TG: Jack and Jill Ch 2 by Vickie Tern, femdom, wife, M/F, M/M 

Vickie Tern's stories are archived at 
http://library.gaycafe.com/nifty/transgender/
by_authors/Vickie_Tern

She appreciates any kinds of comment on any
of them,  and usually replies in kind.






If you shouldn't be reading this, don't!


Jack and Jill by Vickie Tern


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.

"O 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.