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It was to be a long session. Mistress called me from
work and told me to be ready to be well used. It had
been a difficult day and she would be taking out her
frustrations on me! Once the chores were finished I
went up to her bedroom to prepare. First I loaded the
CD player and set it to repeat to provide background
music for my wait. Then I opened the Toy Box and began
to prepare.

First I put on the black Basque with its garters. It
covers from below the breasts to my waist and is quite
tight when it is fastened. Next I drew on the long
black seamed stockings. Carefully I drew them upward
until I could fasten them to the Basque with the
garters. Checking the seams to be sure they were
straight I then carefully disarrayed the right stocking
so as to annoy the Mistress. Not that she would need an
excuse to use me well, but there is no use in taking
chances.

Next I bend over and put on the high heels. The high
arch (5 inches) combined with the wide ankle straps
make for a delicious bit of height and bondage.
Especially after the straps are locked, securely
fastening my feet in their bonds.

I pick up the Cock harness and fasten the waist strap
over the Basque and bring the cock ring down to my
stiffening cock. I pull the balls through first and
then squeeze the flaccid penis through. It stays
shrivelled for only a moment and then begins to expand
and swell. Now I get out the creme and grease the butt
plug. Then taking a generous quantity of creme on my
fingertips I reach past the dangling harness and begin
to apply the lubricant to my anus.

Slowly I slide my finger in my rigid ring muscle and
slip it in and out stretching my rim to accommodate the
butt plug. Finally I pick up the butt plug and press
its’ head to my anus. Gently I begin to force it deep
with in, squeezing to tire the muscles of my ‘back
door’ so that suddenly it is forcing the widest part of
itself past my nether hole and I gasp as it makes its’
way home.

It is the work of a moment to grasp the crotch strap
and pull it tight forcing the butt plug even deeper
with in me. My cheeks are pushed apart by the width of
the strap and I wriggle my ass to revel in its
fullness. I fasten the thigh cuffs to complete the
imprisonment of my buttocks and take a moment to strut
about in my captivity. I like the sight of myself as I
teeter on the high heels and wriggle my hips and ass. I
feel like the little slut that my Mistress likes me to
be and my cock hardens in anticipation.

My collar and leash come next, and when they are
securely fastened I get out the wrist and ankle cuffs
with eight locks and four lengths of chain. It takes
only a moment to fasten them about my limbs with the
chain and place the locks in the eyebolts in the
doorframe of the closet. I make a last pass through the
apartment making sure all is secure and ready for the
arrival of the Mistress in about two or three hours.
Then I turn on the CD player and go to the closet. On
the way I pick up the blindfold and ball gag harness.

I stand in the doorframe and bending left then right
fasten my ankles to the lower eyebolts. My legs are
held wide and stretched and I revel in the helplessness
I am about to experience. Quickly I put on the
blindfold and make it fast. Next I open my mouth and
render myself mute with the ball gag deep with in. It
is the work of an instant to pull the straps tight
silencing me and holding me in anticipation of my
service.

Straining I reach up and find the last two eyebolts
overhead. Working one handed I slip the end of the
chain at my wrists through the locks above and then
with two final clicks I am bound spread-eagle in the
closet doorway of my Mistresses bedroom. Now I can only
wait for her to come home and release me to my
servitude. I shudder with anticipation.

Time passes. In the darkness behind the blindfold I can
only wait and savour my helplessness. From the arch of
my feet in their high heels, to the butt plug deep with
in I am only an instrument of my Mistresses pleasure.
My feet begin to ache and my legs tremble from standing
so long. I have completely lost track of time. I no
longer can remember how many times the CDs have cycled
through and it seems longer than I can imagine.

Finally in my daze I stiffen and tense. Is that the
sound of footsteps approaching the apartment door? I
almost scream in relief when I hear the sound of a key
in the lock and I hear the click clack of the
Mistresses heels in the foyer. The door closes and I
follow the sounds as Mistress moves about the
apartment. Finally she comes into the bedroom and I
hear the click of the light switch. Silence reigns as I
wait in darkness. I hear the rustle of her clothes as
she moves away and I am left only with the scent of her
perfume.

The dresser drawer opens and I hear clothe swish as it
is removed and dropped to the floor. I listen as
Mistress begins to dress herself and I wonder what it
is she will be wearing or if I will even be allowed to
see. Finally she walks over and stands behind me and I
know with out seeing that I am being inspected.

“Well my pretty one,” she says, “Are you ready to be
well used?” Frantically I nod yes and moan into my gag.

Laughing the Mistress says, “Don�t go away then, I’ll
be right back,” and I hear the sound of her high heels
go into the kitchen and mix a drink.

More time passes. Now I am becoming stiff from my
restrained position and my cock aches from
anticipation. At last I hear her footsteps return and
my Mistress begins to run her hands over my bound, silk
clad body. Grasping my swollen cock she coos, “My we
need to do something about this, don’t we?”

I moan into the gag and Mistress squeezes my shaft
sharply in warning, “I’ve warned you before about
speaking haven’t I slave?”

I nod yes and she continues, “It seems I’ll have to
remind you again. Not only are you speaking with out
permission but also you have a crooked seam in your
stockings. What ever shall we do about this?”

With that she lets go of my prick and wanders off to
the Toy Box. Her return is signalled by a caress along
my inner thigh. It is not her hand that touches feather
light up to my buttocks and then down to my heel
tracing the line of the seam in the black hose. It then
continues back up the other heel to my buttocks again.
Flinching I try to pull away from this odd caress. What
is it that the Mistress is touching me with? As if she
was reading my mind she tells me.

“In case you were wondering what this is,” she says
once more continuing the slow caress of my thighs and
buttocks, “it is a little friend of mine called a cane,
that I use to remind forgetful slaves of their place.”

Just as she finishes speaking she lifts it away from my
flesh and strikes a sharp stinging blow to each cheek.
I yelp into the gag and try to pull away from the pain
but I can only sway back and forth in my bonds. Even
this scant amount of movement is intolerable to the
Mistress because she says, “You have a bit too much
freedom to be proper slave. We need to make some
rearrangements.”

My hands are unshackled from above and brought together
behind my back. Next a broad leather strap is fastened
above my elbows and pulled taut until they nearly
touch. A rope is fastened between my wrists and passed
through the eyebolt directly overhead. As the Mistress
pulls on this, my wrists are pulled upward and I am
forced to bend at the waist. Soon my leash is touching
the floor and Mistress pauses to shorten it and lock it
to the eyebolt placed there for this purpose. Then my
arms are pulled up once more until I am nearly
immobile.

My head is below the level of my waist, pinioned by the
leash, while my wrists and arms are pulled nearly
straight up, and my feet are held in place to the
floor. My buttocks jut outward and now invite the
attention of the cane that my Mistress begins to once
more brandish behind me.

“I think about 25 to each cheek should be a sufficient
reminder not to speak and to keep your seams straight.
Don’t you slave?” she purrs.

Before I can reply she strikes first one cheek and then
the other. Sometimes it is three in a row to each side.
Sometimes they fall left, right and a pause. Other
times it is a single blow to a side and I am left to
wait for the next one for what seems forever. Between
times the Mistress uses the cane to caress my burning
buns or rubs them with her hand.

“You are getting a fine shade of red my Pretty one,”
she says, “Maybe we need to do this more often.”

Blow after blow falls but slowly through the pain of
the sharp stinging blows I begin to feel a heat build
in my cock. As the blows land the pain starts to take
me closer and closer to orgasm. Soon I am almost
thrusting my hips like a slut in heat trying for just a
bit more sensation. I lost count of the blows at about
nine or ten and it is almost with a sigh of regret that
I greet the announcement that she is through. Softly
she caresses my flaming ass and reaches between my legs
to feel my prick.

“One would have thought you were getting turned on
there at the end,” she says as she touches the head of
my shaft.

“My Pretty one,” she purrs, “You almost came didn’t
you?”

When I make no reply she cuts me across a cheek with
the cane again. “Didn’t you?” she asks.

Quickly I nod yes behind the blindfold and the gag.

Laughing Mistress promises, “Well if you are very, very
good to your Mistress I may let you come later. Much
later.”

PART 2

Now Mistress leaves me for a short while. My ass throbs
with the heat of my caning. In the dark I feel the
tight restrictiveness of my bonds. Bent over at the
waist, with my arms bound tightly elbow to wrist, every
inch of me feels my enslavement.

I hear the sharp clicking of my Mistresses footsteps as
she once more approaches me. I feel a sharp tug at my
wrists, as the rope to the top of the doorframe is
pulled even tighter and then sag in relief, as it is
unfastened.

A tug on my leash brings me to my knees with my ankles
still attached to the base of the doorframe. Now my
ankles are released, and the chains from each side are
brought together and locked to a third length of chain
that is run up to my wrists. Next the gag is removed
from my mouth and Mistress stands in front of me.

I know what it is she expects and I quickly bend and
seek her feet in the dark to give her the homage she
deserves. After I kiss her feet my leash is unlocked
from the floor, and she tugs on it to signal me to
return to my kneeling position.

“I will be in the living room Slave. You will crawl to
me on your knees to serve me further,” she commands. I
pause to listen to her footsteps recede in the
direction of the living room and then begin my blind
fettered journey to service her.

Hobbled as I am I lose all track of time as I crawl to
the living room. When I finally enter I pause to try
and determine just where the Mistress is. At last I
hear the clink of ice cubes as she sets down her drink
and I hasten to crawl to her side. Carefully I kneel
beside her as she lies at ease in her chair, and I wait
in anticipation for her to take heed of my presence. I
hear her turn the page of a magazine she is reading and
then she lies back in the recliner.

“My boots are in need of a cleaning Slave. Put your
Slave tongue to work on them.”

Eagerly I crawl to her feet and turn to face her.
Slowly I search her boots out with my blindfolded face
and begin to lick and suck at her boots. The leather is
slick and warm beneath my tongue as I give her my
devotion. I savour the taste of the leather and the
smell of her. I work my way up their length to the top,
which is just above her ankles. I am almost
disappointed that they are not her thigh high boots,
which would offer me the chance to draw near to her
most secret depths.

Finished for the moment, I pause as she crosses her
ankles and begin to clean her boots again. I spend long
moments taking the length of the spike heels into my
mouth and lick and suck on them as I wish she would on
my bound cock.

After a time she notices that I have finished with her
boots. Now she commands me to remove them and begin on
her feet. Using only my teeth because of my bound hands
I untie her boots and slowly work the laces loose to
free her feet.

At last they are free and I revel in the twin aroma of
her boots and her silken clad flesh. Once more I lick
and suck at the feet of my Mistress. Slowly I suck on
each smooth toe through the confines of the stockings,
and then I languidly bathe the lengths of her soles
with my tongue.

Tiring of my ministrations to her feet, Mistress orders
me to sit back. I hear the recliner fold back and I am
ordered to crawl forward. Can it mean that she is ready
to use me for her pleasure? Casually she leans forward
and picks up the end of my leash. With a gentle pull I
am drawn deeply between her legs. I feel the heat of
her thighs along my face, and I smell the sweet dusky
scent of her innermost recesses.

“Use your tongue Slave. Eat me,” She commands.

I need no further urging, and in the darkness of my
blindfold I gently bring my lips to hers. Slowly I ease
my tongue into the dark wet folds of her slit and I
taste of her nectar. I work my tongue deeper as I slide
it between her labia and begin to lick at her tender
flesh. Savouring the scent and taste of her I begin to
lap up her juices, and run my tongue from the base of
her slit to her clit. Her lips begin to expand and
swell from her arousal, and I am rewarded by her warm
throaty purr of pleasure.

“Yes, deeper Slave,” she moans, and I obediently thrust
my tongue into her depths. After a time I work my way
up to her clit and when my tongue caresses it Mistress
grabs my head with her hands and pulls me in tight to
her.

Her thighs imprison me as I suck hard on her clitoris
and begin to caress the little man in the boat with my
tongue. Around and around and around I move my tongue
varying firm slow strokes with quick darting flicks.
Soon I feel her thighs tremor in rhythm to my tongue
and I know it is only a matter of moments before she is
on the brink.

Slowly I ease back for a moment, and she quivers on the
very edge of sensation when I begin to deliberately
stroke her clit and I am nearly pushed away as she
begins to buck her hips and cry out in pleasure. While
she slowly comes down from the heights I gently kiss
and caress her thighs between the tops of her stockings
and her lips with mine.

Reaching forward she removes my blindfold and rewards
me with a glimpse of her. Her full breasts are
displayed on the shelf of her red satin bustier. Her
pale thigh flesh contrasts nicely with the curly hair
of her pubes and her red stockings. I lean back as she
releases me from between her thighs and I see the full
length of her legs in her stockings.

Gazing up at her in worship I can only hope that she
will use me further. I need not worry. As soon as she
has caught her breath she gives me new commands.

“You have pleased me Slave. Now go to the bedroom and
bring me back my latex briefs with the dildo built in.”

“Yes, Mistress,” I reply. Carefully I rock back on my
heels and slowly stand up. It is difficult to catch my
balance because of my bound wrists and the fetters on
my ankles but once upright I quickly proceed back to
the bedroom. I revel in the twist and sway of my hips
as I journey back to the toy box in the closet.
Kneeling before the toy box I turn and can barely bring
my fingers to the handle of the lowest drawer.
Carefully I open it and turn about.

There in the drawer are the Mistress’s latex toys. I
lean forward and with my mouth I pick up her dildo
briefs from the drawer. The shaft of the dildo slides
between my lips and the body of the briefs hang
obscenely in front of my face. Slowly I suck on the
shaft until the base of the dildo is at my lips and I
stand and return to the Mistress in the living room.

While I have been in the bedroom the Mistress has been
busy. From the closet she has brought out the pillory,
which tells me that she intends to use me quite well
this evening. Now I kneel before the Mistress as she
stands by the base of the Pillory and wait as she takes
the dildo pants from my lips.

I tremble in anticipation as she slides them up her
long legs and carefully adjusts the prong and jutting
shaft on the inside to her satisfaction. The slender
black phallus thrusts out obscenely from her crotch and
I am curiously aroused by this sight.

Now she struts back to her chair and carefully pulls
her red, high heeled ankle boots on and laces them up.
Next she stalks back to stand before me. Snapping her
fingers she points to the floor and I strain to bend
over and kiss her feet. Carefully I lick and caress her
boots until she tires of my submissive display when she
snaps her fingers again and points to her out thrust
penis. I lick my lips in anticipation and then slowly I
begin to lick and suck on her shaft.

As I kiss and caress on it with only my lips it bobs
and weaves about. I know that this causes the interior
shaft and prong to rub and caress her clit and vagina
at the same time. With a soft purring moan from her
lips I know that I have succeeded in arousing my
Mistress also.

Now I slide my lips to the end of the shaft, and move
so that I am facing the Mistress. Slowly, ever so
slowly I take the full length of her latex shaft into
my mouth. It is so long that it soon is at the back of
my throat and I begin to choke on it. Easing back a bit
I suck on its length in my mouth and let myself become
accustomed to its fullness. Again and again I slide it
to the back of my mouth until suddenly Mistress shoves
her hips and my lips are forced to the base of its
length and it forces its way down my throat. For a
moment I panic and then I relax and let it slide in and
out of my lips. Slowly she begins to fuck my face
thrusting it to the hilt in my mouth.

I suck on it in time to her thrusts and soon she begins
to tremble as the additional stimulation begins to make
it felt on her clit. With a guttural growl she comes
and she spasms from the force of her orgasm.

“Well,” she announces as she catches her breath and
removes her latex phallus from my lips, “If your mouth
felt that good your ass will be wonderful indeed.”

Picking up my leash she leads me to the waiting
pillory. My neck is placed in the centre hole of the
bottom half. It takes her but a moment to slide the top
half down and to lock it securely holding me bent over
at the waist with my chest parallel to the floor. Next
the chain between my ankles running to my wrists is
unlocked and my arms are pulled upward toward my head
by means of it. A quiet click announces that it is
fastened to the top of the pillory.

Now my legs are spread apart and secured in the
horizontal stocks provided at the foot of the pillory.
Not only do they hold my feet secure and immobile but
also they provide a short platform for the Mistress to
stand on. So secured I am subjected to rubs and
caresses on my posterior which is still tender from my
earlier caning. Stroking my ass Mistress comes to a
decision. “You need to be a bit redder before I screw
you in the ass. Wait here while I get the paddle and a
gag.”

Unable to move because of the extreme bondage I have
been placed in I await the return of my Mistress. My
buttocks extend outward helpless to resist any use to
which the Mistress may wish to put them. I hear the
click-clack of the Mistress’s high heels as she returns
from the bedroom and I tense in fear and anticipation.

Slowly now she walks about me viewing her restrained
property. Standing in front of me she holds up the ball
gag. Commands are unnecessary as I open my mouth to
receive it.

“That’s right Slave,” she says, “We don’t want to
bother the neighbours with unneeded noise.”

Pulling the straps tight, she rubs my cheek with the
paddle, and laughs as I flinch from its caress.

“Not to worry, Slave. It’s your other cheeks that will
feel this.”

Now she stalks behind me, leaving me to await her pain
or pleasure. Softly she caresses my rear with the
smooth surface of the paddle. Her hand slides between
my legs to pet my hard aching shaft. I shake at her
touch and she laughs to have had such an effect on me.
Suddenly without warning she strikes! Blows begin to
land on first one cheek and then the other. I feel the
heat of them start to build and I writhe and squirm
from the blows.

Held captive at neck and ankles, I struggle in vain to
escape. To no avail I cry out for mercy into the
muffling restraint of the gag. For a moment I don’t
think the Mistress has heard me but then she stops.
Gently she caresses my burning cheeks and murmurs, “No,
not quite red enough yet.”

With that blows fall all over my exposed buns. From the
tops of the stockings to the bottom edge of the bustier
she rains sharp stinging blow after blow. This is
alternated with cool strokes from her hands until even
her caresses are painful. Tears are running down my
cheeks when she finally announces that my buttocks are
red enough. Heat pours from them and I wince at her
slightest touch. Now she reaches between my cheeks and
loosens the strap of the cock harness running between
them. Carefully she grasps the base of the butt plug
and works it loose. It pulls free and I am left with a
feeling of emptiness in my ass that I long to beg for
her to fill. Nor am I left too long as she stands
behind me on the platform of the pillory.

“I hope you greased the plug well,” she says as she
places the head of her dildo on the rim of my anus.

Softly she teases me running it up and down the crack
of my ass and then just the head of it in. My nether
rim is still stretched from the hours with the butt
plug in it and it slides past it easily as I relax.
Swiftly it glides in to the base and I scream into the
gag as she rams into my still flaming cheeks.

Patting my ass causes me to jounce around as she laughs
and comments that the gag was a very good idea. Now she
slowly alternates five long slow penetrations of my ass
with fifteen quick, sharp thrusts. My cock bobs and
weaves as I am butt-fucked and I can feel the approach
of an orgasm. Finally she begins a long series of long,
slow, deep thrusts as she lies over on my back and
grasps my cock with both hands. Now in counter time to
her thrusts she begins to masturbate me, and I screw
her hands in rhythm to her thrusts.

“You want to come so badly now, don’t you Slave?” she
coos.

Vigorously I nod my head and try to cry out.

“Well, I think that you have finally earned it,” she
says as she stands upright grasping my hips and
speeding up her thrusts.

“Now Slave, cum. Cum for your Mistress,” she cries as
she starts to spank my enflamed flesh.

On top of all the other stimulation I have been
receiving this proves to be too much and with a loud
cry into my gag I begin to shudder in long waves of
orgasm. My cock pulses and spurts and my cum splatters
onto the base of the pillory. Wave after pulsing wave
of orgasm rolls over me and I am left weak and
shuddering as Mistress pulls out of my sore and tender
ass.

As I helplessly stand and try to recover my breath I
can only tremble as Mistress announces, “Now I’ll have
to decide what to do with you for the rest of the
evening.”

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My first and only time with a transvestite

This is a true story that I would like to share, and happened during a holiday trip to the beautiful country of Philippines, 4 years ago. A group of four friends and myself, decided to spent a week at a resort near Cebu city. The guys were talking about the crazy nightlife,and how they wanted to meet local girls and get hammered. I mostly wanted a peaceful few days next to a pool bar. I had the luck to hadhad extensive holidays in my time, as I was mostly working at resorts around the med for...

3 years ago
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A Transvestite Autobiography

A Transvestite Autobiography I've had a number of questions and responses and thought someone should write why they do this cross dressing stuff. So if I may, I'd like to tell readers of my sad tale. I come from a large Catholic family, five brothers and two sisters, and I'm right in the middle. At an early age, one of my older brothers told me that my parents didn't want me; they were trying for a girl. I don't know if he told that to my younger brother, but he's so messed up...

4 years ago
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Transvestite Caught part 1

TRANSVESTITE CAUGHT by R.J.D. & "c.c." Like a lot of men, I've always been fascinated by Lesbians. I would often go down to the Times Square Bookstores and go through rack after rack of those magazines that feature models in simulated lesbian poses, and I'd get a charge out of it every time, often returning to my plush apartment with stacks of magazines, paperback books and videos to keep me entertained. I don't know just what it is that has always turned me on about the idea of...

4 years ago
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The Private Transvestite Detective or the Undercover Dick

Chapter 1 It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated my red-painted toenails through the gauzy nylon of my fully-fashioned stockings. They were overdue for a touch-up, and so was I. The fading light feebly outlined the sign painted on the glass panel of my office door. It read: ycnegA evitceteD etavirP- snolyN elehciM. A shadow darkened the glass panel and I leaned...

3 years ago
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First time transvestite dogging

I have been cruising since I was a teenager. As I got into my 20's I became more adventurous and began wearing women's underwear underneath my male clothes.Some men I met loved it, others didn't.Online one day I chatted to a transvestite who agreed to meet me fully dressed that evening in a toilet in a country park. I went at the agreed time but to my shame I really did not think it was seriously going to happen. I just could not picture someone taking such a risk with a stranger.When I pulled...

3 years ago
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A true story me and a transvestite man part 1

* This is transferred across from my old profile (LookingForSomething) *This isn't a 'story' at all, because it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.OK, about 15 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale...

3 years ago
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A true story me and a transvestite man part 1

This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born...

2 years ago
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The Reluctant Transvestite

The Reluctant Transvestite By Pippa HighHeels [email protected] Synopsis: James Miller has a secret vice. He loves it and hates it at the same time; he revels in his perversity and is ashamed of it all and it's implications. He finally gets an exciting lifeline, then the professional help of a trained psychologist. But all is very far from what it seems... [James Hillman, a psychologist, wrote: "Loving oneself is no easy matter, because it means loving all of oneself,...

3 years ago
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Transvixen Transvestite Rock Band Chapter Two

Transvixen By Michele Nylons Chapter Two: Transvixen begins "No fucking way!" Panti and Cherri shrieked in unison. They were sitting at the kitchen table opposite Wendy. "Look! Here's the fucking bottom line." Wendy pointed to a bunch of figures on a spreadsheet. "Vixen is losing money. If I can't get you decent venues and crowds you might as well break up the band right now," Wendy explained. "Before you say definitely no, listen to my plan," she went on. "The band...

4 years ago
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Why Some Men Prefer Transvestites

Why Some Men Prefer Transvestites by Michele Nylons Copyright© 2009 by Michele Nylons Introduction To set the scene, I am a middle-aged, married, businessman who also happens to be a part time transvestite. That is I like to dress like a woman and experience sex with men, other transvestites, crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to...

1 year ago
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How I Became a Transvestite

How I became a Transvestite This story is mostly fiction, I will leave you to guess which parts are autobiographical. I'm now in my seventies, happily married to Denise. These events happened a long time ago now, but document the start of our less than usual relationship. - - - - - - - - - - - - - - - - - o 0 o - - - - - - - - - - - - - - - - I admired Denise's pert bum as she got out of bed and headed to the bathroom for a shower, before we went out for the evening. As I lay...

2 years ago
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How i became an transvestite whore

A year ago I was a straight guy with an ordinary sex life. This year I am a crossdressing hooker working the streets of West Hollywood. If there is a lesson to my story, it is to be careful what you experiment with, because you might end up being transformed into a tranvestite prostitute like me. It all started with a brief experimentation in cross dressing. One Friday night I dressed up in slutty women’s clothing. It took a few hours to get transformed, but I did look hot. Very hot. I started...

1 year ago
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Why Some Men Prefer Transvestites

Introduction To set the scene, I am a middle-aged, married, businessman who also happens to be a part time transvestite. That is I like to dress like a woman and experience sex with men, other transvestites, crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to consider myself a 'crossdresser' until a few years ago. To explain; that means I used to dress in female...

2 years ago
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First time with a transvestite

I have always enjoyed cross dressing, and in the few years I have been divorced, I have been lucky enough to dress whenever I pleased, but at 6, 2" and 15 1/2 stone, I'm never going to pass as a girl. If you see my favourite videos on my profile, you'll notice that quite a few are transvestites fucking guys, and this is something I have always wanted to do, but the opportunity has never arisen....until last weekI was in Amsterdam on a business trip, and was supposed to fly in and back in a day....

2 years ago
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Transvixen Transvestite Rick Band Chapter Six

Transvixen By Michele Nylons Chapter Six: Bliss Michelle Murphy studied Tony Carlotta carefully as she sipped her Chateau Lafleur 1982. Only the best for Tony. He was a big man for sure but he carried his weight well distributed on his large frame. In his dark Italian-cut, hand-crafted suit he looked distinguished and projected an aura of wealth and power. To put it crudely; he looked like someone you didn't fuck with both physically and professionally. His head was large...

2 years ago
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A Transvestite8217s Tale

As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front of me slowly opened to admit the guy from the stall next to mine. “Oh yessss!” the guy hissed quietly, slowly wanking his rigid cock and bolting the door behind him as he took in the erotic sight of me lying back in front of him, me now totally exposing my sexy undies to his gaze, “That’s nice very...

2 years ago
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A transvestite meets up with a guy and his dog

As I lazily drove along in the evening’s dim light and looked down at the hem of my black PVC mini-skirt, I saw that as I passed under the orange glow of the street-lights, the knob-end of my semi-hard cock, my black suspenders and my stocking-tops were plainly visible between my nylon-clad thighs! I seldom if ever wear panties or briefs preferring to let my cock and balls dangle naked and unhindered underneath a short skirt or dress. Maybe I should explain right here and now that...

4 years ago
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Confessions of a transvestite hooker or whore

Confessions of a transvestite hooker or whore – you cannot be serious I hear you cry – well I am as I reflect on my life in dresses to date and some of my experiences which I am about to write about here as a memoirs of a life in dresses.So why use the term ‘hooker’ or ‘whore’ – well what I am about to relate from my current stage of life the memories are that upon reflection the meets I am about to relate felt more like me being a provider of sexual services and pleasure to people desperate...

2 years ago
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Halloween Transvestite Stripper

It was Halloween Night 2018 and of course Kristy was going out to party! A local LGBT Club was having it's party and I had the hottest outfit to wear dressed as a Stripper!From the Red Basque, Thong, Garter and Hose to the Black lace-up over the knee Boots and Sheer white Mini-skirt, I was looking as Hot as I felt!The 30 minute drive was un-eventful and the club was packed when I got there. I saw several other gurls I knew and chatted with them for a bit while drinking the first of many...

1 year ago
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Transvestite bondage

I am a transvestite and posted online that I would be available for daytime use by group of older men.On arrival I went and got changed into stockings, 12 strap suspenders, rear access panties, leather skirt, silky white blouse and stiletto knee boots. I had full makeup, jewellery, perfume and shoulder length black bob wig.As arranged I was taken by my host to the small room with no windows and as we entered I saw the stockade that I would be secured to. It was bolted onto a wooden plinth which...

1 year ago
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A Sissy Slave for a Transvestitecontinuation

Gwendolyn giggled and hung up the phone and begin to grind more exuberantly as her penis harden. Gwendolyn rode me for nearly an hour, my bung hole was full of her seed and made obscene sloppy sounds before she stiffen and flooded my bung hole once again. Gwendolyn laid there for a little while before pulling her flaccid penis from my bung hole and admired her handy work. '...Look at my cum oozing from your pussy, my girls are gonna luv you boy. I've got to get cleaned up, just relax, I'll be...

3 years ago
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A Sissy Slave for a Transvestite

I barely remembered what had happened to me, my head was spinning, my hands were restrained. My feet was spread wide and I was on my stomach on a bed in a strange room. I could raise my head, only to have it resound with thunder as my heart pumped blood through out my body. A feminine voice said softly '...I see that you are woke. Don't try to move to fast or you'll go back to sleep...' I turned towards the voice only to see a very muscular black shemale sitting in a chair stroking a very...

2 years ago
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transvestite in trouble 4 the internet porn quee

Bright light filled the room, waking me from my unconciousness.so bright it took a while for my eyes to focus. When they did the first site i saw was myself, in the wall sized mirror opposite me, strapped to the chair. It was me only now i had masses of long blode hair, tied up in 2 pigtails, loads of black eye make up and long false eyelashes, and big bright red lips. A new ball gag in my mouth, I was wearing a pink latex basque, white stockings and red slutty shoes, 6" heel with a 2"...

3 years ago
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Transvestite in a Bottle

I was born a guy in a girls body I often thought, as I was 5'3" tall and weighed 105 lbs., I had a face that looked extremely feminine with no make-up. But I WAS a guy, I had DD silicone boobs and a 16" waist, and I was extremely good looking when I was "dressed to thrill"! So it all began, one day I was searching the internet for a bra that would give me a much larger bust (I was a HUGE bust woman, man, and DD cups were NOT going to do it, for THIS girl.). And here it was,...

2 years ago
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A Transvestite Maid Who Just Wants to Please

Preface: I've only started writing recently and am keen to develop. For me the thrill of transvestism and the fantasies that surround it, is driven by what takes place in the mind. I'm hoping that my readers will appreciate Penny's journey as being something more than a sexual experience and will identify with that desire for someone else to always be in control. Penny can always justify her experiences by claiming that she was coerced unwillingly. A Transvestite Maid, Who...

4 years ago
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Transvestite Caught Conclusion

"Where are the photos?" Dorothy was standing outside the shower stall, looking in at me through the open door as I stood there, completely nude, shivering with cold and embarrassment. Over her shoulder, I saw Ronnie, the obviously gay Producer/Director. He was in on the secret of my true sex, and his eyes positively glowed as he watched me,holding his portable video camera. "Oh please don't make me do this, Mistress," I whispered in my high- pitched voice. "No one's making you do...

3 years ago
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Transvixen Transvestite Rock Band Chapter Three

Transvixen By Michele Nylons Chapter Three: No Good Deed Chelmsford Dance Hall was packed. Wendy's efforts promoting the concert had paid off. That very morning she had appeared on the local FM morning show. "So Wendy Grayson, manager of Transvixen welcome to the show," the radio DJ began. "Thank you John," Wendy responded. "So...I'm going to ask you the question that's on the lips of anyone who has seen the posters and flyers for tonight's Transvixen debut concert. Are...

3 years ago
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Transvixen Transvestite Rock Band Chapter Fur

Transvixen By Michele Nylons Chapter Four: Substitute Cherri woke up on the couch at Wendy's place and her head hurt. Panti had obviously wondered off to bed sometime during the early morning after their prolonged fellatio session and left her alone to sleep. Cherri remembered that after they had made oral love they had argued about Panti sucking off Tony Carlotta. Panti claimed she had been blackmailed into it so the band could play at the Chelmsford Music Hall but Cherri...

4 years ago
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How Should a Dominant Treat His Submissive

This is certainly a reasonable question, particularly for someone who may be just beginning to learn about Dominant/submissive relationships. So let us see if I can provide a reasonable answer.My initial response to the question may surprise some of you who are new to Dominance/submission. A Dominant should treat his submissive with respect. Mind that you do not confuse and/or conflate respect with deference. When I say treat the submissive with respect, I am not saying treat her as if she were...

3 years ago
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How I developed a crush for transvestites

How I developed a crush for transvestitesI am a 33 years old woman who loves sex very much. My name is Desirè. With my boyfriend Errol we have a very happy and open relationship. Since I am also a bisexual from time to time we make love with another woman. We also had group sex a few times. Last week I left home to go to my girl friend Natalie's summer place to have a threesome with her husband. Just when I was approaching the suburbs I noticed that I forgot my cellular phone. Since it was...

2 years ago
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Becoming a Maid for Mark and Rebecca Part Nine Rebecca Prepares Daisy for Her Master with Some Help

Becoming a Maid for Mark and Rebecca, Part Nine - Rebecca Prepares Daisy for Her Master with Some Help In Part Nine of Becoming a Maid for Mark and Rebecca, Stevie (now Daisy) shares his view of what has been happening since Ms. Rebecca called and invited him (her) to visit Ms. Rebecca and Master Mark at their new home in an exclusive area of town. Alone, I was cramping from the enema Ms. Rebecca had finished administering a few minutes ago as I waited for her to answer...

2 years ago
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Robin and Jimmy Olsen Part 2 Robin prepares Alfred beware

Robin and Jimmy Olsen - Part 2 Robin prepares, Alfred beware! by Tawny Suede The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled by the idea of smoking. But then the big change had hit him and now he thought the sight of any...

3 years ago
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Harry Prepares 4 Daughters for Marriage

Sir Harry Higgins sat in the drawing room absentmindedly reading some very dull articles about unrest on the Continent. He really had no interest in other people's problems right at the moment. Poor Sir Harry had troubles enough of his own. He had been a widower for these three years past after the unfortunate riding accident that had claimed his spouse of two decades, Lady Eugenia Higgins. Eugenia had been a shy virgin of only 16 when he claimed her maidenhead on their wedding night. It...

2 years ago
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THE 12 RULES OF THE SUBMISSIVE

1 - With your eyes down in my presence, you will keep. The submissive will strive never to cross the gaze of her Master, who is unworthy of looking at him. The exceptions authorized by the Master must be perceived by the submissive as a reward of which she is not worthy. It will therefore be necessary to keep its eyes on the ground as soon as the Master in his presence. This provision will have the effect of reminding him, if need be, of his intrinsic status as a submissive. 2 - Never will...

2 years ago
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Submissive Spirits

SUBMISSIVE SPIRITS   By LEWISCHAPPELLE Note: While this story briefly introduces Babs and David it more completely describes the relationship of their similarly unconventional friends Ann and Chip who move to increasingly greater levels of domination and submission. The story is quite lengthy but only represents a portion of a more fully developed, five work,project. While not a quick read, I trust you can take your time and enjoy this particular work and look forward to the remaining...

3 years ago
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A Mum Becomes Submissive

It had been a long day.A long frustrating day.I showed houses all day and didn't even get a bite of a sale.My feet were sore and I was cranky as I got home.I was walking up the stairs to my bedroom to get out of my business wear and stockings when I heard sounds that were undeniably the sounds of sex... coming from my son's room.As I got closer to the door, I heard Nancy, my son's girlfriend, demand, "That's it baby, ream my asshole."I froze.Nancy took it in the ass?My son fucked Nancy's...

1 year ago
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Submissive Sensibility

SUBMISSIVE SENSIBILITY By Lewis Chappelle NOTE: This story is a follow-on to ?Submissive Spirits?publishedearlier and it follows, sequentially, the stories entitled?Submissive Sailing? and ?Submissive Secrets.? New women characters are added to this piece, each with unique sensibilities and inclinations. Each piece isintended to be read as part of the entire series as no review of any of the prior pieces is provided.Let me know what you like and don?t like about it. Thanks,...

1 year ago
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Submissive Male Lessons

My assumption of you, the reader, is that you are a woman whose husband or boyfriend is sexually submissive. He may have expressed an interest in exploring this with you. Perhaps you are already exploring this dynamic but are looking for additional suggestions to try with him. You may also be a man who hungers to submit to a woman but need something to show her to give her a better idea of what being submissive actually means.I'm also assuming that both you and your partner are heterosexual....

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Four Daisy Training Prepares Her for the Workshop

Teaching the Sissy Maid Workshop at the MVP, Chapter Four: Daisy Training Prepares Her for the Workshop Synopsis: Flashing between Daisy's training before the seminar and the seminar's beginning, more is learned about how Daisy trained to be ready as Ms. Rebecca's sissy maid example and how the Sissy Maid Workshop is run to insure the transformation of the submissive male candidates into the sissy maids and cuckolds wanted by their owners. I loved the look on Daisy's face as...

2 years ago
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Submissive Satisfaction

SUBMISSIVE SATISFACTION By Lewis Chappelle Note: This piece is the last of five stories each of which follow in story line, and character development, ?Submissive Spirits? published here earlier. While it is felt that the content of each story is self contained, it is suggested that a sequential reading of all five stories, while a long read, might be preferable. Please let me know your thoughts.Thank you, LC   ?Master, I am so excited. I completed the five challenges you gave me and...

3 years ago
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Submissive Secrets

Submissive Secrets by Lewis Chappelle Note: This is rather lengthy piece and is a follow-up to ?Submissive Spirits? published earlier. It follows, in time frame and character development, the material in ?Submissive Sailing? which also was previously published here.Please let me know your reactions to this material. Thank you, LC SUMBISSIVE SECRETS Chip had started with the Thompson company as Assistant Vice President for International Operations. Chips boss reported to his...

2 years ago
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Nadines Submissive Games

Nadine’s Submissive GamesBy ReddbunnzChapter One?I’m gonna kill that fuckin’ Carol!? I mumble as Henry’s cock continues to plow into and out of my ass.  ‘Who the fuck are you kidding?’ I ask myself.  ‘You love every minute of it.  It’s consensual ass rape.  Something that you’ve fantasized about for years.  Only, it’s by the pizza guy!  Not your hubby.  Shit, the prick’s probably fuckin’ some whore in his hotel room right now!’But, in reality, I can’t believe what is happening.  Here I am,...

3 years ago
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TRANSVESTITES NOT sisterS VS ZOMBIE APOCALYPSE Ep5

All characters are over 18Béa was sexy femboy when she found a wild runaway boy. She raised him and together raised their feminine side to grow up as sisters into beautiful transvestites girls. Discovering each others body and transforming together they soon became lovers, living perfect girl life together until zombies attack the city. The girls discovered that people could be cured by having sex. Girls were on their way to inform the news star announcer Jim J.J Johns that zombies can be saved...

3 years ago
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TRANSVESTITES NOT sisterS VS ZOMBIE APOCALYPSE epi

Béa was sexy femboy when she found a wild runaway boy. She decided to take care of him and raise him like her little brother. Together they discovered and revealed their feminine side and grew up into beautiful transvestites girls. Discovering each others body and transforming together they soon became lovers, living perfect life together until… TRANSVESTITES NOT sisterS VS ZOMBIE APOCALYPSE --Name: Béa Chan --Lilly ChanAge : 23 --18Job: Student in...

1 year ago
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Wife Seeks Help In Training Her Submissive Husband

Wife Seeks Help In Training Her Submissive Husband! CHAPTER ONE. I recently discovered that my husband has been going to some ‘Swinger’ s’ parties/orgies. What he had told me was that he was going away on business trips, and that he couldn’t get out of them! Since these gatherings are normally meant for couples only, (and as he has been attending them as a ‘Single Male,’) he has had to worm his way onto the group’s invitation list by offering to ‘serve’ the guests. The organizers agreed...

Fetish
2 years ago
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Submissive Lactating MILF Becomes a Cum Dump for Her Boss and His Friends

I was born and raised in the Tampa, Florida area, just like my husband, AJ, but we did not meet until we were both out of college. We met in a bar in Tampa one night. I was twenty-three years old and he was twenty-five at the time. I was with a group of my girlfriends, and he said that I stood out to him since I was the prettiest girl in my group, and I was also more reserved and shier than the others.My name is Amy, and I am five feet and five inches tall, and weighed about one hundred and...

MILF
3 years ago
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The Submissive Position

The Submissive Position My little sister Pricilla said, “Come with me I want to show you want I learned at Jill’s house.” I knew that my sister had a sleepover with Jill the night before so I followed her into her room. She locked the door and started to get undressed. As much as I wanted that to happen I also knew that I had to get the hell out of there before I got killed. So I left. Before dinner she whispered, “I just wanted to show you the submissive position.” I asked,...

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