Date: Mon, 27 Apr 2015 17:30:32 +0100
From: Nikkie Silk <nikkie.silk@outlook.com>
Subject: Jamie's Descent Part 8 TG

Jamie's Descent Part 8

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My heart soared, and I practically squealed and threw my arms around her
neck, `Yes, yes, I want to stay'.

Fiona laughed and held me tight, `Ok, OK. Let me talk to Vanessa then.' She
paused, `But you are sure this is what you want?'

`Oh, yes. I mean I'm a bit scared about what will happen, but I do so want
to stay.'

Fiona leaned forwards, wrapped her arms around me and drew me into a
passionate kiss. My eyes closed instinctively and I swear I could my heart
pounding as her tongue snaked into my mouth.  My knees almost buckled and I
felt myself surrender to her lock, stock and barrel. I had never felt this
way before; my emotions had gone into freefall as my head began to spin and
I almost fainted.  Fiona sensed this and caught me as I began to drop.

"Come on baby, let's get you to bed. I think you've had enough excitement
for one day." She whispered tenderly in my ear as she picked me up, my arms
locked around her neck and carried me through to the other room where there
was a large double bed.  I felt so safe and secure in those arms of hers as
she lifted me as if I was a child.

She laid me gently on the bed, removed my robe and slipped out of her
own. Her body looked to me like that of a goddess in the soft light from
the lamps in the room. She lay down beside me on the bed and pulled the
covers up over us. I began to shiver a little and Fiona snuggled up to my
back and wrapped her arms around me. She held me tight and my shivering
gradually eased. I could feel her breasts pushing into my back and she slid
her leg in between mine and locked together like this, we fell asleep.

I woke sometime later and I turned gently in the bed to face her. She was
still sleeping, her breasts raising and falling gently with her
breathing. I watched her for a while as she slept on, her face soft with
sleep and yet still strong and powerful. I gently moved back the covers and
looked at her breasts and the curve of her stomach as it descended into the
darkness of her groin.

I leaned forward and took her left nipple into my mouth and began to suck
gently. She stirred in her sleep but didn't wake and I continued to lick
and suck her nipple with my lips and tongue. I could feel her nipple begin
to stiffen and I sensed her begin to wake. I slipped my hand down between
her legs and began to lightly touch my fingers on her pussy. Her nipple was
now hard and she let out a small moan as my fingers danced around her pussy
lips.

I withdrew my hand and she immediately grabbed my arm and moved it back to
where it had just been.

"Don't you fucking dare stop," she growled, "or I promise I will cut off
your cock."

I giggled and allowed my fingers to probe deeper into her now moistening
pussy. She began to move her hips against my hand and I slipped two fingers
right into her. I moved across to her other nipple and nibbled it with my
teeth.

"OOOHHH," she sighed as my teeth bit down onto the nipple. She was now
pushing hard against my hand and then she wrapped her hand around my cock
which was now fully erect and I began to push into her hand. We moved
together like this for a while, our movements becoming more and more
frantic.  Suddenly she pushed my hand away, raised herself up from the bed
and pushed me down onto my back. She immediately straddled me and drove
herself onto my cock.

"Fuck me, fuck me, fuck me," she almost screamed and began to ride me hard
and fast.  I reached up and cupped her breasts in my hands and began to
tweak those rack hard nipples. She was now bucking and rearing as she rode
my cock. Her head was back and her mouth open as she drove herself and me
on. I felt myself approaching my climax but I managed to hold back until I
felt her stiffen and with a roar she fell forwards onto my chest. I came at
that moment driving myself deep into her pussy.

She rolled off me and lay next to me; our bodies now covered in sweat. She
leaned over and kissed me, mashing her lips against mine as she twisted my
nipple hard between her fingers.

"OOOwww," I said, "That was mean, what was that for?"

She smiled wickedly, "Just to remind you I'm the boss."

"Miss Fiona," I whispered, "What happens to me next?"

She turned on her side and looked straight into my eyes. She paused for a
moment, weighing up how to respond.

"Baby, you are sure you want to do this, aren't you?" Her voice was serious
and she looked concerned.

"Yes," I said softly, "Yes, I want to, but I'm a bit scared."

She looked at me for a long while.

"I guess I would be scared too, but I am going to be here and Vanessa runs
a very good operation.  She takes care of all of her people and if it's
what you want to do then this is the best place I know of."

"How does it work?" I asked.

"It?"  She looked puzzled.

"What happens here? What I will be doing."

"Well, Vanessa told you that she offers wealthy people, men and women,
discrete and customised personal services that they can trust. These are
people who will pay a lot of money for what they are looking for. Vanessa
arranges this and recruits people to provide these services. She makes sure
that she only uses the very best to provide these services and in turn they
are well paid and looked after in every sense of the word. The health and
safety of her employees is a priority for her. All she asks is that whoever
she uses is trustworthy, discrete and never, ever rips either her or a
client off."

"Is that what you do?" I asked.

She lay back and looked at the ceiling as she spoke, "Used to, baby
girl. Did it for a few years. You'd be surprised to learn how much rich
white boys would pay for a bit of this old black ass. As for you, my little
sissy, you will be the latest filly for Vanessa's old school riding
academy. Vanessa has been looking for a little while for the right person
to take on some of the clients, men and women, who have been asking for the
particular qualities you have, baby."

"What do you mean, qualities?"

She turned to look at me again, "Well there are plenty of trannies and
fembois and sissies out there but Vanessa always looks for something fresh
and she saw in you just the right combination of androgynous looks and
innocence that clients will pay a lot for. We had to break you in, of
course, but Vanessa has an eye for talent and she had you sussed out as
soon as she saw you at the bank. She wasn't wrong either, was she?"

"Nooo, I guess not," I whispered.

"Look, Vanessa will look after you and if you play your cards right you can
earn a lot of money from this. Not to mention the fringe benefits."

"Fringe benefits?" I was puzzled, "What fringe benefits?"

In answer she moved down the bed and took my cock into her mouth and began
to suck energetically, her hand getting me erect again in seconds.

"Thhessh benefisssh," is what I think she said.

I giggled and laid back to enjoy my fringe benefits.

I tried to work out what I felt for Fiona. It wasn't love in the
conventional sense of the word.  Devotion, perhaps, but even that didn't
convey the depth and complexity of my feelings for this woman who had raped
me and then cared tenderly for me afterwards. I was scared of her, for
sure, but deep down I felt she cared for me as well. She was the centre of
my life and I had given myself to her totally and would do anything for
her.

The next couple of days were pretty busy. Vanessa had come by and wanted
confirmation of what Fiona had told her. I said that, yes, I wanted to
stay. She asked me if I knew what was involved and what I would need to
do. I said that I knew only what Fiona had told me and if that was true,
then I wanted to do it.

Vanessa confirmed that was the case and ran through what was expected of
me. I would go through a period of training, developing my skills and
perfecting the look that she wanted from me. Vanessa stressed that the
clients she wanted me to serve demanded high standards in looks and
performance. I would need to practice and perfect the skills and techniques
that I would need for those clients.

She wanted me to be what she called a Trap. A boy, who dressed, acted and
looked like a pretty girl, but who could still perform as a boy if
required. I would be paid a basic salary with all accommodation and living
expenses covered, but my real earnings would be a slice of the earnings for
my services. Performance related pay, she called it. It wouldn't be that
high at first but she really believed that someone like me could earn some
serious money if I did well.

I asked if Fiona would be with me and Vanessa confirmed that Fiona would be
responsible for my `training and development plan' as she put it. It was
obvious that her training as a businesswoman was being put to a good use
here.

The next few days were intense. Fiona and Lisa drilled me endlessly in how
to walk and speak and behave as a girl. They showed me how to do my makeup
and hair and made me do it time and again until I got it right. It was
fun. I guess, for the most, but one time I got shirty with Lisa when she
criticised me for a mess I made of my makeup. Fiona overheard me shout at
Lisa and she came in, grabbed me over to a chair, threw me down on her lap,
pulled up my skirt and spanked me until my bum was red and sore. Never,
ever do that again, she hissed or you will really regret it. Oh, yes, I was
wearing girls' clothes full time now. I had been measured and either Fiona
or Lisa had gone out to buy a wardrobe for me, or rather, several wardrobes
to allow for the different tastes the clients might have.

Most of the clothes were high end fashions but there was a mixture of rough
trade stuff, as well as some little girl dresses which scared me a
little. I was made to try all of them so I could get used to wearing any of
them I was asked.

I slept with Fiona every night and we had sex of some kind every night. She
let me fuck her couple of times and then she fucked me with the strap
on. She was an energetic teacher and none of the things we did could
remotely be described as vanilla sex. She made me play the role of a girl
and that of a boy. She taught me how to respond in bed as a woman when she
took the male role and how to understand when to call a halt if things
began to get too scary.

Several nights Fiona, Lisa and I went out together with me dressed en
femme. I was terrified the first time but as it became obvious that I was
capable of not being `made' as a boy dressed as a girl and instead of
passing as a girl, I became more and more confident in my new persona.

It became easier and easier for me to think of myself as a girl than as a
boy. I was taking a selection of vitamins and pills prescribed by the
doctor, who I saw several times. Health care was, indeed, a fringe benefit
and Vanessa insisted on everyone being clean of drugs. Being found with
drugs in your system would result in immediate dismissal.

Fiona announced one afternoon that my training would be taken to a new
level and that meant that I would need to experience what it would be like
to be with a real cock, not a rubber one. She told me we would be having an
extra special session tonight. I would find my outfit laid out for me on
the bed and that I was to put it on and wait for her. I was very nervous
about what was to happen next, but knew that this was a necessary step. I
hurried to the bedroom and laid out on the bed was a beautiful Victoria's
Secret coral pink baby doll night dress set. That's not too bad I thought
and picked up the panties.

I slid the pink panties up my legs and felt them cradle my cock and balls
and I wondered if I would ever get tired of that sensuous feeling. I picked
up the nightdress and slid it over my head, it settled around my hips and
the touch of the filmy material on my skin was so arousing. The pretty
embroidered cups had small cut-out for my nipples and as I ran my hands
over them I could feel them hardening. I closed my eyes and tweaked the
nipples, an involuntary moan escaped my lips and I licked my lips feeling
the lipstick covering them.

"Don't start without me," Fiona's dark voice jerked me awake and I opened
my eyes to see her in front of me. I wondered how she managed to move so
quietly; she hardly seemed to disturb the air as she walked. I swear she
wouldn't leave footprints in the snow she moved so gently.  "Oh no. Fiona,
I mean Miss Fiona, I wouldn't dare."

She was wearing a white lace teddy with white stockings attached with
garters. Her breasts were barely contained by the flimsy garment and her
skin shone in contrast to the white of the teddy.  I stood stock still as
she walked around me, her fingers sliding over my skin so gently. She
stopped behind me and cupped my chest with her hands.

"Mmm, we'll have to something with these in the future, won't we?" She
pulled me back into her and I squirmed as she began to tease my nipples.

"Well, our little femboy likes this, doesn't she?"

She nuzzled my neck with her lips and she suddenly bit my earlobe.

"Oww," I squealed.

"Be quiet, you little pussy, or I will hurt you," she growled.

"Yes, Miss Fiona"

"Or maybe she wants me to hurt her just a little bit?" Her voice was
teasing but I had a moment when I remembered the time she first took me
with her strap on.

"Whatever you want Miss Fiona," I said obediently.

"Mmm, not yet, we have other things to learn tonight."

She brought her hands up and covered my eyes with something soft, tying it
behind my head. I could now see nothing.

"Don't touch that or try to remove it, or I will punish you."

"No, Miss Fiona."

"We will be preparing you tonight for your future work. Clients will want
to use you for their pleasure and they will be paying handsomely for your
service. They do not want just a quick fuck or suck and you will need to
learn how to give them pleasure at every moment. You must learn to give
pleasure as well as take it."

As she spoke she slowly circled me, her fingers touching and stroking me
everywhere. I could feel her running her long nails across my arms and
back. She squeezed my bum and slid her hands into my panties. Her touch was
driving me crazy and all I could do was stand there.

"To help you learn how to give this pleasure I have brought a friend with
me tonight. He will help me to teach you the skills you will need to please
the men and women you will be serving in the future."

"He, Miss Fiona?"

"Yes, he, sissy. A lot of your clients will be men and you need to
understand how to satisfy a man.  How to give and take with a man."

"Yes, Miss Fiona." I shivered with a mixture of fear and anticipation. I
knew this would happen but I was stricken with fright mixed with a desire
to explore my desires even further.

As she stopped speaking I sensed someone else was with us. I felt hands
grab the sides of my head and then I was being kissed with a tongue being
forced into my mouth. I was shocked at the suddenness of the move but
quickly recovered and started to kiss back. It was obviously a man as I
could feel stubble on his face and the kiss was hard and aggressive and
completely different from a girl kissing. This mystery man wrapped his arms
around me and pulled me strongly into his chest.

I almost melted into him and my arms went up and around his neck as he
continued his assault on my lips and mouth. His hands moved down to my bum
and he lifted me almost effortlessly up and instinctively I wrapped my legs
around his hips locking me into his arms. I could feel his rigid cock
bumping up into my bum crack and I thought he was going to have me then and
there.

Instead he walked with me still wrapped around his body over to the bed and
breaking the kiss he laid me down on the bed. I could see nothing because
of the blindfold and my hands moved up to it before I realised what I was
doing.

"Stop that, you little bitch," Fiona's voice rapped out.

I froze and felt my wrists grabbed and twisted behind my back.

"I told you not to touch that or I would punish you." She hissed.

I felt my wrists being bound together and I wriggled to resist.

"OOOWWW" Fiona must have slapped my bum hard as it stung like crazy.

"Don't resist or I will do it harder." She said "Now you will stay like
that. Might do you some good" I felt the bed move as the man lay down
beside me and resumed kissing me. His tongue was deep into my mouth and I
began to push back with my own tongue. He broke the kiss and pushed my head
down until my lips felt his nipple. I got the message and started to work
on his nipple.

I couldn't really move myself as my hands were bound and the lack of
control seemed to heighten the sensations that I was feeling. I felt he was
in total control and that seemed to excite me rather than scaring me. I
really went to town on his nipple with my lips and teeth. The nipple grew
hard in my mouth and he moved and sighed in response. I gave all my
attention to giving this unknown man as much pleasure as I could
manage. The hands again began to ease my head down and I knew what was
about to happen. I kissed him on his chest and stomach as my head was moved
downwards. All the time I had been able to feel his rigid cock pressing
against me and it felt really big.

"Open your mouth, you sissy." I had almost forgotten that Fiona was there.

I obeyed and immediately I felt his cock was pushed deep into my mouth. I
panicked and choked but the hands tightened around my head and held the
cock in place.

Fiona's voice came from the side, "Baby girl, don't worry, remember you're
a cock sucker and you like nothing more than the taste of a man's hard cock
between those lovely lips of yours."

Her voice calmed me and I began to use my tongue on the cock as the man
moved it in and out of my mouth. I could hear a slurping noise as he
continued to fuck my mouth. My lips were tight around the cock and I
struggled to breathe through my mouth. He sensed I was struggling to
breathe and he released my head, removing his cock and allowing me to gasp
some air into my lungs.

 "Now kiss the tip," Fiona's voice was low and soothing.

I did as instructed and pushed my tongue out between my lips and kissed the
tip and took the head into my mouth.

"That's good, sissy. Now, slide your tongue along the bottom until you get
to his balls"

Not being able to use my hands made it difficult but with a bit of
wriggling I made it. I licked my way up and down the shaft, feeling him
react to the sensation as I got closer to his balls. I knew what I should
do next and took one of his balls into my mouth. I rolled it around and
again I felt him react to this as his cock twitched and I swear seemed to
get even harder.

I did the same for the other ball and then moved back up and down the
shaft, this time licking and sucking as I went.  I seemed to be doing
alright and I began to relax a little and realised that I was enjoying
this. Whether it was the lack of control by being bound and blindfold or by
being at the whim of the man and Fiona, I don't know, I began to feel my
excitement building and I realised I now had an erection of my own.

I moved to the tip of his cock and took just the head into my mouth sucking
and rolling my tongue around the head. I got another twitch of the cock in
response to that and I felt ridiculously proud for having achieved that. I
began to take more of his cock into my mouth and he began to move it in and
out as I sucked for all my life. I realised that I had at least some
control over what was happening and that gave me the energy to keep doing
the best I could.

As he moved his cock in and out I felt my own cock being kissed and
licked. Fiona was mirroring what I had done to the man and it was awesome
to understand what he must be feeling. She was so much better than I was
and because I was so excited anyway she had taken me to the edge in no time
flat.

She realised this and slowed down her pace just as he was picking up
his. He began to move in and out much more fiercely and I wondered if he
was going to come in my mouth. At this precise moment I felt Fiona's finger
slide in and out of my ass. I was overwhelmed by what I was feeling; the
cock in my mouth now literally fucking my mouth, my cock in Fiona's mouth
and her finger in my ass. I felt ready to explode. One finger became two
and she was really using them hard.

The man seemed to be on the point of cumming but then pulled out
completely. Fiona also stopped and I was dumped roughly onto my back and my
panties tugged down and off. I still couldn't see anything but I guessed
what was coming. Something cold was applied to my ass crack and my legs
were hoisted up and over the man's shoulders. I felt him position his cock
up against my hole and then he began to push into me. I now realised that
Fiona had prepared me for this with her fingers and I also pushed down
against him as I had been told to do. He moved in and out against the
resistance of my ring and then suddenly he was in. It hurt as he went in
and he felt huge so I was grateful for Fiona's fingers and the lube.

He was fucking me for real now and it still hurt as he pistoned in and
out. At this moment Fiona moved to the top of the bed and squatted down on
my face facing away from the man fucking me.  She lowered herself onto my
face and commanded

"Lick me out, now you little cum princess."

I did my best even though I couldn't see what I was doing; using my tongue
to lick her pussy as much as I could. The man was now really thrusting hard
into me and I was being moved around so much as I still had my hands tied
behind my back. I can't remember when it stopped hurting so much but I sort
of gave up any resistance and started to feel only an intensity of feeling
that I had never experienced before. Lights seemed to flash inside my head
and I gave myself up to these two people completely and utterly. At that
moment I felt myself explode as I climaxed and came totally spontaneously.

I felt the man tense as he approached his climax and he suddenly withdrew
his cock from my ass and my legs flopped back onto the bed. I felt him move
up the bed and at that moment Fiona stopped face fucking me with her
pussy. He must have been finishing himself off by hand because I heard him
grunt as Fiona said

"Open up cum slut."

I opened my mouth and I felt his cum shoot over my face and some into my
mouth. I gagged and swallowed what had gone into my mouth and instinctively
I licked my lips and took what was there into my mouth as well. I have to
admit it didn't taste too bad. A bit salty and slimy maybe, but not
unpleasant. A finger, I guessed Fiona's, wiped the remaining cum from my
face and fed it to me.

I licked it from her finger almost hungrily and she kept her finger in my
mouth as I suckled on it.  I lay back, absolutely exhausted. Fiona untied
my wrists and removed the blindfold and I had to shield my eyes as the
light flooded into them. I squinted around looking for the man, but he had
evidently gone and only Fiona and I were left.

"Oh my God," I rasped, almost unable to speak.

Fiona wiped the sweat from my brow and she smiled at me, "For a novice you
did good, baby girl."

She leant on her arm and looked sternly at me, "Just one thing, don't
disobey me again like you did with the blindfold or I will really get
angry. And you don't want to see me really angry."

I cast my eyes down, "No, Miss Fiona, I won't ever do that again."

Her face softened but I didn't for a moment believe she wouldn't get angry
if I didn't do what I was told, and that wasn't something I wanted to see.

"How are you feeling?" she said, quite tenderly.

"Fucked," I said with a grimace, "but I loved it."