Caught Crossdressing by Aunt Sharon Story by Kresha Matay
"I wonder where Brad is? He knows you're coming, you'd think he'd stick
around. Oh, I hope he'll turn up soon, otherwise you'll have to drive
back in the dark."
"Rita, don't worry about the boy so much. Brad is like every other
sixteen year old boy. He's probably driving around with his friends
looking for girls and forgot I was coming!"
"Well, aah, I don't think so!" His mother stumbled to say. "That's
something you and I should probably talk about before you leave. Your
nephew is somewhat different from what you might expect from the
average sixteen year old boy. Sharon, you haven't seen him in over a
year, he's changed. He doesn't spend much time with the other boys in
the area, he seems to be more a loner."
Rita and Sharon were sisters. Rita, Brad's mother was thirty-five,
married to Tom and lived the unsatisfied existence of the average house
wife. She had been a lovely girl in her youth, attracting quite a bit
of attention from all the boys. In her senior year, she fell in love
with Tom Hennesey, the high-school football team's star quarter back.
After the victory dance, convinced that Tom also loved her, she agreed
to go to a local motel with him. Tom, typical of most boys that age,
had been neither gentle, nor concerned with her needs, only interested
in his own satisfaction.
She'd lost her "maidenhead", suffered considerable pain, was not
sexually satisfied, and needless to say was confused by Tom's
selfishness. Even worse, she became pregnant with Brad. Tom and Rita
discussed their alternatives, agreed to marry and with the help of both
sets of parents, set up housekeeping. Over the years, all her dreams of
the good life went out the window. With nothing to look forward to,
Rita eventually slipped into a casual attitude towards her appearance.
She gained thirty pounds, wore less attractive clothes and became
exactly what she looked like...an average mother/housewife.
Rita was secretly jealous of her sister Sharon. Not because Sharon was
younger by seven years, but because her life was more interesting and
exciting. Sharon was the real beauty of the two sisters. She had
enjoyed the attention her looks brought her, but was wise enough not to
get trapped as Rita had done. Boys, and later men, never became so
important in her life that she sacrificed any of her goals for them.
Sharon was 5'9" tall, perfectly proportioned (possibly a bit too large
in the chest), with long dark hair. Her features where chiseled in the
classic mold of a young Liz Taylor. Every man or woman she met was
immediately struck by desire or jealousy...sometimes both.
Sharon had started working at a bank right after graduating college in
a management training program. This meant she started out as a low-paid
teller and if she did well she would move up the ladder. It was the
typical way banks were able to get college educated women to work for
them at low salary levels. Her work performance and beauty got her
noticed by the President of the bank, who made her his administrative
assistant.
After the first month in the new position, her boss came to her and
asked her out to dinner, supposedly to discuss her performance. For the
next twelve weeks he courted her lavishly, showering her with gifts,
then asking for her hand in marriage. Sharon thought long and hard
before reaching a decision. He was a nice enough man and offered her
the opportunity of a wealthy lifestyle. Even though he was thirty-five
years her senior, she felt that was of little consequence. Sharon was
worldly enough to understand why he wanted to marry her. She didn't
love him and they both knew it.
Therefore, when he promised to be less than demanding...sexually, she
was tempted to say yes, but she still hesitated. What finally convinced
her to marry him was his offer of a pre-nuptial agreement. The
agreement guaranteed her a large settlement, after seven years of
marriage...or his death, whichever came first. For three years her life
was a whirlwind of parties, expensive clothes, cars and travel. As far
as intimacy, he kept his promise. Sex to her husband was the typical
"slam, bam, thank you ma'am, once a month event".
This was more to reassure his aging male ego, than for any other
reason. She "suffered" through those nights bolstered by the knowledge
that the marriage would end in seven years and she would be set for
life. When she was notified of the commuter plane crash and his
confirmed death, she shed not a tear. The fact that she inherited
everything "helped" console her and when an out-of-state bank offered
her a huge price for her controlling bank shares, she found she was now
a twenty-five year old widow with more money than she had ever dreamed
possible.
Sharon had offered a large piece of the inheritance to her sister, but
Rita's husband had refused to accept any of the "blood money". This
refusal caused an uncomfortable split between Sharon and her brother-
in-law. She only visited when she was sure Tom was away on business.
Rita in order to keep peace couldn't even call her sister since Tom
checked the long-distance phone bills. This didn't stop Sharon from
calling and keeping in touch with Rita and Brad. Whenever she did
visit, she would insist on taking both of them shopping and then out to
dinner at the most expensive restaurants and stores. This was her way
of making up for not being there on a regular basis. Brad, of course,
loved when his Aunt came to visit, what young boy wouldn't. As he grew
older he began to realize that she never visited when his father was
around. This hurt him deeply. His Aunt was the person he loved the
most.
Tom, Rita and Brad didn't have a peaceful homelife. Father and son felt
no warmth towards each other. Brad had not inherited his father's
physical prowess and was a definite disappointment to Tom. This
worsened the home situation even more, to the point that Brad began to
"hate" his father and Tom, in response, further ignored his son. Rita
was confused by her love for her son versus her love for Tom. This sent
mixed signals to Brad. Because he received no emotional satisfaction at
home, Brad replaced a child's normal affection for his parents with
affection for his Aunt and wished he lived with her.
He turned this desire to live with her into a fantasy in which he was
her son instead of Rita's. As many young boys do, he began to use her
image in his sexual fantasies. After his first fantasy, in which she
seduced him, he was hit with guilt induced tears and promised himself
he would never again view his Aunt as a sex object. However, the next
time he got the urge to masturbate, Aunt Sharon again appeared as the
sensual woman in his fantasy. With each fantasy re-enactment his guilt
lessened.
Tom felt that Brad was the reason he had been "trapped" into marrying
Rita. Oh, he assumed he loved his wife, but still wished they had
waited to marry till he had sown a few "wild oats". Besides, Rita no
longer looked like the woman he had married and no longer excited him.
More and more, he found himself thinking of having an affair with a
secretary where he worked. These frustrations manifest themselves in
the form of mental and physical abuse towards Brad, who sought refuge
in his confused mother's arms. This strained situation continued till
one day Brad, in a fit of anger, shouted at his father.
"I wish I could go and live with Aunt Sharon so I could get away from
you!"
His father was just as quick to answer, "If she'll take you, you can
leave right now!"
Rita, realizing where this was heading, stepped between father and son
and quickly suggested Brad "visit" his Aunt for the entire summer. Then
when summer was over, everyone would sit down and talk the situation
through and come to a resolution. She hoped that this cooling off
period would bring about a reconciliation.
That's why Sharon had come, to take Brad back to Columbus to live with
her. Rita was also concerned by changes she noticed in her son's
behavior. At first, she suspected what every parent fears...drugs. But
after reading about the symptoms and realizing they weren't present in
Brad's behavior patterns, she accepted Brad's behavior as the outward
effects of puberty. Rita had caught her son looking up her skirt, down
her blouse and peeking through the bedroom keyhole. While this made her
uncomfortable and she criticized his actions, she secretly enjoyed
knowing he found his mother attractive enough to spy upon. Brad's
spying made her feel wanted, now that her relationship with her husband
had soured. In addition, Brad showed interest in feminine clothing,
especially women's undergarments (he used his mother's panties to bring
himself to orgasm). She discovered unexplained runs in her pantyhose
and misplaced articles of her lingerie. While she didn't understand all
the actions, some were easily explained by the fact he was "growing
up".
One day, left alone in the house he decided, "If the panties feel so
good against my dick, I wonder how they'd feel if I wear them?" This
was his first step into crossdressing, but only the first. From that
moment, whenever he was alone, he would sneak into his mother's room,
carefully open her lingerie drawers and borrow a bra, panties and hose.
His mother never kept her drawers neat, so she never discovered his
temporary thefts. He continued dressing up in the borrowed feminine
clothing, experimenting and actually becoming relatively adept at
wearing his mother's attire. He also practiced feminine mannerisms in
front of a full-length mirror. When dressed and standing before the
mirror he created fantasy conversations speaking in a girlish voice
which he managed to develop with practice.
Once tempted, his young mind became obsessed with women, their clothes
and their bodies. He became an expert on lingerie and foundation
garments. He discovered the purpose each item fulfilled towards
enhancing a woman's figure. Matching his mother's lingerie labels
against the descriptions in the catalogs he learned to distinguish the
subtle differences of each material. Using this same method, he studied
dresses, skirts and blouses. Diligently applying himself, he soon
became expert enough to determine what a woman was wearing and the
material from which it was made.
Hearing a noise, both women looked up as the front door opened and Brad
walked in. Seeing his beloved Aunt, he rushed to her and leaned over to
give her a hug and kiss. In his excitement to see her, he lost his
balance and fell across her lap, his right hand falling between her
nylon clad thighs. Sharon's instinctive reaction was to close her legs,
thereby trapping his hand against the firm flesh of her upper thighs.
The absurdity of the situation became immediately apparent and the
women began to roar in uncontrollable laughter. This gave Brad the
opportunity to extricate his hand and right himself. Embarrassed, he
offered profuse apologies to both women, but especially his Aunt.
"It's alright Brad," she stated. "I know it was just an accident, it's
better it happened here, instead of in the presence of strangers.
Besides, it's been a long time since I've had that much fun with such
an aggressive young man," she teased.
Brad was embarrassed. Not knowing what to say, he stood there trying to
hide the blush plastered across his features and the erection in his
pants. Rita, seeing the bulge in her son's pants, realized her son's
predicament. Catching her sister's attention, she silently communicated
the situation, as all grown women are able to do. Sharon understood
immediately.
Rising, she threw her arms around Brad and whispered, "I'm only
kidding, don't be embarrassed, nothing serious happened and no damage
was done. After all, I'm your Aunt. If you're going to live with me
this summer we'll probably have other accidents around the house. Don't
let what happened embarrass you. It doesn't bother me, so don't let it
bother you. Now give me a big kiss to make it all better."
Brad kissed his Aunt and asked, "Am I really going to live with you all
summer?"
"Of course, it's all decided. In fact, since I have a dental
appointment tomorrow, we're driving back right after lunch. That way
we'll have time to get you all settled in. Are you packed?"
Rita started laughing, "He's been packed for two days, you'd think he
'hated' being with his mother", she chided.
"Oh mom! It's not you, I'll miss you, it's just...well you know."
"Yes dear, I know. Don't worry I understand. Now let's have that lunch,
so you two can get going."
After lunch they loaded the car, said good-bye to Rita and headed out
of Chicago. Aunt Sharon explained that the drive normally took seven
hours, but they would stop for a break in Indianapolis.
Sharon spent the next hour or so asking questions of her nephew. At
first he was evasive, not wishing to disclose anything about the
situation at home, but as he became more comfortable with his Aunt, he
opened up to her. She learned about Tom's abuse and Brad's closeness
with her sister. She discovered that Brad, within the last 18 months,
had also discovered the female gender. Unfortunately for Brad, it had
arrived, just as his relationship with his father had worsened.
After an hour of driving, Sharon turned south on I-65 towards
Indianapolis. This stretch of road is considered one of the most boring
in the mid-west. Flat farm land as far as the eye can see, the exit
signs being the only breaks in the monotony. Traffic was extremely
light so she settled back, in the most relaxed and comfortable position
available and set the cruise control to the speed limit. Her body
adjustments caused her 18" skirt to rise above the welt of her nylons.
She could have easily tugged the hem back in place, but instead, chosed
to ignore it. This was the manner in which she normally drove and
decided she wouldn't change her entire lifestyle because of Brad.
Sharon said to herself, "He's only a teenager and probably thinks of me
as a second mother. In fact, I'll suggest that he views me in that
light. If that works, It'll mean fewer changes in my lifestyle."
Glancing over at her nephew to determine the effect of her exposure,
she found him curled up...asleep. Smiling to herself, she returned her
attention to the road.
Brad wasn't really asleep. He had chosen to avoid further questions by
playing "possum". Peering between his drawn eyelashes he became aware
of his Aunt's exposed thighs. Mumbling softly, as if asleep, he
adjusted his position in order to obtain a better view and at the same
time, moved his hands in order to cover his crotch.
Sharon, hearing him moan, again glanced over at Brad, then smiled down
at him as a thought ran through her mind. "I hope it works out between
us, I think I'd like Brad to live with me on a permanent basis. I've
always wanted my own child. I would've preferred a daughter, and I wish
he were younger, someone I could better relate to, but having a son
like Brad would be wonderful. Of course I'm going to have to make some
adjustments in my lifestyle...especially Sandy."
She smiled to herself as thoughts of Sandy, her lesbian lover came to
mind. After her husband had died, Sharon found she felt no need to
become romantically involved with another male. Unfortunately, her
sexual needs still existed. She and her roommate, during their college
years, had played "girl games" in the secrecy of their apartment and
had "discovered" each other. Though, she never spoke about those "old"
days, she had enjoyed the sexual experimentation and tender
satisfaction they had shared. Sharon, remembering those blissful
moments decided it was time to try the gentler sex again. After a few
embarrassingly un-successful and pathetic attempts, she resigned
herself to masturbation. That's when Sandy came into her life.
Sandy was the bank examiner involved in the audit when Sharon sold her
bank shares. The two women immediately saw something in the other's
eyes, had lunch together, admitted they were strongly attracted to each
other and became lovers. Within a short span of time, Sharon had
invited Sandy to move in with her and Sandy agreed. Sandy's job caused
her to be away for extended periods. Whenever she was in town, she
spent every available moment with Sharon. Sharon's realized how much
she missed the "bitchy" blond who shared her bed.
Sandy's current absence, over three weeks, caused sexual desire to
creep into her thoughts. She soon realized, that thinking about Sandy
was causing her pussy to become damp with desire. Slipping her left
hand to her inner thigh, she gently stroked the warm flesh above the
welt of her nylons. Stretching her long nailed index finger under her
drawn-up skirt, she found the tip of her nail was barely short of her
panty cover crotch. Adjusting her hand an inch closer made all the
difference in the world. Now she could "tease" the silky smooth
material holding back the puffy entrance to her womanhood.
Drawing her nail slowly upward caused the tightly drawn nylon panty
material to sensually vibrate against her moist opening. Enjoying the
ever increasing exhilaration that came with each finger-stroke caused
her to softly "mew". Still not fully satisfied with her position,
Sharon thrust her hips forward. Now the nail tip located the demanding
bud of her blood-filled clitoris as it pushed against the now soaked
crotch of her panties. Back and forth, slowly, moving only the last
digit on her finger, she flicked the now protruding mound of flesh,
fantasizing it was Sandy tongue instead of her own finger. Building her
passions to the impending brink of orgasm, she paused, remembering
where she was and who sat next to her.
Realization was a bucket of cold water. There was no doubt that her
impending climax would wake Brad. Disappointed, but also adult about
the situation, Sharon chosed the respectable course. Giving herself a
last firm flick, she forced her hand away, hiding her actions by an
adjustment of her skirt. With a last look at Brad, to reassure herself
that he was still asleep, Sharon returned her mind and eyes to the
road.
Brad, had seen everything! Disappointed and ecstatic at the same time.
He could now add a touch of sensual realism to his fantasies.
Remembering what he had just witnessed, he really fell asleep, dreaming
of future voyeur episodes he might experience while living with his
Aunt.
The rest of the trip was uneventful. They stopped in Indy, had a snack
and continued their journey. They arrived in Columbus, shortly after
sunset.
Sharon gave him the grand tour of her home. Brad was truly impressed.
While it wasn't quite a mansion, it was the largest and most luxurious
house he had ever been inside. When she showed him her master bedroom,
he became sexually excited. It was so ultra-feminine, with its frilly
curtains, lace bedspread and pastel walls and lamps. The room was
dominated by the large "four poster" king-size bed with it's sheer
drapes tied back at the corners. The pictures on the walls were
definitely well suited to the color scheme, if not a bit strange to his
youthful mind. They depicted beautiful naked women, alone or in pairs,
sensually reclining upon couches and beds. The women's genitals
scarcely hidden by a crossed arm, raised thigh or perfectly placed
pillow. Brad was tantalized by the suggestive nature of the paintings
and made a mental note to sneak back into his Aunt's room to further
study the prints.
Hiding his erection, he asked, "Where will I sleep?"
"You can have your choice," his Aunt answered. "There are two other
bedrooms to choose from. Actually there are three, but the one next to
mine is used by a friend who visits me whenever she's in town. She
keeps some clothes here and rather than move her things, I'm sure
you'll be satisfied with one of the other two. Let me show you."
After being shown both rooms, Brad picked the more feminine of the two.
When his Aunt pointed out he might be more relaxed in the other since
it was "neutral", he stated he particularly liked the feminine bedroom
because its attached bath room contained a spa type bathtub. He
explained he preferred baths over showers. This explanation more than
satisfied his Aunt, who then recommended a possible redecorating. Again
he assured her it was fine.
"It doesn't bother me, let's not change it until we find out how long
I'll be staying with you."
"Well, if that's all settled do you want me to help you unpack?" she
asked.
"No thanks, Auntie, I can manage. Besides you must be tired from the
long drive, why don't you relax and I'll join you after I'm finished
putting away all my stuff."
Sharon admitted she was tired, wanted to change into more relaxing
clothes and would see him downstairs in the den when he finished
unpacking.
Before leaving she said, "Brad, I'm very happy you're here and I'm sure
we'll get along very well. However, I want you to understand that it's
been a long time since I've lived with anyone, so I've come to like
things a certain way. I'll expect you to respect and comply with my
wishes as if they were your mother's. In a sense, during your visit, it
might even be better if you think of me that way. You'll have some
chores just like at home, nothing difficult. This is a very large
house, but since I like my privacy, no servants. I have a cleaning lady
twice a week who handles the 'big' stuff, but picking up after
yourself, etc., is your responsibility. We'll talk more about that in
the morning. Now if you don't have any questions, I'm going to clean up
a bit and go relax. Any questions?"
Brad assured her he would do anything to please her, wouldn't be a
bother and thanked her for taking him in for the summer. Throwing his
arms around her, in a surprise move, he hugged and kissed her. The kiss
was just a hint longer than Sharon expected and the hug was also more
familiar. After a few more "thank-you" and "you're welcome"
comments...Sharon left the room.
Brad spent the better portion of an hour unpacking. He had declined his
Aunt's help because he didn't want her to see some of the items in his
suitcases. Along with his normal clothing, he had a cache of feminine
"pretties". These included panties, a bra, a garterbelt and a pair of
nylon hose. He had to find secure hiding places that would not be
discovered by either his Aunt or the cleaning lady. Finally, he decided
to leave them in his supposedly empty suitcase which he stored in the
back corner of his walk-in closet. Satisfied, he removed his clothes,
changed into a pair of blue cotton pajamas and went down stairs to find
his Aunt.
Meanwhile, Sharon had also changed into a pair of pajamas. Hers however
were white satin lounging pajamas with baby pink and blue designs at
the collar and cuffs. Normally, in the evening, she wore diaphanous
peignoir sets around the house, but chosed the pajamas since her nephew
was there. Realizing, with regret, that changes were indeed necessary,
she again hoped they could be minimized.
Sharon was a woman who enjoyed being feminine. All her lingerie was the
finest, most expensive available. Oh, it wasn't all that exotic... just
sensual. One of her pleasures in life was the freedom to express her
sensuality in the privacy of her home. One of the great joys of her
existence was the thrill of being feminine. The only disappointment of
her sensualness was she couldn't let anyone other than her lesbian
lover know how much pleasure she derived from secretly expressing her
femininity through her lingerie.
As Brad entered the den, Sharon said, "I thought you might be hungry so
I've prepared a lite snack. It's just cheese, pat'e and some crackers.
If you don't care for pat'e we can order a pizza or something."
"Pat'e sounds wonderful! I am a little hungry and that will just hit
the spot. I like pat'e. Mom introduced me to it two Christmas's ago
when you sent that gourmet basket."
Brad moved to the couch and sat next to Sharon. They spent the evening
enjoying the snack and each other's company. Every now and then, as
Sharon reached for a morsel of food, Brad caught a glimpse down the
throat of her satin pajamas. He couldn't see much, just the beginning
rise of his Aunt's right breast. He tried to be careful, but thought
she caught him staring at least once. Since she said nothing, he wasn't
sure. Sitting there, next to an adult woman (the woman his fantasies
were built around), in her sexy pajamas, smelling her perfume and
observing the raised "pock" marks her nipples made on the material was
more than he could handle. Thinking about what was barely hidden behind
the material got him excited. Brad developed an erection! Trying his
best to adjust the folds of his pajamas, he dropped a cracker into his
lap.
Sharon had definitely caught him staring down her pajama top. Realizing
he couldn't have seen anything, she excused it as boyish curiosity and
made no effort to adjust her clothing. When she caught him staring at
the nipple marks however, she decided that he needed to be taught a
lesson. When he attempted to adjust his clothing, she realized he was
sporting an erection. Amused, surprised and curious, she watched as the
cracker fell onto his lap. Acting quickly, she reached her hand into
his lap as if to pick up the cracker before it fell to the carpet.
Instead of the cracker her hand encircled his maleness. It was much
bigger than she had expected. Just as she prepared to release Brad and
sternly criticize him for his "pee king" ...he moved.
Brad was caught by surprise...to say the least! When his Aunt's hand
grasped his dick, he pushed his shoulders back against the couch, his
heels into the carpet and his hips up off the seat. This, instead of
helping the situation, made it more embarrassing. His Aunt's hand
reacted, holding him tighter! His pajamas outlined his hard-on so that
neither he nor his Aunt could make-believe it didn't exist. Not knowing
what to do, he froze. Searching his Aunt's features for a hint of
direction, his mind raced. "How could I be so stupid! Aunt Sharon must
realize I was peeking at her tits. She'll probably send me back home
and tell mom. I'll be grounded for life!
Before he could apologize, she released him, then spoke, "Well, I think
we'd better talk! I want you to tell me what you were doing to cause
that erection. We can't have you in a constant state of arousal just
because you're living with me. I'm not going to dress like a nun, just
because you're here. I expect you to tell me everything young man, and
it better be the truth! What have you got to say for yourself?"
With his head down, Brad began. He explained he had really been awake
and had observed Sharon "playing" with herself in the car. He stated it
was the first time he had seen a woman tease herself and he not only
became excited but also came to realized his Aunt was more than just
his Aunt, she was a very sensual woman. Now, he admitted, he was
sexually turned on by her. Next he told Sharon how he had stolen looks
down the top of her pajamas and while he hadn't really seen anything,
just knowing what was there, caused his dick to become semi-erect.
Then, when she had leaned back and he saw where her nipples were
pushing against the material, he had lost control. His dick became rock
hard as his mind visualized the pouting nipples hidden behind the
material of her pajama top!
After admitting all, he said, "Aunt Sharon, I'm really sorry! I didn't
mean for this to happen, it just did. I can't help thinking about women
and their bodies...and yours especially. Your the prettiest and most
sexy woman I know! I love you! Please try to understand, I can't be the
only boy or man that has stared at you, you're so absolutely beautiful,
men must stare at you constantly. Even before I came to live with you,
I would fall asleep and dream you were my girlfriend. Whenever you
visited I would be in seventh heaven. I love the way you look and smell
and especially how you hug me. I know I shouldn't get sexually excited
when I'm near you because you're my Aunt, but sometimes I just can't
help myself. If you let me stay, I promise to control my feelings and I
won't try to 'peek' at you. I love you, even more than mom. Please give
me another chance?"
Sharon didn't know what to say or do. Her plan had been to embarrass
her nephew and maybe even punish him for his actions. After hearing his
reasons, she realized she was also at fault. If she hadn't exposed
herself in the car and "played" with herself, maybe he wouldn't have
changed his perception of her. It was obvious, he had a "crush" on her.
On top of everything else, she liked it! Sharon realized her nephew was
in the throes of puberty and remembered how strong her own emotions had
been when she went through it. "He actually thinks I'm the prettiest
and sexiest woman in the world!" she mused. "I've got to do something,
I can't let this continue all summer, but what?"
Looking at Brad, she began, "Brad, what you saw in the car was wrong.
It wasn't wrong that I did it, it was wrong that I did it when you were
there! Women masturbate as much as men. We have sexual needs also. So,
for what you saw me do in the car, I apologize. But you had a
responsibility, as my nephew, to not look, or to 'wake-up'. Tonight,
you compounded the problem by your peeking at my breasts and by
thinking of me as a sex object. Women are not 'toys' for men to play
with or to use. I believe you're sorry and will try not to let this
happen again, but you must be punished. If you agree to a serious
spanking, I'll forget this incident and give you one more chance."
Brad interrupted, "Oh Aunt Sharon, if you give me another chance, I'll
take whatever punishment you think is fair!"
"Don't agree too quickly, this will be a serious spanking. I can't and
won't allow you to think of me, your Aunt, as a sex object. Also, I
want you to re member this spanking so that if you get tempted again...
you'll change your mind."
Lowering his head, he said, "Aunt Sharon, will you give me the spanking
I deserve?"
"Since you asked so nicely, yes. Now, go upstairs to my bedroom, take
off your pajama bottoms and wait for me."
Brad was stunned, he hadn't expected a "bare-bottom" spanking, but from
the look on his Aunt's face, he knew better than to protest. Realizing
he had no other option, he headed for his Aunt's bedroom.
Why Sharon had decided to administer a spanking she had no idea. It had
flowed out in the discussion and at the last moment, she realized that
the embarrassment of it being on his naked butt would go a long way
towards curbing his desires for her. She also decided to wait about ten
minutes to heighten his fear. Lighting a cigarette, she remembered the
spankings she had received as a child. The last one had been
administered by her mother at sixteen. Her mother had caught her
smoking behind the garage. She had enjoyed the spanking, even though it
was painful. Putting out the last of her cigarette, she went upstairs.
Entering her bedroom, she moved to her vanity and sat with her back to
the mirror. Not saying a word, nor looking anywhere other than at
Brad's face, she motioned him to place himself over her knees.
Brad had used his hands and the tail of his pajama top to cover himself
so his Aunt wouldn't see his crotch. Moving to her satin covered lap,
he positioned himself across it. His cock and balls falling into the
opening between her satin covered thighs. The shock of the first slap
was a surprise. His Aunt wasn't holding back, as he had hoped. With
each succeeding fall of her arm the pain increased, but he soon
realized, it was also exciting. To be spread across a sexy woman's
satin covered lap, with her in total control, made him momentarily
forget the pain. Now he felt his dick rubbing against her satin covered
thighs. Feeling his cock become hard he began to take pleasure in each
stroke, since her thighs moved in response to the swing of her arm.
Sharon had initially intended 10 slaps, 5 on each buttock. As each
stroke fell she realized she was enjoying herself. Then when she felt
his hardness between her thighs, she understood he was enjoying it
also. She knew she should stop...but her own sense of enjoyment
wouldn't allow it. It felt exciting to have her nephew under her total
control. She was now treating the youth as a sex object for her own
satisfaction. When her arm began to tire and she sensed his needs
rising, she stopped.
Reaching behind her, she grabbed the jar of Noxema from her vanity.
Unscrewing the lid, she inserted two fingers, scooped out a generous
amount and began to rub it into the flame-red skin of Brad's butt-
cheeks. Explaining to him that this would help "cool-down" the pain. It
would also give him enough time for his cock to shrink, thereby
eliminating her having to recognize the punishment hadn't worked.
Sharon had decided Brad would receive more spankings in the future and
didn't want him to realize she had noticed his enjoyment. When she no
longer felt the hardness between her thighs, she released him. He stood
before her, both hands massaging the cheeks of his ass, no longer
concerned about his nudity. Sharon, risking a look at his equipment was
impressed that one so young was so well endowed. When she asked him if
he had learned his lesson, she received his promise and then sent him
off to his room, but not before she took a final look at his cock.
After he left, she shut the light and brought back the memory of Brad's
spanking. With a smile on her lips, she fell soundly asleep.
Brad, left her room, not even bothering to put on his pajama bottoms.
The first thing he did upon entering his room was to stand before the
full-length mirror and examine his rosy-red ass. Touching the tender
skin, he said aloud, "Boy, when she gives a spanking, she's serious
about it!" Then thinking back on what had occurred, he smiled and said,
"It's a good thing Aunt Sharon never saw my hard-on, I can just imagine
what that would have cost me."
Deciding to try to sleep away the burning pain, he stretched out across
the bed. Not bothering to cover himself, he lay there going over the
exciting events of the day. The last thing he remembered, as he fell
asleep, was his hard-on rubbing between his Aunt's satin covered
thighs.
The next morning they both slept late. Sharon made them a quick brunch
and all was well again between the two, the events of the previous
night forgotten. Sharon, during the meal, explained his new duties
around the house and asked how his butt felt. After being assured that
the pain was mostly gone, she stated she had a few errands to run
before her dentist appointment. When she returned, she planned on
taking him shopping.
She explained, "I'm sure you didn't pack enough clothes in those two
suitcases, so let's get a late lunch and go to the mall and get you
some additional clothes to last through the summer."
Brad asked if he was to go with her on her errands? Aunt Sharon said
she usually had to sit and wait at the dentist's office, so if he
didn't mind being alone, she would come back and get him after she
finished at the dentist's. This suited him much better.
When she left, he went to his room and began collecting his feminine
attire. Then a thought came to him, "Why don't I take advantage of Aunt
Sharon's absence and do a bit of snooping. She said she wouldn't be
back for about three hours. If I don't find anything interesting I'll
still have time to change into Lynn (his alter ego)."
As he walked towards his Aunt's bedroom he passed the spare bedroom
where Sandy kept her stuff. Trying the door, he found it unlocked. He
decided to investigate that room first. If he disturbed something in
the friend's room, he rationalized, it was less likely to be noticed
and/or questioned. Opening the door, he discovered the room was almost
a duplicate of Aunt Sharon's, as feminine, just done in different
colors. Opening the door of the walk-in closet, he found the light
switch and flipped it on. It was not what he expected! The closet was
half-filled with dresses, skirts, blouses, etc. He had expected only a
few outfits, just enough for his Aunt's friend to get by on when she
visited. The woman could have lived here for a month or more with all
these clothes. Looking at some "built-in" shelves, he was again
pleasantly surprised. They held four or five different wigs, all in
different styles and shades and a collection of sweaters. The sweaters
were packed in clear plastic zipper bags. In addition, there must have
been twenty pairs of shoes, mostly high heels.
"This is going to be wonderful! I can dress-up and Auntie will never
realize it!"
Stripping to his shorts, he select a dress and held it up against his
body. It looked to be almost a perfect fit. Maybe a bit long, but heels
and my false breasts will raise the hem, he mused. Replacing the dress,
he selected one outfit after the other. Picturing himself in each, he
began to get excited over his new-found treasures. Where before he had
had a few outfits to change into, now he realized Lynn had, for all
intents her own complete wardrobe. Each succeeding outfit raised his
level of excitement. The different colors, designs, materials and the
variety were overwhelming.
"I wonder what lingerie Aunt Sharon's friend left here?" he said aloud.
Deciding to "see" what was available in the dresser, he carried the
dress with him and returned to the bedroom. There he lovingly placed it
upon the bed and moved to the dresser. Standing before it, he slid open
the top drawer. It was full of multi-colored bras and panties. He
immediately realized that the owner must not be concerned with
neatness. The contents had obviously just been tossed haphazardly into
the drawer and "pawed" through when she needed something to wear. No
matter how he left the "pretties", he would raise no suspicions.
"What a delightful situation!" he said aloud in his best Lynn voice.
Sliding open the next drawer, he found it contained slips and
nightgowns. This lingerie was of course much neater, but still not
necessarily sorted. Emptying the contents onto the top of the dresser,
one at a time, enabled him to study the items. The night gowns were
made of the sheerest and most diaphanous material he had ever seen.
"When this woman wears these she doesn't hide much," he thought aloud.
Unfolding a couple of items, he discovered the method the woman used to
fold both nightgowns and slips to be the same and simple to duplicate.
He knew he would have no trouble replacing everything just as he found
it. The third drawer was filled to the brim with nylons and pantyhose
in different shades and colors. These were again just stuffed in as
were the contents of the first drawer. The bottom drawer held a panty
girdle and various garter belts.
Moving to the three drawer vanity he found make-up, false eye-lashes,
brushes to apply cosmetics and in the second drawer, under some
socks... a vibrator. The bottom drawer held two book-like objects, both
covered in hand-tooled dark leather. The first was a locked diary. It
would take some careful work to get past the lock, but Brad knew he
would find a way. Maybe he could find the key to it hidden somewhere.
The idea of reading a unknown woman's inner thoughts was too strong to
resist. Opening the second book he found it was a photo album. It held
20 vinyl pages, each page able to hold two pictures on each side. It
was about half-full. The first page, an unknown woman (he supposed it
was his Aunt's friend), dressed in garterbelt and nylons, had her head
buried between the thighs of another woman dressed in the same manner.
The other woman's identity became clear in the next photo... It was his
Aunt!
Brad couldn't believe his eyes. Here was his naked Aunt, the same woman
who had spanked him for staring at her while fully dressed, involved in
lesbian sexplay. After the spanking, he had assumed his Aunt wasn't
interested in sex, now he knew better.
"Boy, was I wrong about her!"
Quickly turning the pages he found the two women displayed in various
sensual positions. He found scenes he had never even imagined. He could
see the look on Sharon's face was one of wanton desire. After rushing
from one picture to the next, he came to the last one. Having been in
such a state of excitement, he hadn't really had time to study each
shot, he decided to go through it a second time. Flipping to the front
page again, he now looked at each photo in detail. Both women were
obviously pretty and had gorgeous bodies. Not being able to "stand"
anymore, he rushed to the john, grabbed some tissues and after just a
few strokes, came in his hand. Cleaning himself up, he then returned to
his discoveries. Looking at the clock on the nightstand he decided
there was plenty of time to try some of the outfits before his Aunt
returned. Going from drawer to drawer he made his lingerie selections.
Removing his shorts, he began the change from the male Brad to his
other persona, the female Lynn.
Placing a black lace garterbelt around his waist, he slipped the hook
into the loop and spun it around. Then balling the sheer, black nylons,
he alternately inserted one foot after the other into the re-enforced
toes. Grasping the balled-up material at the toe of his right foot, he
"slinked" it up his out-stretched leg and attached it to the dangling
garters at his thigh. Repeating the process on his other leg. French-
cut white silk panties with bone colored lace and a matching under-wire
bra, each cup stuffed with two additional nylons, followed.
A red polyester full slip and black and white trimmed coat dress were
next. Within a relatively short time he was fully dressed as Lynn.
Returning to the closet, he selected a pair of black and white
spectators which matched the dress he had selected. Turning towards the
shelves, Lynn decided upon a shoulder-length, honey-blonde wig. Placing
it on her head, she moved to the vanity. Brushing the borrowed wig into
its pre-shaped shoulder flip until he was satisfied that it laid just
right. Deciding on which lipstick and eye-shadow took but a second or
two. A little blusher, to highlight his cheekbones and a pair of clip-
on earrings completed the transformation. Perfume was too dangerous, he
decided.
Peering into the mirror...Lynn felt very satisfied. She actually was
quite lovely. Her natural small features went a long way towards her
"passing." Standing, she raised her hem and re-adjusted each nylon.
Holding up the skirt portion of the dress to her waist she smiled... no
revealing bulge. Lynn had become quite adept at controlling her hard-on
whenever she wanted, last night being an exception. She had thought
about this ability. In the beginning, she got hard whenever she
crossdressed. Now, she no longer got overly excited by the gender
transformation. Lynn still desired crossdressing, but didn't get a
hard-on just because of it. She wondered if it was possible she
should've been born a girl... but wasn't sure if that was the answer.
"Oh, right now it doesn't matter. All that counts is I can change my
gender whenever I please. After I grow-up and go out on my own, I may
look into the possibility of a sex change operation, but for now, this
is enough. Now I think I want to take a walk through the house."
Loving the way the feminine clothing moved as she walked, Lynn left the
bedroom and proceeded to walk the hallway. Back and forth she swished
the entire length of the hall. The clothes and heels fit perfectly!
This was going to be heaven living with his Aunt! Deciding she was
thirsty, she turned, walked to the circular stair case and lightly
grasping the railing, she made her way downstairs copying the style she
had seen in an old Lorretta Young movie. Halfway down, she heard a
noise and the front door opened. Caught, she had nowhere to hide! In
walked Aunt Sharon. She saw Lynn immediately. A look of surprise,
followed by one of confusion, recognition and finally amused anger.
"What are you doing? You're wearing Sandy's dress. What's the meaning
of this? Come down here, right now!"
Brad always knew his secret would someday be discovered, but still
tried to stammer an explanation. His Aunt would have none of it.
"I said get down here, now! I guess the punishment you received last
night didn't leave much of an impression."
Brad meekly followed his Aunt into the den, where Sharon sat down on
the couch and motioned him to stand before her.
"Now young man and I obviously use that term loosely, explain
yourself."
Brad explained all the crossdressing details of the last eighteen
months as his Aunt listened in growing astonishment. Noticing the
bemused look on Sharon's face, Brad took heart. Maybe she wasn't as mad
as she projected? He continued the story of his feminization and
brought her up to this morning.
Sharon stopped him at this point in the narrative and said, "Let's go
up to your room where you will show me the female clothes you brought
along with you. That way I'll know if you're telling me the truth."
Brad led the way up the stairs and down the hall to his room. Sharon,
walking behind him, marveled at how well he mimicked the mannerism and
walk of a young woman in heels. She had to admit to herself, "If I
didn't know she was my nephew I'd swear she was my niece! Look at the
way she gently rolls her hips as she walks and she really has great
legs and a fine ass! Lots of young women would love to look that good
from the rear! Of course she doesn't look bad from the front, either.
She needs help with her tits, they're a bit off center and one is
slightly lower than the other. Plus her make-up needs work, but in
total, she's actually quite pretty. With my help, she could easily pass
as my niece." Then realizing what she had just said...Sharon began to
softly giggle.
Brad unpacked his suitcase and displayed all the female clothes he had
brought with him. When he saw the satisfied smile on her face he
thought he might get away with not having to explain his crossdressing
in Sandy's clothes, but that was not the case. Sharon, realizing the
look of hope his eyes projected and what the look implied, dashed his
hopes and demanded he continue his story. Detail after detail of this
morning's snooping was admitted. At the last moment he decided to hide
his discovery of the diary and the photo album. Maybe he could use them
to bargain with. His silence about Aunt Sharon being a lesbian had to
be worth something, he reasoned.
Finishing his story, he asked, "What are you going to do about me,
Auntie? Please keep my secret," he pleaded.
"I need some time to think this through. Let me understand this, you
would rather be a girl than a boy. It's obvious your adept at acting as
a female and I don't suppose anything I do or say will change your
desire to crossdress. Even if I expose your crossdressing to your
mother it certainly won't solve anything. All it will do is make my
sister's life more miserable because she'll have to tell your father
and we both know what his reaction will be. I'm not sure that I can do
that to her or you. Maybe you're right, maybe you should have been born
a female. Be that as it may, the question still remains, 'What do I do
about it and what do I tell your mother?'"
Brad had a solution, but, wasn't quite sure if his Aunt was ready to
hear it. Deciding to take a wait and see attitude, he shrugged his
shoulders as his only response. After all, he still had the photo album
as leverage.
Aunt Sharon continued, "Right now, I'm going to let you stay dressed as
a woman for the day. Obviously, we're not going shopping. If I'm going
to allow you this gender switching you may not need more boy clothes
and I'm not taking you shopping for female clothes, at least not just
yet. Also, I'm not ready to be seen with you dressed as a girl. I will
allow you to spend the entire day showing me how well you can pass. If
I'm satisfied you're that 'good' maybe we can both have some fun with
your desire to be a woman. It might be fun to have my niece visit me
for the summer instead of my nephew. That doesn't mean I'm going to
forget your snooping, or that you borrowed my girlfriend's clothes. But
we'll discuss that later. Now, what is it... Lynn, let's go downstairs
and have some lunch."
Over lunch Sharon explained that the dentist was called to the
emergency ward of the local hospital to assist the doctors. An accident
victim had been brought in whose face had hit the windshield and who
needed immediate dental attention. This caused the dentist to cancel
all his office appointments. When Sharon was informed of these events
by his nurse, she decided to return early and pick-up Brad.
Through-out the meal, Sharon carefully observed Lynn's movements, when
they went back to the den she told Brad she liked what she had seen so
far.
"I'm halfway to accepting you as Lynn. There are, of course, some
needed improvements in your appearance. We'll work on those this
afternoon, but before we get to that, we need to talk. Why don't you
sit here on the couch, next to me."
Lynn moved to join her Aunt on the couch. Placing her hands under her
skirt she gracefully sat down. Crossing her knees and placing her hands
in her lap, she turned towards her Aunt. It was obviously done to
Sharon's satisfaction, since she smiled at Lynn, then said, "If I agree
to your becoming Lynn on a full time basis, our relationship is going
to change. First of all, you'll have to become my niece to everyone
with whom we come in contact. You won't be able to switch back and
forth between genders. That would be confusing to both of us and too
dangerous! Since I haven't told anyone about your visit, I'll just
change the story a bit. Therefore my niece instead of my nephew will be
staying the summer. However, I'm going to expect a higher level of
obedience from you. Some of the things I might have excused from my
nephew, I won't from my niece. Brad, this is your big chance to take on
the lifestyle of a young woman over an extended period of time. It's
definitely your only chance to do so with the help I can offer you. I
am going way out on a limb for you and I expect absolute compliance
with my wishes. Any variance will be dealt with in a serious manner.
That's not to say you'll be harmed, but you will be punished, like last
night."
Brad quickly responded, with a mischievous sparkle in his eye, "Auntie,
help me to REALLY transform myself into a woman, make me your niece and
I promise the only time I'll need a spanking is when I want to be
placed over your knees."
"Aha! So you enjoyed last night, I thought so! Well, since you are
being so honest, I'll be just as honest. I enjoyed giving you that
spanking. I guess you may get more spankings than I anticipated. Are
there any other secrets you'd like to admit? If we're going to change
our lifestyle we need to be perfectly open with each other. You go
first and then I have something to tell you."
Brad surmised he knew what his Aunt was alluding to...her secret life
as a lesbian. He now had the perfect opening in which to admit what he
knew about her sexual preferences. Because of what had already
transpired, he had decided not to blackmail Aunt Sharon. Without
further hesitation, he told her about finding the diary and the photo
album. He told her he hadn't read the diary, but had seen the pictures.
Watching the reaction on Sharon's face change from shock to smiling
embarrassment was wonderful.
As I've said, Sharon's initial reaction was one of shock. She had been
about to admit her lesbian tendencies to Brad. She had realized that
when Sandy showed up next week, their secret would have been revealed
anyway. What shocked her was Brad seeing the pictures of their love-
play together and the acts they had performed which obviously exposed
their nakedness. Explaining to her nephew she was Bi-sexual was
certainly different than letting him see her in the act of eating
another woman's "pussy". Realizing there wasn't much he hadn't seen,
she asked. "What do you think of me, are you disgusted?"
"Oh no!" he stated. "I thought the pictures were beautiful. Beautiful
and very, very sensual. It made me wish I was the lucky woman in bed
with you. I think you're the sexiest woman alive. I would have given
anything to join you in those scenes. Auntie, I think I better explain
something. I'm not interested in males, even when I'm dressed as Lynn.
I'm not gay in that sense. I want to be a woman with other women."
Sharon said, "Brad, I think you better explain what you mean, I realize
you have a crush on me, but I'm confused."
"You wanted us to be honest with each other, well I can't be more
honest than I'm being now. Even before I saw those pictures I
fantasized about making love to you! You're the only woman I've dreamed
about going to bed with, sometimes as a boy being seduced by you and
other times as a young woman and your equal. I've pictured myself,
hiding under your long skirts, totally hidden from view, as you carried
on a conversation with another woman. What I would do to you would make
your legs shake and your voice crack. Other times I saw myself sitting
next to you, with your hand inside my blouse, teasing my tits, while
your other hand teased circles upon my nyloned thigh. You would un-
button your blouse and let me suck your breasts. There, I'm sorry if
I've offended you, but I finally had to tell you how I really feel. I'm
tired of hiding those feelings from you!"
Sharon was momentarily taken by surprise. Her mind raced as Brad
declared his love for her. The feelings Brad had for her were obviously
stronger than she at first realized. Sharon was not one who squandered
time when a quick decision was needed. Her decision made and without
explaining her decision to Brad, she acted upon it.
"Honey, let's take this discussion upstairs and get to work on
improving your feminine appearance."
The next few hours brought about a major change in young Brad's
appearance. He was told to strip, whereupon his legs were shaved for
the first time, his pubic hair was trimmed and shaped and the hair
under his arms was also removed. Then Sharon inspected him for facial
and chest hair. To Brad's delight, no beard plucking was necessary. He
suffered through having his eyebrows formed and shaped and also his
hairline was slightly contoured into a more feminine style. Through all
this he remained nude. His hair, long for a boy, was still too short to
shape into any feminine style. Now came the "dressing-up". Sharon had
laughed uproariously when Brad had removed his nylon stuffed bra.
Telling him to take a scented bath, she grabbed her car keys and purse
and drove to the drugstore. Before she left she warned him against
playing with himself.
Within a half-hour she returned carrying a large paper shopping-bag
holding her purchases. Entering the master bathroom she encountered
Brad just after he had stepped out of the tub. Seeing him, a smile came
to her lips and putting her hands together, she gave the youth an
ovation. Brad stood before her with the bath towel wrapped around his
chest and a second towel around his head in the form of a turban. The
effect was one of a flat-chested girl. Seeing his features unencumbered
by clothing and framed by the towels, she realized how easy this
transformation would be. Dumping the contents on the bed she turned to
her dresser. Searching through the drawers she selected articles of her
own for him to wear. Handing him the selections Sharon coached him in
getting dressed. When he went to roll both nylons onto his toes, she
corrected him with a slap across his bare tush.
"That's how teenage girls in a hurry get dressed. A woman takes her
time and enjoys the sensual feel of the nylons on her toes, ankles,
calfs and thighs. She never rushes getting dressed! Let whoever is
waiting for her...wait a bit longer. Getting dressed-up, for a sensual
woman, must always be erotic, or what's the sense of being female. Now
do it right this time."
Brad, following her direction, was amazed how much more he enjoyed the
sensations. He realized it was partially due to taking his time, but
also because his legs were now clean-shaven. Attaching the clips of the
powder blue garterbelt to the nude colored nylons, he paused long
enough to slid his hands over his hose covered legs. Telling Sharon
that she was correct brought a smile to his Aunt's lips. Inserting his
legs into the matching lacy panties, he "slinked" them up and over his
thighs and "snuggled" them into place around his ass, again taking his
time and enjoying the feel of the material as it enveloped his form.
Tucking his penis back between his thighs was the only way for the
panties to fit properly. This he accomplished with difficulty, since he
was sporting a semi-hard erection. When he finally succeeded, Sharon
came over and adjusted the fit. Handing Brad the bra that matched the
panties and garterbelt, she watched him as he clipped it in front,
twisted it around, inserted his arms and pulled it in place. As Brad
bent over to pick up the extra nylons (to fill the cups), Sharon again
slapped his now pantied ass.
"That's not how a woman bends to pick something up. She either squats,
remembering to always keep one leg slightly back of the other, knees
close together, or she bends from the waist keeping her knees locked.
You must always keep in mind, it's not the clothes that will give you
away, it's acting or moving in an improper or un-lady-like manner. Here
let me give you another example; Take a look at your nails." Brad did
as instructed and again received a slap on his pantied ass.
"See, that's what I mean, males curl their fingers into their palm to
view their nails. Woman stretch their fingers and hands away from
themselves, like this. We want to see the overview, the backs of our
hands and the polish on our nails all at the same time. See the
difference, good! Now, instead of balled up nylons, slip these into
your bra. These are your new tits. The medical term is prosthetic
breast sacks. I picked them up at the medical supply store next to
Walgreen's. They are used by women who have had breast removal surgery.
They'll give you the natural look, weight and feel of real breasts and
will move with your body as you walk."
As Brad went to insert one his Aunt began laughing.
"Not that way, it's up-side-down, here let me help you."
Brad stood still as his Aunt inserted and adjusted the gel-filled
devices. Sharon cupped her hands and lightly bounced both sides of his
form-filled bra, adjusting the straps until just the right tension and
jiggle was achieved. Satisfied, she stepped back admiring the effect.
Immediately, Brad felt the difference. There was an added weight
pulling on the bra and the straps formed the slightest indentation at
his bare shoulders. He brought his hands up under both cups and fondled
each cup in turn.
"I have tits!" he boldly announced. "Oh, this is definitely much better
than the nylons. They really feel like they're a part of me!" As he
turned he felt the momentary delay in their movement and the correcting
sway after he stopped. Taking a few steps, he felt how they "jiggled"
and bounced. "These are wonderful! So much more lifelike. Look they
even have nipple marks you can see through my bra. Oh, thank you
Auntie. This is wonderful!"
"You're welcome, now let's work on your make-up."
The next hour was spent trying different shades of base, mascara,
lipstick and eye shadow. Sharon did all the work as Brad listened and
watched attentively. When she was finished, what she had accomplished
was a work of art! No longer was he just pretty, he was beautiful.
Sharon's skills had enhanced his original, somewhat feminine facial
features, to a new level. Looking at himself in the mirror he saw a
younger version of his Aunt.
It was now obvious they were related. Sharon, satisfied with the result
of her handiwork, said, "When you learn to do as well by yourself,
nobody will be able to discover your real gender just by your looks. I
have another surprise for you, give me your hands."
Extending his hands, Sharon began attaching the false fingernails she
had purchased. After they were set, she filed them into shape, brushed
them with several coats of red nailpolish which matched his lipstick.
Leaving the room for a moment, she returned carrying a handful of
assorted costume jewelry. These were tried until the effect she desired
was accomplished. He now wore a thin gold chain hanging from his neck,
with a Kremetz Rose resting just above the rise of his breasts. A pair
of matching earrings, two cocktail rings and a thin gold watch
completed the fashion statement. Stretching her hands out as she had
been taught, Lynn marveled at how different they now looked.
Training Brad how and where to apply perfume came next. This was
followed by teaching him the different ways to step into a dress and
also how to step into high heels. For the first time in eighteen months
Brad realized he had been putting on his heels like a boy, with one
ankle over his knee. The final step in his transformation was the wig.
Sharon went to her closet and selected a light honey-brown, long
tressed hairpiece with a flip. Placing it upon his head, she then
brushed out the snarls. The finished effect was outstanding! Walking to
a full-length mirror Brad stood there with the sweetest of smiles.
Turning to his Aunt, with misty eyes, he ran to her open arms and
expressed his gratitude. Sharon was just as pleased. When she had
agreed to the transformation, she had done so with some misgivings. She
no longer felt any doubts. Brad definitely looked better as her niece
than as her nephew.
Thinking aloud, she said, "I always wanted a daughter...now I have one
in the form of a niece."
The rest of the late afternoon was spent practicing feminine
mannerisms. As Brad became more adept, Sharon decided to discuss how
their new lifestyle would work. It was decided to pass Lynn off as an
eighteen year old. The manner in which her Aunt had transformed him,
helped Lynn to look older anyway.
As the light began to fade, announcing evening, Aunt Sharon asked,
"Would you like to go out to dinner and maybe a movie?"
Lynn's response was immediate, "I would love to go out with you! Does
that mean your comfortable being seen with me in public?"
"Yes! I have no doubt you'll pass. I know a wonderful little Italian
restaurant near the mall. They have the best pasta in town. After
dinner we can see a movie if the timing is right or we can 'window
shop' for a while. Let me freshen up a bit, first. My outfit is too
casual if your going to go dressed like that. Why don't you join me in
my room while I change? I think it's time you see what a real woman
looks like!"
Brad couldn't believe his ears. If what his Aunt was saying was true,
he was going to see her naked! Quickly following, he entered Sharon's
room. There she motioned him to take a seat on the bed. She began to
strip. When she removed her bra, Brad gasped in astonishment, bringing
another smile to the woman's lips. Wasting little time Sharon selected
new lingerie, a different dress, a pair of heels, repaired her make-up,
brushed her hair, added perfume, jewelry...all under Brad's attentive
and never wavering view. Within forty minutes they were on their way.
Lynn had been given a black shoulder bag, a lace trimmed hanky,
tissues, a hair brush and make-up to be carried in the purse. Her Aunt
also coached her as to the proper manner to carry a purse.
When they got to the restaurant, they were informed there would be a
forty-five minute wait for a table. Deciding to wait in the lounge,
they left Sharon's name and proceeded into the bar. Others had had the
same notion and there were no seats available. Before they could decide
on a new course of action, they were offered places at a small table by
two men. Lynn was reluctant, but was forced to follow her Aunt's lead,
when she accepted their invitation. Sharon introduced Lynn and herself
and the men did the same. They gave their names as Bob and Tony. They
were in town for a convention, had been bored with the drunken antics
of their fellow conventioneers and had set out on their own. A cabby
had suggested the restaurant and here they were. They offered to buy
the ladies a drink, which was accepted. It was obvious the guys were
hoping the women would join them for the eveni