Master s Sissy Slave Chapter 5 Humiliation
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Beyond Humiliation - Chapter 1 - Holiday Planning free porn video
BEYOND HUMILIATION
Chapter 1 - Holiday Planning
Back in November 2012 I wrote a story called "How Humiliating". It told
how Stephen, an occasional and secret cross-dresser, was caught out by
his wife Sandra and forced, through a series of humiliating experiences,
to confront and come to terms with his obsession. Although angry with
Stephen for him not being open and honest about his desires, Sandra
found the whole idea of cross-dressing strangely exciting and whilst she
quite enjoyed watching him squirm with embarrassment as his, previously
private habits, were gradually brought out in public, she still loved
him and took care that her demands never actually caused him pain or
harm. By the end of the story Stephen had come out to his friends and
neighbours without forfeiting too much of their goodwill and, as
"Stephanie", (s)he and Sandra were entering a new and exciting stage in
their marriage.
It had always been my intention to revisit these characters to see how
their lives developed, but until now hadn't come up with an idea that
inspired me. Now I have! I hope you enjoy this next phase of their
adventures and would encourage you to read the earlier story first
xxxxxxxxxxxxxxxxxxxxxxxxxxxxx
'Stephanie' was definitely having a good summer; lots of tennis and
golf; barbeques at friends' houses; drinks parties in lovely gardens,
everything an attractive young woman could wish for. All these different
activities, of course, required an extensive and stylish wardrobe, so
Stephanie also had fun making regular shopping excursions into
Cheltenham with her best girlfriend Sandra.
All this sounds perfect, and it is, except for one thing. You see
'Stephanie' isn't actually a woman at all; she is me, a 30 year old
Marketing Manager called Stephen, and Sandra is my wife!
Now that my cross-dressing is out in the open and accepted not only by
Sandra but also our friends and neighbours, I am able to attend these
functions in either male or female mode, depending on how the mood takes
me or whether it is 'Stephen' or 'Stephanie' who has received the
invitation! I suppose on balance, I spend about a third of my time as
Stephanie and two-thirds as Stephen. Recently, however, I have noticed
that I am spending more time in the female role - particularly at home
with Sandra.
Sandra is totally cool about my dressing. In fact, she says that it has
added spice to our marriage that had been in danger of getting into a
bit of a rut. Certainly the frequency and passion of our lovemaking has
gone up several gears!
It was mid-September and you could certainly tell summer was coming to
an end. Leaves were turning on the trees and there was a cool nip in the
air in the evenings. It looked as though our time socialising outdoors
was coming to a close for the year. Although we had had a lovely, full
summer of parties and activities, it had also been an unusually busy
time for me at work. Generally I could count on the work dropping off a
bit during August, but this year it had just got busier and busier. This
was because we had successfully bid for a large new contract and I had
had to get my team up and running on the project ready for an autumn
launch.
They say 'all work and no play make Jack a dull boy'; my trouble was I
had had too much work and too much play! I was exhausted and Sandra was
concerned that I might have been overdoing things. "Can't you take some
time off when this project goes live?" she enquired anxiously. "Only if
you don't get a real break soon I am worried you will become ill." I had
to confess that I felt very much in need of a holiday. "I should be able
to get a decent amount of time off in November" I told her, "but, of
course, that is just the wrong time of year for a holiday." "Oh I don't
know" Sandra mussed. "We haven't had a proper holiday for a couple of
years. Why don't we go mad and splash some money on an up-market cruise.
We could both do with a spot of sun and lots of pampering. Shall I start
researching what might be available?" This sounded a lovely idea and I
happily agreed to Sandra looking at possibilities.
Of course, inevitably, as soon as we had made this decision my workload
shot up again. This time, however, I had something to look forward to. I
went to see my boss and told him that I would need time off once this
project was completed. "I agree Steve" he said. "It isn't only Sandra
who has been worrying about your health; I have been concerned too. But,
as you know, your input has been vital to the success of this project.
Still we can now see the light at the end of the tunnel. Why don't you
take November and December off and come back refreshed and ready for
another challenge in the New Year." This was very generous and much more
than I had expected. I had hoped to be able to take three weeks off and
here I was being offered two months! My boss then put the icing on the
cake by saying; "I shouldn't really be telling you this just yet, so
keep it under your hat. Your work on getting and implementing this new
business hasn't gone unnoticed by the Board. In the New Year you are in
for a very nice bonus and a promotion. So you can afford to push the
boat out a bit now!"
This was amazing news and I could hardly wait to get home to tell
Sandra. She squealed with delight; "It is only what you deserve darling;
now I can really get serious about finding us the holiday of a
lifetime!"
A few days later Sandra was in a fever of excitement when I got in from
work. "I've done it!" she announced with glee and pride. "Not only have
I found us the most fabulous holiday, I have gone and booked it!" I too
was very excited and quickly poured us each a large glass of wine as
Sandra showed me all the maps and brochures she had been working with.
"I couldn't find anything in the brochures that seemed 'just us'" she
told me, "So in the end I rang a specialist Travel Consultant and asked
his advice. Between us we have put together the most fabulous trip." She
then went on to explain that we would be visiting South-East Asia and
the islands running down towards Australia. "Just imagine" she enthused,
"we will be seeing the sights of Thailand, Cambodia, Vietnam, and Loas,
and as well as taking a cruise around the South China Sea. We will visit
Borneo and Bali; Sumatra; and Singapore as well as lots of other places.
We will see Orang-utans; temples - I can't wait to see Angkor Wat at
dawn! Oh it will be wonderful!"
I took Sandra in my arms and kissed and praised her for what she had
achieved. When we married we didn't have much money, so our honeymoon,
whilst memorable, hadn't been anything like as exotic as this holiday
promised to be. "It sounds wonderful; darling" I enthused. "Is their
anything you want me to do to help set it up?" "No" she replied "this is
my project and I want it to be a surprise for you." And that is how it
was; I was told nothing more until a few days before were due to set
off.
After dinner one evening, about one week before we were due to set off
on our much anticipated holiday, Sandra asked me pour us both a drink
and join her on the sofa. "Now I don't intend to tell you too much about
our forthcoming holiday; I want it to be a surprise for you" she
started, "but there are few things we need to sort out before we set off
so that you can enjoy the full benefit of what I have planned for us."
This was intriguing and I sat forward, eager to hear what she had to
say.
"We both know how important your cross-dressing is to you" Sandra
continued, "and, I have to confess to me also. I find it very erotic
seeing the feminine side of my husband and just adore the way our
lovemaking has taken on a new lease of life. In fact I am becoming quite
aroused just talking about it! I know you enjoyed spending time as
'Stephanie' during the early part of the summer, but this last month or
so, whilst you have been so excessive busy at the office, your dressing
time has dropped right off and I am afraid your frustrations are
beginning to show. You have been much shorter with me recently and you
are always so serious. I want my best girlfriend back please!" I
hastened to start to apologise and explain, but Sandra cut me short;
"Don't take what I am saying the wrong way" she assured me, "I'm not
complaining or angry or anything, I just want you to be happy and this
holiday gives us the opportunity to make a re-start for Stephanie."
"But I can't be 'Stephanie' on holiday" I expostulated. "For a start we
are going on a cruise for part of the time. What will our fellow
passengers think when someone they know as 'Steve' suddenly turns up in
a dress"! Sandra sat calmly through my diatribe; "For a start it doesn't
matter what others think and, anyway, why are you so sure they will know
you as 'Steve'? What if 'Stephanie' was to be the only person they
meet?" This last remark really caused my jaw to drop. "Are you seriously
suggesting that I spend the entire holiday as 'Stephanie'?" I enquired,
with a tremor in my voice. The idea was at one and the same time
terrifying and strangely exciting.
"That was my original idea" Sandra confessed; "Then I realised that
there might be occasions when you would need to appear as 'Stephen' -
going through immigration in some of the more puritanical countries for
example. But yes, I do think we should plan for your being in female
mode for most of the time." We paused and Sandra poured us another round
of drinks whilst I tried to digest this bombshell.
I had to acknowledge that I was missing opportunities to dress and
couldn't contest Sandra's assertion that I was becoming a bit bad
tempered. But the risks involved with being Stephanie for several weeks
- and in close proximity to the same people for days at a time. This was
quite a challenging prospect.
Sandra returned with our drinks. She could see I was still struggling.
"Look darling" she said as she put the drinks on the table and sat down.
"Just trust me. You know I would never do anything to harm you, but you
have to admit that I was right to set you all those humiliating tasks to
get you to understand and accept that you had a real and genuine need to
cross-dress." I accepted the truth in what Sandra was saying. Whilst, at
the time, I had been terrified of being humiliated in public, in
practice most of the challenges she had set me had passed off smoothly
until, finally, I had found the courage to come out publicly at a party
and tell all our friends and neighbours about my dual personality. Most
of them remained our friends to the point where I was now able to
interact with them in either the male or female role.
"I don't know, my love" I responded cautiously. "Of course I trust you,
but what you are proposing now is a whole new ball game!" "Yes, but
think how proud you will be when you carry it off" Sandra responded
quickly.
We continued talking for most of the evening until, finally, I had to
succumb to the force of her arguments - and her blandishments - and
agree to give it a try. "But you promise me I can take some male clothes
with me so that if things get out of hand I can revert to being
'Stephen'?" I insisted. "I have already promised you that" Sandra
murmured, kissing me gently on the cheek. "I realise there will be some
situations when you won't have any choice but to be 'Stephen'. However,
I will be the one to decide when those occasions occur. At all other
times you will dress in line with my advice. Agreed?" We shook hands on
the deal and I hurriedly took Sandra upstairs to our bedroom. Our
conversation and the prospect of me having to face all sorts of new
challenges had made us both randy. It was quite some time before we got
to sleep!
A couple of days later, the Saturday before we were due to go away;
Sandra announced that she had booked us session at the beauty salon we
both used. "Your body hair has started to grow back since you stopped
dressing regularly" she said with a moue of distaste, "and it is going
to have to go. Not only is it not in keeping with your feminine persona,
but I am not going to share my bed with a prickly man all the time we
are on holiday!" So we had a lovely day - (once the waxing was over!) -
being pampered and beautified. I left the salon having had both a
manicure and pedicure and with my toes varnished a deep burgundy colour,
whilst my fingernails were a pretty pink.
The big excitement, however, was getting my hair styled. I had
deliberately allowed it to grow quite long and my stylist announced that
it was now of a length where she could do something with it. What she
did was to enrich my normally mousey hair colour to a dirty blonde, with
subtle, brighter highlights. She actually cut my hair quite short, but
in such a way that if I brushed and set it one way it looked very
feminine and modern; but if I washed out the setting lotion and brushed
my hair down, my 'look', whilst a bit androgynous, could still pass for
a man's cut. I was delighted with what she had achieved and tipped her
accordingly!
I had deliberately started my leave a few days before we were due to
depart so that I could sort out my packing and appearance in peace and
quite and without being under any pressure. Hence no one at work would
see me in my new hairstyle and as for the neighbours; they were used to
me appearing feminine. In fact several of our lady friends complimented
me on my new cut and colour.
Having sorted out my appearance, the next challenge was to decide which
clothes to pack. Sandra relented on her pledge to keep details of our
holiday secret from me just so far as to tell me that we would be
cruising for the first three weeks. "You are pretty much worn out as a
result of all the stress and strain at work and time relaxing in the sun
will set you up for the more strenuous part of the holiday touring
through South East Asia" she explained. "I suggest you pack three cases;
one for the cruise - lots of pretty sun-dresses and at least four smart
cocktail and evening frocks. After all a girl can't be seen wearing the
same thing too often! I have ordered you a couple of special swimsuits
that are designed so as to hold your breast forms out of sight and give
you the appearance of a bosom even when you are in the pool. Your second
case will be more for our overland travels and should contain cotton
skirts and blouses, together with lightweight slacks and Capri pants.
You will also need to find a pair of sensible shoes suitable for
sightseeing in rough terrain. Your final case - which can be a small one
- will be for the few male clothes you need to take. I will choose what
is appropriate." "But if I take three cases, what about your things?" I
enquired, "Surely no airline will let us take six pieces of luggage."
"Not if we were flying Economy" Sandra replied with a laugh, "but this
time you and I are treating ourselves and flying Business Class, so we
have plenty of baggage allowance for all eventualities."
Now even though I was nervous about the risk of being humiliated on this
holiday, one thing I have learned to enjoy since discovering
'Stephanie', is shopping! So I eagerly accepted Sandra's suggestion that
we spend the following day seeking out any items we would need that
didn't already hang in our respective wardrobes. We spent the rest of
that day, and well into the evening, going through both our wardrobes
picking out; trying on; discarding; and selecting until we each had a
substantial heap of clothes piled on our bed. We then went through a
second phase of selection until we had the piles down to a manageable
size. I found I was quite well off for party frocks; I would just need
to buy one full-length evening dress for any very smart function. I also
had a reasonable assortment of casual wear; what I would need to look
for were trousers and tops suitable for sightseeing in the tropics.
The following morning we set off on our shopping expedition just as soon
as the shops opened. In the event we managed to get out 'tropical gear'
fairly quickly. I ended up with some lovely cotton and linen blouses,
two pairs of linen trousers - one in a natural bleached colour and the
other a darkish brown. Sandra then insisted that I buy a pair of
fabulous turquoise Capri pants that she said would look adorable on me.
When I tried them on I too fell in love with them. (I had no trouble
trying on women's clothing because, as was now my custom, I was in
female mode anyway.)
Sandra purchased similar safari garments for herself, but in slightly
different colour combinations and styles so that it wouldn't look as
though we were trying to dress alike. We each bought a pair of stout
leather and canvas trainers. Mine were white with green trim, whilst
Sandra's were white and blue.
Our next port of call was to find me some sandals - (Sandra was already
well supplied with appropriate footwear). I ended up with a pair of pink
flip-flops; cream canvas wedgies with a rope trim; and two pairs of
strappy, heeled sandals.
Then came the difficult bit; evening wear! We spent hours traipsing from
one shop to another - (I loved every minute of it); trying on long
dresses; short dresses; even a few skimpy dresses - Sandra quickly
vetoed these! "We don't want to appear to be a couple of man-hunting
tramps" she giggled, "even if we are!" We both laughed at this sally. If
I had only known then what was going through Sandra's mind!
Eventually we both found dresses we adored. Sandra's was pale blue with
a fitted top with little straps that revealed a fair amount of her sweet
breasts; and a flowing skirt that just fell to the floor. Mine was a
little more modest as I couldn't afford to display my bosom quite as
openly! It was still delightful, with a scooped neckline with wider
straps and loose fitting bodice. The skirt fell away from underneath my
bosom to the floor. It was made of a forest green silk and looked
fabulous. Naturally these dresses cost considerably more than we had
talked about spending but there were no arguments; we both knew these
dresses were 'just us'.
Back home we modeled our new dresses one more time before packing them
away in long carrying bags. In addition to my evening gown I packed a
classic 'little black dress' suitable for cocktail parties, and a rather
more flamboyant one in royal-blue satin with a net underskirt that
swirled delightfully. I also took another of my favourite evening
outfits; a pair of black, silky palazzo pants, teamed with a black
velvet camisole and an elaborately beaded and sequined lace jacket.
By the time I had packed all my 'essential' clothes, accessories; and
accoutrements away, both my 'girly' suitcases were bulging. Sandra's
were if anything even fuller. As she had indicated, I wasn't allowed to
see what male clothing Sandra had packed for me in the little case that
looked rather lost amongst our other luggage.
Well, if I had any doubts about going on holiday as 'Stephanie', it was
a bit late to express them now. We had spent a great deal of money to
ensure that our trip was "the holiday of a lifetime" - not to mention
all the new clothes and accessories! Sandra would not be at all happy if
I called it off now. No, there was nothing for it; I would just have to
take a deep breath; go for it; and hope that my humiliation wouldn't be
too severe!
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