When my good friend Clinton Crayle disappeared last year, it
fell to me, the chronicler of his adventures, to handle his
affairs. Acting on sealed instructions, I went through his
voluminous files, disposing of anything that could in any way
prove embarrassing to any of his former clients, and, incidentally
searching for any clues as to his present whereabouts.
After careful consideration, I decided that some of the
letters from those files, suitably edited to protect names and
identities, might interest our readers out there.
As to what I found out about Mr. Crayle himself, well, more
on that later perhaps. For now, the letters below, taken from his
secret files, will have to do….
Dear Mr. Crayle…
This may sound like some weird joke or gag letter, but I hope
you’ll believe me, it’s true… Hardly anyone here believes
anything I say anymore and it’s so frustrating! Also sorry this
will be so short, but I don’t have a lot of time to write. I just
hope I can get an envelope to go with this stamp that I found and
mail this out to you…
Anyway, let me tell you quickly how I got where I am…
I was prowling the singles bars when I met Judy, and did she ever
look great in her Nurses’ Uniform! Maybe something just a little
strange about her expression, but in that light, who could say.
And who cared, when her body promised such delights! I was
scarcely listening when she told me she was a Student Nurse at the
plush Sanitarium for Women on the outskirts of town, but when she
realized she was late getting back to her room and might be
Disciplined, I agreed to drive her out there….
Once there, she seemed awfully grateful, and I was surely Hot
to Trot, but she didn’t want to Do It there in my BMW (who could
blame her?) so she suggested we try to sneak up to her room….
It seemed like quite an adventure, climbing up a tree outside
the fence around the grounds and sneaking across the roof to get
to her open window. As we undressed, the brandy she kept in her
room, combined with the drinks from earlier that night, was
certainly potent: TOO POTENT! The next thing I can remember, it’s
morning, and Judy shakes me awake. Big trouble coming; An
Inspection, and she can’t have a man caught in her room. She’s
already hidden my clothes (actually, I learned later, she dumped
them in the incinerator!) but what to do with me?!?
That’s how I let her talk me into this: Body shaved, hair
moussed, eyebrows plucked, a trace of makeup… She gave me a
cotton dress and slippers like the patients here wear, and to my
surprise I looked enough like a woman that I could just wander
around the grounds and try to blend in until she could get back to
It was evening by the time we could get together, and was I
furious when I learned that she’d destroyed all my clothes! We
quickly agreed that she’d have to go to my place and get me some
more…. only she wasn’t allowed off the grounds till next
weekend – so what could we do with me in the meantime? I couldn’t
pass as a woman like this very much longer!
That’s when she told me about the M-X shots that they give to
some of the women here who suffer from “Gender Confusion”. It’s
supposed to make them look more feminine, I guess. Anyway, she
talked me into taking them. I didn’t want to at first, of course,
but when she mentioned how she might be fired and I could be
arrested for sneaking in here, well….
Those shots certainly worked as advertised! Even more than I
had figured on, in fact! My breasts are large, firm and well-
shaped – just like my bottom! And the hair we shaved off that
first morning still hasn’t grown back! I’m not sure just what this
thing is that Judy glued on over my crotch, but it looks just like
a female pussy, and it’s on to stay until someone applies the
solvent! It didn’t even come off in the shower….
Oh yes, the Shower. I got roped into a volleyball game with
some of the girls, and afterwards we showered off together. Some
of those bods weren’t bad at all, and I guess you can’t blame a
guy for staring. I mean, I hadn’t really had any sex for some
time, and being surrounded by all those naked women, well maybe my
hands did roam a little….
Only they took it the wrong way and started calling me queer.
After all I’d been through, I wasn’t going to take abuse from a
bunch of weird women. One thing led to another, and I guess I
threw the first punch….
The wrestling match that followed was less painful than
humiliating. No matter how I tried to grab this one girl, she kept
slipping away, and no matter how I struggled, I couldn’t get out
of her holds. She’d tie my arms in knots and then pinch my tits,
or pin me down and playfully bounce up and down on my face! (Did I
mention we were both still nude?) Or tickle! By the time the
Nurses arrived (including Judy) I was screaming hysterically and
everyone else was looking innocent….
I guess that’s how I landed here in this straight-jacket. A
good looking but rather butch Nurse comes and feeds me and
supervises my toilet. She also did a work up that showed my
hormones were off (for a woman, that is) and put me on a new diet
that’s supposed to make me more womanish. Judy comes when she can,
but there’s not much she can do. She did get me to sign some
papers, changing my name and committing myself for treatment here,
so that she won’t get in trouble and I won’t get arrested, and she
had me sign over my bank accounts and stuff to her so that she can
run my affairs for me until I get out….
The problem is that no one much wants to let me out! They
keep asking me what I can remember about my background, where I
was born, what my childhood was like, and that kind of thing, and
of course, since I’m not really Who or What they think I am, I
don’t know any of the right answers! I tried telling them the
truth once, and all it got me was a week of Heavy Medication!
That’s over now, thank heavens, but ever since then, they keep me
Naked in this padded cell, except for brief exercise-walks around
the grounds, when I’m “allowed” to wear a Harness that doesn’t
cover a thing (“Now, now, Dear; We’re all Female here, after
all!”) and walk ahead of my Nurse on a Leash!
So you’re my only hope, Mr. Crayle, that is if my plan to
smuggle this letter out of here works! I’ve heard you specialize
in cases like mine, and I’ll gladly pay your fee if only you’ll
come and get me out of here….
I’ll try to get some kind of envelope and sneak this into the
mail tonight. Please Hurry!
EDITOR’S NOTE: Crayle’s notes indicate that this was signed with a
male name, but that there was no return address on the envelope
and the postmark had been smeared by rain! Clinton did check with
a few all-female asylums, but without the poor guy’s feminine
alias, he really had no lead to follow, so the case remains
Dear Mr. Crayle,
About a month ago, my wife Karen and I, and a bunch of our
wealthy swinging friends, were all invited to one of Bernice’s
wild parties, with prizes going to the kinkiest get-ups.
Naturally, Karen and I wanted to take First Prize, so we did
a little snooping around to find out what some of the other
couples had planned.
Most of them were coming in rather standard Kinkwear, with
lots of leather for the men and silk for the women. There was to
be the usual complement of Barbarians, Slave Girls and Harem
Dancers, but some of our friends had shown quite a lot of
imagination in selecting their disguise and Bondage Gear!
One couple, a rather attractive pair named Bill and Irene,
had worked out a variation on the old-fashioned Horse Costume;
Only this one was a body-stocking made of strong open-weave black
net, with a corset that locked Bill’s arms to his sides, and
thigh-length boots to keep him on his toes. He was to be the rear
end of the Horse, with his face securely strapped into Irene’s
cushy bottom. The result was more of an androgynous centaur than a
horse, what with Irene’s breasts and pussy exposed by the body-
stocking, as well as Bill’s private parts and ass, and since Irene
was also fitted with an arm-locking corset, just like Bill’s they
would both be quite helpless and very very vulnerable.
Naturally, with this kind of competition, Karen and I had to
wrack our brains for something really Unsurprising. Which is how
she came up with the idea that she and I attend as Adam and Eve…
Shots swelled and shaped my chest into impressive female
breasts, depilatory and skin lotion rendered my flesh soft and
smooth, and an elaborate triangular wig fastened over my crotch,
seemingly transforming my male parts into those of a woman. I
never knew my legs could look so long and sexy! And once Karen had
worked on my face and hair, I must say I made a very attractive-
As for Karen herself, a double-ended dildo, held in with
flesh-colored rubber straps, and another, wider, set of rubber
straps to mash in her breasts, were just the Start. She covered
all this with the same skin-tone latex that held my crotch-wig on,
leaving small holes for the nipples to stand out on her now-flat
chest, the way a man’s would, covering and concealing the soft
rubber straps until they were completely undetectable, and she
looked like a quite convincing, if rather soft featured, male.
Well, by the time we’d transformed ourselves into each
other’s sex, we were more than fashionably late getting started.
So we put trench-coats over our nudity, (we were going as Adam and
Eve, after all!) and drove off towards the party.
But then, as we were taking a short-cut through a seamy part
of town, my Porsche broke down!
Not really thinking, still wearing only Karen’s trenchcoat, I
stepped into the closest bar to call for help. Since I had my
wallet and credit cards in my coat pocket, and we belong to an
exclusive Auto Club, I soon had help on the way.
Then, I realized I had to take a leak. Absent-mindedly, I
went into the closest Restroom, not realizing until I got in that
I’d have to sit down to do my business. Well, the room was
deserted and my need was urgent, so I draped my coat over the wall
of a toilet stall – the stalls had no doors, by the way – and got
Well, you can imagine my horror when the door flew open and
two burly guys tottered in! Their bleary eyes flew open as they
fastened on me, squatting there, knees wide and breasts completely
exposed, and I clapped my legs together and crossed my arms over
me for cover. Somehow, it hadn’t occurred to me that this was a
MEN’S Restroom, and I would look terribly out of place in my
present condition. But the looks on the faces of those guys was
sure a reminder! Before I knew it, they were standing right in
front of me, leering down at my fleshy female curves – and one of
them had my coat!
Meanwhile outside (I later learned) the expensive car and
male-ized Karen’s callow good looks had drawn the attention of a
bunch of prostitutes, who sized her up as a rich young guy looking
for a little action… every hooker’s dream! Swarming over “him”,
the brassy tramps quickly discovered “his” lack of clothing,
relieved “him” of even that, and proceeded to tease a bit.
(Perhaps I should mention here that the double-ended dildo
Karen wore was filled with shampoo, so that a squeeze on the
erect-looking exposed end caused a thrilling ripple on the end
buried inside her! I can just imagine how it must have felt to
have a bunch of women stroking her bare flesh all over while they
fondled that thing!)
By that time, though, I had enough troubles of my own!
Thinking quickly, I’d decided that the only thing to do was to
pretend that I was one of the topless/bottomless “waitresses”
working in that dive. It was tough taking my hands down from in
front of me and standing up in front of those guys (a few more
came in) but I told them in my toughest female voice that I was
tired from dancing all evening, and would they please act like
gentlemen and give me my coat so I could get home?
Well, I think they were about to do it, when one of them
protested that he hadn’t seen me dance, and the others agreed that
they hadn’t had the pleasure either, and I ended up having to get
up on the back of that cold, hard john and shake my tits and ass
for all of them while they kept Time clapping their hands!
And as if that wasn’t bad enough, the noise drew the
attention of the guy who owned the Bar, and when he came in and
saw me apparently taking trade away from his girls… well, he
didn’t want to say anything in front of all those horny drunks,
but I could tell from his eyes he was pissed off!
That’s probably why he started calling me Trixie and told me
it was time to get back to work. Someone lifted me down off the
commode and I was actually passed from hand to hand, wiggling and
squealing as fingers pinched my tits and probed my nether parts,
back to him. His grip was like Iron as he took my elbow and led me
back to his office, and where my coat got to, I’ll never know!
All this time, of course, Karen was having problems of her
own: Having taken her clothes, the hookers were a bit surprised at
the smooth, hairless skin and soft features on this “guy”, and
Karen’s voice wasn’t much help either. They asked if “he” was gay
and looking for men, and I guess she said Yes, hoping they’d go
away and leave her alone. They said they could oblige her, for a
small fee, and she stammered something that they took for another
So they pulled her nude from the car, took everything of
value they could find from it, and then, crowding around so she
wouldn’t be seen, walked her several blocks down the street to a
Gay Bath House, where they sold her to the Owner as a Towel Boy!
I didn’t do any better. Back in his office, the Bar Owner
silenced my pleas and protests with a very simple threat, and, as
I cowered there, all feminine and naked in front of him, trying to
cover my huge tits and furry pussy with my hands, he got on the
phone. Ten minutes later, two big, bored-looking guys came in,
looked me up and down, handed him some money and then carted me
off to a Massage Parlor!
Karen and I got home about the same time the next day, both
looking a bit dazed. I told her about my evening, and wept
bitterly when I got to the part about having use my mouth and
hands on strange men all night in that Massage Parlor, and the
demeaning outfits I’d been forced to wear. one man had even paid
extra to spank me first!
Then Karen started telling me about her escapade, and to my
surprise, she sounded almost ecstatic! She said a lot of the guys
in the Bath House were really nice looking, and that all of them
were very gentle and considerate with her. Once she’d got over her
initial fright at her strange surroundings, it got to be kind of a
kick, fooling all these horny guys and getting so much loving
attention from them… and she’d lost track of how many times
So both of us had spent the night with our genders crossed,
servicing men – and she absolutely loved it!
That’s my problem.
Ever since that night, Karen’s been gently hinting that we
might do it again sometime. Naturally, the idea of such a thing
disgusts me, but from the look in Karen’s eye, I’m beginning to
think that I may not have much choice. She’s a clever, forceful
woman, used to getting her own way, and I’m worried that I might
find myself one evening transformed again and on my way back to
the Massage Parlor.
One other thing I’ve noticed is that the hair we creamed off
my body hasn’t grown back yet, and my voice and muscle-tone seem
to be getting softer, and my nipples larger grand more sensitive.
Mr. Crayle, could Karen be putting anything into my food? And just
last night I found some Condoms in her purse!
Can you help me?
EDITOR’S NOTE: Attached to this letter is a copy of Clinton
Crayle’s reply, offering the names of doctors, psychologists and
marriage counselors who might be able to help. There’s also a leaf
from Crayle’s appointment book, indicating that he had scheduled a
personal interview to follow up. Underneath the scheduled
appointment, in Crayle’s handwriting, are the words “No Show”. I
wonder what happened?
Dear Mr. Crayle,
I come from a very large and wealthy, if somewhat eccentric,
family, so I wasn’t all that surprised last year on my 21st
Birthday, when I inherited an expensive Bordello from my late
Uncle Otto in Amsterdam. Having no other responsibilities to speak
of, I arranged my affairs here in the States and flew off to the
Netherlands to inspect this windfall.
I’m no prude, and I must say that I certainly enjoyed the
attentions of all the young ladies who had worked for Uncle Otto
but now worked for me; so much so, in fact, that I decided to stay
on and try running the place for a bit. I even made friends with a
competitor of mine from down the street, an attractive but tough-
as-nails lady named Vanquisha who specialized in S/M and that sort
I was also rather taken by my female second-in-command, Hedwig
Astin, a tall, knowing, incredibly talented blonde who had ways of
turning me on that surprised even me!
It was Hedwig, I guess, who led me into developing a fetish
for female attire. She introduced me to the feel of silks and
satins on my skin, caressing my rump, tickling my nipples,
cradling my Privates in a sensual embrace, even swishing about my
legs, and she developed it so skillfully that it soon became
almost a conditioned-reflex thing with me; Just the sight of one
of Hedwig’s many erotic outfits, or the feel of it against my
skin, and I was hopelessly lost in lust. So much so that I was
actually sorry whenever I had to take the things off!
Once Hedwig had me wearing feminine apparel on a fairly
regular basis, she started hinting around at ways to even increase
my enjoyment: Bit by bit, she persuaded me to shave my body, take
shots to enlarge my breasts and bottom, make up my face and hair,
and finally get a Pussywig device.
By then, I was so conditioned to respond to whatever new
outfit Hedwig brought me that I would eagerly don just anything
and wear it about in the security of my very own bordello for
hours: Elegant emerald evening gown, Schoolgirl’s Uniform, see-
thru nightie, string bikini Maid Outfit… I could go on and on,
but I’m sure you get the idea.
Anyway, I got so used to wearing these things and looking
just like one of my Girls that somehow I started kind of acting
like them, taking orders from Hedwig, serving things to men in the
parlor, and generally just making myself look seductive and
available, while Hedwig made sure that I wasn’t – available that
Gradually, I got to trust Hedwig so much, and got so used to
serving in my own establishment that things got to the point where
I couldn’t object to anything! Not even when she dressed me up in
an exotic Middle Eastern Slave Girl outfit, with a tight red silk
half-bra that lifted my luscious boobs up for everyone to see, a
narrow, brass belt that locked tightly around my waist, with bells
on it, and a long, diaphanous sheer silk scarf, six inches wide
and three feet long, swaying down from the front of this gaudy
girdle, showing off my shapely smooth legs and playing peek-a-boo
with my pussy while it left my ripe pink bottom completely
exposed. High Heeled slippers kept me up on tiptoe, and about a
ton of jewelry – bracelets, earrings, nose-rings, even nipple
clamps! – flashed and jingled with my every move.
I didn’t even protest when she dressed me like this and put
me in a cage in the middle of the Salon and made me dance for
everyone while she cracked a whip… or even later, when she moved
the cage out to the front window so everyone could get a look at
the Merchandise while I danced around for them!
Unfortunately, that’s when Vanquisha saw me. she seemed not
to recognize me, but the way her eyes lighted up at the sight of
my captivity sent chills up and down my naked spine!
Instantly, she was inside my brothel, pointing at me and
rattling off something in Dutch to Hedwig. Hedwig smiled and shook
her head, but Vanquisha kept insisting, and finally she broke up
laughing and nodded helplessly.
Before I knew it, Vanquisha had put some kind of elbow-cuffs
on me, pulling my arms back painfully (and showing off my breasts
shamefully!) Then she put an ankle-hobble on me, so I could only
take short, mincing steps, and ran a slender, strong, brass chain
down from my belt to the hobble, forcing me to keep my knees bent.
Pins locked in my hair, attached to chains that connected to my
elbow cuffs, so that when Vanquisha was finished, I had to keep my
neck arched back and my nose in the air!
All this time, I kept thinking This has to be some new Kick
that Hedwig’s thought up for me; so I didn’t protest, even though
I couldn’t help shivering in Fear when Vanquisha clamped a Ring in
my nose and began leading me down the Street!
Now Amsterdam is a pretty jaded town, but I have to say the
sight of an obvious dominatrix like Vanquisha leading a captive
Harem Girl – ME! – down the Street drew a lot of attention. Men
and women crowded around to look, as I wiggled my ass and shook my
breasts, hobbling desperately to keep up with Vanquisha while she
pulled imperiously at a leash clipped to my nose-ring. By the time
we got to her place, quite an audience had gathered, and she
charged the interested ones a dollar each to come in and watch me
go down on her!
That was Six weeks ago. At first, I kept expecting Hedwig to
come and pick me up, but she never did. Meanwhile, Vanquisha had
two of her girls put some kind of oil all over my body that turned
my skin dark (The audience paid Five Bucks a Head to watch that!)
and kept me dressed in a grass skirt. How I missed my silks and
satins, with just that scratchy, rustling thing swishing across my
round, dark bottom!
Finally one night I made a break for it; I stole an old
trenchcoat and high heels of Vanquisha’s and snuck back to my own
Bordello. Hedwig met me at the door, pretended not to know me,
and, to my utter horror, had two of my own girls sit on me while
she called Vanquisha to come and pick me up!
And was Vanquisha ever pissed! She put me into one of those
big wire-mesh trash-cans, with my wrists and feet chained to the
bottom, so I couldn’t get out and had to stay crouched down in
there on all fours, then she had her girls drop all their old
panties in on top of me, and hauled it out to the curb!
What a miserable day that was! The weather was warm, but it
was raining hard, and every time a car passed, I got splashed with
mud! The panties clung all over me once they were wet, and
everyone who passed stared and laughed!
Since then, I’ve made it a point to be a Good Little Black
Slave Girl for my Mistress Vanquisha. And it’s paid off! I finally
managed to steal enough change from under the sofa cushions to pay
for the price of this Overseas Letter, and since there’s a Party
this afternoon, I should be able to sneak out to the Post Office
on the corner.
Mr. Crayle, Please come and get me out of this! As soon as I
can get back to my Money in the States I’ll pay you well. Only
EDITOR’S NOTE: Clinton Crayle’s notes indicate that he went to
Amsterdam and found the young man, totally transformed into a
servile Black Hooker. He tried to by her freedom, but Vanquisha’s
price was much higher than he could raise!
Not one to be stopped, Crayle went back to the States, where
he contacted the unfortunate young man’s wealthy older sister. It
took a lot of talking and yet another trip abroad to convince her
of her brother’s plight, but once won over, she agreed to buy him
out of Bondage… On one condition!
When last seen, the once wealthy playboy was working as a
Maid to his sister and her husband! They both get a kick out of
dressing him in the frilliest, skimpiest Maid’s Outfits and
watching his embarrassment as he wants on them at their bedside or
in the bath. The arrangement, apparently, is only temporary, and
it’s undoubtedly better than Prostitution…. but I wonder how
long it’s supposed to last?
Dear Mr. Crayle,
Unlike many others, my purpose in writing to you is not to
get out of some embarrassing situation, but to get your help and
guidance in coping mentally and emotionally with a series of
events that humiliated me profoundly! Here’s what happened:
I am wealthy, my fiancee (now ex-fiancee!) Cynthia is
beautiful, and there was a rival for her affections – a guy named
Rod – whom I narrowly beat out.
When our engagement was announced, Rod offered to be Best Man
and throw the Bachelor Party. All three of us run in a rather
tight and very exclusive social set, so I agreed to this,
On the morning of my Bachelor Party, however, Rod paid me a
visit and asked if I wanted to help him pick out the Stripper.
With visions of my Freedom slipping away in the next few days, I
accompanied him to the most elaborate House of Pleasure in (name
deleted). Where, urged on by Rod’s generosity, lovely girls were
soon swarming all over us!
Someone suggested a luxurious Bubble Bath, and before I was
quite aware of what was happening, I found myself in a marble tub,
sipping Champagne while luscious women plied my body with scented
creams and lotions. Now this was living!
Imagine my surprise, though, when they eased me out of the
warm tub and began toweling me down and I discovered that those
Lotions had creamed away all my body hair and bleached the hair on
my head Platinum Blonde! I started to protest, but the girls
assured me that I looked Real Sexy this way and my bride-to-be was
in for a real treat on our Wedding Night.
Well, the Wedding wouldn’t be for a few days yet, and I told
myself there’d be plenty of time to Undo whatever they did, so I
laughingly allowed them to curl my hair and put makeup on my face.
The result was startling! As I looked in the Mirrored Walls, the
reflection that bounced back at me was of a rather sensuous
looking – if flat-chested – woman!
I mentioned in surprise that if I had something up here
(cupping my hands under my chest) I’d be quite a dish. A tall red-
head said she could fix that, and the next thing I knew, someone
had glued two real looking false breasts to my chest! They were
sealed on with some kind of latex that blended perfectly with my
skin, making them undetectable, and they were filled with Shampoo
or something that made them bounce and jiggle when I moved, just
like the Real Thing!
Next someone suggested that I should pick out what my
Stripper was going to wear that night, and try it on myself, to
make sure it’d look good. I think you’ve figured out by now that I
was quite tipsy by this time, and Rod was nowhere to be seen, and
since I’m a very agreeable Drunk, I went along with the idea.
Before much longer, I was decked out in White Satin: Shiny
white pumps, white fish-net hose held up by ruffled white garters,
a skimpy white satin G-string, shaped like a Heart over my crotch,
and a strapless white satin floor-length Evening Gown to cover it
all. Wow! with elbow-length gloves and a string of fake pearls
around her neck, the platinum blonde who looked back at me from
the mirror was absolute Boy-Bait! The way her breasts swayed and
shook, half-showing above the low neck-line of the shimmering
gown, was positively devastating. With every step, the soft,
slippery fabric trailed across her legs and naked rump, outlining
them perfectly. And this hot-looking dish was really ME!
I was starting to recover my equilibrium by now, if not my
sense, and I moved about before the mirrored walls, posing and
preening, slinking about like a she-cat in heat, and just
generally Vamping and Camping to the delight of the hookers around
me. There were buttons at the side of my dress, with little loops
to fasten onto, and the Redhead showed me how, once these were
joined, the skirt part of my dress became narrower, restricting me
to tiny, mincing steps. There were similar buttons at the waist,
and loops at the tops of the elbow-length gloves, and when someone
smilingly fastened these, it kept my elbows in and my arms at my
sides in a very ladylike manner.
And then someone yelled “RAID!”
Instantly, the room was a blur of streaking flesh and
lingerie as girls rushed every which way around me. Suddenly
realizing the state I was in, and the horrible publicity that
would result if a socialite like myself were to be arrested under
these conditions, I tried to bolt from the room myself, out
towards the fire escape with the rest of the “Ladies”, only to
discover that my steps were terribly hampered by that damn
buttoned-tight skirt! I tried to reach down to undo the buttons,
but those tight, white satin gloves, buttoned to my waist at the
elbows, hindered me. Furiously, I pulled and tugged at the satin
sheath that imprisoned me, trying to get my gloved , arms
That’s when Rod reappeared.
I never knew anyone could be so cruel, so taunting, so
insufferably smug as he could; in the few seconds he the
stood there, gloating over my predicament.
He told me quickly how much the would enjoy the look on
Cynthia’s efface when news of my arrest – in Drag, at a Cat-House
– hit the papers. Laughing, he reflected aloud that she’d probably
need a Real Man to comfort her, and he’d make it a point to be
right there On The Scene.
Then, as footsteps thundered up the steps, he hopped through
the window onto the Fire Escape that led down to a back alley,
after the last of the hookers!
To describe my emotions at that point would take a whole
book: Anger, fear, frustration, fury, worry, jealousy… and above
all the impelling urge to somehow thwart the treacherous bastard
who was trying to steal my girl by getting me into all this!
Emotion gave me strength as footsteps reached the top of the
stairs. With a desperate wrench, I half-crouched and pulled
upwards on my arms, finally managing to tear the gloves loose from
my waist, (Ripping the zipper out in back as I did!) I started to
reach towards the buttons at my skirt, but I knew from the start
that with my fingers gloved this way, I’d never get them undone in
time, and the top of the dress was torn now anyway, so with
another fuming effort, I jerked the hampering skirts down over my
hips and completely off!
Someone was pounding at the door! With my heart in my mouth,
I bolted to the window and all but leaped out onto the fire escape
(hindered to a degree by the high heeled pumps still strapped to
By the time I reached the alley below, there was no sign of
any of the girls. Or of Rod. What there was, was a small van or
panel truck with the back door open, and I ducked inside this
quickly, looking for some kind of cover, uncomfortably aware of
how my stockinged legs flashed in the growing darkness, and of how
my bare breasts and buttocks glistened with fearful perspiration.
I had to hide!
Inside the van was a largish box, maybe three and a half feet
square, made of thin cardboard. I raised the lid, found it empty,
and ducked in, closing it after me.
And not a moment too soon! No sooner had I hidden myself than
I heard someone open the back door and climb in: The Police? No,
whoever it was was wheeling something else inside the truck. And
there was more than one person! I thought I could feel the box
being raised slightly, as if on a Dolly, and almost panicked to
think that they might be going to open it and see me in here like
this, all feminized, wearing just hose, heels, gloves and a G-
But then, to my relief, I heard a sound like… like what?
like something being set on top of my box? or beside it? No…
OVER it! Something was now covering up the box completely!
Well, I was safe from the Police, anyway. As the Van rolled
off into the gathering darkness, with me inside the pitch-black
interior of that box, I congratulated myself on a narrow escape.
Now, wherever they took me, I could probably talk my way into
getting some clothes, something to take off my makeup and cover my
hair, and probably even a ride back to my place. I was practically
I was already planing my revenge on Rod when the truck got to
wherever it was going and someone wheeled the box and I, along
with whatever it was overtop, off the truck and into some kind of
building. I couldn’t hear much and I couldn’t see a thing, but I
got the impression that whatever I was inside was set up
someplace. Someplace inside some kind of building. Somewhere. I
could hear Party Music, but it sounded faint and far away.
Meanwhile, I was starting to feel terribly cramped up inside
that box! What with my stockinged legs bent up and my head down
between them, those false breasts pressing against my thighs, the
tight Cramping my genitals up into my crotch, and my bare bottom
resting on the smooth, hard cardboard, I was pretty damn
Uncomfortable! I’d been motionless for some time now, and as far
as I could tell, I was alone.
So I started to get out of the box.
It wasn’t quite as easy as I’d expected. Whatever was
covering the box was soft, but heavy, like a mattress, and as I
pushed upwards, I could feel it pushing back. And the material of
the box itself was so thin and flimsy, that I felt it begin to
Oh well, I thought, pie crusts and all that… so I pushed
and straightened, feeling the box tear apart around me as I stood
What the Hell!?!? I was surrounded by something soft and
sticky! The music was louder now and there were lights around me!
I pushed at the clinging stuff, wiping it away from my eyes so I
could see and… It was cake! I stared in disbelief as the
music blared out “The Stripper” and everyone around me laughed and
That’s right. I was in the middle of a party. I had just
popped out of a cake, looking totally feminine, wearing only
heels, stockings, garters and gloves, plus that tiny heart shaped
white lace G-string, cake oozing off my lovely face, caught in my
curled hair, and dripping from my bouncing breasts. There were
whistles and shouts all around me, but with the lights in my eyes,
I couldn’t tell for sure where I was or how many people were
cheering me on.
GO ALONG WITH IT, I told myself, PLAY ALONG AND GET OUT WHEN
YOU CAN! So I went into a sexy bump-and-grind, smiling as I kicked
my legs and sucked cake off my fingers, wiggling my tush for
everybody and playing with my oversized nipples. It was
humiliating, but I really thought it was my best bet for getting
out of the situation. If I could just make sure nobody got a look
beneath my G-string, I’d be all right!
And at long last, it was over. Two women dressed as cooks
helped me down off the table, wiped some more cake off my body,
and escorted me back to the kitchen.
But there, to my surprise, when I tried to explain to them
that I needed clothes, they acted like they already knew all about
my predicament! With complete nonchalance, they stripped off my
clothes, including the G-string, and put me in the sink, where
they proceeded to wash me off thoroughly with a sprayer attachment
and dry me with dish towels! They didn’t show even a trace of
surprise at seeing my male privates!
In a daze, I let them dress me in black silk stockings, dark
patent leather heels, a skimpy white apron, matching cap and white
ruffle collar and cuffs. They explained to me that I would have to
serve refreshments to the guests before I could leave, and in my
state of total confusion, I didn’t object as they handed me a tray
of snacks and sent me back out into the Party Room.
Where I came face to face with everyone I knew in the World!
You’ve probably guessed by now, Mr. Crayle, that al this was
Rod’s scheme to disgrace me in front of Cynthia and everyone else
in our social set, and I have to say it worked perfectly. The
visit to the Brothel, the “raid”, the truck so conveniently parked
outside, everything had been engineered to bring me to this
moment: Standing aproned, high-heeled, feminized and topless
before my fiancee and all our friends, acting like a demure little
serving girl now that I’d done my shameful dance!
And even now, when I tried to protest and explain, they
didn’t care to listen. One of the ladies who’d washed me off
threatened to spank me in front of everyone if I didn’t behave, so
I had to smilingly serve snacks, curtsy, and prance around
daintily in front of everyone.
You can imagine how totally mortified I felt during all this,
and my dreadful frustration as I tried to hide my true feelings
and simper prettily all around, especially whenever someone would
pinch my bare bottom or set their fingers exploring under my apron
skirt! But can even you realize how I must have felt when Cynthia
told me that our wedding was off, but I’d be welcome to
participate in her wedding to Rod: If I wanted to be a Bridesmaid,
And that’s what I’m writing you about, Mr. Crayle. Once I got
back to my own house and clothes and got those dreadful breasts
off my chest, the enormity of all I’d lost really sank in: My
friends, my fiancee, my self-respect and reputation… all gone in
At first, I thought I’d simply murder Rod, and perhaps
Cynthia as well, but lately I’ve begun to think that there must be
better, more satisfying forms of revenge. You can name your price
Mr. Crayle, but I want some plan for doing to Rod what he did to
me – and even more!
If you don’t do this sort of thing, but know of someone I can
contact who will, then just refer me to them, and I’ll still pay
your fee. I know Rod will be watching out for something, but there
must be some way or someone to pay him back!
Enclosed find retainer.
EDITOR’S NOTE: I have Clinton Crayle’s follow-up report on this,
somewhere in my files, tentatively titled “Failed Revenge”. Can’t
find it at present, but I’ll keep looking.
Dear Mr. Crayle,
Despite what you’ve heard about Women’s Lib and how
Progressive the Media is, let me tell you, it’s hard for a Female
to find a really meaningful job on a Big-City Newspaper, even
today! I’ve risen to 2nd Assistant Editor for the
ACCENT/ENTERTAINMENT Section, but so far, the really important
assignments have eluded me.
Now, though, I think I’ve got an inside lead on a really
important in the Hard News Department. All I need is some help
from you to confirm this thing!
Just by way of background, there was recently a big Political
Shakeup in our City, with the Police Chief being arrested for
accepting bribes from Drug Dealers and I-don’t-know-what-all. The
thing is, I have some dope on how his downfall really came about –
maybe – which is what I need your help to confirm.
See I was covering one of our local Drag Clubs when I ran
into a guy whom I recognized as a Cop, Dancing in the show! This
cop (I’ll call him Jim) is/was a real up and coming hot-shot in
the Detective Bureau, despite the fact that he was awfully young
and looked even younger, and only a few of us in the Media knew
him, because he worked undercover a lot and avoided publicity.
Well, once I pegged him, and threatened to blow his cover if
he didn’t spill the beans to me, he let me in on what a sexy,
virile young Cop was doing with his body shaved, hair curled and
face made up, dancing around in High Heels and Panties; Seems he
was working on discovering some Mr. Big in the Drug World, and the
Chief had gotten word that this Drag Club was a major Conduit or
something. So Jim had been assigned to get a job working
undercover here, and the only way he could do it was by posing as
Naturally, I promised to keep all this secret, in exchange
for being the First to Know when things broke, but somehow the
story leaked out anyway… or at least reports to the effect that
some Police Officer (or Officers) were spending City time and
Money hanging out in Gay Bars!
Once the anti-gay factions in the city heard these rumors and
demanded to know what was going on, the only thing the Chief could
do was tell them Nothing of that kind was going on, and he
reportedly ordered my feminized hero off the case.
But by that time, Jim (Stage Name Ginger) had hooked up with
a high-priced and highly-specialized Call Girl named Domina, and
blackmailed her into helping him get a very promising Lead on the
case. Seems Domina’s little sister is a Rookie Meter Maid or
something, and her Big Sis is a Doctor, and to keep Jim from
telling the World what their Sister did, she went along in
providing him information.
Anyway, I suspect that Jim/Ginger worked out a verbal
arrangement with the Chief whereby he would pretend to Quit the
Force, but actually wrap up the Case in a few days. That was the
A few days later, though, I was visiting the Club, and as I
watched Ginger dance, some woman (or man dressed as a woman)
spilled a drink on the stage, the Cop-in-Drag slipped in those
heels and took an ugly fall!
It turned out he/she had twisted an ankle and had to be
hospitalized. (For a twisted ankle? That’s one of the details that
got me suspicious!) Without employment or insurance, the hospital
bills ate up his savings, he lost his apartment and had to move in
The funny thing is that when Jim got out of the Hospital, his
appearance was changed! He now had large breasts and bottom, dyed,
styled hair, and absolutely no hair at all below his scalp (As far
as I could see, anyway; I just got a quick glimpse of him/her
ducking out a back door. At the time, I didn’t even recognize…
uh, whatever s/he was!)
I figure maybe he was talked into having this done at the
Hospital in order to keep some Bad Guys from recognizing &
eliminating him while he was disabled with that twisted ankle. One
thing that does stick in my mind, though: Domina’s older sister is
a Doctor… and she’s on the Staff at that Hospital!
Well, like I say, Jim (now really looking more like Ginger!)
moved in with Domina, and just what he did to earn his keep with
her, I don’t know for sure. Call Girls don’t associate much with
Reporters, even female reporters, like me, so I didn’t get a
chance to really see Ginger up close (I think!) until about a
That was the night I was checking out the Red Light District,
very late, following up a tip that something big was going to go
down somewhere around a well-known Gay Bar.
That’s when I saw Domina strutting down the street, wearing
some kind of soft-latex black dress that looked like it’d been
painted on her! I don’t know how high the leather boots she wore
went, but they disappeared right up the sides of her slit skirt,
and the heels on them were six inches high at least! The woman
must have been a real athlete to walk in a get-up like that!
But what really caught my eye was her “escort”. There was a
well built, attractive looking chick, dressed in heels, a
minuscule string bikini and a collar, being led down the street by
Domina, on a leash! She looked really embarrassed at being paraded
around like this, and I remember wondering if it was her massive
curves, skimpy attire, or the collar and leash that distressed her
In front of the Gay Bar, Domina handcuffed the girl’s wrists
behind her back, tied her leash to the handle of a parked car,
and, with a few deft tugs, untied the string bikini and snatched
it right off!
That’s when I saw the flash of male goodies there at the
crotch of this incredibly feminine-looking creature. She was
really a he! And based on what I knew about Jim and Domina, I had
a pretty fair notion of who he/she was… Not a Publishable
Certainty, mind you, but definitely a Strong Suspicion!
Meanwhile, relieved of “his” bikini, and handcuffed to boot,
the poor nude Hero-ine quickly squatted down to hide “his”
embarrassing male genitals between “her” smooth thighs, pleading
in a soft femmish voice for “her” clothes back. Domina just smiled
down at “her”, wadded the tiny swimsuit up in a ball, and stuffed
it in “her” mouth, using one of the halter-straps to hold it in
All at once my attention was diverted by a flurry of activity
behind this Odd Couple: shouts, shots, people running every which
way, and before I knew it, there was our Chief of Police, being
led off in handcuffs by DEA agents!
For the next several minutes, I was taking names and
statements, listening in as the Feds thanked a young Meter Maid
(Domina’s Little Sister, it turned out!) for breaking this case,
revealing that the Chief was behind the drug running the whole
time, and had been sending his best men around on Wild Goose
Chases to cover up.
Speaking of Wild Goose, I suddenly remembered Domina and the
Anonymous Tip that had led me here. I looked down at the pathetic
little she-male squatting down there on the pavement, bleating up
at me. Lord, what tits that babe had!
One of the DEA boys saw them too, as Domina was detaching the
leash from the car door handle. I could tell he thought the thing
wearing heels and collar was female, until “she” shifted on the
sidewalk, revealing a flash of embarrassed erection.
“Can you believe some guy would actually pay a woman to do
that to him?” The Fed asked me, “But there she is, leading the
little queer off… Jeeze! Look at the way she cracked his ass
with that riding crop! Now she’s making him duck-walk!”
Well, I’ve been trying ever since to get close enough to
Domina to determine whether or not the shemale she was parading
around that night was really the former male cop. And I haven’t
had a bit of luck! Then I thought of you, and your reputation for
handling bizarre cases. Of course, there’s no way I could take you
on at your usual fee, but
I’m sure we could work something out. Please call me at (DELETED!)
EDITOR’S NOTE: Crayle’s records indicate that he and the female
reporter were unable to agree on a fee, and he never got actively
involved in the case.
*MORE LETTERS TO FOLLOW*
6 thoughts on “Rare Letters”
Thank you for more great CC stories! So many fantastic ideas that could be fleshed out. I especially liked the young american owner of a Dutch bordello.
I’m pleased you liked my idea of a wealthy businessman being draw into The Hotel. I have to confess that the idea has really grown on me and I often find myself daydreaming of scenes and plot twists that could occur.
When will you be publishing your next story on Lulu?
… and I am pleased to say I have been sent even more C.C. and Timothy Riesling Tales to load onto the web site.
As for publishing more books, I am afraid that I am way to busy for a while. However I am hoping that very soon I can offer up a few more.
Thank you again for your encouraging remarks.
Deborah, you tease! Boasting about new stories from C.C. and TRB but not posting any. What a way to drive someone wild!
Still, I’m sure you must be busy.
blushes from head to foot.
they are in my ‘to do tray’ and will get to them …honest!
Would love to try Bill and Irene’s costume (both ways round)
Indeed Blackfive. I am sure there are many outfits from Crayle’s tales that we would all love to try.