Teased into Crossdressing

by Kresha Matay

Mary had caught her stepson, David, looking up her skirt as they sat

watching TV. He was lying on the floor, at an angle to her crossed

knees. Casually, in an effort to be subtle, she adjusted the drape of

her misplaced skirt, at the same time reassuring herself she hadn't

exposed all that much. The most David could've seen was the welt of

her nylons, possibly the garter straps and maybe some bare thigh. This

wasn't the first time she had caught her stepson trying to see up her

skirts. She had caught him staring down her blouse when he held a

chair for her or down her robe when she bent to kiss him goodnight.

She suspected he was also guilty of peeking through the keyhole in both

her bedroom and the bathroom doors. While this adolescent voyeurism

had initially made her quite uncomfortable, Mary had recently become

aware that she secretly enjoyed being spied upon. Knowing her stepson

found her attractive boosted her ego. In the last few months she had

accepted his peeking and at times, was even guilty of provoking it.

David was sixteen, her only child by marriage. Ron, David's father had

been her husband for three years, then vanished one night without a

trace. His first wife, David's mother, had left both of them, for a

traveling salesman. Mary, who had dated Ron before he married David's

mother, got him on the rebound after the uncontested divorce.

Everything had gone well for awhile, even David's acceptance of her as

a surrogate mother. Then they began having problems. Ron went out for

cigarettes one night and never returned. A missing person's report had

been filed and the local police had investigated, but no clues to his

disappearance had ever been found. The court awarded David to Mary's

care after his real mother had refused to take him into her new

household.

At first, Mary thought her husband had met with foul play, but as the

years went by and no new evidence of his whereabouts was ever

discovered, she changed her mind. She accepted the fact he had just

left them to manage on their own. It was just recently that he had

been declared legally dead and the insurance company had reluctantly

paid Mary the settlement check.

During those seven years, Mary had taken an assortment of menial jobs

to support the two of them. None of which paid much, just enough to

get by. This left Mary little time for a social life of her own. She

eventually convinced herself it didn't really matter, it was better to

be without a man then to be hurt again. All she had was her jobs and

David. Performing the duties of both parents wasn't easy, but Mary did

it well and a warm and cohesive bond developed between stepmother and

stepson.

The settlement Mary received meant she would never have to work again.

These last six months had been wonderful for both Mary and David! A

new home, a new car, new clothes for both of them and most importantly

for Mary ... time. The time to spend on herself and David. She had

never allowed herself to become "frumpy" or even "mousy", but also had

never had the spare cash to really take care of her appearance. Now

she did! She transformed herself into an extremely attractive woman of

thirty-three, a woman who drew attention from both sexes, wherever she

went. Fortunately the basic bone structure, body features and feminine

symmetry had been her's from adolescence.

Mary was glad that David was finally showing an interest in the female

gender. David had been much slower than normal in reaching puberty.

At first Mary had merely ignored the fact he paid little if any

attention to girls. But when he reached the age of fifteen and still

exhibited no interest, nor developed any of the physical signs of

puberty, she became quite concerned. Taking him to a urologist, for a

complete physical examination, while embarrassing for both of them, had

relieved her concerns. The doctor, after a thorough exam, had assured

her David was quite normal and it would be just a matter of time before

the changes occurred. The doctor's diagnoses had proven correct. Just

before his sixteenth birthday the changes had begun. She was so

pleased that she allowed him certain liberties which she would have

never considered proper if she hadn't been so concerned.

David began to show interest in feminine clothing, most especially

women's undergarments. This she considered a good sign of his "growing

up". She remembered how curious her brothers had been when she started

wearing bras and nylons. In an effort to help David she decided to

"inadvertently" leave her lingerie piled on top of the dryer instead of

immediately putting it away as was her practice. After a day or so,

she noticed the garments had been examined. In addition, she began to

notice unexplained runs in her nylons and pantyhose. Mary accepted

this as the price of David's curiosity, assuming the snags and runs

were inadvertently caused by David's mishandling the sheer and delicate

materials.

Mary found she was beginning to enjoy the tricks he employed in his

efforts to spy on her. She rationalized that since it only involved

the two of them, it couldn't hurt. She was getting an "erotic charge"

whenever she became aware of his attempts. The feelings became so

enjoyable, she began to find ways to create them!

She would carelessly position herself so David could see up under her

skirts just past the welts of her hose. She would bend to the waist in

order to pick up a piece of imaginary lint when he was standing behind

her. She knew the effect the tightly drawn skirt would have on the

youth. She began wearing garterbelts and nylons instead of pantyhose

thereby upgrading her stepson's level of excitement.

Mary would quickly "dart" between the hall bath and her bedroom,

wrapped in only a towel. Later she would claim to have forgotten" her

robe. She would leave her bedroom door slightly ajar so David could

observe her in her nightgown as he passed her doorway. The only thing

Mary refused to do was allow David to see her naked. At times, she

would inadvertently "forget" a button or maybe even two on her blouse,

allowing him a peek at the upper rise of her breasts. Once, in a

playful mood, she even spilled some water on the kitchen floor as she

stood before the sink doing the dishes. Tossing David a roll of paper

towels, she asked?

"Honey, would you please wipe up the floor for mom so I don't have to

bend in this tight skirt?"

Mary leaned against the sink, her legs spread taut against the skirt

material. Looking back under her left arm ... she saw David, on his

hands and knees, his head at her ankles, his face turned upwards,

staring up her taut skirt, paying absolutely no attention to the spill.

Mary smiled to herself as she recognized the excitement on her stepson

features. He had the best view of her nylon clad thighs and panty

covered ass she had ever allowed. She could feel his warm breath on

her ankles and calfs as he moved to get an even better look. When she

felt her leg muscles begin to tremble, from her own excitement, she

decided he had seen enough. Calling down to him, she asked?

"How are you coming with getting it wiped up?"

"Almost finished, mom!" He hurriedly answered.

Quickly he wiped up the spill and adjusted his erection so his

stepmother wouldn't discover what he had actually been doing as he

knelt at her feet.

That was the most exposure she had ever allowed him. She never let him

actually see anything more than if she was lying on the beach in her

bathing suit, it was the act of teasing that excited her and brought

David back for more. She took erotic pleasure in the bulges that

formed in his pants and the actions he took to hide them from her. In

her mind, these were another sign he was growing up normally. Mary

actually rationalized she was helping her stepson "catch up". She

explained away her actions and any possible guilt, reasoning it was

better he experienced these "lessons" at home than with some unknown

teenage girl which he might get pregnant and thereby ruin both their

lives.

Some of David's actions, she didn't understand. Those she couldn't

explain, she ignored, even though they preyed on her mind whenever she

was alone. The one that bothered her the most, was not being able to

discover what he did when he hid out in his locked room. She suspected

her stepson withdrew into a fantasy world, plotting his next attempt to

see her naked.

What David really did in his room was ... masturbate! Within the last

seven months he had discovered the female of the species and the effect

these discoveries had on his penis. Puberty, long delayed, had

attacked with a real vengeance. At first, not understanding what was

happening to him, he sought advice. Since he was too embarrassed to

talk to his stepmother, he asked an older boy at school. This was at

first greeted with laughter and then with the advice to "steal" a pair

of his mother's panties from the hamper and rub them over his dick and

balls whenever he got the urge.

Unsure of the advice, he nonetheless did as instructed and obtained the

obvious result ... orgasm. Everyday for the next week he performed

the same act until the panties were no longer smooth and silky, but

caked with his emissions. Assuming his stepmother would never miss one

pair of panties, he stuffed them into the garbage can, behind the

house. Realizing he couldn't continue throwing away his stepmother's

panties without eventually being discovered, he stole two pair off a

neighbour's clothesline. These he hid in the back of his closet.

One day, when he was left alone in the house, he decided, "If the

panties feel so good against my dick, I wonder how they'd feel if I

wore them?" Quickly undressing, he stepped into the pale blue pair he

had stolen, pulled them up his legs and snuggled them around his ass.

The coolness and silkiness of the material created an instant hard-on.

He had a difficult time getting the panties to "sit" right, like the

way they fit those models in the Penny's catalog, until he discovered

that bending his dick backwards between his legs helped. Standing

before a mirror, he posed his lower torso mimicking how he remembered

the models in the catalogs stood. It was definitely an exaggerated but

fun experience for the youth. He enjoyed the silky feelings of the

material against his skin and spent long minutes rubbing his hands over

his panty covered ass, while fantasizing it was a woman's buns he was

stroking.

Pleased with himself he nervously snuck into Mary's room. There he

found a discarded pair of his stepmother's nylons. They were still

attached to a garterbelt. Cautious to the extreme, David worked at the

unfamiliar garment until through trial and error he discovered how to

roll the silky hose up his trembling legs and reattach the garters. By

this time his hard-on was raging, no longer held back between his legs.

Sitting on the edge of his stepmother's bed, he crossed and recrossed

his legs, reveling in the feel and texture of the hose. Running his

hands over his silken legs was so exciting, he was losing control. In

fear, he quickly removed the garments, rushed to the john and orgasmed

into some tissues.

This was his first step into crossdressing, but only the first. The

experience had been far too satisfying not to repeat. From that first

exciting moment, whenever he was alone, he would sneak into Mary's

room, carefully open her lingerie drawers and borrow a bra, panties and

nylons. His stepmother always kept her lingerie drawers disorganized

so she never discovered her pretties had been disturbed. David quickly

progressed to wearing his stepmother's dresses, blouses, skirts, slips,

nightgowns and high heels. Make-up, a wig and earrings became the next

step in his adventures. Each new adventure increased his obsession

with feminine clothing and the sensuous pleasure he derived from

crossdressing and acting feminine. He continued to practice his

gender-switching, experimenting like any other teenage girl would and

actually became adept at wearing feminine attire. As he became more

and more comfortable with each new advancement. He began to fantasize

what his life could have been if he was a pretty and sensuous female

instead of a male. More and more his daydreams and desires revolved

around ways he could change his gender. Like other young boys who have

had the same fantasies he created dreams in which he utilized various

methods to become female. They didn't have to based in reality. One

gender change came about due to a witch's magic spell, another, finding

a bottle with a genie inside, a third, from a mysterious combination of

chemicals. It didn't matter how outrageous the method his mind created

to explain his change, it only mattered that he had found a means to

become female ... if only in his mind.

Now he began to "study" females, as a different gender. Whenever he

discovered a disparity in male vs. female mannerisms, he went home and

practiced until satisfied he had copied it perfectly. Whenever he

crossdressed, he would stand before the mirror and create fantasy

conversations speaking in a girlish voice. With enough practice he

managed to develop this feminine voice, also to perfection. David

initiated an alter ego. One which made him feel more attractive.

Once tempted, his young mind became obsessed with women, their clothes

their mannerisms and their bodies. Under the pretense of looking at

sporting goods, toys and tools, he "memorized" the women's clothing and

lingerie sections of every catalog he found around the house. He

became an expert on lingerie and foundation garments. He ascertained

the purpose each item fulfilled towards enhancing a woman's figure. He

was disappointed his stepmother didn't own many of the foundation

garments, but realized she had no real need for some of them. Matching

Mary's lingerie labels against the catalog descriptions, he learned to

distinguish the subtle differences of each material. Using this same

method, he studied the labels of the dresses, skirts and blouses he

found in Mary's closet. Diligently applying himself, he soon became

expert enough to determine what any woman was wearing, the material

from which her skirt, blouse or dress was made and in many cases the

fashion designer who offered it for sale.

For every time his stepmother caught him trying to see up her skirt, or

down her blouse, there were twenty more times he got away with it.

When he wasn't fantasizing about being dressed in women's clothes, he

dreamed of going out with Mary ... as her daughter. He knew he

couldn't tell his stepmother about his crossdressing, but almost wished

she would catch him, thereby, finally bringing it out in the open.

The desire to actually see a naked woman's body grew so strong, he no

longer could control his emotions. Finally he decided to take a bold

step ... hiding out in Mary's bedroom and watching as she undressed.

If he got caught spying on her, he reasoned, he would be forced to

admit his fantasies about seeing her nude and might even be brave

enough to admit to his crossdressing. Telling Mary he was going out

for awhile, he slipped back into the house, into her bedroom, and hid

under her bed. David knew she was going dress shopping shortly and

hoped she would change her outfit. He wasn't sure he would see her

naked, but at least he would see her in just a bra and panties.

After about twenty minutes (it seemed like an eternity), Mary entered

her bedroom. Stripping to her "undies" she sat before the dressing

table and did her make-up and hair. Mary had no idea she was being

"spied" upon. She went through all the normal motions of getting

ready. To David lying under the bed, each step in her preparations was

exciting and educational. He was able to barely glimpse the crack of

her ass through the sheer white panties she wore, but no more. As his

stepmother would reach for something, she would turn slightly. This

afforded him a partial view of her bra covered breasts. While he had

previously "caught" sight of her in a bra, for some reason this time

was more exciting since she didn't know he was there. His hard-on

pushed up against his stomach, forcing David to adjust his position.

He wanted to play with himself, but was afraid he might ejaculate in

his pants. While David lay there, holding his breath, Mary reached

into her drawers, select a garterbelt, sheer black hose and matching

bra and panty set, the same set he had worn just the day before.

Totally unaware of her stepson's presence, Mary reached behind her

back, unhooked her bra and slipped her arms out from the straps. Then,

as every woman does after removing her bra, she massaged "life" back

into her sensitive breasts, squeezing, kneading and rubbing the firm

mounds of flesh. David realized what his stepmother was doing even

though his view was mostly blocked by her back. Picturing the scene,

in his mind and seeing her nude back, his mind raced. "Oh how I wish I

had breasts like Mary's!" With a start, he came to the realization that

he no longer thought of her in a sexual sense. His earlier fantasies

about Mary had including touching her breasts, etc. Now he wanted to

have breasts like hers! He no longer felt desire for her, but instead

wanted to be like his stepmother ... a female! His goal had changed.

David missed his big chance when Mary inserted her thumbs into the

elastic waist of her panties and slid them down off her legs, tossing

them to the floor. It had happened so fast the hidden youth wasn't

able to see anything other than the quick flash of the crack separating

the moons of Mary's asscheeks.

Now her "tan lines" were visible. Straining to see more, he adjusted

his position, and in doing so, he lightly bumped his head against the

bedframe. The pain, not serious, made him wince. He didn't realize

the sound his contact with the frame made was so loud. He assumed his

stepmother hadn't heard it. He was mistaken!

Mary had definitely heard the bump. She also had seen the movement of

the dust-ruffle, reflected in her vanity mirror. Mary controlled her

natural reaction to cover herself. She immediately realized it had to

be David under the bed. This was more than just peeking, he had

actually seen her naked breasts and ass! Looking at her image in the

mirror she held a silent discourse with her reflection.

"I can do one of two things, I can continue as if I didn't know he was

there, or I can start a yelling, screaming fit. If I throw a fit, it

won't change the fact that he's already seen me naked, besides maybe

I'm partially to blame. I've teased the poor boy to the point he

probably couldn't control his desire to see a naked woman and who else

is there for him to spy on?"

Smiling into the mirror and recognizing the mischievous twinkle in the

eyes of her reflected image, she continued her silent discourse.

"Afterall, what actual damage has been done? I'm sure every young boy

tries to see his mother naked and most, I imagine, succeed. I tried to

see my father and my brothers naked when I was a young girl! It's

better if I don't let on, that way nether one of us needs to be

embarrassed."

Pausing a moment, she mused. "Besides I bet I can have some fun with

this situation."

The longer she contemplated her decision, the more thrilled she became.

Mary's rising emotional state overcame her natural inclination towards

modesty and therefore she decided to "give" her stepson a "show" he

would long remember. Deciding how much she would permit him to see,

she put her verdict into action. Turning sideways on the stool, she

swung her legs parallel to the dressing table and David's view. Mary's

legs now faced away from David thereby affording her stepson a most

generous view of her nakedness but at the same time she avoided

exposing her womanhood to the hidden youth. As he watched, Mary went

through a series of exaggerated motions as she attached her garterbelt.

David was forced to bite his clenched knuckle in order to muffle his

excited moan! There sat his stepmother ... naked, her breasts

exposed. To her stepson's excited stare the full, round mounds gently

swaying and bobbing before him were perfect. Mary's pert reddish brown

nipples, because of her own excitement, stood out from her equally

large brown aureole. The breasts showed just the faintest hint of a

muscle sag, but for her age and David's lack of experience, they were

outstanding. As she moved, they bounced, jiggled or swayed. Having

never seen an adult woman's breasts, he lay there mesmerized by their

beauty. Mary allowed him a generous examination, delaying her normal

method of dressing to insure he would remember every rounded curve of

her sensuous orbs.

David's concentration was snapped to attention when his stepmother bent

down to roll her sheer black nylons up her legs, past her knees and

over her thighs. Mary spent a long moment adjusting the proper fit of

each nylon. She sat, raising and extending one leg after the other,

just like Mrs. Robinson, running her fingerpads along the sheer

material and stretching it taut against her smooth leg muscles.

Finding imaginary fault with each leg, Mary removed each nylon and

repeated the operation. David, meanwhile, thought he might have seen

the merest hint of her hairy mound when Mary alternately raised each

extended leg into the air, to run her hands up and down her legs ...

but he wasn't sure.

After attaching the garters, she inserted both feet into her panties

and "squiggled" herself into the red silk material. Slipping her arms

into her matching Demi-bra, she teasingly adjusted how her breasts fit

within the cups. Then caught the hook in front. Raising her arms, she

did an exaggerated and sensuous stretch. This caused her breasts to

push up and out and bent her back into a cat-like pose. A pose every

woman has performed since the beginning of time to entice members of

the male gender. Momentarily maintaining the stretch, Mary examined

herself in the mirror. She smiled. Finally letting her arms drop, she

rose to her feet. Bending over, knees locked, she made a final

adjustment to her nylons thereby offering David an excellent view of

her pantied ass. The angle was perfect, he saw the triangle of her

crotch as the silken material bunched around the pouting lips of her

womanhood. As Mary turned and walked to the closet, David was

fleetingly rewarded with an eyeful of her panty covered muff. This was

too much for the feverishly excited minor. Biting his knuckle, he came

in his pants!

Mary, realizing how excited she herself was getting and also aware

there would be no opportunity to relieve herself, had chosen to cut the

"show" short. Deciding to give her stepson one last thrilling glimpse,

she took a few steps, stopped, paused a moment as if in contemplation

of what to do next, then, with determination, strode to her closet,

gone from David's view. Within two minutes she returned carrying a

dress in her outstretched arms. Stepping into the lined dress, she

then slipped on some heels and left the room and the house.

David continued to lie hidden ... till he was certain Mary had driven

away. Slithering out from under the bed, he picked up his stepmother's

discarded panties and rushed to the bathroom, where he proceeded to

liberate his throbbing manhood from the gooey mess inside his pants.

It took but a few quick strokes ... and he came a second time, more

profusely than before. To David's utter amazement his organ remained

rigid. David's final orgasm came more slowly, but as potent. Barely

able to stand, he replaced Mary's panties where she had dropped them,

retired to his room and fell asleep dreaming of what had occurred.

Mary, as she drove away, decided she had taken the correct tack. The

image of her stepson masturbating after she left brought a smile to her

face.

"I wonder if I should teach him a lesson and spy on him. Maybe I will,

afterall, turnabout is fair play!"

Other things were happening in David's life. As his desire to be

female grew, David no longer hung out with the guys, but took every

opportunity to spend time with girls his own age. They at first were

naturally suspicious of his motives, but soon came to realize he wasn't

a threat and eventually even welcomed his membership in their

close-knit group. They "felt" he "understood" them, and treated them

as equals, not like his counterparts. The girls; Karen, Kathy, Joyce,

Susan and Tammi were just as sexually naive as David. Within a brief

period, they recognized the value of having a nonthreatening male as a

member of their clique and accepted him. This opened a new world to

David! Now, comfortable in his presence they began to openly discuss

all the topics that young girls talk about, namely boys, clothes, their

looks, their bodies and of course sex as if he either wasn't there or

was female like them. David joined in the conversations as their male

authority. He offered constructive observations without the usual

hidden male agendas and made practical suggestions as to what made guys

notice girls. His astute proposals were tested and found helpful in

their attempts to catch the attention of boys. The girls became so

comfortable with his presence, they never became anxious over their

stance, dress or the possible disclosure of their budding bodies to his

view. In David they quickly recognized his fashion expertise and

always sought his opinions on different styles and selection of

clothing. It started with skirts, tops and shoes, then naturally

progressed to lace on a slip, then bras and panties ... till that one

pivotal day. It was over Christmas vacation and happened at Karen's

house. Her parents both worked and wouldn't return till much later in

the day. The girls were in an especially playful and fun-loving

holiday mood. They decided to "dress-up" in the clothes, shoes,

hairpieces and of Karen's mother. They took turns playing the mistress

of the house, while David was expected to act the part of the husband.

They had played this game many times before, but today it would be

different. Instead of leaving the room to change, the girls decided to

see if they could shame David by changing in front of him. When he

didn't react as they had expected, they confronted David.

"We don't think it's proper that you see us in our bras and panties

while you sit there fully clothed. How do we know you won't tell

everyone. We think you should strip down to your shorts just like us.

If you don't, you'll have to leave and never be with us again."

David, realizing he had no option if he wanted to remain ... agreed to

their demand. Afterall, he silently mused, for a boy, it was just like

being on the beach in a pair of trunks. The problem was ... he wasn't

wearing shorts! That morning he had worn the pink lacy panties he had

stolen from his neighbor! David had become so accustomed to wearing

panties, he had forgotten. When he dropped his pants the girls saw his

groin was covered in pink panties with delicate lace at the waist and

legholes. The girls, stunned for a moment, quickly recovered, then

began to laugh uproariously. Catching her breath, Karen giggled.

"Now we know why you like to be with us! You really want to be a

girl!"

David made a grab for his clothes, but before he could cover-up, he was

seized by five pairs of arms, wrestled to the floor and pinned to the

carpet. When he realized he couldn't overpower his assailants, he

stopped struggling. The girls allowed him to sit up, but still firmly

held his arms and legs. Each girl, in turn, investigated how David

looked in panties. He was "forced" to stand, twist, turn and twirl

around so all could see how the ultra-feminine panties fit his male

frame. Now instead of being embarrassed, he was secretly enjoying

their interest. After all five girls had their fun, he was allowed to

sit back down on the floor. Kathy, silently surveying the other four,

made a gesture to which the others nodded agreement, then stated.

"If you don't want us to tell everyone your a sissy who wears girl's

panties, you better stay seated while we go and talk about what to do

with you."

Searching their faces, he knew the threat was real. Nodding his head

in acceptance, he remained seated as the girls went into the next room

to discuss his fate. They weren't gone but 10 minutes, but to David,

fearful of what they might decide, it seemed like hours. When they

returned, the girls sat around him and then made their demands.

Kathy spoke first, "David, we really like you and we'd like you to stay

a member of our little group. We trust you! You've really been a big

help to all of us! If you want to dress as a girl, we don't care.

It's OK with us ... but you'll have to do it our way. Afterall, what

would people think if it got out what we were doing. Our reputations

would surely be ruined! You must agree to everything we demand of you

and always without protest. If you do what we ask, we promise never to

speak of this outside of the group. Since you like to dress like a

girl ... we'll dress you like one of us. We think it'll be a lot of

fun! Some of the things you'll have to learn won't come easily and may

even be embarrassing. But that's the price you'll have to pay if you

want to be one of us. We can't be discovered playing with a boy

dressed up as a girl. No matter what excuse, nobody would accept it!"

Now Tammi spoke, "We're going to change your name to Darla. That's

short for darling and that's what we want you to become ... OUR

DARLING! Whenever we get together we'll transform you into Darla. If

you "pass", and we think you'll make a very pretty girl, we'll reward

your hard work by inviting you to a "slumber party". You'll get to

sleep between us in the same bed. At the slumber party, we'll play

girl games, like teasing each other's hair, applying new make-up,

tickling and other things we'll tell you about later. If your nice to

us, we may even take you out clothes shopping! I'll bet you'd like

that. Just imagine yourself in the women's department trying on new

skirts, blouses and dresses with us there to help you. Think how much

fun it'll be to "fool" the shoppers and saleswoman."

Karen interrupted, "Since you'll be one of us, we'll show you what we

look like ... naked. That way you'll know what a "real" girl looks

like. Of course, we expect to see you naked also. I'm going to take

Polaroid pictures of you dressed as Darla. We'll be in the pictures

with you. That way we'll all be protected. We think it'll be lot's of

fun. Well, those are our terms, do you agree?"

As the reader can imagine, David couldn't have been more delighted.

The girls were providing most of the features of which his fantasies

were comprised. He would be seeing his girlfriends naked. He would be

assisted in crossdressing, taught to "pass", attend slumber parties and

enjoy all the girl things he so wished to be a part of his life. He

would go shopping and really "be one of the girls". Without even a

moments hesitation, he quickly agreed to their terms.

The girls were just as pleased and squealed in glee. None of them had

ever seen a naked male body and looked forward to seeing David's.

Also, they had not fully outgrown their childhood game of playing with

dolls, dressing them in different outfits, etc. David would become

their life-size doll and plaything. It was decided, that Joyce and

Susan, who lived nearby, would run home and bring back additional

clothing for David to try on. Susan, since no one was home at her

household, also wisely thought to borrow some "sexier" clothes that

belonged to her mother. These included a garterbelt, nylons and a pair

of high heels. If questioned later, she planned to explain the girls

were playing "adult dress-up". Since they had done this before, she

knew her mother would be pacified. After they returned, the fun really

began. When he removed his pink panties, you could have shot off a

canon and nobody would have noticed. Letting his legs fall open he

exposed his cock and balls. If he finally hadn't stepped away, they

would have spent hours playing with his maleness. Afterall he

defended, the real purpose of the afternoon was to transform him into

their Darla doll.

Even though David had reached puberty, he was still quite hairless and

what he did have was light in color, so there was no need to shave his

legs or chest. As they laid out the different feminine outfits, David

began to search the pile of lingerie Susan had brought back. Selecting

the black lace garterbelt, he fastened the hook and twisted it into

position. Susan noticed and got the attention of the others. Without

comment, they all took seats and watched, fascinated by his actions.

Meanwhile David picked a pair of taupe colored nylons, inserted his toe

into one and rolled it up his outstretched leg. Fastening the garters

to the welt, he stroked the hose into place. When he had completed the

process with the other nylon, he stood. Then deciding he need a bra,

he said with an impish grin.

"Kathy, why don't you hand me your bra, I can't get dressed without

one."

This suggestion was met with gales of laughter and pressure from the

other girls to comply. Kathy, who had the largest tits, the reason

David had selected her, was reluctant unless the other girls also

removed their bras. When Susan, the least bashful, moved to unhook the

front of hers, the others followed suit. One by one, they, shyly at

first and then more sensually, exposed their firm youthful breasts.

Each girls breasts were of different size and shape, but all were

beautiful.

David was in all his glory! Before his stunned eyes were five sets of

young breasts, ranging from Joyce's budding "nubbins" through Kathy's

36/C cups. Susan, reached up her hands and cupped hers. Teasing him

by bouncing her hands, she questioned provocatively.

"Darla sweetie, wouldn't you like to own a pair like these?"

David smiled his agreement and commented, "They're all soooo very

beautiful, I would be truly satisfied if I had breasts as sexy looking

as any of you."

If the girls had any remaining reservations about their actions, his

comment eliminated their doubts and further endeared Darla to them.

Taking the still warm bra from Kathy's outstretched hand, he proceeded

to put it on. Then using his and Karen's socks, he filled it. Picking

up a long blond wig, which Karen had laid in front of him, he placed it

atop his head. As he stroked the tresses into place he looked around

until he saw them. They were partially hidden under a beautiful, white

silk nighty. Reaching under the nighty, he extracted a pair of black

leather 3" high heels. Inserting his toes, he casually slipped the

shoes onto his nylon encased feet and "pranced" across the room.

Extremely proud of his ability to walk in heels he "minced" his way to

where the girls sat. Back and forth he swished, from one end of the

room to the other. Throwing a look back over his shoulder, he enjoyed

the stunned look on their faces. He had the feminine mannerisms and

walk down perfectly. When one of the girls commented.

"His legs look better in nylons and heels than mine!" ... he threw her

a kiss.

Turning his back to them, he bent forward at the waist. Running his

fingers from his ankle to the welt of his nylon, he again adjusted the

hose. Tammi began to clap, followed quickly by the others. All five

girls had seen their mothers perform the same motion to straighten

their hose. Again turning and covering his pantied crotch with both

hands, in the classic "September Morn" pose, he asked in his feminine

voice.

"Isn't anyone going to give the new girl a hug and kiss to welcome her

into the group?"

For the rest of his life, David would consider this his "Coming-out

Day"!

During the next five months all six "girls" had a wonderful time

learning about the opposite gender. They played "Show Me Yours and

We'll Show You Ours".

The girls were correct, he was able to easily "pass" as Darla. After a

couple of "test" situations (short trips around the block), David

gained sufficient confidence to join the girl's at a local Teen-Club

dance. He had absolutely no problem convincing everyone he was a

visiting cousin of Karen's. Darla tried to refuse all the boys who

asked her to dance, but after so many requests and pressure from the

girls, he finally accepted. He soon realized it was easier to follow

then to lead. A couple of the boys tried to hold Darla too tight

and/or "cop a feel" of his panty clad ass as they danced Darla around

the room. Gently, but firmly, she corrected the way she was being held

and warned her partner, "If you try that again, I'll slap you!" After a

few similar warnings, the word got around and Darla was only asked to

dance by the polite ones.

Going to the ladies room was also quite an experience. Tammi and Susan

went with him. After relieving themselves, they loitered a bit,

listening to the conversations around them. David was surprised how

openly the girls exposed their partially clad bodies and also how

intimately they helped their girlfriends adjust their clothing. Some

of the conversations he overheard were absolutely shocking! He had

never imagined young girls were as sexually open or "hungry" as these

endorsed.

After the dance, the six compared notes. Teasing Darla about the

numerous requests they received for information about her and the times

she was asked for her phone number. Darla admitted she was thrilled by

the attention and found it nicer being asked to dance without the fear

of rejection.

Kathy asked, "Did the boys turn you on?"

"No", she responded. "I felt no physical attraction towards them. It

certainly was a pleasant experience dancing with them, but mostly

because of the satisfaction I derived from convincing them I was female

and pretty."

Kathy wouldn't let up.

"How about the kiss I saw you get from Jimmy, Joyce's brother?" She

giggled, "It sure looked like you were enjoying yourself!"

Darla blushed a bright red, "He surprised me! Before I knew what he

was doing, Jimmy had me in a 'bear hug' and planted his lips against

mine. I was afraid to make a scene, so I let him kiss me. It wasn't

unpleasant, but it didn't excite me. Thank God, he didn't try to

'French' me, I don't know how I would have reacted to that! I think it

was just the realization of fooling him that was so nice. Besides if

you all hadn't done such a good job with my transformation, he wouldn't

have wanted to kiss me! For that, I guess, I should thank all of you!"

"Gee, I sure wish I could tell that smart-ass brother of mine how you

fooled him and how he was kissing a guy in girl's clothing. I could

'blackmail' him into doing anything I wanted!", Joyce giggled. "I

won't, but it sure would be great to hold over him."

After Darla's success at the dance, she was invited to more than one

slumber party, meeting the parents without anyone being the wiser. It

was at these parties she learned to apply her own make-up and style the

wig they had chipped in and bought her. Any day off from school, but

which their parent's worked, became a "special" holiday. They would

meet, assist their Darla in getting dressed and take a bus to a mall on

the other side of town. There the six girls would spend the day as any

other group of teenage girls would ... shopping for clothes and

cosmetics. The only drawback was the need to "dress-up" in skirts and

such in order to make Darla's "passing" easier. They taught Darla the

nuances of shopping, how to tease an attractive shoe salesman and how

to reject "come-ons" from teenage boys "stalking" the mall. After each

new experience they would return and compare notes on Darla's level of

performance. Suggestions were offered and practiced, so that by

summer, Darla had mastered her role-playing to everyone's total

satisfaction.

While David's transformation was happening, Mary was again becoming

concerned about David. She didn't understand the lack of attention he

paid her. He very seldom tried to look up her skirt or down her blouse

anymore. David, of course, was getting to see "the real thing" and no

longer felt the need to spy on her. But Mary didn't know this. She

was naturally concerned. He still didn't date. He would disappear for

hours and offer no explanations as to where he went. He supposedly

slept overnight at his buddies house's, but she had never met any of

them. He had also developed some strange mannerism. Mannerisms, Mary

viewed as feminine or maybe "gay" in nature. He walked differently, he

speech was more dramatic, he was gentler, better behaved and more soft

spoken. Her continued attempts to tease him were only partially

successful. In the hidden reaches of her mind a question began to

grow, "Was David becoming gay?"

"I think it's time for me to find out!"

What Mary wasn't ready to admit was ... she missed the sensual

excitement whenever David "peeked" at her. She had spent many a night

remembering the scene in her bedroom the afternoon he hid under her

bed. Driven by her concerns, Mary decided she must know why her

stepson was no longer interested in peeking at her. She remembered her

thoughts, in the car, after he had spied on her. "Turnabout is fair

play." A plan began to form. She would tell him he was going to be

home alone Friday night. She was going to visit her brother Phil in

Detroit and return late Saturday night. In reality, she would sneak

back into the house and hide herself. Knowing his stepmother was gone,

she felt David would relax and expose what he was doing on the sly.

Her only concern was David might invite his "gay" friend(s) over. She

was that sure he was turning from girls in favor of boys. Putting her

plan in motion, she informed David of her proposed trip at breakfast

Friday morning.

David was ecstatic. His first thoughts was to invite the girls over

for a party. They could have the house to themselves. As his

stepmother went upstairs to pack, he went for the phone. Calling

Kathy, he was informed that she had a date and couldn't make it. Call

after call was made, all with the same negative results. Each girl had

to do something either with dates or family and wouldn't be available.

David, somewhat despondently, said to each of his young friends that he

understood. To himself, he mused. "Well, I guess I'll just have to

have my fun alone tonight. I'll still have a good time! I've wanted

to try mom's new black dress, anyway. It will be Darla's house

tonight!"

Mary moved her time of departure up as she observed David's excitement

grow with each passing minute. She loaded her car and drove away about

3:00 PM. She had skipped lunch, deciding to grab a bite before she

returned giving David the time to become relaxed with his stepmother's

absence. She didn't think she'd have to remain hidden too long, but

was prepared to spend the night hidden in the closet ...if necessary.

At the restaurant, after her meal, she called home. When no one

answered, she smiled at how well her plan was working.

"David must have taken my suggestion and gone to Wendy's."

Parking the car around the block, she hurriedly "snuck" back inside and

hid herself in the hallway closet. Mary had checked it out already.

If David didn't bother closing his bedroom door, she could observe

everything he did through the adjustable slats in the closet door.

What she didn't take in to account, was that David would use her

bedroom. Therefore she wouldn't have the unobstructed view she

expected. She didn't have long to wait.

Mary heard David enter the house, close and then lock the door behind

himself. Surprised, she watched as he went around the house, tightly

closing all the curtains and shades. When he finished, he went to her

room. This again surprised her. From her oblique angle, she could see

only the area at the foot of her bed. Disappointed, she nonetheless

waited until she was sure that's where he would remain. Then taking a

chance, she silently positioned herself in the hall at the doorway to

her bedroom. Sneaking a peek inside, she saw David standing naked

before her dresser. She watched in utter amazement as her stepson

began selecting and then putting on the different pieces of feminine

clothing taken from her drawers. Nylons, a garterbelt, a matching bra

and a pair of panties soon covered his nakedness. Mary was no longer

interested in her stepson's nudity, this was more interesting. Double

shoulderpads were inserted in the cups of the bra and filled them out

nicely. This brought a smile to her face.

"Obviously, he done this before!", she silently giggled.

Meanwhile David had moved to his stepmother's dressing table. There he

proceeded to work magic with her make-up and a long haired wig he

produced from a bag he had carried in with him. Earrings, jewelry,

perfume, false eyelashes and false nails soon followed.

Mary, watched in stunned silence, as David rose, walked to her closet,

selected her new black crepe and chiffon dinner dress and stepped into

it. Her best black leather 3" high heels soon followed. Expecting him

to have trouble with the heels, she was again pleasantly amazed at the

ease and grace he showed as he walked across the bedroom to the full

length mirror next to her dresser. By now, David had transformed

himself into a perfectly lovely young woman. If Mary hadn't seen the

change herself, she wouldn't have had a clue as to David's true gender.

Mary decided to wait a little longer before she stepped out to

challenge him. She hadn't reached a decision as to how to handle the

situation. She hoped he would say something to help her better

understand his actions. She was somewhat confused, but also thoroughly

amused. Her stepson was a crossdresser and a good one at that! She

had heard of them, but had never quite understood the whys or the

reasons. Was he gay? Did he crossdress to entice boys or men? Or was

there some other reason? The next few sentences helped dispel the gay

concern. An even bigger surprise came when he began to speak. The

voice was perfect, just like the rest of him..

"I wish Mary could see me now!", he said. "Maybe if she saw me this

way she'd realize how much I want to be her daughter ... instead of

her stepson! Wouldn't it be wonderful if she accepted me! I could

dress this way every day! We could share all the wonderful things a

mother and daughter do together. She could help me much more than the

girls. It's fun to be Darla for them, but it would be so much better

if Mary could accept me as her daughter. Besides, I know the girls are

losing interest in my gender transformation. They're more interested

in boys and going out on dates, while I'm only interested in being

Mary's daughter."

That was all Mary had to hear. Her stepson wasn't gay! She was

however, shocked to hear him admit his girlfriends knew about his

gender switching and that they had helped him with it. She realized he

must have received help from someone. He couldn't have become so adept

at "passing" if some female(s) hadn't taught him not only how to dress,

but also the nuances of being feminine. The important thing, as far as

she was concerned ... he desired women ... he wasn't gay. The relief

she felt almost caused her to sigh aloud, thereby exposing her

presence. Her mind raced. David wanted to be her daughter! It was

more than just the desire to wear women's clothing. There was no

question he was more than adequate at crossdressing. The more she

stared, the easier it became to believe there was a young woman

standing in her bedroom and wearing her clothes. A beautiful one at

that! Mary had always wanted a daughter, this just might be the

chance. Besides if it didn't work, they could move away and start all

over again, nobody the wiser. If that's what her stepson truly wanted,

she decided, it was her responsibility to help him in any way that she

could. Her course of action decided upon, she stepped into the room

and said.

"Darla, you look wonderful in my new dress! In fact, I think you

should keep it. It looks nicer on you than on me. I'm so glad I have

a lovely young daughter who can wear such attractive clothes. You

remind me of myself at your age. I think you could use a little help

with your make-up, but I'll be more than willing to show you! Why

don't we go downstairs, fix ourselves something to drink and talk about

your desire to become my daughter. There's so much we need to discuss.

If your going to become my full-time daughter, then we will need to

change our entire lifestyle. Before we do, however, I'd like a hug and

kiss from my pretty girl!"

David had heard the sound of his stepmother entering the room even

before she spoke. Whipping around in fear, the chiffon skirt

"twirling" out from his nyloned knees, he was preparing to offer an

explanation, even though he knew it was fruitless. When he realized

what his stepmother was saying, he couldn't believe his fortune. She

was accepting him as Darla! This was really happening just as he had

dreamed it might. Rushing to her open arms, he threw himself into

them, hugging her tightly. Cheek to cheek, they whispered words of

love, understanding and gratitude. As David became more and more

convinced of Mary's acceptance, he began to cry. Tears of joy ran down

his face. When he was finally able to speak, he stated?

"Your the best mother a girl could have!"

Then realizing what he had just said, he began to giggle.

"Oh mom, you don't know how much this means to me! I don't really like

being a boy. I remember even when I was younger thinking how wonderful

it would have been to be born a female so I could grow up to look just

like you! Maybe that's why it took so long for me to start puberty.

Maybe I wasn't supposed to be a boy. I don't really know! What I do

know is the only time I feel good about myself is when I'm Darla."

Darla's new-mom spoke, "Honey, you might be right. Maybe you should

have been born a girl. With my help, maybe we can fix that. We'll

look into getting your identity legally changed when you get older.

From what I understand, it's not that uncommon or that difficult.

We'll worry about that later. Right now, I want to hear the whole

story. I want you to explain how you know so much about wearing

women's clothes and don't you dare leave anything out. I want the

whole story, everything about your crossdressing. How you got started,

grew into and all about these girlfriends who helped you."

David explained in detail. He revealed how he started with his

crossdressing, how he had progressed and how he had been discovered one

day wearing pink lace panties by the girls. This brought gales of

laughter from Mary and also David.

"I can just imagine that sight. You're face must've been at least the

color of your panties. What happened next?" she asked.

David continued his story, explaining what the girls had offered him,

how he had accepted and how they had helped him grow into the role.

Then, when he had become proficient at passing, they had taken him to a

Teen Club dance. Deciding to admit everything, he told her about "The

Kiss", his being asked to dance and how much he had enjoyed the

attention. David revealed how he had flirted with the boys and the

numerous requests for his phone number.

Mary interrupted, asking the obvious questions, received the answers

she hoped, and then Darla continued. She explained how the girls took

their Darla on shopping trips to the mall and the fun they had fooling

the various saleswomen as they tried on dresses, skirts, slips, blouses

and shoes. Once, Darla explained, she accepted assistance from a woman

who David knew was Mary's favorite salesgirl. The woman never

suspected a thing. Mary giggled as she imagined the scene. David

continued. Pajama parties, he explained, were the most fun. The girls

would introduce Darla to their parents and "she" fooled them every

time. None of the parents ever caught on. He got to wear their

nighties, had his hair put up in rollers and wrestled around the beds

together, all with the permission of the parents. Then when they

finally went to sleep, the girls would fight to see who would lie next

to him. He was surrounded by semi-nude teen-age girls, who would

"snake" their hands inside his silken panties and play with his penis!

Of course, he would use his hands inside their panties at the same

time. In explaining the rest of his story, he skipped around a bit,

revealing incidents about the other games the girls played and the

fondling they performed between themselves as he watched.

Then David went into his desires. He told Mary how he had come to

believe he had been born in the wrong gender. He wanted to grow up a

woman. He knew that's what he should be! He said he realized this the

day he saw her naked. When he started to explain his hiding under her

bed and how excited he had become, Mary let him finish. Then she

admitted she had known he was under the bed. She also admitted her

teasing games. David was stunned!

He asked, "Mom, why did you let me peek at you?"

"Honey, all those years, without a man around, made me feel less than

desirable. When you started to sneak peeks up my skirt and down my

blouse it made me feel attractive. I liked feeling that way and

decided as long as it was only the two of us ... what could it hurt?

All woman tease. Don't you think we know when a man is staring up our

skirts? We certainly wouldn't wear the clothes we do if we didn't want

men to stare at us. Real women enjoy the power we get when we casually

expose our bodies. Think about it. We women can't bend over without

our breasts being partially seen and how about our short skirts. Think

about how tight we wear our clothes ... so every curve is outlined for

men to fantasize over. Everytime we sit, we "show" at least our thighs

and usually more than that. Do you think we cross our legs just to

cover up? No, we do it to give men another chance to see! In this

male dominated society it's one of the ways women have of controlling

men. Now some women are too shy to admit it, but we do it to attract

the attention of the men and get them to do what we want. When I saw

the bulges in your pants I decided to have some fun with you, not to

have power over you, just to see how you were maturing."

Now that they had been honest with each other, their relationship had

changed. It wasn't as much stepmother to stepson, but one of equals.

Mary suggested they freshen their drinks, return to the couch and talk

about David's desire to become Mary's daughter. They spent the next

two hours covering the topic.

Mary admitted how much she had always wanted a daughter. While she had

always loved her stepson, she explained, she had felt "cheated" that

she would never have a daughter to share and teach the joys of being

feminine. Darla would be the answer to her prayers. "Oh, how I look

forward to these changes!" she announced a number of times as they

talked.

Numerous issues were left to be decided at a later date. The things

they needed to resolve immediately ... they did. They decided that

David would have to tell the girls his stepmother had discovered his

crossdressing, forced him to explain, forced him to expose their

involvement and forced him to break off his relationship with them. He

was told to explain to the girls that his stepmother had also found the

pictures. If the girls didn't want Mary to call their parents, they

were to forget it ever happened. David was certain they would accept

the terms and while he hated to threaten them (and lie to them), he

understood the need.

Since Mary was not tied to a job, she decided she would sell their

house and would move to another city. There, David would become Darla,

Mary's daughter, on a full-time basis. They'd investigate legally

changing the gender statement on his birth certificate and possibly a

partial sex change operation (breast implants), after they moved and he

became of legal age. Mary planned to take Darla, to her own

gynaecologist as soon as possible. The doctor had been her friend

since high school and Mary was sure she would help. She hoped her

friend would prescribe female hormones. These she explained would help

David's skin grow softer and minimize facial and chest hair. They

might even make his hips wider and his breasts larger and more

sensitive. Since he had been so late in reaching puberty, he might

still be able to change his frame. If nothing else the doctor could

give them direction. Plans were discussed for them to drive over to

Indianapolis that weekend and go clothes shopping. They could act as

any other mother and daughter and nobody would be the wiser.

Mary also informed David that her regular hairdresser had once told her

a story where she had done a female impersonators hair. Mary felt the

woman would do David's hair in a feminine style if the price was right.

The woman offered cosmetic assistance training and so they planned to

avail themselves of her skills. Mary suggested a trip to the local

medical supply store to purchase prosthetic breast sacks. These would

give Darla the realistic look, feel and weight of a woman's breasts.

They would also "move" more naturally under Darla's clothing. Various

other topics were discussed, decided upon or cataloged for future

discussion.

Finally, both mother and new-found daughter began to show signs of

exhaustion and decided to call it a day. After both had removed their

make-up, Mary ran a tub, not for herself, but for Darla. As the water

began to flow she added bath oil beads.

David was aglow as he stepped into the deliciously warm, scented water

of his first "female" bath. While in the tub, Mary had him shave the

"peach-fuzz" from his legs and also his underarms. When the water

began to lose it's warmth she handed him a towel and instructed him in

the manner of patting himself dry.

Mary presented her new daughter a white satin nighty with spaghetti

straps to sleep in. Then kissing Darla goodnight she said.

"This has been quite an exciting day for the both of us. Beginning

tomorrow we'll be able to share all the wonderful feelings of being

female and being mother and daughter. Now get some rest, there's

always tomorrow!"

Mary and Scarlet O'Hara were both right ... there was always tomorrow,

but that's another story.

(c) 1996 Kresha Matay