Happy International Fairy Day!

International Fairy Day in 2025 will be on June 24th, which falls on a Tuesday. This day celebrates the mythical creatures known as fairies, found in folklore and popular culture. I love being a sissy fairy!

From my new book "Letters from the Fairies"

The term "sissy fairy" typically refers to a male-to-female (transgender) individual, often a cross-dresser, who enjoys dressing as a fairy, particularly in a feminine and playful way. It can also refer to a fictional character, like in the book "Sissy White and The Seven Dwarfs," where a male character is forced into a feminine fairy tale role. The term combines the concept of a "sissy," often associated with effeminate men, and a "fairy," commonly depicted as a whimsical and delicate creature. 

In this context, "sissy" is used to describe someone who embraces traditionally feminine traits or behaviors, often in a playful or self-aware manner. It's important to note that this usage is distinct from the term's historical usage to denote weakness or cowardice.

Love, Sissy Fairy Annie

Favorite Pink Party Dressess

These are Sissy Annie's favorite pink party dresses! Dresses like these are mostly worn by little girls of approximately ages 4 to 6. The dresses are about 6+ inches above the knees. Little girls that age wear shorter dresses.

On the left is a quilted satin dress with delicate lace on the hem and on the puffed sleeves. 

The dress on the right is a cotton pinafore with pretty lace and cute pink bows.

During warmer weather sissy shows her lovely, smooth bare legs with only frilly ankle socks. In colder weather sissy wears pink tights with the ankle socks over the tights. 

Black patent leather shoes, with pretty bows, are worn for most formal occasions like girlfriend's birthday parties and holidays! She also has pretty pink footwear!

Sissy also wears pretty pink sissy panties with bows and ruffles. Sissy is usually caged and locked. One more thin petticoat is worn under the dress to give it a little more pouf and volume. This provides a cuter look as sissy performs a proper curtsy for everyone she meets.

Both dresses have back zippers which require assistance from mommy. Just to be clear, mommy bathes, dresses, etc and gets sissy completely dressed and madeup.

When sissy is wearing a PINK outfit she will always be a perfect prissy pink little pansy.   A darling little sissy who never wants to be anything else!

Soft warm pinks are soothing and smooth, particularly synced to the energy of babies and young children. Pink is often associated with emotions like tenderness and joy.  Pink generally represents femininity, gentleness, sweetness, and other nurturing qualities.

Sissy Annie is triggered by hearing the word PINK and seeing the color "PINK" 

When mommy or nanny speak the word "PINK" sissy becomes super-obedient and girly, extraordinarily sissy-ish and very juvenile. Very similar to what one would see in the behavior of a 4 year old little girl!

When sissy is out in public and sees someone wearing pink she will curtsy and say "I love your pretty PINK dress! I am a prissy PINK little pansy." That is quite the conversation starter.

Top Row - quilted satin dress with delicate lace on the hem and on the puffed sleeves. 

Bottom Row - a cotton pinafore with pretty lace and cute pink bows.

Photos taken at Simply Corey Photography

Baby Sitting sissy baby annie

It was only a few days after the school year ended for me that I received a text from Ms. Emily asking if I could babysit and spend some time with Prissy Pink, Little Pansy Annie.  I was more than happy to honor her request and it had been a while since I had seen  Sissy  Annie.  

On the appointed day, I arrived at Ms Emily's house to babysit  Annie. She opened the door, and as I entered the front foyer, I could hear  Annie running to greet me.  She gave me a big hug and then stood back, curtsying to me.  I  hugged her back and kissed her forehead.  

She was wearing her yellow bear sissy dress with a matching yellow bow in her golden hair. Additionally, she wore little soft shoes with matching yellow lace socks.  Ms. Emily walked into the kitchen and pointed out the fruit on the counter for a snack. She also mentioned that there were two bottles in the fridge: one of baby formula and the other of juice for her to drink later. Additionally, she said she could have simple macaroni and cheese for lunch.  

After Ms Emily left, I asked Annie what she would like to do. She did not have an answer.  So I suggested that we read to her dolls along with dolly Aurora, whom I brought with me, so that she could be with Annie's dolls.

So we arranged my doll Aurora. Annie's dollies. Blaire Wilson, Katie Ribbons, Nenea Mitchell, and  Kanani Akina on the floor along with  Sissy Annie.  I sat on a bench and began to read to them a book Anine picked out called "The Princess and the Pirate".  They all sat there and intently listened to me as  I read aloud, and  Annie giggled loudly as I  tried to do deep voices for the older male characters in the book.   

After  I read to them,  I suggested that we go outside and play with the soap bubbles I had brought.   Once outside, Annie was jumping up and revealing her diaper cover as she tried to catch the soap bubbles as they floated in the air around her.  She thoroughly enjoyed that part of our day.

Once   MIs Emily returned home  Annie was laying in her playpen and sleeping as an angel holding  Blair Wilson tightly and sucking her pink pacci.  .  Ms. Emily asked how the day went, and I told her what we had done.  I smiled and told her I might have worn Sissy Annie out.  She smiled and thanked me for the help, and said she will be needing me a lot more this summer to help her.  I look forward to sitting with Anied again, maybe next time we will do sidewalk chalk drawings.  

Sissy Claire

Do you like my pretty baby dress and my cute bear plushie? I love being an infant tile little baby. I love sissy Claire!

The Swan Princess #1

 

The Swan Princess

When Princess Odette is transformed into a swan by an evil sorcerer's spell and held captive at an enchanted lake, she befriends Jean-Bon the frog, Speed the turtle and puffin the bird. Despite their struggle to keep the princess safe, these good-natured creatures can do nothing about the sorcerer's spell, which can only be broken by a vow of everlasting-love.

I love the first movie! Wonderful movie!!!! Outstanding animation and an incredible story. I know adults won't love the movie. Mostly it's for little girls like me who love princesses, unicorns, fairies and magical tales. I know it's a lot like Disney movies but that's ok. I love Princess Odette too and the lovely songs she sings.

I love having magical adventures! Pretending to be a pretty fairy princess! Giggle. Mommy says that I AM a prissy pink little pansy fairy.

The Swan Princess 12-Movie Limited Edition Gift Set (DVD)

Mommy gave me a big surprise today!!

Celebrate 30 enchanting years of the magical, musical world of The Swan Princess! Enjoy all 12 amazing animated features, each filled with timeless songs and captivating adventures in one must-own complete DVD collection! This once-in-a-lifetime limited-edition set includes a gorgeous Swan Princess music box- a keepsake for every collector who is eternally young at heart.

A beautiful princess falls in love with a prince from another land, but an exiled magician who wants her for himself conjures up a spell to transform her into a swan. Forced to embark on a dangerous quest to reverse the magic, the princess is helped along by some new-found animal friends.

It's a beautiful story for little girls ages 3 to 7! I can't wait to start watching it ---

Sissy Princess Annie will post about each movie on her blog!

Loving dresses! Annie's regression to age 4.

A dialogue with Mistress Chris:

Annie: I just adore wearing dresses because they make me feel so pretty and girly. I do love the feeling of a beautiful dress with lots of petticoats as I walk and move. I can feel my hips swishing as I take small mincing steps.

Wearing a dress also takes lots of care. When sitting I must keep my knees locked so as not to show my panties. I also have to be so careful when it is windy outside. A strong gust of wind blows up my skirt and shows everyone my panties. I get punished for that.

I have been taught to curtsy and introduce myself to everyone I meet in order to display what a darling sissy princess I am. I must be in a dress to do a perfect curtsy. Mommy told me ONLY sissies and little girls curtsy anymore.

I always feel weak, helpless, very vulnerable in a dress.  Mommy says that is very natural for a little girl sissy. Especially for a fairy like me who loves to be ultra femme and sissy! 

I am a prissy pink little pansy!

Mistress Chris: I certainly agree 100% that sissies certainly should never be allowed to wear pants. I love the way your mommy takes care of you and ensures you always act as a proper sissy should. While I understand that you may not like being spanked it is required. You are a child!

Unfortunately you were born male and no matter how good of a sissy you become your male brain will still mess up. Being punished is a reward that your mommy gives you so that you learn from your male mistakes. Every smack, whether it is from mommy's hand or paddle, is a reminder that mommy loves her sissy. You need to thank her with a proper curtsy after taking her precious time to correct your behavior. 

Annie: Mommy's approval is everything to me. I always think about how I can please mommy. I am truly upset and distressed when I have done something that displeases mommy. I just break down and cry because there is nothing else I can do.

Mistress Chris: You need to understand that mommy is teaching you to be an obedient little sissy and always do as she expects of you. Only sissies and bratty boys, under strict petticoating, are the only ones who curtsy now. Learning to curtsy and sit properly in your frilly dresses is a must. You are such a lucky sissy that mommy takes the time to teach you these things.

Annie: Thank you Mistress. Mommy is very strict about my punishments. She says that immediate negative reinforcement (her words) is necessary for sissies because we are basically children. The other day we were walking together in a mall and I got ahead of her. That is not allowed. She took her smaller paddle out of her purse, found the nearest bench and put me over her lap. I was not allowed to scream so she put a pacifier in my mouth.

Mistress Chris: Back to the topic of sissies wearing dresses! I am not surprised pink party dresses are your favorite. I love your pictures especially the ones with your holding your dollies. 

Yes, the pants question is an interesting one. Not surprised you hated wearing pants again or the threat of acting like a boy. I have help guide mothers using petticoating for more than 20 years and find it interesting that even the most resistant brats learn to love their dresses and fear being put back into pants.

IMHO males are naturally very feminine and are taught to fear their femininity. Frilly dresses bring out this natural feminine personality. An extended period of time wearing dresses ensures that a male fully embraces his femininity which triggers their brain to reject all things masculine especially wearing pants.

Annie: Mommy gave me these three goals:

• To be a dainty and delicate little girl sissy in the way I think, act and present myself
• To completely accept female control and never question wha I am told to do
• Proud to show everyone what a precious little girl and pretty princess I am.

I love my frilly dresses so much! Every morning mommy bathes me, does my hair and makeup and dresses me. Always in a pretty frilly cute dress! Then I stand in frond of the full length mirror and do 5 very deep girly curtsies! I tell mommy I love her and give her a hug and kiss! I love being a prissy pink little pansy! Then I go off to take care of my "little darlings". I mean my dollies!

Mistress Chris:  As you know, a boy who wants to be totally sissified must have a collection of dolls, his girls, with whom he plays with every day. Mommy knows when "his" becomes "hers" and "he" becomes "she". Every sissy dreams of that moment of being called a "Girl".

This is one of my favorite photos of you. A pretty pink frilly dress! A lovely bow in your hair and your dolly, whom you care for and love, in your arms. You are full of girly sweetness!

Mistress Emily

Femboy Charley

1n our travels to recruit sissies for FISH ACADEMY FOR SISSIES we met Femboy Charlie. He was wearing this darling dress and displayed many feminine characteristics! I had an interesting chat with him.

Emily:  Charlie, that's not a very feminine name for a sissy!

Charlie: That's because I'm not a sissy. I am a femboy! A femboy is a male , typically cisgender,  who expresses himself with traditionally feminine  characteristics such as clothing, mannerisms and aesthetics! I love girls clothes, makeup, jewelry and my voice and my movements are very delicate, dainty and femme. But I still identify myself as male. (AMAB Assigned male at Birth)

Emily:  WOW. But you make such a pretty girl! Wouldn't you want to be completely feminized and sissified?  That is, become a complete sissy and identify as a girl? Just like sissy annie here? (Sissy Annie does a cute curtsy and twirls around to show Charlie how girly she is!)

Charlie:  I'm a femboy, and the only "choice" I've ever made is having to fake being masculine so I don't get harassed or assaulted. My femininity is part of who I am, and it's not just something I can change at will. There are some within the LGBTQIA+ community that do not accept Femboy's as a valid form of identity. Because we still technically classify ourselves (most of us at least) as AMAB. But, here was my thought. If a lot of gender identities fall under the Non-binary spectrum, why isn't femboy accept as one of them? It's all about presentation and how we deep down feel and want to be seen right? I know we have Transfemme, Transmasc, Trans, and others that follow the glorious path of Femboy.

Emily:  What about your gender identity? How do you view yourself?

Charlie:  Well personally I’ve always found that being a femboy is kind of outside the question of gender identity. I know cis male femboys, trans masculine femboys, enbies, a person who has a non-binary gender identity, demi-boys, a non-binary person who identifies as partially boy or man and even trans fem femboys. 

That being said, I still consider femboys to be a part of the LGBTQIA+ community because even if you want to try to be reductive and say the community is only about gender/sexuality, femboys struggle with many of the same challenges and barriers that other members of the community also face.

Emily: What are the common challenges and struggles?

Charlie:  They often have to deal with struggling and accepting their identity, leaning to express themselves and dealing with blowback from family, friends, and the public about something intrinsic to their identity. A lot of femboys need a sense of community for support in dealing with these problems. The same problems faced by people gay, trans, ace, etc.) alike, which is why you often see femboys, even cishet femboys, identifying with the LGBTQIA+ community.

Emily: I think FISH Academy could help you with ypur femininity. Your deportment, makeup, wardrobe, etc. We could help you find the perfect feminine image that fits your feminine image of yourself.  You can remain male. Gender identity will not be part of your training. The focus will be on your femininity. Don't you want to be an even cuter femboy?

Charlie:  I would be interested in that. What's involved?

Emily:  That's excellent! Just  email me at fishacademy4sissies@gmail.com and we'll figure our a curriculum that works to make you more femme!  One more question,  Are you attracted to sissy annie?

Charlie: Sissy Annie is so femme and darling.  She is a delightful little girl. But she is a child which completely surprised me. I could see myself as her daddy or uncle taking her to the zoo or to other fun places that children enjoy!

Emily:  Annie would you like Uncle Charlie to take you to the park or zoo or somewhere else fun?  Maybe you would like to wear matching dresses with Uncle Charlie?

Annie: Yes, Mommy. It would be fun to wear matching dresses! Could we both bring our favorite dollies?

Emily:  Annie I am afraid that Charlie does not have a dolly! Isn't that sad? Maybe we need to get him an American Girl dolly too?

The femboy aesthetic

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Sissy Clare's Cotilion presentation

 

It was springtime, and it was time to present young ladies into public society as debutants.  Ms Emily received an invasion to show one of her sissies to public society.  She chose me to be a young sissy lady.  She decided on a white dress with a little pearl breastplate.  It features a tea-length skirt and a flowing design.  

I wore a strapless bra, white panties, and hose with a garter belt.  Mistress Emily helped me with my dress, hair, and makeup.  I'm so pleased that she helped me get ready.  While she was helping me dress, she kept telling me how pretty I looked and how many of the young, gentle men there would be willing to fill my dance card.   I was both nervous and excited.  

She made sure that I wore a charming and fruitful perfume.  I couldn't believe how much of a young sissy girl I felt like—knowing that  I was a sissy being presented into society as a real girl my age. 

When we arrived at the hotel, I went into the staging room with the rest of the other girls and felt a bit nervous, but once I walked into the waiting room, I was met with sweet greetings as if I were a real female teen girl like them. Many of the other girls there told me how pretty I looked and how excited they were to be introduced to me.  

Once the event began, we stood in line.  Holding our cards and stating who we are and a bit about our background.  A lot of the other girls had a long history of past debuts in their families. Then it was my time.

I stood there, knees shaking and knocking, and I heard my name called "Miss Claire presented by Mistress Emily."  I walked in and curtsied at everyone.  They all applauded me, taking lots of photos.  

How wonderful I felt, and as I looked over, and saw a huge smile on the face of Ms. Emily.  I know she was so pleased with how I  presented myself.  

The rest of the night, I  danced with all the other escorts., I couldn't have been happier as a young debutante. 

Isn't sissy Claire a darling little sissy? - Mistress Emily

Sissy Claire is sissy annie's baby sitter! She does an excellent job!

Replies to ...................I am a prissy pink little pansy

Original Post

Nanny Katy and I (Ms Emily) took prissy pink little pansy annie to the mall. Maybe 15 minutes after we arrived I spoke the magic word PINK. It literally stopped sissy in her tracks. She said "PINK" 5 times. Slowly, clearly and in a very sissy-ish voice. I could tell immediately that she was more childish. Maybe a bit more than 3 years old. She took my hand and said to me "I love you mommy, I'm a prissy PINK little pansy". I had dressed her in a pretty pink outfit 

"Of course you are my sweet little princess!. Doesn't that make you happy?" I replied to sissy. She gave me a hug and said "I love being a prissy PINK little pansy. I never want to be anything else."

"That's perfect, my little sissy. That's what we all expect of you." I could see that sissy craved to please me and her Nanny. Her small mincing steps and how she swished her dress as she walked displayed just how juvenile and even babyish she had become.

Not long after we all saw a lovely teenage girl in a pretty pink dress. Sissy Annie went right up to her, gave her a deep curtsy and told her "I love your pretty PINK dress! I am a prissy PINK little pansy."

Sissy was so proud of herself and was smiling waiting for the young girl to respond. She laughed!" I love your dress too. You certainly are a prissy PINK little pansy. What's your name and how old are you?"

"I'm fwee (That's how she pronounced "three"). My name is annie and I am a prissy PINK little pansy."  Annie reached into her little girl purse and gave the girl her personal card!

"I love your pretty PINK dresses! So many! What a lucky little girl! My name is Karen. I'm very pleased to meet you." Annie gave her another deep curtsy and thanked Karen.

Karen turned to me and said, "I assume you are her mom and care for her? She is the sissiest little pansy I have ever met. She seems so happy and enjoys telling everyone what a prissy little pansy she is. She does not seem self- conscious about her dress or being out and shown off as a little girl. I'm amazed that she is not crying in deep humiliation."

"Do you have some time to chat? I asked. "We could go to the food court. I need to feed my sissy baby and we could do with some lunch". Nanny took sissy to the ladies room to go potty and to wank her. After she wanked sissy she saved the sissy cream in a small baby bottle. When we sat down I filled the bottle with baby formula, had it warmed up a bit, and bottle-fed her.

We had an interesting chat at lunch. Sissy told Karen all about her dollies, meeting the Disney princesses and how much she loves being a pretty PINK little pansy. Sissy has always been obedient but this was much, much more. Her need for approval and her regression was so evident! Juvenile and babyish.

Annie - Thank you Nanny Katy. I had a wonderful time!

Nanny Katy - Mistress Emily just had time to share some of what happened. I had much more time to observe sissy annie and her interaction with Karen. Sissy Annie was so animated and exuberant as a prissy pink little sissy! Not much time passed between seeing the pretty lady (Karen) and Annie nearly running to her. Incredible joy and happiness! Her curtsy was very delicate, feminine and girly. But also very juvenile. But that was a perfect display for a little child of 3 or 4.Karen gave annie a warm hug and embrace and asked sissy a few questions about herself before turning to Mistress Emily. Before that sissy annie must have said, more times than I can remember that "I love being a prissy PINK little pansy."

Annie is my little sissy baby. I love breastfeeding her, bathing and dressing her and playing with dolls with her. She is like a true dolly to me.

I love being a prissy PINK little pansy

Girly of the month - June 2025

For the first "Girly of the month" there are 3 beautiful girls wearing the same dress in different colors! The dresses are very light weight chiffon. They feel almost like wearing nothing. The challenge is to hold the dress down when a gust of wind will easily expose a girl's pretty lacy panties! Each girl is wearing matching lacy panties with her dress! Garters & silk stockings also. 

Garter belts and stockings are the perfect thing to wear! Wear them the French way: underwear over the top of the garter belt, not under.

The puff sleeves are perfect and delicate design features. Extremely feminine and girly. These dresses require classic pumps! The pumps may match the color of the dress but not necessarily.  Lastly a pair of beautiful shapely stems complete the look. Soft dressing!!

Each of the girls is wearing her favorite and unique fragrance.

When sissy annie sees a beautiful woman she knows she is inadequate as a male to please her. That triggers a reminder of her goals and affirmations which are the only way sissy can please a woman.

Mistress Emily

prissy pink little pansy fairy princess! (#3)

Where else would mommy take me but to the children's garden! It was so much fun will all the other children running around! I had stickers for all the children who came up to me! They all asked me what fairy I am. I told them I am a prissy pink little pansy fairy!  Giggle

 I love being a pretty pansy with all the beautiful pansies!

                                                    Love, Sissy Princess Annie