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A Great Letter to a Cuckold

Dear Wimp,

So you are Mary’s husband, the loser, the wimp, the
shrimp-dick that I’ve heard about. Well, I’ve got good
news and bad news for you, wimp. The good news is that
until last week, Mary had been faithful to you. Faithful
for five years of marriage. That’s almost a miracle.
That such a drop dead, knock-down gorgeous babe like Mary
could have remained faithful to a wimp like you for five
minutes is hard to believe. It just shows how religious
she really is. And to think that a girl like that was a
virgin when she got married. By the way, she told me how
with your limp dick, you tried and failed several times
to break her cherry on your honeymoon, and she finally
had to do it for you with her own finger. Even with her
religious devoutness, how could she have remained
faithful to you? Of course, she really didn’t know any
better. You couldn’t turn her on, so she figured she
just wasn’t highly sexed. Oh, brother!

Anyway, the good news for you is that until last week,
your wife had been faithful to you. Until then, you were
the only man who had ever fucked her. Which is to say,
she had never been fucked by a MAN. The bad news, you
can probably guess. Last week, I cuckolded you, wimp.
That’s right, I gave your beautiful Mary the kind of
fucking she deserves and couldn’t get in a million years
from a wimp like you. Mary’s still your wife, but she’s
my woman and I’m her man.

Right now, you probably think this is some incredible
hoax. But if it’s a hoax, how did I know about you being
unable to deflower your wife? To set your mind at rest,
why don’t you take this letter right now to Mary. Ask
her to look at what an incredible prank someone is trying
to play on the two of you by sending you such a letter.
Go ahead and ask her. Then you can read the rest of the
letter in the proper frame of mind.

Okay, Wimp, did you show her the letter? And the minute
she saw it, those beautiful blue eyes of hers dropped to
the floor, and you saw tears rolling down those soft,
soft cheeks, right? And finally she looked up at you
through those eyes sparkling with tears, and in a voice
you could hardly hear, she said, “Yes. Yes. I’m so
sorry, I’m so, so sorry, but every word is true. God
knows, I don’t want it to be true, but I just can’t help
myself.” Am I right? Right. And then you felt your
stomach drop to the floor, right wimp? Oh, how I regret
not being able to see your shit-eating face when Mary
dropped that blow on you just now. But don’t feel sorry
for me. I’m getting pleasure just thinking about it, and
thinking about how you are going to feel, reading all the
wonderful details I’m about to give you.

First, a bit about myself. I think that’s only fair, so
that now that you’ve lost your wife to another man, you
can assess your chances of winning her back. Do you
think you can compete with me, wimp? (By the way, when I
say you’ve lost her, I don’t mean you won’t be able to
live with her. It’s just that as I said above, she’ll be
my woman–one of my women, I should say–and I’ll be her
man. Her only man! And you’ll be shit! At the end of
this letter, I’ll lay out the conditions under which
you’ll be allowed to go on living with Mary. They aren’t
conditions that any real man would consider accepting for
a minute. But obviously, what a real man would do has
nothing to do with what you will do. You’re so attached
to Mary, that she’s certain you’ll agree to anything, no
matter how humiliating.)

To start with, I’m 42 years old. So, perhaps you think
you have the advantage of youth, since you are only 34.
But then, Mary’s only 25, so the difference doesn’t seem
that great from her perspective. And I’m so much more
fit than you are. You are five feet, five inches, five
inches shorter than Mary. And your five feet, five
inches, are composed of pure flab. Mary showed me a
picture of you in a bathing suit. What a shapeless mess
you are!

I am SIX feet, five inches, a full foot taller than you.
Literally as well as figuratively, Mary looks up to me
and down at you, wimp. At 190 pounds, I’m the same weight
as you. But what a difference! You could look with a
magnifying glass and you wouldn’t find a speck of flab on
my body. I have dark hair with just a dash of gray, and
people tell me I have movie star looks. But perhaps you
think I’m exaggerating.. Why don’t you go ask Mary to
show you the picture of me in my dress suit. Go ahead,
before you read any further..

Why the crestfallen look, wimp? So I wasn’t exaggerating
a bit! In fact, I was being modest, wasn’t I? Guess
what, wimp? Throughout this letter you are going to be
thinking I must be exaggerating, but you are going to
find out that every word is the truth. The painful,
stinging truth, wimp.

Well, looks aren’t everything. Let’s see, Mary told me
you graduated from junior college, with a degree in
bookkeeping. You’ve got a crummy job as an insurance
actuary, earning $30,000. Your chances for promotion to
any significantly better job any time in your career are

I went to college at Yale, got a Ph.D. in economics at
the University of Chicago, and a business degree at
Harvard. I finished first in my class by a substantial
margin at each of those places. I then went into venture
capital and hit Silicon Valley just at the right time. I
think I can claim to have been a success. Successful
enough, at any rate, to retire seven years ago at the age
of 35, after I had made my third billion.

Not that I’ve completely detached myself from the world.
CEO’s of Fortune 500 companies and politicians in both
parties are always kissing my ass–sometimes literally–
because they want my help or advice on one thing or
another. And I’m well known in the world of cultural
affairs. Every major arts and cultural organization in
the country has asked me to be on its board, though I’ve
accepted only a select few of the positions that were
offered. So when she’s around me, Mary meets the most
successful, the most glamorous, the most sophisticated
people in the world, and she participates in
conversations that you wouldn’t even be able to
comprehend, wimp. Now let’s compare. Mary tells me your
main interest in life is your bowling league. You think
you are going to win back Mary’s affections by impressing
her with your bowling scores, wimp, when with me she
meets Senators, CEOs, movie stars, and Nobel Prize

Even though I keep a hand in world affairs, my main
pursuit since retiring has been man’s greatest pleasure:
Seduction! I love the feel of women and of sex. I love
the desire that women feel for me. I love overcoming
them and holding absolute power over them, the sense that
I am irresistible to them. And the power they give me
over their men!

Now you may find this hard to believe, wimp, but I’ve
never failed. I’ll target any beautiful woman I see, and
I always fuck her. Always. So I look for challenges.
Virgins, of course, are lovely. I guess I’ve popped a
couple of hundred cherries, probably more. But people
who think seducing a virgin is the ultimate pleasure are
wrong. Very wrong! The ultimate pleasure is being the
first to seduce a married woman. Especially if she’s
extraordinarily beautiful. And if, out of religious or
moral convictions, or love, she’s never dreamed of
cheating on her husband. If the idea of even thinking of
having sex with another man would strike her as
incredible and repulsive. In short, if she’s a woman
just like Mary. So seducing Mary was a rare pleasure for
me, wimp, and now I’m going to tell you all about it.

Mary has told me that in order to maintain even a
semblance of a middle-class lifestyle, she had to go to
work to supplement your measly income, wimp. Since she’s
got much more intelligence and energy and imagination
than you’ll ever have, it’s no surprise that soon she was
earning more than you. And getting more responsibility.
Including business travel. Of course, you never worried
about those business trips Mary was always taking. There
was no need to. Prim Mary, so religious and so moral and
not even aware that she was married to one of the all-
time wimps, would never think of being unfaithful. Well,
you were right to be confident, wimp, because she never,
never would have thought of it. Not until she met me,
that is!

Remember that business trip she took back in June? She
was part of the team trying to sell consulting services
to a big city government. It was a deal in the tens of
millions, and the mayor asked me to come along to give
him some counsel. Since I had fucked the mayor’s wife
and plucked his pretty 14-year-old daughter’s cherry the
day before, I figured I owed him something, and I sat in
on the meetings.

The meetings were dull. I could see in five minutes what
the issues were going to be, and what the solutions were.
It took the rest of those bozos five hours to figure it
out. If Mary and I hadn’t been there, it would have taken
them five weeks.

I was attracted to Mary immediately. First of all, she
was obviously brighter than anyone else in the room.
Second, she was a babe. That silky brown hair, hanging
straight down to her shoulders! Her beautiful baby
blues! The softness of her skin and the sweetness of her
mouth! Her neck! You know, Victorian novelists used to
talk about women having beautiful necks. (Actually, you
probably don’t know, since it’s unlikely you’ve ever read
a novel, other than porno perhaps.) I don’t think I’ve
seen more than five women in my life who I’d single out
for having a beautiful neck. But Mary is definitely one
of them. Her neck is so long and graceful.

Now underneath her neck, she didn’t show much. She wore
one of her typical dresses, one that covered everything.
But a tent couldn’t entirely conceal Mary’s charms, and
the prudery of her dress was a great sign, so far as I
was concerned. This woman wasn’t on the prowl. It would
take overwhelming desire before a woman like her would
succumb. And that was fine with me.

When the meeting was over, I asked Mary to have dinner
with me. She refused point blank. I mean, wimp, she
really was being faithful to you! But I told her I had
the penthouse suite in the ____________ Hotel and that
she really ought to see the view from my rooms. She knew
that was the best hotel in the city and had never been
inside it, much less in its most expensive suite. She
couldn’t resist the bait. She agreed to come up for a
drink only, and on the condition that I not misinterpret
her going up there. I assured her my intentions were
strictly honorable. And wasn’t I telling her the truth?
There’s nothing dishonorable about cuckolding a wimp like

Mary was suitably impressed by the suite. The living
room, she said, was larger than your entire house. And
the view is as fine a cityscape as you can find anywhere
in the United States. There were a large number of phone
messages that had piled up during the day. I didn’t know
what they were but I played them on the speaker, figuring
Mary might like to hear them. They included a message
from the President of the United States–it was his
voice–two Senators, three CEOs, a Pulitzer Prize winning
writer, and two well-known movie stars, all imploring me
to get back to them ASAP. There were also several
messages from women, begging me to come see them soon
because their husbands just couldn’t satisfy them the way
I do. A couple of those were also movie stars, probably
women you’ve fantasized about while jerking off. Some of
them used very explicit language and graphic
descriptions, and Mary blushed like crazy. But I
appreciated the free advertising.

It would have been the easiest thing in the world to fuck
Mary right there in my hotel suite, wimp. But she was
special, and I wanted to enjoy some anticipation. I
contented myself with a long, loving French kiss. Oh,
how sweet was the taste of her lips!

“Harry,” she said, when we finally broke that kiss, “I’ve
never met anyone like you. I’ve never felt this way.”
She hesitated but then, struggling, said, “You can do as
you wish with me.”

I kissed her again.

“You’re one of the most beautiful women on earth, Mary,”
I said. “And very special. I don’t want to lead you
into doing something you’ll regret.”

She was moved by my gallantry. What a joke! She kissed
me again, passionately, invading my mouth with her

“But I must see you again,” she said.

I told her to tell her husband–that’s you, wimp–that
she had another 5-day business trip the next month. I’d
meet her at the airport in your home city, and we’d skip
over to Italy for a few days in my villa over there. She
was thrilled.

So a week ago Monday, when Mary told you she was off to
Chicago to work on another deal, in fact she met me at
the airport. We entered the newest and most luxuriously
furnished of my three Gulfstream private jets and took
off for Italy. Aside from the pilot and co-pilot, there
were four gorgeous stewardesses just to take care of the
two of us. Mary was impressed. She looked even more
beautiful than I had remembered. To think that this
priceless gem of female beauty had lived for twenty-five
years and been wasted on you, wimp! Well, that was about
to change in a hurry.

The only thing that bothered me slightly was that
seducing your wife would be so easy. She had already
told me in my hotel suite a month earlier that I could
have her. Don’t get me wrong. Fucking your wife Mary
was going to be a rare delight, under any circumstances.
I just would have liked some more resistance, that’s all.

So I was delighted when, after we had taken off and were
sipping glasses filled from a newly-opened $1,500 bottle
of French champagne, she said she had something serious
to tell me.

“Harry, I’ve hardly been able to sleep from the shame of
what I said to you last time. Thank God you were gallant
enough not to take advantage of me when I lost my head.
For that alone, I’ll never stop admiring you, Harry. You
see, what I said about how wonderful you are, and how
wonderfully I felt, that was all true. But I’m a married
woman, Harry. I’ve never been unfaithful to my husband.
Except for that crazy moment, I’ve never thought of being
unfaithful to him. I never, never will do it. Please
understand. If you want to order the pilot to turn the
plane around you’d be completely within your rights.”

These words were music to my ears. Oh, fucking your wife
was going to be such a pleasure, wimp. I knew at that
moment that I’d be remembering the words she had just
spoken when she begged me to put my dick in her pussy.
And I knew she would. They all do!

“Darling Mary,” I said. “Wonderful Mary, your company is
all I need to delight me. How lovely it will be to be in
Italy with you. And as I told you, I wouldn’t dream of
pressing you to do anything your convictions tell you not
to do.”

She gave me a warm, lingering French kiss. Oh, what a
beauty she is! It was a struggle to keep my dick from
growing. But I have complete control of my equipment,
and I wanted to wait for the right moment for her to
become aware of my hard-on.

We landed on the private airstrip on my estate in
northern Italy, which is on the Riviera near Genoa. I
have twenty-five luxurious estates or residences in
various major cities and resort areas, but I picked the
one in Northern Italy for seducing Mary, because I
figured she’d like one of the cozier ones. I won’t go
into details, which you wouldn’t understand anyway, wimp,
about the villa. Suffice to say that if you go to the
public library and check out almost any textbook on the
history of art, you’ll see it pictured as the finest
architectural example of the baroque style in Italy. It
has forty rooms and I maintain a staff of 35, including
about a dozen strikingly beautiful young women who
provide.. Well, let’s say “special services.” The rest
of the staff is high priced and highly professional.
Mary had two ladies’ maids on duty through her entire
visit. Her every whim was immediately attended to.

We landed late in the afternoon and it was a beautiful
summer’s day on the Italian coast. I dismissed the Rolls
Royce and driver, and drove Mary the five miles along the
Mediterranean coast to the villa in one of my Jaguars.
Our luggage was brought right up to our rooms and
unpacked, and we followed to freshen up. When I rejoined
Mary in the dining room a half hour later, I asked her if
her suite was suitable.

“Oh, it’s simply marvelous. I’ve never even seen such
luxury, much less experienced it. And the view of the
coast is simply breathtaking.”

“And were the servants satisfactory,” I asked, struggling
to avoid smiling. She blushed.

“I- I- I’m just not used to that kind of service,” she
barely managed.

“Why, what do you mean?” I asked, feigning ignorance.

“Wh- When I went to the bathroom, they came with me, and
they..” She was bright red, and couldn’t go on.

“Yes, they cleaned your most intimate parts, didn’t they?
They are well trained. But did you object to that?”

She wasn’t sure what to think, but she must have assumed
it was a European custom, and didn’t want to seem

“Oh, no. It’s just that I’m not used to such luxury.”

I gave her a long, wet kiss. I knew that in addition to
gently washing Mary’s pussy and asshole after she used
the toilet, the maids also had fluffed up and lightly
powdered and perfumed her pussy hair, just as I like it.
My staff is always impeccably trained. As for me, in
addition to receiving similar servicing from my two
regular maids, I had dumped a couple of huge loads of
sperm deep in the cunts of two particularly lovely
members of the special staff. I needed some relief
after all those hours, especially being stimulated by the
sight and the kisses of your wife.

We sat down for dinner. She said it was the most
marvelous meal she had ever had. Which, of course, it
was! We were enjoying an after-dinner drink, a rare
brandy. Each drop was more expensive than the entire
bottle of champagne we had had on the plane.

When we were finished, I led her into the living room.
The room is almost three times as large as the living
room in the hotel that she had admired the previous
month. The furnishings are in the baroque style, but
perfectly maintained in every detail. The view of the
coast faced in a different direction than the view from
her bedroom, but was equally magnificent. We sat on the
sofa, which, she said, is larger than the bed she has
shared with you at home, wimp.

We had another hour or so of small talk. Mary is
intelligent and enjoys talking about many things. But
you wouldn’t know, wimp, because she doesn’t seem to care
much about bowling scores, and what else would she talk
to you about?

But after about an hour there came a moment when our eyes
met, and there was a pause.

“Mary,” I said, “you are one of the most attractive women
I’ve ever met.” I gave her a long, affectionate kiss,
enjoying the sweet, sweet taste of her mouth. Can a wimp
like you even appreciate such a woman? And what a woman
she is!

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