Caitlin and James Part three
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Caitlin And James - Part Seven free porn video
Caitlin and James - Part seven
Chapter 20 - The skirt debut - Jamie at work
After I finish my first court hearing of the day I go to a waiting room
and take off my wig and check my phone, expecting messages from assistant
Felicity.
There are text messages from her but my attention is caught by one from
my lovely Jamie who is wearing a skirt and heels at work for the first
time today.
Jamie texts: "Haven't been made fun of yet but work is awfully busy - I'm
on my morning 10-min tea break."
I reply, saying that's good to hear.
He works on the switchboard at an insurance company, and they're busy
because there are bushfires in two states.
Jamie sends another one asking if I could phone him on his lunch break
between 1pm and 1:40pm.
I say that's no problem, that's when I'll be back in the office, probably
having my own lunch.
He thanks me.
My mind wanders, and I start to think about Jamie's day. We originally
went in to ask about him wearing skirts or dresses to work and, of
course, if he's going to ask that he should dress that way. But his boss
said she needed him to work because two colleagues couldn't make it to
work today, and him wearing skirts is no problem.
It must have been such a shock to him for that to happen, but he's taken
it in his stride and he's been quite brave actually.
I think about what he's wearing today, he looked so cute and so adorable.
I check my phone, not for more messages but for pictures of Jamie, in
dresses, in a shorts and blouse outfit, and another of him wearing his
hair in plaited pigtails, like he wore the first time we met.
I'm smiling widely and looking at my phone when I'm interrupted by a
colleague.
My day continues.
Chapter 21 - The skirt debut - Lunch over the phone
"Are you sure no-one has hassled you? If that's the case, then this has
gone remarkably well."
"I've been stuck on the switchboard all day, except for a brief 10 minute
break this morning, so no-one's really seen me in a skirt and heels,"
James replies.
"There a couple of girls ... well, women a couple of years younger than me,
cornered me when I was getting a cup of tea, and asked me a lot of
questions, they said I look quite nice, but a little bit frumpy."
I'm in my office, talking to my boyfriend James on the phone during his
lunchbreak, while I eat my salad.
"Justine, Tara and Siobhan call them 'the mean girls', because they would
be the ones at high school who think they are so hot, and act superior to
everyone else except for guys they're interested in," James adds.
"Sounds like they called you frumpy because they were jealous of you cute
you looked," I say.
"Oh don't be silly Caitlin," Jamie says giggling.
"Darling, I'm serious, you're prettier than most women, I had a look
around your office this morning and I reckon you were the prettiest one
that was there ... except for me," I say.
"Justine and Tara would come a close second behind you, but seriously
you've got nothing to worry about, you look very lovely, and that helps a
lot, there's a
lot of power in being beautiful. Enjoy it."
We talk for a bit more and Jamie tells me he won't be able to finish work
until 7.30pm, I promise to pick him up from work.
"Darling there's one thing I'm worried about," I begin to ask.
I tell him that I know he doesn't want to be a woman, but for people who
don't know him it helps that if he's dressing that way then he should
look enough like a woman so he doesn't get hassled by strangers.
"Sweetheart, how often do you shave?"
As I ask that, I try to remember if I've ever seen him shaving his face.
"I don't shave," James replies.
I express my doubts, adding that as a male he lacks nothing in bed - he
must have facial hair.
Jamie giggles for a bit and thanks me.
"When I was 13 I started getting some facial hair, and told Aunt Mary
that I never wanted to have facial hair, and she took me to a place where
they do somethings called electrolysis - I've had it done a couple times
since, and haven't had any facial hair for three years, so far," he
replies.
"I also get my legs waxed every month and a full body wax every three
months - I hardly get any body hair at all, so it doesn't hurt much at
all."
I express relief, saying I was worried about him working so late and
getting a five o'clock shadow, it would be a dead give away.
"That's one thing I'm thankful of, I'm also thankful I don't have a
prominent Adam's Apple, it's there, but it doesn't stick out, that's
probably why my voice isn't that deep," James says.
"Anyhow, I'd love to keep speaking to you Caitie, but I really should eat
something - I don't like eating while I'm talking on the phone."
We say goodbye, and I tell him that I love him.
As I'm hanging up the phone, my assistant Felicity, walks into the office
with a smirk on her face.
"Is that your boy?" She asks, with the emphasis on the word "boy".
I think Felicity is more amused that I'm dating someone 10 years younger
than me, rather than what he wears, although I haven't told her about his
skirts and dresses yet, just the other feminine attire.
"Yes that was Jamie," I say emphasising his name. Next time I'll just
tell her to address him by name.
She tells me she's about to head off to the dentist. She's getting root
canal work done - ouch. And that her phones are forwarded to another PA.
I say goodbye and tell her not to worry about coming back today, I'll
just be doing a bit of work in the office.
I sit there for a couple of minutes, relieved for Jamie, and for myself,
what appeared to be a very very hectic day, ended up quite light.
The preliminary hearing in one case was very brief, and other case ended
quickly, with summing up adjourned for tomorrow.
I head to my office fridge to get half a glass of wine, as I'm pouring it
I realise what Jamie said to me. Did he chastise me for eating on the
phone?
Very subtle, he must have heard me eating while on the phone. Probably
another of Aunt Mary's many rules.
Chapter 22 - The skirt debut - Afternoon coffee
I finish all the work that I wanted to get done today, and instead of
going home to Jamie's place I head for his office. He mentioned at lunch
that his afternoon tea break will be around 4pm so I'll manage to get
there by then.
I park near his building and go up in the lift.
The doors open.
"GET OUT OF MY FUCKING WAY!"
It's that dreadful woman who was yelling at her staff this morning - I
think her name's Belinda.
She's carrying a cardboard box, and there's two security guards behind
her - it's obvious she's been sacked and is being escorted out the
building.
I move out of her way, one of the two security guards follows her, the
other stands aside to let me out of the lift with an apologetic look on
his face.
"I'M GONNA TAKE A CAB TO PERTH, YOU'LL BE IN SO MUCH TROUBLE FOR GIVING
ME A CAB CHARGE, I'LL MAKE YOU PAY FOR GETTING RID OF ME," the awful
woman says to Pauline who is standing in the lift lobby.
The doors close, Pauline sits down in one of the chairs there.
She motions me to sit with her.
I sit, and muse that's this is where Jamie comforted me the first time we
met, he looked so adorable, especially with the plaited pigtails.
Pauline sighs.
"Are you okay Pauline?"
She nods: "If I didn't fire her, I'd be in trouble. And despite all the
unpleasantness I tried to do something nice to get her home easily, and
then she throws it in my face. She's totally without grace."
"There's no way she'd get a cab to Perth, no driver would take the fare,
because it also means they have to drive back all that way without a
fare," I say, immediately going into lawyer mode.
"Besides your company would have precautions in place, such as maximum
that can be charged to your cab charge account per trip, and cab charge
cards only being used for what they were meant for."
"I know that dear, it's just her being so unpleasant," Pauline says
patting me on the arm.
We sit in silence, for a couple of minutes. In situations like this my
instinct is to give advice, but sometimes people find that annoying, I
think this is one of those times that it's probably best to wait for
Pauline to say something.
"Besides, who would put up with her on a road trip that long - it would
take three or four days minimum," I say, trying to ease the tension.
"She'd probably be dumped in the middle of the Nullarbor," I add.
Pauline chuckles, puts her hand over her mouth, looks at me and shakes
her head, as if to say we should not be laughing at something like that.
She reaches out for my hand, we hold hands for a moment or two, and she
looks me in the eyes and asks: "Caitlin, are you here to check up on
Jamie?"
Pauline asks that question with a sweet smile.
I nod, a little bit bashfully.
"That's delightful. He's very lucky to have you."
"Don't worry dear," I've been sitting near him all day and no one's been
awful to him."
Pauline gets up and we walk to the switch room where Jamie is working.
I watch him at work through the window of the switch room as finishes off
his calls before going on a break.
He looks so nice, so secretarial with his hair up in a bun, and sitting
with an excellent posture.
The room has three desks side by side, all looking out a window
overlooking the surrounding suburbs. Behind their desks is a window
looking out to the rest of the office.
If you're walking past you'd have stop and look quite hard to notice
Jamie's heels and stockings under his desk.
Each desk has a switchboard terminal (these days they just press buttons
- no plugs), a computer, I imagine for looking up phone numbers and
sending emails for phone messages etc, and in the corner up high on the
wall there's a television silently playing a news channel. Not only are
there bushfires but the TV's news ticker says there's cyclone looming off
the north Queensland coast - it's very late in the year for either.
Justine's in the middle desk, there's an older women I don't know to her
left, and Jamie is on the far side to Justine's right.
Tara walks into the room, Justine gets up and Tara takes her seat.
Justine notices me, gives me a cheeky smile, turns around and taps Jamie
on the shoulder, and points to me.
Jamie gives me the biggest smile he's ever given me, and waves while
still talking on the phone, I wave back.
"It's not lover boy's break yet, he'll just have to wait, " Justine says
to me as she leaves the room.
"How are you Caitlin?"
I nod, tell her I'm fine.
"I'm getting coffees for everyone, wanna take a walk?" She asks.
"Well this is a nice surprise, he almost jumped out of the seat when he
saw you," she says as we stand in the elevator.
I notice Justine's short skirt and high heels, much shorter and higher
than Jamie's, quite sexy really.
I can't wait to see him in an outfit like that, but I'm not going to push
him - I think he's quite conservative.
I look up at Justine's face, her cheeky grin widens, I think she noticed
me looking at her legs.
"So you met Tara this morning? I heard she made quite a fuss over Jamie."
I says yes, and ask about his relationship with Tara - Jamie's old
schoolmate.
Justine says it's just plutonic, Tara prefers masculine men, and sees
Jamie more as a little brother ... or sister.
She says Tara protected James at school when kids teased him for his
gentle nature, long hair and both ears pierced (which was rare for blokes
back then), they were almost inseparable at school.
"And you don't have to worry about me either, I'm getting married in
September. Jamie's very cute but I've always seen him as one of the
girls. It doesn't matter what he wears, he just relates so well with
women, and fits in. Even when he dressed more like a boy, you had to
remind yourself that he's a guy," Justine says as we're about to walk out
of the building.
Justine gasps, turns around with a shocked look on her face, and grabs my
arm.
"Quick, we've got to go out the other way,' she says, trying to lead me
to the other door.
I stand there and notice Belinda outside the building smoking, and pacing
up and down with an annoyed looked on her face.
"I never want to speak to that one ever again," Justine says, pulling my
arm.
"Yes, I ran into your claims manager as I was entering your office," I
say.
"EX claims manager," Justine interrupts.
"She's been sacked, I don't ever want to talk to that woman again, or
about her - I've had so many clashes with her."
We're now walking down the street, arm in arm, I'm a little self
conscious about this apparent public display of affection from another
woman.
Jamie seems to be surrounded at work by women who are very touchy feely,
but I feel I have to ask my next question.
I ask about Pauline being so affectionate with Jamie, calling him
darling, and holding his hand as they walked across the office this
morning.
"Yeah, I imagine she put the charm offensive on James to get him to work,
but he was never going to say 'no'."
Justine says when Pauline came into switch room to tell everyone that
James is working today, and about what he's wearing, a couple of women
from Sales were close by, and one suggested they show an obvious sign of
support, that's why Pauline walked across the office hand in hand with
James, and why he was applauded.
"It's also why I gave him a big hug, he's gotten lots of hugs today,
nearly all women in office are supportive," Justine says.
"How can you not hug him, he looks adorable in those little Miss Prim and
Proper outfits.
"I think hardly anyone is surprised he's finally in skirt and heels, but
many of us realise it's was a big step for him."
We get to the coffee shop, Justine orders and gets out her purse, I
suddenly realise that she's paying for the coffees for her staff out of
her own money.
I'm very impressed by that, when she tells me that she is, and that she
does it occasionally to be nice to her staff.
I insist on paying.
I ask about her being the switchboard supervisor, in such a position of
responsibility at such a young age.
"Jamie says you're younger that him."
Justine screws up her face and laughs.
"I'm three months younger than him, that's hardy a big difference. I got
the job straight out of school, took some workplace courses, and I was
promoted about six months ago."
As we walk back, I ask about her colleague who had a car accident this
morning.
"Oh Anne called early this afternoon, she's fine but still shaken. She
got to speak to everyone briefly, she was pleased to hear about Jamie,
sad she wasn't there on his debut, but she's proud of him," Justine says
as we walk back to the office.
"That's from a very conservative church-going lady. She cares about
people and doesn't want to see anyone hurt."
We walk for a bit more, and then outside the building, Justine stops
walking, turns to me, puts her hand on my arm to give it a rub.
"Has Jamie told you he'll have to work late today and on Thursday,"
I nod and say: "7.30."
"I'll try to get someone else will do it on Friday, I imagine you and
Jamie will have something to celebrate," she says with a wink.
"Anyhow I'm giving him a 20 minute break this arvo, because he's working
so late and doing an 11-hour shift. He's such a great sport for doing
that."
Justine mentions that human resources might be coming to talk to him
tomorrow afternoon. Would I like to be there?
I tell her I'll move heaven and earth to be there with him.
"You're such a wonderful girlfriend, I'm so glad he's in good hands,"
Justine says, again rubbing my arm.
She says she'll keep in touch to let me know the exact time.
We get back to the office. As soon as Justine tells Jamie it's his turn
to take a break he rushes to me and give me a hug.
I struggle a little bit not to spill the takeaway coffees I have in
either hand, while he's hugging me.
"This is such a wonderful surprise Caitie," he says kissing me.
I look around, we've definitely got an audience.
"You're too good to me," he says.
I'm about to agree that I am too good to him, when he interrupts me with
another kiss on my lips.
He takes my arm and we walk toward the lunchroom where we were this
morning.
We sit down and I hand him his coffee.
"It's probably a good thing I had to work at short notice on a busy day
today. I haven't had much time to think about what I'm wearing. I almost
forgot I was wearing skirt and heels at one stage,' he says, sitting
down, clearing his skirt.
He reaches over and plays with the earrings I'm wearing - his smallish
gold hoops.
"You're still wearing them Caitie, they look so great on you," he says.
I get out my phone and show him pictures of myself from every hour of the
day wearing his earrings, proving I've worn them all day - at least
nearly all of the day.
I admit I took them off to make some phone calls early this afternoon.
He's impressed, especially when he sees a picture of me in my legal
attire.
"So I've kept my end of the deal. Have you worn your skirt all day?" I
joke, rubbing his knee through his skirt.
"I had nothing else to wear Caitlin," he giggles.
We sit there for a few moments, holding each others hand and sip our
coffees in silence, just enjoying each others company.
Then James starts organising dinner - with him at work he doesn't seem to
quite trust me to handle it.
He says there's some very recently frozen Chilli in his freezer, and
gives me detailed instructions on how to defrost it then heat it up.
At one point he's quite condescending, wanting to know in great detail
how I intend to make rice.
"Darling, trust me, I do know how to boil rice," I say squeezing his
hand.
We're interrupted by a guy walking into the lunchroom standing in front
of a vending machine and exhaling quite loudly.
I think it's one of the guys that Belinda was chewing out this morning.
"Tom. Are you okay?" Jamie calls out.
"Will be, as soon as I get some sugary caffine," he responds, without
turning around to look at us.
Jamie tells me that Tom is the assistant claims manager, and will
probably be the claims manager, now that Belinda got sacked.
"Is that right? James says to Tom who is walking over to us.
"Well, Pauline told me to tell customers that I'm the claims manager, not
the acting or the assistant, and she's promised to give me her 'most
sincere' recommendation," Tom says opening his can of drink.
"It's her decision but HR and the higher ups somewhere have final sign
off."
Jamie stands up.
"Tom, I'd like you to meet my girlfriend Caitlin," he says very formally,
and, it appears, with great pride.
Tom, stifles a chuckle, and says: "Really?".
Jamie says yes.
He looks at me and says: "Is that true?"
I nod confidently.
"Hey! That great. Wow James, she stunning." He turns to me and says: "I
mean, you're stunning."
"ANY guy would be lucky to have you, I mean, be with you.
"I'd better stop talking and change the subject."
Jamie and I both nod.
"Well, it's Perestroika day in the claims department today, feel free to
call me Gorby."
He says customers can now download claims forms from their website,
instead of having to phone for one. They've also put information at the
top of the website about who to call in an emergency. Many call claims,
but really need the State Emergency Service or the local fire fighters,
or just need info on evacuation centres.
"Apparently Belinda couldn't see why there's a massive increase website
traffic during a natural disaster," he says after taking another long sip
from his can.
"There was no help for them there, until now."
Tom says all these initiatives were vehemently blocked by Belinda, who
ignored everyone's advice, even Pauline's.
He adds the call volumes are much more manageable now. Jamie says calls
on the switchboard have noticeably eased off since around 3pm. Tom says
that's when the website was changed.
"Sorry to brag but I'm just so happy about today, and the things that
I've managed to get done quickly," Tom says.
Jamie asks what happened with Belinda, Tom says she was very rude to a
couple of customers on the phone today - that was the last straw.
Jamie says she's had a few written warnings already, Tom says five
including one for bullying Jamie and pulling his ponytail.
I note that in most workplaces you only need three.
"Well we wanted to be absolutely sure about her. She spent the past few
hours arguing with Human Resources that she shouldn't be sacked and
refusing to leave, Pauline had to call security," Tom says.
"She was never going to go quietly.
"Anyhow, I've got to go, more Glasnost to implement."
Tom's about to leave, then stops, turns around and crouches down next to
Jamie, and speaks to him in a confidential tone.
"Sorry mate, don't need to intrude, but what's the story. I mean you're
wearing a skirt today, what you usually wear is a bit 'out there' but
this is completely different.
Jamie says he's definitely not gay, reaching out to hold my hand again.
"I'm just a feminine guy who prefers to wear women's clothes, and I'm
almost absolutely certain I'm not a woman trapped in a man's body."
"Cool, that's easy enough to understand," Tom replies and walks off.
I mention to Jamie that he sounds like a lovely guy, and I'm happy
everyone is so supportive.
Jamie says Tom and the other guy Belinda were chewing out at 8.30 this
morning were coming very early today anyhow. Tom usually starts at 11am
and the other usually starts at 0930.
We walk back to the switch room and kiss each other goodbye, and I
promise to pick him up at 0730.
As I'm waiting for the lift, Tara grabs me around the waist.
"Jamie is so lucky to be with you, he's absolutely head over heels in
love with you," she says.
We get in the lift and she's talking at a million miles an hour,
peppering me with questions.
Tara links her arm in mine as I walk out to my car, still talking - gee
she's bubbly.
We say goodbye, and she surprises me with a kiss on the cheek.
Chapter 23 - The skirt debut - The evening
After having a nap for an hour or two, I get things ready for Jamie.
I run a bubble bath, he didn't ask for this, but I know he loves bubble
baths.
I also make sure everything is ready so I can make dinner quickly when we
get home.
Poor Jamie must be exhausted after an 11-hour shift. I've done some long
work hours in the past, but the work itself was varied and you could go
at your own pace.
But to be sitting there constantly answering a phone would be very
intense. And doing the same thing over and over, for half a day would
drive me bonkers.
I drive to Jamie's office, park right outside, he's not there, I phone
him, it sounds like he didn't want to come outside until he knew I was
there.
James walks out of the building with Tara. I knew this in advance that
she would be staying back with him to finish off her own work as
Pauline's assistant, and to help Jamie if the phones get really busy.
As they approach I get out of the car to greet Jamie, we hug, and Tara
has the back seat door of my BMW already open to let Jamie in.
I noticed they are both in a giggly mood.
"Tom was crestfallen when he found out that you were giving Tara a lift
home Caitie. I think he wanted to make the moves on Tara," Jamie says.
"He cornered me earlier and asked about her, and has been pestering me
with emails, all of which Tara has read.
"Tara's been laughing how I'm the office cupid, the perfect go-between
for the boys and the girls."
Tara mentions how Jamie's responsible for introducing Justine and her
fianc? to each other.
"Tom really was obvious and awkward when he came into the switch room as
we were finishing up this evening. It was so cute and funny," Tara says.
Tara pesters Jamie with more questions about Tom.
I look at her shapely legs and her short skirt, and then her curly
strawberry blonde hair that only just reaches her shoulders - Tom and
Tara would be a lovely couple.
Tara stops talking to Jamie, and starts giving me directions to her
place. She's been sharing a three-bedroom flat, only a couple of streets
away from Jamie, with two other young women since her wedding was called
off.
After we drop off Tara, we quickly get back to our place and as soon and
we're through the door, I grab Jamie, hug him from behind and kiss him
and tell him how proud of him I am and congratulate him on his first day
at work in skirts.
I love it how he squirms, and tries to break away but then gives in and
accepts my embrace.
I take him to the bedroom so he can strip off his clothes, while I top up
the bubble bath with hot water.
Jamie walks into the bathroom naked, and gets in the bubble bath still
wearing his make up, earrings and with his hair still in a bun.
I go to the kitchen and return with a couple glasses of French Champagne.
We toast to what I say I hope will be the first of many days, perhaps
years, of Jamie in skirts and dresses.
He looks so perfect, in the bath, all dressy from the neck up, but naked
from the neck down.
While he's in the bath I cook the rice, and heat up Jamie's home made
Chilli.
About 10 minutes later, I head back and Jamie is in a pink nightie at his
make up table, wiping off his make up.
I fold and hang up his clothes that were dumped on our bed, and notice
that he was wearing a camisole that would come down about halfway down
his thighs - that's why his skirt flared out a bit.
When he's finished, I stand behind him and I undo his bun and brush his
hair.
He smiles and sighs as I brush his hair, He obviously finds it very
relaxing.
I head to the kitchen to finish dinner, Jamie comes out a little later.
I guide him into the dining room.
He laughs when he sees the dining table lengthened, and a table setting
and either end of the long table.
I sit him down, I top up his champagne, and then serve him dinner.
It's really nice that he pampers me so much, but tonight I'm getting a
kick out of returning the favour, it looks like he appreciates everything
I'm doing.
We start eating dinner, but a couple of minutes later Jamie moves his
table setting up to my end of the table, right next to me.
"I think we can only talk to each other on our mobile phones that far
away Caitie," he says.
"The dinner is lovely, the champagne is lovely."
He stand up and reaches over to me, kisses me on the cheek.
"And you're lovely too."
Vicky
- 18.11.2020
- 16
- 0
