Sissy Stepson 10 Stepmother s Sissy
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Sissy In The City free porn video
SISSY IN THE CITY
by Charlotte
sissy_charlotte@s...
This story contains scenes of an erotic nature, and is
not intended for minors. Further if such material is
considered illegal in your area, you should bypass this
story. This story remains the property of the author.
Permission is granted to download, photocopy, copy
and re-post so long as any such action contains these
disclaimers, and no attempt is made to profit from
this story.
I am a 29-year-old guy living in England. In most
respects I have a normal life. I think readers might be
interested in me because 10 years ago I spent three
months in California on a work visa program. Lots of
students have been on these programs over the years
but I think I must have been the first one to spend the
summer as a waitress and sex toy of a rich
businessman.
When I arrived in California I already had a room
booked at a cheap, run down hotel in the centre of
LA. I didn't have a job yet but I wasn't worried
because I had a lot of money with me. A few days
after I arrived, I was on my way back to the hotel one
night when I saw a sign for a transvestite club.
I'd always been turned on by the idea of dressing in
girl's clothes, but never had the guts to do anything
about it. Eventually I decided to go in and take a
look around. The first thing I saw when I walked
through the door was a group of gorgeous women
dressed as waitresses. They were wearing very
skimpy, black satin, French Maid's uniforms with
white piping. The uniforms had a short skirt and low
cut top, and were worn with sheer stockings with
seems running up the back, four inch spiked heels,
layers and layers of white petticoats to push out
their skirts, black elbow length gloves, a black choker,
mop cap and a large, white, frilly apron tied with a
big bow at the back. I must have stood there with my
mouth open for 30 seconds. I realized they were guys,
but I couldn't get over how good they looked.
Eventually, I found my way to the bar, and after a few
drinks, I started chatting with one of the waitresses.
As I was obviously a foreigner on my own, she started
asking me about myself. I figured that I was 8,000
miles away from home and unlikely to run into
anyone who knew me so I was totally honest (plus
I'd had a few drinks by now!) I told her how I'd
always been turned on by the idea of dressing like her,
but never had the courage to do anything about it.
Sophie immediately called over her friends to hear my
story. It turned out that most of the girls shared a
house a few miles away and my fate was decided!
As soon as their shift was over, I was taken back to
their house to play dress up. I had a few more drinks
when we arrived for courage and soon found myself
dressed in a corset, stockings, white blouse, black
pencil skirt, low heels, make up and wig. I was
amazed when I looked in the mirror, I always thought
I'd look like a guy in a dress, but they had made me
look just like a young career woman. I was thin,
weedy, and short as a guy but I looked really hot as a
girl. Dressed like that, I obviously needed a female
name and they christened me Charlotte.
Pretty soon, I was spending as much time as I could at
their house. I borrowed clothes from all the girls and
was soon accepted as one of them. It took me a
little while to get the voice right, but if I was careful, I
could pass as a woman. After a few days, they even
managed to persuade me to go out with them
while dressed?once I realized nobody knew I was a
guy I had a great time. A few nights later, I was at
the club with them, wearing a beautiful
green silk dress, with very high heels, when they
introduced me to their supervisor. He was so
impressed he offered me work covering for one of the
waitresses who had twisted her ankle. At first I was
scared by the idea - going out dressed in the
evenings was one thing, but I wasn't sure I could cope
with wearing such a revealing uniform and being hit
on by customers all the time. The girls soon talked
me round, they pointed out that the dress I was
wearing that night was pretty skimpy, plus I really
needed to get some paid work. Eventually I agreed
with the supervisor that I would try out the following
night and see how I did. The girls were thrilled with
the news and the next day took me out for a manicure
and a haircut. My hair was quite long for a guy, but
they got the hairdresser to give me a very cute bob. I
wasn't too worried at the time as I figured it meant I
wouldn't have to wear a wig while working. It was
only later that I realized I would now have to stay as a
girl all the time as there was no way I could comb my
hair into a more masculine style. They also took me
shopping and I got a few outfits of my own so I
wouldn't have to keep borrowing from them.
That night as I dressed in my sexy uniform for the
first time, my heart was in my mouth. I really didn't
know what I was letting myself in for. I loved the
way the uniform made me feel so feminine and
vulnerable but I didn't know how I would deal with
the attention it would attract. The girls encouraged
me by telling me I looked fantastic, but I made a lot of
silly mistakes with my first few customers. There
were a lot of hands on my ass as I took orders, but I
learnt to brush them away. By the end of the night, I
was exhausted (I wasn't used to wearing stilettos for
that long), but I had to admit I wanted to do it again.
The supervisor agreed, and I signed up for the next
ten days.
It was really strange going back to the hotel wearing a
dress but nobody seemed to realize I was a guy. I
soon got used to sleeping till noon and working at
the club until the early hours, and as the end of the
first week approached, I realized how much I would
miss it. That's when Ramon walked in (I've changed
his name). Ramon was a tall, good-looking Arab who
already knew most of the other girls. I couldn't take
my eyes off him and he spent most of the night
chatting with me. It turned out he was a
businessman. When I asked Caroline about him, she
just laughed and told me he had been out with some
of the girls and was a 'bit kinky'. He was obviously
interested in me though; when I went back over, he
asked me if I would have a drink with him after my
shift finished. I was thrilled, I rushed through the rest
of my work and all the girls were giggling and teasing
me about how I'd pulled big time. I'd come in that
day in jeans and a sweatshirt, so I borrowed a little
black cocktail dress from Suzie and went out for my
drink with Ramon.
After about 5 minutes, I think I would have done
anything he asked. I thought his stories were
fascinating and I was totally captivated. We danced
for a bit and then he leaned over and whispered that
his car was outside and did I want to come back to his
house? Needless to say it didn't take much to
persuade me. I got a real shock when I saw his car -
it was a huge limo with a bodyguard in the front. We
settled into the back and he showed me the bar. It
seems really strange to say, but until that point, I had
never had a homosexual thought in my life. After a
few drinks however I found myself kissing another
guy for the first time ever and pretty soon Ramon
guided my head down onto his cock and I found
myself giving my first blowjob. Thinking back, it felt
like a natural step. With everything that had
happened to me recently, I felt totally comfortable in
my role as the girl doing everything possible to please
her man. I even managed to swallow!
When we arrived at his house, I got my second shock
of the night. It was a large mansion set in its own
grounds with guards on the gate. We stumbled
through the front door with Ramon's hands all over
me. He soon found the zip on my dress and by the
time we got to his bedroom I was down to my
corset, knickers, stockings and heels. I was having a
really hard time with the buttons on his shirt, the girls
had put false nails on me and I couldn't grip anything.
Soon he was naked and I got my first real look at
Ramon's cock. It was massive, much bigger than mine
and it was rock hard. Then I felt Ramon gently bend
me over, apply a sticky goo to my ass, and very gently
enter me. At first, the pain was unbearable, and I
thought he would split me in half. Then it began to
ease and waves of pleasure overtook me. I could feel
Ramon's balls slapping against my ass as he rode me,
and I tried to control my muscles to give him the
tightest possible ride. His orgasm tipped me over the
edge and we both came together, with him filling me
up. Afterwards I was lying on the bed exhausted and
Ramon got up to go to the bathroom. When he came
back he was carrying something, but I was to weak to
turn my head and see what it was. It was then that I
got my third surprise of the night and found out why
Caroline had called him kinky. Ramon lifted me onto
his lap and began to spank me. I was too shocked to
struggle, but after half a dozen really hard slaps I
began to scream. He didn't stop until I'd taken at least
20, by which time I was sobbing quietly. Ramon then
lifted up the object he had just collected and fitted it
around my waist. As he clicked the lock shut, I
realized it was a chastity belt.
I was so shocked, I just looked at him with my mouth
open for 10 seconds. Eventually Ramon laughed and
reached over to stroke my hair. He told me I was
his little sissy whore now and I would have to wear
the chastity belt to make sure I only thought sweet,
girlish thoughts and didn't stray from my man. I
was amazed, but more turned on than I'd ever been
that this man had taken control of me in such an
intimate way. Suddenly I winced as the belt did its
work, Ramon just laughed again and told me I'd get
used to it. If I pleased him, he would allow me short
periods of relief. As I got dressed again I tugged at
the leather band of the chastity belt but couldn't shift
it. Eventually Ramon got his driver to take me back to
the hotel. As I sat in the back I wriggled around
trying to get comfortable and coming to terms with
the fact that Ramon now controlled my sexual
pleasure.
When I woke up the next day I thought it was all a
dream at first - until I felt the metal tube cut off my
erection. The girls crowded round me when I
walked in the club, demanding to know what had
happened. Shyly I lifted my skirt to show them. Of
course they all thought it was hilarious. Ramon
showed up early that night and was very attentive.
The chastity belt was really frustrating; I was
desperate for relief, and probably would have done
anything he asked. He added to my frustration by
teasing me by waving the key in front of me. We
went out again after my shift; he did take the chastity
belt off for a short period like he promised, but only
after I had spent half an hour on my knees giving him
another blowjob.
The next night was my last night at the club and
Ramon said he would let me go out with the girls
afterwards, but he wanted to go to dinner with me
the following night. I got back to my hotel really late
and was woken by a knock on my door at 8:00AM. It
was John (Ramon's driver). He handed me two
packages and told me I was to be ready for dinner at
7:00PM wearing exactly what was in the bags. After
he had gone I had a look and found a beautiful white
full-length evening dress with spaghetti straps, low
front and a straight skirt with a split up one side,
almost to the waist. I would have to be careful
wearing that or everyone would see my chastity belt!
There was also a corset, knickers, stockings and five
inch spike heels. I spent most of the day getting
ready for my date with Ramon, starting with a long
luxurious bubble bath and another shave to make sure
my body was totally free of hair. Eventually I
squeezed into the corset and zipped the dress up. John
knocked on my door again at 7:00PM sharp, and I
stood up to go. Even though he had hardly
acknowledged my existence before, he smiled broadly
when he saw me and told me I 'looked
great'. I was feeling a little exposed, so I picked up a
wrap. John immediately took it out of my hands
telling me that Ramon's instructions had been
very specific. I was to wear only the clothes I had
been given.
Needless to say there were lots of people staring at me
as I walked out of the hotel. I even attracted a wolf
whistle. John just smiled and steered me to the car.
Ramon was already at the restaurant and stood up to
greet me. I could feel his eyes all over me, and
blushed deep red. Dinner was lovely, Ramon
kept telling me how beautiful I looked. Towards the
end he told me he had a surprise, but first he wanted
to test my devotion. He told me to go to the Ladies,
remove my knickers and hand them to him. I was so
much under his spell by then, I just did as I was told
without question. I felt a little thrill as I realized
Ramon had demonstrated his complete mastery over
me again.
When I sat down Ramon told me his surprise. As I
was now unemployed, he wanted me to
move in to his house. He would pay me pocket money
and in return I would be at his side whenever he
wanted. He told me that while we had been eating,
his staff had packed all my things and settled the
hotel bill. He gave no thought to the
possibility that I might not agree - I was coming home
with him that night. As we drove back to the house, I
reflected that a few short weeks ago I had been
just another guy. Now I was dressed as a beautiful
woman being driven to the house of this man who had
just taken ownership of me, as though my wishes did
not matter. This really was my fantasy come true, I
was so turned on by the fact, that I didn't know where
this was heading and had no control over events.
Ramon was obviously turned on as well; we had some
of our best sex ever that night. We started in the
kitchen and I think I was screwed in most rooms in
the house. I must have kept the staff awake into the
small hours with my screams of ecstasy.
Ramon spent most of his time away on business trips
so I found I was left alone for three or four days and
then with him constantly for 24 hours. He had
sent someone out shopping to make sure I had a fully
stocked wardrobe, although I noticed I didn't have any
trousers or shoes without heels. It was also clear
there was no way Ramon's staff would let me leave
the compound; everything would be brought in for
me. One day, about a week later, Caroline and Suzie
came to visit me. Ramon had put me on a strict diet
and they were amazed at how much weight I had lost.
We were sitting around laughing and chatting when
Ramon rang to tell me he would be home in a few
hours.
While he was away I got to dress in more comfortable
clothes but he liked me to dress as sexy as possible
when he was around. This time he instructed me to
go and remove the loose summer dress I had on and
change into a white blouse, a very short and tight
black leather miniskirt, sheer stockings and four inch
strappy sandals. Of course the girls teased me and
told me I was a good little wife doing what my
husband told me. I didn't care - the chastity belt was
driving me wild with frustration by then. If this
was what it took to please Ramon and get him to
unlock me for a few hours then it was worth it. When
he arrived, he pulled me to him and kissed me. He
was delighted to see the girls there; he immediately
started teasing me by patting his crotch and telling me
how he had a big present for me. The girls thought all
this was hilarious, especially when Ramon got me to
serve all three of them during dinner later. As usual,
on the nights when he got back from one of his trips, I
received many loads of his precious cum in both ends
of my body that night.
Perhaps the strangest thing that happened was a few
weeks later, just before I was due to come back to the
UK. As you may have realized by now, Ramon had a
healthy interest in BDSM, and he belonged to a local
Dominants club. Most of the members exercised
varying degrees of control over their slaves, and
one woman, with a house in the hills outside the city,
had decided to marry her live in, feminized, sissy
maid. Ramon had volunteered me as one of the
bridesmaids. As I got into my dress on the day of the
wedding, I had some of my worst jitters ever. I was
wearing a full-length, cream silk dress with a tight
bodice and straight skirt. My hair was a lot longer by
now and Ramon arranged for a hairdresser to come in
that morning. By the time he had finished, my hair
was teased into a very elaborate arrangement and
decorated with flowers.
When we got to the house, I found the other two
bridesmaids and bride were already there. We were
put away in a room on our own while the guests got
drunk waiting for the ceremony to start. They told me
all sorts of stories about the way their Masters treated
them and I realized the humiliations Ramon put me
through were mild by comparison. Jane (the bride)
had even been made to serve dinner in a Victorian
Maid's uniform for two of her ex-girlfriends who
her Mistress had tracked down. Throughout the meal,
she had been forbidden from talking unless it was in
French. One of the other girls had been made to walk
into a bar and offer a blowjob to the first guy to join
her outside. They asked me about Ramon, and told
me they were very jealous my Master was so good
looking. I was about to object and tell them Ramon
was not my Master when I realized how silly that was.
After all, Ramon had subjected me to, it was clear that
he owned me body and soul. I had never disagreed or
objected to a single order he had given me and I
couldn't see myself starting now. In a few short
weeks, he had turned me into an obedient, feminine
creature whose only goal was to make him happy.
It was a lovely sunny day, and the ceremony was out
in the garden. The only problem with this was that
our heels kept sinking into the lawn. Of course
June had to promise to obey her Mistress and was
made to kneel while a collar was locked around her
neck. After the ceremony, a magician had been
booked to entertain the guests. The bridesmaids had
to serve drinks while Jane was made to change into a
gold lame bikini and heels and act as the assistant
to the magician. The poor girl was sawed in two,
made to disappear, and shut into a box which the
magician then stuck swords into. At the end of the
final trick, Jane found herself in handcuffs, chained to
a ring in the ground, without the top half of her
bikini. She was just left there for 30 minutes while all
the guests crowded around feeling her up.
After we had served dinner, Jane's Mistress called the
bridesmaids into a big bedroom at the top of the
house. On the bed were three gold, white, and
red cotton cheerleaders dresses which we were
ordered to change into. We then put on track shoes
and braided each other's hair into pigtails. Mistress
produced some leg irons and chained the three of us
together. She then locked collars around our necks.
Each of the collars was attached to the others with
a short length of chain. Once we were securely
fastened Mistress led us back downstairs as we
shuffled behind her. She stopped outside one of the
dining rooms and knocked. When we entered we saw
our owners sitting around a large table covered with a
white tablecloth playing cards. We were ordered
to get under the table and give our owners a blowjob.
We must have been under there for hours! The
women all thought this was hilarious and clapped
every time we managed to bring one of them to
orgasm.
Shortly afterwards, it was time for me to go home.
Ramon never suggested we had a long-term future
together, he always told me he would let me go when
the time came. Even so, he was determined to keep
me under control for as long as possible. I was
allowed to get a hair cut and dress in T-shirt, jeans,
trainers, and jacket for the journey to the airport but
he made me wear a corset, knickers and suspenders
underneath and would not release me from my
chastity belt. He also made sure all my clothes were
packed in the suitcase so I would not be able to
change during the flight. When the time came to say
goodbye, he kissed me on the lips in front of all the
other passengers and handed me a key. Then he
walked off.
I ended up undressing in the toilet on the aircraft and
leaving my lingerie in the rubbish bin. Luckily the
key he gave me was for the chastity belt so I was
finally able to remove that too. I've often wondered
what the cleaners must have thought when they found
all that sexy underwear and a chastity belt when they
were cleaning the plane!
I hope everyone enjoyed the story; it is my first effort.
I welcome any comments or suggestions.
---------------------------------------------
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