Archive-name: Changes/scholboy.txt
Archive-author: Daisy Ambersen
Archive-title: Weekend Away From School, A
Christopher Reilly woke up early that morning and quickly showered
and dressed in his school uniform. He was a freshman at St. Mark's
Academy for Boys, and although his studies were progressing nicely, he was
still homesick. It was November and he had been away from home for over
two months. He had always been an excellent student in grammer school and
from his earliest years had been something of a teacher's pet to the nuns
at St. Stephan's. Boarding school was a new experience, however; he
missed his mom and sisters and, although he never would have dreamed it
before, even the nuns. St. Mark's was a small school run by an order of
cloistered priests. There were no females at the academy at all; the
teachers as well as the support staff were all members of the religious
order.
This morning promised to be interesting at least. A small group of
ladies from the local parish had been invited to share breakfast with some
of the students and their teachers. This was to be something of a "get-
acquainted" session in that rarely had the academy grounds been open to
outsiders, especially women. As a reward for doing especially well in his
classes, Christopher had been selected as one of the half dozen students
invited to take part. The breakfast was held off the main dining hall in
a seperate room. The boys helped serve the breakfast, bringing each of
the ladies food before taking their seats which alternated around the
table, one of the ladies, one of the students, and one of the priests.
Chris served Father Tom and then brought a plate of bacon, eggs, and
pancakes to the woman he would be seated next to. He guessed she was
nearly forty and although on the heavy side, had a very kind and even
pretty face. She thanked him as he took his seat and introduced herself
as Mary. Her perfume filled Chris's senses and after being seperated for
months now from any female company at all, Chris delighted in the
conversation and seldom let his sight off her. He spoke of his studies
and his participation in intramural sporting events, and she in turn spoke
of her life in the small community just down the road from the academy
gates. Mary explained that she was a widow with one daughter away at
college on the West Coast. Chris listened attentively and impressed Mary
as a perfect little gentleman.
The breakfast over, the boys cleared the dishes and the Fathers
expressed their gratitude to the ladies for attending. A suggestion was
made to continue this interaction, perhaps by permitting the students to
visit off campus periodically. Chris returned from the kitchen and moved
to take his seat, but Mary motioned him to her lap where, although a
little embarassed, he felt very comfortable. With her arm around the
young freshman, she cradled him affectionately against her massive bosom
and ran her fingers thru his curly hair. She told Father Tom how Chris
was such a cute little child welcome to visit her home at any time and as
the priest agreed to allow the boys off grounds and thanked her for the
kind offer, Chris was lost in a flood of senses. He let his head rest
against her wondrous breast and let the smell of her heavenly fragrance
fill him.
The Thanksgiving holidays were now upon them and this presented
something of a problem. While most all the other students were from the
region, Chris' family lived almost 1000 miles distant. Although this was
unusual, Chris' father was an alumni and hence the selection of St. Mark's
for the boy's education. While his family wasn't poor, flying home for
Thanksgiving and then again in a few weeks for Christmas, was more than
they could afford. It was presumed Chris could remain on campus, and
while that was possible, it would cause the staff inconvenience in that
repairs to the dormitory had been planned while the students were away. A
solution was quickly found. The subject came up on Sunday as Mary was
chatting with Father Tom after Mass at the local parish where he
assisted. Mary offered to open her home to the boy for the long weekend
and the priest agreed subsequent to approval from Chris and his parents.
Of course, after a week of dreams filled with visions of the older woman's
breasts and the heady aroma of her perfume still in his mind, Chris'
answer was quaranteed. His mom & dad also thought it an excellent idea
after a recommendation from Father Tom.
Wednesday, after the other boys had already been picked up by their
parents or taken to the bus depot, Chris anxiously awaited his ride. His
small suitcase was packed and ready to go. Just as he realized he was the
last still waiting, Mary pulled up in the driveway. He sat his suitcase
behind the car near the truck as Mary came around the car and motioned him
to her. She lovingly wrapped him in her arms and gave him a kiss on the
forehead, explaining how pleased she was to have him for the holiday. As
she enveloped him in a warm hugg and drew his head against her bosom,
Chris once again seemed lost in her warmth. She opened the passenger door
and the boy, almost in a trance, took his seat beside her and off they
drove. (Did you notice that? Where's the suitcase?)
As they pulled in the circular drive to Mary's house, Chris looked
out in awe. Obviously Mary was wealthy, the house appeared almost a
mansion and the grounds leading up to it were nearly as large as the
entire campus. To his surprise, they were greeted as they pulled up by a
tall young woman dressed in a maid's uniform. Mary introduced the woman
as Carolyn, her personal assistant and maid. The boy, his eyes glued to
the woman in her short black satin dress and dark stockings and heels,
blushed as Carolyn curtseyed and taking the lad by the hand, led him into
the house. Dinner was about to be served, and after being shown the
powder room where he could wash up, Carolyn ushered the boy into the
formal dining room and seated him next to Mary at the large table. The
table seemed almost too empty, but then Chris remembered that Mary had
been recently widowed and Mary explained that like him, her daughter Susan
had decided to stay on the West Coast with friends for the holiday.
Everything about the house was beautiful; it was huge and decorated with
ornate lace curtains and fresh flowers on every table. Never had he been
in such a wondrous place. As the two of them chatted, Carolyn served the
meal. At such an impressionable age, his body and thoughts affected by
the rush of hormonal change, Chris couldn't help but steal glances at the
maid as she scurried about, her brief uniform showing off frothy white
petticoats as she bent to place the various dishes on the table. Mary
smiled knowingly at Carolyn as she took note of the boy's distraction.
"You've had a long day, hon. Why don't you draw a bath for our little
guest, Carolyn, and he can get what I'm sure is some needed sleep. You'll
be sleeping in Susan's room, Chrissy" Mary went on to explain.
The boy noticed the affectionate manner she had addressed him, and while
blushing slightly, liked the sound of it. "Thank you, Ma'm. You've been
so kind to me."
With that, Mary excused herself and Carolyn led the youngster up a long
curving stairway to make an early night of it. Following the young woman
a step of two behind, Chris couldn't help but notice how her long shapely
legs disappearred beneath the froth of petticoats. From this new vantage
point, Carolyn's also displayed the frilled garter tabs that held her
stockings taut. Glancing over her shoulder, she smiled as she noticed the
boy's stare and gave her hips a more pronounced wiggle to tease him
further. She lead the boy into his room for the weekend, and while he was
too polite to say anything, he couldn't help but feel strange. Susan's
room was far different than any he had been in before. It was definitely
a girl's room; the walls papered in a delicate pink floral pattern and the
bed which dominated the whole room looking as if it belonged to a
princess. It was covered in a canopy hung with wispy lace as were the
curtains and the vanity.
"I'm sure you'll be comfortable here" Carolyn said with a gleam in her eye
as she entered the bath just off the room and began filling the tub.
Chris stole a peek into the bath and saw that it too was definately that
of a young lady; everything in pink, from the towels down to the thick
carpeting. Chris waited sheepishly, anxious for the woman to leave him in
privacy. Carolyn re-entered the room and noticing the boy being ill-at-
ease brought him relief "I'll leave you to your bath, sweetie; you'll find
everything you need in the bath. I'll be back later with your things."
With that she left the room and Chris quickly removed his clothes, and
leaving them folded on the bed, hurried into the bath. For as long as he
could remember, he had only taken showers, and this bath was not just a
bath. The large tub was near overflowing with a froth a fragrant
bubbles. Being alone, there was no need to feel embarassed, so he slowly
slid into the warm luxuriant suds. Just as the boy settled into total
relaxation, he was startled by the door opening and Mary entering, Carolyn
at her heels.
"I'm afraid we have a slight problem, dear" spoke Mary. "Somehow your
suitcase didn't make it into the car when we left the academy. I've
called the school, but there's no answer."
"Oh, that's right, I don't remember putting it the trunk; it must be still
there in the driveway." said Chris as he tried to slide deeper beneath the
bubbles. "I guess I will just have to wear what I came in; it's no
problem."
"I'm afraid I already sent your clothes to the laundry, hon" Carolyn
volunteered.
"I'm sure we can find something for you to wear, dear. Here, Carolyn will
shampoo your hair and I'll look for something. You needn't worry your
little head."
The boy, although embarassed by the presence of the two ladies in the
bath, being in such unfamiliar surroundings, didn't dare refuse the
kindness of his host. Covering himself beneath the suds, he sat quietly
while Carolyn soaped his back and scrubbed him with a soft brush. He
hadn't been "given" a bath since early childhood. Despite his confused
state, Carolyn's efforts were pleasurable. As she knelt at the side of
the tub and began lathering his scalp, Chris' eyes were drawn again and
again to the bodice of her uniform. Carolyn was obviously well endowed in
that department, and peeking thru the sudsy lather, Chris watched intently
as her cleavage shook so closely to his face. Taking the handsprayer, she
rinsed the soap from his hair, running her beautifully manicured fingers
thru his curls. Retrieving a fluffly pink towel from the cabinet, she
held it out and motioned Chris out of the tub.
"Don't be embarassed, dear" she said with a grin. "I do have brothers, you
know."
The boy quickly grabbed the towel and wrapped it tightly around himself as
he stepped from the tub. Carolyn had already taken another and began to
vigorously dry his hair. She then wrapped the towel about his head and
giving it a twist, left it bound as he had seen his mother do so many
times before with her hair after shampooing. She surprised him further,
however, when while he looked away, she had begun to douse his hairless
upper body with body powder. His face turned bright red as this was
certainly not for men. She had used a feathery puff and the powder had a
decidedly feminine fragrance.
She giggled. "There you'll smell so sweet for bed now" she said as she
turned and left the room. "Let's see if the mistress has found you
something nice to wear." At last he was alone again.
Just as he finished drying himself, he heard the two women return to the
room. "It seems you'll have to borrow something from Susan's wardrobe,
Chrissy" Mary said from the bedroom. "I know these are hardly suitable
for a nice young boy, but they'll have to do under the circumstances."
Carolyn entered the bath, and what she carried in her hands caused the
boy's jaw to drop. Carolyn offered the frilly pink nitie and matching
panties to the stunned adolescent. The little babydoll had a lacy bodice
and silken spagetti straps. The panties were equally brief and like the
top, were trimmed in lace.
"Oh God! I can't wear that!" said Chris loudly.
Hearing that, Mary joined them in the bath and put her arm around the
boy. "Oh, don't be silly! It's only till tomorrow and we'll get your
things from the school."
"But I'll look so funny in a girl's nightgown" whimpered Chris.
"Now now, you put them on and I'll find you a robe to wear. That'll be
better then, won't it?" asked his host.
"Well, I guess so" replied Chris, his face still beet red.
Mary and Carolyn left the room and closed the door behind them. Chris
lifted the dainty little panties and resigned himself to a night in girl's
frillies. He stepped into them carefully and pulled them up his legs. To
his surprise, they felt wonderful, so soft and silky. Then raising his
arms, he slipped the short nitie over his head and let it float down over
his slim body. It too felt delicious, but that that was something that
would forever remain his secret. He turned to look in the full length
mirror on the back of the door. The sight that met him gave him a
shudder. Standing there on the fluffy carpet, he could have been mistaken
for a girl, his hair bundled up beneath a thick pink towel and and his
body sheathed in such a sexy little babydoll of the same hue. His body
gave away what his mind was thinking. As he gazed at the reflection in
the mirror, his penis began to grow and thicken. How could he think this
wayhe thought. I'm a boy!
Just then the door opened and Carolyn inched thru. Chris just about
jumped out of his skin with embarassment. He turned away to hide the
source of his shame as Carolyn let out a giggle."
"You look darling" she said, grinning inside as she caught a peek of the
boy in the vanity mirror, his attempt to hide his erection failing.
"Here, let's put this on" she said as she held a diaphanous pink robe out
for the boy to slip into. This was almost as bad, but it was, at least,
somewhat longer and offered a degree of modesty. It too, was trimmed in
lace at the shoulders, hem, and sleeves. With that, she took the boy's
hand and led him back into the bedroom. Mary was there waiting, a glass
of warm milk in her hand.
"You look so precious" she said as she handed the glass to the boy and
kissing him on the cheek. "Drink this now; you'll sleep better, dear.
Carolyn will stay and dry your hair for you and tuck you in; I'll be up
later to kiss you goodnite," Turning away, she winked at the pretty maid
and left the room, closing the door behind her.
"Sit up on the bed here, chrissy" said Carolyn. "Finish your nice warm
milk and I'll take care of your hair."
Despite his embarassment, the boy felt a delicious warmth sweep over him.
He had never been pampered as he had since his arrival. He sat on the
bed, his frilly robe spread out around him, as Carolyn removed the damp
towel and began to brush his curly blond hair. Whether it was the result
of such a long and exciting day, or warmth of his milk, his whole body
seemed to relax. As the beautiful servantgirl drew her soft hands over
his scalp again and again, he seemed to float away into another world.
"Isn't this nice?" asked Carolyn as the boy could only nod. "You're as
pretty as a little girl in your nitie. You smell so sweet and lovely,
dear."
Chris felt lovely, too. He had never felt anything like this. He
couldn't explain it. One part of him wanted to scream and run, but
another part of him, held captive by the light caress of the silky
lingerie, the gentle attentions of the maid, and the warmth of his bedtime
drink refused to leave.
"So soft, so pretty" he could hear Carolyn whisper in his ear. He could
feel her fingers gently trace along neck and down the bodice of the
nightgown. "My beautiful little Christine" she whispered as he laid back
against her bosom, his mind lost in a trance. He felt her red-tipped
finger draw across his lips and his body seemed to shiver to her touch.
He hardly took note as she lay him back on the silken sheets, running one
hand thru his hair and the other down and under his frilly babydoll. She
pulled the lacy little panties down a bit and freed his penis, now hard
and throbbing. He shuddered in delight as she took a frilly hankie from
her bodice and wrapping it his shaft, began milking him. His senses were
overloaded; the touch of the silky nightgown on his body, the fragrance of
the room, the sight of Carolyn bending as she ministered to him, and the
featherlike stroking of his genitals controlled his mind. Finally, as she
caressed his lips with her own and he tasted the creamy red gloss that
covered them, his whole body shuddered in spasm. His boyish juice
exploded into the silken hankerchief. Carolyn smiled down at their guest
and gently cleaned him. He had never in his life felt so wondrous.
Lifting his back from the cool sheets, she removed his robe, and now,
dressed only in his babydoll with their matching panties, she pulled the
coverlet over him.
Kissing him on the forehead, she whispered "goodnite chrissy, sleep
tight." She turned off the light and closed the door behind her, leaving
the boy asleep and dreaming.
The boy's sleep was filled with dreams that would have
disturbed him had they remained in his memory more than a fleeting
moment. In his dream, Christopher had found himself back at St.
Mark's Academy for Boys in the room he shared with two other
students. What surprised him however, was that while the other two
wore their pajamas as they climbed into bed, Christopher found
himself dressed in a blue satin gown. The dream was hardly
surprising for that night, visiting the home of Mary, a local woman
who had befriended him, he had, indeed, gone to bed dressed in a
frilly nightie borrowed from her daughter's wardrobe.
He awoke from his slumber suddenly, light streaming into the
girlishly decorated bedroom as Carolyn, the beautiful housekeeper
flung the curtains wide. "Wake up, sleepyhead" whispered the maid
in his ear. "Breakfast will be ready in just a few minutes." As
the cobwebs cleared from his brain, the activities of the previous
evening flooded back into his consciousness. As if somehow
disbelieving, he quickly peeked beneath the satin sheet, blushing as
his feminine attire was confirmed. "Come on, sweetheart - we'll
have to hurry" Carolyn said as she threw back the covers. The
teenage boy, startled tried to cover himself, but the maid just
grinned and, taking his hand, pulled him from the bed. "Here, hon,
slip on your robe and let's wash your face" she said, holding the
diaphanous, lace-trimmed bed jacket. As the boy slipped his arms
thru the flowing sleeves, she smoothed it over his shoulders letting
it settle lightly over the much shorter pink babydoll. Leading the
youngster into the bathroom, she draped a fluffy towel around his
shoulders and then, lathering a soft facecloth with fragrant soap,
began to wash the sleep from his eyes. After rinsing the lather
from his smooth skin, Carolyn gently patted his face dry with a soft
absorbent towel. Just as the night before, Christopher stood
passively, unsure of his feelings but somehow almost under a spell
as everything was being done for him. Unused to such pampering, he
found it quite pleasurable. Taking a toothbrush and even squeezing
the paste on it for him, "You finish brushing now, Chrissy; I'll
find your slippers."
Newly refreshed, he sheepishly returned to the bedroom where
Carolyn motioned him to the small seat facing the mirrored vanity.
Seated before the mirror, his eyes were drawn to the lace trimmed
bodice of his dressing gown. As the maid stood at his back, slowly
brushing his longish blonde hair with an ornate silver brush, his
mind reeled. "This is crazy" he thought, "she's treating me just
like a little girl or something". Despite his embarassment,
however, the more overpowering emotion was guilt, guilt that beneath
the blush, he actually delighted in her ministrations. He felt he
should put a stop to all this, but the gentle stroking of the brush
and the silky touch of his gown and panties on his skin seemed
excuse enough to postpone any rebellion. His mind was brought back
from his revelry as Carolyn knelt and slipped a pair of pink satin
slippers over his feet. The image of a princess being attended by
her ladies-in-waiting rushed thru Chris' brain as the maid took his
hand and brought him to his feet. "Oh dear, we'll have to hurry; we
can't leave Mistress waiting."
Though the backless slippers had but short wedge heels, the boy
took hesitent steps. "Let me help you, sweetheart". Reaching her
hand around his smoothly covered waist, Carolyn assisted the
femininely gowned boy from the room and down the wide stairs to the
brightly decorated dining room. Again the input from the boy's
senses seemed almost overwelming. Here he was, being supported by a
beautiful woman dressed in the briefest of costumes and smelling of
the most wonderful perfume, her arm encircling his waist and pulling
him close, all the while his own skin sheathed in the silkiest of
fabrics; and more, not only was his attire softly arrousing as it
brushed his thighs, it was exquisitely feminine.
"Good Morning, Chrissy" greeted Mary, his host as they entered
the room. "Did you sleep well, darling?" she queried as Carolyn led
the boy to her waiting arms. "I know a big boy like you doesn't
want to hear it, but you look very pretty in Susan's nightie" she
cooed as she enveloped the boy in her arms. "I'm sorry about your
lost luggage but it wasn't so bad, was it, dear?" Blushing deeply
as she gently brushed a stray hair from her young guest's forehead,
he could only nod. "It's a shame boys never have the chance to wear
such pretty things and look so nice" she continued. "It's just not
the same around the house with Susan being away at school; she loved
playing dress-up with all her pretty clothes". As the boy took his
seat at the table, he noticed what must certainly be loneliness and
heartache in his host's eyes.
"Oh Carolyn, you'ld better try calling the school again and see
if they've found Chris' suitcase" Mary called to the maid as they
finished their breakfast of melon and toast. Unsure of his
emotions, Chris looked forward to finally getting back into jeans
and shirt. "I just tried again, M'am; they're still no answer at
the school" said Carolyn as she returned to the room. Noting the
distress in the boy's expression, Mary motioned him to her, and
cradling the still nightgowned lad in her lap, she hugged him
close. "Don't worry, sweetheart; we can't have you spending the
whole week in Susan's nightie, now can we?" Again, a sense of guilt
and shame came over the boy, for that very thought seemed somehow
appealing. "I suppose we'ld better drive over to the school;
perhaps your suitcase is still in the driveway where we left it"
comforted Mary. "In any case, it's time you were out of your
nightie and dressed".
Carolyn, take Chrissy upstairs" the maid was directed. " We'll
have to find something else for him to wear in the car." Taking her
charge in hand, Carolyn led him from the room and back up the long
curved stairway. Knowing that he would soon be out of the silky
gown, Chris seemed to take special note of its whisperlike
softness. As he climbed each step, he secretly delighted as the
lace hem caressed his thighs and panty-covered rear. Before they
were halfway up the long staircase, he couldn't help but notice
another sensation. The sensuous touch of the filmy fabric had had a
dramatic effect on his adolescent member as well. Growing more
tumescent with each caress, seemingly out of his control, it
strained against the lacy confines of his silky panties. This new
"problem" did note pass the notice of the sexily clad maid.
Smiling, she let her hand glide around the boy's waist and teasily
slowed their pace a bit. Her proximity made matters worse as the
added sensation of her touch roused the now flush boy even further.
At last reaching the bedroom, the boy, now almost quivering,
broke free and rushed into the bathroom to hide his embarassment.
"What is it? sweetheart" responded Carolyn, hurriedly following the
boy into the bath. There she found the boy, his cheeks ablaze,
covering himself with his hands as best he could. "Darling, don't
be embarassed" the maid said softly. "Did your lacy little nightie
do this?" she asked. Moving his hands from their position, she let
her fingertips glide over the front of his gown, her nails barely
brushing his now engorged penis. Her eyes noting the tentlike
bulge, she teased "It seems our little Christine enjoys being a
precious little girl, doesn't it?" Near fainting as she reached
beneath the hem of the babydoll and caressed his throbbing malehood,
the boy had to grab the edge of the sink to keep from falling. "Oh
Chrissy, look what you're doing to your frilly little panties; if it
wasn't for this, I'ld think you were sweet young girl". Moaning
softly, the boy, now a captive to the maid's intoxicating caress,
surrendered to the rush of pleasure. His body sheathed in delicate
silk, his feet shod in pom-pomed satin slippers, and his pantied and
swollen penis gently milked by Carolyn's enveloping fingers seemed
ready to explode. "You like your little panties? don't you,
sweetheart? cooed Carolyn. "You want to be a sweet little girl,
don't you?" At that, the young boy's penis shuddered and released
its pent up excitement into his pink panties.
Part 3 A SCHOOLBOY'S WEEKEND AWAY
Christopher stood quivering, for the second time since his
arrival, Carolyn had excited him to the point of sexual climax,
this time, however, he had erupted into the silky pink panties he
had been forced to wear after forgetting his own clothes back at
the academy. On the verge of collapse, the scantily dressed
maid helped the embarassed boy to the padded bench opposite the
tub.
"You do look precious, Chrissy, but you really needn't
blush. It's plain you love your pretty nightgown and panties;
I'ld find it even more unusual if you didn't". The teenager
looked up into the maid's eyes quizically. "What do you mean?"
he asked. "It's just as Mistress said" she went on, "Boys are so
deprived, never able to dress up in pretty dresses and nighties
like girls. Forgetting your suitcase has given you an chance to
see just how nice wearing silky frillies can be."
"But I'm a boy! I shouldn't feel this way" he answered
ashamedly. "Don't be silly, honey" she said slowly lowering the
now stained panties down his legs. "There's no reason boys
shouldn't be able to feel pretty like their sisters." Taking a
soft washcloth, she carefully washed the boy. Not since early
childhood had anyone seen him so intimately, though considering
the occurances of the last day, there was little left to feel
embarassed about. Both Carolyn and her mistress had treated him
with a kindness and love he'd been without since leaving for
school at summer's end. "Come along now, Chrissy; let's find
something especially pretty for you to wear in the car."
"You want me to wear a dress when we drive over to school?"
he questioned, his voice almost faultering. "Don't worry
darling; before I'm finished, your own own mother would swear you
were her daughter rather than her son" Carolyn joked. "And I
don't want to hear any excuses; I know you're just dying to wear
a cute little dress and have your hair curled." Though he didn't
answer, Chris knew she was right. Yesterday he wouldn't have
imagined it, but like so much that had transpired since his
arrival, he was certain the day ahead would prove most exciting.
Just then, Mary entered the room. "And just what are you two
scheming in here? she said with a smile. "Why, Christine was
just telling me how much she way looking forward to going for a
little drive" the maid answered, her eyes twinkling. "Oh, I
see....didn't I tell you wearing Susan's things wouldn't be so
bad, sweetheart? she asked as she hugged the boy to her. "It'll
be just like having Susan home again, won't it, M'am?"
volunteered Carolyn. "Indeed it will; come along now Christine,
we'll have to pick out something especially pretty" Mary said,
leading their guest back into the bedroom. Remembering his now
lack of panties, the boy clutched the lace-trimmed robe tightly
around the nightgown, and sheepishly followed, the anticipation
of actually leaving the mansion while dressed as a young girl
building with each tick of the clock.
"Let's see now" Mary thought aloud, throwing open the sliding
mirrored doors lining the wall of the bedroom. The boy's eyes
widened as row upon row of delightfully colorful dresses, skirts,
and blouses were revealed. "What do you think, Carolyn?" Mary
queried as she removed an exquisitely feminine pink dress from
the rack. Their guest couldn't take his eyes off the airy
creation. The dress was a beautful pastel satin, its bodice and
skirt highlighted with wide band of white lace. "I think our
little girl will look adorable in this, don't you agree,
Carolyn?"
"Oh Yes, M'am" the maid replied, her beautifully manicured
hand caressing the boy's cheek as he blushed deeply. "Isn't it
pretty, Christine?" she asked excitedly, winking at her employer.
"Well? Christine, what do you think?"
"Yes, it's very nice" he finally answered, both women smiling
at his obvious embarassment. "Nice?...judging from the look in
your eyes, I would have thought something more than just nice"
giggled the satin and petticoat clad maid. "I almost forgotten;
we'ld better find you a new pair of panties, hadn't we
sweetheart?" Opening the top drawer of the large chest near the
bed, Carolyn searched for a moment, then returned to display a
darling pair of white satin panties. They were trimmed in frilly
lace at both the waist and leg openings, and even more
elaborately across the seat with several rows of lace running
from one side to the other. "My goodness! Those are precious,
just perfect for my new niece's first day out and about" gushed
Mary. Stooping low, the maid held the panties open, and
steadying himself with a hand on her shoulder, the boy, one foot
at a time gingerly stepped into them. Trying to remain modest in
the presence of the two ladies, Chris attempted to hold the hem
of the babydoll nightie down as Carolyn slowly raised the
wondrously smooth panties up over his knees. Smiling up at the
red-faced youngster, she continued on, tugging the panties up all
the way and her hands hidden beneath his gown, smoothed them over
his recently drained member.
"There now...that's better, isn't it Hon?" she asked the
boy. Not waiting for a reply, she stood and began removing his
filmy robe. "Let's not waste any time, Chrissy dear" Mary said,
taking the hem of the babydoll in her hands and lifting it over
the boy's head. Standing before them in only his girlish new
panties and slippers, he tried again to cover himself. "Don't be
so shy, Chrissy; we'll have you all pretty again soon" laughed
his host. "I think our little girl should be properly powdered
before donning her pretty dress" mary directed the maid.
"Certainly, M'am" she answered taking a feathery puff from a wide-
mouthed jar on the vanity. His eyes closed tightly, she dusted
him generously with the sweet smelling body powder, coating his
shoulders and then moving down over his hairless chest and
finally down over each thigh. Returning from the dresser,
Carolyn held out a wispy white training bra. Unsure of what was
happening, the boy took a step back, but Mary promptly instructed
him to raise his arms and quit tarrying. His arms outstretched
before him, Carolyn slipped the lacy confection up over his
elbows, and reaching behind, clasped the hooks which secured the
silky garment. Though hardly needing any support for his non-
existant breasts, he did feel somewhat more modest.
Any relief was short-lived however, as turning to Mary, he
spotted what he knew to be a garter belt in her hand. In his
mind at least, wearing panties and a dress was one thing, but
being attired in something so totally feminine was somehow moving
to an entirely different plane. Entirely at their mercy however,
he resigned himself to whatever they had in mind. Circling his
waist with the satin and lace belt, Mary motioned him to the
vanity stool. Seated, he watched in apparent awe as Carolyn now
approached, a pair of sheer white stockings flowing from her
hand. Removing first one slipper then the other, the maid
carefully gathered the sleek looking nylon and then slipped the
stocking over his foot. "Raise your leg, sweetheart; a girl
should always take care to keep her nylons straight." As she
glided the wondrously silky stocking up Chris' leg, he breathing
became more of a gasp. It didn't help as she reached beneath his
little panties and guided the frilly garter tabs under and thru
before attaching each tautly to the lacy tops of the nylons.
Just as Carolyn fastened the last of the garters, Mary returned
from the large walk-in closet with a pair of white patent leather
low-heeled pumps. The front of each was decorated with a pink
satin bow. Still kneeling, Carolyn took the shoes and slipped
them on the boy's feet. "Oh, those are darling, Christine." she
said as standing, she looked down at the pretty little shoes.
"It's fortunate Christine and Susan are almost exactly the same
size; our little girl will certainly have quite a wardrobe from
which to choose" beamed Mary. Checking the length of the dress
hanging from the closet door, Carolyn remuged thru the back or
the closet and shortly reappeared, a shiny slip in her hand.
Though somewhat short like the dress itself, the skirt was very
full. Constructed of multiple layered taffeta and edged in
delicate lace top and bottom, it rustled deliciously as she
lowered it over the boy's upstretched arms. Together, with the
lad sandwiched between them, Carolyn and Mary adjusted the thin
shoulder straps until it hung perfectly, the smooth bodice
hugging his chest and the frothy skirt tickling his thighs.
"Don't you just adore this wonderful petticoat, honey?" Mary
asked, giving the skirt a shake. An almost impercepticle moan
escaped from their charge's lips as the loud frou-frou and the
silken touch of the lace brushing his nylon sheathed thighs
seemed to envelope him in a kind of soft cloud.
Taking him by the hand, Carolyn again led the boy to the
vanity where, after showing him how to sit properly in a skirt,
she turned him away from the mirror. "It's time we fixed your
face, dear" the maid said taking a broad bib-like cape and tying
it around the boy's neck and shoulders. "Just wait till I'm thru
with you, Christine; you won't even recognize yourself". After a
few minutes, the change was remarkable. Eyeshadow, a bit of
mascara, and blush had served to remove any hint of boyishness.
Lastly, lifting the youngster's chin gently, she brought a tube
of lipstick close. "Purse your lips for me, sweetheart" she
asked, and after responding with a coquettish pout, she coated
his lips with a pinkish gloss. "Excellent" complimented Mary; "a
little touch up with the curling iron and our little Chrissy will
be perfect". Still facing away from the mirror, the boy sat
quietly while Carolyn brushed and curled what had been longish
hair for a boy. After looking thru a small drawer in the
dresser, Mary approached with two matching satin ribbons, the
exact color of the dress. After tying each into a pretty bow on
either side of his head, both women smiled.
Still beaming, they pulled their guest to his feet. "Don't
look yet, Hon" instructed Mary, "let's slip your lovely dress on
first." Taking the pink satin smock from its hanger, Carolyn
directed the now petticoated boy to raise his arms carefully.
Watchful of his makeup and new hairdo, the women lowered the
beautiful garment over his head and outstretched arms. They
fussed and primped, tugging it down gently until it settled over
the fluffy petticoats. After fastening the row of buttons up the
back, the maid removed a long sash from the hanger and wrapped it
around the boy's waist, forming a large bow in the rear, giving
the dress an almost bustle like appearance.
The anticipation was excruciating, but when the two women at
last spun the boy to face his reflection, he almost fainted in
wonder. Looking back from the mirror was no teenage boy in a
dress. Instead was the most beautiful girl he had ever seen.
His eyes moved from her delicately painted face, down over the
bodice of her lace and ribbon trimmed dress, lower to where her
legs seemed to escape from a bouffant cloud of frothy skirts, and
finally down to the tiny pink bows which decorated her girlish
slippers. Christopher, now Christine seemed lost in a trance.
"How was this possible?" he thought to himself. As he turned to
see the reflection from another angle, it hit him. As the layers
of taffeta swished about his nylon-covered legs, there was no
mistake. This was no dreamlike image - this was him! He could
have remained before the mirror for hours had the two women not
awakened him from his reverie. "It's almost 10:30; if we're
going, we'ld better get along" warned Mary.
"Ooops, I almost forgot" exclaimed Carolyn, rushing to the
closet once more. After briefly searching, she turned with a
small white patent leather clutch and a pair of white glace
gloves in her hands. "We can't have you going and forgetting
your purse, now can we Christine?" she grinned. The gloves,
though snug, fit over his hands, ending just above the wrist in a
ruffled lace cuff. "Now, come along, sweetheart" said Mary,
trying to rush things along. With one last look in the mirror,
the boy...er..the girl raised a gloved hand and lightly patted a
stray curl back into place, then turning, was led from the room.
With the two women, one on either side, he was led down the
wide stairwell. Each held one of Christine's gloved hands to steady
the boy as he manuvered slowly down the stairs still a bit unsure of
himself in the low heels. With every step, his frothy petticoats
made a delightful frou-frou as they bounced and tickled his nylon-
sheathed thighs. Once again, the youngster could feel the
excitement build within the silky confines of his lace-trimmed
panties. Embarassed by his own reaction to the soft touch of his
exquisitely girlish attire, he tried to think of something else, but
even the smallest movement seemed to defeat him and hold hold his
mind captive to intoxicating caress his borrowed frillies.
Being November, there was an autumn chill in the air, and as
they stood in the entrance hall, Carolyn went to fetch her mistress'
sable coat. "You'ld better find something for our little girl, too"
Mary instructed. The maid quickly returned with a beautiful pink
woolen double breasted coat. Carefully she slipped it over the
lovely dress and fastened the front. Lastly, Carolyn took a hatbox
from the upper shelf and opening it, took out a wide brimmed straw
skimmer. "Hold your head up, dear" she asked as she tied a fancy
bow under Christine's chin. "There now, you look just adorable,
Honey" she said, her hand straightening the flared skirt of the
coat. Bending, she gave the boy a little kiss on the cheek and
opened the frontdoor.
"Come along, sweetheart" beamed Mary, taking the delicately
dressed boy's hand and with his skirts bobbing, walked together to
the car. Looking back as they drove down the avenue, he could see
Carolyn smiling and waving. Just yesterday, he had sat in the same
seat, but now, everything was so differnet. Instead of jeans, his
legs were now sheathed in smooth white stockings, and despite the
weight of the woolen coat, the multi-layered petticoat made his
skirt puff up all around him. He felt he was sitting on a cushion
of frills, his ornately trimmed panties only adding to the froth of
his skirts. Folding his gloved hands on his lap, he looked over to
Mary. She smiled down at him; "Don't look so nervous, dear. No one
is going to recognize you now."
They drove on, heading down the shaded boulevard toward the
academy. "I'm sure we'll find your suitcase, but it will be so much
of a shame; you look so pretty as a girl."
Blushing, the boy lowered his eyes in embarassment. "Really
dear, you should have been born a girl; wearing pretty dresses is
only half the fun." The gates of the school came into view.
"You'ld better let me do all the talking, dear. We wouldn't want
you to give yourself away." Christopher froze in his seat. "Oh
God" he thought to himself, wishing that he could somehow become
invisable. The large iron gate was shut, so Mary pulled up and
stopped just in front and got out. Seeing a lone priest working in
the garden, she called to him. The boy recognized him as Father
Patrick, one of the older faculty members who was more or less
retired now and spent most of his time tending the grounds.
"Father, I'm Mrs. Alexander and one of your students is staying with
me over the holiday. It seems we left without his suitcase. Did
you happen to come across it in the driveway last evening?"
"I'm afraid not; I was just up that way a little bit ago."
"I brought my neice along with me in the car; would it be an
inconvenience if we came in and looked for just a minute?"
Looking out to the car, the old priest smiled and waved to what
appeared to him a pretty young girl. "Oh, I'm afraid that's not
allowed; the academy is cloistered to women."
The boy couldn't overhear the conversation but noted the look
of surprise on Father Patrick's face. "Well, is it possible you
could ask one of the other fathers if they might have come across
it?"
"I'm sorry, Mrs. Alexander, everyone else is away for the
weekend now." Mary interupted "Oh, don't worry then Father; I'm
sorry we bothered you. I'm sure somehow we'll make due. Happy
Thanksgiving."
Christopher noticed the woman smile as she turned and returned
to the car, waving to the priest as he toddled away back to his
gardening. "Is something wrong? Won't they let us look for it?" he
asked her nervously.
"It seems it definitely against the rules to allow ladies
inside the grounds" and with a gleam in her eyes added "and as cute
as you look, sweetheart, I'm afraid that applies to you, too."
"What are we going to do? It'll be four days till it opens
now" the boy wondered aloud, a tone of alarm in his voice.
"Now, don't you worry your little head, dear; it seems you'll
get to play dress-up a little longer is all. It'll be wonderful
having a sweet little girl in the house all weekend, you'll see."
The teenager's cheeks turned a bright red, but not out of
embarassment from wearing such girlish clothes. Rather, it was
because deep within, he couldn't imagine anything nicer than
continuing this new and exciting experience for as long as he
could. The soft caress of the silky fabrics on his powdered skin
and the way the two women (especially Carolyn) pampered him was
drawing him in like a fly to a spider's web. There seemed no fight
in this little fly either, despite arguments to the contrary, he
inched toward their silken trap willingly.
With his mind distracted with thoughts of panties and
petticoats, Mary turned the car around and headed back home. After
parking the car in the drive and leading her young charge back into
the house, Mary explained what had transpired to the waiting maid.
Though she tried not to giggle, it was obvious to the boy, Carolyn
took great delight in his misfortune. "Don't look so sad, Chrissy;
there'll be time enough to try on all sorts of pretty things now.
It'll be just like having a real live Barbie Doll to dress for a few
days. Come monday, I'll wager you'll feel terrible wearing nasty
boy clothes."
Without her own family in the house (Mary was recently widowed
and her daughter was in college on the West Coast), Thanksgiving was
to be celebrated at a local restaurant. "It seems we'll have a
young lady joining us for dinner today, Carolyn, and not the
teenaged boy we were expecting" the older woman quipped. "Shouldn't
Miss Christine have a bath before we go, M'am?" the maid asked with
a mockingly serious tone. "But of course, I'm sure she'll want to
look and smell her best on her first time out to eat." Mary
responded, her voice equally serious in tone. The boy stood
nervously by as the two women joked, and as he fidgetted, the
rustling petticoats continued their unceasing caress. The thought
of actually going to a public restaurant while dressed as a young
prepubescent girl disturbed him momentarily, but he knew he was
powerless to alter their plans for him. In fact, the stirrings
under the boy's fluffy skirts spoke more of his concurrance rather
than any complaint.
"Go with Carolyn, darling; she'll get you all ready" Mary
whispered to the daintily dressed youngster, and gently pushed him
toward the stairs.
Once again, taking him by the hand, the maid seemed to treat
him more as a five-year old than the teenager he was. Rushing up
the stairs, pulling Chrissy behind her, the boy's skirts bounced and
rustled while below, Mary smiled up at the frothy vision as it
disappeared into the bedroom. Everything had gone according to
plan. In just one day, they had transformed the boy into a gaily
and exquisitely delicate little miss. And much to her delight, it
was obvious in his eyes that he was beginning to love this new life.
Part 5 A Weekend Away From School
by: Daisy Ambersen
Carolyn closed the door and directed her charge to the satin
ruffled vanity bench. The boy plopped down, one leg bent back under
him and looked back over his shoulder, the look in his eye as if
waiting for her next instruction. "My goodness! Christine! Is
that how a young lady behaves? If that's the way you treat Susan's
lovely dress, perhaps it's time to put you back into trousers!"
Startled, the boy didn't know what to think. Had she really offered
to end all of this? and, more to the point, is this what he really
wanted down deep? Reflecting on all the events of the previous 24
hours, it didn't take long for him to stand, and spreading his
petticoats and skirt carefully, more gracefully took his seat
again. "I'm sorry, Ma'm, I'll be more careful" he whispered, his
eyes downcast in shame.
"Yes, that's much better, sweetheart" answered Carolyn, a
knowing smile crossing her lips. "Sit here and I'll start your bath
water" she said, turning and entering the adjacent bathroom. The
boy's eyes followed her across the room, drawn to her long
stockinged legs and the brief skirt of her maid's dress. As her
hips swayed with each step, the youngster sat mesmerized. The sound
of water splashing in the tub filled the room as Carolyn re-entered
the bedroom and stood behind the seated boy. Lowering her head till
her face was reflected in the mirror framed by the pink ruffles
highlighting the shoulders of the dress they had him wear, she
wrapped her arms around him and gave him a squeeze. "You look so
precious, Honey. You've made Mistress very happy." His carefully
made up eyes looked at her in the mirror, asking for expanation
without a word. "Madam misses her daughter so much since she left
for college. Having you here dressed so prettily is just what the
doctor ordered I think" Carolyn responded. As the blush spread over
his face, the maid began untying the satin ribbons from Chris'
hair. Then, taking the silver hairbrush from the vanity, she
started brushing the tangles gently. "You don't know how happy it
makes me to see Madam smiling again" she went on. "I'm sure she'll
really hate to see her little girl go once the weekend is over."
The boy rested his head back against her wondrously fragrant bosom
as she slowly moved the brush through his longish curls. Closing
his eyes, he seemed to melt into her encompassing warmth.
"That's enough now, we have to move along" Carolyn roused him.
Taking his hand, she brought him to his feet and removed the
matching sash which circled the waist of the pink satin smock. As
he stood before the mirror, she undid the buttons in the back and
sliding the dress over his shoulders, let it fall to the floor.
After placing it on a scented hanger, she returned and did the same
with the bouffant slip. It collapsed into a mountain of froth
around his knees, and extending her hand for support, had him step
gingerly from the lace cloud. No sooner had she returned from the
large walk-in closet, then he felt her hands at his hips, taking the
frilled waistband of the silk and lace panties and drawing them
down, careful not to snag the delicate fabric on the frilled tabs of
his garter belt. As he tried to cover himself, she slipped the
white panties down over his knees and then gently lifted one foot,
then the other to leave him standing in only the matching training
bra and garter belt. He again looked in the mirror to see an image
which now made him almost tremble. With his hair newly brushed and
his face still made up, the sight of himself standing dressed as he
was with the sexily clad maid at his back unclasping his brassiere
seemed a dream.
She delicately took the each ribboned strap between her
beautifully manicured fingertips and pushed them down over the curve
of his shoulders. As she pressed her bosom against the now bare
skin of his back, she glided her hands down around his neck and then
lower till they covered the nipples of each breast. Cooing in his
ear, she brought him to a state of complete distraction, "You have
such lovely little breasts, Christine." Scraping the tip of her
fingernails over the now stiffening flesh, she teased "See how your
girlish little nipples stand up?" By this time, the excitement had
spread far beyond just his non-existent bosom; his thickening member
could no longer be hidden. Despite his efforts to hide it, his
erection protruded almost straight out. With one hand continuing to
caress his breasts, Carolyn reached around and took the disgarded
panties from the vanity, and placing them over his throbbing shaft,
began to milk the boy. "Ummmm, nice soft panties" she whispered in
his ear. She teased him unmercifully, "Does my darling little girl
like her pretty panties?" Her perfume filled his nostrils, her soft
lips caressed the nape of his neck. "You love your frilly new
things, don't you, Christine." As she slid the silky panties up
and down along his member, he began to shudder, "Yes! Yes! Make me
your little girl!!" With that, his shaft erupted into the delicate
little panties and he collapsed down onto the vanity seat.
Hugging the now exhausted boy against her, Carolyn ran her
fingers through his hair and kissed his forehead. "That's my girl,
my precious little Christine." Unsnapping the garters, she drew
the long white stockings down his legs, and removed them. Drawing
him to his feet, she unhooked the belt and laying it aside, led the
compliant boy into the bath. Shutting the water off, the large tub
was near overflowing with fragrant suds. She removed a silk scarf
from the linen closet and wrapping it around his head, tied his hair
up out of the way. Helping Christine into the water, she knelt
beside the tub and began to sponge the sweet smelling lather over
his shoulders and back. Lifting the yielding boy's arms, she
swabbed under them and then moved lower over his chest and lathered
his stomach. As Christine sat passively, the strikingly beautiful
maid reached beneath the surface and no part of his anatomy
unwashed. Taking a soft washcloth, she began to wash the makeup
from his still beardless face. "Close your eyes, dear" she warned
as she gently cleaned the last vestiges of mascara and eyeshadow
from his eyelids. Using the long hose sprayer, she rinsed the soap
off him, and then holding a soft towel up, had the boy step from the
tub. After Christine was properly powdered, Carolyn had him sit on
the bed as she selected his wardrobe for the afternoon's excursion.
A little over an hour later, Carolyn came into the den where
Mary was waiting. She no longer wore the brief maid's outfit, but
instead showed off her stunning figure in a long blue silk gown.
Mary, too had changed for their dinner out. Though certainly not a
beauty queen, the older woman still looked elegant in a stylish
black suit. "Is our guest ready?" Mary asked. "Yes, Ma'm, she'll
be right down." With that, Carolyn called up the stairs "Come down,
Honey. We're ready to leave." Christine appeared at the top of the
stairs. She was a lovely vision in white. The maid had certainly
chosen well for there wasn't a hint of masculinity left in the boy,
rather he (now she) looked the perfect little princess. The dress
was all white lace accented by delicate pink satin bows across the
bodice and at the puffy sleeves and hem. From their vantage point,
the two women could easily view what must have been several layers
of crinolines under the wide almost floating skirt. Around his
waist was a four inch wide pink satin sash tied at the hip with a
huge bow. He stepped carefully down the steps, his feet in white
patent leather mary janes, highlighted by white anklets trimmed with
a turned down pink lace cuff. Short white gloves covered his hands,
each tied at the wrist with matching pink satin bows. His hair was
styled exquisitely, his blond curls piled high and circled with a
tiny little tiara. Though the dress gave the impression of girl no
older than seven or eight, Christine's makeup appeared dramaticly
more grown up. It was obvious that in addition to lipgloss, blusher
and shadow, Carolyn had also made use of false eyelashes. His eyes
lowered, he stood at the bottom step and finally, his long lashes
fluttering, looked up expectantly at his host. "Oh Christine, you
look absolutely wonderful" exclaimed Mary, thoroughly pleased at the
latest transformation. "I wish Susan could be here to see how
darling you are." After donning their wraps, the two ladies led the
daintily dressed girl to the car for the drive downtown to the
restaurant.
Though a small town, the eatery was crowded with those who had
opted for Thanksgiving dinner out. The restaurant was the finest in
the area, it's oaken paneling and velvet draperies giving an
impression of aged elegance. The maitre-de greeted the trio warmly
and escorted them to a table on the slightly raised mezzanine. All
eyes were on the cute little girl as she made her way between the
other tables. Christina couldn't help but overhear the whispered
admirations as the other diners paused and noted the precious
darling accompaning Mrs.Alexander. Self-consciously, Christine took
his seat as the waiter held the chair for him, making sure to
gracefully spread his skirt and petticoat. It was with an almost
audible sigh of relief that Mary ordered for him. While the two
ladies ordered white wine, a Shirley Temple was suggested for the
younster. The meal itself was wonderful, though Christine felt on
pins and needles throughout. After the traditional turkey,
cranberry sauce and stuffing, Mary ordered pecan pie and coffee and
another softdrink for her niece.
Christine seemed to grow uncomfortable and Carolyn, taking
notice asked, "Is there something wrong, sweetheart?" Despite the
boy/girl's embarassment, Christine couldn't wait any longer. "I
have to use the restroom" he finally whispered. Smiling, the maid
quickly summoned the waiter and asked "Could you tell me where the
powderoom is? It seems our little guest had a bit too much to
drink." After being shown the way, Carolyn took sheepish girl by
the hand and led him down the hall to the door marked "Ladies".
Thankfully, the elegantly decorated room was otherwise unoccupied.
Carolyn latched the door to provide some privacy, and to Christine's
surprise, backed him into one of the stalls. Lifting the young
boy's skirt and petticoat, Carolyn seemed to take charge, "Here,
Honey, I'll help you. Hold your dress up now." As his cheeks
turned a deep red, his lace trimmed panties were lowered to his
knees and the maid inched him back till he was almost forced down on
the seat. To his chagrin, Carolyn then gently took his soft penis
in her hand and held it down, aiming it for him. "Go ahead, dear;
let me see my little girl tinkle." The boy felt totally mortified;
never had he been treated like such a completely helpless child.
Despite his humiliation, Carolyn smiled as the sound of water
splashing in the bowl echoed in the small stall. When he was
finished, instead of replacing his panties to their former position,
the maid had the boy stand, his petticoats still raised to waist
level. She took a tissue and gently dried the tip of his penis, and
with the frilly white panties still around his ankles, she opened
her purse and removed a small container. He looked down just as
she opened it and watched as she removed a soft feather puff. After
coating it with perfumed powder, she carefully dusted him, paying
attention to cover not only his genitals, but also down along the
length of his thighs. With one final caress, she patted his now
silky penis, and then reaching down, slowly pulled his panties back
to their original position. "All finished, sweetheart" she said,
helping to straighten his petticoats as they floated down over his
legs. After washing his hands, Carolyn had him face the mirror, and
taking a lipstick from the small white purse he carried, retouched
the creamy gloss that coated his lips. "Feel better now, Honey?"
she asked, opening the door and escorting the embarassed youngster
back to the table. Still blushing, Christine took her seat as
Carolyn's eyes met Mary's and the two women shared a knowing smile.
--
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