Jack and Jill
by Vickie Tern (
[email protected])
Authors foreword
"Jack and Jill" is a novel in ten chapters averaging 30k each about a
fictional cross-dresser like you or me in fact or fantasy or remote
curiosity, or else why have you read this far, and how he or she became
the person who is narrating the story. It's mostly TG and femdom, with
forced or tricked or cajoled feminization, but of course also m/f and
m/m and f/f in various u.c. and l.c. combinations, and also some d/s,
and other such alphabetical stuff. Humiliation, yes, and mental but
not physical bondage. There is no pain, and no magic or incest or
bestiality or pedophilia or snuff, and no characters below the age of
consent, so if these things turn you on, or if you're yourself below
whatever age is lawful, this isn't for you.
You'd find this story boring, anyhow. The main character believes, as
many adults do, that we are reasoning creatures who can understand and
cope with our predicaments by thinking them through. Not so, but such
people do a lot of thinking aloud, and that's part of the fun. They
keep being surprised when events or other people's schemes cross them
up and mess their minds.
It's fiction, but any resemblance to actual persons or events you have
known, though accidental, is deliberate. A fiction that doesn't
resemble any of the worlds we inhabit, or any of the imaginary worlds
that inhabit us, isn't worth reading. It wouldn't even be imaginable.
None of the events depicted here have ever occurred to anyone I know or
have heard about, apart from the obvious and generic. Some similar
things happen from time to time. If to you, whatever your gender, I'd
appreciate your letting me know, to satisfy my own curiosity. But
don't assume I knew earlier.
Incidentally, only when it's absolutely essential do I describe the
length or thickness of a prick in inches or centimenters or rods or
acres, or at all, being convinced that the real world of men and women
are intimidated or else unimpressed by adolescent references to "my
rock-hard eleven inch pole" (dream on, 5 to 7incher if you're like most
of mankind but worry a lot about it). If you can't distinguish fantasy
from fact, the credible from the true, go take a good literature course
at your nearest Community College, or else go into a corner with other
A.S.S. stories and do whatever you do in corners while reading sex
stories. That's fine by me. This one tries to seem plausible, though
of course some situations go to extremes.
I wrote this because it was fun to write it, and I learned a lot of
things while doing it, about my own erotic imagination and about how to
tell a story, and about how to discover things while telling a story.
I hope to do better next time, but I'm pretty pleased with this one,
for now. I'd like to know what you think. If you must flame, make it
a flame of length equal to "Jack and Jill" (about 300k), if you can,
and at least as eventful and amusing (as boring's OK too as long as I
can skip through to the good parts), I'll be glad to read it.
Oh yes, I mean to post this through my AOL access, not my EDU access,
in order to increase the proportion of stories AOL contributes to
A.S.S.. Cretins who need to hate something to feel alive, or need to
feel unjustly accused to feel justified, spam A.S.S. daily attacking
and defending AOL subscribers. Between them and others who think their
learned theological opinions matter, reading A.S.S. on Usenet is now
like driving on a road littered with broken bottles thrown by drunks
(AOL gathers these threads into single line references the eye can
ignore). I have good reason to maintain both AOL and EDU accesses, and
if Johnny Duh out there is offended that I choose to pay good money to
AOL for certain desired services duly rendered, instead of trying to
locate a suitable freenet, or to struggle with an EDU network system
invented thirty years ago and still ten years behind the available
technology, well Duh!
This preamble is a test text. If it shows up in readable format on the
AOL *and* the EDU A.S.S, then I'll post it again with all ten chapters
all at once, for the world to deal with. If not, I'll figure out why,
and will welcome suggestions. Due notice: copyright is reserved to
me. Archiving and reposting in single transmissions is OK, if you
think this worth it, but preserve my name and address as down below,
and if you want to "improve" the story, don't. Write a better one.
That's what I'm trying to do as you read this one. Or rewrite 'Madison
County' and retire rich.
Dedicated to TG's of whatever kind, wherever you are.
Love to you all, Vickie Tern (
[email protected])ae
1. Chapter
I live alone. Oh, I've got a few girlfriends, and they fuss and worry
over me sometimes, and sometimes they arrange dates for me and we go
out together, and sometimes I arrange my own dates. But dates are
always a problem. I don't know which gender to ask out. I look like a
girl and I dress like a girl, and I live like one, and I work like one,
as a kind of secretary-typist-administrative-girl-Friday who doesn't
mind solving her boss's computer programming problems for him when he's
stuck. And by now I even act like a girl, and swing my hips when I
feel real good, and let my hands fly all over when I'm excited, and
squeal with my girlfriends when we're thrilled, and call things "just
precious" and "darling" and all that. But I'm not a girl. I'm a man
who's been feminized, by his former wife, if you can believe it,
because I wasn't man enough for her. People call me Jane, but my name
used to be Jack. And I still like girls, and inside my pantihose I
still have the basic equipment for coping with them, though it doesn't
work too well these days.
My problem is, how many girls want to date a man who has breasts and
delicate manners and wears dresses and loves to talk about girl things?
Even the lesbians are turned off when they find out I'm not a proper
transsexual woman, but a normal heterosexual male who has always loved
cross-dressing and who happens now to live in a mostly female body.
And how many guys want to go out with a guy who may look like a girl,
but hasn't got a pussy and isn't gay? Oh I'll blow them, because what
else can I do to please men if they're not into buttfucking, but
there's not much in it for me sucking on other guys' dicks or getting
my ass plowed (well, there's a little something, I do like it, my wife
saw to that). But sooner or later guys catch on that I'm not hot for
them, and sooner or later they don't come back. So I'm sort of caught
in the middle.
Probably I should go the rest of the way and have surgery and become a
proper woman and live a normal life. Or maybe I should go back to
being a man, if I can. A few more shots and cuts either way might send
me either way, I suspect.
But the problem is, I like looking like a woman. No, that's not true.
I absolutely adore looking like a woman! I always have. The most
wonderful thing I see when I wake up each morning is my mirror. I just
love seeing a pretty face and a well-turned feminine figure looking
back at me (see? -- "I absolutely adore," "I just love" -- my femme
talk turns on when I'm turned on, and just thinking about my mirror
turns me on!). I love feeling pretty -- there's such a marvelous glow
to it! On the other hand, I don't want to BE a woman. I can pretend,
and even fool myself sometimes. For some things, like feeling soft and
warm and cuddly and loving with someone, being a woman is just lovely.
But for most things I feel like a man, not a woman. Besides, if I
actually were a woman and I felt like one and dressed like one
routinely, where would be the thrill? Would I still feel deliciously
excited each morning when I put on a dress and step out knowing I look
pretty, my whole body feeling perky and blissful and privileged?
Probably not. Probably, I'd just feel normal, like any woman wearing
any dress anywhere.
I'm a transvestite. I love looking feminine, and I love the way it
feels to look feminine. I guess I was born one, and I'll certainly die
one. And that's where the problem started, how I got to be where I am
right now. I love wearing women's clothes, and I can't help myself,
and I don't really want to help myself. And now I live in them. I've
got what I wanted, or what my wife wanted for me. I'm permanently
cross-dressed.
I cross-dressed sometimes when I was a kid. I loved the feel of a bra
tugging on my chest, or a slip or a dress swishing on my legs. My
mother and sister never found out I was in and out of their clothes,
but it wouldn't have mattered to me if they had. I was hooked. I got
a paper route to help support my habit, to buy my own girls' clothes.
Once I rode out at first light wearing a blouse and skirt, cycling
furiously with my heart pounding and throwing papers at doorways at top
speed, scurrying to get back before anyone woke up and saw me. I felt
terrific about it at first, really high. But then I started to think
about the chance I had just taken and I started shaking and couldn't
stop! What I had just done terrified me!
After that I went deep into the closet, ashamed that I wanted to look
like a girl, and afraid to be found out when I did look like a girl.
Like most cross-dressers I got disgusted with myself and quit, a few
times, but then I'd start up again. When I finished college I wore
skirts and dresses all the time when I got home from work, all around
my apartment. I felt so right in them, so ...together. But I never
dared wear them outside. If someone were to look hard at me when I was
outside trying to pass I knew I'd feel embarrassed, then humiliated,
and then I'd panic and run, or come apart some other way. Then
everyone would look hard at me.
When I first met Jill I had just quit again, and it was just as well.
Jill was never a woman to think a cross-dressing husband kinda cute.
In those days, sexually, as far as I could tell, she was not given to
experiments or kinks of any sort. She wanted a husband she could
respect, a friend, one not too demanding. Sex for her had to be
strictly penises and vaginas, and that's what she called them, not even
oral. And sex for her was an occasional recreation, not a kind of
marvelous and crucial compulsory behaviour. She's a very good-looking
woman, a lawyer, tall and slender, with a decisive manner that keeps
her clients confident that she knows what she's doing. When we decided
to move in together I thought I would stay quit. We got along well.
We liked being with each other. At first she thought that my name
being "Jack" and hers "Jill" was just too cute for words, that we
couldn't possibly be compatible. But she weathered the kidding from
friends and associates, and we found that we were able to get on,
pretty much.
I respected her a lot, and she admired the way I did my work. We could
talk about anything, and she'd listen to me carefully. Then she'd ask
a few questions. Then she'd let some time pass, and finally she'd
deliver her own views as if she were a judge presenting a final
opinion. After that the question, if there was any, was settled and
not open for discussion. Usually we agreed, so I didn't mind that the
final decisions affecting both of us were usually hers. I got to
assume that was the way things should be, and I liked the way she ran
our lives. It saved me a lot of hassle. I think she was the one who
decided one day that it was time we were married, and I certainly
didn't disagree. By then I depended on her self-confident
self-assurance, and looked to it for guidance. I thought this was
love.
Once I tried to tell her about transgendered people, people like me,
trying to lead up to a confession that I had once been one of them
(and, I guess I hoped secretly, might be one of them again some day).
I thought I was being casual enough, but she turned the topic off
abruptly. She muttered words like "sick" and "perverse," and looked at
me closely. She then asked me in her attorney's voice why I had raised
the subject. A pang of fear sliced into me, and I said quickly that a
client had joked about it, that's all, and as soon as I could I left
the room to settle down, my heart still pounding furiously, still
terrified. A narrow escape. So my pleasure in wearing girls' clothes
stayed underground, hidden even from me. After a while I thought there
wasn't any. Which is why I didn't tell her anything before we got
married.
I began dressing again during our honeymoon. I know this doesn't sound
like a great compliment to Jill's sexual attractiveness, and I mean no
disrespect. But desire for a woman and desire to look like a woman
were very nearly the same thing for me. And back then Jill was -- well
-- deliberate in her lovemaking. Most of the kinds of love people like
she found "distasteful." She loved being in charge, controlling events
and controlling her feelings about them. If it wasn't cuddling, and it
wasn't vaginal intercourse, she didn't care for it, and she made that
known whenever I'd try to roam further with her. I knew from when we
started living together that she was severely inhibited, and I hoped
she'd loosen up in time. But it didn't matter. I needed her, and I
had come to depend on her, and she seemed to care about me. I would
marry her again, even now, despite everything she did to me. Maybe
because of everything, in a way. But not for the sex when we first got
married.
I still remember the morning in the hotel when she asked me to hand her
a white, delicately embroidered slip from her bureau drawer. I picked
it up and started toward the bed to hand it to her, and felt the most
delicious "THWANG!" as my belly rose up in joy at the feel of the
lovely thing in my hand, and my prick rose up too. Before I knew what
I was doing I had unfolded it and held it fitted in front of me,
admiring the lace across the hemline. "Very funny!" she said, as she
took it away. Then when she noticed my aroused state, she asked,
amused "Why, Jack, what can you have in mind?" I certainly didn't tell
her what I really had in mind, but one thing leads to another, and it
was easy to distract her.
That afternoon I stopped at a lingerie store and bought myself a slip
just like hers, and later that afternoon I hid it in our hotel room in
the back of our closet, so it would seem to have been forgotten by some
previous guest if she found it. She never did, and that was the
beginning of the stash that has since become my proper wardrobe. The
next morning while she was off having her hair done I put on one of her
brassieres and then my slip. It all felt so exquisite that I threw a
golf shirt and slacks on over them, and feeling delicate and dainty and
sweetly feminine, I went back to the lingerie store to buy my own bra.
I bought two, because I couldn't decide which was more "me," a satin
underwire, or a stunning lacy whisper of a bra I just loved at first
sight. Barely married, I was at it again, and absolutely delighted to
be at it again.
For a few years Jill never knew. As a lawyer she was very hard
working, and tough and devious I was told, and I could believe it. She
left the house every morning at eight and returned every evening at
six, often later when there was a big case brewing. I was then an
electronic systems designer, mostly computing systems. I wasn't the
cleverest one around, but I was precise and reliable, with fantastic
speed when I was writing up or solving problems, and that was my edge.
My client list kept growing because my programs always worked, and were
always installed on time. I kept a small office for consulting and for
storing the stock modules and menus I custom assembled for each client.
But until Jill found my clothes and demanded to know what they were, I
did a lot of my work at home, dressed and made up like the beautiful
woman I wanted to imagine myself, enjoying myself immensely. Then I'd
modem or fax it in.
At the other end of the fax was my secretary Darlene. Darlene was no
computer whiz, and no great brain either. But she knew the alphabet,
and she could be trusted to file any papers marked up with one of its
twenty-six letters, then to find them again and fax them out to the
house when I asked for them. She also impressed the hell out of
clients who came in to see me, and that was why I kept her on after I
found she couldn't do much else. She didn't need to. There she sat in
the reception area all day long, being gorgeous and fixing her makeup
and tucking in her curls, and answering the phone in a bedroom voice so
sultry people would think at first that they'd reached some 900 number
somewhere else. Her voice and appearance could seduce anyone into
being a client. I'd talk to Darlene a few times each day, and I'd see
her a few times each week when I went in to the office, and if it had
been any more frequent I'd certainly have gotten the hots for her
myself, and maybe what happened wouldn't have happened, at least not
the way it did. Jill wasn't happy that my secretary was such a Barbie
doll, but she knew that Darlene was just right for what I asked of her,
namely not much, and that she was even better for what I didn't ask of
her, namely to keep clients eager to call the firm with repeat
business. She knew that I never saw much of her, because I was mostly
home. So that was no problem.
We settled into a routine. Breakfast with Jill, mostly just coffee and
toast or a roll, me unshaven and in jogging clothes as if ready to hit
the old streets. Then as soon as Jill left for the day I'd shave twice
and change into a pretty outfit from the skin on out, bra, panties and
stockings with garter belt or girdle or maybe a pair of panty-hose,
slip, skirt and blouse or maybe a dress, or maybe a suit, or a slack
suit, and pumps, strappy heels, flats, or sandals, depending on the
season and my moods. I loved starting to dress by whim, in a mid-calf
full skirt or a slutty mini, and then matching everything else to that
first random desire, so by the end of the process I was dressed for the
day, wearing appropriate jewelry and settled in to work feeling elegant
and tasteful, my ensemble different each time. My hair is full and I
let it grow to cover my ears, so I could brush it back when I went out
as a man, and I could blow-dry it into a page boy to look feminine as
soon as Jill left the house, or even curl it when I wanted to take the
time.
Since I was home more than Jill and my time was more flexible, I did
most of the shopping. Sometimes I took to dawdling in the supermarket
at high risk, I thought, wearing women's shirts and pants, loafers and
"natural" (that is, invisible) lipstick, and with a feeling of enormous
risk maybe a touch of eye makeup. Beneath this undetectable femininity
-- not even androgynous, I realize now -- I wore wonderfully seductive
bras and panties and slips and teddies that would have reduced a cave
man to paralytic gibberish if he'd seen them on a cave woman. Once I
dared fate by wearing a flowered shirt that buttoned the wrong way,
living on the edge I thought. But I lost my nerve and never unbuttoned
my jacket to show it.
I never dared to go further, to appear in a skirt, or in unambiguous
makeup, because I was so terribly ashamed of this delightful
compulsion. To be found out would be devastating I thought, an
embarrassment I could never live down. My manhood was at stake. For a
man to look like a girl was demeaning, ridiculous. I shared the
world's view that an effeminate man is contemptible, a clown, a sissy,
a fruit, a joke, fit target for any insults. Even behind closed doors
and drawn shades at home I felt dangerously at risk. There was a
twinge of anxiety most of the time I was dressed, even at home, and I
kept my oversized jogging outfit on a chair as emergency cover gear if
the doorbell should suddenly ring. But I loved every minute of it. I
adored that image in the mirror, posing and primping. Nothing was too
good for her!
I also loved every minute I spent shopping for more clothes. When I
finished an important piece of work I'd reward myself with a special
treat. Dressed like a man, I'd carry into the store a slip of paper
with my sizes written on it, and I would seem to consult it as I pawed
through rack after rack of beautiful skirts and bodyshirts and dresses,
looking for the one item I simply had to have. I hoped all the
salegirls would assume I was buying for someone else, and I consulted
my paper frequently, as if women's sizes were obscure and beyond
comprehension. As if this persuaded them. As if they cared. But I
could not risk seeming to be what I was, even to strangers. I was a
man. To dress like a woman was to be no man, to be less than nothing.
All this gear grew in bulk, and soon occupied the closets and drawers
of my workroom and of another spare bedroom in our oversized house,
places where Jill never went. But it happened finally. One day when I
was at the office Jill came home early, wondering whether a spare
bedroom might make a home office for her weekends. She looked in on
mine, and at the size of its closet, and at everything in the closet,
and then she looked at closets and bureau drawers in the other rooms.
Lawyers are careful and thorough, and by the time I got home she had
located my whole extensive collection. She had also reached an exact
understanding of everything. She had concluded that while she was at
work I was keeping a variety of women in the house during the day, a
slut who wore leather minis and tight tubes and cutoffs, a
businesswoman who wore severe suits, a housewife whose tastes ran to
sundresses and flowered prints, and from all the drawers billowing with
sexy lingerie, a whole whorehouse full of high class call girls.
When I got home my life ended, my life as it had been up to that
moment, anyhow. In a tight voice she demanded to know who these
bitches were, and how I dared bring them under her roof. Incoherent,
humiliated, mortified, hysterical with fear, tearful and stammering,
for the next two solid hours I desperately tried to persuade her of
everything I had been trying to hide from her ever since our honeymoon,
the unacceptable truth about me. I pointed out that all of the clothes
and shoes were of one size, mine. All that proved to her was that my
taste in the women I brought home was self-absorbed and narcissistic,
and she said that from my behaviour in bed she'd suspected as much. I
tried to convince her that no women would ever consent to leave so much
clothing here. Too vague an argument for a legal mind to accept.
Desperate and red-faced, I finally stripped off my jacket, shirt, tie
and pants to display show her that even at that moment I was wearing a
matched embroidered slip, bra, and panties, all in the same size as the
clothing she'd found, a variant matched in brand name as well as size
by other brands and sets and styles and shades and colors of the other
garments hidden in my closets and dresser drawers. She was horrified
to stare at my body clad in its delicate lacy harness, and for once she
was speechless, as traumatised in her way as I was. Only then did she
begin to believe it was possible the stuff was mine.
So she sat me down and cross-examined me, relentlessly. When, how,
bought where? She kept returning to Why, and I had no real answer.
What finally persuaded her was my high marks on a tough quiz she
herself set and judged. Men never know anything about women's styles,
she was convinced, and she never hesitated to say it when I'd recommend
that she wear something I thought becoming to her. But I'd spent a lot
of time trying to look nice, even elegant, and I'd shopped with an eye
toward completing different outfits, and I'd kept up with the fashion
magazines despite my envy of all the beautiful women who populated
them. I did have reasonably good taste! She sat down and said, for
example. "Those red three inch heeled pumps! What would you wear with
those?" And I hauled out of a drawer the black pullover sweater I'd
worn with them, and from the closet in the room next door a matching
red full skirt; then I pearl-dived into my earring box and found a
perfect pair of dramatic coordinated black and red clip-on hoops. Or
she'd say "That blue and gold cocktail dress with the slit to the
waist, if it isn't higher -- what stockings go with it?" and I came up
with them, and "Is there a purse also?" and I came up with a darling
little matching clutch bag I'd found in an opportunity shop one day,
not believing my luck! Little by little she began to believe I had
spent more time on my outfits than on my computer programming. Maybe I
had.
She took due note as I folded each sweater carefully before putting it
back, and settled each blouse neatly on its hanger before hanging it
away -- obviously I knew and cared for each article the way she cared
for hers. She knew that in male mode I was a slob, my pants and
jackets ending up wherever I tossed them. I knew she was persuaded
when she came out with "That silver miniskirt -- that's for a teenager
looking to get laid! How dare you wear such a thing at your age?" I
showed her the ruffled blouse that kept me looking demure above if a
little slutty below.
Then her interrogation went on to its next phase. "I don't see any
outer garments. Where do you keep them?" she asked. I told her there
were none, that I never dared walk out even into the back yard when I
was dressed. She was astonished, and unexpectedly, angered by that
answer. "You don't flounce about outside in those things?" she asked,
"Why not? Are you ashamed of your perversion? Are you ashamed someone
might think you're a woman, or something else equally demeaning?" I
told her I was strictly a closet TV, terrified of being found out, that
my manliness would be compromised if it were known. "It isn't
compromised by the fact that you do it?" she asked. Then, again, "Why
do you do it?" I told her I didn't know myself, but that I had always
wanted to do it, that it was sometimes pleasantly erotic and always
deeply satisfying, and that it was a kind of compulsion, maybe inborn.
I started to tell her about the way it allowed me to express my
feminine side, and how gender and sex are different things, gender
being in the mind, and all that, but she wanted to hear no part of it.
I compared it to homosexuality, another gender orientation people don't
choose but discover in themselves.
That started a new round of ferocious questioning. "Oh, Jack? Do you
get together with other perverts, and do twisted things with each
other?" She sounded as if she couldn't even imagine what those things
were. I assured her that gays and transvestites were altogether
different, that gays are attracted to people of the same sex but
transvestites are so strongly attracted to the opposite sex they want
to look like them. I told her there were hundreds of thousands of
transvestites like me though I personally knew none of them, and that
no one knew about me except me, and now she knew. "Why do you want to
be a woman?" she asked again narrowly. I assured her I didn't, but
that I loved looking like one, and that when I looked beautiful, all my
desires focussed all the more on real women. On her, I added quickly.
She was not convinced, but continued, "If you like to look like a
woman, why don't you want to be a woman? Why don't you want other
people to know? Why do you hide it from me, your own wife? It's
disgusting, but is it so shameful?" I assured her it was, or I thought
it was, and she glared at me. Then she was silent. I awaited her
verdict.
"I see," she said. Then she said cryptically, "Everything fits!" And
then she sat silent again. Ominously silent.
I couldn't stand it. I said, "So now you believe me?," and she glanced
at me with enough contempt to wither a rainforest, then glanced away
again, and said nothing. She was convinced. I had been moved in her
mind from her frying pan into her fire, from a mass adulterer to a
pitiable, self-confessed drag queen, a hypocrite sexist wimp filled
with fear and self-loathing.
It was my night to serve dinner, and she sat through it frowning,
deliberately not looking anywhere I might catch her eye, chewing
slowly, saying nothing. As I poured the coffee she suddenly looked up
and said, "All right! Here's how it is! I married a man, not a woman,
and not an imitation man and not an imitation woman. I don't care what
your fantasies are like, or why, or what your so-called inborn
compulsions are like or why. I think you can stop, and you should
stop, and you will stop. From now on the only women's clothes in this
house will be mine. The only person wearing women's clothes in this
house will be me. You will be a man, and you will dress like one. You
will act like a man. Or else I will leave you, and I won't mind
telling all of our friends why I'm leaving you." She paused. "Coward!"
she spit out.
I hoped this was her final pronouncement, so we could begin to discuss
things more calmly. But then she added, "No talk! No explanations!
No pleading! I want promises from you first thing in the morning,
Jack, my so-called husband Jack, or I move out." She then went straight
into our bedroom and slammed the door. I decided I had better spend
the night in a guest bedroom.
No opportunity to talk, and no appeal. No way to ask even obvious
things, like was there was a deadline for moving my dresses out, or
where I should put them, or did she mean I should throw them out.
Before this I had seen her ruthless decisiveness, the way she would
speak her mind by uttering an ultimatum. But those dealt with trivial
things, like whether pizza or other such unhealthy foods should be
allowed into the house, or whether people who make porn movies should
serve long jail terms. She could be sharing, and lively, and fun, and
she could usually talk me into anything. But she could also switch on
her lawyer mode, as heavy and unyielding as cast iron, and then I was
afraid to dare to want anything she didn't want. This night would
determine the end of our marriage or its continuation on her terms.
And for me, life outside our marriage had become unthinkable.
I couldn't sleep. Then the next day I folded, or rather, I came apart.
I promised to do everything she asked, and that I wouldn't do the
things she hadn't asked, or rather, that I would stop dressing at home,
and that I would clear everything out of my closets, all the women's
clothing, that is, not the men's. I told her that as far as women's
clothing was concerned, from now on she could wear the pants in the
family, and then I apologized that I wasn't being sarcastic when I put
it that way. I told her I loved her, that she was the center of my
life. I started to cry, then I couldn't stop crying. She nodded,
looking a little sour, and I was still blubbering when she left for
work without a word.
That same day, I got a stack of boxes from a transfer and removal
company, made trip after trip, and brought all of my clothes to the
office. When I showed up in the reception area with the first box
Darlene raised her beautifully plucked eyebrows, checked her lipstick,
and asked what all of this was about. I told her Jill asked me to
store a lot of boxes here, figuring Darlene wouldn't have a followup
question. She didn't. I stacked them out of the way, against the wall
in the large utility room where we kept the xerox, the coffee maker,
and the office supplies
Within a month I was back at it, this time at the office. I took to
coming in early on weekdays, every day, opening a box of lingerie and
putting on panties, slips, teddies, stockings, and bras under my
business suits, so I could feel them hugging and tugging at me all day
long, then undressing and stowing them again after Darlene had left for
the day. I had the Reception area of the office mirrored, which made
it look bigger, and pleased Darlene because now she could see herself
from her desk by looking in any direction. Saturday or Sunday I'd
plead heavy overwork to Jill and head for the office, and then I'd
spend the day in a specially treasured dress or pants suit, or just
pass the time changing from outfit to outfit, admiring myself a little
wistfully in each, then trying the next.
Jill's mood seemed different after my unconditional surrender, or maybe
it was how she felt about me that changed, along with her idea of who
she had married. Obviously I was no longer her Prince Charming, but
some kind of would-be excuse for an imitation woman or an imitation gay
man, neither one nor the other. We fixed dinners for each other as we
had in the past, but instead of saying appreciative things when I put
in extra effort or she especially liked something, she'd say "Well, at
least this one came out all right, for once." Or if a dish wasn't to
her liking, then she'd say, "If you can't do it properly, why do you
try to do it at all?" When her turn to cook came around, as often as
not she'd pick up takeout on the way home from work. She did not wish
to serve me.
In bed she behaved the same way. She was never an enthusiastic lover,
as I've explained, but now Jill ...well...was not even affectionate.
When I would put an arm around her as we settled in to sleep, instead
of snuggling in at me she just lay there, and if I began to caress her
she'd say "Didn't we do this already this month?" or "I'd rather sleep,
but if you have to, try to pay attention to my needs for once." After a
while I quit trying. She didn't seem to mind. But at work, whenever I
stepped into a pair of hi-cut nylon panties I would get all the more
excited, and after a while whenever I was dressed I would masturbate
like a teenager. On weekends at the office, when I saw my mirrored
image in an exquisite white chiffon summer dress, I could hardly keep
my hands off myself, and I didn't.
I wondered if talk of separation or a divorce was in order, but I
realized I shouldn't raise the topic -- she'd simply say "You'd like
that, wouldn't you!", and leave me all the more aware that she would
rather continue to punish me for not being the person she had thought I
was. There was a breach of contract here, and I had penalties to pay.
We had our circles of friends, and we went to parties and dinners with
them, and Jill never let on there was a problem. As a lawyer and as a
woman, she hated to lose, and she wouldn't quit with me even after she
was convinced she had married a world class loser. And I realized I
didn't want to lose her. She wasn't fun, but her certainty
strengthened me. I didn't want to live on my own any more. I needed
her. I wondered whether the feminine in me was responding to the
masculine in her, but I couldn't think that one through, and I decided
finally that she'd get over her resentment if I waited her out.
Then something odd happened. Darlene looked disturbed one afternoon as
I came through the outer office, wrestling through things in her purse,
and opening and closing her lower drawers as if looking for something.
"Something missing?" I asked her. "Not exactly," she said. She
hesitated. "Uh, you don't happen to keep any tampons with your bras
and skirts and things in the utility room, do you?" I was shocked, and
said nothing. I replayed her words in my head unbelievingly. "Oh,
never mind," she said, "I'll check next door and see if Vera or any of
the other girls has any to spare." She started to get up. My hair
still stood up, and I felt struck in the stomach. I had to answer
something, so I said carefully, "No, why do you ask?" Mistake right
off. Better if I wasn't supposed to know what "Jill" had put in those
boxes. Darlene was still looking for her purse when she replied
absent-mindedly, "Oh, I've run out, and I thought maybe when you got
dressed up in those cute outfits you also put in a tampon. My brother
did. I better go see if Vera can help me." She got up, went out, and
headed down the corridor.
I went back into my office, and sat down with my mind roiled and
running half-crazed. She knew! But she didn't seem to care that she
knew! I had been hiding from her for months. But to Darlene, my
dreadful secret was no more than a possible source for tampons in an
emergency. What was my next move? Should I seem not to understand
what she had said? And if I didn't understand, should I let it pass,
or should I go back out there and ask her to explain it? Should I deny
that I ever "dressed up" in those clothes? I couldn't, because I
didn't know how she knew. Maybe somehow she'd seen me and there was no
way I could lie about it. Here was my worst nightmare come true a
second time, my ultimate humiliation known at the office as well as at
home. And it meant nothing at all to her.
I decided to take my cue from her, and without confessing anything to
ask her about her brother, as if none of this was a big deal or even a
little one. I waited until I heard her come back, and a little
apprehensive, I stood up and started over toward her reception area.
Somehow I felt that my life was about to change. It was a little
exciting. I told myself to calm down.
2. Chapter
I stood in the doorway. "Darlene, would you come into my office for a
moment," I asked. She picked up her Steno book and headed toward me,
with a questioning look when she saw I was a little distracted. I shut
the door as she came in and she looked even more puzzled -- the outer
office was empty, shut the door against who? Then I went back behind
my desk and sat down, and she settled into her usual chair when taking
dictation, and I folded my hands on the desk and leaned forward, trying
to look only casually concerned. "Um, uh, you know ...," I began, "Ah,
tell me about your brother."
She looked alarmed. "Why, is he in trouble again? He promised my
mother that he wouldn't...."
"No, no," I broke in. "I'm sure he's fine. I mean, tell me about his
putting on women's...er...clothing. Didn't you say he did that."
Darlene looked relieved. "Why yes, he did. He does, I mean. I mean
he's a woman now, so why shouldn't he? She!"
I was bewildered. "Your brother is a woman?"
"Why yes," she was puzzled I should ask. "Hormones and operations and
everything." Light dawned in her eyes. "That's how he had a place to
put a tampon," she said helpfully. "Or she has a place to put one,
now. But when she was still my brother and not my sister, he would put
one in his other place anyhow just so he could feel more comfortable
when he wore his women's things. That's why I thought maybe you did
too." Darlene obviously thought she had now cleared up all the
mysteries.
"Uh, Darlene," I said, looking out the window as if not much interested
in my next question or her answer to it, "Why do you think those are my
clothes in the ... uh...coffee room?"
"Why, aren't they? Your wife is going to miss them if they're not.
Why else do you keep them here? Why not just give them away if they're
hers and she doesn't want them? Besides," she said, and she smiled
reminiscently, "they fit you beautifully. You look darling in some of
them."
"You've seen me wearing those...uh...clothes, Darlene?" I asked in the
gentlest and steadiest voice I could manage, though I was now beginning
to feel, well, strange.
"Oh yes," her enthusiasm picked up. "A few times I'd come by the office
on the weekend to pick up something, and there you were in your office,
or looking at yourself in the mirrors in the reception area, wearing
the sweetest things. You looked just dear. Well, you never noticed,
and you were so busy I thought I shouldn't disturb you, so I didn't."
She looked thoughtful and a bit troubled now. "I've also seen you
change into panties and bras and things in the morning, when you got in
before me. But I get in pretty early. Tell me," she continued, "I've
always been curious. Why don't you put your panties and underthings on
at home before you come in? Don't you wake up in time?"
I decided that only the truth would serve. This whole conversation was
already touched by lunacy. I needed to keep it real. "My wife doesn't
like to see me wearing women's clothes, Darlene." I tried to suppress a
note of sadness. "She told me to take them out of the house. That's
why I brought them here. That's why I get dressed in them here."
"Oh," Darlene said. She seemed satisfied with my answer, as if my wife
was peculiar but entitled to her own inexplicable likes and dislikes
same as everyone else. "You know," she said, still thoughtful, "this
office isn't really a good place for dressing and undressing. And it's
really no place at all for putting on makeup, if you're starting from
scratch, because you can't clean up properly afterward. You use way
too much kleenex. Sometimes on Monday morning the wastebaskets are all
full."
My God! The wastebaskets! I used them without thinking!
Darlene gathered up her Steno pad and pencil, and gathered herself to
stand up. "Would you mind if I suggested something?" she asked. She
saw I was looking at her, mildly curious. "Why don't you bring all
those boxes to my place? You could get dressed and undressed there all
you want. I wouldn't mind. You wouldn't be in the way. I have an
extra bedroom you can use to get dressed. I even have an extra
dressing table where you can keep your makeup. It would be a lot
easier for you, wouldn't it?" She waited for a reply.
"Yes, it would," I said.
"Then let me know when you'd like to bring them over. I'll clear the
extra room and that can be yours." She giggled. "Not to sleep in of
course. I don't think your wife would like that."
"No," I said. But Darlene was already out the door and back at her
desk. I didn't know what I was saying "No" to, but it didn't seem to
matter. Nobody was listening. I seemed to have said "Yes" to
everything.
That evening when Darlene was leaving she stopped at the door to my
office to let me know, as she always did. I thought I should say
something that would show that her boss was grateful to her, and
interested in her well-being. "Uh, Darlene," I said, "Uh, did you ever
find a tampon?"
"Oh yes," she replied, smiling broadly. She had a terrific smile, but
usually she felt too distracted to unleash it on me. Not now. I got
both barrels, and felt staggered. Darlene didn't have smarts, but she
had it where it mattered. And she was gorgeous! "Vera had some
spares. Now I'm keeping a box in my desk, just in case. Let me know
if you ever need any."
I still don't know what she meant by that last offer. Maybe nothing.
But a week later I moved in with her, or my clothes did. She gave me
her spare room, with its walk-in closet, and I hung everything up, and
put everything in two dressers, and laid out my makeup on her extra
dressing table, and got a spare key from her, and went home to fix
dinner for Jill. It was my night to fix dinner. I felt wonderfully
cheerful, and a little bit guilty, because I was setting up with
another woman to violate an implicit understanding with my wife. But I
wasn't violating the letter of the law Jill had laid down. I had never
promised Jill I'd abstain from wearing my beloved women's clothes, and
this arrangement with Darlene was all really very innocent. Jill ate
without a word, then went in to watch the nightly news on TV. For once
I didn't feel snubbed.
We settled into a routine over the next few months, Darlene and I. On
weekdays I stopped by her place on my way to the office, and put on my
brassiere and panties, or maybe panty-hose, or a girdle, or a slip, and
then my regular shirt and tie if I was meeting a client, or an open
necked shirt if I was just planning to work at the office, and then
we'd drive in to work together. At the end of the day I'd drive her
home and change back. On whatever day I told Jill I was heading for
the office, Saturday or Sunday, or sometimes both, I'd go to Darlene's
place and dress up in whatever felt right -- a mini, or a long skirt
and blouse, or a cocktail dress, and do my face and my hair, and then
I'd lounge around and watch television, or fix some sandwiches for
lunch, or read, or work on some client's problem, and imagine I was a
lady doing all of these things, and feel very good about it. Darlene
never bothered me. She slept late on weekends, for one thing. When
she woke up she'd head drowsily into the kitchen, and if I was there
I'd have a fresh pot of coffee ready for her. If she liked whatever I
was wearing she'd compliment me on it, and sometimes make suggestions,
or chat about her own wardrobe, or about similar tastes among her
friends, and without ever discussing anything other than the most
superficial things we got to feel quite friendly, even intimate. I
felt accepted for what I was. We were like girlfriends gossipping at
breakfast. When Darlene would head off to shower and dress and set out
for her own day's activities, I'd feel very good about her, and very
grateful. .
Which may be why I made the first of several mistakes. One morning
when I was driving Darlene to work she turned suddenly toward me and
said, "You know, I think you'd be prettier if your hair were a little
brighter. I don't mean blonde or anything, but maybe some sun streaks.
And have you ever thought about getting a perm? When you set it in
rollers it would have much more body if you had a good perm down under
to begin with."
I reminded Darlene that I was not free to change my hair into a
specifically feminine style or color, because my wife would notice.
And besides, since I was a man, many things that made women beautiful
weren't appropriate for me.
This notion puzzled Darlene. "That's not true. Sun streaks look
natural. And with your shape of face, wearing your hair a little
fuller on the sides would be, kind of, nicer. Even sexier. Better
groomed, like Faye Dunaway. Especially now that you're letting it grow
out. I'll show you next weekend."
I don't know what possessed me, maybe the idea that Darlene could make
me look like Faye Dunaway, but the next Sunday I was sitting in a chair
with a sheet tucked and pinned around my neck while Darlene snipped and
primped and toned my hair with scissors and combs and brushes and
swabs, until by early afternoon she was done. She took out the rollers
and combed me out, and I was gorgeous! My hair had never looked so
full, and soft, and lustrous. I was delighted, really rapturous, and
when Darlene finally released me so I could stand up I turned and took
her by the shoulders and planted a kiss full on her lips. "You were
right, Darlene! This is really beautiful! I love it!" And while I
looked at my new hairdo my fingers moved up to soften a wave here and
to tuck in a curl there. The gesture was instinctively feminine, I
recognized at once, and I was all the more delighted by what Darlene
had done.
Darlene turned soft in response, no longer matter-of-fact but strangely
quiet. "Jack" she said, looking me over closely. "There's one more
thing that needs to be done. Why don't you sit down again, and I'll
take care of it for you."
I sat down again, and Darlene put some manicure scissors and tweezers
within easy reach on a table just behind me. "Now that your hair is
curved so beautiful," she said, "your eyebrows need to be shaped a
little better. Your bangs don't cover them any more. Just hold
still."
And to my astonishment she straddled my lap and sat down on it facing
me, her legs spread wide and gripping mine on either side, her crotch
rubbing directly on mine, her breasts just under my nose, her beautiful
eyes studiously serious as she stared intently at my eyebrows, not
quite looking into my eyes. "I think a higher arch would be more
beautiful," she said. And as she reached for the tweezers behind me
she tightened the grip of her thighs on mine and lifted her whole body
up and forward in a single motion. Her breasts brushed my face. I
should point out that we were both wearing only bras and slips, so as
not to get hair clippings on our dresses. I meant to pull on some
panty-hose when I finished dressing, and knowing I'd be covered by a
sheet while Darlene did my hair I hadn't bothered to pull on panties.
Now, with Darlene posting on my lap like a circus equestrienne riding a
stallion bareback, I could feel from the heat and moisture between her
legs that she also wore no panties.
In a state of shock I sat very still, and like an overgrown child she
twisted back, tweezed, lifted her elbow and twisted forward, tweezed,
wriggled her delicious fanny on my crotch, and tweezed yet again.
Needless to say, beneath my slip I had a raging boner pressing directly
into the opening of her pussy. She seemed not to notice as she studied
the sculpting of slightly higher arches onto my eyebrows, and tweezed,
and trimmed some of my longer eyebrow hairs with the manicure scissors,
and tweezed, and finally posted herself up off my crotch again with a
single squeeze of her powerful thighs, to place her instruments back on
the table behind me. I didn't dare move. "There, it's done!" she said
with a satisfied nod of her head. And still holding herself up, with a
single swift movement of one hand she lifted the hem of my slip beneath
her to my waist, and then settled herself down onto my stiff prick, now
tucked deep inside her.
"Oh God!" I said.
"You really are beautiful now!" she said in reply. And as I had done
with her a few minutes earlier she rested her hands on my shoulders,
leaned slightly forward, and kissed me full on the lips. Then she sat
back with my cock imprisoned inside her pussy by the full weight of her
body, and said with a satisfied smile, "Mission accomplished!"
That day we paid no more attention to my coiffure. I buried my face in
her abundant, perfumed breasts, and with both hands stroked her back
and sides along her satin slip, and looked up at her face to see that
she was looking down at me, her eyes half-closed, hooded under their
lids, her lips apart and still slightly smiling. I rocked my pelvis
slightly as if to seat myself deeper inside her, and felt the base of
my prick snug up tight against her. She was deliciously wet and warm,
and I as I rocked back down again she lifted herself up with a squeeze
of her thighs, and I slid along inside her in an excruciatingly slow
progress until my tip was nearly released by her pussy lips. Then we
reversed direction again, also slowly. Whatever her horsemanship, she
rode me superbly, slowly spurring me from a walk to a trot to a canter
to a full gallop in which we were each shrieking, bound violently
together in a single rhythm, each unaware that the other was making a
sound, both of us out of our minds. Finally I exploded, and spent what
seemed buckets inside her, while she crushed my face into her chest and
arched her own face back, toward the ceiling, screaming "AaaaaaHHHHH!"
with her eyes tight shut, her pussy squeezing and squeezing me over and
over in spasms out of control, until finally we both subsided and
collapsed onto each other, dripping with sweat.
As I softened I began to leak out of her onto my crotch, but she made
no move to dismount. The afterglow went on, and we sat quietly in each
others' arms. Finally she opened her eyes and looked at me and said,
"That was very nice. Do you think your wife will mind?"
"What do you mean?" I asked, stalling for time and in fact wondering
why she felt she should ask that question.
"I mean, your having sex with a lesbian. Doesn't that make her one in
a way too, all three of us being women?"
I was baffled, but tried not to let on. "Darlene, you're a lesbian?"
"Why yes, Jack, I thought you knew. Some boys I know are friends, but
I don't have any boyfriends. To really enjoy myself I have
girlfriends. Always. Ever since I can remember." She hugged me,
rather sweetly. "Now you're my favourite girlfriend. You're very
nice. You don't even need a rubber penis the way my other girlfriends
do."
"No, I guess I don't." We were back in Darlene's own world. I tried a
new tack. "Uh, Darlene, you do know that I'm not really a woman."
"Well, yes, I guess so, in a way. But you're so much like my brother,
and he loved to pretend he was a woman, and it turned out he wasn't
pretending. And you love to pretend that you're a woman. And now look
at you."
"Well, I can't look at me, exactly," I said.
"Here," Darlene said. She reached over my shoulders again to the
little table behind me and picked up a hand mirror lying there, and
leaned back to show me my face reflected in it. My heart rose up and
sank down, in both directions together it felt like. There over each
of my mascaraed eyes was a thin, high, aristocratic arch of an eyebrow
in such a delicately feminine curve that I felt a new erection begin
just from looking at them. At the same time I realized that there was
no way for me to disguise those fine traceries over each eye so they
would look masculine when I got home. With my hair teased out to frame
my cheeks and my eyebrows plucked I had a woman's face.
"Oh, God!" I said again.
"Jack," Darlene said. "What's your real name?"
"What?"
"I want to call you by your girl name. I'd feel better about what
we're doing. Don't you have one?"
"Yes, I do Darlene. Ever since I was a little kid, and got hooked by
my first bra, I've liked to think that a girl named Jane lives inside
me and is using me to dress herself. I'm Jane."
"That's so nice. Jane. Does your wife ever make love to Jane?"
"No, Darlene. No way."
"Well, then," Darlene said. "I guess there's no problem."
Again I didn't ask her what she meant. I guess I didn't want to know.
She sighed and snuggled down onto me again, and I began to grow harder
under her, and soon I was inside her again.
Well, the rest of that afternoon, and early into the evening, I never
did finish getting dressed. Darlene and I made love. When we were
exhausted by our second session with Darlene astride my lap, she
suggested that we go to bed together and make love properly. This time
I understood her. "You mean like girlfriends," I suggested, and she
agreed. By this time my pecker was slack, and I was willing to try
anything that didn't require a hard on. It turns out that's what
Darlene had in mind too. First she ran a tub, perfumed, and we both
slipped in giggling, glued to each other. We fondled and stroked each
other's slick bodies, and Darlene's fingers found my asshole under
water, tracing the clamped, puckered opening. We began to grow
passionate, stood up, and dried each other off slowly, exquisitely
slowly. Then we each of us fixed our hair and put on our makeup
carefully, each of us anxious to look pretty for the other. I slipped
into my most delicate nightgown -- one I'd never worn to bed before,
because I'd never been able to wear a nightgown at night. Then once we
were snug together, lying on our sides, facing each other and smiling,
the world turned radiant. Our hands reached out to each others'
bodies, and we looked into each others' eyes, and smiled, and caressed
each other, and closed our eyes only to moan softly, and then open them
again. I touched Darlene's nipples and she reached for my penis, and
we softly fondled each other, until we each came yet again! Then we
reached even greater intimacy with out mouths and fingers.
Darlene and I tried anything and everything, one after another, and
everything we did was wonderful. The key to Darlene's enjoyment of her
lesbian relationship with me was gentleness. Her mouth was soft, and
her tongue, and so was mine as we tasted and teased and tickled each
other, and licked, and kissed, and sucked, and probed. I went down on
her in an act of loving devotion, and sucked and tongued her as sweetly
as I knew how, and she bent over my soft dildo clit, as she called it,
and licked and stroked it with her lips. When it was time for me to
leave, just after dark, when my plucked eyebrows might go unnoticed,
Darlene and I hugged each other goodbye with respect and affection and
gratitude and appreciation.
But not with love. We two girls, as Darlene thought of us, were having
fun being girls together. For Darlene it was no more complicated than
that. On Monday when I stopped in as usual to change to my bra and
panties and take Darlene to work, her only conversation, as always in
the car, had to do with a sitcom on TV. On Saturday we were passionate
girlfriends again, and I was in heaven. Darlene seemed altogether
content that I was the girl with the dildo, though she was sometimes
concerned that I kissed and licked her pussy and also fucked it, while
she couldn't exactly reciprocate in kind with me, and had to settle for
kissing and licking my dildo clit or my anal opening. Another time she
asked me why I got nervous whenever she suggested we go out, maybe, for
dinner and a movie. I told her my hips were already too heavy, and I
was trying to lose weight. She thought I was slim enough, but
understood how a girl feels about her figure.
There was no problem when I got home that first night. Jill was
already asleep, and the next morning when I woke I could hear she she
was finishing her coffee and heading out the door. I headed for the
bathroom, and saw I was fortunate she hadn't seen me. My hair was
beautifully puffed out, with large stray curls tumbling here and there
and falling behind my ears, and my brows were plucked delicately high,
amused, inquiring, slightly surprised, slightly disdainful,
unmistakably dainty and feminine. I realized I had no makeup to cover
them with, not even an eyebrow pencil, and decided that today I had
better find a theatrical speciality store before Jill got home. At
least glued-on male eyebrows weren't on her list of proscribed
contraband.
When I took a shower I discovered another problem. Darlene had given
me a "Body-Perm", a light permanent wave to help form and hold the
large curls of hair she thought my face required. When those curls
were set with large rollers, each hair lay neatly against the next.
But now, stepping out of the shower, I saw my wet hair was sinuously
waved, hanging down in cascading ringlets. It didn't straighten when
it dried, and I thought I was going to have to pay the ultimate penalty
for my indulgence of Darlene, and get the permed part cut off. But I
wet it again, and a blow-dryer and careful brushing brought it to an
approximation of its former appearance. Close enough, anyhow. I would
have to be careful never to let Jill see me with my hair wet.
I found just the right hairpieces for my eyebrows, and attached them
with spirit gum, trimmed them back, and decided they would do. That
night was my turn to cook. I brought home prepared food from the
supermarket, heated it, and served it. I realized then that I was safe
enough. She never seemed to bother to look at me as she ate, and when
she got up from the table I noticed she looked away, as if I were still
some kind of embarrassment to her.
But there were things for her to notice without my knowing it, I
realized later. My bubble baths with Darlene left a faint perfume on
my skin, and then on my bedsheets, and it was three or four weeks
before I noticed. I began drowning the scent with an aftershave, and
Jill commented on my peculiar, sudden dedication to perfumed smells,
hardly ever used earlier. My stage eyebrows were a problem when I
slept. Once she found one near the kitchen doorway and called me. I
immediately declared it a caterpillar, and stomped on it before
scooping it out of her sight. But first I instinctively felt to see if
one was missing from my brow, and she may have noticed that off
gesture.
Once, Darlene mentioned offhand that Jill sometimes called my office on
weekends when I was supposed to be working there, and getting no answer
left a message on Voicemail. I checked each week after that, and found
that more often that not Jill was indeed checking up on me. Thereafter
I called the Voicemail service from Darlene's house every few hours,
each week. If there was a message from Jill I immediately called her
back with a variety of excuses why I hadn't picked up the first time.
But what really set Jill on the trail of her errant husband was the
oldest of all evidences of infidelities, lipstick on a shirt collar.
That it was my lipstick, from pulling on my shirt over my head before I
removed my makeup, didn't matter at all. If she had confronted me with
it, I might finally have gone on the attack, and asked her angrily what
a man with a frigid and sullen wife and a compulsion to crossdress
should be expected to do. I had already begun fantasying myself
married to Darlene, becoming her mindless girlfriend for life, and the
sexual advantages didn't seem that bad seeing that Jill and I were no
longer companionable in any other ways. My life might have been
different, if I'd done that. But Jill may have sensed this, because
she found the shirt in the laundry and still she said nothing.
Months went by. All those months of blissfully transgressive,
transgendered heaven may be more than anyone deserves, but I had that
much happiness as Darlene's in-house girl friend. I'll always have it.
I'll never forget it. But it ended.
One Friday afternoon Darlene's concept of me collided with Jill's.
Darlene called home when I was out, and got our phone answerer, and
left a business message for me. Then she called back and left a
message for Jane apologizing that she had borrowed one of my dresses
and stained it, and was very sorry, but it was ready at the cleaners if
I wanted to pick it up on the way over tomorrow, and she'd lend me one
of hers any time in repayment, she thinks she has a few that would fit
with just a little less padding in my brassiere. Then she phoned
again, and left a message for Jack to be sure to erase that message for
Jane, because she shouldn't have left it on Jack's answerer. Jill
picked up all three of these messages from her office, I learned later,
then left them for me to hear when I got home. I erased them in a
panic. But Jill seemed no different that evening, so I relaxed.
The next morning I was at Darlene's, my hair piled high and curly on my
head, wearing long dangly earrings because Darlene loved to feel them
between her legs, and they were clipons so there was no danger they
might tear my earlobes if she squeezed her thighs too tight, and I was
also wearing the sweetest little Teddy, with my lipstick smudged from
nibbling on Darlene's nipples, and with Darlene's lipstick smudged all
over my face, when the doorbell chimed and then, because Darlene had
left the door unlocked for me, Jill walked in. She didn't say a word.
She looked at me and lifted a camera, and flashed a picture of me, and
then another, and then one of Darlene, and then she walked to a corner
of the room and took one of the two of us together, and then another,
and then she went back out through the door and closed it behind her.
Darlene and I looked at each other. I knew she would say something
silly, wondering whether her hair was combed nicely for those pictures,
or wondering what they were for, or why Jill didn't stay for coffee, so
I just went over and held Darlene, and hugged her, and kissed her, and
looked at her tenderly, and kissed her again. It was very sad. It was
over.
3. Chapter
Jill never did say anything about her discovery of my little tryst with
Darlene, and I never saw those pictures she took either, and she never
referred to them again. She didn't have to. I knew she would use them
ruthlessly any time it suited her purposes. She knew what I most
feared about my crossdressing was exposure, and she knew I knew she
knew, so nothing needed to be said. I spent that night in a motel, and
spent Sunday at the office hoping for a phone call and dreading one if
it came, though none did. Again at the motel Sunday night, and again
at the office on Monday, with only business calls. Darlene,
miraculously, had worked out that I wasn't going to be stopping by her
place to change my underthings any more, nor to drive her to work, but
she was otherwise her usual sweet, simple self, untouched by my
domestic catastrophe.
For a few more months after J