Caitlin and James Part three
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Caitlin And James - Part Six free porn video
Caitlin and James - Part six
Chapter 18 - The skirt debut - Getting ready
I wake up and give my darling Jamie a squeeze.
I fully open my eyes and realise I'm hugging a pillow instead, that's why
it it felt strange.
I look around - yes I'm in Jamie's bedroom, but where is he?
Today's the day we go into his office and ask about him wearing skirts
and dresses to work.
I can't hear him, he hasn't panicked and left has he?
I lie back down and think. A few moments later I hear the distinctive
sound of high heels on a stone floor, he must be dressed and in the
kitchen.
He walks into the bedroom with two mugs of coffee, hands me one, and sits
on the side of the bed.
"I woke up a bit earlier and couldn't go back to sleep, I hope I didn't
wake you Caitlin," he says.
I squeeze his knee through his skirt, and tell him I only just woke up.
Jamie's wearing everything he laid out last night, except he's not
wearing his hair in a bun, its down and still a little bit wet.
"You look lovely sweetheart," I say.
He smiles, and as he does, he flicks his hair back, revealing one of his
silver button earrings.
It's so cute, what he just did, so feminine.
We sit for a few more minutes, then I get out of bed and hit the shower.
As I come out of the shower, James is sitting at his make-up table
putting on his make-up, wearing an alice band to keep hair out of his
face. I quietly chuckle at the fact that I'm pairing male pronouns with
words I never have - his make-up, his skirt, his large hoop earrings.
As I'm getting dressed he starts blow drying and brushing his hair.
James turns off his hair dryer, and starts to put his hair in a bun. I
subtly watch this because I've never put my hair in a bun, well, not a
really neat one, and would like to do Jamie's hair one day.
He brushes his hair, and gathers up the hair into a ponytail up in the
middle of the crown of his head. I'm surprised he doesn't tie off the
ponytail, instead he starts twisting his ponytail and it starts to take a
spiral shape to form a bun.
He wraps the rest of hair around the bun, picks up one of the four
hairpins laid out on his make-up table and secures hair. He then gets a
thick blue elastic hair tie and wraps that around the bun which keeps the
four pins and the hair all in place. The pins are similar to bobby pins,
shaped like a very narrow 'U', but not closed like bobby pins.
He then takes off his alice band and brushes out his bangs, and then
clips his button earrings to both of his ears.
By that time I'm fully dressed and he then does my hair, I'm just wearing
it down today.
As he does my hair I notice his skirt is quite long, falling to about
halfway between his knee and ankles, tea length I think they call it. It
also flares out a little bit, I wonder if he's wearing a petticoat, I
never got to see what undergarments he is wearing. That'll have to wait
until tonight.
We then have breakfast, I notice he's not wearing lipstick. With
everything else he's wearing he may as well put some lippy on.
Later on he comes out of the bathroom after cleaning his teeth and goes
straight to his make-up table, that's when he does his lips.
He has to wait while I put my subtle make-up on - just a little bit of
foundation and mascara - personally I don't like lipstick, except for the
taste of it when I kiss Jamie.
In the kitchen James hands me a lunchbox of sandwiches with last night's
roast pork, as well as my water bottle, I put them - and my make up
pouch, in my briefcase. For the past few months I've tried to avoid
carrying a handbag. especially for work - I carry enough already. Instead
I keep a very thin wallet in the pocket of my pants, as well as key
holder that has a coin pouch.
Jamie has a final check of his handbag - he doesn't have the same option
as me because skirts don't have pockets - then we head for the front
door.
He stops and has a final check of himself in a mirror near the front door
of his house.
"Darling, you look gorgeous," I say, keen to get going.
He smiles, thanks me, looks at me, then the smile quickly fades.
"You're not wearing earrings Caitlin. You promised you'd wear hoop
earrings.
I apologise, go to his bedroom and put on the small hoops I was wearing
last night.
When I come back to the front door, James is still looking at himself in
the mirror smiling, the smile gets even wider when he sees me.
"You look even more gorgeous Caitie," he says kissing me.
Chapter 19 - The skirt debut - The meeting
The drive to work is very quiet.
When we were stopped at a couple of traffic lights I put my hand on his
leg and reassure him that everything is going to be okay. It'll only be a
quick meeting and after that I'll drive him home.
We pull up to his building - the same parking spot as yesterday.
"Caitie, I'm nervous."
I take hold of his hand and tell him I'll be right with him.
"Will you speak up for me if I'm lost for words? I might get even more
nervous in there. I mean, will you speak even if I don't prompt you to?
"That's what I do for a living darling," I say squeezing his hand a
little tighter and leaning over to kiss him.
"Is it okay if I change into some jeans and a blouse for uni this arvo.
"Of course dear," I say kissing him again.
I get out of the car and go around to his door let him out.
He used to thank me for opening doors for him and helping him out of the
car, now it's just what we do.
We head to his building arm in arm, as we're waiting for the lift
(elevator), I rub his back.
As we're getting in the lift, one of the middle aged women from yesterday
gets in behind us.
"Hello Pam," says Jamie.
She says good morning and compliments him on the outfit, adding that he's
wearing very cute heels.
"So you've finally taken the final step, good luck my dear," she says.
She gets off on her floor, waits for Jamie to get out but he says he's
seeing Pauline first.
"Yes, I imagine you are. Don't worry honey, you look lovely."
We get off on Pauline's floor, we're holding hands and Jamie guides me to
Pauline's outer office.
When we get there, a very pretty young woman squeals when she sees James
in his skirt and heels. Grabs his shoulders and air kisses him.
It must be Tara.
She makes a fuss over him, says he looks adorable.
"So this is what the meeting is about, you want to ask about wearing
skirts and heels, don't worry Jamie we've been waiting for this a while,
especially after we found out those outfits also come with skirts as well
as pants," the young woman says.
She looks at me: "You must be Caitlin, I'm Tara, Jamie and I went to
school together, we've been best friends ever since, he was even going to
be one of my bridesmaids at my wedding before it was called off," she
says shaking my hand.
"By the way, your idea of calling him Jamie is absolutely perfect, it
totally suits him, we're all starting to do that.
"You look nervous Jamie, don't be, if there are any men that resent what
you're wearing they're just jealous, probably wishing they could look as
nice as you - remember, men can be just as bitchy as women."
Does she ever stop talking?? But I smile, happy that the two people from
his workplace that we've met so far have been supportive.
Tara tells us to go into Pauline's office, tells Jamie she'll get him a
cup of chamomile tea. She offers me something but I decline.
In the tastefully decorated office is a small woman behind a desk talking
on the phone. She has short greying hair, and is wearing a grey jacket
over a simple blue blouse. She would be well into her 40s, possibly 50-
years-old but she's very good looking.
We sit down, I watch and enjoy how James clears his skirt, sits with his
knees together, with his hands folded neatly resting on his knees - he
has his handbag hung from the arm of the chair.
About half a minute later Pauline hangs up the phone, sighs, looks at us
and smiles, then her mobile phone rings, she answers it.
Tara comes in and hands James his tea in a cup and saucer.
As she waits for Pauline to get off the phone Tara absentmindedly plays
with the hair on the back of Jamie's head as well as his bun. Jamie makes
no response, just sipping his tea a little nervously. I suppose he'd be
used to that kind of touchy feely attention if he's best friends with
someone as bubbly as that.
When she sees me looking at her, she moves her hand to his shoulder.
I wasn't giving Tara the "Hands off" look, I believe I was smiling.
Pauline gets off the phone.
"That was the CEO, he thinks I should consider starting a little early
today," Pauline says with a wry smile, shaking her head and holding out
her hands as if to say, 'well I'm here'.
"You were here before I got in," Tara says.
"7.15 in the a.m. to be precise," Pauline says.
"You've got those assessors you were looking for on line two."
"Are we all set up to move downstairs today," Pauline asks.
Tara says yes, Pauline tells us to wait a little longer, and answers the
phone.
Tara then crouches down, rubs Jamie's arm and is about to say something,
then Pauline starts snapping her fingers, and waves her hand, shooing
Tara out of the room.
Tara closes the door, and I wonder what that was all about.
James leans over to me and starts whispering to me.
"Pauline's office is up here on this floor with customer service, but on
a day like today all the action will be downstairs on my floor where
claims and sales are. I imagine people are still trying to get cover even
though the fires have started burning, and there'll be people wanting to
make claims," James says.
"She doesn't have an office down there she'll set up anywhere really, she
just wants to be on hand to help."
"And I'll be right outside the switch room, in Justine's office today,"
Pauline says hanging up the phone.
She walks around her desk, looking very smart in her pants suit, with
black ladies loafers, shakes my hand. James then introduces us to each
other.
Pauline looks at me and smiles for a few seconds, then shakes off the
smile and stands in front of Jamie taking hold of one of his hands.
"Darling, Siobhan's daughter is sick again, and Anne had a car accident
last night, she's okay, only a few bumps and cuts, but they want to keep
her in hospital to make sure she's alright," Pauline says, looking right
into Jamie's eyes.
"I know your studies are important to you and that you have classes this
afternoon, but I really need you to work today.
"We're two short on the switchboard on a day when I could have used an
extra."
James nods, and says: "There was something I wanted to talk to you about
Pauline," he says smoothing out his skirt.
Yep, I guessed as much when you walked in dressed like that. You look
very nice by the way," Pauline says.
"There's no problem with you wearing heels, skirts or dresses to work,
we'll have to sort out a few things over the next couple of days but the
most important thing is for you to work today, because everyone really
needs you."
James looks even more nervous, I can imagine it's very hard to say no to
Pauline - she's very charming and persuasive.
He looks at me, and I start to speak.
"Well there are some immediate issues, such as what toilet he uses,
explaining why he's wearing a skirt and heels, people constantly asking
questions can be very draining on a person, and I suppose Jamie coming to
work dressed like this is probably quite a big event for him," I say to
Pauline, who is taking it all in.
"Like a gay coming out of the closet," she asks.
"Sorry darling, I know you're not gay, you prefer women, but there is an
equivalency," she say reaching over to squeeze his hand again.
I tell her she's right, it's all about his identity, and with him it's
not as simple as being a woman trapped in a man's body.
"Something like a third gender, I've been reading up on this subject
lately, there are many societies that recognise more than two genders,
but Western society is slow to recognise it," Pauline says.
"Or I'm just a feminine guy who prefers to wear women's clothes - it's
not an arousal thing, I just feel more comfortable and more myself not in
boring men's clothes," Jamie says very assertively.
"Well, I suspected that this has been coming for a few months, and I
don't think anyone will be surprised about a skirt, and you usually use
the single stall toilets - the disabled toilets - don't you?" Pauline
asks James.
James nods, and says he's "happy" to work today, but needs 10 minutes to
make a couple of phone calls and send an email.
"I never thought you'd let me down darling," Pauline says, taking Jamie's
tea cup from him and putting it on her desk.
We'll set your starting time for 8.30am that'll give you more than enough
time, and I'll arrange for human resources to visit from head office
tomorrow morning to sort a few things out, such as an email to staff, and
possibly an information session."
"We're ready Pauline," Tara says, standing in the doorway.
"Good, lets head downstairs for a very busy day ... And, James' big day,"
his boss says helping him out of his chair.
We take the lift downstairs and James and I head to a lunchroom where he
stands next to a vending machine getting his purse out of his handbag, I
ask him what he wants, and I get him a bottle of water.
As I'm doing that Jamie sits down clearing his skirt as he sits down - I
love watching him do that, it's so ladylike.
He gulps down a couple of mouthfuls of water as he takes off one of his
earrings and makes his phone calls. One sounds like it's to a classmate
who will pass her notes to him (I assume it's a her), and the other
sounds like it's to a his lecturer letting him or her know he'll be late
with an assignment that he was meant to hand in today.
James explains that he was going to do some final work on it today but
was called into work because of the bushfires. It sounds like he's been
given until Monday to hand it in.
"I can't remember who I was going to email," he says hanging up and
clipping the earring back onto his ear.
"We're not allowed to use our mobile phones while we're working, so it'll
just have to wait."
He reaches over to hold my hand, I reassure him everything will be fine.
We sit there for a few more minutes, Pauline said either she or Tara will
come over and get us, Pauline's probably explaining to Jamie's colleagues
what's happening with him today.
I get up and stand behind him and give him a hug while he's still sitting
down.
Our intimate moment is interrupted by a woman yelling.
Something about being a few minutes late on a day when she wanted
everyone to be early.
"That's Belinda, the claims manager," Jamie says, getting up and moving
to the doorway of the lunchroom, I follow him.
The woman sounds like an absolute horror to work for.
We then see Pauline walk up to Belinda and the two guys. She's not
yelling but she's talking in a very firm tone.
"That's enough. In case you hadn't noticed you're standing next to
someone who is on the phone while you're yelling," she says with her arms
folded.
"Do you really want a customer to overhear you."
Belinda points at the two guys, and tries to interrupt, but Pauline holds
up her hand to silence her.
"I want them on the phones NOW - we'll talk later."
The two guys go to their desks and get to work with a look of relief on
their faces.
Belinda sits down, and Pauline walks over to us.
"Is everything okay Pauline?" Jamie asks.
Pauline nods, but also rolls her eyes.
"Are you ready darling," she says taking hold of one of Jamie's hands.
Jamie takes a deep breath, nods, they then walk over to the switchboard
room.
I follow them, Pauline and Jamie are still holding hands as they walk.
Jamie has his water bottle in his other hand and his handbag is hanging
off his elbow.
I'm a little surprised at how familiar Pauline is with her staff, well,
Jamie at least.
As they near the door of the switch room about half a dozen women stand
up and follow Jamie and Pauline.
As he enters the room, quiet applause breaks out. Justine his supervisor,
stands up hugs him, and says: "Congratulations Jamie."
Bess
- 16.11.2021
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