Chapter 6
Mommy Returns
So much had happened in the last few days. My wife’s best friend had
confided in me that my wife of five years, Heidi, was three months
pregnant with her lover’s baby and was planning on serving me with
divorce papers when she returns from holiday next week. That same woman,
who just happened to be my doctor and was the person who had administered
my three year course of oestrogen treatment, had now declared her
interest in me, not so much as a prospective spouse but as a benevolent
owner who was soon to reap the coming rewards from my upcoming career. In
blunt terms, my new vocation was going to be prostitution, of the
kinkiest sort, under the tutelage of a rather evil, but strikingly
handsome and well endowed, underworld figure or, to use an even blunter
term, an upmarket pimp. We had ‘run into’ Derek whilst we were having
coffee in a bistro in Notting Hill, although, knowing Helen, the
accidental meeting was anything but an accident. My seduction this past
Saturday was almost far too perfect to have been left to chance. Helen
knew all the right buttons to push in my mind to get me on my hands and
knees and virtually beg Derek to take away my virginity. And he did it
with relish, knowing that I would be hard pressed to ever find a man who
would dominate me like him. That’s what pimps have been doing for
centuries and it’s why they can build up a stable of naive girls who will
fuck any punter that comes along and willingly hand over their cash to a
man who knowingly holds them in contempt.
Why am I so drawn to Helen? The answer is almost too complex to go into
but it helps that she is beautiful, elegant and intelligent enough to
know how to transform a heterosexual man into a full blown sissy and then
manipulate that man into doing whatever she wishes. I can’t help but be
drawn to her. She knows that the shame I feel and the humiliation I
experience when I look in the mirror and see an almost perfect facsimile
of a very attractive petite young woman with blonde hair almost to her
shoulders, a slim body and, what Helen describes, as legs to die for. I
didn’t seek this future out. I can’t blame my wife Heidi for it. I knew
when I married her that she was a slut and would never be faithful to me.
I was the one who let himself be led into Helen’s surgery, like a dog on
a leash, and given the first shot of the d**g that would chemically
castrate me and I watched as she filled up the first hypodermic needle
with a massive shot of oestrogen that would begin the process of
feminising me. I did it almost in a daze. I was trying to rid myself of
the jealousy I felt every time my wife came home in the morning with that
just fucked look in her eyes and it worked a charm. It worked so well
that I no longer have to take the chemicals that once castrated me but I
live for the Friday mornings when I lower my panties and Helen sticks
that needle in me and pumps me full of the hormones that give me the same
hot flashes that older women experience in menopause.
Each rush of the feminine hormones makes me even more submissive. Helen
knew that on Saturday I would be putty in her hands. I even told her the
one great secret in my life that I had never confided in anyone before.
Now Helen knew that when I as 13 years old I secretly spied my mother
cuckolding my father with my well endowed uncle and shortly, on that very
afternoon, I was undressed and led to bed by that same woman and actually
begged her to let me go down and taste her juices and my uncle’s semen
and that we continued that relationship until I was 25. My mother and I
eventually had full sex together but on every afternoon she was
unfaithful to my father she knew I longed to taste her and, over time, it
just became the most natural thing for me to come home from school, take
my clothes off and join her in bed where I would lower my head and lick
the residue of her lovers and taste her moist pussy. I became adept at
bringing my mother to one powerful orgasm after the next.
Helen also knows that when I was 18, after my father died, my mother
would playfully dress me in her clothes every day. It helped that we were
both petite and slim and actually had the same shoe size. I only wore
men’s clothes outside the house. When we would dine together we would
dress in skirts and heels and she carefully taught me how to be feminine.
My long hair was kept back in a ponytail and I was taught me the art of
skilfully applying makeup. Even though we had a very active sex life
together I inherited the same masculine equipment as my father and some
of his effeminate traits and could never provide her with the rough sex
she craved from my uncles. I had to acknowledge from a very young age
that there were better men than me who inherently knew how to satisfy the
cravings of a woman like my mother.
After I had revealed my dark secret to Helen she made me call mother up
at her home in Sydney and ask her to visit and to take care of me after
my breast implant operation whilst Helen and Heidi were off in Ibiza for
a week enjoying the sun and the inevitable sex with dark and handsome
men. My mother was arriving with the full knowledge that I had been
feminised by Helen and now could no longer even lay a claim to being a
man. The best way I can think of to describe myself is as a sissy and, to
be honest, I am a far better sissy than I ever was a man. I am the sort
of sissy that gets straight men off. I know that and the attention that I
get sometimes overwhelms me. I am totally passable and, after the hormone
treatment shrunk my penis to less than an inch and made it incapable of
ever getting hard again, I can tuck my tiny testicles up inside me and
except for a very slight bulge in my panties, straight men never think
they are looking at anything less than a real woman when they see me. I
have a feeling that when I begin my work as a prostitute the superiority
they will feel when they pull their stiff cocks out and compare them to
my little soft sissy penis will only make them feel more dominant and
masculine. I don’t think fucking a sissy girl is a homosexual act and I
think most straight men agree.
As I sit in the recovery chair after my operation, with my new breasts
aching, bruised and sensitive I can at least take comfort in the fact
that my body transformation is complete. On Sunday the back of my neck,
which is normally covered by my blonde hair, was tattooed discretely in
tiny script declaring that I am the ‘Property of Helen Duprey’. That
tattoo fortunately went unnoticed by my wife and, as she is leaving me to
marry her lover soon, I doubt that she will ever know it exists. Mother
and I are going to stay at my home until Helen returns and then I am
moving in with her and mother will linger for a few weeks in my place
before she returns to Sydney. Derek expects me to start work at the
upscale brothel he owns in Mayfair that very same week and the surgeon
who did his work on my breasts told me I should be able to have a fairly
active life in seven days although there will be some tenderness and I
should not let my clients play with them roughly. He was paid for by
Derek so he knows that I will be his first sissy to work for him and he
made sure that my breasts look as womanly as possible. I wish I could
touch them but they are safely and firmly held in a surgical bra, which I
will have to wear for five days. My new bra size is a 34B. I didn’t want
big tits. I wanted breasts to match my slim and petite figure.
Thankfully I never had to get butt implants. As my mother always told me,
my butt is far more feminine and firm that most women’s are. My waist is
tiny in comparison and, now with my new breasts, my figure should be near
perfect. I have always had tiny feet for a man and my hands look
perfectly feminine. My Adam’s apple was lopped off two years ago, so any
telltale signs of masculinity have been erased, except for that one tiny
detail that Helen says I should never touch. She wants me to keep my
little prick and testicles to remind me of the man I once was. She finds
it deeply erotic that she changed me from who I was to who I am today and
she actually gets turned on by seeing the physical results of the hormone
treatment she has administered to me over the years. She will sometimes
flick it or delicately hold it between her thumb and index finger and, as
she does, I can see her flush with excitement.
My prick is sensitive to the touch and I love it when she does that to
me, but I don’t think it will ever get hard again. I know it will never
regain the four inches that it has lost in the last three years and my
testicles will forever remain tiny and shrunken. That’s not to say that I
have no erotic thoughts. I find my complete submission to Helen erotic
and I love the feeling of deep humiliation I get when I compare myself to
a normal heterosexual man. I have never harboured homosexual urges but
what I find deeply appealing is the power exchange I feel when I kneel
down or bend over and allow a real man to take pleasure from me. Derek
was the first man to do that to me and it only happened about two days
ago but I knew from the moment I took his large prick in my mouth and he
thrust deeply in my ass and shot his cum inside me that my destiny was to
give pleasure to men. When my surgeon took me into his office for a
private consultation when I arrived at the clinic in the morning it felt
perfectly natural and right to kneel in front of his open legs, to undo
his trousers and to take him in my mouth and bring him to a strong
climax.
One of the things I grasped immediately about the difference between how
heterosexual men treat sissies, as opposed to real women, was the utter
disregard they felt for them once they had used them for their private
pleasure. It was a conflicting experience for them; a sexual kink they
only sought out on an irregular basis and when they had spent their seed
they were done. There was no subsequent tenderness afterwards, only an
urge to put what had just occurred out of their memory and not to
confront the fact that they had just had sex with someone who was
genetically in the same gender as them. In reality, which became apparent
to them just after their orgasm, they had committed a homosexual act
whilst their whole persona totally conflicted with that. Real men don’t
brag to their friends about nailing a sissy, but they will boast about
bedding a real woman or even paying to have sex with a common whore. They
will even say tender things to a prostitute after they have paid her to
suck them off in a back alley but once they have violated and used a
sissy, they tuck their cocks back in their pants and they are off without
so much as a post coital acknowledgement.
The doctor whose cock I had just lovingly sucked could barely look at me
after he had cum in my mouth and I had sucked his prick dry, but that
suited me perfectly. The shame I felt when I saw his superior sneer as he
looked down at me while I was still on my knees in front of him with his
semen s**ttered on my face and in my hair made me blush with shame but,
at the same time, answered a deep submissive need in me which was first
probably instilled in my psyche when I first begged my mother to let me
taste the mixture of her juices and my uncle’s thick semen which was the
residue of their violent coupling. I remember her shocked look when I
asked her to let me go down on her just 15 minutes after I had witnessed
her making love to my father’s b*****r and I remembered her understanding
smile when I finally came up to kiss her with my lips covered with the
mixture of love juices. It was not just that one experience that made me
crave submission. Our relationship took a real twist once she began to
understand what I craved. Every morning she would grab a glass before she
went to the toilet and released the pressure from her bladder. The first
taste of her pee in the day was always reserved for me and it was often a
heady mix of semen and urine which I drank eagerly. She did that at my
request.
I saved up the money and bought the riding crop that I often begged her
to use on me. The first time she whipped me she was uncomfortable but she
eventually began to enjoy the sound of the smack of the crop on my ass,
my jerking body as the pain transmitted to my brain and the residue of
redness she would leave after a heavy session of punishment. She learned
to love the erotic pleasure of it and would be wet when she finished a
heady session which left me throbbing with pain. Then she needed to make
love to me and had violent orgasms when I went down on her.
I begged her to let me lick her clean after she had emptied her bowels
later in the day. The first time she acquiesced to that request was a
shock to her and she felt uncomfortable with me licking her soiled ass
clean but it eventually became a daily ritual which she enjoyed. No
longer was it necessary to use the toilet roll. My tongue did a much
better job. I longed to taste every part of her and when she realised
what joy that gave me she willingly obliged every submissive quirk I had
and began to revel in the erotic power she had over me. She began to
teach me how to become feminine, how to dress like a girl and how to make
my young face into a palate that, with the right application of makeup,
could be made into a facsimile of a young girl.
Thereafter I became not only her occasional lover, but her willing
servant. I took over all the household chores and personally took care of
every need she had. When I was at home with her alone I dressed as a
girl. I cooked the meals, cleaned up afterwards and made sure that our
house was spotless. I hand washed all her lingerie and changed the sheets
on her bed after her lovers had soiled them. I listened as she told me
how my two uncles were far more endowed than me and knew how to satisfy
her better than I could or my late father ever did. She ingrained in me
the sense that there were far better men in the world than me for women
like her which eventually made me readily accept my role as a submissive
cuckold in my marriage to Heidi. My mother shaped me into the person who
willingly gave up his manhood and allowed himself to become the sissy I
now am, surrendering whatever rights I had as a man and willingly
becoming the property of my new owner, Helen. My mother knew that my
frequent blushes of shame reflected a need to surrender myself to someone
superior to me and the fact that I now was the property of a woman three
inches taller than myself and who I felt almost in awe of was the
ultimate culmination of my fate.
There was a power paradigm that went through my relationship with my
mother. My total and complete submission to her became her liberation as
a woman. She became more confident in herself and didn’t judge herself
solely by what her lovers thought of her. She grew tired of my uncles and
sought out men that would bend to her will and devote themselves to her
happiness. Her current husband is the polar opposite of my father and his
b*****rs. He is phenomenally wealthy, younger than she is by a decade and
solely committed to her happiness, allowing her to have her sexual
freedom whilst he is bound only to her. My mother made me who I am and I
made her who she is. The liberation of a woman requires the total
surrender of a man. I sacrificed my manhood willingly so she could become
the independent, confident and wonderfully wicked woman she is today. Now
I am going to become a kinky sissy prostitute, satisfying the whims of
real men for the financial rewards Helen will reap. I have freely given
myself to both women in my life with my eyes wide open and now there is
physical evidence of my submission in the statement of ownership that is
tattooed on the back of my neck.
It was 3:00 pm when my mother finally arrived at the clinic in Kensington
to pick me up. She had arrived on a morning flight but had to clear
immigration and customs at Heathrow, drop her luggage off at my house and
then take a taxi to get me. At 55 she still looks like the beautiful
woman who raised me. There are some lines around her eyes but she is
slim, tanned and stunning enough to pull off an over the knee skirt and a
blouse unbuttoned low enough to see the top of her firm breasts. We
kissed, not like mother and son, but like former lovers, which seemed to
shock the nurses. When I finally stood up, she was momentarily taken
aback as she studied me from top to toe.
"You look like a beautiful young woman," she exclaimed. "I should have
put you on hormones when you were a teenage boy, although then we
wouldn’t have been able to do what we used to do."
"Thank you," I said with a smile, still a bit groggy from the
anaesthetics I was given before the operation. "I don’t feel so hot now
but in a few days I will be up on my feet and will be able to take care
of you instead of you taking care of me."
As we left the clinic and walked outside to the waiting taxi I clung on
to my mother’s arm in order to steady myself, silently cursing myself for
wearing heels, and let her open the door to let me in. When she got in
through the other door and slid next to me she grabbed my hand as we took
the short ride back to my house in Notting Hill. She glanced down at the
hem of my short blue dress and saw my stocking tops which were held up by
a feminine suspender belt. She gave me a devilish smile as she lifted my
hem slightly to expose my creamy white thighs.
"Are we going for the full on slut look?" she asked teasingly. "What
happened to the sweet little boy who would secretly wear my tights and
knickers under his school uniform?"
"The boy in me is a distant memory," I said with a laugh. "But you are
still the sexy knockout you were when I was a teenager. If I could get
hard now I would love to take you right to bed."
"Your voice has changed so much," she said as she played with my hand.
"When I look at you and hear you speak you sound like you were born a
woman. I have to confess that I can’t wait to see what your little cock
and balls look like now, if you still have them."
"They’re still there," I said, blushing at the humiliation I felt every
time I looked in the mirror and saw my shrunken cock and balls. "I feel
ashamed when I look at them but Helen insists that I keep them."
"I agree with her entirely," she said, looking at me in the face. "As
soon as we get back to your house I want to see what remains of your
manhood. I want to touch the little prick that used to be inside me and I
want to hold the testicles that once produced the love juice that filled
my pussy."
"You are still the naughtiest woman I ever met," I said with a giggle.
"Most mothers would want to make their sons chicken soup after what I
have been through and you want to play with my useless cock."
"Most mothers don’t have sons that are sissies," she replied with a laugh
as she opened her rather large handbag to show me what she had brought up
from Australia for me. "And most mothers wouldn’t be looking forward to
using this on their sons."
As I stared at the long black dildo in my mother’s bag I could feel a
wave of erotic energy rush through me and I realised that, at last, the
tables had turned in our relationship and my mother would be the one
fucking me in the future. When we arrived at my house and my mother
reached into her purse to pay the taxi driver, I gently let myself out of
the cab and made the short walk to the front door. When we finally made
ourselves into the living room I collapsed on the sofa and my mother sat
next to me and held my hand. She then went to the kitchen to make us tea.
When she came back and handed me my cup, the first sip began to revive me
a bit. We sat in silence for a while before my mother began to get
curious and lifted the hem of my dress up to reveal my panties. She
couldn’t help herself as she pushed them aside to examine my little prick
and balls. I could see a smile slowly spread on her face.
"My God," she exclaimed as she broke out in a laugh. "Helen is absolutely
right. Your prick is the cutest little thing I have seen in life and your
tiny balls are adorable. To think this was once what was inside me is
just amazing. I love it more now than I ever did when I was younger and
it suits you perfectly."
"Look, it’s leaking too without even getting hard," she added as she
continued to hold it lightly in her fingers, touching the sissy cream
with her index finger and holding it up to examine it. "I know what you
want me to do with this."
She slowly lifted her finger to my mouth and watched as my tongue licked
it clean and then she touched the head of my prick again and took the
leaking semen and rubbed it on my lips.
"We are going to have such fun while I am here," my mother said with a
smile of joy on her face. "Right now I really need to pee. I hope you
left a glass near the toilet for my golden nectar. I want you to get used
to having me inside you again."
"I don’t think of as a glass anymore, mother," I replied. "In my mind
it’s a chalice. I wouldn’t want a drop of it to go to waste."