The Fifth Floor
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The Fifth Date free porn video
The Fifth Date
By
Sarah Goodwoman
Chapter 1
Scott paced back and forth with looking at his cell phone in his hand.
He was only a half hour away from having his fifth date with Monica and
was making big decision. He was either going to cancel the date or go
through with it. He strongly wanted to enjoy the evening with Monica, he
found her wonderful, yet he knew that if they had their date it ended
their budding relationship.
Scott knew it will end his relationship, the fifth date always did. No
matter how great he and the woman he was seeing got along, there was
never a sixth date. He did find solace in the fact it was not for he did
anything wrong. In fact, Scott knew if he did a certain wrong thing,
kept his secret any longer, he would have had a sixth date with any of
them.
Scott still did not regret why he never had a sixth date since college,
for it was for him doing the right thing. He would tell his date a
secret, he crossdressed. Scott felt it was not fair to a woman he wanted
to be close to not to tell her. She had the right to know this fact
before they got serious.
At first Scott told the woman but now he shows them he is a
transvestite. He went from telling to showing his date for it was less
painful for him. He only had to deal with rejection if he showed them.
When he told them he also had to deal with the humiliation of them
laughing when they thought he was joking.
Scott kept on looking at his phone and thought that Monica had to be on
her way by now. He can still back out of the date. He did not know how
to. He cannot tell her the truth, he feared her reaction to him
dressing. He also did not want to lie to her, she deserved better than
that. She needed to know the real reason why there would not be a sixth
date.
Scott cannot take his eyes off his phone and it rang. He saw the caller
name appear on the screen, Monica. He was overjoyed at reading it. Yes,
she is going to cancel the date and I do not have to do this. They will
make vague plans to meet up again and just become ghosts to each other.
He answered the phone and cheerfully greeted her. Monica, in a sweet
voice, told him that she was running early so she was wondering if it
was fine if she showed up now. Scott panicked, he was not ready. His was
almost done with his makeup and wanted a chance to make sure his outfit
was just right.
Scott told her that he was not ready yet. She asked him when he would
be. He wanted to say never, for one is never really ready for rejection.
He told her that she could just come in, his front door would be
unlocked.
Chapter 2
Monica was in a great mood all day, she had another date with Scott, a
man she found wonderful. She joked to her friends that she could not
decide what was the best part - he was cooking lasagna for her at his
house or that he was more interested in getting to know her as a person
instead of getting her in bed. She laughed to herself for she knew the
best part was Scott wanting to get to know her as a person.
She was so excited about the intimate dinner date that she left early
for it. She figured it would not be a big deal to show up a little
early. Then Monica thought that she it would be considerate to
call Scott. He might not be ready for company yet.
She walked into Scott's house and announced she was there. Scott yelled
down to her to get comfortable, and help herself to a cup of pre-dinner
coffee.
She went to the Kitchen and raw sugar and French vanilla creamer next to
the coffee maker. That paused and put a smile on her face. She knew that
Scott drank his coffee black so he got them just for her. That little
deed of getting what she liked to add to her coffee just strengthen her
notion he was a keeper.
She went to the living room and enjoyed her coffee while waiting. She
thought about how perfect the night is going to be. Scott was impressing
her the right way by being himself.
Scott told her to close her eyes he is coming down. Monica asked why.
Scott, sounding a little nervous, asked her to please humor him. She
said fine. Laughing to herself, Monica thought that Scott must have
gotten her flowers.
Chapter 3
Monica opened her eyes and saw Scott standing in front of her in a gray
pencil skirt, a black T-shirt tucked in, and black heels. His makeup was
done to perfection and his hair. Scott hairstyle was tight curls. It fit
his short round face and his outfit.
The only part of his outfit which did not flatter his look was the frown
on his face. The frown on his face was more of a concern to Monica right
now than the clothes. She only knew him for a month but she already
deeply cared for him. She knew she was special, he was so much better
than the men she had been dating before.
Monica asked Scott what was wrong. Scott sheepishly said this was their
last date.
At that moment, Monica knew two things. Why Scott thought it was their
last date and that statement was the furthest thing from the truth any
statement she ever heard had been. She was not going to allowed some
pieces of fabric get in the way of her having such a good man. She asked
him why.
Scott was already for defeat so he was not prepared to explain the
reason why. He expected her to give one of the multitude of reasons why.
He must be gay, he was a freak. It is stupid for a man to wear women
clothes. He must stop dressing if he wanted to be with her. They all had
the common thread of the woman not accepting him dressing
Scott told Monica she would not want to date him for she disapproved of
how he is dressed now. That he understood that she must be disappointed
in him for not telling her sooner. He wanted to be upfront about his
crossdressing, but felt that him dressing is something he did not want
to share until he knew the person better. He understood that she would
not want to have the fifth date. He just really liked her and had to
show her why they would not be a couple.
Monica did not interrupt him once while he explained why he thought it
was over. She felt so close to him right now for he was bearing his soul
to her. She found him strong for doing so. She knew most crossdressers
never share the secret with others. Their secret got revealed only when
they were caught.
Monica told Scott, that was him disappointed in him. Those words
instantly vindicated Scott's preconceived notion about their
relationship being over. Monica then went on to continue she was a
little disappointed in him for thinking it was over. She understood why
he thought so, but she was not those other women.
Monica told Scott that she was not going to lose a great man for he
liked to wear a dress. That she must rather him than the men she had
dated before. It was much worse to her for a man to blow off their date
to hang out with his friends than him wearing a skirt. Monica then told
Scott he better go check on dinner and asked if there was anything she
could do to help.
Chapter 4
Scott did not know what to do next, he was in uncharted territory. The
fifth date never went this far. He was expecting to have an argument
with Monica. Then after she stormed out telling him to never contact her
again, to cry and forget to pull out the lasagna.
Yes, the lasagna needs to be checked. He got his bearing and told her
she could open the wine to let it breathe.
They went into the kitchen and Scott was shaking a little. Monica could
tell he was nervous and offer him a glass of wine. He smiled while
accepting it.
There was a silence, Scott was scared of saying anything to offend
Monica and Monica did not want to offend Scott with too many questions
about his dressing. She did not know what to call it, calling it a hobby
downplays it. Asking if it was sexual would be too personal, then again
she hoped to find out if it was.
Finally, after another sip of liquid bravery, Scott said, "Heather."
Monica inquizitly said, "Heather?"
Scott then told Monica, when dressed like this he referred to himself as
Heather. Monica told Heather to go on.
Heather took another sip of the potion of bravery to help herself to
continue. It did not work. So she said, "Sorry this is stupid. You are
here for a date with Scott, not Heather. I will take the lasagna out and
quickly change while we let it cool down."
Monica knew this was a delicate situation. She did not want to force
Scott/Heather into saying or doing anything which is outside of their
comfort zone. At the same time, she wanted to show she was open and
accepting to the female aspect of his personality having such a
prominent physical roll.
As Heather was leaving to go get changed Monica said, "Stay dressed how
you are if you like. I think you look great in that outfit Heather, you
have the legs for pencil skirts. I also need to know this side of the
man I am dating."
She paused for she thought she might have made a faux pas. Should she
have referred to Heather as a woman now or female? It did not matter to
her for that person in front of her is wonderful and she wanted to get
to know them better.
Heather smiled after hearing the compliment on her legs. She knew she
had great legs. They were long and slender. She always wanted to show
them off and was happy that Monica noticed them.
Heather remember that she was so caught up on being nervous about
meeting Monica she forgot to say how ravishing Monica looked in her
peach bodycon dress. Heather responded with a thanks and told Monica how
much her dress accents her curves and the color of went well with her
skin tone.
Monica was relieved that she did not offend Heather by calling her a
man. She also enjoyed the complement, for the details in it. Unlike most
men who just told her she looked great with being able to explain why,
Scott always articulated on why. Worse when other men did try to explain
why Monica looked great the reasoning was always sexually charged.
Monica asked Heather to tell her more herself. Heather said that she
would be more than happy to once she served them supper.
Chapter 5
Heather served supper and before Monica could ask any question, she
blurted out one of her own. "What would you like to know about me?"
Monica saw that Heather was still nervous and told her to talk like she
was on the first date with her.
Heather started to stumble around for what to say. She had no idea what
she would tell a date. She never had a in person conversation with
anyone as Heather, yet alone talk to someone who she wanted to get to
know in a more personal manner. Heather just repeated the question.
Monica wanted to have a conversation and not turn this into an
interrogation. She genuinely wanted get to know Heather and knew that if
it just became questions and answers it would not help them connect. It
would start to feel cold and formal. Then a good chance Heather will get
defensive. Monica wanted a warm and inviting atmosphere to their chat.
Monica knew she had to be patient and understanding. Being a
veterinarian made it that she could read body language and she could
sense how scared frightened Heather was. She did not want the silence to
get awkward but also could not think of a question.
The silence was getting deafening in the room as they ate. Then it came
to Monica she needed to take the lead on this date. Monica smiled and
started to tell a story from her childhood about playing house. She
hoped that Scott acted out on his feminine side when he was young also.
At the end of the story she asked Heather if she ever played house also.
Hearing Monica tell her about playing house brought back so many good
memories from her childhood. Heather was lucky growing up, she had a
sister, Stella, who was two years older and couple of the kids on her
street were girls. She was able to play with them.
Heather started to open up and told Monica about playing house. How
Scott would make the girls also allowed him to be the homemaker. How
Scott would love to have tea with the girls. How he would act like he
did not want to but would play dolls with them.
Monica loved seeing the twinkle in Heather's eyes as she was talking.
She also noticed that she used her hands more to talk and touched her
more. Scott was very personable when chatting with Monica, but it was in
a different manner. She also was curious about how Heather would refer
to herself as Scott in the third person. She asked her about it.
Heather had to think about the question for a moment for it was nothing
to her to see her male side as someone else. She put her finger up in
the air when she was finally able to articulate an answer.
"Monica, I am Scott. I refer to myself in the third person for even with
us being the same person, I am different as Heather. When I was young I
had to allowed myself to let this part of personality out. I wanted to
but had to think about it. Had to think it was fine to do so. As soon as
I thought it was fine I did not have to think about it anymore. So with
having to allowed myself to be this natural part of my personality it
just seemed right to refer to my male side now in the third person. I
know I do not it as Scott talking about Heather."
Monica wanting to be part of the conversation, for it to have a natural
ebb and flow, mention she thought it was good Scott was able be open
about Heather.
Heather smiled for she was enjoying being able to share who she was to
Monica. She wanted Monica to know all about who she was, both as Scott
and as Heather. She knew that this chat they were having would bring
herself and Monica closer to each other.
Monica told her that she did talk to Stella about Heather some. Stella
was the first person to catch her dressing. Heather told the story about
Stella catching her dressed. She was lucky about it for Stella was not
upset at seeing her kid brother in her clothes. She did not like the
outfit he had on and thought he had no sense of fashion. Scott explain
that it was for he just wanted to wear the clothes and did not take the
time to put an outfit together.
Stella laughed and told him he did now so do if you like. Scott did and
Stella was impressed with his style. Stella did impose one rule to
Scott, he had to buy his own panties and bras. While she would buy them
for him, but he had to give her the money for them
Heather then told Monica about his parents knowing but not approving of
Scott's "hobby". She did not like that they referred to it as a hobby.
How can wearing what you want to wear be a hobby, it is just following a
social norm. People wore clothes even when alone. Heather did laugh when
she mention on great thing about dressing is it did stop her parents
from making unannounced visits. Her mom and dad did once when Heather
was dressed to the nines in what she would have worn to the prom.
Hearing about the prom made Monica think about Scott/Heather's
sexuality. She knew that there was no correlation between a man who
crossdressed and their sexual orientation yet she was concern that
Heather might be straight. She knew that concern was unfounded: yet it
was real so it have to be dealt with. Lastly she knew that she could not
come straight out and ask Heather if she was straight or a lesbian. She
asked her who would have been her perfect prom date.
Heather's face perked up hearing that question for she loved it. This
was for she was spending time with who she thought would be her perfect
prom date. She quickly responded to Monica inquiry, "A woman who is
kind, caring and can bring me out of my shell, you."
The quickness and sweetness of the answer along with the conviction in
Heather's voice quickly made that baseless worry Monica had about
Heather disappear. That answer also made her realize that she loved
Scott/Heather. She knew that she was getting strong feeling for him but
the love was confirmed for how good hearing that answer made her feel.
She had a warm feeling inside which felt like home.
Chapter 6
"I love you!" Monica proclaimed.
Heather eyes water up with tears of joys and tears of relief. She always
dreamt of hearing someone as special as Monica saying those words to
her, but never dared to put much details into those fantasies. The
vaguer someone dreams were, the easier the letdown would be when they
never become real. As tears started to roll down her face she told
Monica she loved her back.
Monica went over, hugged and kissed Heather. She thought to herself this
is the first time she kissed a woman. She thought of how much more
tender Heather kissed her compared to Scott. She was pleasantly
surprised at how much she enjoyed it. Monica later thought that she was
lucky for she would get both kind of kisses from her boy/girlfriend.
After the kiss Heather wiped away the tears from her face and said, "Oh
no, my makeup is ruined. Let me go upstairs and changed."
Monica told her she did not have to, her makeup is not that bad and
Heather should be able to easily fix it in a moment.
Heather smiled and replied back, "That is true but everyone knows you
end the first date with a kiss and Scott deserves to finally finish a
fifth date."
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