His Mother's Hair, Part 1b
His Mother's Hair, Part Ib
By Melissa Anne Curling
No one in the household slept soundly that night. Wendell, his Mother,
and his Auntie Arlene were all tossing and turning instead of sleeping.
They all had different aspects of the events of the previous day and
evening on their minds. Poor Wendell's mind was full of worry and
excitement and, for the first time he was trying to sleep with his hair
up in rollers.
Arlene had arrived the earlier that day for what she thought would be a
relaxing visit with her sister, Madge, and her nephew, Wendell. Instead
she had witnessed an amazing, and, for her, sexually charged scene
lasting several hours. In a short time, Wendell went from a typical boy
with longer than normal and somewhat unruly hair, to, at least in
appearance, a feminine looking young teenage girl. 'She' went to bed
wearing his Mother's nightshirt with his hair put up in rollers. And, to
top it all off, his Mother's pink curler bonnet covered his roller set.
This intrigued Arlene and definitely exited her.
Her divorce from her macho husband was final months ago, and now, in the
quiet of her bed in the guest room, she ached for the touch of her new
paramour. The new woman in her life was a lovely but forceful woman that
she met on the Internet. Her mind wandered back months ago to their
meeting and first intimacy together. Shortly after their second torrid
love making session she was led to her lover's barber chair and her rich
brown locks were clippered away from her head. She thought about her new
girlfriend and the excitement of being forced to get her haircut and how
it led her to a shattering orgasm in the barber chair while the clippers
buzzed over her head. She reached up and ran her fingers through her
close cropped head and moaned as she thought of her barberette and her
clippers. It made her instantly wet.
She also thought of her own son, Jimmy. She wouldn't think of pushing him
in the direction that his cousin Wendell seemed to willingly be going in.
She laughed at the thought of such a thing. Jimmy was 'all boy' and kept
his hair in almost a crew cut. Sports were his thing and there wasn't a
girlish bone in his body.
Then Arlene thought of Wendell. She certainly had a hand in the direction
the day had taken. She easily coerced Wendell into brushing and braiding
his Mother's hair. But, that was only the beginning of her fun.
Eventually, she had him helping with her shampoo, and then, even had him
in a frilly apron putting his Mother's hair up in rollers. While Arlene
was decidedly submissive with her new lesbian lover, she had a dominant
streak when it came to males. Her son was off limits in her complicated
psyche but every other male was fair game.
In fact, she thought about her secretary, Andrew. He was a doll in his
own right and she admired his subtle femininity. She loved to watch him
prance in wearing his tight cut pocketless trousers and silky shirts. She
smiled to herself thinking that some of his tops had buttons on the left,
some on the right. Even his shoes matched that little purse he always
carried. Especially on Mondays, he would come in with a little extra wave
in his hair. Yes, she loved having a swishy male secretary. From time to
time, she would refer to him as 'Ann' shortening his name from 'Andrew'
and he never said a word.
Earlier that evening, she managed to also put a roller in Wendell's hair.
She thought back to supervising him while she taught him to set his
Mother's hair. These thoughts brought her fingers down between her legs.
As she started to quietly satisfy herself, she thought about Wendell and
how he sat so patiently in his apron while his Mother put his hair up in
rollers. The thought of his Mother winding the rollers down to his head
and securing them with large roller pins brought her body to a fulfilling
orgasm. It was by now late into the night and she was finally able to
drift off to a sound sleep until the morning light would awaken her.
In the master bedroom down the hall, Wendell's Mother, Madge, had her own
thoughts keeping her from sleep. It was late when they went to bed and
she fell asleep quickly but woke a couple of hours later. When she awoke,
her thoughts immediately turned to her son. He had been so passive that
afternoon and evening. She couldn't ever get him to help with the
housework because he said it was 'girl's work' and a few hours ago he was
happily helping brushing, braiding, shampooing and setting her hair. And,
he wore a frilly apron through most of the process. She thought about how
he didn't strongly object to anything that occurred. He didn't fuss; he
just went along while he helped with her hair. He even went along when
she suggested that he let her put his own hair up in curlers and then
confessed that he wanted her for a long time to do it!
She wondered what Wendell did do after he went to his room to retire. She
told him he could take his hair down and shower. She didn't hear the
shower running so she assumed he still had her brush rollers in his hair
and was wearing her nightie. She also assumed he was in a deep sleep
across the hall but she was wrong.
She thought about how she had always wanted a daughter but was deprived
of that joy. She thought about how she loved having a son. He was gentle
and kind but not like other boys. He wasn't at all athletic. She didn't
care. He was a good boy.
As she rolled from one side of the bed to the other adjusting her pillow
to make the curlers in her hair more comfortable for sleep, she thought
about her sister's words before dinner in the kitchen. Arlene had called
Wendell a sissy. Was Wendell really a sissy? She couldn't argue too
strongly that he wasn't. After all that had happened that day, he wasn't
exactly a 'boy's boy' - that's for sure. He didn't play or even like
sports. The girl next door was a close friend and a year younger than he
was and she pushed him down and he tore his shirt. Did he fight back? She
was sure he didn't. And, then there was the visit to his Grandmother's.
Knitting? Cleaning her house? Oh, my.
Madge thought about how small he was 'down there' and wondered if that
was part of all of this. How would he even know that he was under
endowed? There was no way he could be aware of that! It bothered her to
think about it so her thoughts went elsewhere.
"Oh God, my son is a sissy," she said out loud into the darkness of the
room. There, she thought, she had admitted it to herself. She had met
plenty of sissies in her days as a beautician. She had two effeminate men
working for her at her beauty college. She had countless more enroll
there since she opened the college. She liked having sissies around. They
were neat and clean and very girlish, and always seemed so willing to
please. She loved that about them. Would Wendell want to go to beauty
college after he finished high school or even before? She could easily
picture him in her class.
She looked at the clock and saw that it was 3:30 A.M. She couldn't wait
until morning to find out if Wendell was now as he was when she last saw
him. She decided to get up and check on her boy. She walked quietly down
the hall and slowly opened Wendell's bedroom door. He was lying in bed
facing away from the door but she could see enough in the dim light from
the hall light fixture behind her that he was at least still wearing her
curler bonnet. As she started to close the door, she heard a faint voice,
"Mommie?" she thought she heard.
She entered Wendell's dimly lit room and walked quietly to the side of
Wendell's bed. She thought about how he still slept with a night light
and smiled. She noticed her shadow on the wall and with the curlers in
her hair it was quite a sight and she tried to cower down. She didn't
want to scare her boy if she woke him up. To her surprise, he rolled over
and reached out for her. Madge knelt down by her son's bed and put her
arms out to hug him. The curlers in her hair met his so it was a very
awkward hug. They giggled and adjusted their heads to make room for the
rollers and he pulled her close hugging her tightly. His hug was so firm
around her neck that it began to hurt her.
"Wendell, honey, what's the matter? Tell Mommie what's wrong. Did you
have a bad dream?" she whispered hoping he would loosen his grip on her.
Wendell kept hugging his Mother tightly and started to whimper.
"Here, honey, sit up. Let your old Mom hold you," Madge said pulling her
son up from the pillow. She sat down sideways across the bed, moved her
bottom back and leaned against the wall. She pulled her curler headed boy
across her lap and held him in her arms with his face up and his head
against her breasts.
"Mommie ... Mommie, why ... why am ... why am I like this?" he finally
said and quietly started to sob.
"Like what Wendell?" she said trying to avoid the obvious nature of his
He continued to cry in her arms.
"Oh, sweetie, please don't cry. We've had so many tears today. It'll be
all right. Don't worry, it'll be all right- I promise. You aren't doing
anything wrong," Madge comforted not really knowing what to say. "What's
wrong baby? Why is all of this bothering you so much? Tell Mommie what's
really wrong," Madge begged.
"Mommie," he paused, "why do I like this so much?" he finally said
putting his hand up to the rollers in his hair. "I just don't
"The curlers in your hair?" she asked cautiously.
"Yes. Why did I want you to put these things in my hair? Why does it make
me feel so funny down in my tummy? Why Mommie? Please tell me. Why?"
Wendell pleaded quietly.
"Do you still like having those curlers in your hair, sweetie? Tell
Mommie how you feel right now. It's important," she replied.
"Yes, I guess so. I think I do," he sheepishly said.
"I need to know exactly how you feel about all of this. In fact, maybe it
would be easier if we take the rollers out of your hair. Then, maybe we
can talk a little easier because you won't be so distracted. Here, sit up
and let's get all of this stuff off of your head," Madge said starting to
take the curler bonnet off the side of her son's head that was closest to
"Please, Mamma, no! Please ... " Wendell said firmly.
"I think I just got my answer, honey," Madge said replacing the curler
bonnet back down over his curlers. She pulled him back down to her breast
and went on to explain, "Sweetie, everyone in this world is a little
different. People come in all shapes and sizes and their brains all work
differently. There are boys out there that are rough, tough sports type
guys and there are others that are more ... delicate," she said having to
pause for a moment because she didn't want to use the word 'sissy'.
"There are girls that grow up to be ladies like me. You know- feminine,
wear dresses most of the time, love to fix their hair, and love to run a
home. I have to work but I work in a very feminine profession. Some of us
are even downright prissy. Your Aunt Arlene; on the other hand, is a
little more ... masculine. She cuts her hair short; rarely, if ever,
wears make up; wears slacks and a jacket to work and is employed as a
corporate attorney. Take a look at Shelly next door. I'll bet when she is
a little older her pretty curls will disappear and she'll be going out
for her school soccer team- (or joining the Army, she thought privately).
And, I'll bet someday she'll be the captain of her team."
"What about me, Mamma? What kind of boy am I? What kind of boy wants
curlers in his hair? I enjoyed being at Grandma's house and helping her.
She made me the prettiest apron and it made me feel so good to wear it.
When Shelly pushed me down and I didn't fight her back she called me a
'sissy'. She's called me that before. What does that mean Mommie? What is
a 'sissy'?" Wendell asked.
"Has anyone else called you that name, honey?" Madge asked while she ran
her fingers over her son's roller set and protectively rocked him back
and forth gently against her breast.
"My friends call me that sometimes," he volunteered. "They say I'm a
sissy because I don't play sports. Lot's of people don't play sports.
Most of the girls at school don't play sports. Are they sissies, Mamma?"
"No, honey. Girls are just girls. A girl can't be a sissy. Only a boy can
be a sissy. Sometimes girls can be girlish girls and sometimes they can
be tomboys but they can't be sissies. You know what a tomboy is? Like
Shelly," Madge explained.
"What about me, Mommie? Am I a sissy?" he innocently asked.
"I think if you look up the word 'sissy' in the dictionary, you'll find
that a sissy is an effeminate man or boy. Effeminate means that you are
feminine- that you act like a woman or, in your case, a girl. Wendell,
honey, I heard from a certain someone that you like to knit, I know you
enjoyed doing your Mother's hair, and you even enjoyed having your own
hair put up in rollers. Tell me about the nightshirt and the panty that
you are wearing. How do they make you feel?"
"I guess they make me fell nice. Your nightie is very soft Mother and I
love the smell of your clothes. They smell like you. So, yes, I guess I
enjoy wearing your things," he answered.
"You are the sweetest boy I could ever have. You said that you 'guess'
you enjoy wearing these clothes. Or do you truly enjoy it?" she asked
emphasizing the word 'enjoy'. "See, there is a difference. I really need
to understand how you feel about wearing my clothes and having your hair
set, Wendell. Do you 'guess' you liked helping your Grandma do her
housework while you were wearing your pretty apron? Or, did you truly
enjoy wearing your apron and helping Grandma? I understand that you wore
your apron not only when you helped her with the housework and when you
worked on your knitting projects, but almost all of the time," Madge
"Yes, Mamma, I did wear it all of the time. It made me feel so ... so
special. Mom, I really enjoy wearing your nightie and your panty,"
Wendell said firmly.
"Then, you know Wendell, I would have to say that you are a sissy.
Understand that's not really a bad thing. It just means that your are a
feminine boy. Sissy has come to be such a negative word and there's
nothing negative about you- nothing at all. I want you to know that your
Grandmother told me all about your visit." Madge added so Wendell would
know there were no secrets.
"And tonight wasn't the first time you helped put curlers in a lady's
hair, was it?" Madge asked.
"No, Mother, it wasn't. I helped Grandma set her hair but only a little,"
the boy admitted.
"That means you lied to your Auntie when you told her that you had never
done that before. You know what happens when you lie, Wendell. Mommie
gets angry and you get a spanking," Madge said without anger.
"Yes, Mamma, I know," Wendell said softly.
"Well, we'll have to deal with that tomorrow. Tell me, if I got your
Grandma to make you an apron to wear here at home, would you like to wear
it and help me with the housework?" Madge asked as her heart started to
beat a little faster.
"Oh, yes, Mamma, I would. I would like that very much," the boy answered.
"Would you like to continue to help me with my hair, sweetie?" Madge said
feeling now like her heart was pounding hard enough that her son might
notice as his head was at her breast.
"Mamma, please, please let me keep helping you with your hair," Wendell
"You know that you'll have to wear your apron when you do my hair, baby
doll," Madge insisted.
"I'd like that, Mommie, I really would," Wendell affirmed.
"We have a lot to sort out, sweetie. There are lots and lots of things we
need to talk about. First of all, I don't want you hiding the fact that
you are a sissy, Wendell. That would make me uncomfortable, it's
dishonest, and I want you to feel good about what you are. It's really
important that you are happy and I'd like you to even be proud that you
are a sissy. Do you understand what that means?" Madge asked.
"I'm not sure, Mamma. Please tell me," Wendell asked
"Well, for starters, I think we should start fixing your hair in a
girlish way and you can wear it in a girlish style all of the time. You
know that curls in your hair, ribbons, barrettes, and even braids would
tell everyone that you really are a sissy. In fact, when I do your hair
the next time, I think you'll end up with some pretty little ringlets,"
"Like Shelly's hair?" Wendell asked.
"Yes, like Shelly's" Madge said.
"Oh, I'd like that, Mommie," Wendell murmured as he smiled
"Don't be disappointed because your ringlets just won't hang down as far
as Shelly's because your hair isn't that long yet. But don't worry about
that, we'll let your hair grow to be as long as you want it to be. So,
anyway, in the next day or so, you will have ringlets," she confirmed.
"Now, you'll have to be a good boy and you'll have to ask me nicely to do
that for you," she added wanting to be sure that when the time comes it
will be of his choosing.
"I will, Mommie, I will," Wendell said softly.
"So, you understand that from now you will always have a very girlish
hairstyle. That will be very nice. You will have to be willing to go out
of the house or to the store or to the mailbox with your hair in curls or
even curlers and you'll get a lot of name calling from the kids in the
neighborhood," his Mother warned.
"I don't care, Mommie. As long as I don't have to fight them because I
don't want to ever be in a fight," the effeminate boy explained.
"Don't worry about that, sweetie. I'll protect you from any fighting.
Wendell, since we are in agreement that you are a sissy and we aren't
going to hide it anymore, we should start this stage in your life off
with a clean slate. I want to take care of this lying business right now
so we don't have to think about it again. Why don't you sit up for a
minute," Madge asked. She then scooted away from the wall and sat on the
edge of the bed with her feet on the floor. "Come here, Wendell, lay face
down with your middle across Mommie's lap," Madge instructed.
"Why, Mommie, why?" he asked.
"I am going to give you a little spanking for lying. Now, pull your
nightie up and come here," Madge said pulling his arm toward her and
across her lap. Wendell pulled his nightgown up exposing the panty he was
wearing as he was positioned across his Mother's knees. Madge balanced
her son's weight until she was comfortable.
"There, that's good. Just be still for a moment Wendell," Madge whispered
as she took in the sight of her girlish son. Her son's peach nightshirt
was up around his waist exposing the control pantie she had put him in.
His hair was up in brush rollers and he had a pretty pink curler bonnet
covering his set. She had her left arm wrapped over him securing him to
her lap. Her right hand had found its way to his pantie covered bottom
and she started to gently caress him there. "I have an idea, honey.
Instead of just letting your arms hang down like that, why don't you
reach up and wrap your fingers around the rollers in your hair while I
give you your little spanking," she suggested.
Wendell complied and his Mother said, "That's a good boy, hold your
curlers just like that. Don't the rollers in your hair feel good, baby?
Your hair is going to be so pretty tomorrow when I fix it for you- just
like a pretty girl. You know, you have a really cute little bottom,
honey. It's so nice and soft and it looks so pretty in Mommie's panty. I
know you like having your Mommie do your hair. Do you like wearing
panties, too? Are you going to be Mamma's panty boy and wear panties for
her all of the time?" she asked.
"Oh Mommie ... " Wendell uttered.
"I know sissy, I know. We'll get you some nice panties of your very own.
Won't that be nice," she teased as she rubbed her hand over his bottom.
Wendell started to rub himself against his Mother's leg and his Mother
sharply said, "No, Wendell, there will be none of that! You've now earned
four swats with my hand. Two for lying to your Auntie Arlene, one for not
telling me a long time ago that you had these girlish feelings, and one
for what you just tried to do to Mommie's leg. Now hold still!" Madge
ordered and delivered the first little swat of her hand. She wondered if
he even felt it. If the truth were known, that was her intention.
"There, that's one," Madge counted in a business like tone while rubbing
her son's bottom.
"Mother, my arms are getting tired," Wendell said cautiously.
"Just another minute, Wendell. Don't be such a sissy," Madge said and
they both giggled at her words.
Madge gave her son three more quick but gentle little slaps on his
"There, all finished, honey. Let's get you up now," she said as she
helped raise him up off of her lap. As he stood, his nightshirt fell back
down to his knees. "Just don't forget to apologize to your Auntie for
lying to her."
"I won't Mother, I promise," he said with a smile.
Wendell certainly didn't have any tears as Madge was only intending on
getting her point about lying across to her son- not to hurt him. She
didn't have the ability to hurt him in any way imaginable. She meant for
Wendell's middle of the night spanking to be more of a symbolic gesture
than anything else.
"Into bed you go, Wendell," Madge said pulling the covers back.
Madge turned the light on in Wendell's room and stood beside the bed.
"I'm just exhausted. Do you think you can sleep, honey?" she asked the
now calm girlish boy reclining in his bed.
"I think so, Mamma," he answered.
"I want you to go to sleep thinking about two things. Will you do that
for me?" Madge asked as she covered her son with his blanket and
"Of course, Mother," he replied.
"Your Grandmother is coming to visit us tomorrow afternoon. I want you to
think about what you would like to wear with your new hairstyle. I want
you to dress nice but you are going to have a very girlie hairstyle
assuming that is what you still want to do when the morning comes. She
might not understand if you are wearing rough boy clothes and have your
hair looking pretty. Just so you know, when I take your curlers out and
style your hair, it is going to be very full all around your head and
have a little curly flip at the end all the way around. And, I'll
probably put a little bow in your hair on the right side just to make it
even prettier. It'll be really cute, you'll see," the boy's Mother said
pointing at him with an exaggerated limp wrist.
"Yes, Mother," he obediently said.
Then she added, "And, the other thing I want you to think about is, when
it is appropriate, I think it would be nice if you ask your Grandma to
make you two new aprons to wear. I want you to tell her that you are
going to start helping me around the house and that you will need them to
do your housework. Is that understood?" Madge said with a firm tone.
"Yes, Mother, I promise I will," he said. His Mother leaned over and
kissed his cheek as he closed his eyes hoping to drift off to sleep.
"Good night, pretty boy, good night," Madge said as she closed Wendell's
"Mother, one more thing, please," Wendell said.
"Yes, my sweet boy" Madge said going back to his bedside.
"Thank you, Mother. Thank you so much," he said softly.
"You are ever so welcome honey. Sweet dreams," Madge said.
As she closed his door, Madge was about to unravel thinking about what
had just gone on. She almost ran down the hall to her room and closed the
door behind her locking it. Wendell had just made it clear that he was
willing to wear his hair in a very girlish style. Oh God, she loved the
very thought of fixing his hair! He also let her know that he would be
pleased to wear panties. This was all just happening too fast and it was
so exciting for her. When he was across her lap and she said the words
'panty boy' to him, she thought she had a small orgasm.
She was primed for an intense sexual release and reached for the drawer
containing her trusty vibrator so she could take care of her need. After
doing so, she went to sleep.
That morning the sun shone brightly through the windows on the eastern
side of the house. Madge woke up and heard those noises that told her
there were others up ahead of her and wondered who. "What time was it
anyway?" she thought. Then she gave thought to the time that she had
spent with Wendell in the middle of night. "Was it all a dream?" Then she
moved in her bed and realized she was lying on top of her vibrator. "God,
that was the best orgasm I've had in a year," she thought still feeling a
little bit randy.
Madge put on her summer robe and slippers and looked for a scarf to cover
her rollers. When she looked in her scarf drawer, she saw a flowery print
peach scarf and she thought about Wendell. "Why not?" she thought and she
put the scarf into the pocket of her robe. She covered her rollers with a
scarf that matched her robe and opened her bedroom door. The wonderful
smell of brewed coffee immediately hit her senses. Now she was sure
Arlene had been up before her. As she walked down the hall, the guest
bathroom door opened abruptly.
"Hi Sis, did you sleep well?" Arlene asked her sister as she yawned her
way out of the bathroom.
"Not bad. I had a long night. I'll have to tell you about it. Thanks for
making the coffee. That was sweet of you," Madge said.
"I didn't make the coffee. Haven't been downstairs yet. Just let me take
a quick shower and put my shorts and tank top on. I'll be right down,"
Arlene said as she headed for the guest bedroom.
Her curiosity regarding the coffee was mostly on her mind as she
descended the stairs. Only a step into the kitchen, she stopped abruptly.
The scene before her warmed her heart and to a certain extent, her
womanhood. She smiled as she surveyed the room.
Wendell apparently was up before his Aunt and Mother and had been at work
in the kitchen. He had organized Madge's entire selection of hair
supplies and her curler basket from the night before as they had been
left strewn about the kitchen table and counter. They were all neatly
arranged at the end of the counter.
He even had tidied up her curler basket arranging the remaining few
rollers in the basket by size.
He, of course, was still attired in his Mother's peach nightshirt and
curler bonnet. He had put the apron on that he had worn the night before
during the hair setting marathon that went on for he and his Mother. The
bow in the back was a mess but she just couldn't criticize the way he had
it tied even though she thought about it. The apron was so large for him
that it would have been difficult for him to tie a reasonable bow. And,
in the scheme of things, it was so unimportant. She noticed that he even
remembered to put on his new pink monogrammed slippers.
He had set the table for breakfast using place mats, her everyday dishes,
napkins, silverware, juice glasses and coffee cups. The creamer and sugar
bowl that matched the dishes were there although she rarely used them. He
had made coffee and even had a pretty yellow rose in a bud vase on the
table. This was a truly warm and wonderful scene.
"Wendell, you are such a doll! How did you do all of this? When on earth
did you learn to make coffee?" Madge exclaimed.
"Mother, may I get you a cup?" he sweetly asked.
"That would be great, but I'll get it," Madge said as she went to give
him a warm hug.
As they embraced, Wendell whispered in her ear, "Please Mother, please
let me serve it to you, please."
"That would be fine, darling. But first let me do something for you. I
want you to take off your curler bonnet. It's just for sleeping, you
know," Madge explained reaching up and gently removing the pink ruffled
"Oh ... " Wendell groaned sadly.
"Don't worry, baby. You can wear it again tonight. I thought you might
like this," she said as she pulled the pretty peach scarf from her robe
"Oh Mother ... " he said softly.
"It's pretty, isn't it?" Madge said. "You can have it if you want it.
It's a little too loud to wear out and about. But, I always liked to wear
it over my rollers. It's so ... so ... " Madge stumbled for the right
word and gestured with her hands.
"... feminine," Wendell finished his Mother's sentence.
"Yes, honey, feminine. That's the word. Let me show you how to wear it as
a cover for your rollers. Now, I usually wear mine like this," Madge said
pointing to the triangular scarf covering her head that was tied at her
neck underneath the bottom curler in her hair.
"For your first time though, I thought you might like to wear it in the
old fashioned way. This is the way your Grandma would have worn a scarf
around her rollers to do housework. First we fold it in a triangle like
this. That's the way I folded mine. But, now we'll put one more fold in
here," Madge said folding the point of the triangle back to the single
fold so it was in a sort of rectangular shape but with pointy ends. She
then carefully picked up the silky scarf.
"Lean your head down, sweetie. Look at my slippers," Madge instructed.
Wendell complied and his Mother wrapped the folded scarf around the back
of his rollers pulling the ends of the scarf to his forehead.
"Now, we tie the ends across the top of the first two curlers, one more
tie to keep it from unraveling and, ... there, we're done. We just have
to take these loose ends and tuck them in here ... and in here and ...
there you are! So pretty" she said as she held his curler covered head in
her hands and kissed Wendell on the forehead.
She grabbed the large hand mirror from her curler box and handed it to
Wendell. "Look sweetie, see how pretty the scarf is?" she asked. Without
waiting for an answer she said, "See, the scarf is holding your rollers
all the way around your head so they won't get mussed up. And, if you
bend your head forward a little you can see in the mirror the rollers on
the top of your head with the pretty pink hair net over them," she
"Mother ... I ... " Wendell's voice cracked as he tried to talk.
"I thought you'd like being able to see the curlers on top when you look
in the mirror," Madge said confidently. "Let me fix the bow in the back
of your apron, honey. It's a mess," Madge said spinning her son around.
Madge fixed the bow quickly and Wendell turned around. Realizing he
couldn't get any words out, he went again to hug his Mother. He put his
hands on her shapely hips and looked into her eyes and tears started to
well up. But, this time they were tears of joy.
"Are you happy, honey?" Madge asked tenderly.
"So happy, Mother, very happy," and he gave her a tender hug. It was such
a tender moment and defining gesture for their future.
With a tear in her own eye, Madge kissed him on the cheek and asked,
"Where is it that you want me to sit?"
Wendell cleared his throat and said pointing, "Your place is always at
the head of the table since you are the head of the house. So, you should
sit there. Auntie Arlene should sit at the other end of the table since
she is your sister and my Auntie. I'll just sit here on the side. If you
need anything during breakfast, then I can get it for you," he explained.
Wendell helped his mother to her chair, got the coffee pot and served his
mother a cup being careful not to spill a drop. Madge gave thought to the
fact that his Grandmother had trained him well.
"So thoughtful. You are simply amazing. But you didn't answer my
question. The coffee?" the boy's Mother asked while she prepared her
coffee with a little creme and sugar.
"You and Grandma have the same coffee pot, remember Mommie? She bought it
for you because you liked her coffee so much. Grandma taught me how to
make coffee for her when I was there for my visit," Wendell proudly
"It smells scrumptious," she smilingly said as she savored its bouquet
and took her first sip. "Hmmm, honey this is sooo good! And you served it
perfectly!" she added wanting to compliment her sissy son. "And how did
you learn to do that" Madge asked.
"Serving coffee? Grandma taught me. One day I even got to serve coffee
and cookies to Grandma and her neighbor friend, Mrs. Damson," Wendell
"You served the ladies?" Madge asked incredulously.
"Oh yes, Mother. Mrs. Damson came over one afternoon and she and Grandma
had coffee and some cookies that Grandma and I had baked that morning. It
was ever so much fun!" Wendell girlishly beamed.
"I have to ask Wendell, did you wear the apron that Grandma made for you
when you served the ladies their coffee?" Madge asked with an eyebrow
"Oh no, Mother. My work apron was dirty so Grandma had me wear one of her
other ones," he explained.
"And?" Madge asked bursting with curiosity.
"Mother, please ... " Wendell said blushing a little and trying to beg
"Wendell, don't be shy with me. We can have no secrets between us. Tell
me about the other apron that you wore," Madge ordered.
"Well, it was not as big as my other one. It only went from my waist down
to about here," the boy said pointing to just below his knee. It tied in
the back like my other one but the material was kind of pink and you
could see through it. It had a heart shaped pocket on the right side made
of a dark pink material. And, there was what Grandma called a 'ruffle'
all around the outside of it. It was really pretty but I didn't want to
wear it," Wendell explained. "Well, sort of, I did," he added.
"Why ever not? It sounds delicious. But you wore it for Grandma and Mrs.
Damson didn't you?" Madge asked.
"Yes Mother, I did. I was a little embarrassed but Grandma said I should
just go ahead and wear it and I didn't want to argue so I let her put it
on me," Wendell said.
"You are such a good boy. So you enjoyed serving the ladies? How sweet!"
Madge said as she beamed with pride.
"Did Grandma teach you to set the table? You did a wonderful job this
morning. Everything is perfect," Madge complimented.
"Oh no, Mother!" Wendell exclaimed. I forgot the salt and pepper shakers!
Please don't be angry with me," he pleaded.
"My sweet child. You did everything so well this morning I couldn't
possibly be angry with you about anything. Besides, unless we're cooking
eggs, we won't need them. I think we should make setting the table one of
your permanent jobs around here. You can make coffee for me in the
morning, too. Would you like that? We can even make a little check list
for you until you learn everything so well that it is second nature,"
"Thank you, Mother, I would like that," Wendell replied.
Arlene walked into the kitchen at that precise moment. "Hello girls!" she
happily said. After all, it was quite a sight. Mother and son were
sitting at the kitchen table in their feminine night wear and hair
rollers, each of their heads covered with a pretty scarf.
"Arlene, I'm going to smack you!" Madge said angrily. "Wendell and I had
a long talk in the middle of the night. We've got a lot to sort out and
we're taking this whole thing very seriously and one step at a time.
Wendell, do you have something to tell your Auntie from our little talk
"Please sit down Auntie Arlene," he said as he pulled her chair out for
her. After he helped scoot her chair in like a polite young man would, he
sat down and said, "Mother and I had a talk last night in my room. I lied
to you when you wanted me to set Mother's hair and I told you I had never
done that before. I helped Grandma set her hair during my last visit. I'm
sorry, I won't ever lie to you again."
"Apology accepted, honey. I thought you might not have been completely
truthful with me. Madge, when we were kids, Mom used to wail the
daylights out of us if she caught us lying," Arlene said trying to lead
her sister on.
"Well that's not going to happen here. Wendell has already been
disciplined and, under the circumstances, I think we should drop this
topic," the boy's mother said.
"O.K. by me. Spare the rod and spoil the child ... " Arlene added.
"If you must know, Wendell got a little spanking over my knee already. So
drop it!" Madge said raising her voice a little.
Wendell smiled and looked away thinking about the 'spanking' he got in
the middle of the night. He remembered how they giggled when he was over
his mother's knee and she told him was acting like a sissy. He wished all
of the few spankings he had received in his life had been like that one.
Arlene was glad she had the foresight to use a panty liner that morning.
Her juices were flowing again thinking about her curler headed nephew
over his Mother's knees.
"So, did you two have a nice little chat early this morning?" Arlene
"We did as a matter of fact. Didn't we Wendell?" Madge asked her son.
"Oh yes, Mother. It was wonderful," Wendell glowed.
"Can you tell me about it or is it a secret that's 'just between us
girls'?" Arlene asked and quickly added, "Don't get your panties in a
knot, Sis, it's only an expression!"
Wendell wanted to quiet the conversation and offered, "Mother says that
I'm a sissy, Auntie."
"That's wonderful, sweetie! I'm so happy for you. How do you know you're
a sissy? Just exactly what is it that makes you a sissy? What do sissy
boys do?" his aunt asked him innocently as she tried to hide her
"Well, Mother says that in the dictionary it says that a sissy is a
feminine boy. I like to do girl things and I like to wear Mother's
clothes so that makes me a sissy. It just means that I'm different,"
Wendell said looking over at his mother for approval. With a nod of her
head she gave him the confidence he needed to continue and said, "I like
to wear nice aprons and help do the housework. And, I want to help Mother
with her hair. I hope I get to wear pretty clothes and I want Mommie to
fix my hair nice and pretty and everyone will know that I really am a
sissy." Very seriously he then said, "See, girls can't be sissies because
they're girls. Only boys can be sissies. Did I understand that right,
Mother?" he asked.
"Perfectly, sweetie, perfectly," Madge said smiling as she noticed the
rose. "Where did that beautiful rose come from?" she asked.
"From the rose bush in the back yard, Mother," Wendell answered.
"Who got it for you, honey?" Madge asked with a puzzled look.
"I cut it myself Mother. I walked around out there early this morning for
quite a while before I picked the one I liked the best. Was that all
right?" Wendell asked.
"Of course baby doll. I'm just surprised you went outside in your nightie
and hair rollers," Madge explained.
Looking at his Mother, Wendell said, "Mother, you told me not to be
ashamed of who I am. Isn't that right Mother?" Then to his aunt he said,
"Mommie and I want everyone to know that I'm a boy that likes doing girl
things. It will be easier and more honest that way. We think that's
better." Then he asked his aunt politely, "May I pour your coffee for you
now, Auntie Arlene?"
Arlene nodded and sat in amazement watching Wendell get the coffee pot
and expertly pour her cup full. He poured slowly but correctly from the
right as his Grandmother had taught him to do.
"Creme or sugar, Auntie Arlene?" the girlish boy asked.
"Thank you, I'll take mine black," Arlene said pointedly.
The two sisters looked at each other across the table and smiled. "This
was too good to be true!" Madge thought.
After their first cup of coffee, the two ladies made a light breakfast
for the trio. Cooking was beyond Wendell's ability although he had
learned a few things during his stay at his Grandmother's. As it turned
out, there wasn't any real cooking to be done for their light summer
breakfast. After breakfast, Wendell insisted on cleaning up the kitchen
and did so.
"What are we going to do now, Mother?" Wendell asked as he put the
finishing touches on the kitchen counters.
"We need to get dressed and there's housework to do. The kitchen looks
great, thanks to you darling. But, we have to vacuum, dust, and make sure
everything is 'just so' before your Grandma arrives. I want you to help
me, Wendell," the boy's Mother said sternly. Then she added patting her
rollers with one hand and pointing at him with an effeminate limp wrist
with the other, "And then, we have to take our hair down and get it
styled nice and pretty."
Wendell felt a twinge in his little manhood when his Mother said ''styled
nice and pretty". He didn't want to take the rollers out but he couldn't
wait for his mother to fix his hair. "I'm confused," he thought.
"Mother, I thought about what you said last night about what to wear
today. I don't have anything to wear except my regular clothes. I don't
know what to do. Can you help me?" he asked.
"Sure, honey doll. Let's go see what we can find. Where's your Auntie
Arlene?" Madge asked.
"I don't know, Mother. HI think she left. Is her car gone?" Wendell said.
"She wouldn't leave without telling me." She looked out the kitchen
window to the driveway and said, "Well, she is gone. But, you know,
that's good. I wanted to talk to you about a couple of things. Let's sit
in the living room," Madge suggested as she took his hand and led him to
the living room couch.
"Wendell, I don't know where this is all going but I want to tell you
again that you can go back to being the 'old' Wendell any time you want.
I love you because you are you and for no other reason. If you want to
dress pretty and have your hair done just once in a while, that's O.K.
too. Don't get me wrong, I loved doing your hair last night and I know
you liked it too. And, I hope to do it again for you really soon. But,
this talk isn't about me. This talk is about you and I want to make sure
you are happy." Wendell tried to say something but his mother stopped
"Please let me finish and then I'll listen to you all day, honey. You
seem to have some kind of inner need do things for me and that pleases
me. I really want you to do some of the housework and help me fix my
hair. And, I loved having the kitchen cleaned up and that you made my
coffee for me.
If you are going to continue down this feminine path that we have
started, there are a couple of things that I think would help you stay in
the right frame of mind," Madge said with butterflies in her stomach.
"Well, first of all, you know that when boys use the bathroom, they stand
up to do their quick business. It can be a little messy and, if you think
about it, you're not like most of the other boys. To make you feel more
feminine, I think it would make you feel better if you sit down to go
potty from now on," Madge said as she blushed.
"I do that already Mommie so my bathroom is really clean now. Grandma
made me go that way at her house. When I came home it was too hard to
remember what I was supposed to do here or at Grandma's so I sit down all
of the time now. I like it better that way and when I finish, I wipe
myself with a tissue, too!" he said proudly.
"That's very good, Wendell. I'm glad that subject is out of the way. And
that's other thing. Your name doesn't fit the way you look right now. You
should face the fact that you make a very pretty looking young girl,
especially with your hair up in rollers like that. Around the house, I
would like to start calling you 'Wendy' when you are showing your
feminine side. Is that all right with you sweetie?"
"Mother, I would love that," Wendy said.
"That's wonderful, Wendy. God, that's sounds so good when I say it. I
don't want to confuse you but when we go to a public place like the mall
or my beauty college, I will call you 'Wendell'. Do you know why?" Madge
"Because we want everyone to know that I'm a boy, Mommie?" he replied
with a question in his voice.
"That's right. Especially at the beginning of all of this, I want to be
sure that you, my son Wendell, are completely comfortable about what you
are and who you are. I don't want you to ever be embarrassed regarding
what you may be wearing or how you have your hair styled. Down the road,
well, ... we'll see what happens."
"Is that all, Mommie? We have housework to do and my clothes to figure
out," Wendell suggested.
Arlene came through the front door and laid down her fanny pack. She
apparently went shopping because she had two plastic bags in her hand.
"Where'd you rush off to without saying a word?" Madge asked her sister.
"Just went out to pick up a few things. I overheard you and Wendell
talking after breakfast. Here sweetie, these are for you," Arlene said as
she handed the large plastic bags to her nephew.
"They are presents for you. I didn't have time to get them wrapped. Just
look in the bags honey," Arlene said.
Wendell opened the first bag and looked down to see pastel colors of
pink, peach, yellow, and green.
"What are ... " he started to ask.
"New clothes. I'm your Godmother and I wanted you to have a few new
things. Just take them out and take a look," Arlene said.
"Mother, look!" Wendy said with great joy. "Auntie Arlene bought panties
for me! My own panties! Three pair! And there are some new shirts!" Wendy
looked in the second bag and found shorts and socks. "For me! Auntie
Arlene, thank you so, so much!" Wendy said as he pulled the things out of
the bag with all of the excitement he could muster.
Madge looked on disbelieving the scene before her.
Arlene looked at her sister. "Sorry hon, but I had to call my sweetie and
wanted a little privacy. I knew Wendell would need a few things to get
started so I went to the Walmart down the highway. I knew you probably
would have wanted to buy him his first girlie things but with Mom coming
and housework and both of your hair to do, I wanted to help out. You're
not mad are you?" Arlene asked.
"No, no, not mad just surprised. There's so much love in this house right
now I could just cry," Madge said, then teared up and started to happily
weep in that wonderfully girlish sort of way.
"I need a Kleenex," Madge said as she stood up and headed to the
Wendy got up and gave his aunt a hug. He kissed her on the cheek and
thanked her again.
"Don't get sloppy with me now. I only bought you some new clothes,"
Arlene said kidding her nephew as she warmly hugged and kissed her
nephew. "Wendell, why don't you try on your new things?" Arlene asked.
"Auntie Arlene, my name is Wendy now. At least around the house it is.
I'd like it if you called me that if you want to," Wendy offered. "I
think after our housework I'll take a bath and get ready for Grandma. I
can't wait to wear my new clothes but it won't be too long."
"I like that name, honey. It's sweet. You remind me of Wendy in 'Peter
Pan'. You know she started out with hair exactly the same color as yours
when the Disney book came out and later on ended up a blonde. Go figure-
Hollywood. Please promise me that you will never do that to your hair.
The gorgeous color of your auburn hair with that little naturally gold
highlight in it is to die for. Oh, Wendy, I want you to ask your Mother
something when she comes back!" Arlene exclaimed.
"What is it Auntie Arlene, please tell me," Wendy said.
"I know your Mother's hair as well as anybody but her. It holds a set
really well, and her hair has been up in those rollers for about fourteen
hours. Even as long as her hair is, with that setting lotion, she's going
to need a little time for her hair to relax or she'll look like a bubble
head when your Grandmother gets here. Why don't you ask her nicely if you
can take her rollers out for her?" Arlene suggested.
"Oh Auntie Arlene, I'd love to! Do you think she will let me?" he asked.
"She let you roll it up for her didn't she? I'll bet she'd love to have
you take it down for her. Here she comes. Now ask her nicely," Arlene
"Mother, is it time to take your rollers out? If it is, can I ask a favor
of you? Would you let me take your hair down from the curlers? Please,
Mother, may I?" Wendy said with all of the sweetness that he had to give.
"What time is it? Oh no! My hair had been set for fourteen hours. Wendy,
thank you so, so much for reminding me. You truly are a little doll. I'll
get my curler basket," Madge said.
"Mother, please, let me get it. You know I want to," Wendy offered.
"Of course, you're right. I really need some time to get used to the new
Wendy. Wendy, will you bring my curler basket and take my hair down
please," Madge said with a mock authority.
"Yes, Mother, I'll be right back," Wendy said smiling as he scurried off.
When Wendy left the room, Arlene went to her sister for a little private
'Well, how's it going Sis?" Arlene asked.
"You were right. My thirteen year old boy sure is a sissy. And, he just
loves doing things for me. What am I going to do? This is nice but it's a
little weird," Madge said.
"Go with the flow, Madge. Just go with the flow. You're not doing
anything wrong," Arlene said.
Wendy came back into the room with his Mother's curler basket and brush
from her dresser. "Where would you like to sit while I take your hair
"I'll sit at the dining room table, darling. It's much nicer in there.
Let's open some of these windows and drapes and let some fresh air in
here," Madge suggested.
Madge sat down, took her scarf off and waited but Wendy was unsure what
to do. He knew he had to take his Mother's hair net off but she had put
it on. Arlene had opened the window and drapes letting in the fresh air.
It also opened the inside of the house to possible view from the outside
and Wendy didn't care. Arlene came into the dining room and Wendy looked
at his aunt for help.
"Here honey, this is easy. You did the hard part last night. Look here
under this bottom roller. This is where your Mom gathered the extra hair
net and secured it with a Bobbie pin. You probably have one just like it.
Reach under there with your fingers until you feel the Bobbie pin and
ever so slowly pull it out," Arlene said helpfully.
"Very good. I couldn't be that delicate when I was your age. Explains why
I'm a lawyer now. Because of the bristles in the brush rollers, they can
snag when taking the hair net off. So, you have to be very careful. If it
snags, then move the net a little bit to one side or the other until it's
free," Arlene said as Wendy performed this delicate task.
"Another job well done, Wendy! Before you take your Mother's rollers out,
I think we should get a picture. I brought my camera in so we can get a
picture of Miss Wendy and her first hair setting job.
Look here and both of you smile nice, now (flash). Oh that's cute. And
you both have such happy smiles on your faces. Now, one more picture for
fun. I want you to stand here," Arlene said positioning Wendy behind his
mother. "Put one hand here and one hand here," she said putting Wendy's
hands on each side of his mother's curlers. "Now, look over here to the
side at the camera and lean over and give your mother a nice kiss right
here on this curler," Arlene directed as she took a step back and another
picture. Arlene laughed and said, "Well that's about the most girlish
thing I've ever seen- a pretty boy kissing his mother's hair rollers."
With his hair up in rollers and that dress-looking apron around him and
the bright flower print peach scarf around his head he couldn't have
looked more the sissy. Arlene showed her sister the picture she had just
taken in the view window of her digital camera and Madge's reaction was
to flush red, shake her head a little bit and have her womanhood throb.
What was she thinking!
Madge got a hold of herself and took over Wendy's instruction. "Now,
Wendy, start at the bottom and take the pick out of one of the bottom
rollers. Slowly unwind the hair until it's free from the roller. That's
good, honey. You know I love having my hair set but this part feels good
too! Now unwind the one next to it either left or right. It's easier if
you work around your Mommies set and work your way up unrolling her hair.
There's less chance of tangles that way."
Madge could not see the look on Wendy's face but he certainly was in a
world that included only he and his mother's hair. He didn't speak but
worked at his task loving every second. The fresh scent of his Mother's
hair as it was being unwound from each roller was stronger than he had
ever encountered. It was a wonderful perfume to his senses and his
favorite aroma in the whole world. The feel of the well formed curls,
stiff from the setting lotion, tickled his hands constantly as he undid
the rollers in his Mother's hair.
And oh, the sight of those luscious curls. Aunt Arlene was snapping a few
more pictures and Wendy didn't even notice. The way his Mother's rich
long curls looked as they sprang loosely back toward her shoulders and
head was a sight so beautiful that he could hardly bare it.
Wendy had gathered his mother's hair loosely in his hands and said as
proudly as he had ever said anything in his life exclaimed, "Look what I
He held one particular barrel of a curl that was particularly formed in
his delicate hand. It originated in the back of the middle of his
Mother's head and when he had released it from the roller, from his view
it had sprung back to the form of the roller in almost slow motion. He
leaned over and put his cute little turned up nose into it.
"Mommie, your hair smells ever so good!" Wendy beamed.
When most of Madge's curls started to loosen due to the sheer length and
weight and volume of her hair, the curls started to naturally relax into
long vertical ringlets. When she moved her head slightly, the way they
bounced reminded him of Shelly's ringlets but they were on a much greater
scale and he had created them. "Oh, Shelly's has ringlets but nothing
like this," he thought.
Wendy was taking the last roller out and he felt more proud than he ever
had in his life. He was good at video games but the creation before him
was real. He loved the fact that his Mother's hair consumed most of his
senses, it was so profoundly beautiful, and, most of all, that he done it
for his mother.
"You rollers are all out, Mother," Wendy almost sadly said. "Now what do
I do?" he asked.
"My hair is stiff from the perfect roller set you gave me. What would
feel so good is if you would give me a little head massage to help break
the set before we try to brush it," Madge replied
"How do I do that, Mother," he asked looking forward to whatever the next
step may be.
"Just put your finger into my curls and massage my scalp gently. Rub my
scalp in little circular motion like you did when you shampooed my hair,
honey. Your arms aren't very long so you'll have to get close to the back
of the chair. That's it, hmmm, oh God that feels so good. Try to run your
fingers through my hair to loosen the set, Wendy. Be gentle or you'll
pull Mommie's hair."
He started to massage his Mother's scalp as instructed and as he did an
even stronger scent from his Mother's hair reached his nose. He now had
his hands buried deep into his Mother's curls doing his best to do
something he had never done before.
This was just too much for the prepubescent boy's psyche to handle and
all of the sudden is hands shook almost violently and he stopped his
"What's the matter, sweetie? Are you all right? His mother asked.
"Uh, I, ... uh, need to go to the bathroom," he stammered.
"Just take out the last rollers, then you can go," his Mother said.
"I have to go now, Mommie," he said. "I ... I ... I think I wet myself,"
Madge stood up and said, "Let me help you honey. Let's see what happened
to Mommie's pretty boy."
Madge took Wendy upstairs to the master bedroom suite and closed the
door. She led him into the master bathroom and, only then realized that
he must be uncomfortable and probably a little bit warm with all of the
clothes he had on although she never heard a word of complaint from him
regarding his discomfort.
"Let's get this apron off of you first," she said untying the bow and
helping him off with it. "There, now let's get your nightie off, Wendy,"
and she pulled the nightshirt up from the hem to his waist and over his
scarf and head of rollers. His torso and legs were now bare and he
trembled as the cool air hit his slender body.
She knelt down and looked for a yellow stain on the front of his panties
but found none. "Honey I don't see anything to show that you peed
yourself. I don't see how you could since you haven't done that since you
were very little. Here, let's get your panties down, honey, so we can see
what happened," she said carefully lowering the control panty that he had
worn all night.
As soon as the panty was down around his knees Madge could see Wendy's
little penis and she knew what had happened as there was a little drop of
clear sticky fluid at the end of his boyish member.
"Oh, Wendy, you wet your panties a little bit but not with pee. I think
you had an emission. Has that ever happened before?" she asked.
"I don't know what that is Mommie.
"It's when this kind of clear sticky fluid involuntarily comes out of
your little penis, honey. Did this ever happen before?" Madge asked.
"One time a couple of months ago I woke up in the morning and the inside
of my underwear was sticky. It scared me and I was too scared to say
anything. It only happened once, Mommie," Wendell said. "Is there
something wrong with me Mommie?"
"No honey, you're just growing up. Don't worry. In fact, absolutely don't
worry. Look at me Wendy." Madge sat down on a step of the large oval
elevated tub in her master bath. Wendy was standing right in front of
her. "Look me in the eye Wendy. Do you believe I love you more than
anything in the world?" Madge asked her prissy boy.
"Yes, Mother, I do," Wendell replied.
"If there was something wrong with you, don't you think we'd be on our
way to the doctor right this second?" Madge reasoned. "So, don't worry
about it. I'll explain it all to you later. Promise me you won't worry
about it," she said with concern.
"I won't Mommie, I promise," Wendy said softly.
'I think it's time to get you into the tub. How about another nice bubble
bath in Mommie's big bath tub? Would you like that?" Madge asked. "I want
to have time to do a little housework and fix your hair before Grandma
comes," Madge said and she knelt down to help Wendy get his panties all
of the way off. He steadied himself by putting his hands on his Mother's
shoulders and the caress of her hair made him feel so much better.
So much so, that while he was standing in front of her, with her head in
a position that he could look down at her massive curls, his little thing
was jerking at an attempt to become erect. Madge was looking straight at
his little boyhood and she smiled thinking about how much he must love
her hair. Wendy was embarrassed at all of this and tried to hurry out of
his panties. Madge thought it was the cutest thing she had ever seen.
As the tub filled with bubbles, Madge thought about how she wanted Wendy
to help her with the housework but he was in a pretty fragile state right
now and there would be plenty of housework to do in the future. The best
thing for him to do would be for her to pamper him a little and get him
dressed for Grandma's visit.
By the time Wendy got out of the tub and was dried and powdered, his Aunt
Arlene had brought his new clothes up to his mother's room. They were
neatly laid out on her king size bed half covering it. There was a box
there that he hadn't seen before and another small package that Wendy
couldn't make out.
Madge and Wendy came out of the bathroom and Madge said, "Wendy, this is
an important moment. You know those clothes on the bed are girls clothes.
We've had two conversations about what is best for you and what you want.
I worry that you are doing this because you think it pleases me. I want
to be sure that it is what you want and it pleases you. If you are not
comfortable, I do not want you to wear these clothes."
"Mother will you please help me put my panties on, I'm cold," Wendell
said a little impatiently.
"What color panties do you want to wear today, Wendy?" Madge asked
"I want the green panties and the matching green top and the white
shorts. Grandma's favorite color is green- like her garden," Wendy
"I don't know if you are the sweetest child in this world, Wendy, but if
you're not, you must be close," Madge said with a lump in her throat. She
picked up the pale green panties and noticed the band of lace around the
waist band and pretty eyelet trim around the leg openings and knelt down
to help Wendy step into his panties. Wendy looked down at his mother's
hair dancing about her head as she helped him and his little penis
started again to stir a little. First one leg and then the other went
into the leg holes. Madge pulled the panties up to his waist and gave him
a big hug. Wendy was wearing his first pair of his own panties and they
both enjoyed this tender moment.
Next came his top and his white shorts. They were quite plain, actually
and went on quickly.
After Wendy was dressed in his new clothes, Madge had him sit on the bed
to put his socks on. They could only be described as juvenile because
they were trimmed in pink lace. Without a word said between them, Madge
slipped the socks onto Wendy's feet and folded the tops down showing off
"Here Wendy. Your Auntie bought these for you too. Open the box honey,"
Madge told him.
Wendy opened the box and he gasped then smiled. Inside the box was a pair
of black patent leather Mary Jane shoes. He had seen the girls wear them
many, many times as he was growing up and longed to wear them and now
there was a pair of his own sitting right in his lap. "My very own black
shiny shoes!" he cried not knowing they were called 'Mary Janes'.
"Mommie, these shoes are so pretty. I've wanted to wear shoes like this
ever since ... since ... I can remember." Madge helped Wendy on with his
shoes and they headed downstairs.
At the top of the stairs, Wendy hesitated and Madge warned him, "Be
careful going down the stairs honey. Your new shoes new and they are
slippery and I don't want you to fall." Warned the boy's mother. "Hold
onto the rail and go down slowly."
Wendy stood at the top of the stairs as if his feet were glued to the
"What's wrong honey? Are you O.K. Do you want to go to your room and
change?" Madge fearfully said. He did look so cute- especially since he
was still wearing the flowery scarf around his neat roller set.
"I'm all right Mother. I want to go down and get ready for Grandma. What
did the spaceman say years ago? 'One giant step or something like that'
," as he took the first step down the stairs.
Madge smiled at his 'one step' statement thinking it was a giant step for
her little boy. She closely watched her curler headed son taking his
cautious steps in his new shoes down the stairs. "Would she ever get to
see him go slowly down those same steps in heels and a prom dress?" she
thought. "God, I pray so," Madge said to herself.
At the bottom of the stairs, Arlene greeted them.
"Don't you look the picture Wendy. Everything fit all right?" the boy's
"Just perfect Auntie Arlene. Thank you so much," he said.
"Come sit here Wendy. It's time for me to do your hair. And then later,
you are going to brush mine and help me style it," Madge said to her son.
Madge started to take the scarf from Wendy's hair and Arlene went to get
the camera. Madge was experienced of course and quickly Wendy was sitting
there as still as could be with his hair net off and his rollers exposed
for all to clearly see. He didn't want his mother to take his rollers out
yet he wanted her to fix his hair. "Mother ... before you take my curlers
out, will you promise me ... " he tried to ask but couldn't.
Understanding his concern, his mother comforted, "Honey, dear, I thought
we were beyond that. You can have your hair set again any time you want.
We can roll it up again tonight if you want to. Remember what I have
said. I'll curl your hair and put it up in a fancy up-do like you were
going to go to the prom if you want me to. Now shush while I take out
your rollers," Madge said a little impatiently. She thought she may have
been a little abrupt and leaned down to kiss his cheek. "My little
princess," she said as she kissed him tenderly.
Interrupting the moment was the ring of Arlene's cell phone. She took the
call and left the room.
Wendy relaxed as he relished in the feel of his mother removing the
curlers from his hair. While having his hair set was incredibly
satisfying, his hair was now free of the curlers that had been in his
hair for so many hours. For now, he loved the feeling of freedom his hair
Madge looked down at her son's now gorgeously curled hair. It was darker
in color than normal because of the setting lotion. This was a special
moment for her. Madge had so long wanted to set and style her son's
girlishly long hair. How ironic it was. She wanted to do his hair for him
and he wanted his mother to do it for him. And now they were a few short
brush strokes away from a pretty girlish style.
"First honey, I want you to see what your hair looks like. Here's the
mirror," Madge said handing it to him. "Now reach up and feel your hair.
Doesn't it feel just yummy! Don't you love the stiffness of the curls?
Your hair looks the way mine must have when you took my rollers out. Now
I'm going to give your head a little massage and run my fingers through
your hair to break the set just like you did for me," Madge explained.
"O.K. Mommie?" Wendy said with a little trepidation in his voice. He
wondered if his mother would get as excited as he did when he did it for
"Don't worry, sweetie, I'm just going to break down the stiffness of your
hair. I'll try not to pull it," Madge explained.
Madge ran her fingers through Wendy's hair trying relaxing the stiffness
of his roller set hair. "His hair is so thick," she thought. "When he
grows up it will be just like his Mommie's."
Madge then picked out her best wide toothed brush and gently began to run
it through Wendy's curls. After a few brush strokes, Wendy said softly,
"Mother, that feels so, so good. Mother, I think, I think, I'm ... I
think ... I'm going to cry." And he sniffled some gentle tears of joy
"There, there, honey. You're just experiencing part of the joy of being a
girl," said and, he is such a girl at heart, she thought to herself.
Madge put the brush down and knelt by her son comforting him. "Wendy,
Wendy we're going to have many, many more times like this. Don't you
worry my sweet boy. Wendy and his Mommie are going to have lots and lots
of happy times doing each other's hair. Tonight I think I may need to
have my hair set again. What do you think?" she asked smiling at him and
already knowing the answer.
Madge was confident that Wendy was calm enough now that she could finish
styling his hair. She brushed and back brushed his hair until she was
able to style it into a very girlish bouffant flip. She thought the style
a little outdated but so very cute. After all, it was the same style she
wore as a girl. His hair needed a little trim because she could tell that
the flip of his hairstyle wasn't quite even. She would take care of that
soon. She also thought that this style would need some nice bangs but she
and Wendy would decide that together.
"There honey, do you want to see your finished hairdo?" his mother asked.
"Oh yes Mother, yes. Please hurry! Is it pretty?" he asked.
"Very pretty Wendy. You're the prettiest girl in the room," the proud
mother said reaching for the hand mirror.
Wendy looked in the hand mirror and beamed, "Oh Mommie. My hair is
pretty! Thank you ever so much!" He reached up to touch his hair and did
so very delicately. "Is this my hair Mommie? Really and truly?" he
"That's your hair growing out of your head, Wendy. Shampooed, set, and
styled. That will be $25 please!" Wendy's mother joked.
"One more thing. Grab the mirror and let's go to the bathroom. I want you
to see the back."
"Just a minute, let's bring these with us," Madge said picking up the
package of barrettes that Arlene had bought with the other things.
In the bathroom mirror, Wendy saw himself for the first time all dressed
and with a pretty new hairstyle. He just smiled at himself as he enjoyed
"Do I look all right, Mother?" he asked.
"You are a living doll, Wendy. There's just one more little thing. Your
Auntie bought these barrettes for you. I want you to pick one that goes
with your outfit, honey. We're going to put it in your hair right here,"
Madge said pointing to a place above his right ear.
"Well, Mother, I think that I would like to choose this one. It has a
little green in it and I think it matches my top. Is that a good choice?"
"That one will be perfect, Wendy. Let me put it in your hair for you,"
Madge slid the barrette into her son's darling hairdo and fastened it in
She leaned over so that her head was on Wendy's shoulder and they both
looked into the mirror in the bathroom.
"What a pretty picture," they both thought.
To be continued in Part II -
Grandma comes to visit ...