long, okay?” Chuck grinned and tipped his hat to me as he walked away.

“What’s going on here? You told me you were into girls! That’s why I let you do all this!” I motioned towards my body.

You see, before arriving at the ranch, I’d been your normal average guy. Yeah, that’s right, guy. Chrissy had been on the welcoming committee, and we’d hit it off on the first night, or at least I thought we did, until she’d confided in me that she liked girls. I thought that was the end of my chances with her until she commented on how she thought I’d make a pretty girl. I’d never been the most masculine, always skinny, with soft features, and I’d do anything to be with her, so I let her make me over into her type, my long-ish hair styled into pigtails, some makeup on my face to plump my lips and define my eyes, a little bit of shaving, (I’d never been that hairy either) and she even went into the ranch’s database to swap my record around so I could room with her and work the hospitality side. It was a wonderful few weeks, even if she kept me at a distance, never doing more than kissing or over the clothes stuff.

“Listen, Tori, you’re cute, don’t get me wrong, but you’re just not my type, and I wanted to let you down easy, but you were so eager, I figured telling you I was gay was easier, but you just wouldn’t take the hint. And given how well you took to the makeup and the dresses, heck, you’re walking in heels better than I am, I think everything worked out for the best. You had fun, didn’t ya? You wouldn’t have liked being out in the sun anyway, right? Why don’t you run along, okay? And bring the water back to Ms. Ernst.”

“O-okay…” I tried to hold back my tears as I grabbed the bucket and headed back to the house.

“Your friend okay?” Chuck asked as he returned.

“She’ll be fine, just lonely I think.”

“I’ve got a buddy who’s been talking about having a thing for her, maybe we can introduce them tonight at dinner?”

“I think that’d be a great idea, baby, now let’s finish what we started!"

[vthunder42]

Exchange Goods For... Services:

I really screwed up this time. If I’d been more careful and hadn’t been such a coward, the RA wouldn’t have found the drugs I was hiding for my friends at the frat house during their surprise inspection. And if the RA hadn’t found the drugs, I wouldn’t have to replace them, and the frat brothers wouldn’t have forced me to go dressed as a girl so they’d have collateral if I messed up again. At least they told me who their plug was, I don’t know if I have enough cash, but hopefully I can at least replace part of it.

“Okay, here’s the stuff, Princess. And you’ve got the money?”

“Of course I’m good for it, let me just grab the cash and… Oh shit…”

“Well, well, well. Looks like you weren’t good for it.”

“Wait! Please! If I don’t bring the stuff to the frat brothers, to replace what got confiscated because of me, then they’re gonna post pictures of me dressed like this everywhere on the internet!”

“I suppose we could come to some kind of alternate arrangement. Usually I’m willing to trade goods with a pretty girl for… services, if you know what I mean.”

“But I’m not really a girl!”

“You’re the next best thing. Now, do you want the stuff or not? That’s what I thought, now let’s get started…”

[vthunder42]

Another Canva caption. Let me know what you think of the new format, any tweaks I need to make? (Text under the cut for the visually impaired)

"Aw man, I thought they'd be bigger... And ugly PJs too..."

"What the hell?! Why did I get transformed too? What did you wish for?"

"I wished to be a smokin' hot chick! Just like I told you I wanted!"

"And you said those exact words?"

"Well... Mostly, it got the gist of it..." "What were your exact words?"

"I wish that when I looked in the mirror, I'd see a smokin' hot chick looking back at me!"

"The same mirror I was looking at when you made the wish?"

"Oh... Well, at least you're hot!"

"I don't wanna be a girl! I wish I was a boy again! Make it change me back!"

"Sorry, can't do that! The planets have to align under your zodiac sign in order for the wish to be granted. Which by my estimation would be about a week before your next birthday!"

"But my birthday was last week!"

[vthunder42]

Made this one a while back, again no resemblance to the Maroon 5 song of the same name, but I figured I'd post it after making Driver's License as a funny bit of pop song similarity.

[vthunder42]

My latest 4 caps from this year so far.

[vthunder42]

Decided to do a one-sided conversation in this one, maybe a bit too expository, but I wanted to try something different. Enjoy!

“Hey! I heard you were back from Vietnam, I’m really glad you’re okay!”

“What do you mean I sound different? Must be a cold or something…”

“Yeah, I know I got lucky. You know my Mom would have freaked out if I got drafted, you remember how my Dad died, and she’s so overprotective…”

“I’ve mostly just been spending time with my Mom, she said if I was going to be around I’d have to help out more around the house, so you know, laundry, vacuuming, the dishes…”

“Your parents are throwing a ‘Welcome Home’ barbeque this weekend? Pool party? Um…. Of course I’ll be there, you’re my best friend, I wouldn’t miss it for the world!”

“Listen, I’d love to talk more, but I’ve gotta go, I’ve got a date tonight and…”

“Yeah, of course I’ll tell you all about the lucky… lady this weekend. Talk to you then.”

“Yes, Mom, I heard you that Steve’s outside! I was on the phone with Bill! Yeah, Bill’s back from Vietnam, do you think we can take my old stuff out of storage yet? They haven’t drafted anyone in months and all my friends are back!”

“I guess it makes sense to wait until the war is over, I guess they could start up the draft again… Oh, so can you take me shopping then? I need a bathing suit for the pool party!”