Aunt Madeline's Big Surprise Chapter 1
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|Synopsis:||A loving aunt changes her nephew into a girl while his mother is away on a business trip.
Crossdressing / TV
"Aunt Madeline's Big Surprise" Chapter 1
"Adam, stop acting like a boy, this instant!" Aunt Madeline shouted, as
the child ran wildly through the room. "You'll tear your new dress!"
Sure enough, as the eight-year-old scurried past his aunt's elaborately
set dining room table, his dress snared on the arm of a chair and
Madeline Carlson heard the dreaded sound of ripping fabric. Adam stopped
in his tracks and stared at the skirt of his yellow party dress, knowing
that he was in trouble. His aunt was on him in a second and sat him down
on the offending dining room chair.
"Look at what you've done to your dress, child," she exclaimed. "The
ladies and girls will be here for your birthday party within the hour.
Well, I hope that you remember your sewing lessons, young Miss, because,
I will not have you looking like a little match girl in front of my
Adam looked forlornly into his aunt's eyes and said, "I'm sorry Auntie, I
didn't do it on purpose."
The boy started to cry and Aunt Madeline, being the compassionate woman
that she was, felt sorry for her nephew and hugged the petite little boy
to herself. "That's alright dear," she said, but you must stop being so
boyish. I haven't kept you in dresses all summer for your mother to
return from Europe and find you behaving like a boy. Now let's get your
dress off so we can sew the skirt before the girls come."
"Stand still and hold your arms up, sweetie," Auntie said, as she lifted
his dress off the prettily attired child.
With his dress off Adam folded his arms the way girls do as he stood
before his aunt in his white nylon slip. The boy and his aunt smiled at
each other as she gave him a little kiss on his cheek and laid the dress
on the arm of the chair. Madeline thought, "His slip most certainly
becomes him. I love the lace trim on the bodice and the hem. It makes him
look so dainty." Adam, in spite of having worn dresses for just two
months, had become a better behaved child in skirts, even though there
were occasional awkward boyish outbursts such as running in the house.
"Wait here for a moment, honey, while Auntie gets her sewing kit,"
While she had taught the boy to sew on the top-rated Singer 7442 sewing
machine, she thought that it would be good practice for the child to mend
his dress with a simple needle and thread. After all, every boy should
learn to sew.
Handing her nephew a spool of yellow thread and a fine needle, Aunt
Madeline said, "Now remember, dear, how a girl threads a needle. Silly
boys try to push the thread through the needle."
Adam interrupted her saying, "I remember, Auntie. I have to hold the
thread still and bring the eye of the needle toward it."
Aunt Madeline was pleased, as the boy demonstrated that he had been
listening during the instructive "girl times" the two enjoyed throughout
the summer months. Having thread the needle like a well-taught little
girl, he tied off the knot and began to repair the tear in his dress.
Auntie looked over his shoulder as he sat properly like a little lady,
his lacy slip pulled daintily over his knees.
"That's my girl," said Auntie, as the boy put the last of a dozen
stitches in his dress, and tied off the loose ends.
Holding his dress out for Auntie to see, the child said, "Look Auntie,
it's all pretty again."
Aunt Madeline smiled and said, "You did well, child, I am very proud of
you. You were a naughty girl for running in your dress, but you did a
wonderful job sewing, and I think that you deserve a special treat."
"Oh good, Auntie," the boy replied. "What kind of treat?"
Auntie said, "Honey, after we pick mommy up at the airport next week,
I'm going to take you to Clare's Doll Shop at the nearby Mall, and buy
you the pretty doll you were admiring the last time we were there."
Adam smiled broadly and clapped his hands like a little girl. He was so
Aunt Madeline silently reflected on how her nephew had come to love dolls
during the summer as the two of them had little tea parties together.
Madeline had promised Adam's mother Jessica that she would "calm" her
rather boisterous son during his mother's business trip to Europe.
Jessica ran a successful import business that necessitated frequent
overseas trips. Madeline didn't tell her sister exactly how she would
discipline her energetic child, but Jessica gave her full authority to do
whatever was necessary. Madeline hoped that her sister wouldn't be too
surprised to learn that her "secret" behavior modification program for
her boy child involved changing him into a girl.
Madeline was jolted back to the present as Adam said, "Auntie, can I have
the 'Nancy' doll that we saw the last time?"
"Of course you can darling," Auntie answered. "She is the prettiest doll
in Miss Clare's shop and I know that you will treat her like she was your
own little girl."
"Oh, I will. I will," the child said. "I love her white satin dress. Is
she a flower girl, Auntie?"
"Yes, honey. She's a flower girl and she has a beautiful dress. You have
some beautiful dresses too. I must let mommy see you in you ankle-length
white satin dress when she comes back next week, so you can feel like a
flower girl. Won't she be surprised to see her pretty boy looking so
sweet? Now let's get your dress back on darling. Time has gotten away
from us and our first guests will be here shortly."
Auntie raised the yellow dress over Adam's head and let it fall to his
knees, after which she buttoned up the back, adjusted his skirt, and tied
the pretty sash into a lovely bow. She looked lovingly at her nephew and
thought, "He really should have been a girl."
Madeline said, "Now go and read your 'Cinderella' book, dear, while I
freshen up before our company comes." Cinderella was by far his favorite
princess, and the boy scooted off to retrieve the book.
Madeline was pleased that Adam had become such an obedient little girl
and she thought that his mother would be pleasantly surprised to see the
changes in him. Hopefully she wouldn't mind that her little boy now wore
dresses and panties. But now her thoughts turned toward the party. It
wasn't long before five young girls and their mothers would descend upon
the household to celebrate Adam's eighth birthday. Madeline wished his
mother could be present but she would meet her new daughter soon enough.
It is not an exaggeration to say that the boy was overwhelmed as his
beautiful aunt, and four stunningly dressed mothers and their giggling
little girls in party frocks made him the center of attention. Only one
of the ladies and none of the girls knew that he was a boy and everything
at the gathering, from the decorations to the cake to the clothes of the
guests, was decidedly feminine. If anyone suspected that Adam was a boy,
they were too polite to say anything. True, Adam was hardly a girl's
name, but in this day and age, it wouldn't be considered unusual at all
in some circles. And besides, what if they were wrong? No true American
girl would ever want to be mistaken for a mere boy!
Aunt Madeline smiled sweetly at her nephew as the women and girls sang,
"Happy Birthday to you." Madeline cut the cake and handed the first piece
of the pink decorated creation to the boy. His aunt thought, "I'm so glad
that I painted his nails before his party. He looks so cute, and fits in
perfectly with the other girls."
Madeline said, "Don't forget to make a wish, darling."
The child thought for a moment and then made his wish. After all the
girls received their cake and ice cream, the boy motioned to his aunt to
come over to him.
Aunt Madeline approached the eight-year-old who leaned close to her ear
and whispered, "Do you know what I wished for, Auntie?"
Madeline whispered in his ear as she adjusted the boy's yellow hair
ribbon, saying, "No honey. Would you like to tell Auntie what you wished
The boy said, "I wished that I was a girl."
Aunt Madeline felt a lump in her throat as her pretty nephew shared his
true feelings with her.
She whispered, "Oh, you pretty little doll. That is so sweet, Adam. Thank
you for telling Auntie. Mommy and I must talk more about this when she
returns home. I really must consult her if we are going to keep you in
dresses for good. Right now, just enjoy your party and being with all the
Aunt Madeline hugged her nephew and said aloud, "Adam is so happy that
all of you could come to her birthday party." Adam thought, "Oh, she is
calling me "her" again." It made him feel so girlish. But then, who
wouldn't feel girlish dressed in a cute yellow party dress, panties, and
hair bow?" Such a pretty outfit for a boy!
The little girls all clapped and the ladies said nice things to the
little femininely-dressed boy. When all had finished eating, it was time
for Adam to open his presents. Madeline had mentioned to the mothers that
he loved pretty clothes and she had provided each of them with a list of
A little girl named Mary Evans handed the boy his first present that was
wrapped in beautiful pink-colored wrapping paper with a oversized satin
bow. Adam tore off the paper and pulled out of the box a darling pink,
lace-trimmed little girl's slip in his size.
"Oh honey," his aunt said, "look at the pretty slip. How lovely!" Auntie
took the silky garment out of the boy's hands and said, "Stand up,
The child stood up and Auntie held the slip against him. Looking at
Mary's mother, Laura Evans, who had bought the gift, she said, "Thank
you so much, Laura. It will fit him perfectly."
Laura, being one of Madeline's closest friends and one who knew that Adam
was a boy, smiled wryly and winked at Madeline. Laura was a very loyal
friend and understood the importance of training a boy child to be gentle
and sensitive. She had often dressed her own son in dresses before she
had a girl of her own. Laura had picked out a very frilly and lacy slip
for Adam and knew that he would feel unquestionably girlish when Madeline
put it on him.
Aunt Madeline said, "Go and give Ms Evans a hug, honey and thank her for
your pretty slip." The boy stood up, thanked Laura, and gracefully
approached her, holding out his arms to give her a girlish hug. Then Adam
went and hugged her little daughter, Mary, as well. Madeline thought,
"We'll have to get Adam and Mary together to play some time. He needs to
be around girls."
Laura called Adam to her again and embraced him. She smoothed his skirts
and said, "You are very precious little girl, honey. You deserve pretty
Adam Carlson received other gifts from the mothers and their daughters
and not one of them was for a boy. He received a lovely pearl necklace, a
beautiful Scarlett O'Hara vinyl portrait doll from the Franklin Mint, a
"Pretty Little Miss" make up kit, an expensive pleated skirt and blouse
outfit, and a box of silky day-of-the-week panties. The child curtsied
nicely to the ladies and thanked each one for his most girlish gifts.
Aunt Madeline was very pleased with Adam's deportment in front of the
ladies and felt inwardly pleased that the hours spent teaching the child
the finer points of femininity were well worth the effort.
When the last of the guests left the Carlson home, Aunt Madeline called
her pretty nephew to come and sit beside her on the sofa. Adam smoothed
his skirts behind him and sat next to his aunt who put her arm around
"Honey," she said, "Auntie is so proud of you. You were the perfect
little girl and all the guests adored you. Don't you just love being a
Adam looked up at his aunt and replied, "Oh yes, auntie, I'm glad you
made me a girl."
Auntie gave the child a gentle squeeze on his shoulders and continued,
"Tell auntie why you love being a girl, honey."
Adam snuggled closer to his aunt and said, "Because I feel so loved and
"Oh honey," his aunt replied, "didn't you feel loved as a boy?"
"No, Auntie. As a boy I had to act tough and like sports and be ready to
fight with the other boys."
Aunt Madeline held the child even closer and said, "Well, sweetheart, you
do not have to do boy things anymore. You are auntie's girl now and from
now on you will feel secure and protected and not have to worry about
anything. Auntie is going to help you start a whole new life."
"But what about when mommy comes home? She thinks I'm still a boy," the
feminized child said.
Aunt Madeline ran her hand through the boy's hair and said, "Honey, we
will have a big surprise for mommy and I do not think that she will be
disappointed at all."
Adam's birthday party was a great success and Madeline felt that the
feminine atmosphere, the girlish gifts, and the presence of only women
and girls at his party helped draw Adam a little deeper into the feminine
world to which she had introduced the boy.
Another two weeks in skirts did wonders for Adam as he and Madeline
prepared to greet mommy at the airport. He was walking gracefully in his
little girl shoes and had become remarkably feminine in his gestures and
mannerisms. Madeline knew that it was a tad daring to dress an eight-
year-old boy in a dress and take him outside, but she wanted to surprise
Jessica. Hopefully her sister would appreciate the hard work that went
into making her son into a well-behaved little girl.
It was three o'clock in the afternoon when Madeline and her nephew walked
briskly down the airport corridor toward the place where the passengers
deplaned. Madeline had dressed Adam in a little girl's fancy white linen
blouse with a Peter Pan collar. The sleeves were puffed, edged with lace
and ribbons, and very stylish. The boy child was also attired in a cute
patterned blue and white knife-pleated skirt that swished prettily as he
walked. Holding Adam's hand, Aunt Madeline directed the little boy, "Let
your other hand brush against your skirt, dear, so that it doesn't flair
out too much. Your slip and panties are very pretty but we do not want to
show everyone at the airport. We'll save that surprise for mommy."
Adam thought to himself, "Oh my goodness. Mommy has never even seen me in
a dress and she is going to see me in a slip and panties as well." The
child became a little afraid but holding tightly to his aunt's hand gave
him needed confidence. He knew that Auntie loved him very much,
especially now that he was a girl.
Adam stood on his tippy-toes in his shiny black Mary Jane shoes to try to
get a glimpse of mommy as the passengers from her flight began to make
their way toward the baggage claim area. Finally, seeing mommy, Adam
cried out, "Mommy, Mommy, we're over here." Jessica saw Madeline and
waved, but immediately wondered, "Who is that little girl with her?" As
she got closer to her sister and the child, her sixth sense kicked in and
she thought, "Oh my goodness, it's Adam dressed like a little girl."
Jessica, seeing her son in a dress for the first time, was momentarily
However she did not have a lot of time to think about it for the little
boy ran to his mother, throwing himself into her arms. Jessica embraced
Adam and picking him up, immediately felt his smooth bare legs and the
silkiness of the slip and panties that her sister had put on the boy.
Adam said, "I love you, mommy."
Then to Jessica's growing amazement, the child said, "Mommy, do you like
my skirt? Auntie bought it for me."
Jessica, still trying to sort things out said, "Why yes. Yes dear, it's a
very pretty skirt."
Then Jessica looked at Madeline with an expression that said, "What in
the world is going on?"
Jessica lowered her feminized son to the floor and embraced Madeline,
saying, "Madeline, what have you done to my little boy?"
Madeline hugged her sister tightly and said, "Oh Jess, I hope that you
won't be angry with me. Do you remember how you told me that you would be
so grateful if I could settle Adam down a little, you know, get him to be
a better-behaved child?"
Jessica responded, "Yes, sis, I remember that very clearly."
Madeline continued, "Well, you need to know that Adam has become a sweet,
perfectly obedient child."
"But Madeline, look at him. You've made him a girl."
"Yes, I have sis, but it has changed him for the better, just like you
wanted. And Jess, the good news is that he loves it. He really likes
wearing little dresses. He likes pretty slips, wearing my perfume, and he
even asked for a ribbon in his hair so he could look pretty when he met
mommy. He has become so sweet, Jess."
At these words Jessica looked at her son, who was standing watching his
mother and aunt with his hands on his hips like a little lady. His feet
were together and as his mother gazed at him, he brushed back a strand of
loose hair from his face just like a girl. Jessica noticed the satin hair
ribbon, the pretty blouse with the Peter Pan collar, the pleats of his
cute schoolgirl skirt and his Mary Jane's.
Could this be my son," she thought, "the same boy that I left in the care
of my sister three months ago? He looks so comfortable in his little
skirt, as if he has always worn dresses."
Jessica, while not turned off by this overwhelming surprise, was
nevertheless in a semi state of shock. It took Madeline to bring her back
to reality as she said, "Jess, let's get you suitcase off the conveyer
belt and head out of here. My car is in short-term parking lot." Madeline
pulled her sister's suitcase off the belt, and the three girls walked
toward the lot. Adam had taken hold of his mother's hand and his sweet
little skirt swished as he walked beside her.
As Madeline drove, the prettily-skirted little boy sat between his aunt
and his mother. Jessica, while still a little bewildered by the
transformation of her son, began to sort things out. She recalled that
she did ask Madeline to discipline the boy if he misbehaved.. His
behavior had definitely gotten out of hand and a change needed to take
place. But changing him into a girl? Jessica had no idea that Madeline
would put him in dresses. But as Jessica looked down at her son, she did
not see an unruly, figeting little boy in tattered jeans but rather a
well dressed child sitting daintily with his hands folded on his lap. His
legs were together and his skirt was pulled down over his knees. Jessica
could see just a hint of his lacy slip beneath his skirt.
Unconsciously running her hand through the child's hair, she said,
"Honey, you and Aunt Madeline really had quite a surprise for mommy,
didn't you? When did you start wearing dresses like Auntie and Mommy?"
"I think about a week after you were gone, mommy. I was being bad and
Aunt Madeline told me that she had a surprise for me that would help me
to be a good boy."
Jessica asked, "What was the surprise, Adam?"
"It was a pink party dress, mommy," Adam responded.
Jessica said, "Oh my. What happened next?"
Adam answered, "I tried to run but Auntie stopped me and told me that
wearing a dress would be good for me and that it was nothing to be
"Is that when she put the dress on you, dear?"
"No mommy," the child replied. "She told me that a girl can't wear just
anything under her dress. She said that to be a proper girl I had to wear
a slip and panties too."
"Tell mommy exactly what happened, honey," Jessica said.
Adam replied, "Auntie made me take off all my clothes and then held out a
pair of girl's panties for me to step into."
"How did you know they were girl's panties, dear? Maybe Aunt Madeline was
just giving you a fresh change of clothes."
Adam said, "I knew, mommy, because they were not like my boy's underwear.
They were silky and they had lace on them and they had a pretty ribbon on
"Oh my goodness, Adam," Jessica said. "What color were they, honey?"
"They were pink, mommy." the boy replied. "And then auntie put my slip on
Jessica said, "O my precious child, she put you in a slip and panties
just like a little girl. Did you start to feel like a girl, honey?" As
she spoke, Jessica slid her arm tenderly around her little son.
"Yes, mommy. When auntie dressed me in my slip and panties, I felt so
different. I felt much closer to auntie and I liked the silky feeling.
Then auntie told me that I looked so pretty."
"Is that when she put you in your dress, honey?"
"Yes, mommy. Auntie told me to walk around the room a couple of times so
I could get used to the feeling of my slip. Then she called me over to
her and put the dress over my head."
"Tell mommy how you felt, honey."
"I felt soft and gentle like a girl, mommy."
"Did you like your dress, Adam?"
"Well, it felt different than pants. Auntie told me that I would be
wearing my dress all day and that after a day in dresses, I would want to
wear them all the time."
Madeline sat quietly in the driver's seat listening intently to the
conversation between mother and son. "So far so good," she thought. Adam
did not say that he was unhappy about being put in dresses and it seemed
that Jessica was more curious than put off by what happened. Madeline
hoped that her sister would not resent what she did to her little boy.
Changing a little boy into a pretty little girl was such a big step in
his young life.
As mother and son chatted, Auntie said, "Jessica, I know that you must be
tired from your trip but I did promise Adam a new doll for being such a
good girl. Would you mind if we made a quick trip to Miss Clare's Doll
Shop before going home?"
Jessica looked at Adam who was fingering the hem of his dress and said,
"Sure, sis, that would be fine. I'm really not that tired as I slept a
little on the plane."
Jessica was quickly being drawn in to what was happening to her son. If
seeing him in a dress did not sufficiently alert her that he was now a
very different little boy than the one she knew three months ago, the
knowledge that he was about to get his own doll made the change in him
seem even more clear.
She said to Adam, "I didn't know that you liked to play with dolls,
The child answered, "Oh yes, mommy. Auntie and I have tea parties with my
dolls and today she is going to buy me, Nancy."
Jessica said, "Nancy? And just who is Nancy, hon?"
Adam answered, "She's a doll at Miss Clare's, Mommy. She has the
Jessica giggled at her son's remark and looking at Madeline said, "Well,
we certainly would want Adam playing with an ugly doll, would we?"
All three girls laughed at that but the realization that her little son
now liked dolls and dresses penetrated the very depths of Jessica's mind.
She thought, "I think I might like having a little girl. Adam's behavior
has certainly taken a turn for the better."
Madeline parked the car in Miss Clare's lot and the two women and the
little skirted boy entered the shop. Claire Steven's husband was a
corporate lawyer and the two lived in a large home on the edge of town.
Clare did not need to work but chose to keep busy doing something she had
always loved. Like most women, she enjoyed playing with dolls as a little
girl. Consequently, she threw herself into her hobby-profession and
imported the finest dolls from all over the world. Collectors from
several states patronized her shop. She greeted the sisters and their
little "girl" and remembered Madeline and Adam from their last visit.
Clare was one of the few women that knew Madeline and Adam's little
secret. While Adam was looking at dolls the last time they were in the
shop, Clare heard Madeline call him "Adam" and knew immediately that he
was a boy. Rather than register surprise and possibly scare away a
potential customer, she sought to put Madeline at ease saying, "I think
it is wonderful that he likes dolls. I have other customers who buy dolls
for their boys too." Madeline was momentarily dazed because Adam was not
dressed as a boy. He was in a dress!
Sensing the uncomfortableness of her customer, Clare immediately followed
up her remarks saying, "I love little boys in dresses. They look so
adorable. You must be very proud of him."
This eased the tension, and prompting Madeline to reply, "Thank you so
much. Not many people know that he is a boy." The two ladies developed
an immediate bond and Madeline felt quite comfortable returning to the
shop with Adam and his mother. Clare greeted them warmly and Madeline
introduced her to Jessica. Madeline whispered to her sister, "It's o.k.
Clare knows all about Adam."
Clare said, "I think that it is delightful that you have a gentle little
child." Jessica, who was hardly ready to announce to the world that her
once manly little son was now a sissy little girl, stuttered, "Well,
thank you, I guess. My sister totally surprised me when I returned from
Europe this evening. I'm not exactly used to seeing Adam in skirts."
Clare said, "Oh hon, I think that it is wonderful. Adam is not the only
boy whose mother wants him to be sweet and gentle. I told your sister the
last time that she and Adam were here, that I had other customers who
bought dolls for their sons."
"Really?" said Jessica. "Well, that does make me feel a little better."
"It may take time to get used to it, Jessica," Clare said, "But once you
do, you'll be glad that your sister made him a little girl. My sister has
twin boys and she tells me all the time that she wishes they were girls.
It would not surprise me at all if decides to put the boys in dresses.
They are only four and would be adorable little girls. 'Besides,' she
said with a laugh, 'it would be a lot easier for me to choose birthday
presents for them from my shop.'"
Madeline and Jessica continued chatting with Clare until Madeline said,
"Well, girls, Jessica is probably getting weary after her long plane
trip, so we better get on with business. "Clare, do you remember the
'Nancy' doll that Adam was admiring the last time we were here?"
"Yes, I do," Clare replied. "She's the little flower girl. Let me get her
Clare returned with the precious doll and handed it to Adam, saying, "Is
this the doll that you wanted, honey?"
Adam held the doll in his little hands and ran them down the satin skirt.
The boy examined her petticoat and then looked into his mother's eyes,
saying, "May I have her, mommy? Auntie said I could."
Jessica found herself getting emotional as she observed her girlishly
dressed boy asking her if he could have a pretty flower girl doll. She
thought, "I do not think I have a little boy anymore."
Snapping out of her daze, she replied, "Yes, honey. You may have her."
The boy smiled and said, "Oh thank you Mommy and Aunt Madeline." He then
kissed his little doll and all the women smiled at what appeared to be a
perfect little girl. Madeline paid for the doll and the ladies said
goodbye to Clare. Adam held his doll tightly as they returned to their
car for the ride home. It had been a long day for Jessica, and one full
of surprises, the greatest of which was learning that her unruly boy had
become a darling little girl in her absence. She thought, "I wonder what
the next few days are going to bring as I get to know my little child
The three "girls" got into the car with the newest little female seated
between them clutching a flower girl doll. Adam had been a nice, although
misbehaving boy before Jessica's trip, but now, thanks to Aunt Madeline,
he had become a sweet mommy's girl, ready to learn more about being a
young lady. Jessica thought, "There is so much I have to teach him." The
future looked like it would be filled with girlish fun and Jessica smiled
as she closed her eyes in anticipation of growing closer to her new
daughter in the days and weeks ahead.