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Archive-name: Changes/jacqui.txt


Archive-title: Gender Fantasies

                             Chapter One 

     As a hetersexual, who is also a secret transvestite with a raging 

lingerie fetish, John'sactive sex life exists in two different dimensions, 

mixing fantasy and reality. John loves women and worships their delicate 

satin and lace lingerie. 

        None of John's women would describe him as a hunk or stud, but all 

find him to be a patient and skillful lover who attends gently to their 

bodies and carefully to their sexual needs. He is slender and slight of 

build, and always expresses great interest in the dress and appearance of the 

women with whom he shared mutual attraction. His appreciation of their 

femininity is always apparent. 

        It is that appreciation which provides a clue to the other John 

perhaps better known as Jacqui who has a raving preoccupation with the 

feminine undergarments of all women. His gentility with women is a direct 

manifestation of his own frustrated femininity, relieved only when in 

proximity to intimate feminine garments. Our hero(ine) is always on the 

lookout for any opportunity to experience, no matter how vicariously, the 

joys of sensual, sexy, feminine lingerie. 

        The sources of John's arousal and satisfaction are far ranging: from 

avidly reading brassiere and panty advertisements in newspapers, magazines 

and catalogs, through careful but discrete observation of displays in stores, 

to voyeurism, also discrete, in social situations. 

        John    is always alert to every possible clue about the 

undergarments, especially brassieres, of any women with whom he has contact. 

Is there a peek at bra or breast because of the decolletage? Does a gap 

between buttons reveal a glimpse of satin and lace? What can be deduced from 

the bra outline traced under a blouse or sweater? Does an erect nipple 

visible as it strains against bra and blouse? Is the lace trim visible 

through a sheer blouse? Does the outline of the straps reveal a front 

fastening bra, or a t)back? 

        But breasts and bras, while first in John's interest, are not the 

only thing to atrract his attention. The glimpse of a frilly slip, especially 

seen because of a skirt slit or wrap*around is certain to be noticed, as is 

the presence of a pantyline showing through skirts or slacks. Most entrancing 

of all is the telltale outline of a garter and stocking tab indicating a 

truly feminine woman wearing a garterbelt or bustier rather than pantyhose. 

        Each of these vicarious thrills,  however, are only a prelude to 

John's transformation into Jacqui. Read on as Jacqui recounts the details 

savoring her affection for each exquisite manifestation of her degenerate, 

petticoated, sissy)status. 


        Nylon panties are a basic item of feminine apparel in Jacqui's 

transformation into a sissy who wants only to be treated as a sex object by 

whatever woman allows him to provide her with sexual gratification. Most of 

the time, however, Jacqui is not able to find a woman who can accept her as 

the totally submissve transvestite that she aspires to be. Mostly, she must 

rely on her own imagination and devices which are also satisfying and can 

provide for long periods of intense arousal and self)release. 

        But, back to the details of Jacqui's passion, starting with those 

wonderful nylon briefs. Bikini panties are for cute, lithe little buns and 

absolutely flat tummies. But, Jacqui must also be able to restrain her 

pre)tumescent clittycock which is so easily aroused. That requires panties 

with a wide crotch, not only to keep John's ugly, hairly balls snugly 

retracted in their scrotal sac, but also to keep Jacqui's sanitary pad in 

place. While a pad isn't always necessary, there are times when it is 

essential to keep from staining delicate panties. A panty liner is sufficient 

to  catch  tiny drops of semen which may leak,  in a most  unlady*like 

manner, from John's naughty penis when he has been aroused for too long 

without relief. Using a belt to hold a sanitary pad also helps to preserve 

Jacqui's flat profile by keeping John's penis well contained. 


        As we already know, titties are at the absolute center of Jacqui's 

most exciting fantasies and so brassieres are almost her singular 

preoccupation. The very sight of John's Mistress in her bra reduces him to 

begging for a feel of her wonderful globes encased in the heavy satin of her 

exquiste brassiere. And, it creates an almost intolerable urge for 

transformation into Jacqui as John is torn between desire and envy. 

         Any sight of Jacqui's most favorite feminine garment is a thrill. 

(S)he is never certain which is the more exciting, the titties or the 

marvelous eroticism of that most alluring of garments, the brassiere. 

Obviously a bra looks best on a slender, full) breasted woman, but John loves 

to look at and study all bras. 

        It is always difficult for John when contempating Jacqui to decide 

what was more pleasurable. wearing a bra with  pretend titties or just by 

itself. When wearing titties created from rice)filled nylon stocking bags 

with the top knotted to created a nipple outline, there is the wonderful 

tension of shoulder straps and the delightful weighted curve which feminizes 

posture and shape. Without the inserts, she can caress, massage and pinch her 

nipples which is also so exciting, even though they are pathetically small 

even for a very flat)chested girl. Real women are so lucky to be able to 

experience both sensations. 

        Small breasted women can wear a padded bra to increase their 

contours, but only within limits because pads lack the natural shape which 

makes tits so attractive. Tight blouses are revealing when breasts strain 

against the fabric of the bra or the blouse to reveal the pert outline of an 

erect nipple. But the effect of a loose,  slightly open blouse which allows 

both a peek at a lacy  bra as well as revealing the breast contour is even 

more erotic. 

   The advantage for small breasted women is that they can wear the most 

delicate of bras with flimsy cups, extra lace and narrow,  stretchy  straps.  

They also look wonderful wearing  demi*bra styles with half cups on which 

their delicate globes rest, nestled on a slightly padded shelf of nylon, 

exposing the soft white flesh and perhaps an erect dusky nipple. 

        John's ideal is a B)cup size which allows for almost any bra 

selection including strapless and front closure as well as the newer y)back 

back styles which he notices more frequently now as their outline is 

distinctive. Jacqui recently bought one. Wearing it nicely filled with 

pretend titties is delightful. It allows plently of jiggle when Jacqui walks, 

but the slender straps stay nicely in place without slipping whether the cups 

are filled with make)believe titties or not. 

        There is a problem for the she)male pretender which real girls don't 

experience. That is, without the weight of titties, bra creep can be a real 

problem, especially when worn under male clothes in social situations where 

weighted bra)forms can not be inserted. Then, straps can slip and the 

frequent necessary adjustments create a real risk of detection of one's 


                             GARTER BELTS 

        Jacqui also has a red, lacy elastic garter belt which circles her 

waist, just above her hips, with the garters stretched tautly over thighs and 

buns, held in place by snug, satiny panties. Worn without panties, under a 

slip and skirt, it allows freedom for John's cock and balls, and access to 

them for fondling. Panties are, however, usually necessary to restrain his 

naughty male organ which has a tendency to bulge as a result of the 

stimulation attendant to wearing feminine garments 

                            WAIST CINCHER 

        John recently come yet another step toward feminization, but yet also 

another step in being forced to the realization of how unfeminine a male 

shape will always be. Having failed in courage on an earlier attempt, he 

finally purchased a black, nylon waist cincher with stays and long black 


        On his first venture to the garish shop, John could only thrill to 

the sight of so many pleasurable garments on display, all oriented toward 

enhancement of the female form or feminization of the male. There were white 

and red and black brassieres of every design and size. There were breast pads 

with molded nipples. 

        The selection of panties was fantastic as was the array of garter 

belts. There were costumes for maids and other servants, all on female models 

but clearly available in larger sizes for sissy males such as Jacqui. 

        The clerks were all elderly and watchful but not in a threatening 

way. On his first visit, John carefully examined the selection of waist 

cinchers but was afraid to make a selection even though the price was modest. 

        On a return trip, however, he again carefully examined several with 

growing but controlled excitement. Finally, John selected the one he thought 

would most feminize his shape. As the clerk completed the sales slip, he 

asked whether John needed stockings. John knew that he had taken another step 

toward being comfortable with what he was. He felt no need to make excuses, 

but only stated that he had an adequate supply of nylons. 

        Imagine his chagrin when, after driving home with great anticipation, 

he discovered it to be too large. He clearly needed something smaller if it 

was to create a properly constricted feminine feeling. It required some 

resolve to go back because the sign in the store clearly stated "no returns 

or exchanges." 

        But, John's needs for perfection and feminization won out. He 

returned to the store, albeit with some trepidation, determined to achieve 

goal. Without hesitation, John told the clerk that he had made a mistake in 

the size; and that his Mistress demanded that he replace the garment with one 

affording more control. John apologized, as instructed by his Mistress, for 

not having tried it to be certain that it was tight enough. That was 

important to remind John that becoming Jacqui required occassional public 

humiliation by letting others know that he was only a sissy with a pathetic 

clitty)cock trying to pass as a woman with real titties, smooth shapely legs 

and round buns which deserved to be pampered in nylon and lace. 

        John selected a smaller size, but even though it looks and feels 

snug, his Mistress has determined that if she is to tolerate this sissy who 

wants to wear her clothes, he must be forced into still tighter corset 

bondage. That is Jacqui's next goal even though her black, nylon cincher gets 

her very aroused when she is permitted to wear it and looks perfect with dark 

nylons, pink panties and black pumps. 


        John's Mistress has a wonderful wardrobe of petticoats all of which 

fit Jacqui comfortably. Most are pettis, but she has one full-slip which is 

large enough and heavenly to wear. It not only emphasizes Jacqui's bustline, 

but fits snugly over her torso as it flairs out from the waist. It delicately 

swishes against Jacqui's thighs when she walks while wearing her black 

leather pumps with modest heels. It gently caresses her thighs when she sits, 

especially while wearing her garter belt. And, it does cover John's hairy, 

and thus markedly unfeminine torso. 

        The only disappointment is that except for one very short petti, 

which Jacqui adores because it is taffeta, none of Mistress' slips are narrow 

as she prefers the A-line style. Jacqui would be ecstatic to have an ankle 

length straight slip which fit snugly. That would remind her to take short, 

lady-like steps when she walks, and when sitting, would display her garter 

belt tabs to remind Jake in another way of his feminized status. 

                              CHAPTER 2 

        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 of bra being worn)  there was a selection of front 

and backhook bras. Most were very flimsy and delicate, and all were 

underwired  to support her luscious C)cup titties.  Some were push*up, 

demi)styles. Even better, all were in size 36, 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 panty)clad 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 


        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. 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 pink balloons. 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 3 

        "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 his pretend pussy. And, he had to keep his 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 


        "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. 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. 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." 

        "I also 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 4 

        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 


        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 hair 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 


        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 


        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 


        "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 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. 



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