TG: Jack and Jill Ch 5 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

5.  Chapter



Still standing by my front steps, near a dim street light, I opened my
purse.  There was the makeup I had used earlier.  There was a folded
piece of paper.  There was a Motel key, with a huge weighted fob
attached imprinted with a name and a room number.  There was what I
recognized as the spare set of car keys, with a small flashlight
attached on a chain.  There was a packet of condoms.  There was a
3-pack of tampons.  I opened the piece of paper.  It was a note from
Jill, typewritten, meaning that she written it some time before this
whole awful evening had begun.  When she wrote it she was already
imagining me reading it right now.  And now here I was.

"I want you to think about me and Tom here tonight, in our beautiful
bed.  Are you thinking about it, and about marital fidelity, and about
being honest with each other, at this very moment?  Good!  If you want
to resume our marriage, go to the motel room printed on the big key,
and you'll find out what else I want.  You'll be there for two nights.
But you won't have to feel lonely.  You'll find there's a beautiful
blonde young man who hangs out with the night clerk and provides
whatever services guests may require.  He's very good, very gentle with
first-timers, I've been told.  He's very attentive.  But I didn't
arrange anything with him for you for tonight, so if you miss Tom's
prick and want some more lovemaking before bedtime you'll have to talk
to him yourself.  Sleep well, dear."

I looked back at our house.  A light in the bedroom had gone on.  There
was nothing more I could do.

So I went around in back, got in the car, and drove myself to the motel
indicated on the key, not too far away.  It felt odd driving the car in
a dress, pressing on the accelerator and the brake in high heels, and I
drove very carefully so there would be not the slightest risk of a
policeman stopping me.  When I had parked in the motel parking lot I
sat still for a few minutes, to psych myself up to meet yet another
stranger while dressed as a woman.  Could I pass?  I checked my hair
and my makeup, and walked across the lot and into the lobby with what I
hoped was a persuasive woman's walk, short steps, elbows in, mincing
slightly.  At the front desk a night clerk looked up at me without
changing expression.

"Can you tell me where is Room 244.  My wife made these arrangements."
I realized that I had just blown my cover!  He didn't blink, but merely
checked his register.

"Yes.  Room 244, pre paid for two nights.  One flight up and to the
left.  The elevator is just behind you.  Have you any luggage, ma'am?"

"No." I felt foolish standing there in a dress and I wanted to get out
of the clerk's sight, so I hobbled down the corridor as I fast as I
could, realizing that I'd been wearing heels for many hours now, and
they were beginning to hurt.  The clerk had confirmed what Jill's
letter said, that I was here for "two nights." Why?  So she could play
house with Tom for the weekend?  So I'd think that's what she's doing,
whether she is or not?  I felt a pang of jealousy.  That's what she
wants me to feel, I thought, but I owe her, so I have to pay her.  At
the same time I felt an odd twist of excitement at the thought of Jill
and Tom romping together tonight, and all day tomorrow, and tomorrow
night.  It didn't seem like the same Jill.  I wondered if she was more
imaginative in her lovemaking with Tom than she'd been with me.  During
the past few months, I realized, she had changed from the girl I had
married.  She had always been assertive, but now she was domineering.
And cunning!  Tricking me into sucking Tom's cock!  Does she just do
straight screwing with Tom, then go to sleep?  Does she let him know
whether she enjoys it, or does she keep that a secret too?  I suppose
the two of them have a different kind of lovemaking, anyhow.  Then I
realized I was beginning to picture them wrapped around each other,
arms and legs tangled together, and I realized I had better stop
thinking about it.

I entered Room 244, and saw immediately someone had been there.  The
closet had clothing in it, women's clothing, a suit, a few dresses, a
skirt and blouse or two, and a terrific-looking cocktail dress.  I
thought at first this was a hideaway Jill kept for herself, but I
looked again, and saw that everything was was in my sizes.  In the
bathroom was an elaborate makeup kit.  I checked the drawers.  One had
a few bras and panties in it, again my sizes, and that one of the
panties was crotchless, with ribbons to tie together the bottom seam.
There were several magazines on the night stand, Cosmo and Vanity Fair
I noticed, and when I looked for a Time Magazine or a Newsweek, I saw
that another was Seventeen.  Only girls' or women's magazines.  Jill
had thought of everything.  I started to get undressed.  It had been a
long night since I had put on this very blouse and skirt, Jill urging
me to look especially pretty for this guy she worked with, and me
without a clue about what she really had in mind.  He did come on to me
after all, I realized, and I had made love to him after all.  A long
night.  I set my slip aside to use as a nightgown, then saw that Jill
had left a lovely, frilly nightgown across my pillow.  For me.  Well,
that was something.

I didn't know how this room figured into her plans.  Did Jill feel
guilty about putting me out of my own home?  I doubted it.  Was she
setting me up to live separate from her, with this clothing a kind of
payoff she knew I'd like?  No, she'd have told me about it beforehand.
She always wanted me to understand clearly what her rules were, and
why.  I didn't know what I was doing here.  Being out of her way while
her boy friend fucks her, I supposed.  The nightgown felt silky smooth
as it slipped over my chest and hips.  It had sexy lacework circling
each breast.  I looked at it in the mirror, and for the first time that
night felt nice.  I was pretty.  I was myself.  This was all too
confusing.  I turned out the light, and fell asleep at once.

I was awakened the next morning by the sound of a key jiggling in the
door.  Terrified, I called out "Who's there?" as I ducked under the
covers to hide my nightgown's frilly shoulders.  The door swung open,
and a thin blonde young man entered with a rolling cart filled with a
Room Service breakfast.

"I knocked, but no one answered," he said deferentially.  "I hope you
don't mind my using a key to come in, but that was listed as one of the
things I could do during your stay.  I'm pleased to make your
acquaintance.  I'm Carl."

"Let me see," he said, looking at a list on his clipboard.  "Yes.
'Well, uh, Jane, if I may call you Jane.  Your wife advises that you
spend the day here.  We have an excellent restaurant, and a pool area
for swimming or sun-bathing -- you'll find a swimsuit and wraparound
here in the room.  If you need anything else, the pool shop will have
something that would fit you.  I'll be back tonight at around eight, to
let you know about the wonderful things she has planned for this
evening.  Oh, yes.  The hotel beauty salon has an appointment for you
for this morning at 10:00 am.  A complete makeover -- expect to stay
about three hours." As he opened the door to leave he gave me a warmly
reassuring look, and then a charming smile.  "Don't worry, Jane.
Everything has been arranged and paid for.  You don't have to do a
thing.  Just enjoy yourself."

He left.  I noticed that while he was talking my nightgown's frilly
sleeves had come fully visible to him.  But it doesn't seem to have
mattered, I thought, since he seems to be better briefed about me than
I am.  I was glad to have breakfast in the room, anyhow.  It delayed
the moment when I had to go out by daylight.

Then I thought, enough of this.  I'll talk to Jill directly.  I called
home, and as the phone began ringing I suddenly wondered who would pick
it up.  Whose voice would I hear?  After the third ring I heard Jill
pick up and say "Yes, hello?".

I started speaking before she could decide to hang up.  "Jill I want to
come home.  Is Tom still there?"

"Who?"

"Tom, your boyfriend."

"O yes, Tom, that was his name.  No, he left early this morning; he had
another woman to attend to."

"Your boyfriend?"

"But dear, he's not my boyfriend!  I'm married.  You remember."

"No?  I saw you kissing.  I saw the way you greeted him at the door."

"Oh, you did!  I was so hoping you'd sneak around and catch that little
drama!  So that's why you looked so strange when you came in and I
began telling you the story of your death.  Oh Jack dear, that was all
a show for you.  So was all that lovey dovey during dinner.  All for
you.  No, Tom was my escort for the evening, and for other things.  I
hired him and told him what I was planning, and what I wanted him to
do, and he did it all very well."

My head began to whirl again.  I couldn't keep up with her.  "Did he
know about me?  Did he know I wasn't your woman friend?" "

Her voice sounded marvellously good-natured.  "Why darling, of course
he knew about you.  I told him you were a closet fairy.  I told him
that my husband would show up wearing a dress and pretend to be my best
girlfriend, and that we should go along with it.  I told him that all
your life you have wanted to give a man a blow job while wearing a
dress, because that's what real women do, but that you were too
embarrassed to set it up for yourself.  I told Tom it was your birthday
and that he was my present to you, a real man you could suck on like a
lollipop, to your heart's content.  I told him you'd go down on him
without any problem, and you certainly did my darling.  And I told him
he should help you with it, your very first time, without letting on
that he knew you weren't just one more slut who blows cock every night.

"I knew you'd do anything to keep him from finding out you were just
another pansy in a dress.  I knew you'd go along with it no matter how
humiliating." Her voice grew triumphant.  "So sweetheart, I turned you
into a pansy in a dress!"

I remembered how helpless I had felt as I sank down on my knees between
his legs last night.  For nothing!  I felt mortified.  Tears came into
my eyes.  She had set me up!  From the very beginning!  She had even
advised me what blouse and skirt a well-dressed husband should wear to
his first blow job.  I tried to say "Very clever!" with acid irony, but
all that came out of my mouth was a little strangled sound.

Jill continued.  "But I was very considerate, dear.  I told him that I
wanted it to be wonderful for you, unforgettable, so that you would
always remember it, your very first.  I wanted him to teach you how to
enjoy every moment.  I told him I wanted your mouth to remember it even
if you tried to forget it.  And your mouth does remember now, doesn't
it?" She paused, then she went on.  "I could tell that your mouth was
learning, love.  I could see by the way your lips kept their sweet
little pucker, their little cuspid bow shape, and couldn't stop kissing
the tip of his prick whenever you came up for air, and then how they
made that pretty "O" whenever you went back down on him.  You really do
have a talent for it, love, don't you."

"You could see that?" I broke in, shocked.  "You said you were in the
kitchen."

"Oh, no!  See that?  Why love, I was there!  There was no way I was
going to miss the sight of my darling husband in a dress sucking cock
like a ten dollar whore and pretending to like it.  You were so busy
head-fucking that man's dick you never noticed me!  You must've really
gotten into it!  Was it that great?  I took picture after picture of
you slurping Tom's prick like a big purple ice cream cone!  It looked
really wonderful for you.  So that's what you guys do when you get
together!  That's what male bonding is all about!"

She paused again.  "When I heard him tell you how to feel every nuance
of his prick in your mouth, he made it seem so attractive I thought of
giving it another try myself.  I told you on our honeymoon it just
wasn't my thing, didn't I. Well, maybe I just never had as as good a
teacher as you just had.  You did so enjoy it!  Dear heart, you make
such a darling little cocksucker!"

Her affability faded.  "And now, you're my darling little cocksucker,
Jack dear.  I have snapshots of you dressed up with Darlene, and
dressed up with Jack, dressed up and going down on that stud, and now
you little faggot I've got you where I want you." She stopped and
caught her breath.  "Not that I didn't before.  I think we understand
each other.  Stay another night at that motel.  It's all arranged and
paid for.  I need one more night by myself.  Then you can come home and
we'll see what we'll see.  I think starting tomorrow we may be able to
live together again darling.  Maybe happily.  Even joyously.  On my
terms.  But not if you're still the way you are.  If you'll do what I
say, maybe.  Spend the whole day being a woman, Jack.  That's what you
say you want and that's what I've arranged for you.  I bought those
bras and dresses for you, and made all of your appointments for today.
You should feel grateful.  Spend one more night.  Otherwise don't come
home at all, and I'll think about how I want to share the pleasures of
my new photograph album."

The line went dead.  I hung up at my end, and sat there a while.  Then
I picked up the copy of Vanity Fair.  A gorgeous young woman looked
back at me, smiling with approval and congratulating me on becoming a
darling little cocksucker, maybe even as good with the guys as she was.
The magazine cover promised an article inside on four new male film
stars worth masturbating over, and another on how to keep your man by
fucking his brains out.  I wasn't ready for this.  I picked up
Cosmopolitan.  A randy lady on the cover in an undersized red evening
gown, her breasts and shoulders exposed wherever they bulged out from
the material.  Inside, three ways to apply the new Spring lipsticks,
and advice for girls who like to seduce other girls, not men.  I
started trying to read about lipsticks, but couldn't find the article
among all the ads.

So I read the ads.  My spirits picked up a little.  Today I would be
Jill's kind of woman.  She had bought me clothing to wear.  I thought
about Medea, the jilted woman of Greek mythology who poisoned her
husband with an impregnated cloak.  No, Jill wanted me to change, by
spending the day dressed up.  By going to the beauty parlour?  There
were worse things than trying to be one of those drop-dead beauties in
the perfume ads.  Well, she seemed to be meeting me half-way even while
rejecting me.  I got up and looked more closely at the clothes hanging
in the closet.

First off, I would try to pass without attracting attention.  There was
a pair of stone-washed blue jeans, and a shirt.  I took them down,
checked the underwear drawer for a bra and plain pair of panties, and
put everything on.  So far, fine.  Everything a little snug, but basic.
They fit.  The bra gave me a little bulge in the chest when I set my
shoulders back, but nothing noticeable.  The pants were very tight in
my buttocks, but glimpsing the curves in the mirror, and the sharp
separation of cheeks they gave to my ass, I thought, not too bad.  A
pair of flats on the closet floor I recognized as mine, and I put them
on -- no way they could be thought to be men's shoes, but I loved the
way they curved on my instep.  I went into the bathroom and shaved
twice, then again, and started to think about how how much makeup I
needed to get through the morning without seeming to be a man in
women's clothes, when I suddenly realized it was ten minutes to ten.
My first ever visit to a beauty salon as a woman!  But of course they'd
know at a glance that I was a man!  But Jill had arranged it -- of
course they already knew.  My heart began to pound.  I picked up my
purse, checked that I had my room key, headed out the door, and saw a
sign pointing to the Salon off the pool patio at the end of the
corridor.  I walked as rapidly as I could, hoping no one would see me
and wonder what I was.  No one did.

A woman in a pale purple smock looked up from arranging bottles on a
work table when I came in.  I glanced around -- there was no one else
there.  "I'm Jane," I said, in what I hoped was a persuasively high
voice.  She looked at me without changing expression.  I almost added
"My wife made an appointment for me...," but I choked it off, and just
looked back at her, thinking that maybe I could get away with this.
"Yes," the woman said, "How are you, Jane?  Your wife wasn't sure your
hair would be long enough for a really feminine style, but I think we
can manage.  Sit over here, dear, and we'll think about you for a
while." I sat down.  "Tell me, something your wife couldn't answer for
you.  Will you want a hairdo you can just comb out each morning and
forget about all day, or do you like to primp and shape it with rollers
and mousse and curlers and things?  Some women like to fuss, and some
hate it.  Which kind are you?"

I loved fussing, but there was no way I could say so.  "Is there a
style I can sometimes wear, uh, plain?" I asked, meaning one that could
look like a man's cut but still look feminine when combed right.

"Well, yes, Jane, but not for you.  Your face is too large for a gamin
cut.  You could look really lovely if you had masses of hair framing
your whole head, but that needs longer hair than you've got, I think.
Besides, my instructions are, make you look as pretty as you can be
right now.  I tell you what.  Leave it to me.  I think for now a curly
top barely covering your ears on the sides, high on top, with just a
wisp of bangs, and you'll be just fine.  Your earrings can just peek
out.  Not too hard to take care of, either.  And as it grows out, it'll
still look pretty.  Different of course.  But you can always have me do
it again if you want to keep it the way it is.  The way we're doing it
now, I mean."

As she led me over to a sink, slipped a smock over me, and leaned me
back for a shampoo, she asked "Tell me, honey, why is it you want to go
all the way?  I can understand a make over for a costume party and then
back to business as usual the next day, sometimes men come in for
those, but your wife tells me you'll want to look feminine for the
whole foreseeable, no compromises, the more like a woman the better.
She said she doesn't want anyone thinking you're anything else but, so
you won't embarrass her when you're out together.  Why is that?  Did
you lose a bet?  Are you planning on an operation to change your sex?
Or is she planning on being the one who wears the pants in the family?"
She smiled at her little joke.

Well, there was news!  That explained a lot about what was happening.
Jill was willing to accept my dressing as a woman if there was no risk
of embarrassment to her.  I just had to do it better, "all the way."
Not look like a man playing a role in drag, or a feminized man, but
look like a real woman.  For the first time that day I started to feel
hopeful.  Maybe our marriage would survive after all.  Maybe it was
worth my trying to help it survive.  Jill had some kind of plan in
mind, and if it allowed me to cross-dress at times I'd go along with it
gladly.  But "the whole foreseeable" wasn't "at times." "I think I may
have won a bet," I replied.  "But can I wear it sometimes to look like
a man?"

"Well, yes, dear, but you'll look like a man with a lady's hair style
if you try it.  I mean to give you a perm, and some clusters of really
cute curls.  If you want, you can set them, and if you don't, you can
reshape them with a little comb.  I'll show you how.  But even if you
brush everything out straight, this hairdo won't be too easy to mistake
for a man's."

I decided to deal with passing as a man another time.  "Your name is
Marianne?" I asked, reading off her name tag, trying to change the
subject.

"Yep, Marianne.  That's what it says, that's what it is, honey.  Mari
to my regulars.  Are you saying you're going to be a regular from now
on?  Because with what we'll do with you today, you won't need to come
in very often any more, or not for too long anyhow.  Maybe a half-hour
a week.  Touch up, re-curling, fix your nails, change of color, little
things like that.  Maybe even every other week.  Depends how perfect
you want to look." She warmed to her topic.  "You watch.  Your wife is
going to love this." She sat me back in her cutting chair, and pulled
strands of my wet hair this way and that.  "You know, you have real
possibilities...."

Three hours later Mari had remade me.  My hair was no longer a mousy
dark brown but a gleam or so lighter, with a hint of blonde or reddish
highlights, though still brown.  It was no longer straight, turned
under at the ends, but looked like a cap full of darling curls, with
sweet little bangs coming down in front, and extending much further in
back, so my nose no longer a little large, but just right.  I was
delighted with it when she took out the rollers and showed me how a
touch of a comb here and there was all I'd need after sleeping on it,
and how to reshape it into springy curls with just a brush and mousse
after a shower, and so forth.  In fact I was so pleased that I said
"Now's fine," without thinking, then realized she had been saying that
little studs would look much nicer than clipons until my hair grew out
a little, and had just asked if she should do the piercing now or wait
till next time.  It was done before I could realize what I'd said.  But
my sudden worry when I saw little gold studs in my earlobes wasn't
enough to break my cheerful mood.  I really looked attractive!  For me,
anyhow.

My nails were deep pink, a shade she said would go with anything and
never look trashy, though she told me I'd need a deeper red if I was
planning to go out formal some time in a long gown.  She laughed when
she said this, and I asked her why.  She replied that the thought of me
in an evening gown had put in her mind an image of my wife in a tuxedo.
She plucked my brows to their previous fine arch, darkened my lashes,
and she put very light "daytime" makeup on my eyes and cheeks, hardly
any.  "You'll do," Mari finally said.  I saw I was no smashing beauty,
but as she looked me over Mari said she felt very good about me.  So
did I. My wife had tipped her heavily to make me look feminine, in no
way a man, she told me.  Now I not only looked no way a man, I looked
like a very passable woman, pleasant to look at.  "From the neck up,"
she added.  I thanked her for the compliment, and could think of
nothing more to say.  She said she'd call me at home for another
session in about two weeks' time.  That sounded promising too.  When I
left the salon I felt better than I had in weeks, maybe even months,
maybe even more.

Without a worry in the world I strolled down the pool patio toward the
restaurant.  Immediately I caught my reflection in a glass door,
hunched over, defensive, and I realized that was how I had walked into
the motel last night.  So I paused, and took some deep breaths.  I
lifted my head high, straightened up, threw my shoulders as far back as
I could get them, and was pleased to see two little bumps hinted under
my shirt.  Then when I next glimpsed my reflection I saw a cute looking
woman with not much waistline and a kind of poodle cut and a bounce in
her step.  I had a cottage cheese salad for lunch, went back to my room
to get my magazines, and had a new thought.  For the first time I might
be able to get away with wearing a swimsuit in public, without looking
like a freak.  I shaved all over again, but everywhere, my legs, chest,
underarms, and arms, places I had learned not to look at when I was
dressing for myself and my mirror.  Then I put on the brand new
one-piece bathing suit Jill had left in my room, looked at myself, took
it off, and trimmed last night's bikini cutting on both sides of my
pubic area.  Then I put it back on.  With its built-in padded bra I
didn't need anything else.  Even so, I slipped on the cover up and
spent the afternoon at pool side reading beauty advertisements.  Every
now and then I got impatient with them, but even turning pages with my
deep pink nails was a privilege, and I felt grateful for some reason.
I needed to know what every girl knows about being attractive,
alluring, ravishing, gorgeous, so I could try.  Like every girl I would
find my own compromises with these impossible ideals, my own style of
femininity, a way to be poised, gracious, and beautiful in my own mind.

People came and went, and glanced at me, or looked casually while
listening to someone talk to them, paying me no real attention at all.
It was a warm afternoon, and I lay in the sun awhile, then fell asleep.
When I awoke I was stretching luxuriously, like a huge cat.  I realized
why.  The bathing suit pulled and stretched and shaped me in a way that
would make any woman feel catlike when wearing it.  It said as much on
a tag still attached when I took it off its hangar.  By the time I
returned to my room it was 5:30.  I ordered a sandwich from room
service, and tried on the different dresses Jill had put in the closet.
There was that darling cocktail dress, high-necked, black, subtly
beaded, almost calling for those red nails Mari had mentioned.
Whatever the evening activities Carl had mentioned, this would do.  By
7:30 I was wearing it, had adjusted my makeup for the evening, and was
back studying the magazine ads, waiting for Carl to show up with my
schedule.  I wondered if he was supposed to be my gentleman escort for
the evening, and where he would take me, and whether there would be
other women there to help me polish my movements and manners, to
perfect my behaviour the way Marianne had perfected my hair, face, and
fingernails.  Whatever lay in store, I intended to be a lady, and
unashamed to be a lady.  I wanted my wife to be proud of me.