He Didn't Like It
By Cheryl Lynn
This is my 100th submission to FM and hope it worthy for such a
milestone. All the usual disclaimers apply and readers must be older
than eighteen. Not for the sweet/sentimental reader as it features
forced femininization and sex. I cannot tolerate such things in reality
but this is fiction. Some of the events in this story I'm sad to say
are based on true events. May be downloaded for personal use only. All
other use strictly prohibited unless approved by the author. Comments
are welcome at
[email protected].
He Didn't Like It
Robert "Bobby" Trent Jr. was born in 1950 in New York City where both
his parents had good jobs. After his birth his mother, Gwendolyn quit
working to take care of the baby. She wasn't altogether happy as she
wanted a girl. It was the only reason she married in the first place.
Gwendolyn or Gwen as she preferred, was a lesbian. Someone society
severely frowned upon back then. She only married to keep up
appearances and have a daughter. Robert Jr. was a disappointment. The
marriage was a rocky one to begin with and only became worse over time.
His dad, Robert Sr. after six years, had had enough and skipped the
state with his secretary. Divorce laws were very restrictive back then
but one of the few reasons accepted was abandonment. Gwen couldn't file
for a divorce until a full year passed. During that time she moved to
Jersey City and got a job.
With her husband out of the picture, Gwendolyn felt liberated but still
restricted by societal requirements. She pushed those limits by wearing
mostly slacks, limiting her makeup to lipstick and cutting her hair
short. She also began dressing Bobby more like a much younger boy.
Tight shorts with as feminine shirts as she could get away with. Until
he started school wore little girl's cotton panties and dresses at home.
She even had him wearing girly baby doll nighties and insisted he always
call her momma.
Gwen also refused to get his hair cut short like boys his age. She
insisted he keep it almost collar length and made him brush it one
hundred strokes every night. To keep him from peeing all over the
toilet seat trained him sit to do his business. Occasionally as he got
older, dressed him in frilly baby dolls as a "punishment" for
misbehavior. That was about as far as she could take it without
arousing suspicions. Going to school forced her to dress and let Bobby
act like a regular boy. When at home disciplined if he acted too
boyish. Gwen kept her personal life as secret as possible.
She of course "dated" occasionally to keep up appearances. Gwen did
have several girl friends over the years but they didn't last. She
wanted a lasting relationship with the right woman. A "husband" to be
exact. That finally happened before Bobby graduated the ninth grade.
Gwendolyn wasn't happy with her hairdresser and decided to try someone
new. Jo's Beauty Shop was in Jersey City near where she lived. There
she met the owner Josephine Whitehurst.
Josephine Whitehurst owned two salons, one in Jersey and the other in
Greenwich Village in New York City. She was quite successful and more
open with her lesbian leanings than Gwendolyn Trent. All the staff at
her salons were either gay women or men. It didn't take them long to
become close friends.
##
Robert "Bobby" Trent Jr. was thirteen and pretty much your average teen
boy. He had sandy blond collar length bushy hair, somewhat delicate
face, green eyes and lanky frame. Puberty hadn't set in to change him
from boy to manhood yet. He liked sports and rough housing with his
friends. Bobby, as he preferred to be called, loved the New York
Yankees. His favorite was Micky Mantle but Yogi a close second. He was
at that point in life where he was becoming curious about girls. Bobby
didn't think they had cooties anymore just different. He graduated from
the ninth grade and looking forward to summer. Bobby planned on
spending most of his time with his buddies playing baseball at the park.
Josh, his best friend, had even planned a camping trip for them.
"Bobby my dad and I are going camping at Lake Champlain for a week. You
want to come? It'll be a blast," Josh asked the last day of school,
Bobby couldn't believe his luck. He and his dad before he skipped town
with his secretary, had gone camping. That was something he really
missed. Living with his momma hadn't been much fun since his dad left.
She was always criticizing and bitter. She had never been that doting
mother you see on television shows to begin with. So, getting a chance
to be with Josh and his dad a welcomed relief.
"Yeah, sure! When we going so I can ask momma," he quickly replied.
"Probably middle of June. See ya at the park Saturday and tell you
then," his friend answered giving him a poke in the arm.
It was with a happy skip in his step as he headed home. "I hope momma
lets me go. She's been on my case ever since dad left us. I just hope
she'll let me get that flattop I want this summer. Maybe she'll be glad
to get me out of the house for a week. I sure hope so," he thought.
Bobby's happy smile disappeared as soon as he entered the front door.
Sitting on the entranceway floor were several suitcases. "Momma I'm
home. What's with the suitcases?" he yelled.
"How many times do I have to tell you not to shout!" she barked coming
out of the kitchen. "We're going to stay with a very dear friend of
mine for a while in New York City. I fixed you a snack in the kitchen.
Hurry up and eat while I load the car."
"New York? Bu....but I have plans," he began to complain.
"I don't care about your plans. Now do as you were told or I'll get my
hairbrush. When you finish your snack go change out of your school
clothes. I put out something to wear on your bed," she snapped back.
When she took that tone Bobby knew not to argue further. His backside
had paid the penalty more than enough. "Man, this just sucks," he
thought heading into the kitchen.
In his room Bobby stripped down to his y-fronts and reluctantly began to
dress. He wasn't happy with what she had put out for him. It was his
hated little boy suit. A pair of black knee length short pants, pink
polyester dress shirt, thin black silk tie and black Eaton styled
jacket. The cuffs of the dress shirt had a small frill of eyelet lace
which extended out from the jacket's.
"I'm a teenager now. Why won't she get me long pants and I hate this
stupid shirt," he grumbled.
##
It was his first trip into The City and gawked at all the skyscrapers.
When his mother pulled into a parking spot in front of Jo's Beauty Shop
Bobby was surprised.
"With all the neat places I've seen why is she stopping here?" he
thought.
"My friend owns this place and I told her we'd pick her up. She doesn't
need a car living in the Village. Come on and you be on your best
behavior or else," she ordered.
Bobby hadn't been in a beauty shop since he was younger but the
distinctive smells bothered him. Before he started school his mother
kept his hair long and curled. Gwen was very unhappy to have it cut
into a more boyish style before going to first grade. Bobby vaguely
remembered being seated in one of those chairs and getting a perm. The
various aromas assaulting his nose made him very uncomfortable.
"Momma may I please go back and wait in the car?" he asked.
"Don't be silly. Oh, there's Jo. Come along now and behave," she
stated.
Josephine "Jo" Whitehurst was a striking woman of middle age with raven
black hair worn in a tucked under short bob. She was tall in her three-
inch spike heels and wearing a black silk pants suit with a white cotton
blouse. Josephine was a little thick in the waist but otherwise very
shapely. She was wearing full makeup, something his mother seldom did.
She looked and spoke a lot like the star of that television show, "The
Nanny."
Outwardly you wouldn't think she was the type of woman Gwendolyn Trent
would fall for. She was looking for a "husband" type of girl. Someone
who was decisive, be the major bread winner and not so feminine. Being
out of the workforce for so long taking care of Bobby, Gwen was lucky to
get a job as an office manager. She didn't even have that now as the
company just folded. However when Josephine (Jo) Whitehurst began
talking with an air of total authority, the attraction was obvious.
"Gwen darling about time you got here. Come, come introduce me to your
precious little boy," she greeted opening her arms for a hug.
Bobby was infatuated with this pretty woman at first but stunned when
she hugged his mother then gave her a resounding kiss on the lips. He
was also put off when she called him a little boy. He still thought her
pretty but didn't like how she referred to him.
"I'm a teenager darn it," he thought as the kiss broke and she turned
her attention to him.
"So you're Bobbie," she said making his name sound more girlish. "Don't
just stand there like a stick in the mud, come give your Aunt Jo a hug."
It was a brief hug and she ran her hand through his hair as she stepped
back. "Gwen baby little Bobbie is just so cute but that hair needs some
work. Why don't you let one of my stylist do her magic on him since
you're already here?"
Jo didn't wait for a response, calling out, "Taffy come take little
Bobbie to your station. He has great hair but I think with a little
styling and coloring to even it out would work wonders."
"Bu....but I don't wan...want my hair messed with an...and I..I'm not a
little..," he began stuttering but stopped before he could finish.
"Nonsense little Bobbie. You go with Taffy here. She's just going to
even out the color and trim off all those split ends I see. Now go
along and behave or else your mommy might have to spanky-spank. Besides
we need some time to talk grownup stuff. This way you won't get into
any mischief," she interrupted as if he was just a little kid.
Turning to Taffy Jo whispered, "Make him a strawberry blond and put some
curls into that mop. It's too short for anything else. While you're at
it, paint his nails a light pink."
"Nooooo, I don't want," he began to complain but quickly shrank back.
"Bobbie! Go with Taffy and behave!" Jo said loud and shrilly enough to
get the attention of everyone in the salon.
The way she yelled, the scowl on her face and look of her eyes made
Bobby take a step back. It was the same tone and look he got from his
momma before she grabbed the wooden hairbrush. This woman though scared
him much worse. He felt someone grab his hand and pull him away. When
he looked up it was Taffy.
"Bobbie, you really shouldn't make Miss. Jo mad like that. Now come
along and let me do what I must or we'll both be in big trouble," she
said taking him to her workstation.
##
While Bobby was getting worked on they went into the office, embraced
closely and kissed with passion. When the kiss broke leaving Bobby's
mother gasping, Jo gushed, "Oh my darling, he's absolutely the cutest
little thing. It's a shame he isn't a girl. Those emerald green eyes
and those long lashes are simply to die for. Eyes way to pretty to be
on a boy."
"Jo you know I always wanted a little girl but fate dealt me a cruel
hand. I did raise him as my little girl for a while and Bobby was so
precious then. I had to stop when I sent him to school. I hated doing
that. It broke my heart but what choice did I have? It would be only a
matter of time before someone found out. I didn't even want to think
about what they would have done to me then," she replied wiping away a
tear.
"Look Gwen honey, you're staying for the summer so why not bring out the
little girl in Bobbie? No one knows him around here except my staff
today. They would be no problem if we brought out Bobbie's feminine
side. What's say baby? Let's do it," Jo gleefully responded.
"Oh, I just don't know. Bobby certainly wouldn't let us do something
like that. He's too old now. He would fight us tooth and nail and
surely bring attention we don't want. Our lifestyle is severely
repressed and if that got out an...and they find out," she replied
trembling.
"You have a point dearest but I think you're giving too much credit to
Bobbie's maturity. Besides it's only for the summer. Look, I told
Taffy to dye his hair strawberry blond, put in some curls and paint his
nails a pale pink. I'm willing to bet he won't want to see anybody.
Much less tell anyone with just that little bit. Getting into cute
undies and dresses, I think he'll be so embarrassed by how pretty he
looks, he'll cooperate. The last thing in the world he'll want is to be
discovered as a boy in a dress. Trust me on this. Come on Taffy should
almost be finished. Let's see how he reacts. Then you can decide," Jo
stated with confidence.
"Well I'm still not sure about doing it dearest. If we do this though,
he has to be able to really pass as a girl. I mean that! We can't
afford for anyone to find out his little secret. I'll go along with it
for...for now anyway unless he puts up a big fuss," she replied.
"You just have to be firm with him dear," Jo replied.
##
"If you have to cut my hair would you please give me a flat top? I get
kidded a lot at school because I have such long hair. All the other
boys have either a buzz cut or flat top," Bobby said as he got up into
Taffy's styling chair.
"What? Cut off that beautiful thick hair? I think it just needs those
split ends trimmed and Miss. Jo told me to even out the color. So
that's what I'm going to do. Now you be good for Miss. Taffy or you
will get a spanking when your mother comes back," Taffy said tying a
lavender drape around his neck.
"Crud! I want a flat top like all the other guys. What'd she mean by
even out the color? Like my hair color as it is. Momma probably would
spank me here too. She's been mad about something all week," he
thought.
Taffy spent most of her time shampooing, conditioning and dying his
hair. "He's not going to like this but It's what Miss. Jo wants. This
new gel treatment with special conditioners will make his hair shine and
the color will really last. Now all I need to do is put in some nice
curls. Can't do a perm but setting gel and hairspray should do the
trick," Taffy thought as she finished trimming off Bobby's split ends.
It wasn't until Taffy sectioned his hair and begin rolling it onto a
small bristle rollers that Bobby protested. "Wha...What are you doing?"
he demanded reaching up to bat her hand away.
Taffy slapped his hand sharply with her rat tail comb. "Behave!" she
demanded loudly making him cringe.
"Ouch! That hurt. Sh...she's putting curlers in my hair. I don't want
that but I don't want a spanking either," he thought as a tear crept
into his eye.
His tears began to really flow down his cheeks sitting under the domed
dryer. He was getting a manicure/pedicure. Taffy told him it was a
punishment for misbehaving while she rolled his hair. His finger nails
were rounded and varnished a light pink but his toes in a much richer
bright pink.
"They're painting my nails like a girl's. I hate this but momma will
make them take it off, won't she?" he thought.
##
Taffy was putting the final touches to Bobby's hair. He was looking
horror struck into the mirror he was now facing. The heavy perfumed
scent of hairspray filling his nose. Bobby's hair was not only a rich
strawberry color but styled into a mass of corkscrew curls.
"What has she done? She made my hair look like a girl! I can't go
anywhere looking like this," his mind screamed as the women walked up.
"Oh my," his mother gasped.
"How delightful! Taffy you did a beautiful job," Jo stated smiling ear
to ear. Then turning to Gwendolyn added, "Darling what do you think
now? Doesn't your little Bobbie look beautiful?"
"Momma you got to make then change me back! Look what they did to my
hair an...and they painted my nails like a girl. See?" Bobby protested
holding up his hands.
"Bobbie sweetie, I think you're even more adorable now. Besides that's
a very light shade of pink and no one will notice. Dry those tears and
come along. Your mommy and I need to get home before the traffic gets
too bad," Jo beamed.
"No! I'm not going anywhere like this," he loudly stated getting out of
the chair.
He was surprised as his momma slapped him across the face. "Bobby be
nice or I swear I'll drop your pants right here and give you a good
spanking. Your Aunt Jo gave you a compliment! Now tell her thankyou
and it better sound sincere," she demanded.
"Jo was right. With the proper clothing would be my little girl but he
doesn't like it. Jo said to be firm. If he still puts up a fight now,
I'll have to stop," she thought.
It wasn't a hard slap but it got his attention. Swallowing his pride
and wiping his arm across his tears dutifully replied, "I..eerrr...Thank
you Aunt Jo," he managed in a soft voice to his momma's relief.
"What was that little Bobbie? I didn't hear you. Speak up. Thank me
for what?" Aunt Jo sternly said.
"I...I said thank you Aunt Jo...err..for...for everything," he managed
to reply blushing as fresh tears welled up.
"Oh for goodness sakes little Bobbie, it was nothing. I was more than
happy to do it for such a cutie pie," she said bending down, smiling
broadly and wiping away his tears.
"Well I'm glad that's settled. Now thank Miss. Taffy and we can go home
to Aunt Jo's," his momma stated.
##
Bobby and his momma were both surprised when they got to Aunt Jo's. It
was a penthouse apartment in the Village. Gwen couldn't figure out how
her beloved could afford such a large three-bedroom apartment. She had
a reasonable idea how much it might have cost. Owning two beauty shops
couldn't possibly clear enough to make the payments.
Looking around at the nicely furnished apartment astonished she had to
ask. "Jo how...how can you afford such luxury?"
"Darling I run a very exclusive escort service for people that enjoy our
lifestyle. I've lived in the City all my life and with my beauty shops
know many prominent homosexuals. I'm very discrete, trusted and they
pay me a lot of money. Hell, that's how I paid for my shops. So don't
get any ideas about paying for anything. That's what I'm here for," she
boastfully explained.
Josephine Whitehouse was anything but altruistic. Now that she had met
Bobby had future plans for him. Given time he would be making her a lot
of money with his cute good looks. Yes, she cared deeply for his momma
but not love struck like her. She was primarily a business woman after
all. Gwendolyn Trent was so in love with her, Aunt Jo figured she could
talk her into anything. Gwen desperately wanted a daughter, so she
would give her one for now. Later when he was of age, make him into a
sissy. Her clients would pay big bucks to be with him.
Bobby wasn't pleased with the room he was given. It was larger and
nicer than the one he had but too frilly. The walls were covered in a
floral wallpaper. The wooden floors had fuzzy throw rugs scattered
about and furnishings delicate. The queen bed was a mahogany spindle
bed with a floral comforter and lace frilled pillows. There were some
framed pictures of flowers hanging on three walls. The fragrance of
flowers hung heavy in the air.
"Little Bobbie this is your room and I expect you to keep it tidy like
it is now. The bathroom is right across the hall," Aunt Jo stated
patting him on the bottom.
He wanted to tell her to stop calling him little and he wanted another
room. The pat to his bottom silenced him. "I want her to stop calling
me little. I'm a teenager now and this is a girl's room. She's got my
hair and nails all girly looking too. Why doesn't momma put a stop to
all this. I'm not no silly girl," he thought.
"Bobby, take your suitcase, unpack, wash up and change your clothes then
come back to the living room," his momma said giving a slight shove.
"Oh, and don't get your hair wet or try to remove that polish," she
added as an afterthought.
"Shucks! I don't like this and wanna go home," he thought tossing the
suitcase on the bed.
Dressed in a pair of shorts and tee Bobby went to the kitchen. He was
used to helping momma in the kitchen but Aunt Jo embarrassed him again.
As he entered, she gave him a bear hug.
"Even in those ugly shorts and shirt you're just too cute sweetie," she
said breaking the hug. "Here let me put this on for you then you can
help your mommy prepare supper for us," she added tying a pink organza
lace frilled apron around his waist.
The apron was very full on his thin frame and looked more like a skirt
than anything else. His momma came over and had him do a little twirl.
"Very nice Jo, I think my little Bobby looks just precious. Come along
dear you can cut up the carrots for me," she said smiling happily. "Jo
was so right. With that hair and polish wearing that apron, he could
pass as my little girl," she thought.
Later that night Bobby tried to stop his momma from putting his hair
into bristle curlers. Several hard slaps to his Donald Duck pajama
covered bottom ended his protests. With his hair up, she sprayed it
heavily with hairspray then put on a black hairnet to hold everything in
place.
"Momma please take them out. They are sticking my head and I won't be
able to go to sleep if you leave them," he protested.
"Don't you dare even think about taking those curlers out! Aunt Jo went
to a lot of trouble having it done and we'll keep it that way for now,"
she warned.
##
After a miserable night, Aunt Jo woke him up. "Time to rise and shine
little Bobbie," she greeted warmly bending over and kissing him full on
the lips. "Go to the bathroom and get cleaned up. I have your bath
waiting and don't forget to put on that shower cap I left out for you.
While you're in there I'll get your clothing ready. We have a big day
planned."
"If I hear her say little Bobbie again I'll scream. It's bad enough
what she did to me and I don't need that. Now I have to take a bath. I
haven't done that since I was just a little kid but I'm a teenager now.
Why can't she just leave me alone," he thought.
When he entered the bathroom, he froze as the heavy floral scent coming
from the multi-colored bubbles in the tub hit his nose. "Oh no! A
bubble bath! I'm not getting in there," he thought backing out the
door.
"Just where do you think you're going! I said take your bath! Now get
back in there and do it unless you want me to bathe you like a baby!"
Aunt Jo practically screamed making him jump.
"I don't like taking a bath much less wearing this stupid cap with all
those phony flowers on it. Guess it's better than have her wash me
though," he mumbled as he picked up the pink bar of soap.
It wasn't until he went to brush his teeth that he noticed his lips were
imprinted with Aunt Jo's bright red lipstick. Grabbing the wash cloth
from the tub scrubbed his lips until it was gone.
He wasn't happy seeing the clothing Aunt Jo had put out for him lying on
his bed. It was something his momma sometimes made him wear on the
weekends and he hated it. If it had long pants legs might have been
acceptable but these had short flare legs. It was in a light weight
baby blue cotton cut similarly to bib overalls. Instead of the brass
hook and button on overall straps these had large white buttons. Making
it even more hideous there was an embroidered teddy bear on the bib.
The white shirt that went with it had a rounded collar and cap sleeves
with a hint of ruffle.
"I don't want to wear that! I hate that! I want my jeans!" Bobby
protested.
"I think this will look precious on you little Bobbie. Besides your
mommy didn't pack any jeans. Now you have a choice. You can either put
on your own clothes or I can do it for you. So what's it gonna be?" she
snapped.
Seeing the look in Aunt Jo's eyes and her fists on her hips, Bobby
decided not to argue. "Okay, I can dress myself but I won't like it,"
he answered.
"Very well. Once you're dressed come to the kitchen for a quick
breakfast. I'll take those curlers out then," she said leaving.
"I can't go anywhere looking like this!" he thought gazing into the
mirror. "It was bad enough when momma made me wear it but I looked like
a boy then. With this hair, I look like a girl!"
Entering the kitchen Bobby saw his momma sitting with Aunt Jo. "Momma
look at me. I'm not going anywhere looking like this," he complained.
"Bobby you look just fine. Your Aunt Jo told me what she picked and I
whole heartily agree. Now sit at the table and eat your cereal," she
stated giving him that look.
"I look like a...a girl with this hair. At least get me a pair of long
pants," he whined hoping she would change her mind.
"I didn't pack any. It's summer and too hot for long pants. Now stop
complaining and eat your breakfast or do I have to get my hairbrush!"
she retorted.
"Everyone is going to make fun of me when we go out. I look like a
little kid and worse with this hair like a little girl. I hate this,"
he said finishing his cereal.
"We both think you're adorable little Bobbie," Aunt Jo stated. "If
you're so concerned about people seeing you, then I suggest you act like
a little girl. That way no will make fun or tease you," Aunt Jo said
smiling from ear to ear.
"I don't know how to act like no girl," he moaned.
"Well maybe not but little girls always smile and look happy. So happy
they skip a lot. Now give us a big happy smile and let's see you skip,"
Aunt Jo explained.
"You've got to be kidding. I'm not happy and skip when I walk? Girls
are silly though. I guess I should try. I certainly don't want anyone
knowing I was a boy dressed and looking like this. Guess I'll have to
try smiling anyway. I'm not skipping anywhere," he thought.
"That smile needs to be much bigger but if that's the best you can do
come here. I have something that will help," Aunt Jo said reaching into
her purse and removing an ivory cylinder.
When he was near enough, she reached out and cupped his chin. "Hold
still I don't want to smear this. It's just a bit of lipstick. Wearing
lipstick no one will think you're a little boy. I said hold still," she
commanded spreading a thick coat of glistening red to his lips.
Reaching to the table grabbed a napkin, folded it and had him blot.
His eyes glistening with unshed tears he tried to back away. "Not yet!
I need to put another coat on. There no one will think you're a little
boy now," she said putting away the ivory tube. Then added making him
blush, "Oh look at the pretty lip print you left on the napkin. Your
first too so I can't just toss this in the trash. While we're out I'll
buy you a scrapbook to save precious memories like this for when you are
older. Now just one more thing to make sure you look totally like a
little girl."
Aunt Jo got up and left leaving Bobby parting his lips, running his
tongue across the bottom then closing them. "They're all sticky and
taste funny. I can't believe I let her do that but she's right. Only
silly girls wear this stuff. It's only until we get back then I'll wipe
it off," he thought fighting back tears.
"Okay we're already to go. Take this little Bobbie," Aunt Jo said
handing him a small white leather purse with a pearl handle. Seeing him
hesitate added, "have you ever seen a girl without a purse? Now take it
and let's go. It completes your disguise."
As they were leaving Bobby saw his reflection in the hall mirror. "I
look just like those silly girls in school. Only they wouldn't dress
like this. At least they didn't put a dress on me."
As they were walking down the sidewalk they met a woman Jo knew. Bobby
tried to hide behind his momma as they talked. "Who's that precious
little girl?" the woman asked.
"My daughter Bobbie," his momma said pushing him into the forefront.
"She's very shy. Bobbie say hello to Mrs. Grimwald."
"Hello ma'am," he managed barely above a whisper.
"Nice to meet you too Bobbie," she replied reaching down to pinch his
blushing cheek. "You're just the cutest little thing."
"Look Bobbie we'll be going out a lot and meeting my friends. Unless
you want them to find out you're really a boy, you need some more
clothes. Yes, I know you have clothes in your suitcase but you need
some girl's clothing. No, you do! A lot of people will see you as a
little girl today. What do you think they are going to say if you go
out dressed like a boy? That's right! They'll call you a sissy. A
great big sissy! So dry those tears and let's go," Aunt Jo admonished
after Mrs. Grimwald had left.
"I don't want no girl's clothes but I don't want to be called a sissy
either. Wait there's a barber shop across the street. I can get a flat
top and get rid of these stupid curls," he thought then said excitedly,
"Look, there's a barber shop across the street. I can get a flat top
and won't need those girly clothes."
"Bobby how dare you suggest such a thing!" his momma screeched. "Your
Aunt Jo went to a lot of trouble getting your hair styled. We'll do no
such thing! Now apologize for being so rude or I'll blister your behind
right here and now!"
"Oh no, she would too," he thought and said, "I'm sorry Aunt Jo...I.. I
didn't mean to be rude."
##
It had been a long traumatizing day for Bobby. It seemed like they went
into every store in the Village. Aunt Jo seemed to know every shop
owner and he was constantly introduced as his momma's daughter. In one
shop he had to pose with a backdrop of a field of flowers having his
picture taken. In another pose he had to cradle a teddy bear in his
arms. That was embarrassing but other stops were mortifying. When they
left the Tween and Teen store Bobby was beet red from head to toe. The
store had both boys and girls clothing but he was taken into the girls'
section. The owner, Miss. Ellen Hunt, was an old friend of Aunt Jo and
happy to help them. He had never been so humiliated as he was in the
changing room being measured for his first training bra.
"You're a little undeveloped for a girl your age Bobbie, barely an A-
cup. Not to worry though, I've seen many girls like you blossom in no
time at all," Miss. Hunt assured him seeing tears. "Poor little thing.
She's embarrassed with her small boobies. I'll make sure to get her the
pretties ones I have," she thought.
"Like I ever want boobies," he thought blushing brighter at the idea.
When she left to get the bras Aunt Jo cautioned, "Bobbie dry those tears
and put a smile on that face. Otherwise she will know you are a boy and
might call the police. You're in a girl's dressing room after all. We
certainly don't want that! All little girls are thrilled to get their
first bra. So act happy when Miss. Hunt returns."
"I don't want or need no bra but the police? I'm in a girl's dressing
room where no boy should be. I better do as she says but I won't be
happy," he thought.
"Bobbie I think you're going to love these pretty bras. These are for
day wear and these here are for bed time," Miss. Hunt beamed holding up
the bras. "Here let's try this one on first. It's a super soft 30-A
with molded cups and a bit of padding. This one you can wear under any
clothing as it's bleach white and won't show through. The other one is
in a pearl heather and worn under darker clothing. See it has scalloped
edging and a pretty little satin bow in front," she said slipping the
straps over his shoulders.
"These little metal slides let you adjust the straps for a more
comfortable fit. It has a single hook and eye back closure to make you
feel like a big girl too. Put your hands back and I'll show you how to
fasten it," she continued.
"Like I want to learn how to put on a bra but I can't let her think I'm
really a boy. Gosh! I look like I have boobs," he thought glancing at
his chest.
"Now these are for bed time. This style is called a bralette. It has
elegant lace trimming the broad elastic band and pull over your head.
They are more comfortable than day time bras. This one is a pretty pink
and the other is called electric blue," Miss. Hunt explained handing him
the pink one to examine.
Hearing his Aunt loudly clear her throat, Bobby took the hint. "Oh
thank you so muc..much for getting me these pre...pretty bras," he
managed faking a smile.
"You're most welcome Bobbie. Now take off that cute play suit and I'll
bring you some pretty panties and camisoles to try on. Gwen, I think
Bobbie is old enough to begin wearing panty girdles. Do you want me to
get some? Okay be right back," Miss. Hunt said stepping out of the
room.
"Sh...she can't see...see me naked," Bobby gasped scared at the thought
and what might happen then.
"Don't worry. I'll send her off to get some pretty dresses while you
try them on," his momma said as Aunt Jo's smile got broader.
"As a matter of fact, I'll go with her to pick some really nice
outfits," Jo said.
"This girly stuff is way more than enough! I don't want any dresses
momma! Please can't I wear what I had on?" Bobby plead hearing that.
"You told me you hated that! No, a couple of nice dresses and some cute
skirts and blouses will do nicely. All young girls love pretty dresses
and skirts. When Miss. Hunt brings you some to try on, you better smile
and look really happy. If you don't, then she might decide you're a boy
and call the police," Gwen reprimanded sternly.
"Wearing a stupid bra and panties is bad enough but dresses? I don't
want to go to jail either so I can't let Miss. Hunt find out. This day
is going from very bad to worse. I'll pretend to be happy but I won't
like it," he thought then replied, "Okay momma."
"Got the little darling right where I want him. His fear of discovery
and the police will make him do whatever I say. Gwen is doing great
too. I told her to be unsympathetic and strict with him and she'd have
her daughter. Adding that bit about the police again was brilliant," Jo
thought listening to them argue before stepping out of the room.
##
Finally leaving the Tween to Teen Bobby was not happy. If he thought he
looked like a girl when they entered the store, there was no doubt now.
He was wearing his new white bra, white nylon full cut panties, white
panty hose under a white panty girdle. Three pale yellow net crinolines
flared out his new sunflower yellow sun dress. On his feet were a pair
of white kitten heels with a bow on the toes.
They had bought so many clothes Miss. Hunt said she would drop them off
on her way home later that evening. It took all his effort to stop the
tears from flowing. He hated everything he was wearing but the panty
girdle was the worst. It squeezed his boy parts severely and were hot.
By the time they got home he thought the same about the shoes. The
patent leather held in heat and pinched his toes. The heel was only one
inch but his ankles wobbled enough to worry him about falling down.
"Come on Bobbie, smile. It can't be that bad wearing such beautiful
clothes," his momma said with a big grin.
"Yes, it is. I'm a boy, your son, and shouldn't be wearing this...this
stuff," he replied with a sniffle.
"Look at it this way little Bobbie," Aunt Jo stated. "Looking so cute
no one will guess your little secret now. It's after twelve Gwen, what
say we stop at a caf?, get some lunch and Bobbie some Ice cream for
dessert."
The only thing good about lunch, as far as Bobby was concerned, was the
chocolate ice cream. Having to use the women's bathroom and his
lipstick reapplied another embarrassing event. He was mortified when
they entered another shop owned by another friend of Aunt Jo. There his
ears were pierced twice in each lobe. A small pearl stud with a gold
teddy bear just above were inserted. The woman piercing his ears said
that he should have had it done long ago and to stop acting like a baby.
"My goodness Bobbie, I know it didn't hurt that much. You're crying
like a baby," the woman admonished.
"You'd be crying too if you were a boy," he thought.
From that shop they entered another where the manager greeted Aunt Jo
warmly. This time Bobby walked out carrying a bag containing an emerald
green bikini bathing suit, sheer lime green wrap, pink flip-flops and
large brimmed straw hat. The top of the bikini was nothing more than
two triangles and thin strings. The full coverage bottoms had a white
frill of lace like a very short mini-skirt on the front. By this time
Bobby was totally exhausted and begged to go back to the house.
"It's such a beautiful day Bobbie but I see you're tired. We'll make a
short stop back at the photographers place to pick up the pictures.
We'll hang them in your room," Aunt Jo replied.
It turned out to be another humiliation, as he had to pose again for
more pictures. The worst was of him holding a curtsey, exposing the
lacy trim of his crinolines while the photographer snapped away. Before
they left, Aunt Jo purchased a scrapbook for him. The book had a white
leatherette cover with "My Precious Memories" written in pink scrip.
As Bobby was being photographed, the two women huddled off to the side.
"Well, are you happy with your new daughter Gwen? Didn't I tell you he
wouldn't fight it like you thought. You just have to be firm," Jo
stated.
"Yes and no dearest. Bobbie looks like a pretty girl but he doesn't act
like one. Although we told him to keep his legs together and take
smaller steps, he still moves like a boy. In the stores, especially
Tween and Teen, despite his forced smile didn't act like a girl. I'm
surprised no one said anything," Gwen replied.
"Oh, Hellen knew almost immediately. She figured it out when he didn't
act thrilled wearing his first bra. Nancy who pierced his ears also
knows. I don't think Gretchen at the swim wear shop did though.
Actually, this day turned out much better than I hoped. We know for
sure Bobbie is scared to death of being discovered. Plus we met a lot
of people today who only saw a cute little girl. Bobbie realizes that
and has to continue being one while he's here," Jo said with a giggle.
"What?" Gwen gasped. "They knew?"
"Don't worry about it. They are all very dear friends. They won't say
a word. Look I have another friend, Jane Tuttle. She's a retired
teacher but works part time instructing young girls how to be ladies.
I'm sure she will have no problems with Bobbie," Jo answered.
"Jo, my darling, you always have the right answers and such a comfort.
No wonder I'm head over heels in love with you," Gwen gushed giving Jo a
kiss.
"Just leave everything to me Gwen. Let's go home and help Bobbie put
away his new things and pack up all his boy clothing. We don't want him
thinking about running away," Jo said.
When they got back to the house all Bobby wanted to do was get out of
his horrid girly clothing and wipe the lipstick off his face. He was
naturally upset when his request to change was rebuffed.
"Look little Bobbie you can't do that. Everyone who saw or talked to
you think you're a precious little girl. What do you think would happen
if one of them saw you in boy's clothes? You don't know? Well they
would get very angry at being tricked and could call the police. You
wouldn't like that I'm sure. Let's go to your room and put away all
your nice new clothing then hide your boy stuff. We can't take any
chances your secret gets out. Remember Miss. Hunt is coming over to
bring all the things you got today. She's going to see your room and we
can't have your boy clothing where she can see them. Okay," Aunt Jo
explained.
As his mind absorbed what she told him, fresh tears began falling.
"I..I don't wan...want to be a....a girl," he replied.
"Sorry Bobbie but you don't have any choice now. Just for the summer,
you're going to have to the bestest little girl possible," his momma
said taking his hand. "We need to pack your boy things before Miss.
Hunt shows up, come along and help."
"Oh man, I don't like this at all. I'm not a silly girl. Momma's right
though. Everyone did think and treat me like I was a girl today. She
did say just for the summer. All summer! That's almost like forever
but I have to do what momma says," he thought letting more tears flow.
After supper Miss. Hunt arrived and all of them helped unload her packed
car. He was left in his room with his momma to help either hang or fold
the clothing. Jo and Hellen went to the kitchen where over a glass of
white wine, she showed Hellen Bobby's scrapbook. The first page had the
napkin with his first lip imprint. Under it he had been forced, using a
pink pen to write, "My first time wearing lipstick. I just love it. I
hope momma lets me wear it all the time now that I'm a teenager." The
second, had the picture of him hugging the teddy bear. It was
captioned, "I love my teddy but I'm a big girl now." The next page had
the box his first bra came in. Under it was written, "My very first
bra," followed by a series of pink hearts. "I'm a big girl now and
can't wait for my boobies to grow." Underneath that box was the label
off his white nylon panties. Bobby wrote, "My first big girl panties.
Oh how wonderful they feel. So much prettier than my old cotton ones."
"Oh my, how did you get him to write that stuff?" Hellen asked.
"We just gave him a little encouragement," Jo replied. She didn't tell
Hellen it took several swats of the hairbrush.
"Are you forcing him to do this?" she questioned.
"Not really Hellen," Jo replied to remove any suspicions. "You've seen
how some young teen boys act when they're brought into your store. His
mother just wants to curb that rambunctious behavior before it gets out
of control. She and I agree spending the summer on the softer side will
do that. That's all. Although after today's experience, I think he may
actually like it. He only raised a token resistance all day. You
should have seen him smiling happily posing for Jack in that pretty
sundress we bought today. I'll bring the photos over when we pick them
up. I also caught him several times looking at his reflection in the
shop windows and smiling. I'm beginning to wonder if she'll be able to
get him back into trousers when they go home."
##
After a troubled sleep Bobby was awakened by his momma. "Get up Bobbie.
you have a busy day today. If you are going to keep your secret, you
must learn to act like a girl. Aunt Jo has a very good friend that can
teach you how to properly behave so the police won't be called. You are
much too boyish in your mannerisms. Somebody will guess your secret
before much longer if you behave like a boy," she argued.
"But momma can't I stay in here? I don't want anybody seeing me dressed
this way," he pouted.
"You can't stay cooped up in the apartment all summer! Your Aunt Jo and
I don't intend to stay in here all the time. This is New York City and
there are just too many places to see. There's no way we are going to
let you stay here by yourself. So get used to being my little girl
until we go home. Come, out of bed and follow me into the bathroom,"
she stated.
"I can take my own shower," he whined. "I was going to have so much fun
this summer. Even going camping but now I can't wait for summer to be
over," he thought.
"You're a girl for the duration. You will be having a nice bubble bath
from now on. Unless you want me to bathe you like a baby, stop arguing
with me!" Gwen snapped.
"Does it have to be a bubble bath?" he asked smelling the strong scent
of flowers coming from the rising water. The pretty bubbles didn't
bother him so much it was the scent.
"That's it! I told you to stop arguing with me! I should get my
hairbrush...but instead I'm going to shave the hair off your legs and
the little bit under your arms. Maybe that will teach to do what I
say," she angrily replied.
"Shave my legs? My underarms? I just started growing hair there,"
Bobby thought in dismay.
He was depressed by what his momma did in the bathroom and it took all
his effort not to burst into tears as she dressed him. First, he took
his new violet nylon and chiffon baby doll nightie and matching white
lace ruffled panties, folded them and put them under his pillow. His
new sleep bra had already been put into the clothes hamper.
Standing naked with hands covering his groin, she handed Bobby a pair
of bright yellow nylon panties with small daisy print to put on. A
yellow satin training bra with molded cups and slight padding was next.
Bobby had problems hooking the single hook and eye fastening until Gwen
pulled his hands in back and guided his fingers. Ecru pantyhose was
kneaded up his legs followed by a muted yellow with bright yellow center
panel girdle. A pair of white satin pointed toed pumps with a one-inch
stacked heel were put on his feet. They pinched his toes while wobbly
could walk in them.
"Put this on and come into my room. I'll take those curlers out and add
a little makeup," she ordered handing Bobby a translucent pale pink
wrap.
Gwen didn't use much makeup. Just some mascara, rose blush and coral
lipstick. Using a floral scented perfume put it on his wrists, neck and
behind the knees.
"Momma do I have to wear this much makeup? I don't like how lipstick
feels. It's all sticky," Bobby complained looking at what his momma had
done.
"You should be thrilled. Besides getting her first bra wearing makeup
is a girl's fondest desire. It means that they are no longer little
girls but big ones," Momma replied.
"But I don't like it," he began to protest.
"Bobbie, it's that kind of attitude that'll get you discovered as a boy
wearing a dress. Do you really want that? If that happens soon
everybody will know, maybe even your school friends. Worse they might
call the police. So stop giving me grief over this and behave. It's
only for the summer," Gwen replied.
"I didn't think about that. If my friends find out. I can't let that
happen!" he thought.
##
An hour later Bobby, momma and Aunt Jo were standing in front of an
apartment door. "Now Bobbie, unless you want everyone to know you're a
boy wearing dresses make sure you listen carefully to Miss. Tuttle,"
Gwen said as Jo rang the doorbell.
Bobby was scared and uncomfortable. He was about to meet another
stranger and hated what Miss. Hunt had brought for him to wear. It was
a black wool blend, satin lined pencil mid-thigh skirt and pale yellow
semi-sheer blouse with puff short sleeves. His bra clearly visible and
the skirt made him take short steps.
"I hate this," he thought. "I'm going to meet someone who is going to
teach me girlie lessons. That's all I need. Any more of this girlie
stuff and I'm going to croak."
Miss. Jane Tuttle was born in 1900 and began her teaching career in
1920. She taught at a posh girls' school until her retirement in 1960.
Jane was also a confirmed lesbian after meeting Donna, an older teacher.
They became lovers until her death four years ago. She was a strict
teacher and the students all thought she was very old fashioned. For
her part, Jane thought the girls were undisciplined and ill-mannered. A
teacher's retirement pension wasn't great so took a part time job.
There were still parents out there that wanted their daughters taught
real manners and decorum.
Jane was five foot eight in two-inch block heels. Grey hair in a tight
bun at the back of her head, fierce looking black eyes and stern
demeaner. She was wearing a creme colored long sleeved blouse tucked
into a pair of khaki pants with a narrow black patent belt as she opened
the door.
"Jo it's so nice to see you again. Please come in," she greeted.
After introductions were made, Jane offered the women a cup of coffee
while she explained what she would be teaching Bobbie. "I prescribe to
older traditions and teach from the four Nancy Taylor Courses.
Graduates, I can assure you will: Have model manners and etiquette,
exude personal daintiness and poise, have attractive behaviors and
traits and exhibit charm and glamor. Does that sound like what you
desire to bring out in Bobbie?"
"Perfect!" exclaimed Jo.
"How long is the course. We're just here for the summer." Gwen asked.
"Well, usually twelve weeks to properly teach the first course, poise,
daintiness and mannerisms. However, in your case, provided Bobbie can
come four days a week instead of two. Let's say from nine to noon every
day except Friday and the weekend, she should meet most of my standards
in six," Jane answered.
When momma and Aunt Jo came to take him home, Bobby was more than
willing. After three hours of intense work, he had more girly training
than he ever wanted. He spent most of that time memorizing the rules
for perfect posture then practicing it.
The rules for perfect posture dictated that the ears- centered over the
shoulders, chin- parallel to the floor, shoulders- down and relaxed, rib
cage- elevated all the time, stomach- pulled in and taut, pelvis- tucked
in and tilted slightly forward, knees- relaxed and slightly flexed, and
feet- weight rest on the center of the foot. Bobby really didn't like
the chest requirement as it made his blouse stick out. It was bad
enough the bra could be seen through the thin material but now it looked
like he had real breasts. Trying to keep his body positioned as required
was very hard work especially when mincing in the tight dress. At
first, he didn't try hard enough and received a harsh reprimand
including a swat to his butt. Miss. Tuttle carried a walking cane and
didn't mind using it for encouragement.
After an hour of just standing assuming the correct posture, she had him
walking. He had taken no more than three steps, when she swatted his
butt and instructed, "Swing your legs from the hips, landing toes first
then the heel. High heels aren't designed as a stable platform and
easily slip if planted first. You must always be aware of the surfaces
you are walking on. Wooden or linoleum floors can be slippery, carpet
can snag a heel and cracks in concrete can trap one. Now elbows in,
relax your wrists and back straight. Take small dainty steps, head up!
Chest out!"
When Aunt Jo and his momma entered the house to pick him up, Jane had
Bobby demonstrate what he had learned. "Notice the improved posture
already. It's essential that you make sure she maintains it all the
time. By doing that, muscle memory will make sure she never lapses in
the future. Since we've agreed not to do courses on a beauty regimen
and makeup, I'll give you a copy of book two. It won't hurt Bobbie
learning basic skin care and a beauty routine at her age. For our next
session, I want her wearing a full skirt, crinolines and at least two
inch heels. We're going to start skirt management lessons," she told
them.
"It's bad enough to do this here but all the time? I don't want to
learn beauty care either or skirt whatever," Bobby thought.
As soon as Bobby started walking back to Jo's brownstone he let his
shoulders stoop. That way his bra covered chest wasn't as noticeable.
He wanted to stretch out his stride but the tight skirt prevented that.
"Bobbie! Shoulders back, chest out like you were taught!" Aunt Jo
snapped.
"If I see you doing that again, I'll get my brush," his momma added.
The rest of the walk was silent except for the click-clacking of women's
heels on the concrete. Bobby concentrating on his posture didn't notice
a large crack in the sidewalk. His right heel caught on the edge,
stopping foot movement and would have fallen if Aunt Jo hadn't been
watching him. She reached out and grabbed his arm before he could fall.
"Bobbie, watch where you're walking. You could have broken an ankle,"
she admonished.
"I wouldn't have to watch if I had my sneakers on instead of these
girl's shoes," he mumbled.
His day only got worse. As soon as lunch was over, his momma and Jo
began teaching how to sit and stoop like a girl. They weren't happy
seeing him sitting with his legs stretched out as far as the skirt
allowed. Aunt Jo came up with the idea of putting a quarter between his
knees every time he sat. If the coin fell to the floor he received a
slap to his bottom with the hairbrush. Later as he prepared for bed
Bobby was taught a night time beauty regimen.
"Why are you making me do all this when in the house. Nobody can see
me. I only have to look girlie when you make me go outside?" he asked
getting into bed.
"Because you walk and act like a boy in girl's clothes, that's why.
We've already had this discussion this morning. Do you want to totally
embarrass me, Aunt Jo and yourself? Maybe you want to be discovered as
a boy in a dress. Is that it? You want to go to jail too?" his momma
demanded.
"No, no it's just....," he began with tears beginning to flow only to be
cut off.
"Well! If you don't do your best to learn what Miss. Tuttle and we are
teaching you, someone will. What we taught you tonight was rudimentary
but Miss. Tuttle will refine it. Get some rest. You will have another
busy day tomorrow," she interrupted.
##
After weeks under the tutelage of Miss. Tuttle, Bobby made a lot of
improvement in his feminine mannerisms and posture. He was obviously
unhappy and it showed on his face. He was still resisting Aunt Jo and
Gwen's efforts to make him act more like a girl. Only the threat or
actual use the hairbrush made him fully cooperate.
"Gwen baby, we simply have to do something about Bobbie's attitude. I
was thinking, what if we go to Cape Cod for the weekend. I have a dear
friend, Darla and she has a place in Provincetown we could use.
Provincetown is one of the few places where our lifestyle isn't a
problem. We can be more open in our relationship and spend time on the
beach," Jo suggested.
"That sounds like a great idea Jo but what does that have to do with
Bobbie's attitude?" Gwen replied snuggling closer to Jo on the couch.
"Everything darling. Instead of making him look like a pretty girl
we'll let him be a sissy boy. No one there will raise objections. It
has a very large artist colony, writers and actors as well. It just
might change that sour puss attitude of his," Jo responded.
"I don't know Jo. I've told you if we went through with this I wanted
him to pass as a young girl. No one has questioned that he was a boy in
a dress here," Gwen responded feeling uncomfortable about the idea.
"I know dearest but remember I love you. I realize it could be
embarrassing and maybe a bit scary. I wouldn't have suggested
Provincetown if it wasn't accepting of such things. Most of my friends
go there in the summer. While there may be a few bigots most won't pay
us any attention. They're very accepting. Bobbie is more scared of
being seen as a sissy than he is as a girl. Making him a sissy for a
couple of days should be the motivation we need. Let's give it a try
and if you have any problems, we'll stop, okay?" Jo argued.
##
"It's a shame Darla couldn't get away from work. You'd really like her.
So what do you think?" Jo said after everything was unpacked from Gwen's
car.
"It's so lovely here and right on the beach too," Gwen gushed. "I can't
wait to get out there by the water."
"Well my love, why don't you go change and I'll get little Bobbie
ready," Jo responded kissing Gwen on the check.
"I'm not going out there like this!" Bobby screamed.
"Oh yes you are!" Jo hissed. "I'll take you out there if I have to drag
you. Then outside I'll use your mommy's hairbrush until you can't sit
down."
They hadn't set his hair. It hung in loose soft curls making him look
more boyish. He was wearing the emerald green bottoms to his bikini, a
pair of pink flip-flops, and the sheer wrap. The only makeup was a
bright red lipstick and matching varnished nails. Without the panty
girdle, there was a very distinguishable bump in the bottoms.
"But I look like a boy dressed like this," he pouted.
"No, you look like a sissy! Never the less, you're coming to the beach
with me and your mommy," she stated smiling in triumph. "I can't wait
till he grows up. If he stays this cute I'll make a fortune," she
thought.
Bobby was blushing the entire time they walked along the crowded beach.
They stopped frequently, once to see a beach volleyball game where he
heard a few snickers. At another stop a very butch looking woman
pinched him on the cheeks and told him he would have all the young boys
chasing him. What made him cringe was when she told Aunt Jo and his
momma about a special teen hangout.
"Man, I don't want to go anywhere especially that hangout she was
talking about. I don't want any boys chasing me either," he thought as
they walked on.
Later that evening after his bubble bath, his momma dressed him in a
pair of tight fitting white short shorts, a pink cap sleeved nylon
blouse and black ballerina flats. The hem of the blouse was tied off in
a bow knot just under his breasts. Bobby's only underwear a pair of
pink nylon panties. Gwen left his hair in loose hanging limp curls and
making him apply red lipstick. Even then, you could tell he was a boy.
The tight shorts showed visible panty lines but also the bulge in the
crotch. He fussed and complained that he looked like a bigger sissy
than in his bikini bottoms.
"You only have yourself to blame Bobbie. If you acted more like my
precious daughter it wouldn't have come to this. Maybe when we get back
to the city, you'll have a better attitude. Besides when we leave
Sunday, you won't see any of these people again," Gwen said as she stood
watching them.
It wasn't until Gwen told him she was taking him to that teen hangout
that he dug in his heels. "No! I won't go!" he screamed.
He still had some tears in his eyes as his momma pulled up into the
hangout's parking lot. Taking a tissue blotted his eyes said, "Bobbie,
I will go in with you and make sure the place is well chaperoned. If
you behave and if you dance with anybody who asks then I will stay. If
I see any bad behavior I will just leave you there on your own. With me
there you will know you won't get into any trouble. So, do we have a
deal?" she said.
"Dance? Even if it's with another boy?" he gasped.
"Of course," she answered. "Even the slow songs and if he tries to kiss
you, you will let him."
"Kiss me! No way," he shouted only to get a slap to the face.
"If you don't do exactly what I say, the boys just might try to do more
than kiss you! That is, unless I stay to make sure nothing more than a
little kissing happens. What's it gonna be?" she stated. "I don't like
this any more than you do but Jo insisted," she thought.
"I can't let her leave me here! I don't want to dance with any boys
much less kiss me but if I don't. No telling what will happen if she
leaves me here alone," he thought then stammered, "O...okay, bu...but
I...I won't like it."
Gwen knew the place was safe and the kids carefully watched but Bobby
didn't. When they entered, she gave him some money and pointed him over
to a small table with two chairs. Then she went over to the adult's
section where Jo was waiting.
"How'd it go?" Jo asked.
"He was a bit difficult but he's here," she sighed. "Are you sure this
was a good idea? You know how much I want a daughter....not...not a
sissy."
"I'm sure we did the right thing. After this weekend, little Bobbie
will be more than happy to be your daughter. Trust me on this my
darling," Jo replied.
It had been a horrible frightening night for Bobby. It seemed like all
the boys wanted to dance with him especially the slow ones. Most of
them giving him a kiss to the neck or cheek. Some, bolder, kissed him
on the mouth. One husky youth stuck his tongue into Bobby's mouth
giving him a deep soul kiss.
"For a sissy, you need to learn a lot about kissing. Maybe I'll see you
around and give ya some free lessons," the boy said as he walked Bobby
back to the table. As Bobby moved to sit, the boy gave his butt a slap.
"Maybe you'll let me teach you some other things," was the boys parting
shot.
Other than the rare kiss from his mother or more frequent ones from Jo,
he had never been kissed before. He hadn't danced before either and
upset that it had to be with other boys. The big one who slapped his
butt scared the living daylights out of Bobby.
"I can't believe I'm actually kissing and dancing with boys. When that
boy stuck his tongue into my mouth I almost lost it. If I'm going to be
dancing and kissed I'd rather it be with some girl," he thought.
When his momma saw what that bigger boy did came over and told him it
was time to go. Bobby jumped up so fast the chair fell to the floor.
Leaving they didn't see Jo handing out money to the boys that had danced
with him. It wasn't until they got home that they noticed the hickie on
his neck. That and what had happened made Bobby break out in a flood of
tears.
"You only have yourself to blame," his momma stated. "If you were a
girl, they would have respected you more and been gentlemen."
##
It had been a very traumatic weekend for Bobby. Back in the city it
didn't get better but he was a more willing participant. When he lapsed
in any of his feminine manners or behavior, Aunt Jo or his momma
threatened to put him into boy clothes then take him out wearing full
makeup. He hated dressing and behaving like a girl but it was a relief.
Being accepted as a real girl was so much easier and safer than a sissy.
He decided to do his best until his momma came to her senses and let him
be a boy again.
"School will begin soon and momma has to let me go as a boy. All I have
to do is put up with this until then," that thought kept him going.
Near the end of August Gwen and Jo sat talking about the future. "Jo
dearest, don't get me wrong. I appreciate all you have done for me and
Bobbie but...I can't let you pay for everything. I still have the house
in Jersey. I just can't leave it vacant much longer and hope it already
hasn't been stripped bare. I need to find a job too. I love taking
care of the apartment for you and everything but it's boring. I need to
express my artistic talents and contacted the ad agency I worked for
ages ago. They agreed to hire me back the second week in September as a
copy writer. Besides I must get Bobbie back into school. It's not like
we'll be separated. You still have the salon in Jersey and my office is
here in the city. We can still have our time together," Gwen said.
"My darling you know I don't mind seeing that you and Bobbie are taken
care of. However, we are both liberated women and need to know we can
make it on our own. I understand where you're coming from. I will miss
you staying with me dearly but you're right. Taffy is quite able to run
the shop here. I'll schedule more time to be at the Jersey salon.
Since you'll be working and commuting, I can baby sit Bobbie when he
comes home from school. We can go back to my place on weekends.
"Thank you for being so understanding my darling. You're such a dear
and keeping an eye on Bobby is a great relief. She'll, I mean, he'll be
fourteen soon and you know how terrible teens can be if left on their
own. Gawd, I'm going to miss my darling daughter so much. How I hate
the way things are where I can't have her all the time," she replied
then began crying.
"Don't worry Gwen, my love. I'll see that Bobbie doesn't develop into
one of those dreadful teenaged boys. Come give me a hug," Jo
compassionately said. "I can't wait to get my hands on him. I
guarantee he won't develop into a real boy. I'll have him working in my
salon mincing and prancing around just like he's doing now. He might
have to look all boy at school but not in my salon," she thought.
The best thing about his momma going back to work for the ad agency, she
began dressing again. Thanks to Aunt Jo's money, Gwen was now always
dressed to the nines and wearing full makeup. Bobby thought his momma
was a very beautiful woman when she dressed up. When he had to wear
girls' clothes during the summer she would hug him a lot, he liked that
a too. Momma was a beautiful woman and always wanted her affection.
S