Complex Relationship With First Client
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Caught Out By Client free porn video
Caught Out By A Client
Penned by: Miss Deborah Leigh Johnson
Setting
Steve Kliner has been a client of mine for nearly ten years. He has a lot of life
insurance and mutual fund investments with me.
Steve is rather an enigma to me. He is in his mid thirties, six foot tall, with
the physique of one who obviously works out often, no fat on him at all. He
has sandy brown coloured hair, and these piercing light blue eyes that let you
know almost every emotion that man is feeling. I often thought that he would
be excellent husband material, and I could never understand why some
attractive woman had not stolen his heart yet.
He always makes me feel kind of inferior, almost submissive to him, though
I would never dream of ever letting him know that he makes me feel that
way. You see, I am only five foot four and slim. I feel quite intimidated by
his presence, even if I do like him a lot.
I like Steve, and we have become good friends over the years. I have made a
lot of money from his business, and I have made him a lot of money too.
For some reason, over the last three months, he has been starting to just drop
in to my office, without making an appointment first.
That is what led up to a rather fateful Thursday afternoon.
The Beginning
I had just gone through a company sales campaign and I was exhausted.
True, I am an independent financial advisor, but I place most of my business
with one particular company, and I place enough business with them that they
include me in all of their local competitions.
I had made nearly $30,000 in a matter of five weeks. I was elated, but I was
also drained. I desperately needed a vacation.
So it was that I was sitting at my desk about mid to late afternoon, with my
feet up, and just considering taking the rest of the week off. I sure deserved
it.
It was at that point that Steve dropped in.
I was always happy to see him, because I liked him. I also liked that we had
become friends over the years.
He smiled and sat down as he usually did, and asked me if I had any coffee
on. I did, and I rose to go to the back of the office to get him a cup.
When I returned, I was surprised to see that he was watching me with a most
curious expression in his eyes.
I surrendered the coffee I had gotten for him, and sat in my big chair behind
my desk again.
"Dirk, can I ask you a personal question?"
"Sure Steve. I consider us to be personal friends, not just a client and agent.
What is on your mind?"
"Why do you wear women's clothes?"
I was stunned.
I sat and stared at him for a very long moment. How had he ever guessed? I
was too careful to make a serious mistake.
"Uhhh, what do you mean, Steve?"
"What I mean is this. If I took that tie off, I bet that I would find that the
buttons on your shirt button on the wrong side. I bet that If I took your
sweater vest off, that I would find that your pants zipper on the wrong side
too. Not only that, but your pants are a light cream colour. If a person looks
hard enough, they can see a trace of your pink panties under them. And, I
know damn well that men can buy shoes with Cuban heels, but those are not
men's shoe's either, are they?"
He had me.
I swallowed a large painful lump in my throat. My hands were shaking. I felt
as though I had just entered the twilight zone.
I looked into those pretty blues eyes of his. There was no malice. There was
just a look of curiosity.
"To be honest Steve, I do not know why I wear them. I have just always felt
more comfortable in ladies clothes than I have in men's clothes. I have felt
this way all of my life. I do not know why. I just like it better."
"Do you like to wear dresses and skirts too?"
"Yes. I like to wear everything that is pretty and feminine." I felt my face
burning at my confession.
"I bet you look pretty."
"Uhhh, I think that I do."
"Do you have any pictures of yourself all dressed up?"
"Yes."
"Can I see them?"
"You, you really want to see pictures of me dressed up as a woman?"
"Yes. I do. Do you mind showing them to me?"
"Uhhh, I guess not?"
I got out my picture album and watched with great fear and trepidation as he
slowly turned one page after the other. There were about forty pictures in the
album. When he was finished, he turned back to the one of me in a French
Maid uniform.
"You know, if you wore that, I would let you come over to my place and
clean my house for me."
He grinned wolfishly at me, and I felt like a lusted after woman. I loved how
it felt too.
"You would?"
"Hey, you are a pretty good lookin' lady. I would not throw you out of bed
for eating crackers, as the old saying goes."
I was trapped. My feminine vanity had been fired.
"You think I am a good looking woman, Steve?"
"Let me put it this way. If you were wearing a dress right now, I would not
think twice about asking you to come out for a romantic supper with me."
"Wow. You, you are a guy, and if I was wearing a dress, you would ask me
out on a date?"
"Haven't you ever dated a guy before?"
"No. I always thought that that would be kind of queer."
"Have you wanted to date a guy?"
"Well, I love to feel like a woman, I will admit that. And it is a normal thing
for a woman to date a man, and I kind of want to experience everything that
women are allowed to do. So, I guess that I could say that I might like to date
a man?"
"How long would it take you get all dolled up?"
"Usually about an hour."
"Here is the drill. I am going to go away and I will come back in an hour.
You put on something pretty for me, and we will see how good you look in
real life. If I think you look good, I will take you out for a nice dinner, and
maybe some dancing?"
"Steve, I am not a fag, okay?"
"What makes you think that I am? What I see is a lovely feminine woman
with a wee bit extra in her panties. I do do not see a guy in a dress. I am not
gay either, okay? Let's just see if we can have some fun with this, okay?"
"Okay Steve. I... I will get ready."
"What do you call yourself when you are a girl?"
"Deborah, or Debi, with one 'e' and one 'I'."
"Cute. All right Miss Debi, I will be back here in an hour."
The Next Step
I dressed nervously. Sure, I was confident that I looked enough like a
woman to go out and drive around the city, but I had never dated a guy
before. I had never let anyone see me really close up either. My hands had to
be calmed before I attempted to put on my eye liner, or there would be an
awful mess, I knew.
But I finally got dressed.
I wore a new pink blouse that buttoned like a shirt, but in the front panel
where it buttons, there is an intricate white lace design down the front. With
it, I chose to wear a new suit I had just gotten. It was a dark purple, two
piece. The skirt was a little long but when I wore heels, it actually made me
look trimmer than I really was. I think that it was the longish single breasted
blazer that enhanced the look. Anyhow, I as quite pleased.
I checked my delicate wrist watch, touched up my hair and put on a final
spritz of perfume. I was ready for my first date with a man.
My heart was beating wildly. I knew that I wanted this, badly. I wondered if
he would like me enough to kiss me, and to hold my hand when we walked
down the street. I desperately wanted to know what it felt like to be treated
like, and to act like a lady on a date with a man. I'd fantasized for years, and
now I could hardly believe that it was about to happen for real.
I felt quite flattered that Steve had taken this initiative. It must mean that he
really liked me.
I heard a rapping on the office door, and I looked around the corner to see if
it was Steve or another client. If it was a client, what could I do? I could not
let a client see me dressed as a woman. Word would get around, and my
business would be ruined for sure.
It was Steve.
With a deep sigh that was designed to muster all the courage I could find in
me, I left the bath room and walked to the door. I unlocked it, and Steve
came in. He stood for a long moment in front of me.
I had a myriad of emotions and thoughts as he stood there. One thing, I
realized for the first time how big a man he really was. Even in my three and
a half inch heels, I had to look up to see into his eyes. It made me feel small
and dainty, and I loved that feeling. I blushed. I realised that I had always
been looking at him before with boy eyes, but now I was seeing him with my
girl eyes.
He was really cute. I noted the light shadow of a beard. Yes, he was cute. I
had never thought of him as being a cute guy before, but now I could admit
to myself that I did think that Steve was cute.
I felt so small and delicate. His eyes were slowing taking in my effeminated
image, and he made me feel like I was being examined by a lustful dirty old
man. I liked that feeling too.
I lowered my eyes.
As I did so, I noted a slight stirring in the front of his pants. When I saw that,
I felt my panties instantly bulge with my sensual excitement. I was glad that
my skirt was not a tight fit, or he would know for sure what I was feeling. I
did not want to be excited by being with a man, but I could not deny that he
made me feel very feminine and attractive to him.
"Well? Do you think that I look like a real woman Steve?"
"I think that you look like a woman who needs some loving."
Then, before I could stop him, he took my hand and pulled me out of the
office. Fortunately, I had my purse with me. I was so scared. Nervously, I
turned and locked the door. The cool autumn breeze played with the hem of
my skirt and I loved how it felt on my nyloned legs. It was so sexy.
He took my hand and led me over to his car. Though it was still only late
afternoon, it was starting to get dark already. I stood passively by, as he
unlocked the passenger door of his car, and helped me to situate myself in it.
I was glad that it was a long skirt, as the seat was low, and if it had been a
mini skirt, Steve would have seen my panties for sure.
Soon, he was in the car and we were pulling out of the parking lot. Once we
got onto the main street, he reached over and took my left hand in his right
one. He was holding my hand, like he would if I was really a girl. I was
thrilled to be able at long last, to be treated like a woman, and to be expected
to act like a woman is allowed to act.
I knew he would be disappointed if I did anything that might seem to be at all
mannish to him. This was a dream come true for me. I felt as though I were
trapped into being completely feminine, and it felt wonderful to me. I looked
down at his big hot hand clasping my, laying on my lap, right on top of my
pantied erection. I knew that there is no way that he could not know that I
was excited by this experience.
I kind of hoped that I was just as exciting to him as he was to me too.
We made our way to a restaurant that I was well known at. Being single, I ate
in restaurants most of the time. I was scared and tense when we drove into
the parking lot. Steve, sensing what I was feeling, just stared long and hard
at me for a few minutes.
"Do you really think that anyone who knows you as a male is going to think
that you look anything like that old self tonight?"
"I, I guess not? I just never did this before, Steve. I am really scared. Can we
go somewhere else?"
"Hell, if you are going to be my girlfriend you had better get used to the idea
of going where I want to go. Got that Miss Debi?"
'Girlfriend?' Did I hear him right? Did he want me to become his girlfriend?
Wow. I had never imagined that something like this might happen. How did I
feel about being a girlfriend?
I loved it.
Then a sobering though smacked me with its reality. Girlfriends have sexual
relations with boyfriends. Did Steve really expect me to be all girl, like all the
way?
Submissively, I lowered my eyes and nodded to him that I was accepting of
his conditions. I felt so weak. I felt submissive, and the feelings made me
feel feminine. This was far more than I had ever fantasized about. This was
the real world of girl hood.
He went around to my side of the car and opened the door. He reached for
my hand to help me get out of the low riding car. I was glad. From that
angle, I needed his help to get back up onto my high heels. Girls, while they
have many advantages in life, had some disadvantages too. Though I
cerebrally knew about them, it had never really entered into my
understanding. Now, I was finding out what it really was like to live in a
feminine reality.
I loved it. I wished it could be forever. I wished that I was a real girl, so
Steven could marry me, and I could take care of him, and be taken care of by
him. I looked at him, and I felt a warmth in my heart, as I wondered what it
would be like to be his wife.
We entered the restaurant, and I was amazed to find that Steve had
reservations. He had reserved a front row table. Everyone in the restaurant
would see him sitting with the womanized me. I would have no escape.
Everyone would be watching me act like a woman.
But, wasn't this the kind of reality that I had wanted anyway?
I felt every feminine stitch that I was wearing, as we made our way to the
table. He had already ordered my favourite poached salmon dish too. It
occurred to me that he must have been pretty sure of his way with me if he
had done this already. It also occurred to me that he must really like me to
have gone through so much effort for me too. He was trying to impress me,
and he was doing a good job of it too.
The waiter pushed my seat in under me, as I lowered myself, remembering to
smooth out my skirts under me as I sat down. Steve was a wonderful host to
me. He kept the conversation going, but it was not the conversation that I
was used to. This was the conversation of an amorous young man, trying to
impress and perhaps seduce a young lady of his choosing.
He soon had me aware that I had drunken to much wine. I was elated. I
found that the slight edge from the wine gave me just that much freedom to
act the way that I had only dreamed of acting before. I now knew what it felt
like to reach across a table in a public restaurant, and lightly caress the back
of a man's hand. I knew what it felt like to look up into a man's eyes, and see
that I was wanted as a feminine person. I knew what it felt like to have a man
reach over under the table cloth, and run his hand up under my skirt. And,
for the first time in my life, I knew what it felt like to have a man touch my
cockette through my panties.
Yes, I luxuriated in being treated like a woman. I luxuriated in the pleasures
of being allowed to act like a woman who was being seduced too. It was
wonderfully freeing to me. I felt, for the first time in my life, like I had
become a whole personality. I loved the newly emerging Miss Debi too.
The dinner was prolonged but not boring. It was ever so stimulating to be
treated like a woman, and I ate up every second of the experience. But, alas
all good things come to an end. Before I knew it, it was nearly eight.
Steve asked me if I was going to take the next day off. I told him that I really
wanted to.
He smiled and then said that if I did not have to be in early, why not go to his
place for a night cap?
He made it sound so reasonable, that I agreed. It was only when we got out
onto the highway that I remembered that he lived in an old farm house about
ten miles outside of the city limits. What would I do now?
He reached over and took my hand again, only this time, he pressed the back
of his hand down into my pantied little cockette. He told me that he was really
happy that he was turning me on so much, because I was really turning him
on. I was not gay, and neither was Steve, but I felt nice about what was
happening.
Then he took my hand, still in his, and placed it on the front of his pants.
I had never touched a man like that before. It was really hard and I could feel
the heat of it right through his pants. It was nice. I felt quite feminine, and
quite natural.
Soon, we drew up to his front door. He again helped me from the car, only
this time, when he pulled me up, he pulled me into his arms. I yielded
submissively to his wishes. I wanted to please him.
I soon felt his hot hands on my bum cheeks, pulling me up to meet his lips. I
sighed as the man kissed me. He was so different from the girls I had kissed
before. His lips were so big, and so thin and hard. I liked it. I wanted him to
know that I liked his kissing me. I parted my lips, and he took the hint that I
accepted him, and I wanted him to invade my body.
His tongue was massive as it slowly licked my lips then entered into my
mouth. He pulled me tightly against him, and I felt his big hard on for me. I
did not know whether I should be ashamed that he was treating me like a
fairy, or be pleased and flattered that as a lady, I was exciting to him.
The latter won out. Soon, I found myself responding by sucking on his
tongue, and pressing my tummy against him to encourage him to take me
further in my experience as his girlfriend. Yes, I wanted to become the
feminine woman that he would allow me to be for him.
He lifted me and carried me into his house. There was no fan fare. There was
no pretense. I knew that he wanted me and he wanted me to please him. And
I knew that I wanted to please him.
He carried me up the stairs and lay me on his bed. I lay there, marveling that I
was getting to see him the way the other girls saw him. He smiled at me and
he slowly removed his clothes. Then, he was naked, and he had a huge
erection, aimed right at me. I'd never been in this position before, and I liked
it. I loved being the sought after prey of a man on the prowl. I liked feeling
like his prize to be taken.
Then he lay down, right on top of me. I had never felt the weight of a man on
me before, and I loved it. I wrapped my arms around his neck to let him
know that I accepted him. Then for the first time, I also felt a cock poking at
my panty crotch. I opened my legs to let him know that I liked that too.
I felt the hardness pushing up at the panties, right where my vagina would
be, if I had one, and I wished that I had one for him to slip that massive thing
into. I would love feeling like I was his conquered lady, taken and possessed
by him.
He lay on me and kissed me for a very long time. I have no idea of how long
it was, as it was all like a dream to me.
Consummation Of My Role
"Debi?"
"Yes Steve?"
"You know how you turn me on, and I know how I turn you on." With that
he reached down and for the umpteenth time, he fondled me through my
panties.
"Girl, you gotta relieve me. You give me blue balls, you are so hot, and I
gotta get some relief."
"What do you want me to do Steve?"
"Honey, if you was a regular girl, I'd be fucking you. You ain't though, no
matter how pretty and how feminine you are. But, girls like you can please
their men in another way."
"You... You want me to suck your cock, don't you Steve?"
"Hey, all the other girls do it. Why should you be any different?"
He looked down at me with that oh so superior masculine expression that
says, "I am right, how could you not agree with me?" look in his eyes.
I lay their, totally aware of my utter effemination. He was right, I had to
admit it. But he also wanted me to answer him. He wanted me to humiliate
myself in front of him.
"Well? Why should you be different than any other woman I have dated,
Miss Deborah?"
"No reason I guess?"
I felt the flush of humiliation wash over my psyche. I had just told a guy that
there was no reason why I should not suck his cock. What was wrong with
me? I should be screaming and fighting with him. I should be trying to
preserve any shred of masculinity that I had ever had. Instead, I was dressed
as a woman, laying in a man's arms, and I had just told him that if he wanted
me to suck his cock for him, that I could find no reason not to do it.
Did I want to be able to look in the mirror tomorrow morning, and know that
I was looking at a cock sucker?
I knew for certain that I did not want to think of myself as a fairy. I did not
feel like a fairy. I felt like I had at long last, been allowed to feel like a
woman. I knew now that I wanted to look in the mirror in the morning, and
know that I was looking at a woman who had done what normal women do,
with their boyfriends, the men that they love.
I did not know what to do, so I wrapped my hand around his cock again,
amazed at how big and hard he could get. I felt so flattered that I could make
him react to me like this. He was reacting like this, I knew, because of my
femininity.
Not know what else to do, I began to kiss down his cheek, down over his
chin, down his neck and ever so slowly I kissed down through his chest hair,
down to his tummy. Then, I slowly moved down to kiss his chest, I
masturbated him. I felt so completely natural pleasing this man, the same way
that his girlfriends pleased him. I wondered if he like me enough that he
would want to go out with me, like go steady or something? I hoped so.
Soon, I had kissed my way all the way down, so that his cock was actually
touching my face.
I smelled his strong masculine musky scent. I had never smelled that man
smell from myself. Nor had I ever wanted to smell it. I stopped there. His
cock was so big and so ugly. It absolutely fascinated me.
It looked so right, wrapped in my pink tipped fingers. There was nothing
about me at the moment that was male.
Yet, I had lived with a life time of conditioning. To dress in girl's clothes
when you are a boy, and then to make love to a man, was the lowest form of
life on the earth. That was what I had always been taught. But, it felt so right
to me to be doing this. I knew I was not a fairy. I had a male body, but my
feminine nature was expressing herself now. I felt like a she, not a fairy.
Could I actually find from within myself, the courage to break all the taboos?
As I watched the thing throbbing in my hand, it occurred to me that maybe I
should see if I could kiss it first.
It jerked and hit me on the nose as I moved my lips towards it. But in
seconds, I felt my lips kissing the dry hardness. I could hardly believe that I
was actually masturbating a cock, and kissing it. But somehow, as I was
kissing him, a new emotion intruded on my reality.
I had the sense that he was a man who enjoyed being a man, and I was most
definitely not. A person like me should be honoring a person like him. As I
kissed, I began to kiss him with the passion of one who loves honors and
respects. Yes, he was a man, and I did not want to be. He deserved my love
and adoration for being what I could never be.
It was not too long before I began to wonder what his cock would taste like.
As I kissed it, I let the tip of my tongue touch the head. It was salty. I liked it.
I began to lick it with just the tip of my tongue, hardly daring to believe that I
was really doing what normal women were allowed to do. I had no idea of
how many girls had done this to him before me, but I felt pleased to be
counted amongst their ranks. He would never let a guy do this to him.
My licking got a bit braver. I began to taste his shaft then I licked all over the
big ball of his cock head.
I was making him moan and writhe around under my. I felt good that I could
make someone feel so good.
Then, I knew that it was time.
It was time for me to suck his cock.
I opened my mouth as wide as I could, and I rested my lips on it. Then I
slowly lowered my head. I felt his satiny smooth hardness as it very slowly
passed over my sensitive inner lips, and I felt his cock enter into my mouth
and press against my tongue. I felt it bulge out my cheeks.
When I started to gag, I knew that I had taken too much in.
I moved around so that I was kneeling between his legs. I looked up at him.
He had that masculine superior look written all over his face, with the
obvious pleasures that I was giving to him.
I felt so completely submissive to his masculine personality. I loved the way
that felt. I wished that I had a camera, so that he could take a picture of what I
looked like as I looked adoringly up at him, with his cock deep in my mouth.
He grunted, and I felt him grow bigger. His eyes rolled back as they closed,
and I knew I was in for it. I felt the first powerful blast of his ejaculate as it
hit the roof of my mouth. Then another, then another. He filled my mouth as
he rolled around and told me what a hot fantastic bitch cock sucker that I was.
I loved hearing those words in my ears. I knew that to his mind, I was not a
guy anymore, and I would never be. Every time he looked at me from now
on, he would remember what I looked like made up pretty, with his cock in
my mouth. I liked knowing that, because that is the way he thought of his
previous girlfriends.
I moved my head back to catch it all, and I gently massaged with my thumb
on his glans. He rewarded me with more of his ejaculate. I thought that it was
funny that I should think of it as a reward, but then ever since men have
lived, women have tried to attract them to themselves, so that they could
receive their ejaculate with in their bodies, just as I was doing at the moment.
It was only natural for a woman to think of a man's cum as her reward. After
all, did she not compete with other women to get it for herself?
He stiffened, then he slumped.
"Gawd Deborah, you are fantastic. I have never had such a good blow job.
Geeze, it must have something to do with having such a big clit in your
panties, eh?"
I took my mouth from him, keeping my lips locked so that I would not spill it
all over the bed.
He smiled at me. "All loving girl's eat the cum that they have sucked from
their men Debi."
Shame washed over me. But, as far as I knew, he was right.
So I swallowed, thinking of the millions of male sperm trying valiantly to
impregnate me. This is what women did. I knew now that I loved being
allowed to do what women did. It made me feel complete. What really made
me feel good though, was knowing that Steve did not think of me as a guy,
but as a woman that he has had a romantic date with, then he brought her
home and conquered her.
He told me that he was so tired that he was not going to drive me back to the
city. He told me that he would like me to spend the night with him, in his
bed, like a loving woman would do. I complained that I did not bring any
overnight stuff.
He smiled and told me that his sister's room was right next door, and we
were about the same sizes, so I could us whatever I needed. He smiled and
told me to go an put on a pair of really sexy baby dolls, and if I was nice to
him, he just might throw a good fuck into me.
I felt like an exasperated woman, and I threw a pillow at him as I rose from
the bed to go to the room next door.
Such was my introduction to the life of womanhood.
Steve and I live together now. I still go to my office every day, but more
often than not, I am wearing a mannish cut ladies suit, a blouse and lingerie. I
have a wide selection of mannish looking ladies shoes as well. I have not
worn male underwear in many months.
When I am at home, Steve gets upset if I am not wearing dresses or skirts,
unless it is sexy night wear or really short tight shorts that show off my bum
cheeks.
I have assumed the role of his wife. He introduces me to new people as his
wife too. I did not know any of his friends before, so that is not a problem.
They all think that I am his woman, and I am contented with that role in life.
I love taking care of a man the way a husband expects for his loving wife to
take care of him.
That is the story of how I was caught out by a client.
You can drop me a line if you like at: [email protected]
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