A Bouffant for Billy
By Darlene leQueen
Billy was nervous to say the least as he sat at his mother's vanity
dressed in a pair of her ruffled frilly pink panties ad a lacy pink bra
and one of her frilliest baby doll night gowns trimmed with marabou fur
all over. "Now Billy, I told you time and time again if your grades did
not improve by your last report card you would be punished, did you
think I was kidding?" "Your grades have not improved at all." His mother
snapped as she retrieved from her vanity drawer a basket of ? inch wide
pink hair rollers, some pink roller picks and a jar of Dippity-do
setting lotion.
"I'm happy you decided not to cut your hair Sweetheart, because it's
going to work out even better now." "It's a very good length, very long
excellent now for setting, curling and teasing up." "I'm sure Aunt Carol
and I will be able to try lots of really pretty hairdo's on you." "After
all you are going to be a very sweet and sexy little lady this summer
aren't you"; she said placing the basket filled with the pink plastic
rollers in her son's lap. "Aunt Carol and I will see to that." "In fact
you're going to quite the little blonde bimbo." "That's your punishment
for such terrible grades, your lucky I talked them out of summer school
or leaving you back a grade." "You barely made it by, they were going to
leave you back." "Instead I convinced Mrs. Walker your guidance consular
that a summer dressed as a woman is a far better punishment and she
agrees that should straighten you out and make you pay more attention
and teach you some better discipline."
Billy reluctantly nodded his head in affirmation as his mother began
combing his wet shoulder length hair with gobs of the fragrant Dippity-
do setting lotion. Once she was satisfied that his hair was evenly
saturated she parted it down the middle and began to pull out a swatch
of hair from his forehead. "Now hold still, I've got to get your bangs
nice and even." She proceeded to cut her timid son's hair until he had
what looked like a cute girlish bob, blunt cut a little shorter in the
back gracefully falling forward to kiss his cheeks as his brand new
bangs tickled his face. "Now lets get you all set and netted so we can
both get some sleep, it's been a long day and I've got a feeling
tomorrow is going to seem even longer to you."
Billy was thirteen years old and much too slight of build and weak to
even think about challenging his mother physically. She was much larger
and very imposing. He knew that whatever his Mother wanted to do to him
she was going to get her way so there was no sense resisting her. After
all he was warned about his grades and the consequence of failure. He
just couldn't have imagined a punishment a bad as this or he surely
would have done better. That his mother would dress him up like a girl
for the entire summer. Knowing what he knew now, summer school or being
left back now seemed like a better choice. But then again it was where
all the tough boys went that usually failed and went to summer school,
and they'd probably be beating him up every day and calling him sissy
anyway, so perhaps he was safer and better off here in spite of his
Mother's plans. At least here he'd be protected from all the others.
Billy's father worked on long term oil contracts in the Far East & was
only really home for 2 months every year so his mother was his guiding
light
"Have you picked out a name yet darling", Billy's Mom asked as she
selected a swatch of hair from his crown, combing it up with her rattail
comb. "I know Billy could be a girl's name if we spelled it differently
but I want you to have a more sweet feminine sounding name if you're
going to be dressed like a girl." "I'd like something really feminine
sounding." "Now hand me one of those curlers, one at a time, then a pick
just like beforehand." "Now pay attention, your going to have to learn
how to set my hair as well as your own." "I'm not going to do this every
night for you, you know." "You're going to learn how to do it to me."
Billy handed his mother a pink roller as she stood behind him quickly
winding it down tight against his scalp, then snapping her fingers she
ordered, "Come now where's the pick young lady, we haven't got all
night." Billy felt the curler dig into his head as the plastic roller
pick held the curler firmly in place. "Come now Billy another roller
please, let's get this show on the road." Each curler was tightly wound
down adding to his discomfort. The curlers pinched like the devil and
they pulled tightly at his scalp. She wound them in as tight as possible
smiling at his new feminine discomfort. The little pink picked only
added to the pain pinning the tight pink curlers into place. Why did his
Mother have to make them so tight? It even seemed like she was purposely
making those picks dig into his scalp.
Billy's mother already had her hair up in curlers, earlier she was
seated at the vanity setting her own hair. As Billy had being ordered to
stand motionless beside her. He stood by mortified watching while he was
wearing one of his Mother's panties, bras and nightgown & some really
nice pink lipstick. Handing her roller after roller listening to all the
things she now expected of him. She fully intended for Billy to spend
the entire summer working in his Aunt Carol's beauty salon as a beauty
assistant. He was to learn the art of hairdressing, make-up, and even
nail salon care. Skills she knew would keep him out of trouble and
secures a future for him financially and as a girl she could easily keep
an eye on him. That was his punishment for the summer to work in Aunt
Carol's Beauty salon as a salon girl.
Besides the fact that she had always wanted a daughter to dote on and
share her feminine knowledge with, she also fully intended to keep him
in dresses, curls and lots of makeup for as many years as possible
progressing one month at a time. Her plan was to turn him into a
complete sissy bimbo slut. She wanted him totally feminized and
sissified as soon as possible. And while she told him it was only for
the summer, he real plan was that he would never leave his feminized
state.
And if you thought his Mother was bad, you should see his Aunt Carol her
sister who had dedicated her life to the pursuit of the feminine arts.
While she drops dead gorgeous, she could be absolutely wicked and evil.
Aunt Carol's only interest in life was big beautiful hairdos, lots of
makeup, glittering jewelry and very sexy feminine clothes. He surely was
in for much worse feminization from her. Little did he know her love for
heavy makeup, big hairdos and sexy clothes was only the prelude to the
real things she and his Mother planned?
As Billy sat watching his hair being put up in pink curlers for the
first time he really could not believe what was happening to him, did he
really have to think of a girl's name for himself? "Now Sweetheart you
are going to experience something few boys ever get to feel." "The
feeling of sleeping in a soft sexy very feminine nightie, with your hair
up in pink curlers." "Girls have to sleep with rollers in their hair to
look pretty in the morning." "So I think it's only fair that you should
know what sleeping in curlers are all about." "Aren't you a lucky boy to
experience this wonderful feminine process."? "Mother and Aunt Carol
will teach you all about the joys of sleeping in pink curlers just like
a girl." "I know it seems to hurt a lot right now, but eventually Aunt
Carol will teach you to love it, even the love the discomfort."
"Sleeping in your pretty pink curlers will help you feel very girlish
and feminine." "And believe me we want you to feel like the most
feminine salon girl in the world."
"Aunt Carol will be over first thing tomorrow morning to comb both of us
out, so we will both have pretty hairdo's while we go dress shopping for
you." "You'll need everything of course, panties, bras, shoes, oh my god
it will take weeks of shopping to get you completely outfitted like a
proper sexy lady", she squealed as she finished winding a roller at the
back of his head. His Mother made it sound so glorious sleeping in with
a head full of pink curlers. He didn't think it sounded very comfortable
at all and he didn't see how Aunt Carol could make him love it, but
that's what his Mother had said.
"What about Priscilla?" "I think that is an adorable name for a girl",
his mother said as she snapped her fingers ordering up another roller.
"Well if you don't pick a name I will, and I think Priscilla suits you
perfectly." "Heavens me I have a sweet little girl all of a sudden." "We
are going to have so much fun." "You have so much to learn about
walking, talking, thinking and acting like a girl." "That's one of the
reasons I want you sleeping in curlers darling is so you will dream
about all the pretty hairdo's we are going to give you." "Lots and lots
of teased up and lacquered bouffant hairdos." "Just like Aunt Carol does
to my hair and hers sweetheart."
"Aunt Carol is an absolute genius when it comes to creating the biggest
most teased up bouffant hairdos imaginable." "Oh my, she even adds fancy
wiglets, falls and other attachments for special occasions when we want
really big hairdos." "She sometimes combines two wigs into one for a
massive effect." "Big bubble flips and beehives like Aunt Carol wears,
you won't believe how your life is going to change, I think it will all
be for the better darling."
Billy's mother cooed in his ear as she kissed him sweetly on the cheek.
She was dying to kiss him on the mouth but Carol had suggested she wait
and move slowly with their plans. "Aunt Carol has promised me she'll
give you some of the biggest teased up hairdos she's ever created."
"She's really going to pull out all the stops to turn you into a little
bouffant Princess." "You know she has so much experience in that area."
"She styles wigs for all the local drag queens and they always want the
biggest possible hairdos so she knows her stuff." "Of course she is an
expert at makeup and long feminine nails too." "I think you're going to
become a VERY glamorous lady my dear."
"My sweet, sweet Priscilla, oh my how I just love that name for you, my
darling little girl." "What a sexy lady you are going to become under
our careful guidance." "Now enough of this talk and hand me another
curler so we can get you all set." Billy sat speechless as his Mother
continued setting his hair, rolling those horrible pink hair rollers
into his hair tightly. They were so tight his head was now throbbing in
pain and he felt a headache coming on from the discomfort to his scalp.
The picks she added only pinned them down tighter. "Mom do the hair
curlers have to be so tight", he sheepishly asked.
"Of course they do sweetheart a nice tight set will give you a marvelous
curls in the morning." "Just you wait and see, you will have body to die
for." "With your thick hair I think Aunt Carol will be able to give you
more height and volume when she teases you out", his mother replied
patting her own pink curlers with her long red nails. Billy watched her
feminine gesture as her long red nails slide across her head patting the
curlers into place and checking their tightness and position.
As Billy handed his mother what would be the last roller in his first
set she sighed and exclaimed, "There you go my darling Princess your
first curler set." "What a pretty girl you make, just look at yourself,
not a hint of make-up apart from your lipstick and you already look like
an feminine angel", she said kissing him to his surprise very
passionately on his lips. A long lingering passionate kiss that
surprised Billy and also took his breathe away. She smiled at him seeing
he liked it and kissed him passionately again. Without a word she picked
up the can of Aqua Net hard to hold hairspray and began spraying her
roller set all over.
The room filled with the feminine scent he associated with his mother
and Aunt Carol. "Now let's get your set sprayed too Priscilla, here sit
still and cover your face darling." She then began to thoroughly coat
the poor boys hair rollers with what seemed like and endless amount of
the sweet smelling lacquer" "Okay Princess you can put your hands down
now." "Let's get you netted and scarfed and we can both go to dreamland
and dream of all those adorable hairdo's you most certainly will have
and love." "Because all girls enjoy being all dolled up and pretty."
"Girls always dream of going to the beauty salon and getting a full
salon beauty makeover." "And Mother is going to make sure you're always
all made up, styled and looking very pretty." "You'll be quite the sexy
little lady."
Carefully floating a shear pink net onto her own set she tied it off at
the nape of her neck.
"See how this is done Darling." "Careful not to snag it, now hand me
that pink scarf." "There should be one for you and one for me." Billy
leaned over to reach the feminine cover up as his mother spritzed him on
the neck with her perfume." "Now you smell just like your Mother baby,
now hold out your wrists like this, good girl, good, good girl", she
continued spraying her son with her heady feminine fragrance.
"Now I want you to sleep in here with me until Aunt Carol and I can
redecorate your room more appropriately for a girl." "I just don't see a
pretty woman like yourself in a room full of baseball poster, now do
you." Billy just hung his head in humiliation, shame and acceptance and
nodded as his mother fussed with his hair net and scarf. Tying them off
just like hers with a pretty pink bow atop his forehead. "I think we can
get Aunt Carol to find you some really sweet hairdo posters, the kind
she has at her beauty shop." "Those kinds of pictures will be much more
suitable for your new room."
"Yes, lovely posters of gorgeously made up and styled older women." "It
will do you good to be surrounded by posters of sexy women like that
with fabulous teased up hairdo's and extensive make up." "These are the
ladies you will long to emulate my dear & in fact I intend to make you
look much,much older than your years with mature ladies make up & hair"
"They will go much nicer with your new vanity and furniture." "Perhaps
if she searches really hard she can even find you posters of some
beautiful glamorous men dressed as women." "Wouldn't be nice dear
posters of glamorous drag queens or female impersonators gorgeously
gowned and dripping diamond jewelry and all made up with big teased up
bouffant hairdos." "That would be quite appropriate for a sissy girl
like you whose about to become a drag queen herself." "You can look at
those posters and dream of the exotic beautiful queen you'll one day
become." "You can dream of the many admirers you'll worshipping your
glorious feminine beauty."
"They you are sweet pet, all set and kerchiefed like a pretty feminine
dolly." She could resist her passion no more because he looked so
adorable all set in pink curlers. "And now sweetie Mother has one more
lesson for you to learn before you go to bed as a girl for the first
time." "A lesson Mother is going to repeat many, many times my
precious." As he stood up, his Mother put her arms around the pretty
slight teen and kissed him passionately again several times. Her
lipsticked lips imprisoned his mouth as her arms held him firmly in
place.
He couldn't believe it, here he was making out with his own Mother while
they both had their hair set in pink curlers wearing ladies nightgowns.
She continued to kiss him passionately caressing his feminine nightgown
and bra and caressing his pink curlered head. It felt so strange to be
kissing his Mother like that with his lipstick ''mingling'' with his
mother's beautiful lipstick, but it also felt very good. Her sweet
lipsticked lips pressed to his felt divine. God she was so exciting, he
wanted to go on kissing her forever. If she wanted him to be a girl and
this was his reward to would shamefully accept it.
She sat on the edge of the bed and forced the boy physically to his
knees in front of her. "Now it is time to learn something else feminine
darling, how to please a lady." "Little sissy boys who have their Mommy
dress them all up like girls should have their adoring son learn how to
service Mommy." "Pull Mommy's panties down gently sweetie." When he
hesitated she slapped his face her long red nails raking across his
cheek, "Do as I tell you Priscilla", she commanded. She slapped his face
several more times lightly, "Do it little sissy girl." He was so shamed
he was now about to commit an act he had vaguely heard boys at school
talk about, but he knew resistance was futile. He would have to submit
to her. He slowly pulled her panties down. "Now kiss Mommy's pussy
sweetie, make Mommy feel good. Oh hang on for a moment while I re-
lipstick your lips" She reached over & picked up a tube & slowly uncased
the matt red lipstick. '' Steady now my Darling while Mummy paints you
lovely lips with this gorgeous lipstick'' Her hands were slightly
trembling has she applied the fabulous red lipstick to her Darling son's
waiting lips'' That's so nice, my sweet, you look stunning in red
lipstick & I think this will be your color to pleasure your Mummy''
Her hands were on the back of his neck propelling him forward, he was
too weak to resist. He accepted his shame and humiliation and kissed her
pussy sweetly, "Again darling, more, your doing fine." His friends had
talked vaguely about boys doing this for their girlfriends. He kissed
her pussy again. He'd expected it to be distasteful but it wasn't it was
rather lovely. His Mother looked so pretty even in her curlers just like
him. "Now baby stick your tongue out and lick Mother's pussy with your
tongue, go on girl, lick it for Mommy and show her how much you like
making love like a girl." "Dream of Mother helping you to become a full-
fledged woman just like her and Aunt Carol."
Somehow it tasted slightly like strawberries, he liked it. He didn't
know his Mother had purposely used a strawberry douche to make it taste
sweet. He licked his Mother's pussy enjoying it more and more. His
Mother was in ecstasy as her sissified son pleased her orally. Once he'd
developed a rhythm she let go of his neck, he keep right on licking her
in obvious pleasure. He began for the first time to taste his mother's
love juices and from this moment he knew that his future role was to be
a Sissy lady's pussy licker
When he glanced up, his Mother's hands we softly caressing his pink
curlers and kerchiefed head with her long red nails and she was moaning
softly. She ran her hands over his pink curlers over and over moaning in
feminine ecstasy while caressing his pink curlered head. He must have
been doing it right because she looked like she was in heaven. He
redoubled his efforts until his Mother was squealing in feminine passion
and she was gripping his curlered head tightly. Looking down at her
son's curlered head and kerchief she came several times gripping his
curlered head tightly. "Oh Priscilla, what an adorable sissy lover you
make for Mommy." "My own little lesbian love doll better than any
woman." Finally he screamed from the pain of her crushing his head and
she let go.
"I'm sorry Priscilla darling, Mommy got so carried away she didn't
realize she was hurting you that much sweetie." "Do you forgive Mommy
darling?" "Yes Mother, I'm sorry I screamed, but you were hurting my
head." "I'm sorry too darling, but you were doing such a wonderful job
of pleasing Mommy I just got carried away." "Did you really like it
Mommy?" "Oh yes my darling, you did a wonderful job, and for your first
time too, surely you'll become even better as you gain experience."
"Mommy is VERY pleased with you." "Perhaps you can learn to please Aunt
Carol in the same way." "I'm sure she'd adore it, having Priscilla
please her." "Would you like doing that darling Priscilla?" "Yes Mommy
if you want me too." "But enough about me sweetie, I think you are in
need of a girlie sissy reward too, look at how hard your girlish little
sissy cock has gotten, but Mother can take care of that too." "Mommy
will be glad to show you the pleasant joys of being Mommy's little
sissy."
She had him sit on the edge of the bed daintily and she handed him a
silver heart shaped lady's hand mirror. "Now look at your pretty pink
curlered head and your lovely kerchief and enjoy your glorious feminine
image while Mommy pleases you too darling." "You must always look at
yourself in the mirror darling." "Mommy wants you to see what a pretty
sissy girl look like." "Mommy wants you to accept that you are now a
sissy a boy dressed as a girl, and that this is what you needed all
along." "Mommy wants you to look in the mirror at all times and see what
a pretty girl you make and how lucky you are that Mommy has turned you
into a girl." "I know you're ashamed to be feminized like this being a
boy and you should accept your shame and humiliation but realize you are
quite happy like this."
To his surprise she pulled his bulging tented feminine panties down and
started to stroke his cock slowly with her long red nails. It was the
most wonderful feeling he'd ever felt, so soft and feminine, now he was
the one moaning in pleasure. He watched his Mother's love red feminine
nails slowly and very gently caressing his rock hard cock. "Does it feel
good sissy Priscilla?" "Oh Mommy it feels divine." "Mother loves milking
her little sissy doll." "Mommy's going to milk you very often darling to
relieve your sissy tension."
"As you become deeper and deeper involved in your feminine
transformation you'll find you're excited sexually by many feminine
things." "Mommy will help you relieve this excitement, but only if
you're a good sissy girl and do as you're told." "You much obey Mommy
and Aunt Carol and I promise you pleasures beyond your wildest
imagination." "I'm sure Aunt Carol will enjoy doing it for you too
darling." "Little sissy girls love being milked by their Mommy or Aunt."
"It helps bring out all those wonderful feminine feelings you should be
having."
"Don't look at me darling, as much as Mother appreciates you admiring
her makeup and curlers, I want you to look at the pretty girl in the
mirror now." "Soon my baby, very soon you'll look just like Mommy does."
"Won't that be wonderful darling to be as pretty as Mommy? Can you
imagine, my sweetheart being made up to look like Mummy & Aunt Carol
with really heavy older lady's make up & bouffant coiffures''.
She stroked his penis gently while she talked about seeing him in
makeup, heavy red lipstick, jewelry, big hairdos, dresses, bras and
lady's high-heels. She talked about all the exotic feminine items she
and Aunt Carol would teach him to love.
She talked of eye shadows, black eyeliner, Max Factor Cr?me Puff
powder, ultra long false eyelashes with enormous amounts of jet black
mascara, elaborate chandelier earrings with screw fixing to ''pinch''
his earlobes, necklaces and long feminine nails painted with red glossy
lacquer while she stroked his penis gently. Within a couple of minutes
he was spurting his first load of sissy cream ever into Mommy's hand
while squealing in a high-pitched girlish voice over his orgasm. He had
experienced his first male orgasm and he'd been dressed as a girl and in
women's pink curlers with his lips painted in a divine pink lipstick
when it happened. It was so intense he thought he'd pass out.
It was the most pleasurable thing he'd ever felt in his life. Several of
the older boys had bragged about their girlfriends doing that for them,
now he knew why they said it was fabulous, he just hadn't expected it
would be his Mother doing it to him. And come to think of it he hadn't
thought he'd be in curlers, panties, a bra and a nightie either when he
experienced it. But that didn't change the fact that he'd thoroughly
enjoy it so much he'd do anything to experience it again. If this were
his reward for letting his Mother and Aunt Carol dress him and make him
up he'd gladly pay the price for more of this. The pain of his curlers
was temporarily forgotten now in the glow of his first orgasm.
"Wasn't that a nice sissy milking sweetie?" "I'm sure you'll want Mommy
to do that for you often in the future and I'm sure Aunt Carol would
like to help you out in that department too." "Did you enjoy it
sweetie?" "Yes Mother, it was very, very pleasurable." "Good darling,
you'll find that's only a small sample of the sissy pleasures that can
be had if you cooperate with Mommy and Aunt Carol." "There will be many
more pleasures to delight a sissy's heart sweetie." "Aunt Carol can
dream up divine tortures and pleasures for little sissy girls like you,
she's an expert at it believe me." "Some may even seem cruel or
torturous but believe me honey they're all designed to bring you to the
height of feminine ecstasy and you'll beg for more and more of them."??
We will possibly have to begin ??milking?? you of your sissy ??spunk??
at least three or four times a day to bring the more feminine side of
you to the light??.
She pulled back the sheets of her canopy bed allowing Billy to crawl
under the covers. "Did you smooth out your nightie Darling, good girl."
"Now here is a special pillow we girls like to use when we are sleeping
in curlers." "That?s right, tuck it under your neck and cheek, here like
this." His mother then snuggled into bed and showed the defeated lad the
most comfortable way to sleep with a head full of prickly hair rollers.
"Good night sleeping beauty, give Mommy a goodnight kiss." He leaned
toward her and then kissed her on the cheek. "Oh sweetie, can?t you do
better than that?" "Give Mother a goodnight kisses Priscilla." Billy
kissed his Mother again. She held the kiss a long time, her lips pressed
against his in a passionate embrace. "Much better darling you?ll learn
how to kiss passionately like a lady soon."?? Darling, I?ll just paint
your lips again with Mommy?s lipstick so you will learn how a Mommy?s
little girl starts to live as a pampered sissy??
"Here why don?t you lay with your back to me so I can cuddle my little
princess." As they lay spooning in the dark Billy?s mother kissed his
neck. She inhaled his feminine fragrance and continued to fuss with his
roller set. Caressing his curlered head lightly. She whispered,
"Priscilla, try not to worry your pretty little head." "Mom knows what
best for you." "You just be the good girl, Mom knows you can be and I
promise you will be very happy." "Try and get some sleep because we are
going to have a very busy day tomorrow, up at seven showered and
dressed." "Aunt Carol will be here at eight to comb out our hair and
create your first older lady?s bouffant hairstyle".
"The nail salon at ten for a manicure and pedicure then the off to the
mall to get you some pretty new clothes." "I?m sure we can find you
something of mine to wear shopping, maybe my white and pink sun dress
with a pretty sweater and my pink high-heel pumps." "That's it, you will
look just darling." "I?m sure they will fit you fine." "Oh and we should
get your ears pierced to while we?re there." "The mall has a shop, we
get you some lovely long dangling earrings, very sexy and ladylike." "We
might as well get you used to wearing big dangling feminine earrings.
About 3 or 4 piercings will do for a start" "That?s enough of my
rambling Sweetheart, you get some sleep you?ve made your Mom a very
happy lady today."
Billy lay there on the verge of tears with those awful hair rollers
digging in his scalp and his lips heavily coated in Mummy?s deep red
Chanel lipstick. How on earth would he ever fall asleep, or pretend at
being a girl. Tomorrow would be terrible, a whole day of pretending to
be a girl. Dressed in the most ultra feminine clothes his Mother could
find. Would his mother and Aunt Carol really fix his hair to look like
theirs and take him shopping for dresses, oh God. What had he gotten
himself into, if he would have only studied harder. They were both going
to make him be a complete sissy faggot dressed and made up like a girl.
His other talked of only feminine things no more boy things ever!
No now that he was thinking about it, it was even worse then that, young
girls didn?t wear much makeup or have big hairdos or super big breasts
his Mother talked about. His Mother said he?d be like her and Aunt
Carol. He couldn?t believe he?d eaten his own Mother?s pussy & that he
had really enjoyed sucking her love juices, that?s what the other boys
called it, eating your girlfriend?s pussy.
Then no his utter amazement his own Mother had jerked him off while he
was in curlers, lipstick and girl?s underclothes. But she didn?t call
it that she?d said it was milking a sissy. She was even already
referring to him as a sissy and a fairy. Did she really think he was
homosexual, or is that what her and Aunt Carol had planned for him. But
he had to admit both were very pleasurable. He liked eating his Mother?s
pussy, at least until she?ll crushed his curlered head, but she?d
apologized for that and certainly the milking of his penis had been
wonderful, he loved that, a lot. But having his Mother do it was so
humiliating but also at the same time gorgeous & ??girlie?? and his
mother had said Aunt Carol would do it too & he would have to pleasure
Aunt Carol?s fanny as well & that would probably be even more
humiliating. Still it was intensely pleasurable. He was ashamed at his
Mother and Aunt Carol doing that to him, but still the pleasure had been
intense.
As Mother and son lay in bed both pretending to be asleep, their minds
were racing with the day?s activities. Bonnie, Billy?s mother was
wondering if she was doing the right thing for her son or just being
selfish. She had long been aware of his growing feminine tendencies and
his slight girlish build, of his interest in her clothing, make-up and
hair styling stuff for years. He was a total wimp with almost no
physical skills of a boy and he was very small for a boy and apparently
interested in nothing that normally concerned males.
Already she knew the other boys at school were calling a sissy and a
faggot. She figured no matter what he was going to turn out to be a
sissy anyway, about the only thing she could do was guide him into it
carefully and protect him from the bullies, rather than having him
struggle for years with his identity like most sissies. At least if she
brought him into sissyhood, it?d be far less traumatic then the years of
suffering he?d have to endure otherwise.
Many times she had noticed her lingerie drawer out of order or a dress
put back in the closet the wrong way on the hanger. Though she was
secretly excited that her son was interested in girlish things her
husband would never have let her indulge her sons seemingly girlish
desires by dressing him up like her little daughter. But now that the
marriage was over and the jerk was gone she began to contemplate the
many options she had. At least this way she?d get some pleasure out of
it too.
Without a doubt her strongest desire was to have a daughter and with
pregnancy out of the question she put together this fascinating plan.
Besides who knows where it might lead. A sissy son all dressed up like a
lady, as a lover would certainly be preferable to the other terrible
males she?s encountered. Perhaps she could have a daughter and a lover
and a lady friend all rolled into one. What an exciting thought.
She could imagine playing lovely sissy games with him and feminizing him
and making him into a submissive girlish lover for her & Carol.
Even better she knew her sister Carol was completely in agreement and
ready to help her feminize Billy. Carol had said it was all possible if
she feminized him and guided him into a forced feminized lifestyle.
Carol said she?d never actually done it herself before, but she talked
to dozens of women who had sissy lovers that they?d feminized. Brothers,
sons, husbands all feminized by their Mothers, wives or girlfriends. It
sounded like exactly what she wanted for poor Billy.
Earlier in the day when his mother announced his punishment for the
failing report card Billy?s heart skipped a beat. He was scared and
excited at the same time. He had always been fascinated with all girlish
things and on a few occasions gotten into his mother?s clothing. He?d
tried on her panties and dresses and prancing around in her high heels.
He justified it by thinking it was all just innocent fun. He liked girls
a lot and always enjoyed their company. In fact he wished he could spend
all his time with girls, he hated the boys, they always beat him up or
teased him. Girls were always polite and nice to him.
But now as he lay in bed trying to get comfortable with his hair up in
those tight curlers. With the thought of the reality of being dressed up
like a girl and paraded through a shopping mall, what would his friends
do when they found out. Billy started to quietly sob like a girl. It
would be so humiliating to see all the things they?d said actually come
true. That he was a homosexual and a sissy faggot. Dressed as a girl
this would only prove they were right. Maybe if he were with his Mother
she?d protect him from them. Bonnie listened to her sons muffled tears
and decided to explain why she was punishing him this way. She hugged
him close and kissed a curler atop his head as she whispered close in
his ear.
"Baby, sweet baby Mother knows all about it." "There is nothing to be
ashamed of, nothing at all." "I just want us both to be happy." "I think
if you accept these things we can make each other very happy, you?ll see
darling." Billy sniffling quietly asked, "What do you mean Mom." "I know
you?ve tried on my dresses and underwear and bras and played with my
make-up and there is nothing to be ashamed of." "Now that you father is
gone I want both our dreams to come true, a daughter for me and dresses
for you." "We have each other to care for ourselves now." "We don?t need
others, we can make each other happy." "Well Aunt Carol too, we can make
her happier too." "I know it?s humiliating to be dressed as a girl but
Mother understands how you?re feeling."
"But mom I don?t know if I want to be a girl." "I liked being a boy, I
was just playing around, that?s all, please don?t make me dress up like
a girl all the time." Bonnie kept kissing her son?s lips and cuddling
and caressing her sweet smelling child." She caressed his curlered and
kerchiefed head. "Oh honey that?s not true." "I know you hate being a
boy and you?d rather be a girl, it?s just humiliating to you to
surrender your manhood." "Believe me it?s better if you?re a sissy,
you?ll be much happier in the end, you?ll see." "And I know I?ll love
you much more as a sissy too darling." "Now baby lets just try it for
the summer, what harm could it do, you can see if you like being a girl
and I can see if I like having a daughter." "But what if my friends see
me mom." "I would just die if they do." "I would feel like such a sissy,
they?d think I?m homosexual."
"You are a sissy Billy deep down you know that?s true honey and I know
it so why not just admit it for once." "That?s why you feel so
humiliated, you afraid because you know deep down you really are a
sissy." "It?s OK, that you?re a sissy, Mommy loves sissies and I?ll
protect you from the other boys." "As for being homosexual there?s
nothing wrong with a little sissy love either, you might find it quite
pleasurable." "You?d be surprised how much fun you can have as a sissy
girl."
"I?ve made up my mind about you punishment so lets not pretend anymore."
"Don?t pretend that you don?t like this because Mother knows you do." "I
know it?s hard to accept, but you?ll really be much happier as a sissy."
"But Mom I don?t like it, I don?t like these curlers in my hair, they
hurt and I don?t want my friends to see me like this and think I?m gay."
"It?s not being dressed as a girl then is it, you love that." "It?s what
your friends will think that troubles you." "Baby, you must accept it,
you?re a sissy, and that it." "But you?ll find sweetie that the friends
that Mommy and Aunt Carol have won?t hate you for being a sissy, they?ll
love it and encourage you darling." "They?re not like those bad boys at
school that made fun of you." "Our friends will adore you as a sissy
girl, you?ll see."
Bonnie was getting a little irritated with Billy now. He must accept his
fate and stop this denial. It was time to show him he what forced
feminization was all about as well as forced sissyhood. "Maybe that
would be the best thing, that all your friends see the real you." "And
if you don?t do exactly as I say and follow my daily instructions in
everything to a tee I promise you young man everybody will know what a
homosexual sissy you really are." "I?ll invite them all over to see you
in complete lady?s makeup and pink curlers and a dress." Billy continued
sobbing, wishing that he had never gotten into his Mother?s things and
wondering what tomorrow would bring. "Now go to sleep my sissy girl, I?m
not kidding you had better get used to all this because your my sissy
daughter Priscilla now." Bonnie tried to quite her baby by shooshing and
cooing in his ear and whispering what a pretty girl he was going to be.
"Wake up sleeping beauty, we have a big day ahead of us." Bonnie
bellowed as she swung open the bedroom curtains. "Come on now I want to
shave your legs and pluck you eye brows before Aunt Carol gets here."
Billy had a fitful night to say the least, with his hair up in those
prickly curlers he could hardly sleep at all. As he climbed out of bed
he was too tired and demoralized to argue with his mother anymore. It
looked like he was really in for it, a whole day pretending to be a
girl.
He would just take it a minute at a time and try and make the best of
it, after all he was a little interested in girl stuff, maybe it
wouldn?t be all that terrible after all. He?d thought about it a little
last night. His Mother was right he was slowly coming to the conclusion
that he was just as his Mother said a sissy. Would it really be that bad
to be a sissy. It wouldn?t as long as his school chums weren?t around to
beat him up and his Mother had said she?d protect him from them is he
cooperated in his feminization. She?s also said that all of her and Aunt
Carol?s loved sissies. It would certainly be better to hang around with
women then men especially if they liked him dressed like a sissy.
Billy stood naked in the bathtub as his Mother sponged bathed him with
her sweet smelling bath oil. "Priscilla I want you to keep your legs
smooth and soft for the entire summer is that clear." "I?ll shave your
legs today but I want you to learn to shave your legs every week and
mine from now on too." Bonnie intended on immersing the boy completely
in ultra feminine activities. He would be no stranger to all things
feminine. She also planned on teaching Billy how to take care of a
household, to be a proper housewife or maid. She could easily see him as
a pink curlered housewife cleaning the house, or as a sissy French maid
in a complete French maid?s outfit with petticoats serving her friends
tea.
For sure he would learn how to wash and iron and clean house, that
included her clothes as well. He would be taught how to look after a
lady?s wardrobe in detail his and hers. The deferent heat setting on the
iron for the different delicate fabrics for instance. Yes Priscilla
would spend countless hours at the ironing board ironing his and his
mother?s dresses. The more Bonnie thought about it the better an idea it
seemed. A housewife to do all the chores, a pretty daughter and a gentle
loving submissive sissy son to please her orally and perhaps a lady
friend who liked all the same fashions as her and Carol. At night they?d
let him slowly get used to being a homosexual drag queen and clubbing
with others they approved of.
Maybe she?d even do like her sister Carol suggested to keep him nice and
submissive to her, she?d fuck him like a girl with a strap-on. At first
she?d been shocked when Carol had suggested it. But Carol said all the
Mother?s who feminized their sons did it and she was starting to warm to
the idea. It could be a lot of fun now that she thought about. She
giggled inwardly at the thought of her son dressed and made up like a
whore on his knees getting fucked doggie style by Mommy. It was making
her pussy wet just thinking about it. His girlish high pitched squeals
of feminine delight as she fucked him like a girl with a nice big hard
cock.
Billy looked down at his mother in her underwear and curler covered head
as she shaved his legs and realized that his hair looked just like hers.
"There now all smooth, now hold up your arms princess." "You must always
keep your underarms silky smooth just like a lady." "I can?t wait to
have you do all these things for me, it?s about time I got waited on."
"Now let?s get you dressed Aunt Carol will be here any minute."
Billy had always loved his Aunt Carol because she was so pretty, but
sometimes she was really a little crazy with her feminine stuff. She had
a wicked, evil look about her, but in a very feminine way. She was so
beautiful and super nice to him, always full of compliments and kisses.
So how could she be in on this terrible punishment, did she know all
about him trying on his Mother?s things? He was feeling really nervous
about his Aunt Carol seeing him in a dress.
"Mom I?m scared, I don?t want Aunt Carol seeing me dressed like this."
"You silly girl, believe me Carol is looking forward to this day as much
as I am." "It was her idea to have you work with her at the salon."
"She?s dying to teach you all about hairdressing and lady?s makeup."
"She thinks you will fit in marvelously down at the beauty parlor."
"You?ll become just one of the girls eventually." "You?ll see it won?t
be bad like at school where everyone teases you or beats you up." "At
Carol?s salon you may be teased a little but you?ll be appreciated as a
sissy girl."
Billy always enjoyed going to the beauty parlor with his Mother. He
loved the smell of the shampoo and hair spray and all the feminine
products and cosmetics. He liked it when his mother?s friends would say
he was too pretty to be a boy and that his thick blond hair was to die
for. Normally he would sit and watch his mother and the other women get
their hair set in rollers or perm rods, often sitting next to his mom
(if a hair dryer was vacant) while she cooked under the dryer.
He loved the feel of the warm air on his head as he watched the ladies
in the shop have their hair styled. It was the early sixties so everyone
wore meticulously styled bouffant hairdos. He often could not believe
how his mother would come to the beauty parlor with flat hair and leave
with a huge rounded stiff ball of hair with curls all over, it was like
magic.
"Now step into these sexy panties sweetheart", Bonnie said as she held
open a pair of her cutest lacy pink panties. She then adjusted her
feminine undergarment so that they fit just so, at least for now. Later
on she?d introduce him to being displayed as a sissy girl. She couldn?t
wait to see his little sissy cock sticking straight out in excitement
over his feminization. "Maybe today at the mall we can get you fitted
for a nice slimming girdle, or a corset honey." "You won?t believe what
they will do for your cute little figure." "Now lets get you into a nice
bra." "I bought this last week guessing at your size." "I just couldn't
resist, my girl?s first bra." "Now hold out your arms darling." Bonnie
fitted the delicate lacy bra around her son?s chest and adjusted the
shoulder straps just so. "My oh my don?t we look modest, don?t be shy
darling it?s just us girls." "Soon you?ll love wearing big lacy sexy
bras honey." "You even want bigger and bigger tits in your nice lacy
bra." "Now lets find you a slip."
Billy stood awkwardly in his Mothers bedroom while she quickly sifted
through her drawers looking for a pretty slip. She turned with a filmy
ladies full slip and held it up again his frail thin frame. "Oh I think
this will do nicely." "Hold up your arms Priscilla, good girl." As the
fragrant ladies nylon slip drifted down over his curlers and passed his
face Billy got a warm tingly feeling in his stomach. His mother adjusted
the shoulder straps and fussed with the hem. "Oh Baby you look
absolutely precious in Mommy?s slip." "Here give me a kiss and thank
Mommy for dressing you up like a lady." Too his amazement as he kissed
his Mother he felt her hand stroking and caressing his penis through the
silky soft nylon of the slip. He was rock hard and the slip was actually
bulging out and his Mother was milking him again. God he thought it felt
eve better being stroked through the silky fabric.
Billy could hardly speak, part of him started to enjoy this new
closeness with his mother but the other part was so humiliating to be
dressed in her clothes right in front of her like a sissy faggot. But
God it felt so good when she caressed his penis through the silky nylon
slip. Her touch was almost electric. It felt so sensual and wonderful.
"Thank you Mommy for dressing me up", Billy choked out. "Your welcome
Princess." "Now kiss Mommy in return...good girl." "What a lovely kiss
darling." "Doesn?t it feel nice little sissy girl?"
"Now before we pick out a pretty dress for you to wear today, I want you
to pick out a pretty dress for me to wear." "Selecting the proper outfit
for a lady is an art, one that you will have to learn in detail." Billy
nervously touched his Mother?s dresses wondering what dress she would
want to wear. "Come now Priscilla, make a couple selections, we can both
try on as many dresses as it takes." Billy still frozen with
embarrassment hardly knew what to do. "Come on Priscilla we don?t have
all day." "Here I'll help you this time but tomorrow I want you to lay
out all of my clothes for me, panties, hose, slip, shoes and dress, is
that clear young lady." Billy stepped back as his mother selected a
dress from her closet.
"Here this one is just darling, hold it out for me to step into it, good
girl now zip me up." "All the way, now the little clasp, good girl
Priscilla." "You?re going to make a fine lady?s Maid eventually." "Now
where is that pink and white sun dress." "Ah here it is, it?s a little
small for me so I think it should fit you perfectly." "Hold up your arms
darling, that?s good be careful not to muss your curlers Priscilla." The
pretty pink and white sun dress was covered in pastel flowers and fit
him like a dream, with it?s wide shoulder straps it had an off the
shoulder flair, the tight bodice clung tightly to Billy?s waist then
flared out to just below his knees. His mother finished zipping him up
sealing him into her pretty flowered dress. He was now imprisoned in his
Mother?s very feminine dress.
"Oh my Priscilla, that dress looks absolutely darling on you, do you
realize what a pretty girl you make." ??Just one more small item my
Darling so please bend over & steady your self against the dressing
table while Mummy fetches the finishing touch?? His Mother left the room
& soon returned with some items in a small satin bag. ?? Now Darling
this may feel a bit uncomfortable but this is essential?? Billy felt his
Mummy?s fingers around his ??sissy hole?? ??First some lubricant my
Darling & then I?ll plug you with this precious medium size butt plug??
Billy started to protest but Mummy slapped his bum & told him ??This is
how sissies get used to real sex with other sissies & even real men so
we need to open up your ?sissy hole ??a tad" Mother applied some more
lube & Billy gasped as his Mummy very gently pushed the plug fully home
into his virgin hole.?? There Billy?? said Mother ?? That wasn?t so
bad?? & Billy had to nod & agree that after the initial tightness the
feeling of the butt plug was very erotic
When Aunt Carol gets done with your hair and make-up no one will ever
know that you?re not 100% girl." "Now spin around for me Princess, I
want to see your pretty dress float around your legs just like a girl."
Billy began to spin as the dress flared out in a graceful billowing
motion. He started to feel that tingly feeling again as his mother
smothered him with hugs and kisses. He had that raging hard-on again and
it was even beginning to tent out that pretty sundress. Just then the
doorbell rang followed by a, "Yoo hoo, is anyone home." It was Aunt
Carol and Billy realized he really was about to have his hair done, done
just like the ladies at the beauty parlor, done just like his mom?s.
As Aunt Carol entered the bedroom she slowly lowered her bags full of
hair supplies with a look of shear astonishment on her face. There
before her was her cute little nephew with his hair up in pink curlers
wearing one of his Mother?s pretty dresses. It was true, her sister
really did intend on turning the poor boy into a darling daughter and
who knows what else. Bonnie continued spinning poor Billy around so
Carol could get a good look at him in the dress. "Well, what do you
think?" "Isn't he adorable", Bonnie beamed. Carol still astonished knelt
down and held Billy?s face in her hands. Did you really sleep with that
head full of pink curlers all night?" Billy nodded yes. "You poor baby,
sleeping in curlers isn't as fun as it sounds is it?" "But it is very
girlish and feminine." "You should always take pride in sleeping in your
curlers like a girl." "I guess your one of us now Billy."
As Carol stood almost disregarding Billy and speaking directly to her
sister she sighed. "What a morning, can you believe I was at the shop at
6:30 this morning for my comb out, Darlene took me first thing so I
could be here to help you with our little precious." As Carol patted her
huge rounded bouffant flip she asked," What do you think, that Darlene
is getting really good at combing me out, do you like the new color?"
She turned so her sister could see the back of her bouffant as she
patted and primped her stiff lacquered bubble flip. "I think it looks
marvelous, the red highlights are really subtle." "I wish I had your
rich brown hair instead of my mousy blonde." "Why don?t you and Princess
here come in tomorrow for some color and a frosting." "I think you and
Billy would look adorable a little lighter with some highlights." Carol
said as she knelt back down to talk to Billy, removing his headscarf and
net she removed one of his hair rollers.
"So what do we have here, a bad boy being punished?" "A bad report card
has its consequences", she said as she winked at Bonnie. "Wow wee
Princess your hair takes a beautiful curl are you going to be a good
girl and let Auntie Carol give you a pretty new hairdo", Billy nodded
yes in silence. "Well then lets get started, I?ll meet you two ladies in
kitchen ASAP."
Bonnie guided Billy to the bed and began to roll a pair of pink lacy
ankle sock on his feet. "These will look darling with your dress Billy,
plus I think they will go nicely with the pink high-heel pumps." As she
slid her pumps onto her son?s feet Billy got that buzz in his tummy
again. He liked the way his feet looked, all girly with those little
girl socks and his Mommy?s high-heels. If only he could just stay at
home and pretend to be a girl with his Mother and Aunt. Then nobody
would make fun of him and he could just enjoy being a girl. Billy then
got a familiar blast of his mother?s perfume and then several more.
As mother and daughter walked down the hall to the kitchen Bonnie beamed
with pride at the pretty little girl walking in front of her, her dress
swaying and her heels clicking on the hard wood floor, what a fun day
this was going to be. Carol asked in a bossy tone, "Now which one of you
ladies is going to get her hair done first?" Bonnie sat down in the
chair and stated, "I want Priscilla to help you with my hairdo, she has
to learn soon enough how much work goes into looking beautiful." "Okay
then, so its Priscilla is it, I think that name suits her just fine",
Carol stated as she draped her sister in a pretty pink hairdressing
cape. "Okay Priscilla make yourself useful and take the rollers out of
your Mother?s hair", Carol ordered as she sat down to watch.
Billy awkwardly stood behind his mother and began to untie her curler
scarf and net; gingerly setting them on the table he already had the
mannerisms of a girl. One by one he removed the rollers from his mothers
hair, first sliding out the pick then slowly unwinding the curler until
her hair sprang back in a tight curl. The two sisters jabbered away
occasionally complimenting him on the job he was doing. "Good job
Priscilla, I think you really have a knack for hairdressing young lady",
Carol said winking again at Bonnie. "Now go into the bedroom and get my
curler basket and neatly put those rollers away".
As Billy left to retrieve the curler basket Carol leaned in close to
Bonnie and asked, "So how is it going, has he given you any trouble so
far?" "Not really, I think deep down he really enjoys his new
punishment." "I told him that I knew about him sneaking into my things,
except for a few tears last night he has been very cooperative."
"Doesn?t he look just darling sis?" "I can?t wait to get my hands on
that hair of his", Carol said as she started brushing through her
sister?s curls. "Not to mention getting him all made up." "Of course a
little jewelry couldn?t hurt either", both women laughed.
Billy was back and neatly arranging his Mother?s curlers in the basket.
"Priscilla put the picks in that little yellow bag then leave it on top
of the curlers." "I just love calling him Priscilla, it?s going to be so
much fun having a sweet little sissy girl in the house." Carol was
finished with the brushing and ready to start back combing her sisters
hair. "Priscilla I want you to pay close attention to what I?m doing,
now come over here so you can see better."
Billy stood next to his Mom as Carol selected a small swatch of curled
hair at the crown of his Mother?s head. She then began to comb the hair
backwards with short quick deliberate strokes causing the swatch of hair
to look tangled and stand up stiffly on it?s own.
"This is called "back combing" young lady, or as you mother says,
"teasing". It?s very important to learn to do this correctly to get the
height and volume required for today?s bouffant hairstyles." Carol
continued back combing her sister?s hair stopping every now and then to
spray the teased hair with a good solid blast of fragrant Aqua Net hair
spray.
"Here Priscilla, you give it a try", Carol handed Billy her rat-tail
teasing comb and pointed to a curled section of his Mother?s hair.
"That?s it hold it up taught, now back comb it like a good little sissy
hairdresser."
Billy tried somewhat awkwardly but seemed to understand what his Aunt
Carol was talking about, pretty soon he was tangling his Mother?s hair
just like a real hairdresser, and enjoying the praise from his mother
and Aunt Carol. "Good Girl, you will be combing out the ladies down at
the shop in no time, now give it a good spray, here you go Sweetie". As
Carol handed Billy the can of hard to hold hair spray he began to spray
his mothers freshly teased out hair.
Carol ordered Billy to sit and watch as she finished up his Mother?s
bouffant, as she teased, sprayed and picked at the delightful curls in
his Mother?s evolving hairdo Billy began to realize that he was next.
Here he was sitting in his kitchen wearing his Mother?s dress and pink
high-heels with his hair set in women's hair curlers waiting to have his
Aunt Carol tease and style his hair just like a ladies hair. Just like
his Mothers hair, in a big puffy bouffant with curls all over. That
tingly feeling started to turn to sickness as his Mother?s hairdo was
taking shape. He used to like to watch his mother get her hair done but
now it wasn?t as fun.
Carol was now pulling wispy petal curls up and out of the teased base
with a small hair pick, she was getting incredible height and Billy
could hardly believe how big her hair was. Bonnie?s hair was starting to
look the way it always did with soft curls folded over soft curls,
delicate feminine curls teased and rounded and sprayed into place with
endless amounts of hair spray. The sides and back puffy and gently
tucked under with sweet kiss curls invading her cheek. Her bangs were
curled under with every hair in place and sprayed evenly with the sweet
hair spray. Carol Stood back and handed the can of Aqua Net to Billy.
"Here you go Princess, give your mom a good spray." Billy took the can
of hair spray a began to spray his Mother?s beautiful bouffant hairdo
all over, he could hardly believe this was happening, dressed up like a
girl spraying his Mother?s hairdo.
Billy?s mother stood up patting and primping her sculpted bouffant
hairdo. "Oh Carol your a genius with hair." "Do you really think you can
teach are little lady here to do hair like this." "You know I will, but
it won?t be easy." "It will take Billy, I mean Priscilla here thousands
of hours before she gets her cosmetology license." "It will be a lot
easier for her adding up her hours down at the shop with me and girls,
we will keep a close eye on our little Princess." "Now Priscilla lets
get you combed out, sit down precious."
Carol then wrapped the helpless boy in her ladies hairdressing cape
tying it off tightly at his neck. "I?m sure hope you didn't mind
sleeping in curlers last night Priscilla." "That?s something that will
save you a lot off time in the future, off course when your working at
the shop you can let your set air dry or take some moments under the
dryer when we?re not so busy." Carol was almost finished removing the
rollers from Billy?s hair as his mother sat watching in blissful
adoration at the beautiful little girl she had created.
She could hardly wait to see him trying on dresses in the ladies
boutique?s at the mall. What fun she would have curling his lashes and
brushing lots of black mascara on his long pretty lashes. Maybe even
false eyelashes would look more dramatic. Painting his pretty girlish
lips with delicious colorful flavors of lipstick. Or better yet having
him learn to do her make-up & perhaps even as a personal hair stylist.
She could live like a queen as long as she kept him under her firm
feminine guidance.
Carol was now brushing through Billy?s pretty curls." "So what do you
think hon?" "Should I give her a fancy French twist with lots of back
combing, maybe a beehive, or will it be a darling bubble flip, we would
look like twins", Carol said as she pressed her cheek to his careful not
to muss her fresh stiff bouffant flip. Bonnie explained that she had set
Billy?s hair just like hers so that he would have to wait a couple of
days to get Carol?s stylish bubble flip. His fate was now sealed, he was
going to get his hair done just like his Mother, they now had the same
cut and set. Billy did not like the way the back combing felt, Carol was
so rough, pulling his hair up and then sharply teasing, it really hurt.
"I?m not hurting you am I Princess, are those tears I see?" "Now don?t
be a baby sissy Priscilla, girls have to endure some minor discomfort to
look beautiful." Carol continued teasing the poor boys hair roughly, " I
think your hairdo is going to be bigger then your Mom?s." She proclaimed
as began to give Billy the first blast of smothering hair spray.
Bonnie could not believe the height Carol was getting with Billy?s hair,
she could not help but picture this pretty girl of hers standing in the
beauty parlor wearing a darling hairdressing smock combing out one of
her lady friends hair.
He?d be a total sissy faggot and under her control. Oh how proud she
will be and how jealous her girlfriends would be for her to have such a
dutiful darling daughter. Billy sat in silence as the painful
backcombing was coming to an end and Aunt Carol began to busy herself
with the finer more delicate work in creating his new ladies hairdo. "Oh
Carol, she looks absolutely darling."
"His hair is just wonderful to work with, we will have no trouble at all
with the bubble flip or the French twist, the girls at the shop will be
so jealous, why do boys always get the best hair and eye lashes." The
ladies giggled and continued oohing and ahhhing at just how pretty his
new "do" was turning out. More spray sspppppssstttttsssshhhhh Billy was
starting to cough as Carol relentlessly picked patted and adjusted
delicate curls with her fingers and hair pick. "Now that is an adorable
hairdo if I do say so myself, hold still Princess while a set this style
for good." Carol began spray Billy?s bouffant one last time all over
back, sides and top. "It will take a hurricane to muss this hairdo
little lady" and that?s just what he looked like, a little lady.
A young girl much too young for a grown up lady?s hairdo like this, he
reached up to touch the feminine confection almost in disbelief. His
hair was stiff and round and only moved back only a little when he
pushed on it, it looked exactly like his mother?s hairdo. His mother
then showed him how a lady pats and gently checks her hairdo with light
limp wristed touches and primps. He looked so cute checking his hairdo
like a lady the two women smothered him with kisses and hugs telling him
how darling his hair looked and what fun they were going to have showing
him off at the mall. "Now lets get your cute little cherub face all made
up pretty like the darling young lady you are."
Carol covered his face with several layers of Max Factor Pan Stick
foundation in a darkish beige shade & blended it well into his neck &
even down to the top of his brassiere. Cr?me Puff powder in Twilight
Blush was next, the powder was applied with a very large soft brush &
also the powder puff to press the powder into position for the wonderful
matt finish so adored by older women. Next she penciled in his plucked
eyebrows with soft black eyebrow pencil into a glorious arched thin brow
with teardrop shaped inner corners. Carol stood back to check the
foundation & eyebrows and cooed then she really went to work, applying
several shades of eyeshadow to his lids. She pasted false eyelashes on
his closed lids. They weren?t outrageously big yet, just very thick and
sexy, he looked so adorable, she couldn?t wait to see him in some really
big false eyelashes like a Vegas showgirl. She next did black eyeliner
all around his eyes and then applied some rouge to his cheeks. Finally
the lipstick was brought out and applying. Wearing lipstick still felt
so strange, but such a wonderful smell and sensation.
"Well I think our little feminine dolly is ready for her trip to the
mall." "Look at yourself in the mirror Priscilla, this is the new you."
As he gazed into the mirror he couldn?t believe what he saw. He no
longer looked like a little girl with an older woman?s hairdo. Now he
looked completely like his Mother, a full mother. Completely made up and
with that big hairdo he looked like he was in his early 40?s perhaps. He
smiled at the pretty, sexy woman in the mirror and she smiled back, her
lipsticked lips slightly parted. "Thank you Aunt Carol for doing my
makeup and hair." "You?re welcome darling, but you can thank Auntie
properly when we get back home from the Mall." Both sisters winked at
one another and laughed.
Over the next few weeks the hair & makeup on Billy was refined & altered
to suit his mood & occasion
Six months later Priscilla was working at the salon full time. The way
she saw it her life was divided into four segments. Each morning she
arrived at the salon early and set her now long and strong blonde hair
in pink rollers and put a black hairnet over the curlers. She applied
her extensive makeup. 2 coats of very heavy L?Oreal Visible Lift
foundation in a darkish beige tone, Max Factor Cr?me Puff powder to
achieve a classic matte effect, black eyebrow pencil forming her rounded
sissy eyebrows, eyeshadow in several shades of purple, blue with
iridescent white just under the brow, Long black false eyelashes were
applied to both her top & bottom eyelids, black eyeliner was applied
very heavily around her top & bottom eyelids and then flipped out
towards her eyebrows, tawny blusher and finally pink blusher was heavily
brushed onto her prominent cheekbones To finish her maquillage lipstick
was applied of course with the lipstick first brushed on and then filled
in straight from the tube in a satin darkish red. Then she dressed in
her pink salon dress & put on her pink high stiletto heels and awaited
the first customer.
She worked that way in the salon from 9:00am to 12:00 noon every day
setting other ladies hair and wash hair etc. She had lunch with the
girls still in curlers and then at 1:00pm Aunt Carol removed her curlers
and had her hair styled into a huge towering bouffant lacquered hairdo.
Then from 1:30pm till 5:00pm she was worked in the salon again but this
time with a huge towering bouffant teased up hairdo and even more
makeup, which was phase two. She had 2" inch long red nails and wore 6"
spike high heels in the afternoon. She pranced and minced about the
salon styling women?s hairdo and talking and chatting like a complete
sissy faggot.
Aunt Carol and his Mother were quite proud that they had trained him to
act like a complete homosexual transvestite beautician. His long nails,
big teased up hairdo and extensive makeup made him look like a 40 year
old drag queen stylist. Which please his Mother and Aunt Carol greatly.
But this phase two was still just work and acting like a faggot at home
it was much worse.
By now his Mother and Aunt Carol had also trained him for complete sissy
sexual servitude at home. After supper they spend hours dressing him in
every conceivable female costume and acting out the appropriate role to
go with it. He was dressed as a sissy French maid, a little girl, a
hooker, a drag queen impersonator, a latex fetish bitch and any other
role the wished to try out. Of course each individual role required him
to learn the appropriate feminine behavior and mannerisms to go with it.
In phase three at home he played every sexy female role available and
then was ordered to orally service both his Mother and Aunt Carol. His
life was a never-ending array of makeup, big teased up hairdos, jewelry
and exotic female clothes, long nails and high heels. He was spanked,
put in bondage like a femme fatale in distress and paraded around like a
complete cross-dressed sissy faggot. In the beginning he liked the
clothes and makeup and being a girl. But as the costumes got more exotic
and the makeup heavier and the punishment more intense he began to hate
it. But as time wore on he became addicted to even the intense sexual
games too. Probably because of phase four... his pleasure.
At the end of every night after the women had been pleased they also
provided him with complete sexual service. Sometimes they took turns
milking him to an explosive sissy orgasm. Sometimes Aunt Carol or his
Mother sucked his sissy cock; other times they fucked him with a strap-
on dildo. On rare occasions he even was allowed to fuck Aunt Carol or
his Mother, but other rarely and always with him of the bottom and them
on top. The sex of course was fabulous and very intense and soon he was
addicted to all their kinky games, sex, makeup and clothes too.
Then in the morning the cycle started all over again with him at the
salon. Weekends were devoted to housework and later in the day searching
out new friends on the Internet who liked their ultra feminine images.
Soon they had him milking other sissies and finally sucking cock like a
true homosexual faggot. Even if he could undo it now he wouldn?t. He
enjoyed the glamorous female clothes, dazzling female jewelry; the big
teased up hairdos and all the woman?s makeup even the sex. He was now
completely transformed by his Mother and Aunt Carol.
The End