Transvestite Caught -- Part 1 free porn video
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 two women making love with each other, but it has
always been a particularly strong preoccupation on my part, and judging
from the number of items on the market that cater to this, I'm not alone
by any means.
I just happen to have had the means to do something about it.
You see, I inherited a rather prosperous real-estate development company,
and back when I was in College, I sowed the seeds that would make it even
more successful by persuading my mother to buy up a lot of old warehouses
along the waterfront and in the rougher parts of New York City. I picked
these buildings carefully, selecting the ones that were built solidly,
with interesting features under their grimy, dilapidated surfaces.
Mother never lived to see my gamble pay off, but pay off it did, and in a
big way, too. A few years ago, the trend caught on of converting these
old, picturesque, solid structures into condominiums for the very
wealthy, and since I owned about a dozen of the best ones, that put me
right on top of the market. Some I sold to other developers, some I
converted into condos myself, but all of them paid off like diamond
mines.
And it was when all this money started rolling in that I first started
thinking about indulging my fantasy a bit more.
I hired hookers on a couple of occasions to make love together for me
while I took videos, but the results were very disappointing. It seemed
the girls who really liked other girls were too put off
by my masculine presence.
No, I needed to find something else.
It was about that time that I picked up a magazine with a story called
"The Male Lesbian" expecting it to be about women who like to dominate
other women. To my surprise, however, it turned out to be about a guy who
dresses up as a woman in order to seduce lesbians! I quickly put it down,
slightly turned off by the idea of a man decking himself out in female
attire?.
? But there was something there that stayed in my mind somehow. Suppose,
I asked myself, just suppose I could pass as a Lesbian!
Now understand that I'm not one of those guys who would enjoy looking
like a woman. I definitely like the idea of being a man, and the prospect
of wearing women's clothes wouldn't do much for me either, since my main
objective would be to get me and my girl out of our clothes as quickly as
possible?. But like I say, somehow the notion just stayed in my mind, and
a few days later I went back to that bookstore to have another look at
that magazine.
It was gone.
And now what had been a preoccupation became an obsession. I spent the
rest of that day and all the next week searching through every bookstore
in Manhattan for a copy of that rag. And when I found it at last, I
quickly bought it and devoured that story like no other. I was hooked.
That was when I started looking through the rest of the magazine for more
information on how such a fantastic idea could be turned into reality. In
the back pages, I found an ad for someone named Frenchy who promised to
teach feminine makeup and deportment to men. The ad gave only a phone
number, which I compared to a previous ad for a boutique catering to
transvestites. Grimacing a little at the prospect of going in among such
a swishy crowd, I finally called and made an appointment for the next
evening.
Well I won?t go into embarrassing details, but over the next couple of
months, I spent two or three evenings a week at Frenchy's Place. She
taught me everything there was to know about makeup and hair-styling.
After retiring from drag-show business, she had learned the art of
electrolysis, and after some consideration, I let her remove all traces
of my beard and all my body hair except for my private area. Through one
of her former lovers, a Doctor, she was able to acquire female hormones
and shots that swelled out my hips and even gave me a small but firm and
well-shaped bust, one that I was able to hide when dressed as a man, but
show off to great advantage when dressed in female attire.
Oh yes, the female attire. Since I'm not really a transvestite, I had to
fake an enthusiasm for women's clothing. Frenchy was constantly trying
different costumes on me as my body began to change shape from the diet,
hormones, and corseting. I eventually wound up buying more clothes than I
had any intention of using; elegant evening gowns, smart party dresses,
exotic nightwear, drawers full of silken undies, shoes by the dozens, and
even some practical wear for every day.
You may wonder how I was running my business through all of this. Well
the fact is that since those warehouse/condos began to take off, I had
left most of the actual work to my very efficient and attractive
secretary Dorothy. Even before I had started on my lesbian journey, my
work day had pretty much trickled dawn to spending a few hours a week
dictating letters while I tried to look up her miniskirt or down the
front of the rather low-cut blouses that she always seemed to wear to
work.
I might add that Dorothy was a petite type, with raven-black hair and an
air of pleasantry about her. She had always been an asset to the company,
but now, as I began giving her more and more authority to run things, I
realized just what a talented girl she was.
But I had other things on my mind.
For one thing, there was the creation of my Lesbian Apartment. You see,
while I was having one of the warehouses in the Bohemian section of town
remodeled into condos, I took the opportunity to hire craftsmen to design
a highly specialized suite of apartments (for an eccentric client, I told
them.) It was actually a Chinese-box affair, with one apartment inside a
larger, heavily-soundproofed room. The inner apartment was constructed
almost entirely of see-through mirrors, lavishly carpeted and furnished,
and equipped with all the most luxurious appliances and bath fixtures.
When I was finished, the mirrored walls reflected a world of impeccable
hedonism.
But that was just the inside. In the larger, soundproofed room that
surrounded my future love nest, I installed the most expensive cameras
and video recorders, with remote-control switches that would enable me to
turn them off and on a will while in the apartment. I also put in some
comfortable chairs and a refrigerator, so that if I had company over, I
could pretend to slip out to the store for something and secretly watch
them. There were other details as well, but suffice it to say that when I
had finished, my future apartment was actually the world's most elaborate
movie set, all ready for me to start videotaping the activities of as
many guests as I could care for.
At last the day came when Frenchy fitted me out with the final part of my
female disguise. This was a small triangular net of semi-flexible plastic
that laced securely into my pubic hair, holding my manly equipment back
between my legs in a tiny package. I could urinate while wearing this
when I needed to, and the front of the plastic net was equipped with
fasteners so that I could open it and release my penis whenever I wished.
Over this plastic net, a small, exquisitely-fashioned wig was attached,
shaped to resemble a woman's pubic thatch. It even had soft rubber lips
in the center where the cleft should be! Wearing it, I looked totally
feminine, even when completely naked, yet it would be the work of only a
few seconds to remove the outer covering and release my penis for sexual
satisfaction. It was perfect!
And so at last I was ready for action.
During these last few weeks I had avoided going to the office as much as
possible, making only brief visits and intercepting occasional wondering
glances from Dorothy. I think she noticed some change in me, but whether
or not she interpreted it correctly, I couldn't say. The day after my
transformation was completed, I told her I was going on vacation and
completed the necessary papers for her to run the business completely
until such time as I chose to come back and re-assume the reins of
command. Then I moved into the apartment I had fashioned for my fantasy-
life.
Well, I'm not going to tell you about every day of my life as a Lesbian.
Suffice it to say that I managed to live out my dreams very successfully.
My normal pattern was to circulate among the many Lesbian Bars in New
York City, occasionally taking surreptitious photographs of any
interesting action with my cel phone. Being blonde and rather good-
looking, I found it easy enough to make conquests among the more
attractive ladies there, and the fact that I had plenty of money to spend
didn't hurt either.
Actually, I could have gotten a lot more women up to my place than I did,
but I made it clear that I was only out for a Good Time, and mainly
interested in Threesomes. Sooner or later, I would attract a couple of
willing, sexy young ladies up to my luxurious apartment in Manhattan's
most trendy area, where I would stay mostly in the background while my
two guests went at it. They never suspected that I was taking videos of
their passionate encounters, or that when I said I was slipping down to
the corner for more Champagne, I was actually sitting on the other side
of those heavy mirrored walls, frantically pleasuring myself with my
hands as I watched live lesbian action in my own apartment!
I particularly remember one session with two Latino girls named Maria and
Chita, sweat-shop workers who augmented their meager salaries by working
as part-time hookers for kinky ladies. Both girls were nice looking, in a
dark, brassy sort of way, but it was their infectious good humor and
total lack of inhibition that made them so popular. They were born
exhibitionists, and the mirrored walls of my lair were a real turn-on for
them. I got quite a treat that night, sitting on the other side, watching
them actually jockey each other for position closer and closer to the
see-through walls!
Afterwards, the three of us chatted for a bit, and they mentioned a Bar
that they said was even kinkier and wilder than they were. It was a
little hard for me to understand their heavily-accented speech, but it
sounded like they were calling the place Mill Sottay's or Mia Sautee or
something like that. Since I had been getting a little bored lately with
the same old faces in the same old places, I decided to give it a try and
got the address from them despite their cautions to be careful there. I
decided to pay a visit the following night.
It was located in a remodeled warehouse down near Louis Street. I watched
from across the way as women entered, either solo or in pairs.
Occasionally, I heard a curious clicking sound as they walked along. I
also noticed that when two entered together, one usually wore a cape or
coat draped over her shoulders. After a few minutes of watching, I gave
the password that Chita and Maria had passed on to me to the doorkeeper
and entered.
The first thing I noticed after I passed the entrance foyer was that the
name of the place was actually Ms. Sade's. In the dim light, I could also
see why several of the women had worn capes out on the street; their
hands and elbows were in steel cuffs! That accounted for the clicking
sound I had heard!
The waitresses wore only high heels and dog collars, with order books
hanging from short leashes clipped to the front. Aside from that, they
were completely nude, and I noticed that several of them had faint red
marks across their bare bottoms.
I had just decided that this wasn't my scene at all, and was turning to
leave when something caught my eye; I glanced over to an intimate table
for two and saw a tall, attractive redhead whose bust was bursting out of
the black basque she wore. She was also wearing a pair of red bikini
panties, sheer black stockings, and black stiletto heels. There was a
studded leather collar around her neck and a leash ran from that collar
to the hand of the girl seated next to her ?
?my secretary Dorothy!
Trying to conceal my surprise, I faded back into a dark corner and
watched. I was used to seeing Dorothy's petite frame clad in tight-
skirted suits and low-cut blouses that emphasized the fullness
of her bust and hips in contrast to her tiny waist. Tonight she wore a
blue dress with a fuller skirt, and I was soon to see the reason why!
As I quickly brought my tiny camera into use, Dorothy tugged at the leash
on the redhead's collar, urging her down to the floor as she pulled up
the skirt of her dress. She was naked beneath, and the red-haired slave's
mouth was soon put to work.
This was my chance. Circling casually about, I caught every aspect of the
erotic scene that followed with my camera. Dorothy didn't recognize me at
all, what with my makeup and carefully-styled hair, but in the pictures I
got, there could be no mistaking her raven tresses or sensuous face. I
quickly left Ms. Sade's, knowing that from now on I would live my dreams
with someone who could never say No!
* * * * **** **** * **** **** * *
Two days later I reappeared at my office. I had colored my hair back to
its natural light brown and carefully concealed all signs of my recent
feminization beneath a bulky jacket and loose-fitting pants.
Dorothy looked surprised to see me, and was even more surprised when I
told heer I was sending her an e-mail to proof and forward. She probably
thought that as Acting Head of the Company, her days as a subservient
secretary were behind her?how little she knew! I thought, as I sent the
email to her office in the next room!
"To the Site-Mistress of LESBIANS IN LOVE Weeb-site," the header must
have caught her attention and I heard an audible ?GASP!? as she began
reading:
"Attached find Twelve photographs for the Amateur Section of your Web-
site. As a long-time fan of your fine site, I'm sure that you will find
these most suitable. As you can see, they are quite candid, unposed shots
taken at a local Bar called Ms. Sade's. Notice the look of ecstasy on the
face of the dark haired--" I heard Dorothy moan softly as she opened the
attachment just as I entered to room
"Well Dorothy," I smiled, "does it look good enough to send out as-is?"
She was still looking at the pictures on her screen. Each photo brought a
little gasp or moan. When she started to delete the e-mail, I said, "It
won't do you any good. I have hard copies stored safely away?to scan and
post whenever I want!"
"How did you get these?" She looked up at me, her eyes flashing.
"I was there and took them myself," I said, smiling proudly.
"Impossible," she snapped, "Sade's doesn't allow men!"
"I wasn't exactly dressed as a man," I answered.
"Ha! I knew there was something fishy about you."
"Listen Sweetheart," I said, rising, "There may be something fishy about
me, but there's something fishy about you, too. And I have the pictures!
So unless you want to see yourself plastered all over LESBIANS IN LOVE,
you'll play along with me."
"Well, what do you want?" she asked, sullen and defiant.
"It won't be too bad," I smiled, "I want you and me to become real close.
You'll accompany me to various Lesbian Bars around town and help me pick
up other lesbians. I'll watch and take movies when you make out with your
girlfriends, and from time to time I'll join in."
'If they wanted sex with men they wouldn't be in Lesbian Bars," Dorothy
objected.
"Don't worry, they won't know I'm a man. The way I've fixed myself up,
they wouldn't suspect a thing even if they saw me naked. And if you do
your job right, they will?see me naked, that is!"
"And what do I get for setting up my friends to indulge your weird
fantasies?"
"You get to keep your cushy job, you get to keep those pictures off the
internet, and maybe someday you'll even get me," I gave her the address
of my Lesbian Apartment and told her when to meet me there.
"You can keep go ahead and delete that if you want," I said as I left,
"Like I told you, I've got the hard copies!"
***********************************
It was a busy afternoon. First, I guaranteed that Dorothy could never
under any circumstances get her hands on those hard copies. Then I set to
work on my hair and makeup.
The doorbell rang just before Eight. I had rinsed my hair back to blonde
and really dolled myself up. I was wearing a frilly pink mini-slip
lavished with lace over my bra-less breasts (which had grown even better-
shaped over the last few weeks, I thought) and a black micro-skirt barely
longer than the hem of my slip. I also wore scarlet panties beneath a
pair of bad black net pantyhose, and four inch spiked heels.
Dorothy was wearing a white Victorian-style lace blouse with a long,
free-flowing green skirt. "Is that you?" she asked, staring at me.
I pirouetted around to give her a good look, and the hem of my skirt and
slip flared upwards, so that she glimpsed my panties. She still couldn't
believe it.
"I don?t want to get personal," she gulped. "But ?ah- how did you get the
space between your legs so flat? Did you have some kind of operation?"
"Oh no," I laughed, "I'm all there under this disguise, but like I told
you: Beneath these panties I look just like a woman. I'm wearing a false
crotch-piece over my genitals that would fool anyone. Of course, if
you're in doubt, I could take it off and show you...?
"No thanks." Her lip curled slightly and she glanced at her watch. "Let's
go, we want to get to Ms. Sade's."
I said I'd prefer a place a bit less kinky, but she persisted.
"I've already called Angela," she said, "You know, the redhead in your
photos. She's going to meet us there."
That was persuasion enough for me. I grabbed my purse and a jacket to
fight off the early-Spring breeze and we left.
Ms Sade's was more crowded tonight than at my last visit, I noticed as I
checked my jacket and we entered. Angela waved at us from a booth on our
left and we made our way over to her. Along the way, several of the women
said Hello to Dorothy and asked who her friend was. I smiled and inwardly
shivered with delight at the prospect of the wild evening ahead. With any
luck, I thought, this could turn into a real Lesbian Orgy! And I Would be
part of it all... I couldn't wait to get it on video!
We finally reached the booth, where Dorothy slid in first and I sat on
the outside. Introductions were quickly made -- Dorothy introducing me as
"Gwendolyn" -- and Angela left to get a pitcher of Martinis, her bottom
wiggling in the tight blue satin dress she wore.
I spent the next few minutes eyeing the crowd and mentally noting those
whom I would want Dorothy to approach for me. So I wasn't looking as
Angela returned until I heard her stumble, and then the pitcher of
martinis emptied all over my top and skirt!
I sputtered and fumed as Dorothy started brushing me ineffectual ly with
a paper napkin. "Oh dear," she sighed, "your outfit will be ruined if we
don't get this cleaned right away. And you'd better wash, too; you smell
like a distillery. Come along."
"I'll watch your purses," Angela called helpfully as Dorothy took me
firmly by the hand and steered me through the crowd to the restroom.
Once there, she urged me into a cubicle and helped me strip off my skirt
and top, and then my slip.
"There's a room down the hall where the help changes," Dorothy said.
"Perhaps there's something there that will help get these stains out. Uh-
oh, it looks like Angela snagged a fingernail in your pantyhose when she
fell; they're all torn. You'd better just slip them off, too. I know one
of the girls will have an extra pair."
I did as she said, handing my clothing over to her, then watched her
leave, wondering what she was smiling about.
So there I was, sitting in a Ladies Rest Room wearing only my heels and a
pair of bright red bikini panties. I had just left the cubicle for a
moment to go over to the sink and wash off the liquor that had spilled on
my breasts and legs, when I heard the door open.
"So there you are. Why haven't you finished undressing yet?"
I turned around and saw a tall, muscular-looking woman with close-cut
brown hair, wearing what looked like leather dungarees. They certainly
showed off her powerful arms and massive chest! But she was still
talking:
"When I told Mala that I needed an extra waitress tonight, I thought she
knew enough to tell you that all my girls work nude."
"I-I'm not a waitress," I stammered, blushing.
"That's funny. Sandra in the next room told me that the new girl was a
blonde who had to run to the loo, and that all she was wearing was high
heels and red panties." She glanced significantly at my scanty attire.
"Listen," I said reddening even more and drawing an arm self-consciously
across my exposed titties, "this must be a joke. I'm a customer here. One
of my friends spilled some liquor on me and I just came in here to clean
up."
"If that's the case, then where are your clothes?"
"My friend Dorothy took them to be cleaned," I insisted. "You must have
seen her in the Help's Room." I suddenly remembered that my purse and the
keys to both my apartments were still out at the table, with Angela.
"There's no one in the Help's Room but Sandra," the large woman said
firmly, "and she described you. So look here: I paid Mala in advance for
your services, and I don't intend to be chiseled out of them. Now get out
of those panties and report to the Bar for your collar!"
Panic-stricken, I made a mad dash for the door. But she was ready for me.
A muscular hand shot out and closed around my wrist, spinning me back,
and even as I spun, I felt the other nimble, meaty hand grasp my panties
and tear then completely off my hips in one swift motion! Before I could
even scream in dismay, I was dragged over to a divan in the corner. The
brutal lady sat heavily down upon it, pulling me across her lap.
"Maybe a spanking will help you do as you're told!"
And she began laying into me with her hard, flat palm.
Crack! Crack!! CRACK!!
A dozen of these had me sobbing for mercy and promising to work out the
shift.But she added a few more, explaining, "A lot of the girls like to
see bottoms colored a pretty hot red. And I just love to do the
coloring!"
Slap! Smack!! SLAPP!
At last, she stood up, maintaining a grip on my right arm, and dragged me
out the door and to the bar. I scampered hunched forward beside her,
trying to keep my breasts behind the arm she was holding and my left hand
down over my pussy, to cover up as much as possible. Once at the Bar, the
large woman unceremoniously strapped a collar about my neck with an order
pad hanging from it on a chain.
"Now get out there and get to work," she snapped, "before I really get
tough on you!"
I didn't need to be told twice! Quickly as I could, I walked through the
crowd towards our booth, trying to forget my awful nakedness. But as I
passed among the amorous lesbians, I was fondled, patted and pinched by
everyone within grabbing distance. One woman even had a ping pong paddle,
which she used on my glowing bottom as I scampered by. At last, I reached
our table, only to find a stranger seated there alone!
"About time you got around to me." She smiled. She was an oriental woman,
petitely built, with a hard glint in her dark eyes. "I seem to have
dropped something under the table," she said softly, "fetch it for me!"
I wanted to stop and ask her where my friends had gone, or if she even
knew them. But the note of command in her voice was unmistakable, and I
didn't want to get a bad report sent back to my "boss". Meekly, I dropped
to my knees, lifted the hem of the table cloth, and crawled under.
"It's over here by my chair," she prompted. I crawled over and sure
enough, felt something silky under my hand.
It was a pair of panties.
As I picked them up, I suddenly felt the oriental woman's fingers twining
firmly into my blonde hair, pulling my face between her spreading legs. I
felt her slender thighs wrap around the back of my neck, pushing me
closer. Before I could even protest, my mouth was in her bush. I knew
what was expected of me, and gave it everything I had, tonguing and
sucking until she moaned with delight and loosened her grip at last,
permitting me to crawl shamefully out from under her table and resume my
"duties".
It went that way the whole night. I was pinched, poked, prodded and
pulled all evening as I serviced the tables in every way imaginable. I
was on my knees so much that I felt like a scrub-maid! The time dragged
on, and I saw no sign of Dorothy or Angela. I wondered vaguely (when I
had moments to think) what the girls would do when they searched my
apartments and failed to turn up the photos. They'd have to come back for
me then, I thought. At least that's what I hoped!
It was nearly Closing Time when I finally had a chance to duck back to
the Help's Room and look for something to wear home. To my dismay, the
room contained no loose clothing at all; just a few well-secured lockers.
What could I wear to get home in?
I glumly approached Freda, the woman who had forced me to work, and told
her of my clothing problem. She immediately told the couple of dozen
patrons left in the Bar to quiet down:
"Gwendolyn here." She pointed at me and I blushed and quivered under the
collective gaze of the aused lesbians. "Has just told me that some thief
stole her clothes and she can't get home!"
There was an immediate outbreak of laughter from the crowd and shouts of
"Poor Baby!" from a few of them.
Freda continued, "I don't have any clothes to give her, but I'm sure
she'd be very very grateful to anyone who'd lend her some!"
There was a stir from the back of the crowd, and four or five of the
older, uglier Lesbians, who hadn't connected with anyone that night, came
forward. None of them looked like the type who would just loan me some
clothes and let me go, and I was about to back out when I suddenly felt
something cold and hard close about my wrists. Freda had handcuffed me!
Aeryn
- 07.06.2020
- 10
- 0
