MILITARY SCHOOL CROSSDRESSER
By Kresha Matay
PART 1
Tim was a sensitive young boy, bright and intelligent, but lacking many of
the physical characteristics of Joe, his father. 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 couldn't 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 ridicule 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 only child,
transferred her love from the husband to the son and viceversa. 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 that 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 have 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, the youth 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 were 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. Afterall, 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
dressup 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
pantygirdle, nightgowns, breast inserts, panties, slips, nylons, bras,
pantyhose, garterbelts, costume jewelry, makeup and even a long tressed
blonde wig. These were kept in her clothescloset (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 encourage 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, and
gentler voice, becoming 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 outofdoors, 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, makeup 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? as they got.
Theirs was not a sexual situation, but one of love and understanding.
PART 2
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. Joe 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 wellbred 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 other 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 twentytwo. 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 sexier (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 they're 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 peasant 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 "rattatattat"
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, legtrashing climax. The most
powerful climax of her twentytwo 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 fourfoot 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 passionfilled 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 thickens and then
push its 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 trobbing 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 hardon 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
lockerroom to bring himself to orgasm, all the time remembering what he had
seen.
PART 3
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 ongoing problem of finding a qualified sitter
and asked her boss if she could avail herself of Tim's services on a
semiregular 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 babysit 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 lowcut 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 you're 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. Most 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 you're 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 older, 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 youth's 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, she closed the door, and drove off.
Watching her drive away, all he could think was "WOW, what a sexy
woman!"
PART 4
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 earlier 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, and 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's. 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 nightgowns.
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 neighbor'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
jackedoff. 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 walkin 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 expertly adjusted the straps for
a better fit. Stepping into the matching emerald green satinlike panties, he
slithered them up his legs, past the garters and shimmied his ass into the
delightfully cool material. Pausing to accommodate his semiturgid 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 deep inside herself, she used her other hand to masturbate the
bloodengorged bud of her clit. Mentally she warned herself against losing
control or emitting any sound of passion that might cause her to be
discovered. Her mind reeling from the sensuousness of what was being
enacted before her eyes she 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. He realized, Jean's lingerie was even more satisfying
than his mom's was. Also, dressing in the clothes of a woman who was a
stranger increased the sensuousness he felt.
Turning, he noticed 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 also his
crossdressing would be exposed to his father. Knowing his father's
punishment would certainly be painful, he also 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, you're 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, you're 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 you're 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 dressup
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 "girltalk". 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 pantycovered 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
pantycovered 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 seethrough 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. Jean had selected Tim's mother
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 encouraged 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 his mother received this 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 hardon, 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 jaw 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 "Frenchkissed" 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 strapon
dildo she had hidden there. She had purchased it, just recently, in the hope
that the dildoe's size would resolve her masturbation problem. While she
hadn't really needed the strapon 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. "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
felt a cock inside your 'pussy'!"
Immediately guessing what Jean had in mind and in fear of the dildoes 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 semihard. Jean told him to relax
his sphincter muscle and he found the finger fucking even more pleasant.
When Jean felt he was fully primed she positioned the dildoes 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 nylonclad legs
high into the air and reinserted the dildo in Tammi's "cunt". Spitting into her
hand, she reached 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.
PART 5
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.
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
J