Derek Enjoys Chrissie to the Fullest
I gathered up my clothes and shoes and silently went in search of the
bathroom to freshen up, as I was ordered to do by my wife’s best friend
and my doctor, Helen. I couldn’t quite believe I had just given head to
Derek, who I had only met less than an hour ago and who I suspected was
less than a reputable figure although I had to acknowledge he had a cock
worthy of worship. It was the first time I had done that in my life and I
found the experience both humiliating and deeply erotic. Truth to be
told, the humiliation factor weighed large in my mind. I was once a
heterosexual man, albeit a willing cuckold. Now I had evolved into a
sissy cocksucker. The acknowledgement of that brought shame to me. The
humiliation of being thought of as a pansy, a faggot or a girly boy was
an emotion which was strangely erotic to me. My little prick, which was
now rendered useless by the hormone treatment I had been under for three
years, occasionally showed a spark of life and twitched involuntarily
when I thought of the superiority Derek must have felt over me as he saw
the top of my head bobbing up and down over his cock.
It made all the difference that I was told to do it by Helen who was the
woman most responsible for my transformation from a cuckolded husband to
a full blown sissy. She was the one who originally chemically castrated
me and then reversed the process and she is the doctor who has seemingly
made me addicted to the hormonal surges that wrack my body. Helen could
sense my devotion to her which was, in many ways, greater than the
devotion I felt for my wife. She knew I would obey her when she told me
to drop to my knees in front of Derek, take his prick lovingly in my
hands and lick and suck him until he exploded in my mouth. She probably
also knew that, like any sissy who has given himself to a man for the
first time, will always have that experience imprinted on his mind. It
will be the experience I will judge all successors by and nobody will
ever really give me the experience that Derek did. The prick I first
worshipped will be the cock I will always long to please.
I couldn’t stop myself from listening to Helen and Derek’s conversation
after I rounded the corner. I stopped and silently tried to hear what
they were saying. I was more than curious as they were obviously
discussing my future. I couldn’t make out their hushed conversation but I
did pick up some words and phrases like when Derek said I had "a girl
next door look" and "the punters will love her". I could hear Helen as
well as she said "no other trannies" and "that South African slut". The
latter comment made me freeze because it was an obvious reference to my
wife who Helen was purportedly friendly with. It was said with contempt
and answered with a laugh from Derek who added, "no wonder she’s such a
slut". I decided not to push my luck and quickly found my way to the
bathroom. I washed my face, reapplied my makeup, brushed my hair and took
some toothpaste out of a tube and brushed my teeth with my finger to make
sure the lingering scent of cum was gone from my breath.
I made my way back to the living room, making sure I made just enough
noise so I didn’t surprise Helen and Derek. Not knowing what to do and
not wanting to appear presumptuous, rather than taking a seat, I
approached Helen and stood in front of her waiting for instructions.
"Isn’t he beautiful?" Helen asked Derek rhetorically, giving me a
sideways glance. "He’s standing there waiting for me to tell him what to
do just like the submissive sissy I have made him."
"I am having gender identity issues with Chrissie," Derek replied with a
laugh. "I don’t know if he is a he, or a her. If he is a he, he is
certainly no credit to the male gender. He is genetically incapable of
being a woman but he looks the part and certainly can suck a cock better
than any slut I have come across."
"You should thank Derek for the compliment," Helen said with a smile,
staring me in the face. "There is no shortage of women who would give
their left arm to have his cock between their lips."
"Thank you, Derek," I stammered, blushing deeply. "I feel honoured that
you let me do that for you."
Both of them chuckled at my response and Helen motioned with her hand to
a chair which I assumed was an instruction to take a seat. I sat down,
smoothed the dress I was wearing and waited to be told what was next. I
was more than a bit concerned about the length of conversations the two
had been having about me and I was simultaneously worried that my wife,
Heidi, might be waking soon and I wouldn’t be there to serve her coffee
and breakfast, as she expects each morning. That could put her in a bad
mood for the entire day. If she had plans for a lover to visit today she
would expect the house to look spotless, the sheets to be changed and a
bottle of chilled wine waiting for her in the refrigerator. When I had
impetuously called Helen early in the morning and asked to meet for
coffee I hadn’t bothered to pick up at all before I left and I didn’t
expect our morning together to stretch on for so long.
"There are going to be some changes in your life," Helen said to me.
"First of all I have called the surgeon and we moved your operation up to
Monday at 9:00 pm. He has emailed you all the instructions you have to
follow. Secondly, Derek is quite taken with you and has decided to put
you in his stable. You should be honoured by that because he hasn’t ever
chosen a sissy boy to work for him. The work will be mostly in the
evenings and he has assured me that he will thoroughly vet the clients.
Thirdly, and most importantly, I am taking over from Heidi. She doesn’t
know this yet and won’t until it happens and you are not to say a word
about this to her. I don’t love you in a romantic way but I love who you
are and I want to protect you from things. She can’t do that. I will be
the one in charge of you from now on."
"Finally, you are a beautiful creation and you have to realise that. You
are not to be given away for free anymore. You aren’t going to be a
temporary kink for Heidi’s lovers while she is gone. If a man is going to
enjoy you he is going to pay top dollar. Derek will be the facilitator
for that and he will take a well deserved cut. That’s the price that has
to be paid for his protection. If someone is stupid enough to try to take
advantage of you then you must tell Derek. He will sort it out
immediately. Since I am taking over for Heidi I will handle your finances
and make sure that you have a good allowance. Derek will pay whatever
money you earn into my account."
I was too stunned to reply. My marriage with Heidi had lasted for over
five years, two years of being her cuckold and three years being
feminised. I know she often considered me an irritant and I knew that, in
many ways, I was just a chequebook for her. Nevertheless, the news that
Helen was taking control of my life still shocked me to the core. I felt
the colour drain out of my face as I considered all the upheaval this
would cause in my life. The next news Helen gave me made me almost faint.
"You’re so unobservant," said Helen, with a certain sharpness in her
voice. "Rob has knocked her up and he’s leaving his wife for Heidi. He
doesn’t even know that she has three or four other lovers. All he knows
is that his wife can’t have c***dren and Heidi is three months down the
line with his c***d. The idiot has asked his wife for a divorce and is
planning on marrying Heidi. She is going to have papers served on you
when she returns from our holiday. I’m sorry that I had to be the one to
tell you this but she is going to dump you one way or the other."
I felt betrayed and hurt beyond belief and, although I tried to resist
it, tears started streaming down my face. I just found out that my wife
of five years was leaving me and my future was going to entail having sex
with strangers for money.
"You’re well shot of that slut," said Derek in a gruff voice. "Helen has
more class than that South African whore has brain cells. What did she
ever do for you except cuckold you? I wouldn’t fuck Heidi with a
bargepole and if that baby she is carrying inherits her intelligence than
I pity him or her. I also pity the stupid fuck who knocked her up and is
getting married to her."
Helen rose from the sofa and took me in her arms to comfort me and I
began to realise that, if I was being betrayed by my wife, who once told
me she never wanted c***dren, and I was being traded like chattel between
two domineering women, I was actually the lucky one to have ended up with
Helen. She was an intelligent woman who understood who she had
transformed far better than the woman I had married five years ago. Helen
was taller than me, more elegant and understood me far better than Heidi.
I could never aspire to being the woman that Helen was but I could serve
her and try to please her. If she and Derek had decided that I was going
to pimped out like he did his other whores and Helen was going to reap
the financial benefits of that, whilst she provided me with whatever
allowance she deemed appropriate, then I should accept her choices for me
in life. I felt more secure when she hugged me than I had for years. I
needed someone strong in my life to guide me and Helen seemed to be that
person and, when I thought about it further, I realised my mother would
far prefer that I was under Helen’s wing than being Heidi’s husband.
"Thank you for telling me this," I said to Helen as I wiped the tears
from my eyes. "I was just worried about getting home and making breakfast
for Heidi a few minutes ago. I should have realised when I saw her tummy
swelling that she was pregnant. It just never entered my mind. I don’t
understand what she sees in Rob."
"What she sees in Rob is dollar signs," said Helen as she patted my back
and smoothed my hair. "He’s rich. But we are going to be far better off
now. You can do your freelance work in the daytime, I have my salary as a
doctor and, every night you go out to see one of Derek’s clients, that’s
another £500 for us. And there’s more. He thinks you could be in a few
sissy films. We are going to get you an agent for that. If you get a
global reputation, then rich men will pay a lot to be with you. Derek is
covering all the expenses for your boob job and he’s given me £1,000 for
a signing bonus for you. We can use that to get your mother up here to
take care of you while you recover from the op."
"Didn’t you sl**p with Rob last night?" I whispered to her, as I didn’t
want to embarrass her in front to Derek.
"Yes, I did," replied Helen, keeping her voice low. "I did it to find out
what his plans are and I guess part of me wanted to get back at Heidi for
betraying you. Also, to be honest, he’s got a big cock and he certainly
knows how to use it and I needed a hard cock last night."
"He also told me you did a cleanup job on him yesterday," she added, with
a giggle. "I guess you and I have one more thing in common now."
"Now go in the bathroom and clean yourself up," Helen said cheerfully, in
a louder voice. "There’s a little caveat to our new relationship and I
want to be part of that. I want you to look your sexiest and best for
"What’s that?" I asked.
"Derek is going to take what he deserves," Helen replied with a wicked
grin. "He’s going to bury his big cock inside you and take you like a
girl and I am going to be there to see you submit to a real man. I don’t
think you get how much that will turn me on. I am getting wet just
thinking about it. That’s the difference between Heidi and me. Turning
you into a sissy was just a means to an end for Heidi whereas I get off
on it. I love to see the hormones work through your body. I love to see
you break out into a sweat. I love your hot flashes. I love how you
become more submissive by the day. I destroyed the man in you and made
you who you are. Heidi didn’t do that."
"Most of all, I love how I will own you, how you will do whatever I want
and just devote yourself solely to me."
Helen seemed to push all the right emotional buttons in me at the same
time. It was almost overwhelming and made me want to make myself perfect
for her. I felt a rush of affection run through my body. I looked over
and saw Derek on the sofa looking at us together and taking in the power
exchange that was going on. I allowed myself to go through my own
personal Damascus conversion and let all my defences down and commit
myself to serving Helen and Derek, which meant that I was going to
surrender my body and be Derek’s next conquest and allow him to be my new
pimp and to serve his clients as best I could.. It felt right and that
knowledge empowered me to release myself from Helen’s arms and to walk
over to Derek, kneel down, unzip his trousers and take his manhood in my
I was in a dreamlike trance as I lovingly licked the helmet of Derek’s
cock. Helen lifted my dress and lowered my panties in preparation for the
ultimate violation I was about to experience. She was the one who pushed
my head away from his cock and put the lube on his member and she
positioned me on the floor on my hands and knees and guided his prick
towards my hole. I could barely comprehend her instructions to Derek as
she told him to take me hard and slow and to be very gentle at first. I
only concentrated on relaxing myself to accommodate my new lover’s girth.
The pain was intense and brought on waves of hormonal rushes that
overwhelmed me. I lost consciousness briefly and when I recovered the
pain had transformed itself into pleasure as I realised that Derek’s hard
cock had fully penetrated me and gone where no man had gone before. I
could see out of the corner of my eye Helen’s splayed legs on the sofa
and her hand, which was slowly playing with her clit, while Derek was
taking my virginity.
There were no harsh commands from Derek, just a silent acknowledgement
that he was taking what he deserved and, in so doing, concentrating
solely on pleasuring himself and, by virtue of that, Helen. For the first
time in my life I felt like I was a fully owned piece of property and the
feeling was deeply erotic. I met thrust for thrust as he began to
violently take me. His hand slaps to my ass only brought more pleasure
and made me feel more submissive. He reached up and squeezed my nipples
hard as he buried his prick in my ass. The intensity of the sensation
made my little prick twitch and, as I looked down, I could see a think
trickle of something like sissy cum emit from it. I was drenched in sweat
when I heard Derek moan and thrust his prick to the hilt inside me. I
wished I could feel his cum spurt from his cockhead as he enjoyed the
ultimate manly pleasure that I could no longer enjoy but at least could
provoke. I silently thanked Helen for turning me into the feminised sissy
I am as I found myself fully submitting to Derek’s superior will and
becoming another one of his cum sluts.
He left me spent on the floor as he got up behind me and made his way to
the bathroom to clean up. I felt like a fucked out slut for the first
time in my life as the cum slowly leaked from my hole. Helen got to her
knees and gently stroked my forehead. She lifted my legs to put my
panties back on and readjusted my bra, making sure the silicon fillers
were in properly. She lifted me up and slipped the sundress over my head
and gathered my handbag and led me out the door. All of this happened in
a daze. I found it hard to walk straight and I felt an emptiness inside
me where Derek’s cock had violated me only moments before. It was only in
the lift that I began to come to my senses. Helen had the most dazzling
smile on her face and she seemed to glow with pleasure. For my part, I
could see my reflection in the mirror and I looked like I had been well
fucked only moments before and I could smell sex on me emanating from
every pore. It was not an altogether unattractive look. Some of my
innocence seemed to have disappeared replaced by a certain sexual
maturity. I looked more like a woman than a virginal sissy.
I held Helen’s hand as she guided me out into the street. We walked for a
bit just to recover and allow me to fully come to my senses and finally
came to a bench and sat down. There was so much I wanted to say but when
I turned to face Helen I was speechless and waited for her to initiate
the conversation. Something inside me made me feel presumptuous to speak
before being spoken to so we sat in silence for a few minutes while I
soaked in the glow that Helen gave off. She finally turned to face me and
"Do we have an agreement?" Helen asked me. "Do I own you and are you
mine? Do you now live solely to make me happy, to serve me in any way I
wish? Will you do anything I ask?"
"Yes," I responded. "I will do anything for you. I am just here only to
make you happy and I am thankful beyond belief for you turning me into
who I am now. My purpose in life is only to serve you and do anything you
wish. I will be the best whore in Derek’s stable and make more money for
you than you can imagine. You will control me emotionally, financially
and physically from this day until you decide you are tired of me. Even
the freelance money I make will go into your account. I only need a
pittance to get by every day. Serving you is my only purpose in life."
"Good," Helen said with a laugh. "Now take my phone and call your mommy
and have her come up here to take care of you after the operation."
My mother’s voice was the best thing I had heard in months and she agreed
to catch the next flight to London, which would land on Monday morning. I
told her about my upcoming operation, about Helen and about my new life
and she seemed thrilled at the prospect of seeing her new son, the newly
born sissy c***d she had once played with and dressed. I also told her
that my little prick was no longer the working tool it once was and we
would not be able to play together like we used to but she assured me
that it was no great loss and it had never provided her the pleasure my
uncles had given her. She just looked forward to seeing the sissy that
she knew was deep inside me all along and meeting the woman who had
finally brought it out in me. Now she could have the daughter that she
always longed for and a new s****r in Helen.