Lost in the City

 

Embrace Tradition

 Wayne, now begrudgingly answering to

Whitney was led by her Stepmother

Grace, to the hallway mirror, practically

trembling out of her high heels and

nervous to see the feminine creation that

had been made of Wayne's greasy

unkempt curls. Grace couldn't help but

2notice the split second when Wayne didn't

recognize Whitney in the mirror, fell head

over heels for this mysterious young lady,

then the disbelief as that fragile front of

masculinity crumbling and falling into a

sea of submission. A boy broken and a

girl ready to emerge.

Whitney hadn't been able to look in the

mirror through the waxing, the tweezing,

and the beautifying, though she would be

on the fast-track to learning to do it all

herself soon. She'd been in the heels all

day, along with the waste cincher, the

false breasts, and the lingerie, stockings,

dress, and pearl necklace while preparing

dinner. Grace sat Whitney down to do her

hair after she put the roast in the oven.

Grace gave the girl a moment to take it all

in before reminding her it was time to set

4 places at the table. Whitney's head

swung around, her pearls clacking

together, her big bouncy hair framing her

cute, pouting face. Her first instinct was

to ask if her Dad came back, Grace shook

her head and informed her that he was

still long gone, and that Whitney would be

treating the housekeeper, Catalina, and

her son, Carlos, to dinner as an apology

for Wayne's behavior.

Wayne had inherited his Father's habit of

looking down on women, minorities,

people of lower social status, but he

lacked his Father's charisma and charm

Spending his days since graduating high

school, minimizing multiple blank college

applications on his computer to jump

onto forums and spout incel nonsense

and take out his frustrations on the

women in his life. Especially since his

Father packed up and left.

His Father shared all of Wayne's views on

women staying in the kitchen, being seen

not heard, and deferring to her man. But

he kept this all quiet until Grace brought

of Wayne's attitude, so when faced with

an ultimatum, knowing Wayne was an

adult now he dropped everything and

found another wealthy single woman to

shack up with good riddance Grace

thought. But even as Whitney, she held

out hope that he would save her. Poor girl.

Under threat of being kicked out and cut

off, this scrawny, anxious "man's man"

folded faster than Superman on laundry

day. Doing chores around the house,

showing manners, avoiding the websites

where he spewed his ignorance, Grace

appreciated Wayne's efforts and set him.

up with Sadie, the daughter of one of her

friends, this unfortunately fell on the

same day that Catalina brought Carlos to

do some landscaping work, the young

woman was much more taken by the kind,

hard-working young man over the

stubborn one that kept asking her to join

him upstairs with all the subtlety of an

After School Special.

When Wayne felt jealous, he exploded and

called Carlos every unkind name in the

book, called Sadie a tease in so many

words, told Catalina to mind her business

and keep to her chores, and told Grace

that she was too lazy to even do a

woman's work and hired Catalina to do

them. Grace took Wayne over her knee

and spanked him in front of everyone and

told him things were gonna change.

Wayne sobbed in his room as Carlos and

Sadie got to know each other and Grace

detailed her plans for Whitney to Catalina

and she was overjoyed. The

brainstorming session involved Whitney

wearing a french maid costume and

accompanying Catalina to the other

homes where she works and learning how

a woman keeps house, but one thing at a

time.

"Oh" Whitney squeaked in the girly voice.

And put in an inhuman effort to force her

pout into a smile "wonderful!" as she set

the table for their guests. Grace followed

and corrected her as she tried to set the

table.

"Make sure you make a good impression

on Carlos tonight, otherwise the rest of

the evening will be quite awkward if you

give your gentleman guest a poor

evening."

"Yes, Mother." Whitney whimpered, not

wanting anymore information.

"By the way you'll have to make sure to

send Sadie a thank you for lending out her

boyfriend tonight so you can see how a

gentleman is supposed to treat a lady"

Whitney tried to speak but her voice was

uneasy. "Oh, don't worry dear, it's just a

first date, a lady doesn't have to do

anything on a first date, despite what your

bad influence online friends tell you." She

informed her that after dinner Carlos

would take her to the carnival and she

was to be a demure lady the whole time.

Whitney nodded.

"Ok, Mother."

"And he's excited to finally be able to have

his own vehicle. I gifted him your old

rustbucket, he complimented your taste in

stereo." Whitney threw her hands into the

air. "Calm down, Whitney, I remember all

of Wayne's comments about women

drivers, since you're a girl now, we

wouldn't want you to get into an accident.

Carlos actually thanked me more in the

first 10 minutes after I handed him the

keys than Wayne ever did in all the years I

knew him. But don't worry he and Sadie

have both offered to give you rides to

salon appointments or to go shopping, or

all of the gender affirmation

appointments you'll have coming up as

long as you ask nicely and behave

yourself. And you'll have a chance to ear

a bit of your own money since Catalina

said she'd be happy to take you on as her

assistant so you can learn more about a

woman's place in the world. I think you'll

make THE most adorable maid."

This was it. Whitney's breaking point,

there was no way she could push her into

going on a date with that meathead jerk

Carlos, be a gal pal to that teasing bitch

Sadie, take orders from Catalina, and no

way she would be Grace's Daughter. She

stomped forward, prepared to go on

another rant, then remembered the

spanking, her lip began to tremble, the

tears welled up in her eyes "I... Thank you,

Mother"

"Good girl. Now go to the powder room,

calm yourself, and touch up your make-up

before our guests arrive. That's what we

ladies call freshening up" Grace teased

with a wink.

Black Wedding (Halloween)

 Ok, this one is really different from my usual work and it's pretty dark I think but it was a lot of fun to make and I hope it's fun to read. Ignore the Wednesday red carpet premiere background please. 

Eddie Cruz was something of a cautionary

tale in the neighborhood, an urban legend

that some weren't sure even existed at all.

The community was quite straight-edge

and religious, the town didn't even have a

liquor store. So a horror story about a kid

who listened to sinful music, skipped

church, snuck out, did drugs, and

supposedly dabbled in the dark arts was

something parents clung to and the

neighborhood kids embellished. Some

say Eddie blew up in a meth lab, some say

that he was one town over strung out on

drugs, some say he joined a cult and ate

ravens under the overpass. But one

scenario nobody considered: He

summoned a demon to Earth and was

forced to become its bride.

While that turn of events seemed

farfetched, seeing Eddie return to the

town on the morning of October 31st with

long hair, a soft, beautiful, made-up face

with plump kissable lips that drew the

eyes of all the repressed young men who

passed the gorgeous young woman

before knowing the story, the truth would

soon come to light. The Black veil and

wedding dress would soon signal the

coming of the demon Eddie, rather

Valentina as the demon so affectionately

renamed her, was now shackled to forever

more.

She started her day walking the street, her

black heels echoing unnaturally loudly,

turning heads and handing out invitations

on black matte paper with blood red print.

There would be a wedding between she

and her new master in the town square at

nightfall. This prompted a response from

the local police, as well as Valentina's

parents, who all met up at the police

station, their extreme' religious beliefs

prompting them to take this unbelievable

story deadly serious.

When questioned as to why they would

believe this demon's servant was really

Eddie, she spoke in her high-pitched,

nearly unrecognizable voice to describe

intimate details that both of her parents

recognized as memories they'd made

with Eddie. When asked how they were

supposed to believe how this beautiful

young woman was Eddie, who always

looked a bit rough for wear, she asked

that her parents leave the room, after they

did, she stood and lowered her black lace

panties and raised the dress, revealing a

severely shrunken pair of testicles sitting

snugly below a locked black chastity cage

that let off an orange glow as if

enchanted by hellfire. She pulled her

panties back up and returned to her Seay

as her parents re-entered and the cops

assured them this was their boy. Was

Detailing what happened, Eddie had felt

shunned by the town and fell in with

individuals who practiced the black arts,

unaware that their plan was to offer him

as a sacrifice to a demon in order to gain

powers from them the previous

Halloween. However, when he was

summoned, he laid claim to his sacrifice,

causing the enchanted to lock away any

ties to his previous manhood. Eddie then

watched as those who betrayed him were..

denied a wish and were dragged kicking

and screaming to Hell.

Eddie was christened Valentina and the

enchanted chastity cage projected its

influence upon her, slowly morphing her

face and body to that of the demon's

desire. Making her more submissive,

loyal, and attracted to her captor, often

haunted by dreams of the eventual

consummation of their unhold union on

the night of the following Halloween.

Wearing anything but the lingerie,

dresses, and heels chosen by her master

brought immense pain, attempting to

escape or get help would make her body

cease to walk, take away her voice until

she gave up on each futile attempt,

except for this day, a wedding gift from

her soon-to-be demonic husband. She

was allowed to return home and speak

freely to her family until nightfall, when

would be claimed, táken, and

supernaturally impregnated while living

eternally in the demon's realm. But she

needs two things: Her Father to give her

away and the town to be in attendance.

They refused but Valentina insisted that

this was the only way to keep him from

leveling the town. If they followed the

instructions, the town would be spared.

So that night, the entire town gathered.

Frightened and disgusted at the sight

before them. The petite and beautiful

woman in the revealing dress that was

once the hoody-clad teenager that

inspired his neighbors to lock their car

doors when he skated by, being walked

down the aisle in towering heels by her

Father to an 8 foot tall demon standing

nude, his cock swinging past his knees.

Crimson skin and rippling muscles that

look as if they were' carved in granite.

Slicked hair, a large beard, and a

victorious grin upon his face as he looked

out to the crowd before him. They had to

watch as he stood proudly, his victim

standing barely a foot away, practically

eye level with his endowment. The local

pástor between the two, declaring their

marriage. As he leaned down and their

lips met, a Hellish portal opened behind

them.

Every young man in the crowd shouted in

pain and terror as they clutched at the

laps of their pants. They then fell silent as

they stood, marching single-file as if by

ce into the portal. Valentin looked out

over the crowd left behind, her eyes

turning an inky black. "Your harem, my

King.'

He chuckled, and put his strong arm

around his bride and used his strong,

clawed hand to pull her close as a sinister

smile grew across her face, she had

gotten back at the town that shunned her,

having taken all of the sons they

unfavorably compared him to. Her

husband replied, "Your servants, my

Queen."

Hooked

Hey, everyone. Things have been pretty tough lately, sorry that I've been gone. My confidence and creativity has been shot, but I've been sitting on this caption for a little bit and thought I'd share it and let everyone know I'm ok. I plan to have a few new ones ready to go for Halloween because I don't want to let everyone down, I do enough of that in the real world. Please enjoy, I love and miss you all. Hopefully I'll be back to normal soon. 
 

 This was inspired by the "In This World, I'm Elise" story by Surgcat on Literotica that I was super into but unfortunately like "School Policy" that I did a few caps inspired by, both the story and the author have disappeared from their respective sites. Both are stories I was very excited to see continue, so hopefully they turn back up some day. 

EDIT: oops. Last word in the third paragraph is supposed to be Alpha, not outlaw. I'm a ditz.

Charitable Act (Request)

 

This was a request for Vanny. She makes wonderful captions and her blog is in the sidebar, so make sure you check it out and tell her Sydney sent ya. 😉 

Repost - Lessons in Workplace Interaction

 

Hi all, this is the last caption to repost. Can't believe it started more than a year and a half ago :-)
Hope you enjoyed them as much as i do ;-)

A huge thanks to my bestie Sydney for trusting me in this process, can't wait to see the new captions you'll make <3

Repost - House Arrest

 

NEW - 63 Jump Street (REQUEST)

 

Had a request for this GIF and a group of mean girls making a new girl full of hormones throw a little fit. 

Repost - Broken

 

Repost - Impending Frills

 

NEW - Wiggling Out

 

Repost - Trump Card

 

Repost - Can Ms. Sydney spoil you a little

 

Repost - Awaited Touch

 

Repost - Lemonade

 

Repost - A Lady But Not Ladylike

 

Repost - I Miss My T-Shirt

 

Repost - Princess Pinkness

 

Repost - Resigned

 

Repost - Some Things Never Change