Lucky StiffChapter 29 Romantic Date
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A Lucky Date free porn video
A LUCKY DATE
PROLOGUE
Amanda looked in the mirror to check her hair and makeup. Although a
fiftysomething woman, she looked at least 10 years younger. With her
dark blonde hair cascading down to her shoulders, she had an easy beauty
that others immediately responded to. Although flawless as always, she
checked her makeup for one last time, touching up her deep red lipstick
before looking deeply into the reflection of her own eyes. In an
instant, she saw the inner happiness which she now felt; the last two
years had been unbelievable for Amanda and all of the unhappiness she had
felt in her life was now a dim and distant memory.
As she made the final preparations for the most important journey of her
life, she drifted off into a daydream thinking about everything that had
happened to get her to where she was now...
CHAPTER 1 - EARLY DAYS
Michael was a child of the 1960s; no brothers or sisters but loving
parents who doted on him. He did all the things boys normally do but,
equally, enjoyed his own company and loved to read. He liked the girls
at school, especially the pretty ones, but even at his young age, he felt
an attraction to them. By the time he was a teenager, though, the girls
were a dim and distant memory - sent to an all boys school, there was
little opportunity to talk to girls and he could only watch from afar,
marvelling at them as they started to grow into young women.
When Michael was asleep, he sometimes dreamt that he was a girl and, as
he grew into a teenager, increasingly felt the frustration of being
unable to be a part of their world. About this time, two things happened
that sealed his fate; the first was when his mother told him that she had
read a book by someone who had had a "sex change" and the second was
finding a pair of his mother's tights and trying them on while she was
out of the house. Both had a profound effect - could men really be
turned into women? Why did he have such strong sexual feelings from
women's clothing?
Still not fully grown, Michael soon found out that his mother's clothes &
shoes fit him and so would take the opportunity when the house was empty
to fully dress. He loved the sensation of the soft clothing against his
immature skin and wished with all his heart that he could have been born
a girl. However, the feeling of guilt about what he was doing (and what
he was feeling as a result) and the dread of being found out was
overpowering and increased opportunities to mix with girls cooled his
transgender desires for the time being.
Moving on a few years and with a good job, Michael was living alone and
the urges started to return. He realised that he could buy clothing from
supermarkets without having to confront sales assistants and so started
the cycles of buy, wear, purge that would become a repeat feature of his
life. Although Michael lacked the success with girls that many of his
friends enjoyed, he did find that when he was in a relationship, his
urges went away and, as many others have mistakenly believed, thought
that marriage would cure him.
Sure enough, when he met and married his wife, he enjoyed seeing her
wearing the type of clothing he would once have craved for himself and
the desire to dress evaporated.
Or so he thought.
CHAPTER 2 - A LOVE REKINDLED
Marriage is a funny thing. After the initial flush of love and passion,
things settle down into a routine. People grow older and whereas short
skirts and four inch heels were once mandatory dress for an evening out,
they now meant cold legs and aching feet. Children increase the burdens
tenfold and, eventually, Michael realised that the girl he married was
gone forever, replaced by a middle aged woman with a wardrobe to match.
It was then that the "what ifs" started. What if he bought a pair of
high heels, just to see what they felt like? What if he bought an outfit
to go with the shoes? What if he bought a wig to give him a feminine
hairstyle? What if he bought makeup to see how good he could look as a
woman?
There was only one way to find out and, being home a lot while his wife
was at work, he had plenty of time to experiment. What he found out
surprised him; the sexual urges he once felt from dressing in women's
clothes had gone to be replaced with feelings of elation and calm as if
he had finally become the person he should always have been. He knew he
could never pass as a woman but that didn't matter; as long as he had
long hair and wore skirts, dresses and high heels, he was, for that
moment, a true woman and that's all that mattered to him. From time to
time, guilt would get the better of him and he would purge everything,
only to grieve for its loss and replace it all.
All he needed to do was to make sure everything was packed away and
hidden when he had finished. And that's where things started to go
wrong.
One day, as he prepared for a dressing session, he realised that his
makeup bag was not in the case. He looked everywhere but couldn't find
it and realised that he had to confess all to his wife in case she found
it. He prepared himself and, when she got home that evening, sat her
down and confessed everything. Tears and upset followed and Michael
realised that he had done something very bad; dressing as a woman was bad
enough in his wife's eyes but far worse was the deception in not telling
her about his feelings sooner. Over the coming weeks, his wife tried
very hard to understand but, eventually felt that enough was enough and
gave him an ultimatum - stop dressing or end the marriage.
Michael chose to preserve the family and purged his clothes for what he
was sure was the final time. However, as almost everyone in his position
finds out, the urges never disappear and slowly but surely, he slipped
back into his old ways believing that the hiding place he had found would
never be discovered.
It was.
And with that, five words blew his life apart.
"That's it, then. We're finished."
As he moved out of the family home into a dingy one bedroomed flat in a
not very nice part of town, Michael really wondered whether it had all
been worth it. Was seeing his legs a pair of high heels and stockings
really more important than seeing his children? Had he really lost his
house for the sake of a wig? Was his social life really only worth a
lipstick and eyeliner? Ironically, the realisation of what he had done
drove him to bundle his collection of female clothes, shoes & makeup up
and put the whole lot out with the rubbish. It would never give him back
what he had lost but, in a strange sort of way, he felt it was a price he
had to pay.
He was now completely alone with only his memories for company. Had his
life really come to this? Would things ever get any better?
And then he met Sue.
CHAPTER 3 - THE DATE, AND A SURPRISE
As he sat alone in his flat as he had done more or less every night since
his marriage broke down, Michael contemplated his situation. Ironically,
he'd not felt like crossdressing much since the breakup - his feelings of
guilt at breaking up his family had put paid to that. So there was
really nothing else to do other than to sit there, on his own and feel
sorry for himself. Finally, he thought that enough was enough and put
his coat and shoes on to go to the local convenience store for some beer
and, if he was lucky, a half decent DVD to watch.
Entering the store, he exchanged his usual pleasantries with the female
security guard, quickly picked up and paid for his beer and DVD and
walked towards the exit.
"Not out on the town tonight?" asked the security guard.
"Sadly, not."
"Nowhere to go on a Friday night?" she asked.
"More a case of no-one to go with, I'm afraid.
Now the security guard, although female, was the exact opposite of
Michael's taste in women - he liked long flowing locks, her hair was tied
back in a pony tail; he liked women to be made up, her face was devoid of
all cosmetics; he liked women in skirts and dresses, her security guard
uniform of thick navy sweater and trousers hardly fit the bill and her
sensible flat lace ups were anything but the stilettos Michael liked.
But there was something about her, a natural beauty that Michael all of a
sudden found irresistable.
"I don't suppose..." he started.
At that moment, a commotion started in the shop.
"Got to go" said the security guard who then reached into her pocket
pulled out a card, scribbled a quick note and handed it to Michael. With
that she was gone.
Michael left the shop and looked at the card. On it was written a phone
number and then the guard had signed it "Sue x."
Nichael walked home in a bit of a daze. Sue definitiely did not seem to
be his type and yet his heart fluttered for reasons he could just not
work out. Later that evening, he called her and after a short
conversation, they agreed to meet the following evening for a meal.
The next day was Saturday and Michael went about his normal routine -
shopping, washing & ironing. By the afternoon, he was cooling about the
prospect of his date and almost called Sue to call it off. However,
having nothing else to do, he got ready and went to the restaurant.
He arrived early, took his seat and ordered a bottle of wine while he
waited.
"Hello Michael"
Michael looked up, slightly startled to see Sue standing by him. But not
the Sue he remembered. This Sue was wearing a black low cut dress and
shoes with four inch stiletto heels. Her makeup was perfect and her hair
cascaded down onto her shoulders.
"You... you look amazing," exclaimed Michael, all of a sudden feeling
that his open necked shirt was possibly not entirely appropriate.
"Well thank you kind sir," replied Sue with a wry smile.
And with that, Michael jumped up, helped Sue to her seat and settled down
for what was undoubtedly the date he was not expecting.
After probably the most enjoyable meal Michael had ever had and with the
restaurant emptying, he helped Sue with her coat and asked if he could
walk her home.
"OK, I'll trust you to be good," she teased, "it's not far."
Linking arms, they walked the quarter mile or so back to Sue's flat.
"Thank you for a perfect evening," said Michael.
"No, it's me who should be thanking you" replied Sue "would you like to
come in for a coffee?"
They entered Sue's flat, Michael took a seat in the lounge while Sue made
the coffee. He looked around the room; nothing out of the ordinary apart
from a single photograph of a rather overweight, slightly dischevilled
looking man immediately above a glamour portrait of Sue. Studying the
pictures, Michael could see a slight facial resemblance between the two.
"Your brother?" asked Michael as Sue brought the coffees in.
The question seemed to knock Sue off guard. She took a seat next to
Michael on the sofa looked down for a moment then looked him straight in
the eye and said
"No, he's not my brother. It's me. I'm transsexual."
"You're joking. How could someone like him become you?"
"Dieting, hormones and a very clever surgeon" replied Sue who then
somewhat enigmatically added "but I have a feeling that you won't have a
problem with it"
"And what makes you think that?"
Sue put her finger over Michaels mouth. "Shhhh...no more questions for
now. But am I right?"
She took her finger away and looked straight at Michael, her tongue
touching her top lip provocatively and waited for his answer. Michael
looked back at her for a moment and then closed his eyes as he leant
forward and kissed her passionately. He never wanted that kiss to end
but finally, Sue pulled away, stood up and took a hesitant Michael by the
hand.
"Come on, I won't bite and I'm ALL woman," she teased and, with that,
Michael stood up and followed her into the bedroom.
CHAPTER 4 - A CORNER TURNED
After a night of passion, the like of which Michael had never experienced
before, he awoke to see Sue standing over him with a tray of toast and
coffee. She had certainly been right about being all woman and Michael
couldn't help admiring her breasts which her negligee did little to hide.
"So," he started, "what's your story?"
Sue sat down and told Michael the story of her life. How she had always
felt that she had been born the wrong gender but had kept her feelings
secret and lived the life of a male to please her family. How when
things had got too much and she finally decided to transition, her family
completely disowned her and she lost everything - her house, her career,
her friends. How she kept the picture of her former self on display to
remind herself how far she had come. When she had finished, Michael
reached over and kissed her on the cheek.
"Thank you, that must have been really hard for you. But one thing
puzzles me. What made you think that I wouldn't have a problem with
being with a transsexual?"
"You can call it feminine intuition if you want! Alternatively, call it
observation. Firstly, when I date guys, they normally can't take their
eyes off my chest. You, on the other hand kept sneaking furtive glances
at my shoes - this generally means either you work in the fashion
industry or you have an unhealthy interest in ladies feet! Secondly, as
a security guard it's my job to keep a watch on our shop customers. Last
week, you came in and bought a pack of ladies tights. Normally, this
means one of two things - your wife has sent you or they're for you. Now
the fact that you asked me out indicates that you're either single or a
rampant adulterer. I'm going to give you the benefit of the doubt and
assume that you're single but this means the tights were for you which,
in turn means that your interest in my shoes resulted from a similar
interest in cross dressing.
"I may have been buying the tights for an amateur dramatics production
and have an innocent interest in fashion though."
"Were you and do you?"
"Er...no. You're quite right. They were for me and I'm a cross dresser."
This time, Sue reached over and took Michael's hand.
"It's alright, I obviously don't have a problem with this sort of thing.
Why don't you tell me everything?"
And so Michael did, from his first memories, right up to the breakdown of
his marriage. Then he asked Sue, "Why me? Surely men would be lining up
to date a woman as beautiful as you?"
"If I was a genetic woman, then possibly. But I'm not and as soon as I
tell them my past, which I think is only right to do, I don't see them
for dust. If I'm lucky I'm told that I'm a wonderful woman but they
can't handle my past. If I'm unlucky, I just get a torrent of abuse and
threats. After the last particularly nasty experience, I realised that I
need a soul mate, someone who understands me and, after I saw you buy the
tights, I wondered if you were 'the one.'"
When he had finished, Sue asked him, "Now let me ask you something. What
are you feeling right now?"
"I'm feeling on cloud nine because I've just met and spent the night with
the most amazing woman!"
"Is that all?"
"Er...yes," replied Michael unconvincingly.
Sue's smile vanished and a serious expression came over her.
"Look, Michael, you're a sweet guy but if you want this to be anything
more than a one night stand, you have to be completely honest with me. I
value honesty above everything else as, prior to my transition, my whole
life was based on dishonesty and deception. In return, I also expect
honesty from others so I'll ask you just one more time...what do you feel
right now?"
Michael took a deep breath.
"I'm feeling on cloud nine because I've just met and spent the night with
the most amazing woman. Part of me wants to be the strong man, taking
care of her and providing for her. But I'm also tied up in knots. All
of the emotions I used to feel are coming back but I still don't know the
answer to the basic question - what am I? Am I a cross dresser,
transsexual or do I just get turned on by transwomen? When I saw you
last night, I wanted to take you in my arms and hold onto you for ever
but I also saw you as the woman I always imagined myself to be if I went
down the road to transition. Seeing the results of your transition
proved to me that, if I wanted to, I could have a successful transition
too. The problem is that I just don't understand my feelings or know
what I really want." He then chuckled and added "but I do know I'd
really like to try on the shoes you were wearing last night!"
With a giggle, Sue handed him the shoes and the pair of black hold-up
stockings she had also worn the night before.
"Here you are then."
Michael gently pulled on the stockings and then slipped his feet into the
shoes before standing up and admiring his reflection in the mirror.
"Great legs, you were obviously made for this! As for not knowing what
you are, we'd better start trying to find out, hadn't we?"
and with that, Sue took Michael's hand, led him into her spare room and
showed him a wardrobe full of clothes.
"I don't wear these any more as most are too big for me now but I think
they'd be the perfect size for you. You'll find wigs on the top shelf
and, when you're finished, I'll do your makeup for you."
With that, Sue left the room leaving Michael feeling like a child in a
sweet shop! Was something about to go right in his life at last?
About 20 minutes later, Michael emerged in a black dress, black high
heeled stilettos and a dark blonde wig. In fact, his outfit bore more
than a passing resemblence to Sue's the night before. Sue smiled and set
to work on Michael's makeup - about half an hour later, it was done and
she led him to the mirror.
Michael stared at his reflection for several minutes and then a tear ran
down his cheek.
"Thank you so much, this is all I ever wanted. All my life, I've waited
for this moment, to see myself as a beautiful woman, the woman I've often
wished I was. I just feel wonderful."
"It seems a shame to keep you hidden, then," replied Sue, "let's go out."
She looked at Michael and then added, "You'll need to change, though.
You'll never blend in in that outfit on a Sunday morning and those shoes
are designed for sitting down - two minutes of walking in them and you'll
be begging for mercy!"
Sue found Michael some more appropriate clothes for their walk and off
they went arm in arm. All of a sudden, Sue turned to Michael.
"What should I call you. Michael doesn't seem particularly appropriate
now."
"Well, I always imagined being called Amanda so how about that?"
Sue let out a giggle "that's probably not the most appropriate name for
people like us - Amanda - A man duh!" she spelled out "but, if it makes
you feel comfortable, Amanda it is so come on Amanda, let's enjoy the
moment"
And off they went.
CHAPTER 5 - THE DECISION
Over the following months Sue and Michael/Amanda became increasingly
close, finally selling their respective flats and moving in together.
Michael was increasingly spending time as Amanda and becoming ever more
comfortable with his female persona. He had made the effort to lose
weight and was now close to Sue in size. The feeling of calm when he put
on a dress and slipped into a pair of heels was still as strong as ever
and, now that his hair had grown long, he no longer needed to wear a wig.
In fact, he was starting to find that his previous misgivings about
living full time were evaporating and time spent as Michael was now at
best irrelevant and at worst deeply dissatisfying.
Sue sensed this and one Sunday morning, about a year after their first
date together, asked, "So should I still think of you as Michael or is it
just Amanda from now on?"
Michael thought for a moment and replied, "All my life, I've been
fighting this but, after spending the last year with you, I no longer
understand why. I've always wished I was female but never felt that
transition was the right approach. I guess I just felt I had too much to
lose but I can now see that I have so much to gain. I would really like
to say that I want to be Amanda for the rest of my life but I still have
a nagging doubt. What do you think?"
"Michael, I want you to go and put on the clothes you wore to our first
date."
Michael looked crestfallen. "You called me Michael, does this mean..."
Sue placed her finger over Michael's lips, just as she had done on that
first evening.
"Shhh...no questions, just do it for me."
Michael went into the bedroom and changed as instructed. He emerged
about five minutes later and Sue took him by the hand and led him to the
mirror.
"Take a good look. What do you see? Your hair is long and feminine,
your eyebrows are arched and feminine. Your skin is in better condition
than ever, thanks to your moisturisers. Thanks to electrolysis and laser
treatment, you no longer need to shave. These clothes are practically
hanging off you as you've lost so much weight and your whole posture now
looks feminine. Michael is fading away and I think we should let him go
but, before we do..."
Sue turned to face Michael, looked into his eyes and said "goodbye
Michael" before passionately kissing him.
After several minutes, Sue pulled away and said "it's time for Michael to
go now."
Michael understood exactly what Sue meant and disappeared into the
bedroom emerging 20 minutes later fully made up with a hint of perfume
and a loose fitting baggy sweater over a mini skirt. Amanda had arrived
for good!
Sue looked into Amanda's eyes and saw happiness, the like of which she
had never seen before.
"My darling Amanda, I'll be there for you for every step of your journey.
The road ahead will be challenging with much emotional and physical pain
but, together, we'll get you through it. Tomorrow, we'll make an
appointment for you to see the gender therapist who'll be able to assess
you and set you on the path to hormone therapy and advise you on the
surgeries you need. We've got a lot to do to reverse the effects of
several decades of testosterone so let's make a start by helping Michael
move out completely."
And with that, Sue and Amanda embraced in a long and passionate kiss
before the two of them set to work packing Michael's clothes up to donate
to charity.
CHAPTER 6 - CHANGES
Slowly but surely, Amanda's body changed. At first the changes were
almost imperceptable but after a few months, she could tell that her hips
and breasts were developing and her face had taken on a more feminine
look with her cheekbones becoming more prominent. However, for her, the
changes weren't fast enough and so she spent time researching facial
surgeons and finally found one she was comfortable with who could reshape
her face with feminisation surgery and give her the breasts she had
dreamt of. The only problem was he was based in South America but Sue
felt that this was a great excuse for a holiday, even if Amanda would
emerge swathed in bandages looking as if she'd just done 15 rounds with
Mike Tyson!
However, it was one thing putting on makeup and taking pills everyday; it
was a completely different proposition committing to surgery which
included radical reshaping of the bones of her skull, jaw and nose, not
to mention the hairline adjustment, eyebrow lift, face lift and Adam's
apple reduction all of which she knew could cause discomfort for several
weeks. And that was before she factored in surgery on her larynx to
feminise her voice which would mean she would have to remain silent for
several weeks afterwards. In fact, the only things she didn't fear was
the breast augmentation which seemed insignificant in comparison.
However, no-one said that the pursuit of femininity was going to be easy
and so, with Sue by her side, she made the journey.
Coming round from the surgery, she was covered in bandages and dosed up
with painkillers to make life as tolerable as possible. Her surgeon
seemed pleased with is work and certainly, when she had fully come round
from the anaesthetic, she marvelled at the two mounds under her
nightdress top and gently caressed them to ensure that they were truly
part of her. Over the next few days, her bandages were gradually removed
to reveal swelling and bruising but, as these subsided, she started to
see the new her emerging and she liked what she saw. Still, though she
had to remain silent until her vocal chords had fully healed.
A few days later, she was discharged from hospital and joined Sue in her
hotel room which they used as a base to enjoy a few days" holiday and see
the sights. Soon it was time to return home but, before doing so they
had one last appointment at the clinic.
"So, Amanda, do you like what you see now?"
Amanda nodded her approval.
"Why don't you try to answer me?"
"Yes, thank you doctor, it's wonderful." Amanda's new voice surprised
her. Slightly husky but quite a lot higher than before and unmistakably
female, she now knew that the pain had been worthwhile and no-one need
ever know her secret.
Hugging the surgeon and with tears of joy streaming down her face, Amanda
left with Sue for the journey home.
Over the coming months, the bruising, swelling and numbness disappeared
and Amanda became ever more confident in her new persona. As she took a
new job on the cosmetics counter of the local department store, no-one
guessed that she had once been male and her sales figures made it
abundantly clear that men went out of their way to be served by her
(most, but possibly not all, buying gifts for their wives, of course) and
women valued the advice from someone so obviously expert in their field.
But most importantly, Amanda was finally becoming who she was always
meant to be. She loved being a woman and, whilst she was not proud of
the pain and upset that she had caused her wife and children, she
reflected on the fact that, if her wife had been more understanding, none
of her dreams would have come true. But most of all, she had Sue in her
life, her soul mate who had shown her the way and for that she would be
eternally grateful.
EPILOGUE
Amanda was jolted back to reality from her daydream by the sound of a car
horn outside.
"Come on darling, it's time for us to go to the airport. Just think, the
next time you enter our house, you'll finally be a complete woman and I'm
so proud of you."
And with that, Sue kissed Amanda on the cheek before they both picked up
their bags and made their way to the taxi waiting outside.
THE END
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