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At the age of 7, my older sister bought a pair of red patent leather
stiletto shoes which she wore every time she went on a date with her
latest boyfriend. I was fascinated by them and used to playfully wear
them to hobble down the hallway as she chased and chastised me for doing
so. I didn't realise at the time but this was the start of my trip into
transvestism and I soon found myself delving into the laundry basket to
retrieve a pair of her lacy knickers and bra which I would don in the
privacy of my own bedroom. The biggest turn on would be to find spunk
stains in my sister's knickers and I would masturbate furiously whilst
imagining what it was like to be fucked in the red stilettos.
I was in my early 20s when, one day, I found myself shopping for some
clothes in the local shopping mall. What I really needed was a new shirt
to go to the pub with my mates but as I inspected what was on offer in
the shop window, my eyes rested on something entirely different - a pair
of shiny red patent leather stilettos, identical to the ones that my
sister used to own! My heart raced as I took a trip down memory lane and
before I knew it, I found myself clutching a carrier bag containing my
new purchase. The salesgirl had looked at me with suspicion until I
explained that they were for my girlfriend as a birthday present - I
don't think she entirely believed me but then I didn't really care as I
knew I would soon be out of the shop.
I had been on shopping trips for girls clothes before though - mostly
lingerie but also the occasional dress - so I had grown accustomed to the
reactions of the sales staff which didn't deter me but did mean that I
had started internet shopping more regularly and tended now to only buy
impulse items in public.
I rushed back to my flat and was so busy fantasising about my new heels
that I ran straight into a woman who lived in the flat next to mine - she
was also rushing round the corner of the hallway in the opposite
direction to me. The result was a collision of bodies and a bump on the
head for me. I must have been concussed because the next thing I remember
was waking up on my brown leather sofa with a cold flannel pressed
against my throbbing forehead. The recollection of what had happened
began to surface through the dull ache in my head. However, the pain
subsided as I looked around to see where I was and how I had got there.
I was in my own flat, alone, but how I had got there was not clear. I
remembered running into Linda, my neighbour and so assumed that she had
managed to get me inside before leaving - she was in a rush after all.
I rose to my feet, feeling a little dizzy, and went to the tiny kitchen
to look for some pain killers. A few moments later, I felt much better
until I suddeny realised what I had been shopping for! The red stilettos!
Where were they ?!
I rushed back to the living room but there was no bag and no shoes. Maybe
Linda had put my bag in the bedroom. I opened the door and sure enough,
the bag had been placed on my double-bed. There was just one problem -
the shoes were not in the bag.
Instead, the sight that greeted me made me freeze in my tracks, As I
stared at into the room, laid out on the bed was a purple lace basque,
matching purple stockings, thong, black leather mini-skirt and see-
through black lace top. Placed neatly on the floor, were the shiny, new,
red stilettos.
I was in shock. The only possible explanation was that Linda had done
this as nobody else would have had access to my flat - but why ?
I was still contemplating the reason for Linda's actions when the shrill
sound of my mobile phone interrupted my thoughts. I picked it up off the
bedside cabinet and answered.
"Hello," I said.
"Hi James," came the reply, "it's Linda here. How is your head sweety?"
"It's, erm, okay, thanks," I stammered, unsure of how to deal with the
situation I found myself in.
Linda must have known what I was thinking. "I was on my way to a job
interview," she offered, "but because of our little, erm, mishap, I was
late and didn't get the job."
The kindness in her voice had been replaced with a more menacing tone
which made my heart race even faster than it was before.
"Have you been into the bedroom yet?" she asked coldly.
"Er, yes, I have - listen I know what this looks like but ...." Linda
interrupted me, "no need to make up excuses James. If I'd known you were
a little sissy boy before then I would have known what to expect. Imagine
the shock when I opened your wardrobe to look for a blanket to cover you
with only to see all those lovely, sexy dresses and things."
I stayed silent - she knew what the score was and I knew that I couldn't
explain my way out of this one. It was at this point that Linda played
her trump card.
"James, I hope you're not going to be annoyed with me but, whilst you
were lieing there asleep, I took the liberty of looking on your
computer." "Hope you don't mind but I've taken a copy of your photos, I
especially like the ones of you with the dildos in your arse."
MY heart sank, I had taken hundreds of photos of myself in all sorts of
female outfits, in lots and lots of sexy poses incuding some hardcore
ones. And now Linda had a copy of them! I was frantically wondering what
she wanted - money I suppose - when once again, she read my mind.
"I don't want your money sweety," she started, "I just want some fun -
and some payback for you making me lose that job today!."
I took a deep breath, closed my eyes and asked her what kind of "fun" she
had in mind. If I had been worried before, then I was more worried now.
Linda explained that she would be home at 7pm and that she would be
expecting me by 7:30pm at the latest. The only thing was that I was to
wear the clothes she had laid out on my bed. At first I refused but Linda
threatened to email all my work colleagues and friends with the photos
and I knew that I had no choice. She had also downloaded my address book
from my email account. I really wished that I had password-protected my
PC now, but it was too late. I tried to find out what she intended to do
with me but Linda refused to answer and ended the conversation with a
thinly-veiled threat not to be late.
I dropped the phone onto the bed and sank into the soft duvet, thoughts
racing through my confused head. What the hell was I going to do! Linda
had my photos and any attempt to disobey her would end up in ridicule for
me. After 20 minutes or so I decided that I had no option but to do as
she had demanded. I glanced at the clock and saw that it was already
4:30pm - that gave me 3 hours to get ready.
Right, I said to myself, if I'm going to dress up, I'll make sure I look
bloody good.
I started with a bath, followed by waxing my legs and arms - I already
waxed regularly and had silky smooth skin. Next, I plucked a few stray
hairs from my eyebrows and carefully applied my make-up. Foundation to
ensure no traces of stubble could be seen, dark blue eyeshadow, black
mascara and eyeliner and finally a purple shimmery lipstick to finish
off. I had been dressing as a girl for many years in secret and so make-
up was easy for me to apply.
I chose a long black curly wig - one of many that I had purchased over
the years.
I fastened the purple basque over my 36c false boobs and carefully rolled
on my stockings. The black leather skirt clung to my bum and the lace
blouse looked great over the basque. I carefully eased my feet into my
shiny red stilettos and glanced at myself in the mirror. I had to admit
that I looked good - the perfect tart. My shiny lips were my best
feature, followed by my stocking-clad legs and cute bum. The red shoes
were lovely and made me feel very dirty. My cock had started to stir and
precum oozed into my knickers.
But the uncertainty of what Linda was up to soon made it disappear. What
could she want from me - more humiliation I suppose. I had made her lose
her job so she wantedme to feel bad too - that had to be it.
The clock ticked around to 7:28 and I was just about to open the door to
cover the 4 steps to Linda's flat when I heard voices on the landing. It
was the couple from across the hall. I waited until they had entered
their flat before stepping out into the sparse hallway.
I teetered in my new heels and the lining of my leather skirt swished
over the top of my stockings. I knocked on Linda's door, willing her to
hurry up and answer before somebody saw me. After what seemed like an
age, the door swung open and I was greeted by Linda.
But it wasn't the Linda I expected. This Linda was wearing a black PVC
catsuit, her red hair tied back into a ponytail and in her hand was a
leather riding crop. I was stunned and my jaw fell open in disbelief.
"You are late!" she snarled, her face distorting with rage. She grabbed
my arm and pulled me into her flat, slamming the door shut behind me. I
fell forward onto a green velvet armhchair which winded me slightly. As I
tried to stand up again, Linda pushed me over the arm of the chair so
that my curved bum was thrust into the air. Before I knew what was
happening, I felt a sharp sting across my buttocks as the riding crop
whacked against my leather skirt.
"Ouch!" I shouted.
"Shut up faggot," replied Linda. I hadn't realised how strong and tall
she was until now. She continued to beat my arse with the riding crop
holding me down with her free hand. The high heels and tight skirt made
it impossible to stand.
By now tears were streaming down my cheeks and soaked into the green
velvet as I sobbed with each stroke of the riding crop. Eventually, Linda
stopped and allowed me to stand up.
Linda handed me a tissue which I used to wipe away the tears.
"Can I go now?" I asked when I had recomposed myself.
"Certainly not!" laughed Linda, "I have plans for you my little queen,"
she added.
She reached behind the sofa and retrieved something which made my eyes
widen. It was a huge black strap-on dildo. Linda carefully fastened the
straps around her pvc-clad thighs until the hard rubber cock pointed
forward menacingly.
"Okay Sissy James - no, I mean Sissy Jane," she corrected, "if you don't
want this to hurt your tight little bumhole I suggest you start
lubricating it with your mouth - suck my cock bitch!"
I had no desire to be ridden at all, let alone with no lubrication, so I
knelt in front of Linda and gripped the hard black ruber cock with my
hand. I guided the head into my mouth and began to fellate the artificial
cock. Linda thrust forward, burying her penis as far down my throat as
she could. I gagged but managed to take it, my saliva glistening along
the full length of it's ebony shaft. My mouth ached with all the sucking
and slurping. Linda instructed me to "moan like the sissy whore that you
are" and I obliged.
Eventually Linda removed her cock from my throat and made me kneel on all
fours, my arse pushed up high into the air. I felt her long fingers
probing my hole, and thankfully, the cold refreshing stickiness of some
lubricating jel. I glanced backwards and saw Linda greasing up her black
pole. She gripped my hips and eased herself into me. I felt my hole
stretching as she pushed further and further, my sphincter muscles
stretched as I endured the pain of the black dildo sliding into me.
"Do you like that, you little whore?" she panted.
"Oooh yes, that's good, keep fucking me please," I pleaded as the pain
gave way to pleasure. Linda obliged, as she began to plunge the cock in
and out of my arse faster and faster. Her long nails dug into my fleshy
hips as she pounded me harder. I could feel and hear her pvc thighs slap
against my buttocks with each thrust and knew that I was taking all 10
inches of the thick, black dildo. My own cock was rock hard and covered
in pre-cum.
Linda fucked me hard and fast, my face pressed into the carpet, and I
found myself pushing backwards to meet her forward thrusts, just like any
other female slut. After what seemed like an eternity I heard Linda begin
to moan and knew that she was about to orgasm. She flung her head back
and gave one final, deep thrust with her cock as she screamed with
ecstasy. Her body gradually relaxed and I felt the emptiness as she slid
the black dildo out of my hole.
Linda made me stand and knelt in front of me to take my hard cock in her
mouth. It was my turn to fuck her throat. She licked and slurped on my
throbbing hard-on and it took only a few minutes before my cum gushed
into her mouth. My cock plopped out of her mouth and Linda stood up and
placed her lips against mine. She had retained all of my cum and she now
trasferred it from her mouth to mine. I tasted the familiar saltiness of
my own juice mingled with the taste of her lipstick - it tasted great and
I swallowed very drop with a gulp.
"There's a good little Sissy," she purred. "Now then, take off your skirt
and go into the bedroom," she ordered.
I did as I was told, and as I entered the bedroom was greeted by the
sight of a king-size bed with cast iron headboard from which dangled
leather wrist and ankle cuffs. Linda pushed me forward and told me to lie
with my back on the bed which I did. My arms were held above my head as
each wrist was fastened into the shackles. Linda attached a wide spreader
bar between my ankles and this was held high into the air by a hook and
chain suspended from the ceiling so that my knees were above my tummy and
my bottom fully exposed. Next came a ball gag which filled my mouth and
prevented me from speaking. Linda then left the room leaving the door
ajar.
I began to wonder what she had in store for me when I heard a knock at
the door followed by the sound of voices. My heart beat faster with both
excitement and fear, not knowing what to expect.
After a few minutes the door opened and in walked Linda followed by 3
huge black men! All 3 had more muscles than I knew existed and their
biceps rippled as they stared at me.
"This is Jane, your fuck whore for the evening," Linda smiled. "She's
yours to fuck as you see fit," she added. My eyes widened at her words
and I suddenly realised what was about to happen.
The 3 men undressed revealing massive black cocks which put Linda's dildo
to shame.
The first man approached me and smiled broadly, stroking his long penis
as he did so. He climbed onto the bed and positioned himself at the
entrance to my male pussy which was still slippery from the dildo
fucking. He eased his huge cock into my hole and it felt like I was going
to tear in half! The cockhead wasn't even in yet and already my arse
burned with the pain. Eventually the head passed my sphincter and I felt
the shaft digging it's way inside me stretching and pushing it's way into
me. I gasped with the pain and the man grinned. At last I felt his thighs
on my butt cheeks and knew that he was all the way in. He began to slide
in and out, slowly at first but gathering pace as he went until he was
fucking my hole with some ferocity. The bed squeaked and bounced as I was
banged harder and harder. His large hands lifted my bum of the bed as he
raised the spreader bar and fucked me mercilessly.
I squealed with pleasure and pain as I was roughly violated.
I opened my eyes in time to see Linda blowing one of the other black men.
Her mouth struggled to accomodate his meat, it was so big. As I stared
the the third black man approached and removed the ball gag, replacing it
with his own cock. I stretched my lips around the thick shaft and licked
and teased the head. He reached down and held the back of my head as he
began to fuck my mouth. Saliva and precum leaked from the sides of my
mouth dripping down my cheeks.
Meanwhile the man fucking me was approaching his orgasm and I felt his
loins tremble as he emptied his black seed into me with a hard thrust.
His spunk jetted into my arse as he grunted with pleasure. As he
withdrew, the spunk ran down the crack of my arse.
The man I was blowing was also approaching orgasm. His huge cock twitched
and I struggled to take all of his sticky sperm as it filled my mouth and
overflowed down my chin. As he withdrew he was replaced by the third
black man who Linda had been sucking off. He rested the tip of his penis
on my shiny lips and wanked the foreskin until he shot his sticky juice
over my face and neck.
My bum ached with the fucking it had received and my face and mouth was
covered in sticky spunk which was running down my cheeks and dripping
onto the bed.
I was exhausted - I had been fucked before but never gangbanged by 3 big
black men - it had been fantastic! I felt like such a dirty, used whore.
Linda escorted the 3 men out of the flat leaving me on the bed.
When she returned it was with a camera and she took various pictures of
me, still covered in cum and shackled to the bed.
"Well done Sissy Jane," she congratulated me, "that's gone some way to
repayin the debt you owe me."
"What debt?" I stammered.
"Okay, I'll be honest," said Linda, "I'm actually a prostitute but
business has been bad recently so I needed to spice things up a bit,
offer my clients something different. I was on my way to meet a young
transvestite who had agreed to work with me - but our little accident
meant that he was nowhere to be found when I finally got to our meeting
place. So imagine my surprise - and joy - when I discovered a real-life
Sissy living right next door!"
Linda went on to explain that from now on I would be helping her out on a
regular basis as her Sissy whore as and when she wanted me to and that
she would publish the pictures if I refused.
Of course, I had no choice but to agree to her demands. And secretly, I
was lookig forward to the next session.
Avriella
- 04.07.2021
- 12
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