textfiles/sex/EROTICA/J/jacqui.txt

Jacqui
author unknown

******

     John and his wife had gone to a party at the home of
Barbara, one of their friends. Barbara was tall and statuesque. A
very striking divorcee who gave every indication of being eager
for sexual activity. John had met her before his marriage at a
time when his finance was living in another city. Barbara had
come on strong at the time, but John hadn't responded.

     The party had gone on for several hours and most people had
left when John went upstairs to use the head. As was his habit,
he quickly checked for evidence of stray feminine undergarments
which he might fondle. None were in immediate evidence so he
stepped into the bedroom and slipped open a drawer. John had done
this routine sufficiently often so that he had a sixth sense for
the location of the lingerie.

     He was rewarded by the sight of satin and nylon in a
profusion of colors and styles. As he had suspected, this was a
woman who pampered herself with a delicate selection of panties
and bras. As John had surmised from hugging Barbara whenever they
met, (this was always an opportunity to make a cursory check of
the type bra being worn). There was a selection of front and
backhook bras.  Most were very flimsy and delicate and there also
were many with underwires to support her luscious breasts when
she did not want them to jiggles.  Some were demibra styles for
wear with cleaving decolletage.  Even better, they were 36-C
which meant that they would be a perfect fit for Jacqui.

     While the temptation to linger over this find was strong,
John was emboldened to try another drawer.  Again, his desires
were realized when he found lacy slips and several garterbelts
with real nylon stockings among the pantyhose. Needless to say,
John was rapidily transported into ecstasy as he began to
contemplate playing Jacqui with this treasure trove.

     Unfortunately, his preoccupation was so complete that he
failed to hear footsteps coming up the stairs and into the room.
His first clue was when he heard Barbara's husky tone saying,
"Well, can I infer that you prefer my lingerie to me? This will
interest your wife and our friends."

     John could only throw himself on Barbara's mercy, explaining
about Jacqui and begging her not to disclose his secret yearning
for feminine garments. "Very well she replied", indicating her
long held contempt for all men which derived from her former
husband's behavior in leaving her for a much younger woman. "I
have always wanted a sissy male to serve me and you should fit
the bill nicely. I will make you sorry that you intruded into my
privacy and you can expect ample humiliation to be coming your
way. I won't share this with your wife for now, but if you don't
follow my instructions, you can bet your pantyclad ass she will
find out about you quickly."

     "Tell your wife that you must work next Saturday and be here
at 9 a.m.  Wear your bra and pink satin panties and be sure to
bring along a waist cincher, garter belt, stockings, heels and a
butt plug. I will begin your training as a humiliated sissy
shemale. Don't ever expect the pleasure of wearing my feminine
finery, although I may allow you to earn the privilege of
worshipping it as a symbol of my superior body and your weakness.

     Needless to say, John thought of Saturday with both fear and
anticipation, knowing that he could indulge his love of lingerie,
while at the same time he could be humiliated by this striking
creature as she feminized him still further.

     Getting out of the house already wearing his bra and panties
was a problem because the bra was clearly visible through his
shirt. However, he quickly got to his car without being seen by
the neighbors. On the other end, he was not so lucky as he had to
walk a distance. Of course he encountered a group of teenaged
girls who were chatting and giggling with youthful exuberance. He
could not avoid them and although it made him nervous he wanted
to see the outlines of their brassieres, even though doing so
increased his risk of exposure. How he envied their developing
breasts, swelling inside lovely lacy bras.

     Barbara greeted John by demanding that he demonstrate that
he was wearing a bra and panties before she would let him enter
her house. Although John was certain that the teenaged girls
could be observing him, along with whoever else might be
watching, he had no choice. He carefully raised the front of his
shirt, trying to keep the back in place until Barbara could see
the nylon and lace cups of his flimsy beige bra held snugly in
place with y-straps.

     Far from being satisfied, her only comment was, "And what
else are you wearing? I want to see your pink little panties,
now." John fumbled with his fly, but was informed that he was to
open his belt and lower his trousers before he would be allowed
the safety of having the door closed behind him. He could only
comply.

     Once she had him inside, Barbara instructed John to remove
all of his masculine clothing which she then locked away in a
trunk. Tying his hands behind him, she demanded that he present
himself kneeling before her to pledge obedience to her superior
female titties and pussy. She demeaned his pathetic little
nipples and clitty-cock, reminding him that they were not worthy
of the nylon and lace lingerie that he so coveted. However,she
promised, in return for his devotion, to work on improving his
worthiness.

     John was then blind-folded and required to stand clad, only
in bra, panties and heels, without moving until Barbara returned.
After a few minutes, she returned to the room. To John's surprise
she began to rub and squeeze his nipples. The effect on his cock
was immediate. " Shall I take your panties down? 'Oh yes' "Yes is
not acceptable, you will never address me except as 'Mistress'.
"Yes Mistress, please." John felt the panties being slipped down
to his knees.=20

     Next he felt something being tied around his erect cock.
When the blindfold was removed he saw a pink bow decorating his
cock. Almost immediately there was a flash and he realized that
Barbara had taken his picture. His erection quickly
disappeared. "That, she announced, is for documentation of your
journey and as further insurance of your continued obedience to
my commands."

     Pulling his panties up tightly wedged into the crack of his
ass, Barbara untied Jacqui's hands and directed him to don the
rest of his feminine attire. With trembling anticipation, Jacqui
inserted rice-filled nylon bags into the cups of her 36-C
brassiere, carefully adjusting the straps. The beige bra had been
replaced with a black underwire with satin cups to cover the bra
forms.  Jacqui would have preferred a demi-bra, but pushup
styles don't work well for shemales with pretend titties.

     He often wore less sturdy bras which allowed his pretend
titties to jiggle, but had decided that this was likely to be a
situation requiring some restraint, especially if Mistress
Barbara wanted to have him remove the bra forms so that she could
administer nipple punishment (which, of course, Jacqui fervently
hoped would be the case).

     After requesting permission to remove the pink panties which
Mistress Barbara had pulled up to cover his clitty-cock, Jacqui
next forced himself into the black waist cincher to flatten his
tummy and to shape his hips. He then fastened the red nylon
garterbelt around his waist. Sitting on a stool, he drew each of
his black nylons up his legs, attaching them carefully to the
garters. In front, the garters stretched tauntly down his thighs,
framing his pubic hair and flaccid cock. The back two suspenders
curved over his buns. Jacqui then stepped into black leather
pumps with three inch heels.

     Finally, before pulling up her snug satin panties, Jacqui
squatted down and inserted a gob of K-Y jelly, followed by a butt
plug into her puckered little asshole. Squeezing her buns
together to retain the buttplug, she stood and pulled her panties
snugly over her buns. While the panties would help to hold her
plug in place, Jacqui knew that she would have to keep her anal
sphincter muscles tightly clasped around the plug and that doing
so would remind her to maintain a more feminine posture.

     When Jacqui had completed that task, she pulled on a short
black half-slip which barely covered the tops of her stocking as
she stood uncomfortably before Mistress Barbara, not knowing what
was next. Jacqui hoped that her clitty-cock would behave and
remain in a flaccid state. But, she knew that eventually it would
demand attention and Jacqui was apprehensive about her Mistress'
reaction.

                            CHAPTER 2


Well," Barbara chuckled, "I can't decide whether you look
ridiculous, pathetic or cute." "I suppose you are a bit of each.
Perhaps some make-up would improve your appearance, but I think
that will have to wait until you earn it by taking care of my
needs."

     "Now that you are all dressed-up, we'll go outside so I can
use the remainder of this film in natural light. We do want to
have an adequate record of your progress." John was terrified
because although he knew that the backyard was fenced, it was
visible from the upstairs windows of adjoining houses. His terror
was heightened when they got outside and he could hear voices
from the next yard. But, he also knew that he had no choice but
to cooperate.

     "If you want to pretend that you are a woman, I'll want to
see that your posture and gait are feminine. I don't want you to
be an embarassment to we genetic girls who have real titties to
jiggle when we walk and long shapely legs with well rounded buns
for men to covet. Put some sway into your walk so I can decide
whether you are sexy enough to excite my lesbian friends. Then
perhaps we'll see whether horny men notice you when I put you on
public display."

     Jaqui, of course, had often practiced walking in heels. She
loved the feel of tension in her calves when walking in heels,
and adored the taut garters snugly holding her stockings to her
thighs. When Jacqui walked, the butt plug wiggled, requiring
strict attention to maintaining a tight grip with her pretend
pussy. And,she had to keep her thighs tightly clasped to hold his
clitty-cock and scrotum tucked away so that they would not create
an unsightly bulge in Jacqui's panties. The result was short,
mincing steps which displayed an exaggerated femininity, and
provided a delicate bounce to Jacqui's pretend titties.

     "Well," declared Barbara, "even though you walk like
something is sticking up your ass, the effect isn't bad. Training
you may not take as long as I anticipated. If I allow you to
remove your butt plug, will you still be able to stand and walk
like a sissy male doing an imitation of a real woman?" "Yes,
Mistress," Jacqui replied.  "Very well, you may remove it, but
don't think that I'm finished with your little rosebud. If you
want to have a pretend pussy, I'm going to have to stretch your
little hole so it can accomodate my largest dildo."

     "First, I want some more pictures. Sit demurely with your
ankles crossed. Now, cross your hands across your breasts as
though you were shielding them from prying male eyes trying to
undress you. Lift your slip so I can capture your garter tabs and
your bulging mound which is pretending to be labia. Now turn
around and bend down so we can see your panty covered ass."

     "Now trot inside, remove your plug before you get too
excited and get yourself back here to me. If there is any
evidence that you have relapsed and done naughty little boy
things to your pathetic excuse for a pecker while you are out of
my sight, you will be severely punished and our game will be
over. I have more plans for you and they do not include your
sexual gratification except under my control."

     Keeping her tightly puckered asshole clasped around the
buttplug, Jacqui teetered across the patio and quickly went to
Barbara's powder room. Lowering her satin panties, and delicately
lifting her slip, Jacqui expelled the buttplug, carefully wiping
her asshole so that no lubricant dripping from her shemale pussy
would stain her panties. She then pulled the panties snugly up
into her crotch so that her clitty-cock would be held tightly out
of sight and her scotal sac with its unfeminine balls retracted
up into where her pussy would be if only she had one.

     Jacqui then washed her smelly plug with hot water and soap
and put it aside, wondering what was next in store. Jacqui didn't
have long to wait as Barbara immediately summoned her with a
brusque reminder that a Mistress must never be kept waiting.

     "You really are a titless, pussyless wimp who needs to be
chastized both for keeping me waiting, and for having the
audacity to pretend that you have breasts and a vagina as though
you were a real woman. You aren't anything but a flat chested
sissy shemale. Take that padding out of your bra and get on your
knees in front of me. I'll see if you can get erect nippples just
as we ladies are expected to have when a man fondles us."

     Jacqui immediately kneeled in front of Barbara who was
seated in a lounge chair with her legs slightly spread and her
miniskirt hiked up to mid-thigh. Her creamy white thighs were
visible beyond the exposed tabs of her garters. She was wearing a
gauze-like blouse through which the outline of her sheer lacy bra
and the brown circles of her nipples were noticeable.

     "All little boys believe that girls titties grow from being
fondled and mauled. Do you believe that I can make your titties
grow by playing with them?" "Oh yes, Mistress, please do",
replied an ecstatic Jacqui. "You really are a foolish twit,"
replied the haughty Barbara. "You could't fill that bra even if
you overdosed with hormones. What I will do is to make those
nipples so sensitive that you will know how it is for a woman
when her breasts are tender and distended because of the time of
the month and some pig of a man has mauled them thinking that it
felt good for her. "

     "I know that is what you want, but first you must get me in
the mood. You can start by licking my thighs, above my stockings,
until you have your nose buried in my pubic hair and your tongue
is licking my clitty. If you can keep your hands to yourself, and
away from yourself, you will be allowed to suck my pussy for as
long as I enjoy it. If you can get me hot enough so that my
nipples push against my bra, I'll work on your pathetic titties
until you beg me to fuck your sissy shemale ass. Now get
started."

     Jacqui was, of course, delighted at this opportunity to
serve her Mistress who already had Jacqui in an absolute state of
internal arousal and fighting hard to keep the excitement from
causing her clitty to become noticeably tumescent. She quickly
began licking the inner aspect of Barbara's thighs. It was no
time at all before Jacqui's nose and lips were nuzzling Barbara's
labia and tasting the moist nectar inside of her cunt.=20

     Jacqui knew, that in spite of Barbara's seeming
indifference, she was becoming aroused too. Not only was
Barbara's pussy getting more and more moist, but Jacqui could
sense the muscular quivers anticipatory to orgasm in a woman
whose cunt was throbbing from the attention it was receiving.
There were some telltale moans, as well.

     Suddenly, however, Jacqui's head was pushed away from that
delectable pulsing cunt so that her tongue was just out of reach
of those luscious labia, and she was gripped between Barbara's
powerful thighs. Simultaneously, Jacqui felt Barbara's long
fingernails probing through the satiny fabric of her bra, raking
across Jacqui's nipples. "Now, you sissy bitch," breathed
Barbara, "you are about to experience the exquisite torment of
nipple punishment and pleasure."

     With that, Barbara pinched and rubbed Jacqui's nipples until
the shemale was aroused almost beyond tolerance. Both Barbara and
Jacqui were wracked with great orgasmic convulsions as wave after
wave of release swept over them.  The pressure of Barbara's
thighs, the taste of her pussy on Jacqui's lips, the stimulation
of her nipples, and the gentle friction of stockings and panties
caressing her genitals were causing Jacqui to cum in the satiny
panties even though no one had touched her clitty-cock.=20

     She could feel the sticky exudate collecting in her crotch.
It was warm and wonderful, and Jacqui knew she would still be
horny after her satin panties had turned damp and sticky.

     As they both lay exhausted, Barbara reclined in her chair
and Jacqui kneeled on the ground awaiting further instruction
from her Mistress. Barbara informed Jacqui that while she had
made a good start, it would be necessary for Jacqui to exercise
bettter self control during future sessions. "You may leave now.
Change into the bra you wore when you arrived, but leave those
panties on so that you will be reminded of how a woman feels when
some man's cum is dripping from her cunt after she has been
fucked. And, be back here at 9 next Saturday. I'll have some new
adventures for us. You know the rules so dress accordingly."


     "You also have an assignment. I expect you to spend at least
one hour a day with that plug inserted deeply into your virgin
asshole. I want it to be well dilated next week for you to feel
what it is like to be be on the receiving end of a hard prick, or
to wear a tampon as genetic girls must."=20
=20
     I alsoo expect you to be wearing a training bra. You don't
deserve the luxury of satin cups, a firm underwire and delicate
lace.  I saw you admiring those teenage girls outside and I just
know you were thinking about their cute little bras and panties.
I'll bet you were wishing that your titties were growing just
like theirs. Perhaps I should invite them in to show them how
ridiculous you pathetic men are. They should be learning how to
appreciate their soft downy pussies and tender young titties
which are superior in every way to male bodies."

     "I am going to give you more nipple training. Your pathetic
pretend titties certainly need it. And one other thing, except
for a sanitary belt and napkin to keep your butt plug in place,
you are forbidden to wear any lingerie until you dress to come
here next week. I don't want you getting aroused and wasting your
cum. I have plans for every drop that you can store between now
and your next training session."

     "Oh Mistress," pleaded Jacqui, "please don't make me wear my
bra when I leave here. I will wear my cum filled panties, but how
can I get into the house wearing a bra without Mimi detecting
it?"

     "You should have thought about that before you went
rummaging into my underwear and agreed to have me give you
petticoat training, you pathetic pussy. You should be pleased
that I am permitting you to wear it for a few more minutes.
Remember, its going to be a long week before you are to be
allowed the pleasure of a bra with the feeling of nylon and lace
around your tiny nipple-buds, and that will be only a flimsy teen
bra and not an exquisite creation of satin and lace which molds
and caresses the breasts and nipples of a real woman."

     "I will see you next week, and be prepared for more
petticoat training. I want those nipples and that hole ready."


                              CHAPTER 3

     Mimi had been asleep when John left the house that morning.
He could only hope, as he drove home, that she would be
distracted when he got home long enough for him to remove his bra
and cum filled panties.

     When he enterd the house, however, Mimi greated him with a
smile and a hug. "My," she whispered as she traced her finger
over the outline of his bra, "what is this?" Jake gasped and
replied, "I felt sorry that I had to leave you this morning so I
wanted to be thinking about your titties snuggled in your bra all
day since I didn't have an opportunity to fondle them this
morning."

     Pushing John away, Mimi said softly, "Dont lie to me you
sissy. You wore this bra all day because you wanted to pretend
you had luscious tits like mine. Now drop your trousers so that I
can see what you have under them. Have you been wearing my
panties again?"

     John knew she suspected something so he decided to respond
directly, "You know that I'm wearing the panties that you had
around your pussy and buns yesterday, dearest."

     "I want to see them," insisted Mimi. "I want to be certain
that you have't stretched them with a naughty erection."

     With great trepidation, not knowing how accepting Mimi would
be, John turned around and dropped his trousers so that Mimi
could see his buns but not the damp stain in his crotch. "Turn
around," Mimi demanded.

     When John didn't respond, Mimi slapped his ass with her
hand. "Barbara called me, and I know all about your day and what
led up to it. She and I have discussed your behavior and training
and I have decided to help her. I know that you have been wearing
my panties without permission and stretching my bras by wearing
them without my permission. I've found your cache of undies, your
heels, buttplug and fantasy articles. I want you dressed in your
sissy clothes now so that you can demonstrate what you have
learned and I can determine how best to continue your training."

     "It would be good punishment for you to follow Barbara's
orders and not wear lingerie for a week. But, we have discussed a
better arrangement. You will remain dressed as a sissy shemale,
including a plug up your ass and a sanitary napkin, at all times
in my presence. That way I can be sure that you are punished if
your clitty gets hard and you are tempted to play with it. If you
are not with me, you will wear male clothes, including baggy
cotton underpants."

    "Now," she continued, "take off those disgusting, soiled
panties and that bra. Go to the bathroom and shave your legs and
body including your balls. I want you to trim your pubic hair so
it is nice and feminine. When you have removed all the ugly
male=8Ahair that you can reach, I will inspect you and shave your
back."

     Even though he was uncertain as to where this would all
lead, John was excited and pleased, although hoping that his
clitty-cock would behave. At least he would be able to continue
to wear nylon panties and bras, even though he would have
preferred real brassieres to a skimpy training bra. John had also
long secretly fantasized about shaving his legs and trimming his
pubic hair. He looked forward to smooth legs so that he could try
stockings other that the dark ones he customarily wore to hide
his shapely but hairy legs.

     John quickly went to the bathroom, relieved that his secret
was in the open. Although he was somewhat apprehensive about the
future, he quickly decided that if he behaved, he could expect to
be treated as a female and would have two real women with
wonderful tits and pussys and a whole new supply of lingerie to
adore. He stepped into the shower and began his transformation.

     When he had finished shaving, including his face so that he
would be smooth all over, Jacqui (for he was now feeling very
feminine) shyly and demurely called to Mimi. She inspected him
carefully and pronounced her satisfaction. Reaching into the
vanity, she produced a large buttplug which she lubricated.

     "It's time we got you accustomed to the experience of having
an object inserted into your most intimate body cavity. Real
women spend almost 25 per cent of their time wearing a tampon and
are expected to accept male cocks at other times. Since you only
have one pathetic hole, it will have to serve both functions.
Until we can get you some tampons, a sanitary belt and pads to
chafe between your thighs, and a dildo for me to use on you, this
will do. Bend over so you can start to feel filled while I finish
shaving you."

     Jacqui obediently bent over, gratefully accepting the plug
into her (for she was now ecstatically into her female self)
puckered rosebud. She immediately and reflexively tightened her
anal muscles and squeezed the buttplug with her buns so that it
would remain in place. She then kneeled in the hard tub while
Mimi shaved the remaining hair from her back.

     "Now go to the bedroom and put on the pink panties and pink
training bra that you will find there. Put on the white shorts
and knit shirt and wear the low heeled shoes I have purchased for
you. Then we are going shopping to buy sanitary supplies for you
and a variety of dildoes for me to use in converting your tight
asshole into a usable cunt for Barbara and me to use at our
pleasure. We may find other uses for it as well."

    "But Mimi," cried Jaqui, "I can't go out that way. Everyone
will see the outline of my pink panties and bra, and what will
they think of a man wearing heels?"

     "In the first place," replied Mimi, "you will address me as
Mistress, because that is what I am. I do not intend to permit my
pussy-worshipping, sissy-slave to be on a first name basis with a
superior female person. Second, you have always enjoyed secretly
observing panty and bra outlines on real women. It is about time
that you were the object of lewd and rude stares from men and
women.

     "If I hear one more word of argument, you will have some
cute red polish for you fingernails and toes so that you will be
even more obvious as a sissy. To make certain that you receive
enough attention, you had better work at putting a seductive
wiggle in your ass when you walk. Barbara tells me that your are
skilled at wiggling your ass especially when your are busy trying
to retain your tampon. Now get going. I am impatient to get you
to the Mall where you can be seen."

     Under Mimi's watchful eye, Jacqui went to the bedroom where
she found the panties, bra and low heeled shoes laid out.
Although she was disappointed to see that the panties were cotton
rather than nylon, they were a feminine cut and their snug fit
carerresed Jacqui's buns. The bra was nylon. It didn't really
have defined cups, but only simple nylon triangles held together
with thin elastic bands which Jacqui knew would not be nearly as
enticing as the underwire bra with satin cups and a wide band
that she preferred. The silky nylon did rub gently against
Jacqui's nipples which were still erect and tender from Barbara's
earlier teasing.

     Mimi sensed Jacqui's reluctance to wear these plain
garments, commenting "You will have to earn the right to wear
truly feminine undergarments just as little girls must go through
the uncertainty of waiting to see whether their little nipple
buds will grow large enough to require sexy brassieres. Now get
dressed."

     "You will need some careful training before you get into
nylon, satin and lace. We are prepared to share our female
hormone pills with you. They won't give you wonderful titties
like ours, but they will enlarge your breasts. Better still, your
nipples will become engorged and sensitive just as ours do before
our period. Then some nipple training will lead you to appreciate
a real brassiere. Perhaps you need some silicone implants."

     Jacqui dressed quickly for going out in public where
everyone would know that he was not a real woman but a sissy-
shemale as they noticed the outline of his feminine panties and
his pink teen bra. Jacqui hoped that she would soon be allowed to
make a more complete female appearance with real lingerie and
makeup including nail polish and a wig.

FIN