A New Younger Sister

 

Captisa County Pageant: Cry for 5

 CryoFly won the pageant.

Captisa County Pageant: Boyfriend Punishment

 

Captisa County Pageant: New Sister Swimsuit

 

Captisa County Pageant: Perspectives

 

Captisa County Pageant: Sissy Stepson

 

My stepson is learning that he must take the pageant seriously if he has any chance of being turned back into a boy. He is such a disappointment and embarrassment to the family. My daughter is attending an Ivy League college on scholarship, won numerous community awards, and won many beauty pageants growing up. Meanwhile, all my stepson seems to do is ditch school, vape, play video games or skateboard with his friends, and leave a mess around the house! While his father is away on an overseas business trip, I’m improving his life whether he likes it or not. He was humiliated when I took him to the salon instead of to a skate shop like I promised and announced to the ladies there that he was going to have a MAJOR makeover performed. It took hours for the waxing, hair extensions, nails, teeth, and skin care but he came out looking a like a little sissy by the end of it. A special chastity was placed on his boy part to make it look like something a girl would have down there forcing him to sit down when urinating and unable to get hard at any time.

After leaving the salon, I referred to him as “Sophia” and treated him just like my biological daughter. He would need to be fitted for a bra, get some panties, start wearing girl clothes, makeup, jewelry, and many accessories to soften him. I made him text his friends a selfie of himself wearing lipgloss and making kissie faces to announce his intention to enter the Miss Captisa County pageant. A friend of mine on Facebook recommended he enter after I shared a photo of him getting feminized. She replied that they were having issues finding contestants this year and it would be the perfect opportunity for him to act like a girl and clean up his act.

That was just last week and already Sophia is acting like a princess since I promised he could go back to a boy if he at least gets first runner-up in the pageant. If not, I need to consult a doctor for some surgical options. Dress shopping is today and our little sissy, Sophia, is going to try on many different dresses, but seems to already know what she wants.

Captisa County Pageant: All the Way

 

Captisa County Pageant: Dare Bro (gif cap)

This pageant is becoming serious! These gifs are a pain in the uterus, but a lot of fun. Higher quality version on Patreon.

Captisa County Pageant: Brother Caught

 Just be honest with your sister.

Captisa County Pageant: Truck to Tiara

 

My son, Justin, was disappointed when it was announced that the mud bog at the county fair was canceled this year. He had spent weeks modifying his truck for the event and was always into masculine hobbies being a boy’s boy. To cure his depression, I advised him to find another activity. Justin complained that he had no interest in livestock or growing the county’s largest watermelon so just wouldn’t attend at all this year and would just stay at home playing video games. It hurt to see my son act like this and just throw away all social activity since the one event he wanted at the fair wasn’t going to occur this year. But there was another event that was may get canceled this year. Heard from the girls at the salon that the beauty pageant was to be canceled due to lack of participation which were they were obviously unhappy about due to lost revenue, but that one of the girls had said there were a number of boys who had appointments coming up and would be made over as proper young ladies!

You should have seen the look on Justin’s face when it came home to find his presents on his bed. There was a pageant dress, nail polish, bra and panties, a gift card to Starbucks, leggings, wig, makeup supplies, hair brushes, rings, cute PJs, a pink sweater, heart necklace, teddy bear, princess perfume, set of Intuition razors, and heels. He was confused at first, but I smiled and assured him that he would be in better spirits and have a blast being one of the girls in the Miss Captisa County pageant! He threw a fit about it, but calmed down a little when I said I would buy him some truck supplies if he got through the pageant. It would just mean a few weeks of learning how to act like a lady, talking like a girl, and being the prettiest he could pull off. Once he started shaving his legs and using the perfume, I noticed a few changes in his personality. He seemed a little softer, wanted to open up to me about more topics, and even watched a few chick flicks with me at night. He was now going by the name Julia for the pageant and couldn’t wait for the talent portion where he would do a comedy routine inspired by Amy Schumer. We made an appointment for him at the same salon I went to where he would turn into a long-haired blonde beauty.

By the looks of how much he progressed, I’m having a motherly instinct that the truck parts I promised him will soon be replaced by the gift of new feminine decor for HER room, thousands of dollars in makeup supplies, and a new pink Jetta.

Captisa County Pageant: Ex-Boyfriend

 My boyfriend, William, has been on thin ice for a while, but after I found out he cheated on me with some sorority girl he’s done for sure! I was looking forward to the weekend with him since things were getting serious. The plan was for him to go back home with me for the weekend since the county fair was going on and he could meet my parents. What was going to be an amazing time connecting turned into me wanting him to not exist anymore! I didn’t even tell him that I found out. The plan came about from advice on a forum and talked to my parents who were suffering from empty nest syndrome. My cousin Courtney told me the pageant for fair queen may not happen this year and I told her to not worry, since there would be at least someone entering.

Right when we arrived at my parents house, we settled in and I took him in town to do something fun. Had to lie to William about it being an escape room and he was wondering why we were entering the room separately. Upon entering the room, he was tied to a chair and subjected to a video coming from a projector that put him under deep hypnosis. The lady on the screen brainwashed William into thinking he was my younger sister. He would now go by the name Mallory and think he was still in HS! She made him forget about his life at college with his frat bros and ditch all the masculine hobbies he once had. Mallory would now think of HERSELF as a girly girl cheerleader who loved fashion, making custom jewelry, and doing funny dances on her TikTok. She would looking forward to the county fair this weekend with dreams of being crowned!

Once we arrived back home, our parents welcomed their new daughter. She took my old room which she commented about redecorating a little once the pageant was over. Although she still looked like a college boy, in the mirror she only saw herself as a young, blonde girl. I slept in another bedroom knowing we had our work cut out for us the next day, but would be pleased with the results of my ex-boyfriend being punished for what he did.

In the morning, we arrived at the salon to make miracles occur. They started with a full body wax followed by doing some skincare on her face to take a few years off and make her look much more feminine. Her pen*s and balls were tucked in a special way that would make the swimsuit competition believable, but also allow her to go potty when she needed. It took a while to put her blonde hair extensions in, get her eyebrows waxed, breast forms glued on, and get a mani-pedi but it was all worth it to see my new little sister look perfect for the pageant. My parents stated that once she became settled at school and into her new role in the family, they would explore surgical options to make those breasts real and get rid of that thing between her legs as punishment for breaking my heart.

The hypnosis was going to be permanent and I could tell my lil sis was acting more femme than any other girl on stage! She was graceful in an evening gown, perky in a swimsuit, delivered an amazing vocal performance of an early Taylor Swift song, and answered the question perfectly. She was meant to be Miss Captisa County and I can’t wait to find out how she does in her new life as a popular girl at school and distinguishable young lady representative of our county!

Captisa County Pageant: Intro

 

Joke Homecoming Queen

I made this cap by request for someone who didn't like it and didn't even thank me. Hopefully someone else will like it.

SPOILER: Totally into stories where crossdressing leads to a magical change... Best of both worlds!

AND TG LAND NEEDS MORE HOMECOMING CAPS!

Not Your Date

 I love the setup for this. Though, I wonder if any boy has REALLY been forced to go to prom as a girl in real life.

Prom Deux

 

Made for Vanessa at https://vanillathunderstgcaps.blogspot.com/

Cap-a-Thon September

 First day off in about a month! Capping all night. Post your ONE SENTENCE ideas here.

GGW Back in Time

 

Based on an idea for a novel. Does this cap look like it's from 2003 or not?!

The Summer Concert

 Living the life! Shaving your legs, getting hair extensions, picking out a cute dress, and going to a Country Music Concert!

21 Dreamz

I made a few caps about second chances. This story concept has been on my mind for a few months. Maybe it needs to be a full story!

Vance's Job at Hooters

I just made a few financial caps that are on Patreon. I've always loved stories of feminization where money is the motive! Made this for Vanessa at  https://vanillathunderstgcaps.blogspot.com/ who recently posted a story about Hooters on TGStoryTime: https://www.tgstorytime.com/viewstory.php?sid=6803

Sh*t Courtney Found (July 2022)

 SCF was a short-lived feature I had on my blog a while back. It was a listing of random gender change stuff I found throughout the week. Going to start bringing this back!

 

Kitty St. Claire sent me this poem. At first, I thought it was something vintage but then discovered it was featured in the New Yorker and is about to be released by the author in a book of poems!

I've listed to Malcolm Gladwell's Revisionist History podcast for years. The first episode of the latest season is about "magic wand" experiments that could take place with no issues of ethics, budget, etc. The first experiment is about taking the penises of newborn boys and putting them on newborn girls! Then testing if they grow up as the opposite gender! (The answer may be disappointing to gender transformation fans). The episode is here: https://www.pushkin.fm/podcasts/revisionist-history/the-magic-wand-experiment

Rachel's Haven Gallery section of caps is back online! https://rachelshaven.com/gallery/ Thanks to Miriam for making this happen. This gallery has over 150,000 files, many caps from the early-2000s and dead platforms like Yahoo Groups and Lycos. I thought many of these caps would be lost media, but they are now available again!

More caps coming soon. Summer is a very hectic work load for me in my real-life career and I've been burnt out.

Love,

Courtney

Blogger Death

Yet another long-time TG artist has announced that their Blogger page was permanently removed without any warning! Not sure why Blogger is doing this. I feel like TG Land is the only thing keeping it alive right now.  They are obviously not updating this platform anymore.  Just a note, if this blog does ever randomly disappear, it was not my decision! If I ever close the blog, I'll make a post about it. The contents of this blog have been backed up. Although I don't post as often as I used to, I still post to my Deviant Art page and Patreon almost every day.

Love,

Courtney

To Impress the Parents

 This is very sweet. I wonder if it has ever happened for real!

Lying About My Age

I posted this cap on my Patreon back in the fall. It's probably one of my favourite caps from last year. The perfect blend of age regression/progression! There's been a trend lately of birthday caps becoming popular!

Genie App Bad Girl

 

It's Good Boy to Bad Girl week on Patreon!

Sister's Place at Prom

 I almost want to cry thinking about this cap. It's short, sweet, and basically sums up the entire point of this blog! Sweet, clean, gender transformation age regression!

Cap-a-Thon Tonight + 80s Prom Cap (Here you go, Dee!)

In the last post, Dee asked for an 80's prom cap. Good thing I made a bunch of these for Prom season! I love the concept of a guy being sent back in time and turning into a girl in the process.

Busy weekend ahead. Spending about 8 hours capping tonight! Drop your one sentence requests here.

Prom: 2001 (Time Travel/Mom's Place Cap)

More "guy turning into Mom in the past": Check

Somewhat obscure 80s Film reference: Check

Seeing purple eyeshadow again: Check!

It's Prom Week on my Patreon. This year's theme is time travel!

https://www.patreon.com/courtneycaptisa

St. Captisa's

 Who wants to go to St. Captisa's?

Moms Make Mistakes week coming to an end on Patreon! Long cap tomorrow!

Mom's Gym Membership

 

I'm a sucker for before & after pictures in TG caps!

Mom's First Marriage III/VI (Rest on Patreon)

You've heard of March Needs Moms. Now get ready for Moms Make Mistakes! That's the theme this week on Patreon! The first is a 6-part cap series about a college-age guy who discovers that his mother was married to another man before his father which ended in divorce because she cheated on him. He is transformed and thrown back in time to 2002 on her wedding day! Will she make the same mistake twice? https://www.patreon.com/posts/64410885

Note to Scene/Left Me On Read

 Time for 2000s week on Patreon! Thanks to long-time friend Alexis for the band name!

2000s Courtney

 The design had to be like a cap from 2003 as well!

Dee's Renewal

 

Inspired by this post on Dee's Blog: http://deelusionsofgrandeur.blogspot.com/2021/12/tg-caption-logistics-explained.html