A Sissy's Rabbit Hole

My latest attempt to stay here on tumblr. Formerly sweetharlot2. If you followed me then, follow me now (please). This blog is gender bending friendly and a safe place for trans, nonbinary, cd and other genderfluid people.

[billiesfemspace]

[kim1girl]

3/25/20- 1486 AL - What neighborhood girl doesn’t want a playdate with Chris? Dress-up is so much fun! And bridal! Some of the girls now realize Aunt Julia will allow weekend night sleepovers as well. Bring a cute baby doll nightie, Chris! Debuted 3/20 on Andy Latex.

[krissiincurls]

Playdates are a delight, especially when the girl coming over is Miss Chris.  kim1girl concurs.

[petticoatedkimmi]

8/21/22

(51)

[kimmipetty]

4/6/24 - Today’s Daily Classic Chris. Oh Chris, you will be dressed like this even when you are completely alone, other than bedtime when you can select one of your soft chiffon nighties.

Debuted 3/20/20 on Andy Latex. Thanks Andy and Christeen. Visit Andy at SMOOTHSLICKNSHINY.BLOGSPOT.COM

(72)

[kimmipettie]

5/16/24

(98)

[kimmicurls]

6/19/26 - Spending time with the girls is a delightful way for Chris to master all the ins and outs of feminized life as a dainty Miss.

Aunt Julia knows what’s best for Chris as she adapts to life in a dress.

(105)

[future-girly-life-posts]

[fairyevermore-deactivated201712]

This is so true.

[femmierandee]

Oh My YES !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!  Very, Very TRUE !!!!!!!!!!!!!!!!!!!!

[kimmipetty]

imbecomingsoooogirly - Jan 2, 2024

I’ve given in….being a girl is so what i am…and loving it…

____________________________________________________________

4/13/24 - It’s an amazing feeling, embracing who you truly are and enjoying everything about being a girl. Feminine immersion is sheer pleasure.

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[kimmipettie]

6/13/24 - I enjoy being a boy but I would squeal and be thrilled if I were a girl!

(5456)

[kimmicurls]

6/19/26 - Deep down, you truly always wanted to give in and embrace the sweet girl living inside. And no longer hide.

You have always ruminated if you were fated for femininity.

(6140)

[keylinc]

Krissi sat quietly, not aware that Mother had requested that Krissi’s permanent be exactly as her stylist’s!

[kimmicurls]

1/22/26

(3)

[kimmicurls]

6/19/26 - It was one thing for Mom to drag me to her salon. But I had no idea that a permanent was in store, even if my feminization had been going on for a few months now.

I gasped when I saw my permed curls! And the looks of sheer delight from Mom and my stylist.

"You're a curly girl now, Krissi!"

Krissi.... who am I kldding? With a name as cute and feminine as this, there's no sense denying that I am now Mom's daughter and a sweet Miss.

Thanks to Keylin for this wonderful Krissi perm captioned pic she created for me!

(7)

[every-alice]

[kimmicurls]

6/20/26 - Your dream came true. She saw the girl inside and no longer wanted you to hide.

(183)

[a-miss-inside]

Kyle– now Candice– sat down next to her best friend, Miranda.  Miranda looked over at her with a smile.

“It’s about time, sister!”

By special request… Hi, @seanpickles !

[a-miss-inside]

It took a few weeks, but soon Candice had to ask…

“Why aren’t my old friends talking to me anymore? Do I have to jump in front of them to get them to notice–”

“Trust me, Candice,” Miranda interrupted, “they’re noticing you.”

[sandybrown121]

Could become an instant Classic. Wonderful!

[krissiincurls]

Wonderful pics accompanying a story of delightful feminine dreams! Candace is on her way.

[k-lee1993]

Wow!  I think I’m going to make this my screen-saver  …once upon a time- Kyle.

[sandybrown121]

Couldn’t picture a better visual image For this series than Candice. I always thought of her as the epitome of sexy, but not slutty, femininity.   To me this fantasy also raises bigger questions, which I have explored in several stories, including  My Son’s Budding Breasts.  The question is, can emotional state / gender identity, actually FOLLOW physiology?  Like in this series, would a boy who always felt like a boy, start feeling more feminine if he started LOOKING more feminine? I have long been fascinated by this question. Of course, one scenario is gynecomastia. In my story, the boy starts out horrified by his budding breasts, and then is fascinated by them, and then is ultimately proud of them.  Aside from gynecomastia, another scenario could simply be a mother feminizing her young son. There’s nothing that says his feelings of femininity have to come FIRST. They could follow. I believe that the simple act of say, putting a boy in a training bra can instantly make him feel more feminine. 

[kimmipettie]

7/23/25 - What a lovely story of Kyle’s transition to Candace. So sweet. I can only hope that Candace thrives in femininity.

This post is enhanced by wonderful comments from the late Sandy Brown and Kaylee (then klees1993).

As you will see, this really resonated with Kaylee, who herself was once a Kyle in her long ago boy life.

(2124)

[kimmicurls]

6/20/26 - How lovely it is to see a once boy like Kyle embrace her femininity. Just like Candace here, Kaylee (Kaylee-girlygurl) was once a boy named Kyle, as she noted above in an earlier account. Kaylee couldn’t be happier now living all girl, as she has since became a cute little preteen Miss.

(2218)

[billiesfemspace]

Lovely!

[kim1girl]

7/7/20- 1558 - Oh, you will be surprised, Chris! You really are hot, girl or boy. A lot of guys will be even more intrigued.  Debuted 7/3 on Andy Latex.

[krissiincurls]

kim1girl Classic Caption #2 - 7/7/21 - Don’t put yourself down. He might be more excited once he learns you were born male and now present female and dress this sexy. (53)

[petticoatedkimmi]

4/27/22

(112)

[petticoatedkimmi]

7/7/22

(127)

[kimmipettie]

8/4/24 - The Daily Classic Chris

Chris never knows what Aunt Julia has in store for her, especially on a weekend. She’s not exactly enamored with all the studs, but both males and females certainly have more than a passing interest.

(155)

[kimmicurls]

6/20/26 - Something must be amiss if you are actually a boy like Chris and are outside dressed like this. Well, perhaps very soon it will be Chris’s fate to be all Miss. We can’t be sure!

(187)

[honoriusbrown]

[kimmipetty]

1/3/24 - You are absolutely thrilled you chose Christmas break to confess to your sibling that you want to be her little sister. She is taking every opportunity available to turn you into the most feminine miss imaginable. Is Mom going to get a shock when you debut!

(261)

[kimmicurls]

1/20/26

(383)

[kimmicurls]

6/20/26 - You can’t believe how Mom reacted. She squealed with delight when she saw the new feminized you. A daughter to be? No, you are already there, embracing your femininity.

(386)

[emmalouisnew]

[sometimesmaddie]

I love wiggling my cute little girly ass while my dress floats gently over my panties and pantyhose 🥰💜🌸👗🌸💜🥰

[kimmipettie]

8/3/25 - Feminine sensations like wiggles and twirls further immerse you into the wonderful world exclusively reserved for girls.

(696)

[kimmicurls]

6/20/26 - Once you are pantied, you can hardly wait until you get to twirl as a girl. Every day is now feminine play.

(796)

[courtneywalsh412]

[kaylee-girlygurl]

I feel sad for those who will never know how wonderful it is to have a mother that supports your feminine journey.

[kimmicurls]

6/21/26 - Mom is thrilled that her once son is now her girl.

Kaylee has had the good fortune to experience the transition from boy to sweet Miss, as her mom insisted.

(184)

[louiselongin]

[buttondowntest1x2run-deactivate]

It’s time

Cute shoes!👠💖

[ppsperv]

🎀💄💋💕❤️Pretty Pink Sissy!❤️💕💋💄🎀!

[kimmipettie]

9/7/25 - Petticoats and party dresses were my dream attire as a boy who wished for time as a sweet little girl. The thought of my petticoats peeking out like this as a pretty Miss was such a delight!

(741)

[kimmicurls]

6/21/26 - Once a boy experiences the delights of being petticoated, she will enjoy the thrill of party dresses with her petticoats on display every single day. And perhaps will become bold enough over time to allow a flash of her pink panties too.

(980)

[felicitycindy]

Playing as girls and having fun. 

Chris and his friend are looking very pretty in their gowns.

Chris - Forced to live life as a girl and now he is taught how to be as feminine as possible.

Another excellent drawings by Christeen

[krissiincurls]

8/25/20- Christeen Play Date- Boys who are “pretties” just love their play dates as sweet young girls. They have only begun to appreciate that their girl life is for good. Yet, what’s not to like about becoming a girl?

[k-lee1993]

I suppose it was good that I didn’t grow up with a close boy friend transitioning to a feminine life like me.  If his Mother was anything like mine, I  can see two competing Mothers playing “Barbie” with their sons as the dolls.  

[petticoatedkimmi]

8/25/22

(153)

[bellesnewmirror]

Chris is so fortunate that Aunt Julia has gone to the trouble of finding another once boy for Chris to play with. Yes, they might commiserate for a time, but they’ll find lots to enjoy about being girls together.

[kimmi1girl]

5/28/23- Both Chris and Alex should realize that not only are they dressed as girls, they are incredibly fortunate and will be living fully female forever.

(165)

[kimmipetty]

8/15/23- When you were once a boy but are becoming a girl like Chris, it’s so nice to find a feminized friend who is just like you.

(175)

[kimmipettie]

5/18/24 - The Daily Classic Chris

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[kimmicurls]

6/21/26 - It’s much easier for a boy undergoing feminization to spend time with someone just like her who is immersed in lingerie and dresses. Chris and Alex will soon come to realize how much they now crave femininity and pretty things. What’s not to like feeling your petticoats swish?

(215)

[metamourmatador]

[kimmipettie]

10/27/25 - It’s incredibly unnerving to be told by a girl that you were born for panties now that you’re this tiny down below.

(741)

[kimmicurls]

6/21/26 - She even said you hardly show. And once she had you in a bikini, she giggled and said, “Good girl! You’re now completely flat!”

(841)

[annasissysub]

[kimmipettie]

12/1/25 - Resist? Seriously? The lacy tiers and bow would compel me to swish.

(152)

[kimmicurls]

6/21/26 - How could you ever resist? You knew by the time you were ten that you were always meant to be a Miss. You know it's high time to go All Girl!

(695)

[natalielikesmen-deactivated2020]

[kellijwill]

Maybe I’m just the only one, but I think a lot of boys might find an alternate lifestyle if they found the right dress in their sister’s closet.

[masquerading-male]

Quite true.

[kaylee-girlygurl]

I should have mixed feelings about this, but I don’t. My life bloomed as a child when I began wearing my sister’s dress …and soon followed by panties, bras and other fascinating fem-wear. The makers of girly fashions should include a warning label against boys and men wearing these clothes which often leads to addiction. If it’s an addiction that I got, I wouldn’t change it for the world!

[beninpinkpanties]

I also have mixed feelings, but the statement is true

[kimmipettie]

8/6/25 - A boy’s first dress may lead to a lifetime of trying on all the others in the closet. The same goes for his first nightie. Why would you ever revert to pjs once you have experienced the delights of chiffon?

Kaylee speaks from experience, having gotten the opportunity to grow up as a girl.

(256)

[kimmicurls]

6/22/26 - Panties feel so soft and good. It’s alright to crave the delights of femininity. You were meant to be a girl. That’s understood.

(445)

[kim1girl]

9/25/19- CJ Photo Session- Chris is continually reminded that he is now a lovely girl, even as he remains a male. Who would ever think twice seeing portraits of the sweet girl in dresses with cascading curls? There’s little boy left inside. Thanks to Carole Jean and Christeen. Visit Carole Jean - www.petticoatpunishmentart.com

[krissiincurls]

Classic kim1girl #1 for 1/31.  Chris is such a lovely miss!  Thanks to dressupforboys for re-blogging this along the way. (59)

[kimmipettie]

5/30/24 - The Daily Classic Chris

(109)

[kimmicurls]

6/22/26 - Despite the protests, Chris can’t help seeing herself as the lovely girl she has evolved into. The camera lens doesn’t lie. Just embrace your femininity as a pretty Miss, Chris!

(125)

[keylinc]

Kimmi finished getting ready!

[kimmicurls]

6/22/26 - Mom always insists that an adorable hair ribbon finishes off the full transition of a once boy like Kimmi into a sweet Miss.

(2)