Bobby Thompson was 14 years old. He and his Mother had lived alone
together ever since Bobby's father died when Bobby was 2 years old. Bobby's
mother had a good job and soon she was promoted, but with the promotion she
was required to relocate to another part of the country. The school year was
almost over so they stayed until summer vacation started. The company that
Mrs. Thompson worked for (because she was willing to relocate) bought her a
large house at the end of a dead-end street with only one other house on it.
The job kept her very busy so she unable to spend the time that she wanted to
with Bobby. Even simple things like taking Bobby out to get a haircut were
becoming difficult, and as a result his hair had grown down well below his
ears, but the job paid well and she was able to supply a good standard of
living for herself and Bobby. Before her promotion she worked only during the
week when Bobby was at school and was able to put him in daycare in the
afternoons and during vacations. But the new job required a lot of overtime
including Saturdays. Bobby's Mother would not leave Bobby home alone all day,
every day so she found a baby-sitter stay with him during the day while she
was at work.
The baby-sitter's name was Sally. She was 18 years old and studying to
become a model. She was sometimes able to model for a local department store
whenever they had fashion shows. Bobby thought that she was very attractive,
but it seemed funny to him that she was so concerned with her looks. Every
few minutes she was either fixing her hair or redoing her makeup. She also
told Bobby that she liked his hair long, that it made him look cute, and that
he shouldn't get it
cut. It was the third time Sally was baby-sitting Bobby. They were
both sitting down in the living room. Sally was wearing a pair of tight gray
leather pants, a red satin blouse, and high heeled boots that Bobby thought
made her look absolutely beautiful. As usual she was putting on some lipstick
and Bobby was looking at her with a great deal of interest. She looked over
at Bobby and said, "Bobby: Do you think I'm pretty?", Yes.", Bobby replied.
"Do you like pretty?", Sally asked. "Uh, sure, I guess so.", Bobby answered.
"Then come here.", she said. Bobby got up from his chair and started to walk
over to Sally. As he was walking over to her, she held the lipstick up and
said, "I'm going to make you look pretty too." When Bobby saw that Sally was
going to put lipstick on him he jumped back and said, "No!, I don't want to".
"Come on.", Sally said "you'd look cute with lipstick on." "No!.", Bobby
repeated. There was silence for a few seconds then Sally looked over at Bobby
with a smile and said, "Bobby, I want to see you with lipstick on. Now come
here." "But I don't want to.", Bobby replied. "If you won't let me put it on
you I am going to make you wear it". "No!", Bobby shouted.
With that she quickly cranked down the lipstick, put the cap back on, put
it in her makeup bag and started to walk toward Bobby. Bobby started run out
of the room, but Sally was just to quick for him. She grabbed him by the arm
and got him down on the floor and sat on him, holding his arms down with her
knees. Bobby lay there struggling, trying to wiggle loose, but try as he may
he was unable to escape. Sally looked down at Bobby sighing and shaking her
head, she said to him, "Oh Bobby, you should have let me put the lipstick on
you. Because now that you have disobeyed me, as a punishment, I'm just going
to have to you wear makeup too, and I afraid I'm also going to have to put
eyeshadow and eye liner on you. Oh yes, I'm also going to have to see what I
can do with your hair". She took a curling iron out of her bag and plugged it
into a near by socket so that it would heat up. Holding Bobby's head between
her knees; she took some liquid makeup out of her makeup bag and started to
apply it to Bobby's face. As she was putting the makeup on him she could feel
Bobby trying to wiggle his head loose from between her legs but as she
continued to apply the makeup she felt Bobby start to relax and gradually stop
struggling altogether. Sally decided to see what would happen if she spread
her knees apart so she wasn't holding Bobby's head any more. Bobby just lay
there as if consenting to let Sally do what she wanted.
Sally smiled and said, "That's it Honey, hold real still now so Sally can
make you look really pretty." With that she finished putting the liquid
makeup on Bobby. Next she put blush on each of Bobby's Cheeks. Then she held
his eyelids closed one at a time so that she could put bright blue eye shadow
on each of Bobby's eyes. Next she outlined his eyes and darkened his eyebrows
with eye liner. Finally she took out some mascara and applied it to each of
Bobby's eyelashes. "You look almost like a girl.", she laughed. "Now, here's
what I wanted to put on you all along". Sally took the lipstick out of her
makeup bag, removed the cover, and cranked it up. Holding the open lipstick
in front of Bobby, she said, "Now tighten your lips". Bobby did not do
anything. "Come on, be a good little girl for Sally.", she said, holding the
lipstick in front of him. Bobby hesitated for a minute but finally gave up.
Bobby tightened his lips and Sally slowly brought the tube of Bright red
lipstick, to Bobby's lips and started putting it on him. "Oh pretty!", said
Sally with a great deal of Delight as she was applying the lipstick to Bobby's
lips. She took her time putting the lipstick on Bobby. When Sally had
finished Bobby had very thick coat of the bright red lipstick and she had
brought it out just past the edge of Bobby's lips all the way around in order
to give a more sexy shape his mouth.
After that she had Bobby sit up, picked up the curling iron which had
heated up by then and holding it in her hand, she said, "Now I'm going to curl
your hair and when I'm done you're going to look just like Shirley Temple".
Because Bobby's hair was fairly long, she was able to take small pieces of
Bobby's hair in the curling iron and make little curls. She continued this
until all of Bobby's hair was a mass of tight curls. When she had finished
with the curling iron she stood up and walked over to her pocketbook and took
something out. "I always take a hair ribbon with me in case I want to tie my
hair back", Sally said. Sally was holding a large red hair ribbon in her
hand. She walked over to Bobby, Took on one of his curls and tied the ribbon
to it. Then she tied a large bow in the ribbon and pinned it flat with bobby
pins.
When she had finished with Bobby's hair Sally helped Bobby up by the hand
and said "You look just like a little girl. I can't get over it. Come on I
want you to see!". Sally took Bobby by the hand and led him upstairs to his
Mother's bedroom, walked over to a full length mirror and placed him in front
of it. "There, this is what happens to you when you are bad and disobey me",
said Sally. Bobby looked at himself. He could not believe what he saw. It
was his face all right but his skin seemed to have a soft glow about it. His
cheeks were a soft pink and his eyes were a pale blue. His eye lashes seemed
almost twice as long as they normally were. The way the eye liner contrasted
the soft color of his eye shadow made his eyes stand out to give his face a
more feminine look. His lips glistened from the heavy coat of bright red
lipstick and Sally had outlined his lips perfectly. His hair was a mass of
tight little curls and Sally had tied the ribbon in his hair so that was just
cocked over to his left side just a little bit and she pinned it in place so
that it would not move. After about a full minute he looked up at Sally and
asked, "Did you do this to me because I did not do as I was told?". "Yes I
did.", Sally answered. Bobby looked back at himself in the mirror. "Am I
pretty Sally?", he asked. "You sure are!", Sally replied almost crying as she
saw the expression on his face. "Do I look like a girl?", Bobby inquired.
"Yes, very much so.", said Sally. "And this is what you are going to do to me
every time I'm bad?", Bobby asked. "I think that's a very good idea.", she
replied.
Bobby's Mother was not expected home for another three hours so Sally
decided that Bobby would have to stay like that for a while. They went back
into the living room and sat down. Sally asked Bobby if he would like to look
at some fashion magazines that she had brought over. "OK.", agreed Bobby. As
they were thumbing through the pages Bobby would point out dresses that he
thought Sally would look good in and she discovered that Bobby had very good
taste. They came across a picture of a girl in a yellow short pleated skirt
with a pink long sleeved turtle necked jersey. "Bobby, That would be a good
outfit to put on a naughty little boy like you!", Sally said with great
excitement. Bobby turned bright red at the thought of wearing woman's
clothes.
After they finished looking at the magazines Sally brought Bobby into the
bathroom, washed the makeup off his face, untied the ribbon from his hair, and
used a hot comb to straighten his hair. After Sally had finished she said,
"Bobby, what would you think if I brought over some girls clothes to make you
wear in case you are bad?". Bobby blushed when he heard that. "I don't
know.", he replied. Sally looked at Bobby smiling and tapping the tip of his
nose with her finger as he spoke, "You know what I think, I think you'd like
it. You might even be bad just to get me to dress you up like a girl."
CHAPTER 2
The next Saturday Sally was sitting in the living room when Bobby walked
in. "Sally.", Bobby said hoping Sally meant it when she said she would dress
him up like a girl for being bad. "What?", Sally asked. "I think I've been
bad.", Bobby replied. "What did you do?", Sally asked. "I didn't clean up my
room this morning", Bobby said. Sally looked at Bobby with a big smile. "You
know you are going have to be punished Bobby! Now go over and sit in that
chair so I can make you up.", Sally said with a laugh. Bobby went over and
sat in the chair.
After she finished making Bobby up with the red lipstick, blush, mascara,
Blue eye makeup, and eye liner she brushed his hair back and put a hair band
in it. Then she looked at Bobby and said, "You obviously didn't learn your
lesson last time so I am going to have to make you wear more things.", Sally
said. With that she walked over to her pocketbook and took out a pair of
earrings, bracelet, and necklace. She walked over to Bobby and put one of the
earrings on Bobby's left ear and screwed the post tight. Next she put the
other earring on his right ear. Then she walked around behind Bobby, put the
necklace around his neck and clasped it. "Now hold out your hand so I can put
the bracelet on you.", Sally ordered Bobby. Bobby held out his wrist and she
put the bracelet on him. "You were a bad boy Bobby, and you are going to have
to stay like this until you have learned your lesson!", she said smiling.
After a number of weeks Bobby's hair had grown down to his shoulders and
one afternoon his mother said that she would have Sally take him out to get a
haircut but he told her that he liked having his hair long, thinking to
himself that Sally would not be able to make him look like a girl if his hair
were short. His mother thought nothing about it and did not make him get one.
Every time Sally came to baby-sit she would bring over something else to
put on Bobby in the event that he was bad and he usually was. One week she
brought her curlers and hair net and because Bobby had forgotten to wash his
hands before lunch she made him sit in a chair while she set his hair. Sally
was very pleased with the hair do that she was able to create.
As the weeks passed Sally taught Bobby how to do things like put on his
own makeup, how to use a curling iron and set his own hair, how to walk in
high heels, how to sit while wearing a skirt or a dress. Bobby seemed to be a
natural at everything she showed him and she could see that he was very eager
to learn. One day while Sally was there baby-sitting, Bobby went into his
mother's bathroom, took her electric shaver and shaved his legs and his
underarms. When he showed Sally she said, "Oh, Bobby what are you going to do
when your mother sees you like that". "I don't know, I just won't let her see
me naked, but don't you think my legs look nice?". Sally looked at Bobby and
said, "Bobby you really like dressing up like a girl, don't you." Without
saying a word, Bobby shook his head yes while blushing. "Well, I really like
showing you how, thanks for being such an eager student, and to show you my
appreciation I'm going to have a special surprise for you tomorrow.", Sally
said smiling.
The next day Sally brought a paper bag with her and after Bobby's mother
left she opened it and took out a pair of panties, a garter belt and a pair of
nylon stockings. "Your legs looked so pretty yesterday after you shaved them
I thought it would be a pity not to put them in stockings.", Sally said with a
smile. She showed Bobby how to put on the stockings without getting a run and
how to get the seem straight in the back. After she got them on Bobby she
said, "They're for you to keep Bobby. I want you find a place to hide them so
your mother won't find them and you can wear them any time you want." "Oh,
thank you!", Bobby said with a great deal of excitement, and hugged Sally.
Bobby wore them all day. Even when his mother came home he was wearing them
under his pants and his socks. That night before he went to bed he hid them
in his bottom bureau draw under some sweaters. A few days later Sally brought
Bobby a pair of large hoop earrings for him to keep and after Bobby had worn
them most of the day he hid them in his bottom draw with his other things.
Bobby practiced everything that Sally had taught him until he was able to
make himself up so that it was almost impossible to tell that he wasn't a real
girl, but he liked it best when Sally dressed him up, and actually Sally
derived a great deal of pleasure from doing it to him.
CHAPTER 3
About 2 weeks later Bobby's mother announced that she had to go on a
business trip for two days so she asked Sally if she would stay at the house
with Bobby while she was gone and Sally agreed. The day before Bobby's mother
was to leave on her trip Sally and Bobby were sitting in the living room,
Sally was playing with Bobby's hair putting little braids in it when she said,
"Bobby, there is a fashion show downtown tomorrow and I am going to get a
chance to model in it. Your going to have to come with me, I hope you don't
mind." "No", Bobby said, "it sounds like fun, and besides I'd like to see you
model."
The next morning Sally got up and made breakfast. They sat down and ate
Breakfast together. When they were finished Sally got her makeup and
everything else she would need at the fashion show together. They got in the
car and headed out.
They arrived at the department store at about 8:30 A.M. Miss Benson who
was directing the fashion show was there and as the girls arrived they started
planning which outfits would be worn by which girl. Miss Benson tried to
match each outfit to a girl that she thought had the look she wanted to go
with it. She got to one outfit, a red satin sleeveless dress that went down
about half way between the hip an the knee. It had a pair of red leather
gloves that went up to the elbow, red paten leather high heels, and a matching
red paten leather handbag.
Miss Benson looked for the girl that she thought had the look she wanted
for this outfit but none of them seemed to have exactly what she was looking
for. Finally she looked over at Bobby and said, "It's too bad I couldn't
dress you up in this. You have the face I'm looking for, for this outfit."
Bobby just sat there and blushed.
Sally walked over to Miss Benson and asked to speak to her alone. She
pulled her aside and whispered in her ear, "you know I've dressed Bobby up
like a girl before, he likes to do it and when you makeup on him he looks
absolutely beautiful. I bet we could convince him to model the red satin
dress for us if we really tried." "We can't have a boy model one of our
dresses and besides he doesn't have any experience modeling.", Miss Benson
replied. "He already knows how to walk in a tight skirt and high heels. All
we have to do is teach him a few turns and I think he'd do fine. We have four
hours to dress him up and teach him the walk.", Sally said. "He'd never agree
to it.", Miss Benson said. "It wouldn't hurt to ask.", Sally replied. "A boy
who's interested in something other than bugs and baseball, how refreshing. I
guess it wouldn't hurt to ask.", Miss Benson said. "Ask him in front of the
other girls. If there supportive I think it will help.", Sally said.
Miss Benson walked over to Bobby and said, "Sally tells me you've dressed
up like a girl before and that you look pretty good. I don't have anyone here
that has the look I'm looking for, for that red satin dress. Would you be
willing to try it on and if you look good enough model it for me?", Miss
Benson asked.
Bobby looked at Miss Benson with shock and fear. "No, I don't think so",
Bobby stammered. When Miss Benson saw the expression on Bobby's face she
said, "I was foolish for asking, I didn't mean to embarrass you." Sally
looked at over at Bobby with disappointment. She had hoped that Bobby
wouldn't have reacted with such fear but forgot about it and continued to
prepare for the fashion show.
A few minutes later another one of the models walked over to Bobby and
said under her breath, "Bobby, if you wanted to try on that red satin outfit
I'd be willing to give you a hand." One of the other models who was standing
close by overheard said out loud, "I'd be willing to help too." Soon Bobby
had about five or six of the girls all standing around him encouraging him to
give it a try. "But Miss Benson is already trying to find someone else to
wear it.", Bobby said." "I'm sure if you went to her and told her that you
had change your mind she'd still let you.", one of the girls said. "Come on
give it a try.", the girls kept saying. Finally Bobby gave up and agreed.
All of the girls standing around him applauded him for his courage. Two of
the girls pulled him up from the sitting position and pushed him in the
direction of Miss Benson.
Bobby walked up to Miss Benson wringing his hands with nervousness.
"Miss Benson.", Bobby stammered. "Yes, what is it Bobby?", Miss Benson asked.
"I--I guess I could try on that dress if you still wanted me to.", Bobby said.
"Are you sure? I don't want you to do anything you don't want to do or are
not ready for.", Miss Benson replied. "The girls said they'd help me get
ready and I guess I'm willing to give it a try.", Bobby said. Miss Benson
looked at Bobby long and hard and said, "Are you sure you want to do this
Bobby?" "I think I'd like to see if I could do it.", Bobby said. "Then go
ahead and we'll see how you do.", Miss Benson replied.
Bobby walked back to the girls who were anxiously awaiting Miss Benson's
decision. "Well, what did she say.", all the girls asked Bobby. "She said to
go ahead.", Bobby replied. The girls were all laughing, jumping, and
clapping. "You know Bobby it will go a lot quicker and we can make you look a
lot better if you let us dress you from the bottom up. you don't mind if we
see you naked do you?", one of the girls asked. "No, I guess not. Bobby
replied. The girls were well stocked for the fashion show and even Miss
Benson had brought extra padding in case one of the girls needed some building
up in the necessary places.
The girls walked over to Bobby and went straight to work. One them bent
down, untied Bobby's sneakers, then removed them. Next she took off both of
Bobby's socks. While she was doing that another girl had him stand up so she
undo his belt and unsnap his pants. After his shoes and socks were off she
pulled his pants down and had him step out of them. Bobby turned red at what
the girls saw next. He had decided that morning that he wanted to ware his
panties. "Well.", the girl said who had taken his pants said smiling, "It
looks as if your more experienced at this than I thought. But they will have
to come off so we can shave you all the way up. No one in the audience would
know if you had any hair there but as one of us girls we know you just
wouldn't feel right." So she took off his panties.
A third girl unbuttoned his shirt, took it off, and then took off his
undershirt. Bobby stood there facing 6 beautiful girls completely naked.
"This shouldn't take long, it looks like he has shaved within the last week.",
one of the girls said. Three of the girls took electric razors and removed
what little stubble from Bobby's body that had grown in the last few
days. Bobby was so nervous that he was shaking all over. "Oh, Bobby this is
going to be so much fun, we just can't wait to see you walk down the runway.",
one of the girls said as she was shaving Bobby. All of the other girls said,
"Yes.", in agreement. When they were done one of the girls took a brand new
pair of red satin panties and held them out for Bobby to step into. "As a
model you get to ware all new clothes. We'll put your others in a locker with
the rest of your things.", she said. Slowly she pulled them up and into
place. Then one of the girls walked over to Bobby with a bottle of nail
polish. "I've got Rose Red nail polish for you Bobby. Your fingers and toes
are going to look so pretty! I know they won't show, but it just makes you
feel much more feminine.", She said. She took off the cover and put a coat of
the bright red polish on each of Bobby's fingers and toes. After the polish
had dried She said, "I think you need another coat Bobby". Bobby, did not say
a word he just looked at his hands and feet and thought how feminine they
looked. The girl applied a second coat of the polish to Bobby's nails. Then
she put a third coat of polish on his fingers and toes and waited for it to
dry. After the final coat had dried Bobby looked down at his feet. The red
on his toenails was the brightest and shiniest red he had ever seen.
While they were waiting for the nail polish to dry the girls collected a
red bra, slip, and red garter belt that matched the panties, a padded girdle,
and a pair of black nylons. One of the girls walked over to Bobby with the
bra and had him put his arms through the straps. Another girl strapped it up
in the back while a third stuffed padding in each cup. Then one of the girls
had Bobby step into the padded girdle. "This will round you out in the hips
to make you look more girlish.", She said. Then pulled it up into place.
After that another one of the girls put the garter belt on him and had him sit
in a chair while she put the nylons on him and clipped them to the garter
belt. "We could have used pantyhose but I think the garter belt and stockings
are much more feminine, much more you, Bobby.", She said as she was clipping
the stockings to the garter belt. After she put the stockings on Bobby, She
had Bobby put on a pair of pink ballet slippers so that he would not damage
the stockings when he walked. When that was done another one of the girls was
waiting with the full slip. She pulled it down over his head and into place.
"Oh Bobby you're looking prettier and prettier with everything we put on
you.", She said. Then two of the girls were standing by with the red satin
dress. They took the dress and put that over his head and pulled it down into
place. Then they had Bobby turn around so that they could zip it up in the
back. The dress was cut to have a close clingy fit and with Bobby wearing the
padded girdle and padded bra and because of the fact that he already had a
very slim waist made the dress fit perfectly. When the dress was on another
of the girls put a long brunette colored wig on Bobby and brushed it into
place. When she had finished Bobby's new hair went down to the middle of his
back.
At this point it was time to start applying Bobby's makeup. One of the
girls picked up a large makeup case. She walked over to Bobby, opened it up,
and took out some makeup base and put a smooth even coat on Bobby's cheeks,
nose, and chin. Next she applied pink blush to each of his cheeks. "Oh,
Bobby you look so beautiful, I just can't get over it.", the girl said to
Bobby as she was applying the blush. After that she put powder on him to
soften the color of the blush. Then she took an eyebrow pencil and outlined
each of Bobby's eyes. Next she put light blue eye makeup on his eyelids and
mascara on his eyelashes. Finally she took some Bright red lipstick that
matched the color of the polish on his toes and fingers, and applied a thick
but even coat to Bobby's lips outlining them perfectly. When she was done
with that she applied a lip gloss to his lips so they would really shine.
As Bobby was having his makeup applied, another one of the girls took the
red leather gloves and had Bobby hold his hands out so that she could put them
on him. "You wouldn't look proper without your jewelry.", One of the girls
said. She went over to her jewelry box, took out a pearl necklace and
matching screw post type pearl earrings, walked over to Bobby, fastened the
necklace around his neck, and put the earrings on his ears. While that was
being done another one of the girls took the ballet slippers off of Bobby and
slipped his feet into the red paten leather high heeled shoes. Finally they
had Bobby stand up, take the purse, and put the strap over his shoulder and
had him bend his elbow and rest his hand on the purse holding the bottom of
the strap. All the girls stood back and looked at there handiwork. One of
the girls spoke up and said, "Wait I have an idea." She got a small red hat
with netting to cover the face, walked over to Bobby, and pinned it to his wig
and pulled the netting down over his face. "There all finished, you
absolutely beautiful, just like a girl.", She said with great delight. All of
the girls agreed and each complemented Bobby on how good he looked. Standing
Bobby in front of a full length mirror that was in the room, they all told
Bobby to look at himself.
Bobby looked at himself with the red paten leather high heels, the red
satin dress, the red leather gloves and purse, the makeup, blush eye shadow
and mascara, the necklace and earrings, and the bright red lipstick. He had
never been fully dressed as girl and it was at this time that the thought of
dressing as a girl all the time first entered his mind. "Now that you look
like a model lets see if we can get you to move like one.", one of the girls
said.
With all of the practicing Bobby had done it only took him about an hour
to master the moves that the girls had shown him. He kept practicing until it
was just about time for him to go out. Miss Benson came over to him and asked
to see if could be convincing enough that no one would know that he was not
only not a girl but also not a model. When Bobby showed her what he could do,
all she could do was look on in amazement. "Bobby, you may be a boy on the
outside, but I think there is a whole lot more girl up here than there is
boy.", she said tapping him on the side of the head.
Finally it was Bobby's turn. Miss Benson announced him. He came out as
she was describing what he was wearing. He walked down the runway, did a few
turns and walked back. All of the other models were peering at him through
the curtain. When he was done and walked back stage all of them were waiting
for him. "That was absolutely fantastic.", they all agreed congratulating
him. Bobby beamed with pride as the girls doted over him and his performance.
Miss Benson stuck her head back stage and said to Bobby, "Don't take the
outfit off, I want to talk to you."
Bobby walked over to Sally and asked, "Sally, did you have anything to do
with Miss Benson asking me to try modeling?" "I might have.", Sally said
smiling. "Thank you.", Bobby said giving Sally a hug.
After the show was over Miss Benson came over to Bobby and said, "You did
better than I ever dreamed any boy could do. even better than some girls I've
had. The rest of the models are being paid for their work today, but I hadn't
planned on you and only enough money was allocated for them." "That's ok.",
Bobby said, "It was worth it just finding out if I could do it." "I don't
intend to let your hard work go unrewarded.", Miss Benson said. "What do you
mean?", Bobby asked. "I told you to leave the outfit on for a reason. It's
worth about one hundred dollars which I think you have earned every penny of.
The outfit is yours if you want.", Miss Benson said. "Yes I do. Thank you
very very much!", Bobby said with a surprised look on his face. "It's my
pleasure.", Miss Benson said.
It was not very difficult for the girls to convince Bobby to leave
everything on for the ride home. When they arrived home and got out of the
car Sally and Bobby noticed that Mrs. Johnson, their next door neighbor was
looking over at them very strangely. "Come on.", Sally said under her breath,
"Don't even acknowledge her." "Do you think she knows it's me?", Bobby asked.
"I hope not Sally replied. After they got inside it was not long before they
forgot all about the incident.
That evening Sally and Bobby were sitting around the house watching TV.
Bobby was still dressed as a girl. Sally got up and left the room. A few
minutes later she returned holding something in her hand. Sally looked at
Bobby and said smiling, "Since you've spent most of the day dressed as a girl,
you might as well go to bed dressed as one. "What?", Bobby replied with
anticipation in his voice. "I think you should ware my pink baby doll nighty
to bed." She held the nighty out for Bobby to take. Bobby reached out and
took it. It was a very frilly outfit, made of satin with chiffon frills all
over the top and the panties that went with it. "Oh, thank you .", Bobby
said. "Leave your makeup, wig and bra on. That way you can look like a girl
all night long."
Bobby went to his bedroom to change. When he got there he carefully
removed his clothes. He hung his dress on a hanger so that it would not
wrinkle and put it in his closet. He draped his panties, slip, stockings, and
garter belt over the back of a chair and placed his high heels on the floor of
his closet. Then he put on the nighty and went downstairs. Sally was waiting
for him in the living room. "Well, what do you think?", Bobby asked. "As
usual, you look absolutely fantastic. Here so your feet don't get cold.",
Sally said handing him a pair of pink ballet slippers to put on his feet.
"Thank you.", Bobby replied, putting the slippers on.
As the evening wore on Bobby grew very tired from his very busy day.
They were sitting on the couch together watching a movie when Sally noticed
that Bobby's eyes kept closing. "Would you like to put your head on my lap?",
Sally asked. Without saying a word Bobby crawled over to Sally, laid down,
and put his head in her lap. By the time the movie was over Bobby was fast
asleep. Sally tried to wake him but when she saw that he was in such a deep
sleep she picked him up, carried him up to his room and put him to bed.
CHAPTER 4
The next morning Sally got up and made breakfast. Shortly afterwards
Bobby got up and came downstairs still wearing the wig, nail polish on his
fingers and toes, makeup, and the baby doll nighty. After they had finished
Sally ask Bobby if he would like to go to the beach after he finished doing
the dishes. "Oh Boy! I sure would!", Bobby exclaimed. He went straight
washing the dishes while Sally went off to get into her bathing suit. When
Bobby finished doing the dishes he went into the bathroom to get changed and
wash off the makeup. By the time he finished Sally was already in her bathing
suit and standing outside the door waiting for him. She was holding another
girls' bathing suit by the straps in one hand and a bathing cap in the other.
When Bobby came out of the bathroom and saw her he just looked at her with a
confused expression. Sally looked at Bobby smiling and said, "After yesterday
you can't go to the beach like that, you have to go dressed as girl."
Bobby felt his heart pounding at the prospect of going out in public
dressed as a girl. "But Sally, that was just for a couple seconds out on a
stage this would be all afternoon, do you think I could really go to the beach
dressed as a girl?", Bobby asked in a nervous tone of voice. "Sure you could,
no one will know, especially with your legs and your underarms shaved like
that.", Sally said. The bathing suit was a yellow one piece with a little
skirt that went all the way around the waist. Sally had even sewn pads into
it so that it would look like Bobby was beginning to develop breasts. The
bathing cap was red with a large yellow flower on one side and a chin strap.
"You are just going to do just fine.", Sally said smiling. Sally walked over
to Bobby, pulled the draw string out of his bathing suit, untied it, and
loosened the waist band. Then she pulled down Bobby's bathing suit and had
him step out of it. Bobby was so nervous that he was shaking all over. "So
far I've been able to make you look like a girl, and if I keep doing it soon
you'll start to feel like a girl, and after that you won't be able to keep
from behaving like one.", Sally said holding Bobby's bathing suit in her hand.
She tossed Bobby's bathing suit onto a nearby chair, picked up the girl's
bathing suit and had Bobby step into it. Then she pulled it up, had Bobby put
his arms through the shoulder straps and pulled them up into place. After She
had put the bathing suit on Bobby she took out a hair brush and brushed all of
his hair up toward the top of his head, gathered it together in a bun, and
pined into place with bobby pins. "You look very pretty already, but you've
been such a good girl, you deserve to look even prettier.", Sally said and she
reached into her makeup bag and pulled out the bright red lipstick and some
matching nail polish. "I'm going to put some lipstick and give you another
coat of nail polish. Oh, and I also want you to ware the pink ballet slippers
too. Sally took the lipstick and put it on Bobby's lips as thickly as she
could, next she put another coat of nail polish on his fingers and toes and
waited for it to dry. Finally she took the ballet slippers and handed them to
Bobby and had him put them on. After she had finished with him Sally told
Bobby to pick up his bathing cap and go and look in the mirror.
Bobby picked up the bathing cap, walked into his mother's bedroom, and
looked at himself in the mirror. "Oh, Sally!", Bobby stammered. he was
stunned at how he looked and could not think of anything else to say. "Ok,
Bobby go get in the car.", Sally told Bobby. "Sally?", Bobby said looking
down at the floor. "What?", Sally replied. "If I said I didn't want to go to
the beach dressed like a girl would that be naughty?", Bobby asked. "Yes, I
guess it would", Sally said. "and would you have to punish me by putting
something else on me?" "Bobby, what are you thinking of?", Sally asked.
"Sally, you've gone to a lot of time and effort to make me look nice, and if I
were so ungrateful that I told you I didn't want to go to the beach dressed as
girl that, that would be shameful on my part and you should punish me by
making me wear perfume.", Bobby said. "I agree!", Sally said. "I don't want
to go to the beach dressed like a girl.", Bobby said under his breath, still
looking at the floor, but smiling. "Bobby Thompson!", Sally said, "You
naughty little thing. Get over here so Sally can put some perfume on you!".
Bobby walked over to Sally. "You'll never learn will you.", Sally said with a
chuckle. She reached into her purse, took out a bottle of perfume, took the
cover off and dabbed Bobby behind each ear and on the back of each of his
legs. Then she said, "Bobby if you keep this up I'm just going to have to
dress you like a girl all the time. Now go out and get in the car!". Without
another word Bobby went out and got in the car.
The ride to the beach was very quiet. Bobby just sat there thinking of
how pretty he looked. When they got there Sally parked the car and she and
Bobby got out. "Don't forget your bathing cap.", Sally said. Bobby opened
the car door, reached in and picked up the bathing cap. Sally started to walk
toward the beach but Bobby just stood there. Sally turned around, took Bobby
by the hand and, led him down to the beach. When they got there they spread
out the blanket and sat down. At first all Bobby did was sit there with his
head resting on his knees, moving his hand through the sand, and looking at
his brightly painted finger and toenails. "Why haven't you gone in the
water?", Sally asked. "I don't know.", Bobby replied. "Put on your bathing
cap, go to the water and get wet.", Sally told him. Bobby picked up his
bathing cap. It was easy to put on because his hair was all pinned up in a
bun. He slowly walked down to the water and went in. After a while Sally
noticed that Bobby was swimming around just like all the other children. In
fact he even played with two other girls who had a beach ball for a few
minutes.
About a half hour later Bobby came back up and sat on the blanket. Bobby
looked over at Sally and said, "Sally I feel so much like a girl I almost
think I'm turning into one.". Sally put her hand on Bobby's knee, looked at
Bobby, and said, "Bobby you're already more of a girl than most females your
age.". At first Bobby had forgotten that he still had his bathing cap on but
because it made him feel so pretty even when he realized it he decided to
leave it on.
After a few minutes Sally looked over at Bobby. "Bobby, you need some
more lipstick. Come over here so I can put it on you.", Sally ordered. She
had Bobby lay down so it would be easier for her to apply the lipstick. She
leaned over Bobby and applied a thick coat of lipstick to Bobby's lips.
When she finished Sally opened her pocketbook and took out a five dollar
bill. "Bobby, take this.", she handed Bobby the money. "I want you to go up
to the gift shop. As soon as you go in the door there is a rack with all sorts
of hair accessories. There is a big yellow bow and I you to buy that and one
of the pocketbooks on the back wall for yourself.", Sally told Bobby. "Oh
Sally, I'd be afraid to go without you.", Bobby said nervously. "Don't worry
you'll be fine. Just take off you're bathing cap, most girls don't like to
ware them." "OK.", Bobby said assured by Sally's confidence in him. He took
off the bathing cap and walked on up the beach.
Bobby returned a few minutes later with a pink shiny shoulder bag and his
hair ribbon. "Come here Bobby and let me see how you made out.", said Sally.
Bobby came over and handed the bow to Sally. "Please Sally, put the bow in my
hair.", Bobby asked. "Sure.", Sally replied, "Here, sit down." Bobby sat
down and Sally put the bow in Bobby's hair right in front of the bun.
Sally and Bobby spent the rest of the afternoon there. About fifteen
minutes before it was time to go Sally had Bobby take the bow out of his hair,
put his bathing cap back on and go in for one last swim.
When Bobby came back from swimming Sally had him take off his bathing
cap, so she could put the bow back in his hair, and gather up his pocketbook
and bathing cap. They walked back to the car and went home. when they got
home Sally had Bobby put on a pair of pink shorts, his bra with the padding, a
sleeveless blouse, and the pair of pink ballet slippers. Sally noticed
something on Bobby's shoulders. "Come here Bobby.", she said. Bobby walked
over to Sally. She pulled back the collar of the blouse and looked at Bobby's
back. "Uh-ho", she said. "What's wrong?", Bobby asked. "You got a little
bit of a suntan today and you're all white where the girl's bathing suit was.
Now you really better not let your mother see you naked".
The next morning Sally dressed Bobby up in a yellow mini skirt, a tank
top (Which she put a pair of crumpled up stockings to give him a bust line),
Put lipstick, eye makeup, eye liner, and blush. Then she had him put on a
pair of red, open toed high heeled shoes. She said that way she could see the
nail polish on his toes as well as the polish on his fingers. Finally she did
up Bobby's hair in a pony tail and tied it in place with a pink hair ribbon.
She had Bobby stay dressed like that until about five o'clock, but then had
him wash off the makeup, remove the nail polish, and get dressed in his
regular clothes because his mother was expected home soon. Sally brushed
Bobby's hair out. Then Bobby went into the bathroom, washed his makeup off,
and removed the nail polish from his fingers. When he was done they took all
the girls' things that had gotten and put them out in Sally's car
About an hour later Bobby's mother arrived home. She thanked Sally for
the last two days and sent her home. Bobby's mother asked him what he had
done while she was gone. Bobby told her that they had gone to the beach the
day before but of told her nothing of how he was dressed or about his
appearance in the fashion show. "That's good.", his mother said, "I'm glad
you had fun."
CHAPTER 5
That evening after Bobby had gone to bed his mother received a phone
call. It was there next door neighbor Mrs. Johnson. She told her about the
two girls she had seen getting out of the car and how one girl looked like
Sally, Bobby's baby-sitter, but the other girl looked very much like Bobby. I
fact she thought it was Bobby in girl's clothes. "I thought I'd better call
you tonight because my husband and I are moving away tomorrow and if I didn't
tell you tonight I wouldn't be able to at all and I thought you should know."
Bobby's mother thanked her very much for calling and hung up.
The next morning Sally showed up to baby-sit. Bobby's Mother called both
Sally and Bobby into the living room to talk to them. "I received a call from
Mrs. Johnson last night, and she said she saw two people that looked very much
like you two getting out of a car the other day, except for one thing. The
one that looked like you Bobby was dressed up like a girl. Now what's going
on here", Bobby's mother asked. "It's my fault Mrs. Thompson, I have been
making Bobby dress up like a girl to punish him when he has misbehaved.",
Sally replied (not reveling that Bobby derived pleasure from being dressed up
like a girl). "I think a simple scolding would have done better young lady.",
Bobby's mother said. "I'm sorry.", replied Sally. "I think you had better
leave. I will find another baby-sitter for Bobby", Bobby's mother said.
Sally got up and started out the door. "Good by Sally.", Bobby said almost
crying. "Good bye Bobby.", Sally returned, "I'm sorry." "That's ok.", Bobby
said.
Bobby's mother called into work and told them that she would be out for a
couple of days while she found another baby-sitter. "Come on Bobby, lets go
out and get you a hair cut.", his mother said. "I'm really too upset to go
out today Mommy.", Bobby replied. "Ok, I understand.", Bobby's mother said.
Bobby spent the next few days just mopping around the house. "What's wrong?",
Bobby's mother asked. "I miss Sally.", Bobby replied. "But she made you
dress in girls clothes, Bobby!", his mother said. "I know.", he replied.
There was a pause for a few seconds then Bobby's mother asked,
"Bobby?". "What?". "How did feel about having Sally dress you up like a
girl?". There was dead silence for a minute finally Bobby spoke up. "The
first time Sally made me dress like a girl I did not want to do it, but she
made me look in the mirror. When I saw how pretty I looked I felt a strange
sensation that I had never felt before. After that I wanted more and more to
dress like a girl and slowly I stopped liking anything that made me feel like
a boy. One day I went into your bathroom and shaved my legs and underarms
without Sally even knowing about it." "Oh.", his mother said with a great
deal of surprise. "How do you feel about it now." "Well I liked it better
each time she did it, she made me look so pretty Mommy. The day after you
left for your business Sally took me to a fashion show down town because she
had to model in it. After we got there, there was this dress that they
couldn't find anyone to model, so asked me to model it for them and when I
finished they let me keep everything I was wearing so I wore it home. That's
when Mrs. Johnson saw us. Then the next day I went to the beach dressed as
girl. I just feel so special when I'm dressed as a girl and now I wish I was
a girl! Please don't take this away from me!", Bobby said.
Bobby's Mother just sat there with her mouth hanging open. "I don't know
what to say.", his mother replied. Bobby's mother did not know what to make
of this new revelation, but she knew her son very well and when she looked
into his eyes it did not seem to be just a passing fancy with Bobby, it
appeared that it was a desire that would probably be with him for ever. After
Bobby left the room she just sat there thinking.
That night just before Bobby went to bed his mother told him that she had
arranged for him to spend the next few days at a camp because she had to get
back to work, and after that she would have to spend the weekend looking for a
baby-sitter for him. "Ok.", Bobby said and went to bed. The next morning
they got up early and Bobby's mother drove him to the camp. Bobby spent the
next four days at the camp. It was late Sunday night when Bobby's mother came
to get him. As they rode home Bobby's mother noticed that there was no change
in his mood. When they got home it was well past Bobby's bed time. Bobby's
mother said to him, "Go up stairs and take a shower and wash the two days of
camp off of yourself". Bobby went up stairs to the bathroom, got undressed,
and got into the shower. When he got into the shower he noticed a bar of
perfumed soap. He just stood there thinking. He wanted to dress up like a
girl so bad. Finally he decided that washing with the perfumed soap would be
as close as he could get to dressing up in girl's clothes. So he picked up
the soap and started to wash with it. As he was showering he thought to
himself how much the soap smelled like the perfume that Sally had put on him.
After Bobby had finished he put on his pajamas, walked down the hallway to his
bedroom and climbed into bed.
CHAPTER 6
The next morning Bobby's mother came up to Bobby's room early and sat on
Bobby's bed. "Wake up Honey, I want to talk to you.", She said putting her
hand on Bobby's shoulder and gently shaking it. Bobby rolled over still half
asleep. He could still smell the scent of the soap from his shower the night
before. Bobby looked at his mother. She had a very concerned look on her
face. Finally she spoke up. "I've been thinking about the talk we had the
other day. I didn't know you felt the way you did about Sally, or wearing
girls clothes. A mother can tell when her child wants something just because
it's new and when they are really serious about something. When I looked at
your expression I saw a great deal of sincerity in your face. In the past
when you've looked like that you were very serious about what you were asking
for. So as a result I've had to do a lot of thinking and agonizing about what
I should do about it and I've decided that no matter how hard it would be to
change things so no one would find out that your not really a girl, it's your
happiness that's important. So Bobby I'm going to ask you to make a decision.
If you really want to dress as a girl that's ok but you must decided what you
are going to be, a boy or a girl. If you decide that you want to stay a boy I
don't want you to so much as pick up a pocketbook, but if you choose to be a
girl then it's lipstick, high heels, and dresses from now on. I will not
allow any switching back and forth because it will be tough enough convincing
people that their records are wrong when they have you down as a boy
everywhere. Mrs. Johnson knew it was you at the beach and it's just dumb luck
that she has moved away, but there is another lady living in the house next
door and once you are introduced as my son or my daughter I never want to have
to suffer the embarrassment of having her know I allow my child to cross
dress. So take your time to decide what you want to be because once you've
made it I will not let you change your mind."
I realize that this will be a difficult decision, and I want you to take
all the time you need. I'm going to stay out of work until you decide because
if you decide you want to be a girl I'll call Sally back, if not I'll find a
new baby-sitter".
A few days later it was about 10 O'clock in the morning and Bobby was in
his room thinking. There was a knock at the door down stairs. Bobby heard
his mother open the door. He had just gotten up and was still in his pajamas.
"Hello, my name is Sylvia Porter. I just moved in next door and I thought I'd
come over and introduce myself.", Bobby heard a voice say. "Well, it's so
nice to meet you, my name is Jane Thompson, come in.", Bobby heard his mother
say. Bobby decided he could stand it no longer, he made up his mind. He took
off his clothes, went over and opened his bottom bureau drawer, took out the
Panties, garter belt, nylon stockings, and earrings that Sally had given him,
went down the hallway to his mother's room, put the things from his drawer on
her bed, went into her bathroom, took out her shaver, and shaved his legs, and
underarms. Next he walked back into her bedroom and opened her closet door.
He looked over all the clothes that she had there and took out a red leather
skirt and a white satin blouse. Then he walked over to her bureau drawer. He
took out a red bra and a red full slip. He laid all of the clothes on the
bed, and stood there thinking to himself, "If I do what I am about to do I
will never be able to put on boy's clothes again". As he looked down at the
clothes he could feel the desire building inside and he knew that he must do
what he was about to do.
Bobby picked up the panties and held them out in front of himself and one
leg at a time, stepped into them. He slowly pulled the panties up around his
waist. Next he picked up the garter belt and clasped it around his waist. He
was about to put on one of the stockings when he remembered how pretty his
toenails looked with the nail-polish on them. He walked over to his mother's
vanity and picked up a bottle of red nail-polish, sat down on the chair,
rested his left foot on the edge of the chair and slowly applied the polish to
each of his toenails. He remembered that Sally had showed him that when he
was putting on nail polish that he should take long strokes out over the edge
of the nail while keeping plenty of polish on the brush, in order to get a
smooth even coat of polish on the nail. When he was done he put his left foot
on the floor and put his right foot on the edge of the chair and repeated the
process. He was about to put the polish on his fingernails when he remembered
that sometimes his mother wore false fingernails.
Bobby decided to look around to see if he could find them. He found them
in one of the drawers of the vanity, and decided to wait until later to put
them on. He waited until the polish on his toenails was dry and then applied
another coat and waited for that to dry, before putting on a third and final
coat. He waited until the last coat of nail polish was almost dry and decided
to put on the bra. He walked over to the bed, picked it up, put his arms
through the straps, and pulled them up around his shoulders. When he tried to
do up the hooks in the back. He found it very difficult, and it took him
several minutes to accomplish it. After he got the bra fastened in the back
he walked over to his mothers bureau draw, took out two pairs of panties and
stuffed them into one of the bra cups. after shifting them around in order to
make them look as much like a natural breast as he could, he took out two more
pairs and put them in the other cup.
When he had finished with the bra he checked his toenails, and found that
the polish was completely dry, he walked over and sat on the bed and picked up
the nylon stockings. One at a time he gathered up the stockings, placed his
foot in, and pulled them up. Next he clasped the stockings to the garter belt
and stood up. He decided not to take a chance on putting a run in his
stockings and put a pair of his mother's slippers. After that he picked up
the full slip, slid it over his head and down into place. Then he picked up
the satin blouse. It had long sleeves and a high neck line. In the back of
the collar was a three inch slit so that it could be put on and three pearl
buttons to close it up after it was on. He put his arms through the sleeves,
put it on over his head, and then did up the buttons. Next he put on the
leather skirt and snapped the waist closed in the back and zipped it up.
When this was done he next decided to do up his hair he took out his
mother's curling iron and plugged it in to let it heat up. Using all things
that Sally had showed him about hair dressing he brushed it back. Then he
took a red hair ribbon out of the vanity drawer and tied his hair into a pony
tail in the back. Then he took small sections of the pony tail and made
banana curls with the curling iron. He looked at himself in the mirror and
decided that he did almost as good a job as Sally did.
Next it was time to put on his makeup. Again he remembered back to what
Sally had taught him. Still sitting down at the vanity he started with his
eyes. First he applied eye liner around his eyes. Then he put mascara on his
eyelashes, and finally eye shadow on his eye lids. Then he applied makeup
base to his face, pink blush to his cheeks, and powder to soften the blush and
cover the makeup base. After that he picked up a red lipstick from his
mother's vanity. He could feel his hand shaking as he cranked up the
lipstick. He thought to himself, "Relax there's a lady downstairs that you
have to convince you're a real girl." Slowly he brought the lipstick to his
lips. First he outlined his lips then he filled them in. He looked at
himself in the mirror and smiled at the good job he was doing.
He got up from the chair, went over to his mother's closet, picked out a
pair of red, open-toed high heeled sandals that buckled around the ankle,
walked over to the bed, and one at a time removed his
mother's slippers and put the high heels on. "Only one more thing to do.", he
said softly to himself. He
walked back over to the vanity and started to put the false fingernails on his
fingers. One finger at a time he removed glue tabs from the paper backing,
put it on his fingernail and applied a false fingernail. Finally all ten
fingers were done. Bobby stood up and looked at himself in the full length
mirror. He turned from side to side checking himself out. He decided that he
was finished, took a deep breath, and walked to into the hallway.
Bobby listened, he did not hear any talking, had Sylvia Porter gone home,
after all it had taken him almost two hours to get ready. As he continued to
listen he herd dishes rattling in the kitchen. He went down the back stairs
into the kitchen. His mother was there preparing a tray with sandwiches and
tea.
"Mom, I've made my decision." Bobby's mother looked up at Bobby. When
she saw him her mouth dropped open. "Bobby, our new neighbor is in the living
room!", his mother said. "I know it.", Bobby replied. "Bobby, this is no
joke, I meant what I said the other day!" Bobby looked straight at his mother
for several seconds. Then without saying a word, picked up the tray, and
walked into the living room. "Hello, I'm Bobby Thompson, Jane Thompson's
daughter.", Bobby's mother heard him say from the kitchen.
After a few minutes Bobby's mother nervously walked into the living room.
Bobby was sitting in a chair talking to Sylvia. As Bobby's mother looked on
she could not help but notice how feminine Bobby looked. They talked for
about a half an hour. After that Sylvia left and it was obvious that she did
not suspect that Bobby was not really a girl.
After Sylvia had left Bobby's mother looked over at him and said, "Well,
I guess I have a daughter." "I, guess so.", Bobby replied. "I think I'll
call Sally back in the morning, she has taught you well and she saw that I had
a daughter before I did. She can take care of you again and I have to get
back to work. I'll have her take you out to get a new wardrobe." As Bobby
listened to his mother talk he could sense that she was a little
uncomfortable, so when she finished he walked over to his mother and gave her
a big hug. "Don't worry Mom I'll be happier this way.", Bobby said. Bobby's
mother looked him in the eyes, smiled and said, "Welcome to the world of
womanhood."
