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Home My Crossdressing Sissy Husband (by Vickie Tern)

For the next few weeks I encouraged my crossdressing husband to think of our new arrangement as normal. He did everything as usual, but as a woman. Most evenings he’d report that there were no problems, people
seemed to assume that’s what he was. He awoke each morning already
quite pretty, thanks to Doreen’s facial dyes, but we performed our
half-hour beauty routines together anyhow. He needed extra time
with his hairdo, and while he fussed I told him little tales from
my own girlhood, about different exciting first tries of grown-up
things like bras and lipstick, about prepping for dates, things
like that, so he could share my girlhood, not having had one of his
own.

We had a lovely time, chatting together like two girls (or perhaps one girl and one crossdressing sissy) anywhere about almost everything. Except about men — men who did I was sleeping with, men with whom I was cuckolding my sweet hubby.

Then we’d have breakfast and I’d be off for the office, leaving my sissy crossdresser to do his own things. We’d always shared the housework, but since
he had more time available, he took it all over, as he had last
summer too. He spent a lot of time working in his study. I
guessed it was on his “I was a woman for three months” project. I
hoped so, because that would give his new life legitimacy in his
own eyes.

He was no longer my mildly whimsical, lightly ironic, even-tempered
hubby. As a sissy crossdresser maid, his moods varied. Some mornings he’d awaken a little solemn, maybe mournful, maybe impatient, though he never said
anything. I could tell because in that mood he’d never volunteer
to share stories about his day, only answer me listlessly, and he’d
apply his make-up as if it were a boring routine, not an artful
honor. Those mornings he’d always get a pill before I left for
work, if it wasn’t a Saturday when I knew Doreen would be feeding
him one anyhow. I’d tell him to relax by gardening, to put on his
flared shorts and a halter and get into the sunshine and fresh air
and cultivate our flower beds. That he had nice legs, especially
now that they were waxed smooth and Doreen’s treatments had made
their skin so soft, that he should show them off more.

He did. The neighbors saw a lot of my crossdressing sissy husband on those days: a strange blonde woman impeccably made up, moving among our lawns and shrubs
as if in a dream, combing the soil between plants. I later learned
that he’d once gone mall-shopping dressed in those same scanty
shorts and halter — one of our local wives sent a letter to the
editor of the neighborhood newspaper deploring a hussy she’d seen
parading herself in and out of stores dressed that way. My crossdressing
husband looked wickedly pleased when he showed it to me.

But most mornings he’d awaken zestful, choose an outfit for the day
– casual, sporty, or dressy — and do things I’d read about
afterward. He started a journal and left it open on his desk. When I looked into it, as I did regularly, it became obvious that
he was now actively seeking out womanly experiences and enjoying
them, diligently doing his research for his book. His perfume had
become a non-issue, as I’d predicted. He always wore a light spray
when dressed casually and a heavier scent in the evening, but even
when not, his oil treatments infused his skin with a faint aroma. It was so lovely! I’m sure it brightened the moods of others who
caught his scent as he passed them, but of course now it raised no
questions at all. When he went in to use his college’s library, he
showed the librarians his faculty ID card and then proceeded as if
he were the person pictured on the card. They never questioned him
– rather, they assumed he was his own somewhat provocative summer
research assistant, and granted him all of his usual borrowing
privileges.

Once while crossing the quad one of his colleagues in Mathematics
made a pass at him, inviting him to pass some time in his office,
where my crossdressing cuckold husband knew there was a couch. My cuckold told him primly that
he never dated men, that he lived with another woman and dressed
this way only to please her, and that she was his partner for life. All true enough. The man got flustered and practically fled, my cuckold told me.

But that wasn’t the only time he was hit on. He often expressed
annoyance at how bold and persistent some men could be, how
irritating the intrusions on his attention. That was especially
satisfying — he was was learning that men respect their own
lechery more than a woman’s privacy — they were always testing the
availability of anything in skirts. That was certainly true of
Craig until I took to mocking his impotence when we were both
exhausted with fucking and he realized he’d better concentrate his
energies if he ever hoped to get the better of me. Though it was
never true of my cuckold, my one-woman man who was now my one woman
woman.

He ran errands in the neighborhood secure in the knowledge that no
one would recognize him. The genial professor was nowhere visible
in the tallish, brassy, flashily dressed blonde. Sometimes he went downtown to look
about in upscale stores, as he put it to “simulate shopping,”
trying to feel his way into women’s thoughts and rhythms as they
engaged that recreational activity. He’d chat cheerfully with
other women shoppers, with shopgirls, with waitresses, on Saturdays
with Doreen’s manicurist, anyone. He was always friendly, always
grateful for their help, and I think secretly delighted that they
accepted him as one of them. At night he watched the young women
in TV sitcoms to see which of their mannerisms he could imitate and
make his own. He developed the cutest ways of asking questions, or
of indicating surprise, as if he too were a sprightly actress.

I was proud of my hubby. He’d been such a lovely man, and now he
was becoming such a lovely woman!

Some women realized after a while that they were really dealing
with a beautifully disguised man. A few turned away disgusted, but
more were rather taken by the idea. They were fascinated by the
idea of a man who crossdressed because he wanted to be what they already were, perhaps a
transsexual who believed he really was a woman despite his body –
that gave them a sense of privilege, that what they were was
desirable.

Or, they thought him a man perhaps so exuberantly confident of his
masculinity that he wanted to try anything life offers, even living
like a woman. They liked it that he could share their special
concerns and appreciate even their trivial frustrations, and many
regretted that their own cuckold husbands lacked his sensitivity as well as his
courage. My crossdressing cuckold talked about everything with them except his own
boyfriends and he gave them excellent advice about
theirs. He’d listen to them the way women listen to each other,
sympathetically, not like a man who wants to identify a problem,
find a quick solution, and then move on.

He cultivated an impudent personality to go with the look Doreen
had given him, a lightly sardonic, liberated manner, and he enjoyed
what then followed. Some women told him their most intimate
secrets, knowing he’d understand. Some offered to find him dates,
and never understood why he always turned them down. Many just wanted to dress him up, he was so eager to learn about fashion, so eager to put on dresses, skirts, bras, pantyhose, heels….

What kind of man makes a better companion? What kind might make a
better lover? These women found him as attractive as I did, but as
a man who had chosen to live their lives, not just as a female
friend. This wasn’t what I wanted for him. I especially began to
worry when I read in his journal that the salesgirl in a darling
little boutique where he’d already bought a few dresses and a
bustier for me had invited him back to her place after closing
hours for what she obviously hoped would be some private fittings. He’d been unable to accept, that particular time, but he did offer
her a rain check.

I wondered about that, and was tempted to increase his
tranquillizer dosage to keep his penis soft, and I confess I did
just that for a few days. But then all he did was stay home
smiling at the TV or at his own reflection in the windows. And
that was unfair — I didn’t want him merely warehoused for the
summer! So I returned him to his usual dosage, enough to leave him
his mind and energy intact yet keep him moderately content. As a
hot looking woman, or as a man who was dressed as a woman, he was going to
attract various kinds of people, women as well as men. It was
inevitable. That’s just how things are, I realized. And he was
enjoying himself, while remaining as faithful to me as ever. I
liked that. Often, when Craig’s face was buried in my ass because
I’d dared him to taste what he’d just done to me there, and there
was nothing else to think about, I got a warm glow thinking about
my honey and her bees.

Maybe it was unfair to him not to move him further, make him even
more womanly? I realized one day that his journal entries had an
odd tone. He was writing as if his ventures were reconnaissance
missions into enemy territory. He was thinking and feeling like a
man disguised as a woman, a transvestite, or perhaps a sissy crossdresser. This was not what I wanted. If he
thought he was a man, other women might too, and that could lead to
mischief. And I certainly didn’t want to think of him as a man –
Craig was all the man I wanted to deal with. Plainly, I had to
push my crossdressing cuckold further. But how?

It dawned on me only slowly. His tranquillizer pills began to show
some distinct secondary effects. His nipples became noticeably
larger, protrusive, puffed out and incredibly sensitive. I found
in fact that I could make his slack penis drool just by touching
them. One morning when I was sucking and caressing them gently I
noticed him grow raptly attentive to some inner kind of music,
breathing more and more deeply, his eyes closed. Then suddenly he
stiffened and gasped and moaned aloud in a kind of agony, then with
joyous satisfaction. I reached for his cock and found it slick and
slippery, and his balls and belly too. He’d actually climaxed
without my touching him down below at all! My new girlfriend with
his boy’s equipment had actually had a girl’s orgasm! The same as
when I’d fucked his ass with a dildo!

That was as satisfying to me as I am sure it was for him, because
it meant he didn’t need erections in order to enjoy for himself the
erotic pleasure I was getting from Craig. So I wasn’t cheating him
after all. He seemed too embarrassed to mention his inability to
get hard or his nipples’ altered appearance, but I knew he had to
be puzzled or anxious about both. So I raised the topic one
evening while caressing and kissing his new little boobs, his head
flung back on the pillow in ecstasy.

“Being a woman can be just heavenly, can’t it?” I asked.

“Oh, y..y..yes” was all he could gasp.
“It’s a shame that when it’s over, your body will go back to the
way it was. That your clit will become a stiff penis again.”
“Oh,” he said, as I leaned in to lick the fat nub his nipple had
become. “It will? …ooooh! …oh!… That’s a relief… ahhhh, I
didn’t know, I was worried!”
I then began flicking my tongue on one nipple, and teasing the
other between two fingers. He let out a little yip. “But if you
like this you can keep these afterward. They don’t have to
disappear. Do you like this?”
“Oh! Oh Mandy! Oh, yes, yes, I do!”
“Really? Good! Then it’s settled, you’ll keep them.”

I said no more. He was half out of his mind, but he’d agreed to
keep his enlarged nipples. He didn’t know he had no choice of
course

I might have been mistaken, but his rear end actually began to look
cute too! At first I worried about it, but finally I liked even
that. A nice round butt instead of his skinny one, yet another
physical change all to the good. It too would remain when the
summer and my glorious affair with Craig had ended, but I didn’t
mind. Whenever I saw them, his nipples and his ass would remind me
of my wonderful hubby’s unknowing sacrifice of some of his manhood
so I could enjoy another man’s greater manhood guilt-free. And
each day he was getting more and more understanding of my point of
view. Our morning chats really were getting to be like gossip and
giggle sessions between two women.

I couldn’t escape the idea. If his body and his attitudes were
turning the corner from masculine to feminine, I should make some
other changes too. Make him more of a woman, give him a real
figure. In fact give him everything but an actual vagina. Cheryl
persuaded me that a vagina would be too much, it was too dangerous. If Mort had a vagina, she pointed out, he’d feel free to leave her
altogether to live a normal woman’s life. Without one, he’d always
be incomplete, and that was how we wanted our girly men. “But that
doesn’t mean he can’t develop above the waist as we all did,” she
added. “Especially since you say he gets so much enjoyment out of
his titties already.”

That made sense. I was starting to conclude that my cuckold crossdresser needed
breasts. Not just the tokens he was growing, but large, heavy
breasts. Daily, hourly reminders that he wasn’t an imitation but
mostly the real thing, that he had no choice but to think of
himself that way. A resident woman, not just a visitor or a spy.

I’d already gotten him a beautiful pair of curved silicone breasts,
heavy, soft, glue-on prostheses, so he’d appreciate how women feel
about wearing bras, how bras provide essential support yet pull at
the shoulders, So he’d always remember to wear his own bras or else
endure an uncomfortable and absurd bobbling when he was jogging or
doing his morning jazzercise routine. So he couldn’t possibly
relapse and go out dressed as a man when I was at work. But now I
realized that his artificial breasts weren’t enough. Real ones
were better.

I did want him to want them, but I couldn’t figure out how to make
him want them. I couldn’t tell him how Craig did certain things to
mine that drove me wild, in fact led me into chain orgasms by
touching, licking, or sucking my breasts in special ways,
especially my nipples. I did much the same to him as his nipples
grew. But his lacked the heft, the generous, soft, ripe handfuls
of flesh Craig could clasp and lift gently until I couldn’t resist
him and had to climb back onto him until he was into me. My crossdressing cuckold
didn’t have anything like that even though his nipples became
impressive.

I always encouraged him to make love to my breasts, to caress and
kiss and tongue them, and I always made ecstatic sounds suggesting
how that made me feel. And of course I brought him to orgasm
repeatedly with his. But he never envied my boobs. I realized
that on his own he’d never ask for larger breasts. I decided he
had to be granted them as if they were a special blessing, a gift,
as a fait accompli. Then he’d have to accept them, and I was sure
he would. But how?

The perfect opportunity arrived a month into my affair and
my crossdressing cuckold’s womanhood. Craig and I were each due two weeks of summer
vacation. Craig proposed that we sail away together for the whole
time on a yacht he could borrow, to Bermuda and back, just the two
of us alone in a small boat on a wide ocean, naked and in close
quarters the whole time. His intentions were obvious enough. He
wanted to lay serious seige to me, to capture my heart entirely if
he could, so he could then feel free to toss it aside if he wished. He wanted to conquer me. I thought I could do the same with him,
or maybe two weeks of uninterrupted lovemaking would weary both of
us beyond any desire to continue the affair. Or maybe we’d find
that climbing into and around each other as a daily thing
habituated us, build our passion to an intensity that would sustain
itself during the succeeding months of the summer, when we’d be
seeing each other only weekly again.

Well, if I could get my crossdressing cuckold out of town, he’d never know that I
was out of town too! I asked Cheryl how to do it, and she provided
the easy answer. Tell my crossdressing cuckold that he had to get rid of all the
hair on his whole body for good, permanently, excepting only his
Bikini patch and his eyebrows. That the soft, silky skin Doreen
had given him was denied its proper sheen by the hair follicles
he’d unfortunately developed in his puberty. That his natural
beauty required perfect smoothness. That his close daily shave was
onerous for him and scratchy for me, tiresome for both of us. That
he deserved to be liberated from that ordeal so he could spend more
time gracing his eyes and cheeks with shadows and blushes. That he
didn’t deserve the pain of a weekly full body waxing either. That
I’d love him forever if he got rid all of his hair permanently, by
electrolysis and lasers, if he’d make that small sacrifice for me,
no sacrifice really, since since he never intended anyhow to grow
a beard or a moustache. That I didn’t like them.

I told him that there was a special clinic in Texas for
transgendered men where they could render anyone hairless
skillfully, thoroughly, and painlessly in only two weeks instead of
the years otherwise needed. That they eliminated all bodily and
facial hair while their clients were in day-long tranquillized
stupors. I told him I’d make all the arrangements, that all he had
to do was travel there and then at the end of two weeks travel back
looking prettier than ever.

He agreed. “It’s only hair,” he commented. ” No big deal. If
that’s what you want.”

“Oh yes,” I said. “I do!” I certainly did. I told him I could
bear up and live without him for the two weeks, knowing that he’d
be returning to me perfected in his resolve to live as a woman
until fall classes began again. That he really and truly cared
about how I felt.

He smiled, pleased that he’d pleased me.

That same clinic offered other cosmetic procedures I didn’t mention
to my crossdressing cuckold. I phoned them and ordered the full body and facial
depillation for which they were famous, then also ordered large
breast implants for my crossdressing cuckold. On impulse I also ordered a modest
amount of fat redistribution for him, liposuction of fat from his
waistline to his buttocks, so they’d be really round. He’d not
only have smooth skin and boobs, he’d have an incredible ass! Let
him try to be a man like Craig looking like that! I recalled that
first Sunday of our new arrangement, when I’d first seen him
standing naked and contemplating my panties, and I’d realized that
if his figure was less thin, more feminine, more curvacious, I
wouldn’t at all mind. That then he’d be my girl, and Craig would
be my man, and my life would be complete. Best of all, by the time
he returned to full consciousness and to me, he’d be mostly healed. It would be a done deal. I knew him — he’d accept it and decide
to live with it.

My hubby now well tended, I was free to enjoy my trip to Bermuda. It was incredible! We sailed and fucked, sailed and sucked, sailed
and rolled all over each other. I seduced Craig and had his cock
working deep inside me before we’d even left the inner harbor and
set the mainsail, and that set our schedule for the week. In
Bermuda we found a luxurious hotel and never left the room except
for a brief trip when I bought myself some seductive outfits that
had Craig all over me, tearing them off, the whole trip back.
When we returned to port we were even more feverish with desire for
each other than when we’d begun, and could barely unplaster
ourselves. As I lay with my palms flat against across Craig’s
bare, hard, bronzed, muscular chest that final morning, and kissed
him once each on nipples he could hardly feel, I had to smile. Because I knew that at that very moment my my crossdressing cuckold was flying back
to me with a chest as white, soft, heavy, and well-hung as my own. That he now had full breasts suspended from his chest fully
proportional to his enlarged, protruding nipples. I’d seen
pictures of what the clinic could do — he had an ass now too I
knew, buns to die for! We’d shop for tight pants as soon as we
were back together, and then he’d be able to show them to the
world! My girly hubby, who now needed to wear a support bra every
day! I did so want to see him give men erections just by walking
away from them!

Now my sweet my crossdressing cuckold was no way a man. I was free to fuck Craig without a care in the world. I was free to cuckold him with all and every man I wanted. But I’d make sure while my affair
lasted that my cuckold never regretted trading in his penis for a
beautiful figure. It was only temporary anyhow, I told myself.

I did fuck Craig yet again when the boat was finally secured in its
slip and we were free to go below one last time! We stayed for
hours. I wanted to fill my pussy full up with fresh sperm and my
own sweet lubrication to welcome my dear hubby home again! And I
did. This time I had him kneel beside the bed while I lay across
it casually, my feet still on the floor, and I had him push his
face into my pussy and fill his tummy. Then I fucked his ass and
squeezed almost a cupful of Craig’s sperm out of my dildo’s balls
and into his ass. I’d saved it for his welcome home! The poor
dear leaked half the night.

A few days later I read his journal entries of what had happened to
him in Texas. When he’d emerged from his long stupor he knew he’d
be hairless, and he certainly was. But he was altogether
unprepared to see his voluptuous figure. When the nurses helped
him to his feet, there were large, pendulous breasts pushing out
from his chest and then arching delicately down, massive yet
dainty. And his body no longer descended from chest to thighs in
an approximately straight line as men’s bodies do — instead, he
curved steeply to a small waistline, then around and out into broad
hips. He was a girl! No, his cock was still there, bald as when
he was a boy, but it looked small, non-consequential. His shape
seemed as exaggerated as a stripper’s or a porn star’s, no longer
recognizable as his own.

At first he was horrified. But even as he looked he felt his soft
cock begin to stir! He looked so incredibly sexy! He felt turned
on by his own mirror image. Did he want to fuck himself?

No, he told himself, I’m already fucked! But as I read on, as I’d
hoped and expected he accommodated to it. ‘This is no accident,’
he wrote. ‘Amanda wants me this way, and she’s tricked me into it
just as she intimidated me into spending the summer as a woman. But why? Is she a closet lesbian? If she is, I still love her. All she’d had to do was ask me, and I’d have done what she wanted! Well, we’ll see. I trust her. She’ll tell me why she wanted me
this way when the summer’s over and I can shift back to being
myself.’

It was that easy. That was all I had to do. For a couple more
months now I could be a hard-fucking, sexually voracious woman with
Craig and a loving lesbian with my crossdressing cuckold. Then in September we’d
sort things out. That night I found I no longer needed a pillow in
order to give his ass a long, slow, lingering love-fest with his
favorite dildo, all the while I was giving his breasts a taste of
what Craig often did with mine, lifting and shaping and caressing
them with both hands and my mouth. He went blissfully ecstatic. Any lingering resentment he might have felt at being tricked
vanished. When the summer ended, I told him, he could easily have
his breasts removed, but meanwhile they were his to enjoy, my
surprise gift to him. Did he like having them? He did.

And by mid August I was so accustomed to being married to a crossdressing cuckold
with tits that I no longer noticed them. He’d gotten accustomed
too, so much so that when he put on a bra in the morning he’d bend
forward and dunk himself into the cups while clipping the band
behind his back all in a single fluid motion, without thinking. He
was more graceful at it than many women I’ve seen getting dressed. ..

 

THE CUCKOLD’S STORY

 

But if she knew I knew about her uncontrollable passion for this
guy, whoever he is, it would devastate her. She couldn’t handle
it. Between her feelings of guilt, her frustration, her antagonism
toward me for interfering, and her thwarted passion she’d tear our
marriage to shreds. So I need to protect her from knowing I know.

And the fact is, I don’t mind having these boobs. Not having them
but trying to be a woman anyhow has been inconvenient. Now I feel
authentic. They open a whole new world to me. And besides, they
feel incredibly sexy.

And did I mention that I now have a woman’s butt too? I can wear
pants again and never for a moment be mistaken for a man! Those
guys on the street who pinch my ass in passing now really have
something to get their fingers into. But I won’t encourage them.

Mort thinks we should stop seeing each other so often. Cheryl
doesn’t mind the way we’ve been going at it so hot and heavy
lately, and she promises not to tell Mandy, but it’s getting pretty
intense, all this smooching and stroking, all this fingering of
each other’s pussies. Even though the orgasms are fantastic.

I think Mort’s feeling grieved because I won’t suck his clit to
climax even though he sucks mine every time we meet. I keep
telling him I want to be a one-man girl, I want to keep my mouth
faithful to Mandy’s lover’s cum, to respect the integrity of
Mandy’s decision to share it with me, whatever her reasons. That’s
my way to stay married and faithful to her. I wish Mort could
understand that.

More and more I like being a girl. In fact I love it! Especially
now that Marge and Annemarie have accepted me as one of them, and
allow me to get naked and form a daisy chain with them now and
then. We sometimes lick each other non-stop, round and round all
afternoon when we should be doing our proper work. And sometimes
we use dildos on each other. I wish my ‘meat dildo’ as Marge calls
it would get stiff enough to use on them. I love getting fucked.
But I also love just being one of the girls together with them,
hanging out, chatting, just being with them the way Mandy likes to
be with me, she says. And often is, when she has the time. It’s
really lovely.

Last night Mandy set me up to suck a guy’s cock. She sucked
another guy’s, but I think only to encourage me and keep me
company. We found them in a bar. He was a nice man, and he hadn’t the foggiest that I wasn’t a desirable girl. It wasn’t easy for
me, watching Mandy suck off the other guy, I am her crossdressing sissy after
all, and it shook me up so badly I could hardly hold my own guy’s
cock in my mouth. But that’s how it is, she’s faithful to me in
her fashion, and I have to live with it. So now I’m a cocksucker.
She has something else in mind for me too, I don’t know what. Nor
why.

Anyhow, today I called Mort up and told him now it was all right,
I was willing now to go all the way with him orally. We met for
lunch at Les Bergeres and then we went to a motel, and it was
wonderful how we slipped under each other’s skirts and then sucked
on each other’s clits all afternoon, and never even felt the need
to undress! Mine stays soft, but what it can’t shoot out leaks
out, and it all feels wonderful. We arranged to do the same thing
next week, first lunch, then blissfully suck on each other.

Mort is a sweet girl. He’s been such a big help to me, what with
all his advice about girlish mannerisms and makeup and shopping,
little tricks to make a girl’s life easier. And repeating to me
over and over, stay with your wife, wait out the summer. That’s
what he does, in fact that’s what he’ll be doing for his whole
life, not just one summer. He knows it isn’t easy.

Last night Mandy’s boyfriend fucked me. I could tell that’s who he
was, because who else would have dared to do that in our own living
room with Mandy only a few steps away in the kitchen. A setup.
But do I mind? It’s wonderful to be a woman when there are men
like that in the world, I know that now! I don’t blame Mandy one
bit. In fact I’m grateful she really shared this time, her whole
man, not just his leftovers! I’ll try to return the favor some
day.

Now that I’ve been well-fucked I might want to stay this way when
the summer’s over, though I won’t tell Mandy that just yet. She’ll
need time to get used to the idea that she could find herself a
lawfully married lesbian. We’ve agreed already that if I remain a woman, we’ll have casual relations with men whenever we feel the
need. So no fear I’ll ever be deprived of that, now that I know
how it feels.

This morning I told my Dean I’d be returning to the campus this
fall as a woman, if he didn’t mind. He didn’t. In fact he told me
it would be illegal for him to mind, that in fact he was rather
pleased to hear I’d found my true calling, if that’s what it is.
Then he joked that of course now I’m a woman he’ll have to reduce
my salary by one-third to keep it in line with what other women
earn. I told him I was about to say “Fuck you” in response, but
that ladies don’t use that kind of language except for one thing,
and I didn’t want him to think I was propositioning him. Our
regular monthly poker game is still on, even though I’m now a
woman. “Your money’s still good,” he said as we shook hands. He
gave me a courtly kiss on the cheek, too. I better get used to
that kind of thing.

The people at the Driver’s License Bureau were less polite, but

they were efficient, so I now have a changed license with my new
photo. I’m a blonde officially now.

Mandy seems sad. I think she’s feeling the way anyone would when
a grand passion ends. And she still doesn’t know whether our
marriage will also end a few days from now, when all our agreements
end. Poor thing. I’ve known for two weeks now, ever since that
hunk of hers fucked me, but the uncertainty’s good for her. I’ll
try to make it up to her afterward, be her best girlfriend ever and
all. Mort is already pleased, because our little luncheon trysts
together can now become a regular thing. I’m so glad I took his
advice and decided not to force the issue, but instead to stay
married and wait. Some day maybe Mandy’ll feel she can confess all
to me, tell me what she’s been doing this summer and why she
thought she had to feminize me, tell me all about this Craig she
was seeing. The poor dear. But I won’t force her. I love her.
I can wait.

Well, that’s the kind of thing I found in my cuckold’s private
diary. Isn’t he sweet? Isn’t he a self-centered, manipulative,
pompous hypocrite? He knew about me and Craig all along, how
trapped and ashamed I felt, the bastard, and he used me, he allowed
me to feel responsible for doing to him exactly what he wanted me
to do, so he could enjoy the pleasures of unwitting martyrdom,
stoop to become a woman and then rise nobly to the challenge! He
seemed so understanding, so tenderly concerned for me! And all the
while I was feeling so terribly guilty about what he didn’t know,
and what I was doing to him, and what I had to do to him to relieve
my guilt and keep my dread secret safe. But he already knew!

And here he is pretending to be unsure how he’ll decide to live,
maybe leave me, maybe resume his manliness, maybe stay in the sex
I supposedly forced him into, when in fact he’s already decided and
filed the papers and made it official. And meanwhile he’s been
cavorting with Mort, and Marge, and Annemarie, and who knows who
else, not feeling the slightest bit ashamed or guilty. Enjoying
it! And all through the journal he parades his compassionate
understanding and forgiveness of himself and sometimes even of me!

Well, I’m now purged of guilt for my transgressions against him.
He used me as an excuse to drift into different transvestite
humiliation fantasies he’s always had and never shared with me I
guess, different forced submission scenarios. Now I’ll see to it
that he lives in them for the rest of his life! I mean to put him
to the test. When he wakes up, first thing I’ll feed him his last
portion of Craig’s cum, between his teeth, and when he’s swallowed
it all down, yum, I’ll deliver him an ultimatum.

I’ll tell him he really has no choice. He’s been a woman for three
months now so if he’s to live with me, that’s what he’ll have to be
for the rest of his life. Because that’s what he’ll always be in
my mind from now on anyhow. If he goes back to being a man I’ll
always see him as an effeminate facsimile man. I’ll always
remember how pretty he looked in his bras and panties no matter how
manly his appearance, and of course he’ll always have those nipples
even if he tries to get breast reduction surgery. Once my
girlfriend, I’ll tell him, always my girlfriend, and never again a
masculine lover, never ever again the most distant imitation of a
real man like Craig.

That much maybe he won’t mind, since he’s already decided to do me
a favor and live as my girlfriend from now on. But he’ll need to
consider this too. I may be his loving wife, but he knows what
I’ve done, so I’ll always also be an adulteress in his eyes. We
both know that. He’ll always be tempted to get off on the fantasy
of me fucking someone else, and I mean to help him envision just
that. Often.

He won’t mind, not deep down. He really does love the idea, that’s
why he didn’t insist I stop the moment he saw what I was doing, saw
that I was obsessed with screwing Craig over and over. He didn’t
feel broken up at all! That’s how come I was able to emasculate
him so easily and feminize him so thoroughly, and that’s why week
after week he meekly licked up Craig’s spunk as if he didn’t know
what it was! I was right, he should be a woman! As a woman, he’ll
never need to compete for my affections with the Craigs of this
world, and he should know this. He should also know that as a man
he’ll always be nowhere, out of the running.

So as he likes to say, he has no choice. Those are the paths we’ve
each chosen to walk, me forever a passionate adulteress, and him
forever a feminized crossdressed cuckold. So be it. I can’t ever again live
with him as a man.

But as a woman I can still respect him. Respect her, I mean, even
admire her. And love her, love her deeply even. She’s still the
girl I married, gentle and clever, and a wonderful companion.
She’ll always be my favorite cuckold. I’ll never have a better,and I’ll never want one!

That’s what I told my cuckold later that day. For once she was
genuinely remorseful. She fell into my arms in tears, and we then
discussed the whole matter slowly and carefully. I showed her
everything I’d written, and told her the rest, and we talked about
alternatives. Leaving me was out of the question for her,
unthinkable, she loves me, she said. Meaning perhaps that she’s
addicted to what I’ve been doing to her for the past three months,
she loves her feminine submission fantasies, but I’m sure that some
of it is genuine love, that she cares deeply for me. In the end
she agreed to remain a woman, and that’s what she’ll be from now
on, without pretending this time that it’s all for my sake.

Our marriage is more important than anything else in her life, she
told me, and she’d do anything to preserve it. I believe her.
“Even cut off your balls?” I asked her on impulse. She already
has, very nearly, figuratively speaking, I was thinking. I
insisted that she nod ‘yes,’ and slowly, she did just that

.

Yes! The poor dear. “It must be terrible to be obsessed like
this,” I told her. “But we both have to ride it out, don’t we.
And hope. Then when it’s all over, we’ll be able to see what’s
left.” Those words seemed vaguely familiar to her, but all she did
was nod again.

So she’ll start on proper hormones, and in the not-too-distant
future we’ll get her a proper vagina to please the men we’ll
occasionally pick up and fuck when one of us gets the urge. As for
sucking my cunt when it’s dripping cum, I always did love seeing
her wide eyes staring up at me while those pillowy lips were
pressed against my own lips, and nowhere in that journal of hers
did my darling ever complain of indigestion. She’ll have
opportunities.

My sweet, beautiful crossdressing cuckold. My lovely girl! I do so love her!
From now on I intend to live guilt free, and my darling will live
that way with me. I’ll spare her all burdens of choice. Does she
have any choice anyhow, now?

Oh yes. When I got to the office the next day, after kissing my
lovely crossdressing cuckold goodbye at the door and reminding her to make some
new appointments with Darleen, I found a callback from Craig
waiting for me. We talked business a while, and then we talked
about the summer. He still thinks he got the better of me, all in
all. I still think I can prove that he’s wrong, and one of these
days I mean to do just that, and I know just how. I mean, I still
have more of those pills, and my sissy cuckold’s ass and mouth still yearn
for Craig’s cock, don’t they, and hasn’t Craig already offered that
cock to both his ass and his mouth? In return, Scotty can let Craig
practice cocksucking his limp dick, if I can set up just the right
circumstances. If Mort’s willing to move over and make room. Then
from that humble beginning maybe I can move him on to bigger things.

Yes! Maybe even get him to love other men’s cum. my cuckold does.
We’ll see.