Outplayed
- 4 years ago
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I sat on top of the bed, waiting for him to arrive. He was late, but he
had already warned me that he would be. I didn't mind, really. It gave
me a chance to do something that I really enjoyed. I got the wait for a
sexy hot young stud while I was wearing the finest lingerie that I could
afford. It was grayish satin with lace panels. Everything from the tap
panties that I was wearing, to the bra had satin and lace mixed in. I
loved the feel of the satin against my double D breasts, and gently
caressing my thighs. It was erotic, and not many got to feel these
sensations as often as I did.
It had been a long hard road, but now that I was one of the highest paid
call girls in the city, I was loving every minute of it. My mother, also
my Madam, had been grooming me for a full 6 years, and I had finally
ripened and now it had been four years since then. Together, we had build
an empire on her hard work, and my cocksucking skills. I guess you can
say my fucking skills were also part of it, but either way, I was at the
top of the food chain in my line of business. And I loved it.
There was a knock at the door, and I knew exactly who that was. I
casually got up from the bed, and straightened my clothes. My nude
stockings were taught against my hairless legs and my garters gave a
slight tug every time I took a step forward. The five inch pumps on my
feet stomped against the plush carpet as I continued to the door. As I
walked, the sheer black robe that covered my lingerie fluttered in the
breeze I made. My blonde hair bounced a little at every step. My makeup
was flawless. Rick, the guy I was "dating", loved for me to have ruby red
lips, blue eyeshadow, extra long lashes, and just the hint of rouge on my
cheeks. It turned him on, and I had no problem giving into his desire.
I opened the door, and was greeted by the hot young stud that I had come
to know and love fucking, in one way or the other. He smiled and handed
me the flowers in his hands. I loved roses, and didn't hesitate to take
them off his hands.
"For me?" I asked with a bit of shock in my voice.
He nodded, and I motioned for him to enter the hotel room.
As a way to keep the police from locating and putting up surveillance, we
were taught never to use the same hotel room within six months of each
other. And to always make a date, and then call with our location 30
minutes prior to meeting the client. We were never allowed to go to our
clients location, or meet them. That also meant that we could never to go
with to a social function to be their eye candy. But that rule was there
also to keep us from meeting other clients and giving away that we were a
prostitute. The other part of keeping one step ahead of the police was
never allowing a client to have a cell phone on his person, and never
allowing them undress first.
It was kind of difficult to live with, but so far, after ten years of
doing this, my Madam had never been caught. She also knew how to treat
her "workers". We were allowed luxurious vacations, and usually only had
to take gigs that we wanted. Me being the exception to that rule. I had
to take the jobs she assigned to me because of my special talents. But I
didn't mind it. I was at the top of my game, so I got only the special
cases. Rick, here, was one of those cases.
"You look so beautiful," Rick said as he entered. He looked me up and
down and licked his lips.
"Why thank you," I purred. I motioned for him to start to undress and he
did so without hesitation. This time, unlike the first couple of times we
were together, he stipped all the way down to nothing, and just stood
there with a hardon growing steadily. I motioned for him to lie on the
bed, and he followed that instruction as well. "What do you want to do
first?"
He shrugged and said, "Let's just see where the road takes us."
I nodded, and removed the robe and placed it on the chair at the foot of
the bed. I then seductively removed my heels, and placed them next to
each other. Madam had been explicit in her teachings that I do everything
in a clean and seductive manner, that way I could put the client more in
the moment. I then undid my garters from my stockings and put my foot on
the bed to slowly roll the stocking down and off. I repeated this step
for the other leg. I then removed the bra, and twirled it around in the
air once. Rick got a laugh out of that. I then laid my bra on top of my
other fineries. Next came the garter belt. Finally, I put my thumbs
through the waistband of my tap panties and slowly and seductively pulled
down my tap panties. My tiny cock gave a little bounce when the fabric
finally cleared it and my cock was free. This was the one thing that I
could do over, and over again, and that would do nothing but delight my
customers. They loved it, and I loved seeing their reaction.
Now fully nude, I crawled onto the bed and slowly, but surely crawled to
where he was. I reached his not fully erect penis and took it in my
mouth. And damn, if Rick didn't get hard as a rock right then and there.
I then made love to his cock with my mouth. At first, I would kiss it,
softly and lovingly. I then licked the tip, and then I licked the shaft.
I would casually rub my hand up and down the shaft and I would bring him
to the edge of orgasm, and then stop. This drove men wild. I bet if I
was able to get hard, I would have responded the same way, but I hadn't
had an erection in ten years, when my Madam decided it was a waste for me
to become a man and started me on my way to womanhood.
"Enough, I need to fuck you, and now." I stopped playing with his cock,
and he grabbed my hairless body and with nothing but a man's strength,
tossed me on my back, and positioned himself to be ready for entry. With
my legs up high in the shape of a vee, I was ready. Years of training had
made to easy for me to accept just about any cock a man could throw into
me, and Rick was no exception. Yes, it was slow, and yes, he was gentle,
but I had absolutely no problem with him getting into me. And it wasn't
too long until he was inside of me and thrusting wildly.
It's tough to say that sex as a woman was better than as a man because I
had never had sex as a man, but sex as a woman, was great. Especially
when they hit my prostate. Some men would try and jerk me off, while
others were under the misguided thought that I'd like to be given a
blowjob. But no, my cock was only meant as a source of peeing. I had
almost no feeling down there now. I tried to orgasm once, but nothing
that I could think of could make me cum. The only time I could orgasm was
when someone fucked me.
But I was too good. My job often that of a rollercoaster. It was fun,
you spent more time waiting for it than doing it, lasted less than six
minutes, and left both parties with rapid heart beats. After that, there
wasn't much that could be done except cuddle with each other. And unless
he got hard again, I had the hotel room to myself for the rest of the
night. This time was no exception. He never hit my prostate, so I didn't
orgasm, and therefore didn't have to clean up. Him, on the other hand,
left a nice wet load in my ass.
Rick smiled, and laid down in front of me. He reached his hand over to me
to brush a couple of stray blonde hairs out of my face. "Now that that's
over, tell me a little about you." Rick said.
"What's there to tell?" I asked.
"Well, how did you become a woman?" He was frank about it. Most guys
tried to ask in another manner, trying to be suave and not get too
personal. Rick, on the other hand just asked the question. I had been
asked this question a dozen times over the years, and had always given the
same answer.
"Well, I always loved ladies lingerie, and one day, I just said, fuck it.
I've been wearing skirts and panties ever since," I lied.
"You just decided to become a woman one day?" he asked.
I nodded meekly just to keep him from going on. He was about to say
something else, so I put my finger up against his lips to hush him, and
then leaned in for a kiss. This got his attention and shut him up, at
least for the moment. He shoved his tongue down my throat and probed my
perfect teeth. I could taste the fruit he had eaten earlier in the day.
I then inched over to him, and started to fondle his cock. I played with
it, and it responded to my ministrations. Next, I moved and put him on
his back, and that's when I took control. After straddling his pelvis, I
started to rub my ass on his cock, and soon he was sprouting a full
hardon. I leaned over to kiss him, and he reached down to guide his cock
into my rear once more.
When he entered me, I gave a slight moan of pleasure. This was the best
part. This was making love, and not the fucking that I had received
earlier. He then started to thrust, and my double D breasts started to
flap into his face. After stopping the kiss, he grabbed one of my breasts
pulled the nipple into this mouth. My hair, which had been perfect was
now a tangle of blonde strands tickling his and my face. I pulled the
stray strands back, and held them there. About this time, I straightened
up, pulling my breasts and mouth away from his reach. I liked this
position. Me on top with my john on the bottom. He can only reach my
breasts with his hands, and my tiny cock slapping up and down on his
belly.
But this time, Rick lasted a while longer. After all, he had orgasmed
once before just a few minutes ago, but it didn't take that long. Another
five minutes, and he was again, spent and holding me. This time, I just
laid on top of him, my breasts pressed up against his. There were some
times when I loved the job, and other times when I hated it, but right
now, I love it. This was the type of intimacy that I had been missing all
my life. My mother wasn't the type to hold me when I was sad, or give me
a helping hand. That's okay, I always had this.
**
Rick had left an hour ago, and I was still in bed, naked as the day I had
been born. To keep the seamen off the sheets, I had gone to the bathroom,
and had an enima. It was just unsanitary to leave it up there, and
frankly, it would only get worse, so I liked to get it out as soon as
possible. But now, I was back in the bed, and enjoying post sex bliss.
My hairless body smooth up against the sheets. I ordered room service,
and was contemplating staying the night, but I knew that I had to get back
to the office at some point. Not that I would have any more clients, I
just liked being there so I could browse Pinterest and Reddit.
I finally convinced myself to get up and get ready. I grabbed my sheer
black robe and put it on, and walked into the bathroom. I didn't even
bother to close the robe, but I let it flap in the wind as I walked. My
naked and hairless skin all open to anyone in the room, which was just me.
I reached the bathroom, and admired myself in the large mirror. I was the
epitome of a wet dream for men. Long hair, blue eyes, pouty red lips,
large breasts, small hairless cock, and long legs. I was the complete
package. I could suck like a pornstar and fuck someone into a coma. I
had come a long since I was 14. From scrawny, awkward boy too hot as fuck
woman. I kissed at the image of me, and then decided it was time. I
peed, and then walked back into the main room.
Instead of dressing in the fine lingerie that I had been dressed in
earlier, i dressed in a plain pair of cotton panties, t-shirt and some
skin tight jeans. I threw on a pair of tennis shoes, and was out of the
door. The rest of my things were packed in a small bookbag. As I walked
down the hallway, men and women parted way for me to walk down. I was
confident, and they could see it in my walk. I owned this place, and the
men knew it and loved it. The woman knew it too, but hated it. I got in
my Porsche and headed back to the office, or as my Madam liked to call it,
home.
The drive was a short one, and I got there in 15 minutes. I pulled into
the driveway and got out. My Madam met me at the door, and gave me a hug.
I was a little shocked by this. She hardly ever showed affection. She
kissed me on the cheek, and that's when I knew that something was wrong.
"What's wrong, mother?" I said, suspiciously.
She only kissed me for two reasons. One, she needed me to do a favor for
her that I knew I wouldn't like. Or for a dramatic change that would alter
my life. For instance, my mother kissed me on my 14th birthday, when she
announced that we would be moving and I'd become a girl. The following
months and years consisted of training me in the arts of being a woman.
Lingerie, makeup and girl magazines had become my new obsessions.
Then came the sex lessons. But instead of getting them from the guys
perspective, I was getting them from the woman's. I was taught how to
seduce a man, and get him to part with money by stealing it. That
included trips to strip clubs to learn how to dance, and then the
champaign room to learn the art of oral sex. By the age of 16, I could go
into a fancy restaurant, take a guy home, or to a hotel, fuck his brains
out and leaving him wondering where all his money had gone. Some were
shocked and repulsed about my surprise, while others loved it. I could
fuck and suck like a pro, and my mom knew it. She saw dollar signs in her
eyes when I came home.
Another time my mother had kissed me was on my 17th birthday when she said
that I was going to be a prostitute and she was going to be my Madam.
That was a shock, but when she took me to the doctors and got me breast
implants to compliment my then B cup breasts, I knew she was serious. But
I didn't resist. I just went along with it. I mean, I was already
sucking and fucking guys, why wouldn't I just earn money doing it. And
now that I was pulling down close to 200k a year, I was content to buy my
happiness.
"Nothing. Can't I love my only daughter?" she said. I just looked at her
and she said, "We have a party, and they wanted a girl with a
little...something extra." I frowned at her, and she read my mind. "I
know we have a rule about no parties, but this guy is offering five times
your going rate." She looked at me and continued, "You can say no, but
I'd really like it if you took it."
She gave me her best puppy dog eyes, and I couldn't resist. I rolled my
eyes and said, "Okay, give me the address." As I was driving to the
event, I couldn't help but think, Well played Mom. Well played.
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