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Military School Crossdresser
by Kresha Matay
Tim was a sensitive young boy, bright and intelligent, but lacking many
of the physical characteristics of his father, Joe. The father had
wanted a son who was interested in sports, hunting and fishing just
like himself. Unfortunately, through no fault of his own, young Tim
could not measure up to the desired image. Joe had expected his son to
grow up to "be a chip off the old block" and when he didn't, his father
felt "cheated". Tim might have grown up the way his father wanted if
he hadn't contracted Polio at the age of eight. The youth was
paralyzed from the waist down. Though he did completely recover the
use of his legs through a long series of operations and physical
therapy, the doctors felt his growth had been impaired. He would never
be as big or as strong as he might have been. Due to his illness, Tim
also missed a lot of school and was two years behind his age group.
These shortfalls caused the father to ridiculed his son whenever he
failed to satisfy the man's absurd notion of what his child should be
like. When this occurred, Tim sought consolation in the loving arms of
Rita, his mother. Here he found the love and emotional warmth he so
badly desired. This only added to his father's frustration and
reinforced his resentment against both his "sissy" son and his
"coddling" wife. This hostility was augmented by the "darts" Joe
received from his macho chums at work whose sons all played Baseball
and Football. His constant bitterness manifest itself in a pattern of
physical, mental and emotional abuse against both the mother and son.
As most often happens, the mother, protecting her child, transferred
her love from the husband to the son and vice-versa. Tim, now in the
initial confusion of puberty, misunderstood his mother's attention and
developed a strong personal attachment to Rita, her belongings and more
specifically ... her clothing. Any personal item of his mother's
became a symbol of the good things in life to the confused youth.
Everything that belonged to her was pretty or beautiful or made him
feel safe, warm and "fuzzy". Everything that belonged to his father
was rough, ugly, caused him pain and got him into trouble. He
rationalized, if he had been born a girl, he wouldn't have been
expected to be knowledgeable about cars, guns, sports equipment or
tools, all the things he hated.
This eventually led him to secretly playing with his mother's personal
items. One day, he took his mother's underwear from the clothes
hamper. Dressing up as a girl, he fantasized he was Rita's daughter
instead of her son. He so thoroughly enjoyed the fantasy, he repeated
his actions every time he was alone. With each new incident of
crossdressing his fantasies evolved till he developed a second persona
as Sarah ... his mother's daughter. As he grew older, Tim found he
enjoyed the crossdressing more and more along with the emotional
excitement he derived from it.
One day while performing a surprise cleaning of his bedroom Tim's
mother discovered an assortment of her recently "misplaced" lingerie
hidden inside her son's pillowcase and between his mattress and the box
springs. Realizing how they must of gotten there, she suspected he
used the lingerie for purposes of arousal and masturbation. Amused and
concerned at the same time, she decided to confront him. That
afternoon, upon his arrival from school, she called Tim into her room.
Rita, holding up the confiscated lingerie in her hand, said.
"Young man, would you explain why I found my lingerie hidden in your
pillowcase and under your mattress? I'd certainly like to hear what
possible justification you might have that would explain how it got
there, why you've hidden it there, and what you wanted it for in the
first place!"
Confronted with the evidence, he broke down in tears, admitted his
crossdressing and explained the fulfillment he derived from wearing her
clothes. Holding nothing back, he declared how badly he wished he was
her daughter instead of her son. The intensity of his desire to be her
daughter surprised Rita. His confession projected not a simple
fondness for her clothes as she might have expected, but a sincere
desire to change his gender. Rita, in an effort to discover how deep
his desire ran, began asking a series of disguised questions. The
answers ultimately convincing her of Tim's sincerity and more
critically ... his desire to be female. Assuming he would continue to
borrow her clothes and crossdress no matter what punishment or
corrective action she enacted, Rita decided that the best course of
action was to allow him to pursue his crossdressing, but under her
protective guidance. After all, she mused, "The remedy is more likely
worse than the actual problem." She secretly "felt" he might eventually
outgrow his fetish as the novelty of wearing her clothing with her
consent wore off. Rita's decision was partially influenced by her
absolute certainty as to what her husband's ugly reaction to Tim's
crossdressing would be. She promised Tim she would keep his secret
from his father, but warned him to be more careful in the future. Rita
demanded his promise that he would crossdress only when his father was
away from home and only in her presence. Tim enthusiastically agreed
to her demand when Rita offered to teach him how to dress-up and also
offered part of her wardrobe to him as his own.
Over the next three years, she kept her promise by presenting him with
various feminine attire including dresses, skirts, blouses, high heels,
a panty-girdle, nightgowns, breast inserts, panties, slips, nylons,
bras, pantyhose, garterbelts, costume jewelry, make-up and even a long
tressed blonde wig. These were kept in her clothes-closet (by this
time Rita and Joe were sleeping in separate rooms), with the
understanding that they were really Sarah's to enjoy. As his secret
crossdressing became a larger part of his life, his mother's
involvement also increased.
Rita came to realize how much happier both she and her child were when
he dressed as her daughter. Deciding his life as a boy was miserable
enough she began to encouraged Tim to become feminine more often. The
next level in her son's transformation was natural and easier ... she
assisted Tim in his attempts to mimic the gender differences. Now she
used all their free time teaching him feminine mannerisms. She trained
him in the art of applying makeup, coached him to speak with a higher,
yet softer, more gentle voice and became his gender tutor. By the time
he graduated junior high (at the late age of eighteen), he could
comfortably pass as her lovely young daughter. Tim could mimic the way
a young woman walked, talked and presented herself. He had mastered
all the subtle mannerisms that differentiated the genders. When
dressed in his feminine raiment, he truly became his alter-ego Sarah.
All this occurred without the slightest knowledge of his abusive
father.
His mother, who had always wanted a daughter, now found an answer to
her lack of one. Whenever her husband left for an extended fishing,
hunting or business trip, which was quite often, Tim would spend the
entire timeframe dressed as Rita's daughter. As soon as her husband's
car pulled out of the driveway, Rita would call Tim to her bedroom and
transform him into the lovely Sarah. They would pass the whole time
just as any other mother and daughter. As Tim grew within the role,
they ventured out-of-doors, taking short trips into the real world. At
first, these were car rides late at night, with little chance of
discovery. As they both became more confident with his ability to
pass, they added short stops at McDonald's and other fast food
restaurants.
The next logical progression was running errands as mother and
daughter. With each new success came more daring adventures. One
momentous day Sarah and Rita decided to go to the mall for some
shopping. The day was a total success! They shopped all the women's
stores, taking great pleasure in Sarah's ability to "fool" the
saleswomen. They tried on dresses, bought new lingerie, bought high
heels, bought cosmetics, had lunch in the food court and took in a
movie as they thoroughly enjoyed Sarah's newfound freedom. After this
successful outing, they went everywhere as mother and daughter. No
fears, no concerns, truly comfortable within their characters. Two
females going to museums, art galleries, restaurants and theaters like
so many other mother's and daughter's. If there was a good play being
performed, that's where they would be found, dressed in their finest
feminine attire, reveling in their joint womanhood. At home, in the
evenings, adorned in their silky negligees, Rita spent hours talking
about her life as a young girl. She told Sarah stories about her
girlhood, her dates, her first kiss, her first love and the first time
she made love. They sat for hours like other mothers and daughters,
talking about clothes, hairstyles, make-up and how marvelous it was to
be female. They would nervously giggle and laugh at the idea of Tim's
father finding out about "Sarah". Their conversations included such
topics as how his mother felt as a woman. What her dreams and
fantasies were and had been. How she viewed men and how she felt about
her marriage to Joe. Each time they chatted was another learning
experience for Sarah. The information Sarah's mother related provided
her with a superior understanding of the feminine gender, i.e.., how
the female mind worked, what were the "precepts" of womanly conduct and
how his mother viewed her status in society.
One evening, when Tim asked a question about female sex organs and how
they functioned, Rita went to Joe's bedroom, opened her husband's
dresser drawer and extracted a few of his "hidden" girlie magazines.
Then using the most explicit pictures of the absurdly posed models she
described all the erogenous areas of the female body and the passion
women derived from loveplay. Having gone this far, it was a small step
for her to describe the various techniques that excited a woman. She
explained how most men expected their own sexual satisfaction without
concern for their partner. This occurred because men felt superior to
women and how stupid an idea this was in reality.
"Women should always be treated with the greatest respect and should
never be used as a sex toy! All the courtesies and culture that make
up human civilization are the results of female efforts to make our
lives more beautiful and more satisfying. I want you to always
remember, almost any male can father a child, it takes a woman to give
the embryo life, to nurture and carry the child in her womb as it
develops and then when she gives birth the future of our civilization
is guaranteed. That's why I expect you to always regard women with
honor, reverence and esteem."
While Rita felt totally comfortable discussing any topic with her
daughter, she remained guarded in her dress. Though she assisted him
in his transformation and at times they helped each other get dressed,
she never allowed either herself or Tim to be totally nude in front of
the other. They did, at times, walk around the house in panties and
bras, but that was as risqu'e as they got. Their's was not a sexual
situation, but one of love and understanding.
This closeness between the two and Tim's girlish traits, didn't
altogether escape the notice of his father. While their secret
remained hidden from him, he now thought his son was turning gay. His
father decided that Tim needed discipline and physical training to
"make him into a man". When Tim was eighteen, he was sent to a
military boarding school to finish his last two years of high school.
Rita, protested most vehemently but to no avail. Now Tim's life
changed dramatically. He was still the subject of daily ridicule, but
now it was the other male students, not his father who mocked the boy.
The other cadets instantly recognized and made fun of his gentle voice,
mannerisms and polite attitude. In addition, he no longer was able to
escape into his other persona ... Sarah. As the days went by, he
withdrew from all contact with the other boys at school.
One Saturday morning, when most of the other students were home on
weekend leave, he stayed rather than go home to his father (Rita was
away). He decided to walk over to the main building to get change for
the Coke machine. This was his first time inside the offices of the
school. He had, of course, noticed the female secretaries when they
walked to the cafeteria (all the boys had, since they were the only
women around), but had never spoken to any of them. As he opened the
office door, he was run into and knocked over by the two small sons of
one of the secretaries. The woman ran over to see if he was hurt at
the same time yelling for her kids to, "Stop!"
"Are you hurt? No! Good! Please excuse my children, I brought them
with me because I couldn't get a sitter and I have all this paper work
to finish by Monday. I don't know how I'm going to get it done and
watch them at the same time. Oh, I'm sorry, I'm Mrs. Kinzie and these
two rascals are my son's Jeff and John."
Tim introduced himself, then said.
"It's a pleasure to meet you Mrs. Kinzie. If you need someone to
watch the boys, I'll do it. I'll take them to the gym where they can
run and chase as much as they want and won't be in your way, so you can
get your work done."
This offer was met with cheers from the boys and after a slight
hesitation, grateful acceptance from their mother. In the course of
further conversation, Mrs. Kinzie suggested he call her Jean, at least
when none of the school officials or cadets were around. When Jean
offered to pay him, he graciously refused her offer. After Tim and the
boys left, Jean returned to her desk, but instead of resuming her work,
she thought out loud.
"He's not like the other students in this school. They wouldn't have
offered help to one of us secretaries. They're so stuck up and "macho"
they only stare as we walk by while making indecent gestures behind our
backs. He's different, more sensitive and much more responsible than
the other students. I wonder how he manages to cope in this milieu?
If he stays that way, he'll make some girl a wonderful husband and
probably a great lover. Not like that insensitive bastard I married!
I hope his new wife gives him what he deserves, a whip across his ass.
That's just what he needs to teach him respect for all women!"
Jean was a strikingly beautiful and sensuous woman of twenty-two. Her
classically molded features, crowned by a mass of auburn hair, were
complimented by the firm fullness of her breasts, flat stomach and
carried by two lovely defined legs with finely turned ankles. While
some of the other secretaries might have appeared more sexy (they wore
more revealing clothes), she was the one who constantly received
requests for dates, but refused them all. Being a working mother, a
surrogate father and raising the boys left her little time for a social
life. Also, being "used" by another male was not a goal she desired.
When sexual frustrations reached a peak she could no longer control,
she shamefully fingered herself to an orgasm. Of late, it was getting
more and more difficult to reach fulfillment, also her needs seemed to
return quicker.
Thinking of her EX and how unsatisfying their past sex life had been,
caused desire to intrude into her consciousness and a warmth began to
build between her legs. Without realizing it, her hand crept to her
rising breast, where she was surprised to find her hardened nipple
protruding against the bodice of her blouse. As she brushed her
fingers against the cloth, she moaned in pleasure. Her conscience told
her she should stop, but her fingers refused to obey. Leaning back in
the chair with her legs splayed, she pinched the pouting nipple of her
left breast. Almost out of control, the shock of passion that drove
through her body caused her high heels to "rat-ta-tat-tat" against the
floor tiles. Jean felt the wetness building in the crotch of her
panties. The fire in her pussy sent her last inhibition up in smoke.
Raising her buttcheeks, she drew her tight skirt to her waist and
slipped her hand inside her panties. Using her middle finger she found
the source of her passion. With her eyes closed, she fantasized a
faceless young lover teasing her hardened clitoris. Each flick of her
fingertip equaled the flick of her lover's probing tongue. She
installed in her fantasy lover all the special qualities of sensitivity
and lovemaking she most wanted from a man. As her emotions rushed
towards orgasm, her fantasy lover raised his head. The shock of
recognition brought her to a screaming, leg trashing climax. The most
powerful climax of her twenty-two years. The face in her fantasy was
Tim's! As her passions subsided, her shame and confusion grew. Her
mind raced to find an explanation. None being available, she began to
cry softly.
"How could I play with myself, here of all places and why would that
sweet boy's face be the one in my fantasy. Am I so horny I'm going to
start seducing tender young boys. Have I no shame?"
In an effort to compose herself, Jean straightened her clothing and
proceeded to the ladies room. On the way back to her desk, she heard
the laughing voices of her two sons emerging from behind the closed
doors of the gym. Deciding to see how they were getting along, she
reached for the door handle when she was struck with a concern.
Checking on the boys might be construed, by as sensitive a youth as
Tim, as questioning his ability. Not wishing to hurt his feelings, she
turned and took the stairs up to the second floor. A four foot wide
landing ran along three sides of the gym. Stepping quietly through the
swinging doors, Jean found she was positioned directly over where the
three boys were playing. They were obviously having a good time
wrestling with each other on some foam mats left just for that purpose.
In a moment it became obvious that it was her two sons paired against
Tim and he was holding back, allowing them to "pin" him to the mat.
Just then, they pushed him over on his back, one pinning his arms while
the other sat on his legs.
Tim's eyes momentarily met hers ... she was discovered. In the same
instant she realized he was no longer looking at her face, but was
instead, staring up her skirt. As quick as she realized what was
happening, that's how quick another fire grew in her womb. Grasping
the open railing for support, she closed her eyes and again imagined
young Tim's head positioned between her splayed thighs, stroking his
tongue against her pussy lips, munching gently on her clit. A soft
passion-filled groan escaped from between her clenched teeth. Jean,
lost in her fantasy, didn't understand her next action. She found
herself spreading her thighs even farther apart thereby exposing
herself completely to Tim's view.
Tim enjoyed playing with the two boys. He knew he could beat them
because of his weight and size, but decided to let them win. When they
pushed him to the mat he found their mother looking down on them. His
eyes were quickly drawn between her legs and up her skirt. His
position enabled him to see the exposed welts of her nylons and the
whiteness of her naked thighs before they merged into darkness. He
fully expected Jean, based upon his understanding of how a woman should
protect herself from exposure, to immediately step back or at least
tightly close her legs. When instead, her thighs spread even wider
apart, he rationalized that Jean didn't know what she was "showing".
His eyes ran up past the welt of her nylons and were only stopped by
the thin strip of white lacy nylon covering her womanhood. Not able to
tear his eyes away, he felt the dick in his shorts thicken and then
push it's way down his leg.
Jean "felt" Tim's eyes on the center of her passion. With her eyes
still closed, she immersed herself back into her earlier fantasy,
"sensed" his trusting tongue against her throbbing clitoris and without
touching herself, orgasmed profusely. Her legs violently shook as her
pussy drenched her panties, her womanly juices running down her naked
thighs. It was as strong and satisfying an orgasm as the last, all
without any physical contact!
Tim, unaware that Jean was in the grip of an orgasm and spurred by his
fear of discovery, quickly admitted defeat to the two boys. Using the
excuse of having to pee, he rushed off to the john, but not before Jean
looked down and was pleasantly shocked to see the large hard-on he
unsuccessfully tried to hide. Not wanting to be discovered by her
sons, she returned to the ladies room to repair the damage to her
clothes, while Tim used his visit to the locker-room to bring himself
to orgasm, all the time remembering what he had seen.
Jean returned to her desk and spent the next two hours in the office
trying to concentrate on her work. Eventually, she was forced to
accept the fact that she wasn't accomplishing anything. Her mind kept
wandering back to what had occurred earlier. Locking the office, she
entered the gym where she was met by the enthusiastic reports of how
much fun her children were having. Both Tim and she acted as if
neither had been aware of the other. Since it was almost lunchtime,
Jean suggested Tim join them in the cafeteria and he willingly
accepted.
During lunch, she questioned him in such a manner, that he revealed
personal information about himself without being aware of how much he
was openly divulging. She grasped his problems with his father,
inferred his emotional attachment to his mother and now understood why
he was so sensitive towards women. Halfway through lunch, they were
joined by her boss, the Commandant of the Military Academy. In the
conversation, she explained how they had met and how Tim was graciously
watching her two boys while she worked. Jean explained her on-going
problem of finding a qualified sitter and asked her boss if she could
avail herself of Tim's services on a semi-regular basis. That is,
whenever she couldn't find a sitter, could Tim watch the boys at her
house. After further discussion, his complete approval was given. He
even approved Tim, if necessary, being allowed to sleep over if she had
a late date. Lying, she explained that this was the exact case tonight
and her boss directed Tim to pack a bag and sign out into Jean's care.
After lunch, Jean returned to work, while Tim went back to watching the
kids. She "buzzed" through the mound of paper in record time. Making
sure she was alone, she called her older sister Susan and asked if she
would "take" her nephews to a movie that night. After Susan agreed,
Jean hinted that she might have a male visitor at which point her
sister offered to keep the boys overnight. Jean then went into a
thorough explanation about Tim. She told her sister she had been so
happy to get her boss's permission for Tim to baby-sit that she hadn't
realized the complication his being there might cause. If he spoke out
of turn, about her male visitor, back at the school, her job might be
in jeopardy. She suggested that Susan not bring up her keeping the
boys overnight and later, act as if the idea was a last minute decision
based upon the lateness of the movie. Susan readily agreed.
With her plans set in motion, she locked the office, found the three
boys, waited for Tim to pack and then drove to her house. During the
drive, she allowed her skirt to rise above the tops of her nylons and
felt rewarded by the bulge that grew in Tim's uniform pants. After
dinner, Susan showed up, asked to take Jeff and John to a movie saying
nothing about their staying over. When Susan, on the side, asked her
sister about Tim, Jean said she would return him to the school when she
left for her date, explaining to The Commandant she wouldn't be out as
late as she had originally anticipated. Susan wished her well, kissed
her cheek and left with her nephews.
Jean asked Tim if he minded being left alone until the boys came home
while she was out. Tim, realized he would be alone in the woman's
house for hours and as it had been a long time since he had the chance
to play in panties, nylons or a slip, seized upon the opportunity and
readily agreed to stay and wait for the boy's return. Jean cautioned
him not to say anything to her boss about the change of plans as he
might not understand. Tim noted her concern and promised he wouldn't
say a word about the change.
Jean suggested he watch TV while she went and prepared for her date,
which is precisely what he did. Leaving him alone Jean went to her
room and changed into the sexiest outfit she owned. The dress was
backless, made of polyester wool crepe, dyed black and did nothing to
hide her charms. Under it she wore a black garterbelt, black sheer
nylons and French cut, black sheer panties and no bra. Finishing off
the effect she wore 3" black patent leather heels. Looking at herself
in the mirror, she knew the reaction she would get from the young boy.
When Jean entered the den, supposedly to give Tim some final
instructions, she was rewarded by the look of desire in the youth's
eyes. He could barely mumble his understanding as he riveted his
attention to the exposed roundness and the tanned cleavage of her
breasts. When she spun around to leave a low gasp of youthful
appreciation escaped from between Tim's lips. Jean's low-cut dress had
exposed her nude back and the obvious fact she had no tan lines. It
had not escaped Tim's attention that Jean must sunbathe in the nude.
"Why thank you for that reaction. Now I hope I get the same from my
date. Do you really like the way I'm dressed? It's not too revealing
is it? Maybe I should change? You don't think I'm too old to run
around dressed like this?" She coyishly asked.
Assuring her she looked fantastic, Tim unsuccessfully attempted to hide
the growing bulge in his pants.
Pointing at his erection, Jean exclaimed.
"Oh, I must really look good if I can cause that much of a reaction
from a young boy!
Tim lowered his head, truly embarrassed and began to apologize.
Jean, grasped his hand and said.
"Tim, let's sit down on the couch for a minute and talk."
As they sat down, she stated.
"There's no need to be embarrassed, women dress this way on purpose.
We do it to get men's attention and excite them. Why should you expect
to be immune, afterall your not that much younger than I am! If I
didn't obtain a reaction from you I'd be disappointed. A woman likes
to know that men think she's sexy, or we wouldn't go through all the
trouble to look this way. The type of clothes we wear causes women to
accidentally expose their bodies to men's perusal everyday of our
lives. Think about it, every time we sit down on a chair and cross our
legs, we expose at least our thighs. Getting up, if we're not
especially careful, allows men to see up our skirts all the way to our
panties. Women have become accustomed to daily exposures of their
bodies so we use it to our best advantage. Men don't realize we do it
on purpose! We dress to tease men! A man's vivid imagination is a
woman's greatest weapon in the war between the sexes. It gives us
power over men. Almost every man I've ever met will 'break his neck'
to see up my skirt. Sometimes I purposely let someone I really like
look up my legs ... like I let you this morning."
Tim exclaimed. "You knew that I was looking up your skirt? Does that
mean you really like me?"
"Of course I like you, I like you a lot! I think your very sweet!
What happened today, started out as an accident. I was checking on the
boys, but didn't want you to think I was checking up on you. When I
stepped out on the landing I had no intention of even being seen. When
you looked up and discovered me, I felt I might have hurt your
feelings. Then, when I realized where your eyes were looking, it
pleased me that you weren't upset with me and that you liked what you
saw. I want to be honest with you, if you'll be honest with me? How
about it?"
Tim, afraid his voice would crack, nodded his agreement and Jean
continued.
"Having you look up my skirt excited me! That's why I spread my thighs
so you could see even better. I wanted you to see more of me! I knew
the effect I was having on you. It didn't matter how much you saw. We
certainly weren't hurting anyone. What started out as just another
accidental exposure, turned into two people enjoying the situation. I
got just as excited as you did. Tim, as you grow up, you'll find most
women enjoy being teases. A woman who's comfortable with her body
isn't afraid to expose herself when the situation suits her. Maybe I
shouldn't be telling you all our female secrets or maybe it's time you
told me a few of yours. I know you got hard and then ran off to the
john. Did you play with yourself? Did you come?"
"Yes. I couldn't help it. I almost didn't make it! When I got there
I couldn't believe how hard my dick was. Oh! I'm sorry, I shouldn't
have said that word."
"Tim, it's OK. You don't shock me, I'm an adult woman who has two kids.
Honey, I definitely know what a dick is. How do you think I had those
kids? Did you think of me and my panties when you played with your
dick?"
"Yes!" Smiling sheepishly as he answered.
"Good, I'm glad, that makes me feel even better that my accidental
exposure wasn't wasted."
Kissing him on the cheek and then rising, she said.
"Well, I've got to get going. If you get hungry, help yourself. I'll
probably be late, so don't think you have to wait up."
Tim, hoping to get another look up her short dress, walked Jean to the
car and held her hand as she climbed behind the wheel of her Camaro.
He was rewarded, with another "accidental" exposure, as Jean dropped
onto the low seat, pausing with one leg in the car and the other still
on the ground. Her short skirt sliding back past the tops of her
nylons thereby again exposing her panty covered crotch to the youths
eyes. Thanking him for the helping hand, she commented.
"That nice new bulge in your pants tells me I must have had another
accidental exposure."
Giggling, with a twinkle in her eye she smiled up at him and said.
"I really must learn to be more careful! If I keep having these
'accidents' you might start thinking I'm doing it on purpose and you
know I wouldn't ever do that!", she giggled.
Then lifting her other leg in such an exaggerated motion that she
totally exposed her panty covered crotch, while at the same time
running her tongue across her moist lips. Then closing the door, she
drove off. Watching her drive away, all he could think was, "WOW, what
a woman!" He returned to the family room, tensely waited about 15
minutes and then headed for Jean's bedroom. He stood in the doorway
and peeked inside. The clothes Jean had worn were strewn about the
floor and bed. So were several outfits that had apparently failed to
make the cut. Stepping into the room, he immediately detected a hint
of makeup, perfume and hair spray in the air. The room smelled so
sexy, so sweet, so delightfully feminine he felt his cock rising!
Tim moved to the pile of clothes Jean had worn earlier that day and now
lay discarded on the floor. Using the tip of his shoe to push aside
the skirt, he uncovered her lingerie, including the tiny bikini panties
he had seen earlier that day covering her pussy and ass. Bending over,
he picked them up, brought them to his nose and inhaled deeply. The
musky woman's scent permeated his senses. Placing them on the bed, he
went to Jean's open dresser drawer. Inside were three neatly folded
piles of panties. The styles ranged from tiny, sexy bikinis, more
conservative hiphuggers and finally even more conservative brief style
panties, the kind he and his mother usually wore. He carefully pulled
a second drawer open and looked down at an array of bras, slips and
camisoles. The third drawer displayed hose, both panty style and
nylons along with the garterbelts to hold them up. The belts were much
more feminine than those of his mother. These had lacy little straps
of elastic with bows on them and came in assorted pastels and rich
colored reds and blacks. He pulled the last drawer open and found
Jean's night gowns. Running his hand through the silky material he
tried to imagine Jean in the more revealing ones.
Meanwhile, Jean had driven around the block, parked her car in a
secluded spot and smoked a cigarette. Wanting to rush back home, she
forced herself to wait, knowing any young boy as sensitive as Tim,
would hesitate before he began to snoop. Not really knowing what he
would do, but guessing he would at least go through her lingerie
drawers, she wanted to catch him "redhanded". Holding the threat of
exposure over him would guarantee the youth's total obedience. When
she could no longer wait, she crossed through a neighbour's yard and
snuck up on her bedroom window. Before leaving for her supposed date,
she had left the window slightly open. Using a long handled comb she
quietly pushed the shade aside and saw Tim standing before the opened
drawers of her dresser. Mentally congratulating herself on the success
of her plot, she began to turn away to sneak into the house to confront
the youth. At the last moment she changed her mind. Out of the corner
of her eye she had observed Tim beginning to undress. Not wanting to
miss this, she again positioned herself under the window.
Inside, Tim quickly removed all his clothing. Standing before the
fullsize mirror he stroked his cock and balls with Jean's discarded
slip while inhaling the scent from her panties. His hand pounded his
male organ as he furiously jacked-off. He was ready to spurt his hot
cum across the bedroom carpet when he realized the mess that would be
caused by the blobs of sticky cum. Rushing to the adjacent bathroom,
out of Jean's sight, he climaxed into the toilet. Then using some
tissues, he cleaned himself, making sure he squeezed every last drop
out of his now softening organ.
Jean, who felt cheated, rushed to the back door, quietly let herself
in, snuck into the bedroom and hid in her walk-in closet. All this
occurred while Tim was cleaning himself. Her intention was to surprise
Tim as he returned from the bathroom. She again changed her mind when
he returned carrying additional articles of her clothing, obviously
taken from the hamper. She didn't know what purpose they would serve,
but hoped another demonstration would be forthcoming. Afterall he was
a young boy and was probably ready to come again. What she couldn't
understand was why he was carrying her strawberry blond wig in one
hand. She decided to take a wait and see attitude.
Tim lovingly laid out all the finery across Jean's bed, then picking up
an emerald green garterbelt, he put it around his boyish waist,
connected the clip, spun it around so the fastener was in back with the
garters dangling against his thighs. Then sitting on the bed he
carefully rolled a pair of sheer, black nylons up his legs and expertly
attached them to the garters. Lifting one leg, he provocatively ran
his fingertips over the sleek nylon, removing any looseness or sags.
Doing the same to the other leg, she heard him say.
"Boy, I sure wish I could wear these every day!"
Rising, he carefully straightened the hose and adjusted the straps for
a better fit. Stepping into the matching emerald green satin-like
panties, he slithered them up his legs, past the garters and shimmied
his ass into the delightfully cool material. Pausing to accommodate
his semi-turgid penis back between his legs, he reached for the bra
lying on the bed.
By this time, Jean realized Tim was a crossdresser and a very adept one
at that. He even exhibited the mannerisms of the feminine gender.
Obviously, she mused, he had been coached, probably by his mother or
some other woman! Jean, as she watched, used her free hand to stroke
her nipples through her dress.
This was even better than she could have hoped. Now, with this
knowledge, he would have to obey her every whim. As she observed Tim
feminize himself she became more and more interested, more and more
excited and less and less concerned with the power she originally
wanted over him. Now she desired him as a lover and not as a
"plaything". Jean had always had a hidden desire to lie with another
woman, but had been afraid to take the first step. In fact, it was
rumored one of the secretaries at the office was gay and Jean had
pictured the woman in her fantasies. However, not being brave enough
to approach her, she now found herself with a solution to her craving.
Raising her skirt, she slid the crotch of her panties aside, exposing
her womanhood and began to gently stroke her tunnel of lust. Inserting
two fingers inside herself, she used her other hand to masturbate the
blood engorged bud of her clit. Mentally she warned herself against
losing control or emitting any sound of passion which might cause her
to be discovered. Her mind reeling from the sensuousness of what was
being enacted before her eyes decided she preferred the direction
towards which the bedroom scene was moving versus her initial plan of
control over the youth.
Tim, unaware of Jean's presence, had finished crossdressing. He had
chosen an offwhite blouse with ruffles running down the front and a
black straight skirt that zippered and buttoned on the side. The skirt
was a bit long, as the hemline fell past his knees, but he had chosen
it because it highlighted the round globes of his ass and the slit up
the side displayed his nylon clad thighs to their fullest. Standing
before the mirror he bent forward and placed the blonde wig upon his
head. Adjusting it by running his fingers through the strands he stood
there satisfied with his appearance. Oh, he knew he needed makeup,
jewelry and heels but he wasn't sure if he had the time for makeup and
the rest could be obtained easily enough. He relished the titillating
feelings racing through his body. This was the first time since
leaving home he felt gender correct. Jean's lingerie was even more
satisfying than his mom's. Also, dressing in the clothes of a woman
who was a stranger increased the sensuousness he felt.
Turning, he notice Jean's jewelry box sitting on the dresser. He
walked over to it, reveling in the feel and sound as his nylon covered
thighs rubbed against each other. Tim opened the box and found a
perfectly wonderful pair of gold and red enamel clipon earrings. After
attaching them to his earlobes, he decided he really needed heels and
proceeded towards the closet.
Jean, seeing where he was headed and realizing the probable reason why,
pulled her fingers from inside her pussy, dropped her skirt, grasped a
pair of heels and pulled the door open just as Tim reached for the
handle.
"Are these what your looking for, Tammi?"
Tim was stunned. The shock caused an immediate reaction in his
panties. The blood rushed from his dick to his face, causing his
member to shrink and his cheeks to blush. He was caught! Now his mind
raced from one consequence to the next. Not only would he be thrown
out of school, but his crossdressing would be exposed to his father.
Knowing the punishment would certainly be painful he realized his
mother's involvement might be exposed. He couldn't let that happen, he
loved her too much! Maybe he could convince Jean not to say anything.
Before he could beg, she spoke.
"Tammi, why don't we sit on the bed and have another little talk. Just
us two 'girls'. How about it, sweetie, would you like that?"
Confused by Jean's attitude, but afraid to refuse the woman, Tim nodded
his head as he fought to hold back the tears. Jean took his hand and
led him to the bed where she directed him to sit on the edge. Sitting
next to him at an angle, she slid her right ankle under her left knee.
He immediately noticed the space this opened between her thighs, again
exposing the welt of her nylons. Even though he was scared, he still
couldn't help himself and openly stared at the woman's firm fleshy
thighs.
"Do you like what you see? Good, your supposed to! I told you women
use the way they sit to tease men, its a way of getting power over
them. Can you feel the power I have over you? If I opened my legs
just a bit wider, wouldn't you do almost anything I asked? Of course,
your going to agree to anything I want anyway, aren't you? Otherwise
I'll be forced to call the school and tell them about all this. I can
just imagine what the Commandant and the other boys would say about you
wearing panties and my bra. I can also guess what your father would
say about nylons and a garterbelt. Is that what you want me to do?"
The look on his face told her the answers to her questions without any
verbal response. He definitely desired her silence and would do
anything to earn her cooperation.
"Tammi, that's going to be your new name whenever your dressed this
way, but before we go any further, you'll have to tell me everything
you know about girls and/or women. I also want to know everything
about your crossdressing. I want to know how you got started, how
often you dress-up and who taught you feminine mannerisms? I know you
couldn't become so adept at wearing women's clothes without some expert
help. I must have your total obedience and you must be totally
truthful. If I catch you lying or hiding the smallest bit of
information from me ... we'll stop and I'll take you back to the
school dressed in my clothes and tell the Commandant what occurred here
tonight. I'm sure you don't want that, do you?"
"No, please don't do that!" He begged.
"Good! Now that you thoroughly understand the control I have over you
we can continue our "girl-talk". If you accept my terms and I don't
see that you have any choice, I'll let you continue to come to my
house, dress in my clothes and I'll even teach you more about being a
girl. There will be other exciting things we can do together dressed
as girls, things I'm sure you'll enjoy. All I've said can be yours if
you agree to my terms. Well?"
"Yes, I'll obey your every request and tell you everything."
Now guaranteed of his complete obedience she told him to begin.
As the story of his crossdressing, his desire to have been born a
female and his emotional attraction to his mother unfolded, Jean found
herself becoming aroused. The sexual heat she had experience earlier
began to build again. Asking questions, she determined he was a
virgin, but definitely knowledgeable about the ways of sex. It was
obvious his mother had explained quite a lot. He admitted he had never
seen a woman naked, not even his mother. Girlie magazines, his mother
purchased for him were his only knowledge of nudes.
When he was all finished, he asked.
"What are you going to do to me? Should I start taking off these
clothes? What about your date and when will the boys be back?"
"Oh, those are my other surprises. I don't have a date and the boys
are going to sleep over at my sister's. When I saw you staring up my
skirt today, I knew there was something special about you and made-up
the whole story about a date. I also called my sister and made all the
arrangements for us to be alone the entire night. As for the clothes,
wouldn't you rather leave them on for now?"
"Yes, the only time I'm really happy is when I'm a female!"
"Maybe I shouldn't be telling you this. I like the way you look in my
clothes. Of course you need makeup but even so you make a very sweet
young lady."
"Jean, if you keep my secret, I promise I'll do anything you ask!"
Taking him in her arms, she kissed him. Then forcing his lips apart
with her tongue, she taught him the nuances of "French kissing".
When they separated, he asked her in his best Tammi voice.
"Are you going to introduce me to lesbian love?"
"Yes", she answered.
"Before the night is over I plan to teach you all there is to know
about two women making love. I don't want you to hold back or be
afraid to touch me, but you will listen to my guidance."
Reaching out to each other, they began to kiss in earnest. As their
emotions rose, Jean moved her fingers to Tammi's ruffled blouse.
Unbuttoning it, she reached inside the cups of his bra, smiling to
herself as she discovered the bunched nylons he had used to simulate
female breasts. Slipping the straps off Tammi's shoulders she reached
behind his back to release the catches. Cupping her right hand, she
stroked his hairless chest as if he had real tits. Both were amazed at
the puffiness that rose from his chest muscles to fill her cupped hand.
The nipples elongated, actually reaching the size she remembered when
her own breasts began to bloom. In addition, they exhibited the
sensitivity of female nipples. Jean thought to herself. "Maybe he
should have been born a female!, he certainly reacts like I did when I
was his age!"
Using her tongue, she licked, nipped and sucked each ridged nubbin of
flesh. Tammi's reaction was a series of soft mewing moans as he
twisted his chest to obtain the greatest pleasure from Jean's playful
teasing. Realizing he was getting too excited, too soon, she broke
away and said.
"Use what you've just learned to please me. Always remember, a woman's
body is to be adored, there is no place for roughness, at least until
she's ready to orgasm."
Tim began his seduction by licking and kissing her neck and ears.
Gently, he stroked her bare shoulders and back. Tim slid his hand to
her breast and as gentle as a soft whisper stroked the rising nipple
through the dress material. Gaining confidence, he gently laid her
down across the bed, untied the neck of the dress behind her head and
slowly dragged the material down to her waist, leaving her upper torso
bare.
Jean looked into her young lover's eyes, saw the amazement reflected
within them and smiled up to him. A warm tender glow began to build
within her soul. This was no longer just sex, she realized, this was a
budding love affair. Cupping one of her tender breasts, she raised it
to his lips, moaning as his warm breath fell across the pouting nipple.
Tim took her offering and lovingly licked and suckled as he had been
shown. Using his hands, he stroked and fondled her neck, shoulders,
back, stomach and especially Jean's other breast. He learned what
pleased her and that's where he concentrated his efforts. Every boy
dreams of learning the act of love from an experienced older woman and
he was one of the lucky few whose dream was coming true. When Jean
pulled the nipple away, he knew to concentrate on the other breast.
Jean lay back and basked in the pleasure her youthful lover was
providing her. For a first timer, he was more than adequate, he was
actually adept. As his confidence rose, her need to be in control
lessened. This scared her.
"That's enough of that for now! Stand up and undress me!", she roughly
ordered.
Tim obeyed immediately. He rose and then in a surprise and gallant
move, offered his hand to assist Jean in rising. This attention was
not lost on her. Where a moment before she had been concerned, no
actually scared about controlling his level of obedience, this
sensitive gesture quickly erased all fear. Now she could let herself
go and if the need to take charge ever arose, she knew it was only for
the taking. Tim was too tractable to ever cross her.
Meanwhile, Tim had continued to tease her tits with both his fingers
and his wet tongue. Turning her back and leaning against him, she
said.
"You did that very well! Now show me how you think two women would
make love. Don't worry, I'll help you when you need it."
Tim's fantasies about lesbian loveplay had prepared him well. Reaching
up, he lifted the hair from her neck and "nuzzled" and kissed the short
hair he found there. This caused Jean instant pleasure and subsequent
"goosebumps". As she shuddered in delight, she felt his kisses move
across her bare shoulders, down her spine and only stop when he reached
the last exposed inch of skin at her waist. Grasping the zipper, Tim
slowly pulled, enjoying the view as the dress parted before his lusting
eyes.
Jean's panty covered cheeks displayed their fullness. Then when she
"shimmied" her hips, the dress gently floated to her ankles. The sound
of his surprised gasp of appreciation brought a glow of pride to the
woman's features. There the sexy young woman stood, naked to the
waist, her garterbelt and nylons framing her panty covered ass and her
smooth, sleek thighs. Bending forward at the waist to teasingly
straighten her hose, she was again surprised when Tim knelt down behind
her, hugged her around the middle and ran his face across her
asscheeks. Remaining in the position she spread her thighs even wider,
thereby encouraging him to continue his sensual adoration. Tim used
his stiff tongue to run the crevice between her cheeks. When he
discovered the exact location of her pucker hole, he jabbed his tongue
hard up against it. The moan of pleasure from Jean encouraged him to
continue.
Sliding and twisting backwards through her legs, Tim licked and kissed
her panty covered crotch. Looking upward between her soft thighs, he
noticed how her swollen pussy lips had spread open inside her sheer
panties. Their outline in the now damp almost see-through material
plainly evident. Jean, realizing what his next move would be and not
yet emotionally ready to have her pussy licked ... stepped away from
the youth. Turning and sitting down at the bed's edge, she said.
"Tammi, why don't you slip out of that skirt and show me what else two
girls in love can do with each other!"
Quickly stepping out of the skirt, he caught Jean looking at the bulge
in his panties. Not wishing to destroy the image of two lesbians
making love, he adjusted his dick back between his legs, then knelt
down before his lover's knees. Gently grasping her left ankle he
planted a firm kiss on the exposed upper arch. As he kissed and licked
his way up her nylon clad legs his eyes never wandered from the slit of
black, sheer, silk covering her musky scented womanhood. Upon reaching
her naked thighs he continued his kisses, sliding his hands up under
her tush. Squeezing the firm muscles, he inched his lips ever forward.
Jean's mounting passion finally manifest itself by her grasping his
ears and pulling his face against her panty covered pussy. She knew
her need was now too demanding to curtail. Twisting his head, back and
forth against her panty covered clitoris caused enough pressure to set
her off ... and she doused her panties with her juices. Jean's strong
orgasm excited the youth and he dove forward, causing a second series
of sensual shockwaves to course through the young woman's throbbing
lips of lust. As her vibrations slowed, Tim licked and sucked the
sweet emissions through the material as moans of sexual satisfaction
slipped from between the woman's lips.
Jean lay back basking in the warm afterglow of her two orgasms. Tim
knew that Jean had come and suspected it had been a multiple climax.
Realizing she needed to rest, he slid next to her on the bed. Ever so
gently, he ran his fingertips up and over every sensuous curve of her
delightfully luscious body, being extra careful not to arouse the
woman's passions any further. Snuggling up to her ear and in his best
Tammi voice, he made verbal love to her. Recalling to his lover how
excited Tammi had gotten from their mutual girlplay. Telling her about
the flood of erotic sensations that had assailed Tammi's breasts and
sopping wet "cunni". This whispered fantasy recreation brought joy to
Jean's face and an understanding of their new relationship. Jean's
initial desires had been brought about by pure lust, now that lust was
replaced by feelings of tenderness for the young boy/girl resting his
body beside her. Obviously some of her initial plans needed
reconsideration. Maybe she should "talk" to his mother.
"Tammi, remember your promise to tell me everything?"
"Yes," he answered.
"How would your mother feel about you spending some of your weekends at
my house?", she asked.
Tim, not knowing where she was headed with the question, asked.
"What do you mean?"
Jean spent the next hour discussing her ideas with him. When she
finished it was agreed that she would write a letter, on school
letterhead, inviting "mom" to attend a Mother's Tea and weekend visit.
The invitation would explain that those invited women who lived far
away were being offered lodging at the homes of female employees of the
school. Tim's mother had been selected by Jean since her son was
familiar to her. In the letter, Jean would explain how she had met Tim
and how he was "sitting" for her kids.
Tim encourage her to hint there was more to their relationship. He
suggested Jean comment on how much help Tim was in selecting outfits
for her to wear and how they had gone clothes shopping together. He
felt these hints would insure his mother's attendance. Tim was also to
telephone his mother and if necessary also drop small hints. Tim felt
sure she would accept, if only to get a weekend away from her abusive
husband. After his "mom" arrived, they would explain the real reason
... his need to crossdress. Depending how well "mom" reacted, they
would explain everything. If this was received by his mother in a
positive manner, the three "women" could come up with a plausible
scheme that would satisfy both the administration and "mom's" husband.
Their plans complete, they resumed their loveplay.
Jean, now decided that it was time he lost his female virginity.
Removing her panties and gently cleaning her pussy lips with a warm
washcloth, she proceeded to explain the inner workings of the female
sex organs. Spreading the puffy outer lips of her pussy she tutored
him as to how women satisfy each other with their flicking tongues and
fingers. Stroking the bright red bud of her still swollen clitoris she
explained it was as sensitive as the crown of his penis and must be
approached with gentleness.
"I'll show you what I mean!" she said.
Reaching between Tammi's legs, she gently massaged Tim's cock and balls
still encased in their satin pouch. Within seconds he was ready.
Slipping the panties over his hard-on, Jean stretched the elastic
behind and under Tim's balls. This caused his male organ to stand
straight out from Tammi's sparsely haired pubic bone. Cupping the
sack, she teased the sensitive area behind it with her nails. Licking
her lips, Jean lowered them to the purple tip of Tammi's pulsing penis.
Parting her moist lips she engulfed his entire crown. With a slow,
twisting motion and a swirling tongue, she sucked her way back to the
tip.
Tim couldn't believe the sensations Jean's mouth was causing. He had
never gotten this excited, this quickly. He knew he couldn't take much
more of her licking and sucking. When he felt his balls "tighten up"
and the jism rise he tried to pull away, afraid he would upset Jean by
shooting off in her mouth. Jean's lips however wouldn't let go. Her
jaws muscles held him tightly as she pulled the cheeks of his ass
forward with her hands. As she increased her strokes, she felt his
organ momentarily swell and then spasm in her mouth. Using her cheek
muscles to suck out every drop, she swallowed every last spurt. Using
her tongue, she then licked the excess that had run down his shaft,
hoarding it in her mouth she "French-kissed" him. Tim tasted his own
salty warm fluid and was shocked to find out he enjoyed the experience.
Rising, Jean left the bed area and went to the linen closet in the
master bath. Fishing behind some sheets, on the top shelf, she found
the large strap-on dildo she had hidden there. She had purchased it,
just recently, in the hope that the dildo size would resolve her
masturbation problem. While she hadn't really needed the strap-on
device, that's the way it came. Slipping it on, she inserted the
rubber cock through the opening from behind and positioned it so it
"rode" against her clit. Grabbing a jar of Vaseline jelly from her
vanity, she returned to the bedroom.
Tim had assumed Jean had left to use the john. He had spent the time
she was absent, basking in his own afterglow. When he saw Jean emerge
from the bathroom, with the huge swinging dildo at her crotch, he was
scared and confused. He hopefully asked.0D
"Are you going to teach me how to suck a cock? It's not necessary, I'm
only turned on by women!"
"No!" she leered down at the youth.
"Tammi, I'm going to make you a real woman, I'm going to take your
virginity. You can't be a real girl until you've feet a cock inside
your 'pussy'!"
Immediately guessing what Jean had in mind and in fear of the dildos
size, he began to object. Then remembering his promise to completely
obey the woman, he resigned himself to being "fucked".
Jean had him assume the subservient position of leaning on his elbows
and knees. His firm cheeks naturally spread for easy penetration.
Then lathering both the dildo and two fingers of her hand she worked
the lubricant around the squinting eye of his tush. Using first one
finger and then a second, she coated the inner walls of his anal tract.
Tim for his part, found he was enjoying Jean's fingers slithering up
his ass. Surprised by the sensations that coursed through his
genitals, he was getting semi-hard. Jean told him to relax his
sphincter muscle and he found the finger fucking even most pleasant.
When Jean felt he was fully primed she positioned the dildos bulbous
head at the pouting entrance and surprising him, pushed the crown
portion into his surrogate pussy. Tim let out a loud piercing scream
of abject pain and tried to pull away. Jean, anticipating his
reaction, fell forward, using her weight and position to overpower his
attempts to escape. Firmly holding him down, she seductively whispered
in his ear.
"Tammi, all women suffer pain the first time their cunnies are
violated. It's part of being a woman. Just relax and the pain will go
away. Be thankful I care for you, most girls are less lubricated their
first time and suffer more than you."
As the pain was already beginning to subside, Tammi relaxed even more
and was reassured when the pain was replaced by a pleasant full
feeling. Jean, aware of his condition, slowly began to inch more and
more of the rubber phallus inside him. When she had all eight inches
up his "pussy" she began fucking him in earnest.
"Reach under yourself and stroke your "clitty", sweetie. When you get
ready to come, stop and let me know."
Tammi felt the passions building in his groin. Closing his eyes, she
imagined she was on a date in the back seat of a car. She had allowed
the boy to get her overly excited, had lost total control of the
situation and was now being penetrated for the first time. The fact he
still wore the garterbelt and hose helped his imagination "picture" the
scene. Reacting to the fantasy, she began to push her "pussy" back to
meet her male lover. Tim had always wondered what it felt like to be
penetrated like a woman. Now he knew ... it was wonderful! Aware he
was quickly approaching orgasm, he opened his eyes and informed Jean.
"I'm about ready to come!"
Jean gave one more inward stroke, then pulled the dildo out with a loud
sucking sound. Flipping Tammi on her back, she raised his nylon clad
legs high into the air and reinserted the dildo in Tammi's "cunt".
Spitting into her hand, she reach forward and grasped Tammi's swinging
cock, encircling the crown between her middle finger and thumb. Then
matching the thrusts of her hips to the twisting motion of her hand,
she pounded Tammi's pussy with her false cock while she jerked him off.
The sensations "rolled" between Tammi's cock and "pussy". She felt the
inner muscles of her "cunt" grasping at the dildo with each outward
stroke, trying to keep it from leaving and then spreading wide to meet
the "boy's" hardness as it again forced entrance into the channel of
her womanhood. No longer wishing to hold back ... Tammi came. Her
cum exploding in graceful arcs landing on both their bodies. Some even
splattered their faces. Jean also achieved orgasm brought about by the
direct pressure of trusting the dildo into her "lesbian" lover's
"pussy". Exhausted, she pulled out and fell across her newfound lover.
Reaching their moist lips to each other, they gently "kissed" and
licked the spent juices from each other's features, giggling as young
girls are prone to do when they have a secret.
"Now you know how it feels to be a woman! Did you like it?"
"Oh, it was wonderful, everything I fantasized it would be! But it was
only 'good' because it was you taking my 'cherry'! Jean, I love you!
I wish I could be your lesbian lover and live with you all the time!"
Jean thought a moment, then said.
"After we see how it goes when your mother visits, maybe we can work
something like that out between us. I'd love to have a girlfriend like
you. Let me think about it. Now I think it's time we removed these
clothes, cleaned ourselves up, got into some sexy nighties and went to
sleep. We need some rest before my sons come home tomorrow."
They did exactly that, giggling and playing with each other as they
cleaned up. Cuddling up next to each other, like two spoons in a
drawer, they fell asleep. Somewhere in the middle of the night, Tim
awoke to the warm realization he was being fondled. Pretending he was
still asleep, he peeped between his lashes and found Jean was slowly
moving her hand across his panty covered ass. Deciding to "see" what
Jean was up to, he continued to feign sleep.
Jean had awakened, from a sensual dream and looked over at her young
lover's body. Remembering what had transpired earlier, she felt desire
again building within her. Realizing she still hadn't "taken" his male
virginity, nor had she been "fucked", she slid her hand to his satin
covered ass. Not knowing if he could perform yet, she rationalized he
could at least satisfy her again with his tongue. Moving her hand
under Tammi's baby dolls, teasingly up his stomach, she encountered his
nipple. Stroking the tip, she was again amazed how hard it became.
Lightly pinching it brought mewing sounds from the youth's lips.
Assuming he was still asleep, Jean pulled her hand from under the
nighty and gently slipped it under the elastic of his panties. Finding
his penis fully erect, Jean surmised Tim was faking. Delighted to find
him restored, she however, was not going to let Tim get away with his
deceit. Cupping her hand around his sack, she began to gently but
firmly squeeze his balls. She laughed as she spoke.
"When you decide to stop faking, beg me to release your jewels and
offer me something 'nice', I'll stop, but not before I get your
promise."
Not in any real pain, yet, he answered.
"If you let go of my nuts I'll promise to eat your pussy."
"Without my panties on?" She asked, exerting more pressure.
"Yes! Yes! Only stop your squeezing!"
Releasing him, Jean ordered him to remove his nighty and panties. As
he complied, she removed hers and stretched out across the bed with her
arms above her head. Bending her knees and letting them fall naturally
open, she exposed her total womanhood.0D
Tim lay down and positioned his head above her pussy. Placing his
hands under her tush he raised her pelvic area to his moist lips.
Gently kissing and licking her outer lips he used his tongue to open
the inner ones. Now darting his tongue into her cunt, he "flicked" the
inner walls.
"Oh! Oh! Yes! Fuck my pussy. Stick that hard tongue all the way
inside. Oh, that feels good! Don't stop!"
Tim "bounced" his head between her open lips, mashing his nose against
her clit. When he felt her thighs quivering against his ears ... he
did stop. Letting Jean's desires coast to where she could catch her
breath, he again moved his face up to her oozing cunni. Using his
fingers to hold her open, he teased the blood engorged bud of her
clitoris with his tongue. Kissing and licking, in teasing circles, he
felt the muscles of her legs again tighten. Increasing the flicks
caused Jean to throw her legs up over his shoulders, locking her ankles
behind his head and thrusting her hips upward to meet him.
"Yes! There! Yes, there! Faster, oh yes, there and there! Now
harder. Harder! Yes! Yes! Oh! I'm coming! AAAAAAIIIIEEEEEE!"
Jean came and came and came. The burning sensation raced through every
erogenous nerve ending. Her arms flailed the bed as her head trashed
from side to side. She squeezed her thighs so hard, Tim almost passed
out. When the painlike throbs finally stopped running amok, she
collapsed. Tim watched as she slithered and rubbed herself against the
sheets in an effort to "milk" every last tactile sensation from her
body. Lying beside her, he gently "munched" and kissed her lips, cheek
and the tip of her nose until she was able to speak.
"I've never experienced an orgasm so strong. It's never been that good
for me! I'm a little embarrassed by my performance. Oh, but thank
you, it was wonderful."
Tim, leaning on one elbow, smiled, then bending down, he kissed her. A
kiss of love ... not passion. Jean recognized the kiss for what it
was, threw her arms around his neck and returned his love.
"I woke up with the intention of making love to you. Instead you
satisfied me. I should spank your ass for feigning sleep, but the way
I feel, I just don't have the energy"
"Does that mean your too tired to make love?" He asked forlornly.
"Aha! I got you. How does it feel to be tricked by your lover?" She
laughingly asked.
"You mean we can?" His voice rising.
"Yes, of course we can. Women don't need to regenerate like men do.
All we need is a few moments to let our emotions return to normal.
Let's go get something to drink and a cigarette and then we'll see what
happens."
Each slipped on their night gowns and a pair of fuzzy high-heeled mules
and then Tim followed Jean downstairs to the kitchen. Opening two cans
of diet coke, Jean put them on the table and sat down on Tim's lap.
Squirming her bottom against his limp penis and throwing one arm around
him she teased his earlobe between her lips.
"Aren't you glad you offered to be my kids baby-sitter?" She laughed.
Tim slipped his hand under her top and cupped her heavy breasts. Jean
warned him not to play too seriously or she would never make it up the
stairs. She realized the unique attraction her breasts were to the
youth. When she felt he had played enough, she slipped off his lap and
sat on one of the kitchen chairs. Lighting a cigarette, she spent the
next 30 minutes asking him additional questions about himself and his
mother.
Putting out her second cigarette, she stood up, took his hands in hers
and pulled him up against her lush body.
"Tim, darling, why don't you take me to your room and fuck me! I want
to feel that huge cock of yours pounding inside my cunt."
Realizing the tack she wanted him to take, he said.
"Not before you suck my dick!"
Squealing in false terror, she broke out of his grasp and ran up the
stairs, with Tim close behind. He caught her halfway up, raised her
nighty and playfully "smacked" her across her panty-clad bottom. Her
false scream of protest earned her a second swat, this one just a bit
harder. Running to get away from a third, she stopped at the doorway
to her room, paused, pulled down her panties and "flounced" her naked
ass. Before he could react, she ran and jumped onto the still warm
bed. Stripping naked as he climbed the remaining stairs, Tim entered
the room ... as a male.
Jean took one look at the dick in his hand, scooted over to the edge of
the bed and began to draw it into her warm, wet mouth. She could tell
it wouldn't take very long to get the youth primed. His legs were
already shaking with desire as she swirled her tongue over and around
his male organ. When he began to thrust forward as if fucking her
mouth, she stopped and fell spread-eagled across the bed.
"You need to calm down a bit. Eat me again. It will get me slippery
wet. That way you'll be able to enter me easier and last longer."
Within three minutes Jean was herself too aroused from his cuntlapping
to wait. Pulling his face from between her outstretched thighs, she
dragged him on top and guided his dick inside her demanding cunt. The
warm, wet walls of her womanhood enveloped his young manhood. Nothing
he had ever experienced before this moment had prepared him for the
sensation of being inside a woman. Not wanting the feelings coursing
through his groin to ever stop, he lay there without movement.
Jean, surprisingly ready again, understood his lack of movement, but
would not be denied and took matters into her "hands". She ever so
slowly backed her pelvis away from Tim, drawing his cock almost all the
way out of her tunnel of desire. A strong shudder racked her lover's
body. She whispered.
"Don't hold back, I'm as ready as you are, go for it."
Tim thrust forward with the power of a piston. Slamming his balls
against her ass, crying out in a mixture of sensual pain and abject
pleasure. Pulling back, then thrusting again, he was met by Jean's
upward stroke. No longer in control, they both went into a frenzy of
stroke and counterstroke. Tim, his need that much greater, came first!
Flooding her womb with cannonades of hot cum. As the first shot
exploded against the slick walls of her pussy and his throbbing penis
"fired" a second shot, she also climaxed. Muffling her screams of
ecstasy into his shoulder, she continued her pelvic thrusts and using
her inner muscles ... drained him.
Afterwards, turning her back to him, she drew his arms around her
shoulders. Cuddling into his warmth, she told him how she had felt,
what sensations she had experienced and asked what and how he had felt.
After some mutual "love words", they fell asleep, cradled in each
other's loving arms.
The next three weeks went quickly. They made an effort to see each
other during the school day, but, in order not to raise suspicions, he
"baby-sat" only one time. On that one occasion, after Jean's sons went
to sleep, she and Tim retired to her bedroom where they changed Tim
into Tammi. Jean surprised her lover with a complete new outfit in
better fitting sizes. They spent the entire night, dressing Tammi,
teaching advanced makeup concepts, practicing his feminine traits and
mannerism and making "girl-love".
During this time, Tim called his mother. He found out she was
definitely interested in attending the "Tea" and looked forward to
meeting his newfound friend, Jean. Over the phone, "mom" sounded
different. When he questioned her, she hinted she had a surprise for
him, but wouldn't tell what it was until they got together.
Jean explained to the administration that Tim had told his mother about
his "baby-sitting". His mother had called and wanted to meet her.
Jean had invited her to spend the weekend at her house and asked if Tim
could also stay over. The Commandant thought it was an excellent idea
and gave his permission for Tim to "check out" after classes. That
Friday, Tim hung around till Jean got off work and the two drove to the
train station to pickup "mom".
The beautiful woman who got off the train looked very little like his
mother. Even when she dressed up, she had looked average. That's not
to say she wasn't basically pretty. Mom had always been slightly
overweight, seldom wore makeup, always pulled her hair into a
conservative bun, wore thick glasses and clothes long out of style.
The "new" mom was a major improvement. Immediately Tim noticed the
change. Rita had cut and frosted her hair. Her new style was much
shorter and swept around over her ears, making her look younger. The
glasses had been replaced with contacts. She was wearing make-up!
This highlighted her features, thereby helping her appearance. She had
lost weight and no longer looked "puffy". Another change was her
clothing. Mom had always "dressed down". The "new" mom striding
towards them was wearing the height of fashion. Rita wore a navy,
double-breasted coat dress with six large white buttons across the
front. The white lapels crossed just below the upper "swell" of her
breasts. The hem was actually above her knees. Her hose were matching
navy and very sheer. She wore 3 inch, navy and white spectator heels.
The most startling change, however, was her carriage! She had always
walked with her shoulders slumped, seldom wore a smile and always
looked a little bit lost. Now, her head held high, her shoulders back,
her face lit by a flirting smile and with a mischievous twinkle in her
eyes, she strode toward them with purpose in her step. The effect was
wonderful to watch, she was stunning ... and she knew it.
Tim ran to her arms and kissed her, all the while noting the jealous
looks he received from the other male onlookers.
"Wow, mom, You look great!"
"Well thank you, dear. I hoped you'd like the new me. Now don't
forget your manners, please introduce me to the lovely young woman
standing behind you."
"Mom, this is my friend Mrs. Jean Kinzie. Jean, this is my mother,
Mrs. Rita Wayne."
The introductions were made, hugs exchanged, both women agreeing to be
called by their first names. Tim retrieved Rita's baggage and the
three headed for the car. When he assisted Jean into the car, she
purposely allowed him to see up her skirt. This was not lost on his
mother. When Tim came around the car and assisted his mother's entry,
she allowed her skirt to flair open so both Jean and her son caught
more than "a glimpse of stocking". As Tim climbed in back, both women
turned to the other and smiled knowingly at each other. On the way, as
they waited at a stop-light Jean, turned to Rita. Running her eyes
over the woman's lush body and licking her lips, she informed Rita that
her two sons would be staying at her sister's for the weekend and they
would be able to "enjoy" their weekend without any other
responsibilities. Upon hearing Jeans statement, Tim's mother stretched
her hand to Jean's exposed thigh, squeezed the inner flesh and winked
her understanding. Both women spent the drive-time in disguised female
conversation. Using chit-chat to hide their true questions and
responses from the unsuspecting youth. Tim sat quietly in back,
offering responses only when asked a direct question. Not being as
worldly, he nervously wondered what his mother's reaction would be to
Jean and he being lovers. Unbeknownst to him, the women had already
communicated and reached an understanding. As the car pulled into the
garage, she asked.
"Rita, would you like to 'freshen up' a bit or would a drink be in
order?"
Rita answered, "Why don't we relax over a drink or two. We have 'so'
much to talk about, I'm sure."
Entering the house, Jean gave Rita the "two dollar" tour, with the
usual pleasantries exchanging between them. As they entered the den,
Jean suggested that Tim take Rita's bag to the master bedroom and hang
out his mother's clothes. As he moved to comply, Jean, momentarily
guided Tim out of his mother's hearing and told him to change into
Tammi.
"Everything is going as planned. Wait upstairs for my call."
Fixing two drinks, she reentered the den and sat at the opposite end of
the couch from Rita. Before she could say a word, Rita spoke.
"Your a very attractive young woman, I can certainly see why my son is
infatuated with you. I assume, there is no "Mother's Tea" and you sent
the invitation so I would be your houseguest for the weekend. After
meeting you, I'm truly glad you did. I'm guessing, but I'd be willing
to bet that your aware of Tim's "special" needs where it concerns
clothing. Jean, why don't we both speak openly and see where it takes
us. As you probably know quite a bit about me, why don't you start,
afterall, this was your idea."
Jean held back nothing. She explained how she had foolishly gotten
pregnant at sixteen, married, had a second son eighteen months later,
her divorce, how she met Tim and the feelings he stirred in her. She
detailed the trap she set for Tim and how she caught him dressed in her
clothes. She explained how her initial plan had changed and how she
then had introduced him to both hetero and lesbian sex. Jean admitted
the "tea" was only an excuse to get Rita to visit, just as Rita had
surmised.
Rita listened attentively and asked questions when she desired further
details. When the story was finished, she slid over to Jean, took her
in her arms and kissed Jean ... thanking her for helping her son.
Then parting Jean's lips with her tongue, she kissed her again this
time with a lover's passion. Surprised, at the second kiss, Jean
returned it with equal fervor. Finally, they broke apart and Rita
spoke.0D
"I think, before you and I go any further, we should bring Tim down, I
have some "news" that will be of interest to both of you."
Walking to the stairs, Jean called out.
"Oh, Tammi, would you please come downstairs and join us."
Tim had taken the suitcase upstairs to Jean's room as he had been
directed. Placing it on the bed, he snapped the latches and lifted the
lid. His eyes were immediately drawn to the dildo lying atop a
beautiful peignoir set.
"What's happened to mom? If I didn't know better, I'd say she's an
impostor. She's never wears clothes like those she wearing today and
she's never had a dildo. I can't wait to find out what caused the
change. I also can't wait to hear about her surprise."
Taking each succeeding garment from the bag, he hung Rita's clothes as
he had been directed. As he lifted the last dress he discovered his
mother's lingerie. Where he had been surprised before, now he was
amazed. The panties, bras, teddies, nylons and garterbelts were of the
type he had seen advertised in the girlie magazines she use to give
him. The bras and panties all matched, were almost seethrough, ranged
through the color spectrum and many still had price tags attached. One
pair of panties, he noticed, were even "crotchless". What had changed
his mother so drastically, he wondered. Realizing he might be called
downstairs at any moment, he hurriedly finished emptying the suitcase
and began his transformation into Tammi. He had just finished when he
heard Jean's call. Taking a last look in the mirror and pleased with
the reflection, he went to join the women. Entering the den, he
immediately saw the surprised look of approval in Rita's eyes.
"Oh Tammi, you look lovely!" She exclaimed.
Turning to Jean, she said.
"Jean, you've done wonderful things with her makeup and hairstyle. I
can't believe how much more feminine she looks. This is going to make
my surprise even more exciting!"
Jean interrupted, "Tammi, come sit between us so your mother may tell
you her surprise."
Rita waited till all three adjusted their skirts and then began.
"Jean and I have just had a wonderful conversation, explaining all that
has occurred between you two. First of all, let me tell you I'm very
happy for you both. If I had "picked" a woman to teach him, I couldn't
have made a better choice! Jean, I sense the love between you and I
understand your bisexuality. I, myself, have always had a yearning to
make love to another woman. As you did, I've kept it hidden, but after
meeting you, I think that's about to change!"0D
Jean spoke as she squeezed Rita's hand in acknowledgment. "That's one
of the desires we can remedy together! The desire I can't change is
I'm sorry I've never had a daughter. I love both my sons, but wish I
had a young daughter who could share my joy of being female."
"Well, maybe my surprise can help you rectify that situation.
Actually, I have a whole bunch of surprises! The first of which is:
Tim, I'm in the process of divorcing your father. I know you have
questions, but let me explain everything and then I'll answer any
questions either of you have."
Both Jean and Tim nodded their heads in agreement.
"As I said, I'm divorcing my husband. I came home early from work one
afternoon and found him in bed with another woman. I was smart enough
to take pictures of the two of them. He, nor she, are in a position to
contest the divorce proceedings. He's moved out and I suppose she'll
marry him when the divorce is final."
Tim interrupted. "Mom, he's no loss!"
Nodding her head in agreement, Rita continued.
"The second surprise is I've inherited a large mansion, an equally
large sum of money and an import company in the San Francisco area from
my uncle, John. Tim, you've never met Uncle John, he left Ohio when I
was very young. The rumors were he was gay and the family didn't want
anything to do with him. As I understand it, he went to California and
made a fortune. The will states that the only member of the family he
ever liked was his little niece ... me. I barely remember him, but he
obviously remembered me. The third surprise is, I'm taking you out of
school and we're moving to California where I'm going to run the
company with the help of Uncle John's lawyer. The surprise is that
you'll be moving out there as Tammi! I've discussed your situation
with him and he has assured me that you'll have no problems. The
lifestyles of San Francisco are better suited for your needs. Before
you two start crying over losing each other, let me finish. Jean, I've
done some checking and find that your most definitely overqualified for
your current job. I'll be needing a female secretary/companion who
would live and work at the mansion. That person will share my new
lifestyle because of my need to work closely with her. I'd like that
to be you. I imagine you and I would enjoy working "very" close with,
both 'day and night'. I'm sure you understand my meaning. You'd have
your own set of rooms, an excellent salary and a nanny to watch over
your boys when you were at work or possibly involved in "social
interaction" with me. That would obviously leave you the time to
further "train" Tammi. Speaking of sons, as yours are so young, I'm
sure their memory of Tim will quickly fade and in time, be replaced by
their adopted sister, Sarah. Well that's it, any questions?"
Both Jean and Tammi had questions. Many of them the same. Concerns
were voiced, alternatives were discussed and plans made. However,
within a relatively short time they where all in agreement and Jean
accepted the position as Rita's live-in secretary/companion, Tammi's
tutor and anything else that might develop between the women.
Rita and her son's fantasies had both been fulfilled. She threw her
arms around her son, still dressed in his feminine attire and hugged
him to her breasts. Kissing and cuddling him in her arms, she told him
how much she loved him. All three "women" began to cry, tears of joy.
Rita, reaching an arm out, coaxed Jean into joining their hug. There
they remained, locked in each other's arms, the three "women" dreaming
of their future lives together.
(c) 1996 Kresha Matay